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Sample records for abamectin emamectin benzoate

  1. Simplified RP-HPLC method for multi-residue analysis of abamectin, emamectin benzoate and ivermectin in rice.

    PubMed

    Xie, Xianchuan; Gong, Shu; Wang, Xiaorong; Wu, Yinxing; Zhao, Li

    2011-01-01

    A rapid, reliable and sensitive reverse-phase high-performance liquid chromatography method with fluorescence detection (RP-FLD-HPLC) was developed and validated for simultaneous analysis of the abamectin (ABA), emamectin (EMA) benzoate and ivermectin (IVM) residues in rice. After extraction with acetonitrile/water (2 : 1) with sonication, the avermectin (AVMs) residues were directly derivatised by N-methylimidazole (N-NMIM) and trifluoroacetic anhydride (TFAA) and then analysed on RP-FLD-HPLC. A good linear relationship (r(2 )> 0.99) was obtained for three AVMs ranging from 0.01 to 5 microg ml(-1), i.e. 0.01-5.0 microg g(-1) in rice matrix. The limit of detection (LOD) and the limit of quantification (LOQ) were between 0.001 and 0.002 microg g(-1) and between 0.004 and 0.006 microg g(-1), respectively. Recoveries were from 81.9% to 105.4% and precision less than 12.4%. The proposed method was successfully applied to routine analysis of the AVMs residues in rice.

  2. Persistence and risk assessment of emamectin benzoate residues on okra fruits and soil.

    PubMed

    Jyot, Gagan; Mandal, Kousik; Chahil, G S; Singh, Balwinder

    2014-08-01

    Emamectin benzoate, a synthetic derivative of abamectin, is found effective against fruit borer and jassid in okra crops. The present studies were carried out to study the dissipation pattern of emamectin benzoate on okra and to suggest a suitable waiting period for the safety of consumers. Following three applications of emamectin benzoate (Proclaim 5 SG) at 68.1 and 136.2 g a.i. ha-1, the average initial deposits of emamectin benzoate were observed to be 0.22 and 0.42mg kg-1, respectively. These residues dissipated below the limit of quantification (LOQ) of 0.05 mg kg-1 after 5 days at both the dosages. Soil samples collected after 15 days did not reveal the presence of emamectin benzoate at LOQ of 0.05 mg kg-1. Acceptable daily intake (ADI) of emamectin benzoate is 0.0005 mg kg-1 body weight day-1, which means an adult of 55 kg weight can safely tolerate an intake of 27.50 microg emamectin benzoate. Assuming an average consumption of 80 g okra fruit and multiplying it by average and maximum residues observed on 0 day at recommended dosage, the intake of emamectin benzoate comes out to be about 20 Itg and these values are quite safe in comparison to its ADI. These studies, therefore, suggest that the use of emamectin benzoate at the minimum effective dosages do not seem to pose any hazards to the consumers if a waiting period of 1 day is observed.

  3. Dissipation, transfer and safety evaluation of emamectin benzoate in tea.

    PubMed

    Zhou, Li; Luo, Fengjian; Zhang, Xinzhong; Jiang, Yaping; Lou, Zhengyun; Chen, Zongmao

    2016-07-01

    The dissipation and residue of emamectin benzoate in tea leaves and the residue transfer from tea leaves to tea brew were investigated by modified QuEChERS (quick, easy, cheap, effective, rugged and safe) combined with ultra performance liquid chromatography tandem mass (UPLC-MS/MS). The average recoveries ranged 85.3-101.3% with relative standard deviation (RSD) less than 15%. The limits of quantification (LOQ) were 0.005mgkg(-1) in tea leaves and 0.0004mgL(-1) in brew. Emamectin benzoate dissipated rapidly in tea with half-life (t1/2) of 1.0-1.3days. The terminal residues of emamectin benzoate were less than 0.062mgkg(-1). The leaching rate of emamectin benzoate from freshly-made tea to brew was <5%. The risk of emamectin benzoate at the recommended dosage was negligible to humans depending on risk quotient (RQ) value, that was lower than 1 significantly. This study could provide guidance for the safe use of emamectin benzoate and serve as a reference for the establishment of maximum residue limits (MRLs) in China.

  4. Characterization of Phenacoccus solenopsis (Tinsley) (Homoptera: Pseudococcidae) Resistance to Emamectin Benzoate: Cross-Resistance Patterns and Fitness Cost Analysis.

    PubMed

    Afzal, M B S; Shad, S A

    2016-06-01

    Cotton mealybug Phenacoccus solenopsis (Tinsley) (Homoptera: Pseudococcidae) is a sucking pest of worldwide importance causing huge losses by feeding upon cotton in various parts of the world. Because of the importance of this pest, this research was carried out to select emamectin resistance in P. solenopsis in the laboratory to study cross-resistance, stability, realized heritability, and fitness cost of emamectin resistance. After selection from third generation (G3) to G6, P. solenopsis developed very high emamectin resistance (159.24-fold) when compared to a susceptible unselected population (Unsel pop). Population selected to emamectin benzoate conferred moderate (45.81-fold), low (14.06-fold), and no cross-resistance with abamectin, cypermethrin, and profenofos, respectively compared to the Unsel pop. A significant decline in emamectin resistance was observed in the resistant population when not exposed to emamectin from G7 to G13. The estimated realized heritability (h (2)) for emamectin resistance was 0.84. A high fitness cost was associated with emamectin resistance in P. solenopsis. Results of this study may be helpful in devising insecticide resistance management strategies for P. solenopsis.

  5. Effect of Emamectin Benzoate on Root-Knot Nematodes and Tomato Yield

    PubMed Central

    Cheng, Xingkai; Liu, Xiumei; Wang, Hongyan; Ji, Xiaoxue; Wang, Kaiyun; Wei, Min; Qiao, Kang

    2015-01-01

    Southern root-knot nematode (Meloidogyne incognita) is an obligate, sedentary endoparasite of more than 3000 plant species, that causes heavy economic losses and limit the development of protected agriculture of China. As a biological pesticide, emamectin benzoate has effectively prevented lepidopteran pests; however, its efficacy to control M. incognita remains unknown. The purpose of the present study was to test soil application of emamectin benzoate for management of M. incognita in laboratory, greenhouse and field trials. Laboratory results showed that emamectin benzoate exhibited high toxicity to M. incognita, with LC50 and LC90 values 3.59 and 18.20 mg L-1, respectively. In greenhouse tests, emamectin benzoate soil application offered good efficacy against M. incognita while maintaining excellent plant growth. In field trials, emamectin benzoate provided control efficacy against M. incognita and resulted in increased tomato yields. Compared with the untreated control, there was a 36.5% to 81.3% yield increase obtained from all treatments and the highest yield was received from the highest rate of emamectin benzoate. The results confirmed that emamectin benzoate has enormous potential for the control of M. incognita in tomato production in China. PMID:26509680

  6. Environmental fate of emamectin benzoate after tree micro injection of horse chestnut trees.

    PubMed

    Burkhard, Rene; Binz, Heinz; Roux, Christian A; Brunner, Matthias; Ruesch, Othmar; Wyss, Peter

    2015-02-01

    Emamectin benzoate, an insecticide derived from the avermectin family of natural products, has a unique translocation behavior in trees when applied by tree micro injection (TMI), which can result in protection from insect pests (foliar and borers) for several years. Active ingredient imported into leaves was measured at the end of season in the fallen leaves of treated horse chestnut (Aesculus hippocastanum) trees. The dissipation of emamectin benzoate in these leaves seems to be biphasic and depends on the decomposition of the leaf. In compost piles, where decomposition of leaves was fastest, a cumulative emamectin benzoate degradation half-life time of 20 d was measured. In leaves immersed in water, where decomposition was much slower, the degradation half-life time was 94 d, and in leaves left on the ground in contact with soil, where decomposition was slowest, the degradation half-life time was 212 d. The biphasic decline and the correlation with leaf decomposition might be attributed to an extensive sorption of emamectin benzoate residues to leaf macromolecules. This may also explain why earthworms ingesting leaves from injected trees take up very little emamectin benzoate and excrete it with the feces. Furthermore, no emamectin benzoate was found in water containing decomposing leaves from injected trees. It is concluded, that emamectin benzoate present in abscised leaves from horse chestnut trees injected with the insecticide is not available to nontarget organisms present in soil or water bodies.

  7. Environmental Fate of Emamectin Benzoate After Tree Micro Injection of Horse Chestnut Trees

    PubMed Central

    Burkhard, Rene; Binz, Heinz; Roux, Christian A; Brunner, Matthias; Ruesch, Othmar; Wyss, Peter

    2015-01-01

    Emamectin benzoate, an insecticide derived from the avermectin family of natural products, has a unique translocation behavior in trees when applied by tree micro injection (TMI), which can result in protection from insect pests (foliar and borers) for several years. Active ingredient imported into leaves was measured at the end of season in the fallen leaves of treated horse chestnut (Aesculus hippocastanum) trees. The dissipation of emamectin benzoate in these leaves seems to be biphasic and depends on the decomposition of the leaf. In compost piles, where decomposition of leaves was fastest, a cumulative emamectin benzoate degradation half-life time of 20 d was measured. In leaves immersed in water, where decomposition was much slower, the degradation half-life time was 94 d, and in leaves left on the ground in contact with soil, where decomposition was slowest, the degradation half-life time was 212 d. The biphasic decline and the correlation with leaf decomposition might be attributed to an extensive sorption of emamectin benzoate residues to leaf macromolecules. This may also explain why earthworms ingesting leaves from injected trees take up very little emamectin benzoate and excrete it with the feces. Furthermore, no emamectin benzoate was found in water containing decomposing leaves from injected trees. It is concluded, that emamectin benzoate present in abscised leaves from horse chestnut trees injected with the insecticide is not available to nontarget organisms present in soil or water bodies. Environ Toxicol Chem 2014;9999:1–6. © 2014 The Authors. Published 2014 SETAC PMID:25363584

  8. Photodegradation of emamectin benzoate and its influence on efficacy against the rice stem borer Chilo suppressalis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Emamectin benzoate is a novel insecticide with characteristics of translaminar movement into plant leaf tissue. The compound was derived from the avermectin family and improved with thermal stability, greater water solubility, and a broader spectrum of insecticidal activity than avermectin. To deter...

  9. Monitoring of diamondback moth (Lepidoptera: Plutellidae) resistance to spinosad, indoxacarb, and emamectin benzoate.

    PubMed

    Zhao, J Z; Collins, H L; Li, Y X; Mau, R F L; Thompson, G D; Hertlein, M; Andaloro, J T; Boykin, R; Shelton, A M

    2006-02-01

    Six to nine populations of the diamondback moth, Plutella xylostella (L.), were collected annually from fields of crucifer vegetables in the United States and Mexico from 2001 to 2004 for baseline susceptibility tests and resistance monitoring to spinosad, indoxacarb, and emamectin benzoate. A discriminating concentration for resistance monitoring to indoxacarb and emamectin benzoate was determined based on baseline data in 2001 and was used in the diagnostic assay for each population in 2002-2004 together with a discriminating concentration for spinosad determined previously. Most populations were susceptible to all three insecticides, but a population from Hawaii in 2003 showed high levels of resistance to indoxacarb. Instances of resistance to spinosad occurred in Hawaii (2000), Georgia (2001), and California (2002) as a consequence of a few years of extensive applications in each region. The collaborative monitoring program between university and industry scientists we discuss in this article has provided useful information to both parties as well as growers who use the products. These studies provide a baseline for developing a more effective resistance management program for diamondback moth.

  10. Tolerance and Efficacy of Emamectin Benzoate and Ivermectin for the Treatment of Pseudocapillaria tomentosa in Laboratory Zebrafish (Danio rerio)

    PubMed Central

    Collymore, Chereen; Watral, Virginia; White, Julie R.; Colvin, Michael E.; Rasmussen, Skye; Tolwani, Ravi J.

    2014-01-01

    Abstract Tolerance of adult zebrafish and efficacy of emamectin benzoate and ivermectin in eliminating Pseudocapillaria tomentosa infection were evaluated. In the tolerance study, behavioral changes, fecundity, histopathology, and mortality were evaluated for in-feed administration of emamectin (0.05, 0.10, and 0.25 mg/kg) and ivermectin (0.05 and 0.10 mg/kg). All doses of emamectin were well tolerated. Ivermectin 0.05 mg/kg administration resulted in mild behavioral changes and a transient decrease in fecundity. Ivermectin 0.10 mg/kg administration resulted in severe behavioral changes and some mortality. In the efficacy study, emamectin (0.05 and 0.25 mg/kg) and ivermectin (0.05 mg/kg) were evaluated for their efficacy in eliminating P. tomentosa infection. Emamectin reduced parasite burden in infected zebrafish, and ivermectin eliminated intestinal nematode infections. Despite a small margin of safety, ivermectin 0.05 mg/kg was effective at eliminating P. tomentosa infection in adult zebrafish. Higher doses or a longer course of treatment may be needed for complete elimination of P. tomentosa infection using emamectin. In this study, we propose two possible treatments for intestinal nematode infections in zebrafish. PMID:25237985

  11. Ameliorative effect of vitamin C against hepatotoxicity induced by emamectin benzoate in rats.

    PubMed

    Khaldoun Oularbi, H; Richeval, C; Lebaili, N; Zerrouki-Daoudi, N; Baha, M; Djennas, N; Allorge, D

    2016-07-26

    In the present study, we aimed to assess the potential protective effect of ascorbic acid (AA) against emamectin benzoate (EMB)-induced hepatotoxicity. For this purpose, biochemical, histopathological and analytical investigations were performed. Male Wistar rats were distributed into three groups, that is, a control group, an EMB group given 10 mg EMB/kg body weight (BW) by gavage and an EMB + AA group given 10 mg EMB/kg BW and vitamin C intraperitoneally (200 mg/kg). The duration of the treatment was 28 days and the duration of the study was 42 days. There was a statistically significant increase of all hepatic biomarkers, that is, aspartate aminotransferase, alanine aminotransferase and gamma-glutamyltransferase activities, and glycemia, in EMB-treated group when compared with the control group. Light microscopic observations revealed variable signs of hepatotoxicity in the EMB group, which were represented by alteration of normal hepatic architecture, inflammatory cell infiltration, hepatocellular steatosis and foci of necrosis at 28 and 42 days post-treatment. However, co-treatment with vitamin C reduced EMB-related liver toxicity and diminished the abnormal biochemical and architectural damage. Emamectin B1a and B1b residues were detectable in all plasma samples of treated rats at 14, 21 and 28 days of treatment. The drug liver tissue concentration was significantly lower in EMB + AA group compared with EMB group at 28 and 42 days. In conclusion, the findings of the present study clearly indicate a significant protective action of vitamin C against EMB hepatotoxicity.

  12. Induction and transmission of tolerance to the synthetic pesticide emamectin benzoate in field and laboratory populations of diamondback moth.

    PubMed

    Rahman, M M; Baker, G; Powis, K J; Roush, R T; Schmidt, O

    2010-08-01

    Field surveys of pest insect pest populations in agroecosystems reveal low but significant levels of tolerance to synthetic and biological pesticides but fail to uncover resistance alleles in test crosses. To study the potential of inducible mechanisms to generate tolerance to synthetic pesticides, we performed baseline susceptibility studies in field and laboratory populations of diamondback moth, Plutella xylostella (L.), to commercial formulations of emamectin benzoate. Pesticide exposure in the field caused elevated levels of tolerance, which decreased in field-collected populations after maintaining insects with pesticide-free diet in the laboratory. Because no significant resistance alleles were identified in back-crossed individuals, the observed increase in tolerance was probably not based on preexisting recessive resistance mechanisms in the population. Instead, the genetic analysis after five and 12 generations is compatible with a transient up-regulation of an immune and metabolic status in tolerant insects that can be transmitted to offspring by a maternal effect. Although the epigenetic effects contributed to incremental increases in tolerance in the first five generations, other resistance mechanisms that are transmitted genetically predominate after 12 generations of increased exposure to the pesticide.

  13. Transcriptomic responses to emamectin benzoate in Pacific and Atlantic Canada salmon lice Lepeophtheirus salmonis with differing levels of drug resistance

    PubMed Central

    Sutherland, Ben J G; Poley, Jordan D; Igboeli, Okechukwu O; Jantzen, Johanna R; Fast, Mark D; Koop, Ben F; Jones, Simon R M

    2015-01-01

    Salmon lice Lepeophtheirus salmonis are an ecologically and economically important parasite of wild and farmed salmon. In Scotland, Norway, and Eastern Canada, L. salmonis have developed resistance to emamectin benzoate (EMB), one of the few parasiticides available for salmon lice. Drug resistance mechanisms can be complex, potentially differing among populations and involving multiple genes with additive effects (i.e., polygenic resistance). Indicators of resistance development may enable early detection and countermeasures to avoid the spread of resistance. Here, we collect sensitive Pacific L. salmonis and sensitive and resistant Atlantic L. salmonis from salmon farms, propagate in laboratory (F1), expose to EMB in bioassays, and evaluate either baseline (Atlantic only) or induced transcriptomic differences between populations. In all populations, induced responses were minor and a cellular stress response was not identified. Pacific lice did not upregulate any genes in response to EMB, but downregulated degradative enzymes and transport proteins at 50 ppb EMB. Baseline differences between sensitive and now resistant Atlantic lice were much greater than responses to exposures. All resistant lice overexpressed degradative enzymes, and resistant males, the most resistant group, overexpressed collagenases to the greatest extent. These results indicate an accumulation of baseline expression differences related to resistance. PMID:25685190

  14. Consecutive emamectin benzoate and deltamethrin treatments affect the expressions and activities of detoxification enzymes in the rainbow trout (Oncorhynchus mykiss).

    PubMed

    Cárcamo, Juan Guillermo; Aguilar, Marcelo N; Carreño, Constanza F; Vera, Tamara; Arias-Darraz, Luis; Figueroa, Jaime E; Romero, Alex P; Alvarez, Marco; Yañez, Alejandro J

    2017-01-01

    Rainbow trout (Oncorhynchus mykiss) subjected to three consecutive, alternating treatments with emamectin benzoate (EMB) and deltamethrin (DM) during outbreaks of Caligus rogercresseyi in a farm located in southern Chile (Hornopiren, Chiloé), were studied to determine the effects of these treatments on the protein and enzymatic activity levels of cytochrome P450 1A (CYP1A), flavin-containing monooxygenase (FMO) and glutathione S-transferase (GST) in different tissues. Consecutive and alternating EMB/DM treatments resulted in a 10-fold increase and 3-fold decrease of CYP1A protein levels in the intestine and gills, respectively. Notably, CYP1A activity levels decreased in most of the analyzed tissues. FMO protein and activity levels markedly increased in the kidney and the intestine. GST was up-regulated in all tissues, either as protein or enzyme activity. When comparing consecutive EMB/DM treatments against previous studies of EMB treatment alone, CYP1A activity levels were similarly diminished, except in muscle. Likewise, FMO activity levels were increased in most of the analyzed tissues, particularly in the muscle, kidney, and intestine. The increases observed for GST were essentially unchanged between consecutive EMB/DM and EMB only treatments. These results indicate that consecutive EMB/DM treatments in rainbow trout induce the expression and activity of FMO and GST enzymes and decrease CYP1A activity. These altered activities of detoxification enzymes could generate imbalances in metabolic processes, synthesis, degradation of hormones and complications associated with drug interactions. It is especially important when analyzing possible effects of consecutive antiparasitic treatments on withholding periods and salmon farming yields.

  15. The Use of F2 Screening for Detection of Resistance to Emamectin Benzoate, Chlorantraniliprole, and Indoxacarb in Australian Populations of Helicoverpa armigera (Lepidoptera: Noctuidae).

    PubMed

    Bird, L J; Drynan, L J; Walker, P W

    2017-03-03

    The ability to effectively detect changes in susceptibility to insecticides is an integral component of resistance management strategies and is highly dependent upon precision of methods deployed. Between 2013 and 2016, F2 screens were performed for detection of resistance alleles in Helicoverpa armigera (Hübner) to emamectin benzoate, chlorantraniliprole, and indoxacarb in major cropping regions of eastern Australia. Resistance to emamectin benzoate was not detected. There were low but detectable levels of survival at discriminating concentrations of chlorantraniliprole and indoxacarb. Alleles conferring an advantage to chlorantraniliprole were present at a frequency of 0.0027 (95% CI 0.0012-0.0064; n = 1,817). Alleles conferring an advantage to indoxacarb were present at a frequency of 0.027 (95% CI 0.020-0.035; n = 1,863). Complementation tests for allelism in six of seven positive indoxacarb tests indicated that resistance was due to alleles present at the same locus. The majority (88%) of lines that tested positive for indoxacarb resistance deviated from a model of recessive inheritance. Pheromone-caught male moths contributed significantly greater numbers of F2 lines compared with moths derived from field-collected eggs or larvae. There was no difference in the detectability of indoxacarb resistance in F2 lines from pheromone-caught moths compared with moths derived from immature stages collected from the field and reared to adult under laboratory conditions. Therefore, we recommend the use of pheromone traps for sourcing insects for F2 screening as a more cost- and time-efficient alternative to traditional methods of sampling.

  16. Toxic effects of sub-chronic exposure of male albino rats to emamectin benzoate and possible ameliorative role of Foeniculum vulgare essential oil.

    PubMed

    El-Sheikh, El-Sayed A; Galal, Azza A A

    2015-05-01

    Emamectin benzoate (EB) is an avermectin insecticide used extensively in pest control on vegetable and field crops. Few studies have been done for evaluating adverse effects of EB. In the current study, we evaluated the toxic effects of EB on male rats and the possible ameliorative role of fennel essential oil (FEO). Thirty two male rats were randomly divided into 4 equal groups. All groups were treated orally with distilled water (control group), 0.5mlFEOkg(-1) BW (FEO group), 2.5mgEBkg(-1) BW (EB group), and 0.5mlFEOkg(-1) BW+2.5mgEBkg(-1) BW (FEO+EB group) for 28 days. The obtained results showed that EB treatment resulted in a significant decrease in body weight, body weight gain, RBC count, Hb concentration, % PCV, MCV and MCHC. Moreover, EB significantly decreased total leukocyte, lymphocyte, monocyte and platelet count but significantly increased granulocyte count. EB markedly decreased total protein, albumin, globulin, IgG and IgM concentrations with a significant increase in TNF-α secretion. EB had a negative impact on the liver as it significantly increased ALT, ALP, and MDA, while decreasing SOD activity. Regarding to the histopathological examination, EB treatment induced coagulative necrosis and blood vessels congestion of the liver in treated rats. Furthermore, it resulted in depletion and necrosis of the white pulp of the spleen in treated rats. The co-administration of FEO with EB, however, improved the majority of parameters studied, suggesting that FEO is an important substance in decreasing toxic effects of EB.

  17. Salmon lice (Lepeophtheirus salmonis) showing varying emamectin benzoate susceptibilities differ in neuronal acetylcholine receptor and GABA-gated chloride channel mRNA expression

    PubMed Central

    2013-01-01

    Background Caligid copepods, also called sea lice, are fish ectoparasites, some species of which cause significant problems in the mariculture of salmon, where the annual cost of infection is in excess of €300 million globally. At present, caligid control on farms is mainly achieved using medicinal treatments. However, the continued use of a restricted number of medicine actives potentially favours the development of drug resistance. Here, we report transcriptional changes in a laboratory strain of the caligid Lepeophtheirus salmonis (Krøyer, 1837) that is moderately (~7-fold) resistant to the avermectin compound emamectin benzoate (EMB), a component of the anti-salmon louse agent SLICE® (Merck Animal Health). Results Suppression subtractive hybridisation (SSH) was used to enrich transcripts differentially expressed between EMB-resistant (PT) and drug-susceptible (S) laboratory strains of L. salmonis. SSH libraries were subjected to 454 sequencing. Further L. salmonis transcript sequences were available as expressed sequence tags (EST) from GenBank. Contiguous sequences were generated from both SSH and EST sequences and annotated. Transcriptional responses in PT and S salmon lice were investigated using custom 15 K oligonucleotide microarrays designed using the above sequence resources. In the absence of EMB exposure, 359 targets differed in transcript abundance between the two strains, these genes being enriched for functions such as calcium ion binding, chitin metabolism and muscle structure. γ-aminobutyric acid (GABA)-gated chloride channel (GABA-Cl) and neuronal acetylcholine receptor (nAChR) subunits showed significantly lower transcript levels in PT lice compared to S lice. Using RT-qPCR, the decrease in mRNA levels was estimated at ~1.4-fold for GABA-Cl and ~2.8-fold for nAChR. Salmon lice from the PT strain showed few transcriptional responses following acute exposure (1 or 3 h) to 200 μg L-1 of EMB, a drug concentration tolerated by PT lice, but

  18. 78 FR 18504 - Emamectin Benzoate; Pesticide Tolerance

    Federal Register 2010, 2011, 2012, 2013, 2014

    2013-03-27

    ... evidence that avermectin B 1a binds to GABA A receptors and activates Cl\\-\\ flux into neurons (Refs. 2 and... of mammalian neurons and neural networks (i.e., changes in cellular excitability and altered network... chloride channel of cultured cerebellar granule neurons. Journal of Pharmacology and...

  19. Emamectin, a novel insecticide for controlling field crop pests.

    PubMed

    Ishaaya, Isaac; Kontsedalov, Svetlana; Horowitz, A Rami

    2002-11-01

    Emamectin is a macrocyclic lactone insecticide with low toxicity to non-target organisms and the environment, and is considered an important component in pest-management programmes for controlling field crop pests. It is a powerful compound for controlling the cotton bollworm Helicoverpa armigera (Hübner). A spray concentration of 25 mg AI litre-1 in a cotton field resulted in over 90% suppression of H armigera larvae up to day 28 after treatment, while similar mortality of the Egyptian cotton leafworm Spodoptera littoralis Boisduval, under the same conditions, was maintained for 3 days only. Emamectin is a potent compound for controlling the western flower thrips Frankliniella occidentalis (Pergande) under both laboratory and field conditions and its activity on adults was over 10-fold greater than that of abamectin. Spray concentrations of 10 and 50 mg AI litre-1 in Ageratum houstonianum Mill flowers resulted in total suppression of adults up to day 11 and of larvae up to day 20 after treatment. Under standard laboratory conditions, emamectin exhibits a considerable activity on the whitefly Bemisia tabaci (Gennadius) and the leafminer Liriomyza huidobrensis (Blanchard). Further studies are required to evaluate its potential activity on the latter pests under field conditions.

  20. Degradation of abamectin by newly isolated Stenotrophomonas maltophilia ZJB-14120 and characterization of its abamectin-tolerance mechanism.

    PubMed

    Wang, Yuan-Shan; Zheng, Xing-Chang; Hu, Qi-Wei; Zheng, Yu-Guo

    2015-06-01

    An abamectin (ABM)-degrading bacterium, Stenotrophomonas maltophilia ZJB-14120, was isolated and identified. This strain is capable of degrading 84.82% of ABM at an initial concentration of 200 mg/L over a 48 h incubation period. This strain showed efficient biodegradation ability (7.81 mg/L/h) to ABM and high tolerance (1000 mg/L) to all macrolides tested. In addition to ABM, emamectin, erythromycin and spiramycin can also be degraded by this strain. Modifications involving either reduction of the double bond between C22-C23 or replacement of the C25-group of ABM with a cyclohexyl group can completely inhibit biodegradation of ABM. The ABM-degrading capability of strain ZJB-14120 is likely to be intrinsic to its metabolism and could be inhibited by incubating with erythromycin, azithromycin, spiramycin or rifampicin. A new and successive degradation pathway was proposed based on metabolite analysis. Although there is evidence for metabolite inhibition, this strain has high ABM degradation activity and reusability. Further investigation showed that activated macrolide efflux pump(s) and an undetermined mechanism for regulating the intracellular ABM concentration are responsible for normal uptake of essential metabolites while pumping out excess harmful compounds. Strain ZJB-14120 may provide efficient treatment of water and soil contaminated by toxic levels of abamectin and emamectin.

  1. Toxicity of abamectin to cockroaches (Dictyoptera: Blattellidae, Blattidae).

    PubMed

    Koehler, P G; Atkinson, T H; Patterson, R S

    1991-12-01

    Abamectin was fed to German cockroaches, Blattella germanica (L.), in non-choice tests. LT50s and LC50s were estimated by probit analysis. The LT50s for the German cockroach ranged from 4.4 to 1.7 d for males, from 9.0 to 2.4 d for females, and from 4.4 to 1.6 d for nymphs for bait concentrations of abamectin between 0.0025 and 0.0500%. The LC50s of abamectin were 0.0110 and 0.0040% from males, 0.0240 and 0.0090% for females, and 0.0200 and 0.0080% for nymphs at 3 and 6 d, respectively. The LT50 values of 0.0550% abamectin bait were 3.4, 3.4, 2.4, 7.5, 2.9, and 4.5 d for Periplaneta americana (L.), P. fuliginosa (Serville), P. brunnea Burmeister, P. australasiae (F.), Blatta orientalis L., and Supella longipalpa (Serville). Although the bait was effective against various cockroach species, time to death for the larger species was longer than for the German cockroach. In preference tests in which male German cockroaches were allowed to feed on rat chow or abamectin bait, all died within 5 d of exposure to abamectin bait. Abamectin bait consumption was not significantly lower than that of untreated rat chow. Arena tests with 0.0550% abamectin bait resulted in 31-75% mortality of German cockroaches after 9 d, with most control being achieved by treating harborages with the bait. The hydramethylnon standard resulted in 65% mortality after 9 d.

  2. 21 CFR 184.1733 - Sodium benzoate.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Sodium benzoate. 184.1733 Section 184.1733 Food and... Substances Affirmed as GRAS § 184.1733 Sodium benzoate. (a) Sodium benzoate is the chemical benzoate of soda (C7H5NaO2), produced by the neutralization of benzoic acid with sodium bicarbonate, sodium carbonate,...

  3. 21 CFR 184.1733 - Sodium benzoate.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Sodium benzoate. 184.1733 Section 184.1733 Food... Specific Substances Affirmed as GRAS § 184.1733 Sodium benzoate. (a) Sodium benzoate is the chemical benzoate of soda (C7H5NaO2), produced by the neutralization of benzoic acid with sodium bicarbonate,...

  4. 21 CFR 184.1733 - Sodium benzoate.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Sodium benzoate. 184.1733 Section 184.1733 Food... GRAS § 184.1733 Sodium benzoate. (a) Sodium benzoate is the chemical benzoate of soda (C7H5NaO2), produced by the neutralization of benzoic acid with sodium bicarbonate, sodium carbonate, or...

  5. 21 CFR 184.1733 - Sodium benzoate.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Sodium benzoate. 184.1733 Section 184.1733 Food... Specific Substances Affirmed as GRAS § 184.1733 Sodium benzoate. (a) Sodium benzoate is the chemical benzoate of soda (C7H5NaO2), produced by the neutralization of benzoic acid with sodium bicarbonate,...

  6. 21 CFR 184.1733 - Sodium benzoate.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Sodium benzoate. 184.1733 Section 184.1733 Food... Specific Substances Affirmed as GRAS § 184.1733 Sodium benzoate. (a) Sodium benzoate is the chemical benzoate of soda (C7H5NaO2), produced by the neutralization of benzoic acid with sodium bicarbonate,...

  7. Toxicity of abamectin and doramectin to soil invertebrates.

    PubMed

    Kolar, Lucija; Kozuh Erzen, Nevenka; Hogerwerf, Lenny; van Gestel, Cornelis A M

    2008-01-01

    This study aimed at determining the toxicity of avermectins to soil invertebrates in soil and in faeces from recently treated sheep. Abamectin was more toxic than doramectin. In soil, earthworms (Eisenia andrei) were most affected with LC50s of 18 and 228 mg/kg dry soil, respectively, while LC50s were 67-111 and >300 mg/kg for springtails (Folsomia candida), isopods (Porcellio scaber) and enchytraeids (Enchytraeus crypticus). EC50s for the effect on reproduction of springtails and enchytraeids were 13 and 38 mg/kg, respectively for abamectin, and 42 and 170 mg/kg for doramectin. For earthworms, NOEC was 10 and 8.4 mg/kg for abamectin and doramectin effects on body weight. When exposed in faeces, springtails and enchytraeids gave LC50s and EC50s of 1.0-1.4 and 0.94-1.1 mg/kg dry faeces for abamectin and 2.2->2.4 mg/kg for doramectin. Earthworm reproduction was not affected. This study indicates a potential risk of avermectins for soil invertebrates colonizing faeces from recently treated sheep.

  8. Effect of emamectin benzoate on mortality, proboscis extension, gustation and reproduction of the corn earworm, Helicoverpa zea

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Newly emerged bollworm adults, Helicoverpa zea (Boddie) require carbohydrate source from plant exudates and nectars for reproduction. Adults actively seek such feeding sites upon eclosion in their natural habitat. We wanted to evaluate this nocturnal behavior of the bollworm for potential use as a p...

  9. 21 CFR 582.3733 - Sodium benzoate.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Sodium benzoate. 582.3733 Section 582.3733 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL....3733 Sodium benzoate. (a) Product. Sodium benzoate. (b) Tolerance. This substance is...

  10. 21 CFR 582.3733 - Sodium benzoate.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Sodium benzoate. 582.3733 Section 582.3733 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL....3733 Sodium benzoate. (a) Product. Sodium benzoate. (b) Tolerance. This substance is...

  11. 21 CFR 582.3733 - Sodium benzoate.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Sodium benzoate. 582.3733 Section 582.3733 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL....3733 Sodium benzoate. (a) Product. Sodium benzoate. (b) Tolerance. This substance is...

  12. 21 CFR 582.3733 - Sodium benzoate.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Sodium benzoate. 582.3733 Section 582.3733 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL....3733 Sodium benzoate. (a) Product. Sodium benzoate. (b) Tolerance. This substance is...

  13. 21 CFR 582.3733 - Sodium benzoate.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Sodium benzoate. 582.3733 Section 582.3733 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL....3733 Sodium benzoate. (a) Product. Sodium benzoate. (b) Tolerance. This substance is...

  14. Photodegradation of the acaricide abamectin: a kinetic study.

    PubMed

    Escalada, Juan Pablo; Gianotti, José; Pajares, Adriana; Massad, Walter A; Amat-Guerri, Francisco; García, Norman A

    2008-08-27

    The acaricide abamectin is a mixture of two colorless homologues in a molar ratio of at least 4:1 with the same structure of macrocyclic lactone. The kinetics of its degradation under direct (254 nm) and dye-sensitized (>400 nm) photoirradiation in methanol solution has been studied by UV-vis spectrophotometry, potentiometric detection of dissolved oxygen, stationary fluorescence, laser flash photolysis, and time-resolved detection of singlet molecular oxygen (O2((1)Delta(g))) phosphorescence. The results indicate that the degradation is very efficient under direct irradiation with UV light (254 nm), with a quantum yield of 0.23. On the contrary, under visible-light irradiation, using the natural pigment riboflavin or the synthetic dye rose bengal as sensitizers, the degradation is very inefficient and proceeds through a O2((1)Delta(g))-mediated mechanism, with a bimolecular rate constant for the overall O2((1)Delta(g)) quenching (the sum of physical and chemical quenching) of 5.5 x 10(5) M(-1) s(-1). This value is similar to those reported for the rate constants of the reactions of O2((1)Delta(g)) with isolated double bonds or conjugated dienes and points to similar processes in the case of abamectin.

  15. Protective effects of Eruca sativa (rocket) on abamectin insecticide toxicity in male albino rats.

    PubMed

    Meligi, Noha M; Hassan, Hanaa Fawzy

    2017-03-01

    The extensive use of insecticides has hazardous effects since they can damage human health as well as the environment. Abamectin has been widely used in veterinary medicine and as a pesticide in agriculture. It is considered as one of the most commonly used insecticides in Egypt. The focus of the present study is to examine the toxic effects of sublethal dose (1 mg/kg b.wt.) of abamectin (Crater 3.37% EC) in male albino rats and to evaluate the efficiency of Eruca sativa suspension to ameliorate the abamectin toxicity. The present study was achieved using 18 male albino rats. Rats were divided into three groups: normal control group, abamectin-treated group, and abamectin + E. sativa-treated group. Rats of the third group were orally administrated a mixture of sublethal dose of abamectin (1 mg/kg b.wt.) and E. sativa suspension (5 g/kg b.wt.) three times a week for 28 days. At the end of the study period, blood samples were collected from all groups to measure the various hematological and biochemical parameters. The results revealed that rats, after abamectin exposure, exhibited general signs of toxicity and disturbance in the hematological and biochemical parameters. In addition, administration of E. sativa suspension ameliorated the hematological and biochemical parameters. These findings suggested that the exposure to abamectin might be responsible for hypertension, liver and kidney dysfunction, lipid profile disturbance, and oxidative stress, reflected in hematological and biochemical parameters. It was also found that the administration of E. sativa suspension reduced the detrimental impact of abamectin on some hematological and biochemical parameters.

  16. Potential of foliar, dip, and injection applications of avermectins for control of plant-parasitic nematodes.

    PubMed

    Jansson, R K; Rabatin, S

    1998-03-01

    Studies were conducted to determine the potential of two avermectin compounds, abamectin and emamectin benzoate, for controlling plant-parasitic nematodes when applied by three methods: foliar spray, root dip, and pseudostem injection. Experiments were conducted against Meloidogyne incognita on tomato, M. javanica on banana, and Radopholus similis on banana. Foliar applications of both avermectins to banana and tomato were not effective for controlling any of the nematodes evaluated. Root dips of banana and tomato were moderately effective for controlling M. incognita on tomato and R. similis on banana. Injections (1 ml) of avermectins into banana pseudostems were effective for controlling M. javanica and R similis, and were comparable to control achieved with a conventional chemical nematicide, fenamiphos. Injections of 125 to 2,000 mug/plant effectively controlled one or both nematodes on banana; abamectin was more effective than emamectin benzoate for controlling nematodes.

  17. Potential of Foliar, Dip, and Injection Applications of Avermectins for Control of Plant-Parasitic Nematodes

    PubMed Central

    Jansson, Richard K.; Rabatin, Susan

    1998-01-01

    Studies were conducted to determine the potential of two avermectin compounds, abamectin and emamectin benzoate, for controlling plant-parasitic nematodes when applied by three methods: foliar spray, root dip, and pseudostem injection. Experiments were conducted against Meloidogyne incognita on tomato, M. javanica on banana, and Radopholus similis on banana. Foliar applications of both avermectins to banana and tomato were not effective for controlling any of the nematodes evaluated. Root dips of banana and tomato were moderately effective for controlling M. incognita on tomato and R. similis on banana. Injections (1 ml) of avermectins into banana pseudostems were effective for controlling M. javanica and R similis, and were comparable to control achieved with a conventional chemical nematicide, fenamiphos. Injections of 125 to 2,000 μg/plant effectively controlled one or both nematodes on banana; abamectin was more effective than emamectin benzoate for controlling nematodes. PMID:19274200

  18. Chemotaxis of Pseudomonas putida toward chlorinated benzoates

    SciTech Connect

    Harwood, C.S.; Parales, R.E.; Dispensa, M. )

    1990-05-01

    The chlorinated aromatic acids 3-chlorobenzoate and 4-chlorobenzoate are chemoattractants for Pseudomonas putida PRS2000. These compounds are detected by a chromosomally encoded chemotactic response to benzoate which is inducible by {beta}-ketoadipate, and intermediate of benzoate catabolism. Plasmid pAC27, encoding enzymes for 3-chlorobenzoate degradation, does not appear to carry genes for chemotaxis toward chlorinated compounds.

  19. Toxicity of abamectin to the terrestrial isopod Porcellio scaber (Isopoda, Crustacea).

    PubMed

    Kolar, Lucija; Jemec, Anita; van Gestel, Cornelis A M; Valant, Janez; Hrzenjak, Rok; Erzen, Nevenka Kozuh; Zidar, Primoz

    2010-06-01

    To determine effects of the antiparasitic veterinary drug abamectin on the isopod Porcellio scaber, animals were exposed for 21 days to Lufa 2.2 soil spiked at concentrations of 3-300 mg/kg dry soil. After exposure, abamectin residues in the isopods were analysed using a novel analytical method. Toxicity was evaluated on different levels of biological organisation: biochemical, cellular and the individual organism. Measurements included glutathione S-transferase (GST) activity and stability of cell membranes in the digestive gland, animal mass gain or loss, food consumption, behaviour and mortality. LC50 for the effect of abamectin on survival of P. scaber was 71 mg/kg dry soil. The most obvious sublethal effects were reduced food consumption and decreased body mass (NOEC 3 mg/kg dry soil). Additionally, loss of digging activity and reduced GST activity (NOEC 30 mg/kg dry soil) and cell membrane destabilization (NOEC 10 mg/kg dry soil) were recorded. Abamectin only slightly accumulated in the isopods, with bioaccumulation factors always being <0.1. Based on these results and current information on environmental levels of abamectin, it is not likely that isopods will be affected by abamectin, but further studies with exposure through faeces are recommended.

  20. Evidence for an anaerobic syntrophic benzoate degradation threshold and isolation of the syntrophic benzoate degrader

    SciTech Connect

    Hopkins, B.T.; McInerney, M.J.; Warikoo, V.

    1995-02-01

    An anaerobic, motile, gram-negative, rod-shaped, syntrophic. benzoate-degrading bacterium, strain SB. was isolated in pure culture with crotonate as the energy source. Benzoate was degraded only in association with an H{sub 2}-using bacterium. The kinetics of benzoate degradation by cell suspensions of strain SB in coculture with Desulfovibrio strain G-11 was studied by using progress curve analysis. The coculture degraded benzoate to a threshold concentration of 214 nM to 6.5 {mu}M, with no further benzoate degradation observed even after extended incubation times. The value of the threshold depended on the amount of benzoate added and, consequently, the amount of acetate produced. The addition of sodium acetate. but not that of sodium chloride, affected the threshold value; higher acetate concentrations resulted in higher threshold values for benzoate. When a cell suspension that had reached a threshold benzoate concentration was reamended with benzoate, benzoate was used without a lag. The hydrogen partial pressure was very low and formate was not detected in cell suspensions that had degraded benzoate to a threshold value. The Gibbs free energy change calculations showed that the degradation of benzoate was favorable when the threshold was reached. These studies showed that the threshold for benzoate degradation was not caused by nutritional limitations. the loss of metabolic activity, or inhibition by hydrogen or formate. The data are consistent with a thermodynamic explanation for the existence of a threshold, but a kinetic explanation based on acetate inhibition may also account for the existence of a threshold.

  1. Construction and evaluation of controlled-release delivery system of Abamectin using porous silica nanoparticles as carriers

    NASA Astrophysics Data System (ADS)

    Wang, Yan; Cui, Haixin; Sun, Changjiao; Zhao, Xiang; Cui, Bo

    2014-12-01

    Photolysis and poor solubility in water of Abamectin are key issues to be addressed, which causes low bioavailability and residual pollution. In this study, a novel hydrophilic delivery system through loading Abamectin with porous silica nanoparticles (Abam-PSNs) was developed in order to improve the chemical stability, dispersity, and the controlled release of Abamectin. These results suggest that Abam-PSNs can significantly improve the performance of controllable release, photostability, and water solubility of Abamectin by changing the porous structure of silica nanoparticles, which is favorable to improve the bioavailability and reduce the residues of pesticides.

  2. Evaluation of the effectiveness of insecticide trunk injections for control of Latoia lepida (Cramer) in the sweet olive tree Osmanthus fragrans.

    PubMed

    Huang, Jun; Zhang, Juan; Li, Yan; Li, Jun; Shi, Xiao-Hua

    2016-01-01

    The screening of suitable insecticides is a key factor in successfully applying trunk injection technology to ornamental plants. In this study, six chemical pesticides were selected and injected into the trunks of Osmanthus fragrans to control the nettle caterpillar, Latoia lepida (Lepidoptera: Limacodidae), using a no-pressure injection system. The absorption rate of the insecticides, the leaf loss due to insect damage, and the mortality and frass amount of L. lepida larvae were evaluated after 77 and 429 days. The results showed that 4% imidacloprid + carbosulfan and 21% abamectin + imidacloprid + omethoate had the fastest conductivity and were completely absorbed into the trunkswithin14 days; however, the efficiencies of these insecticides in controlling L. lepidawere extremely low. Additionally, the treatment 10% emamectin benzoate + clothianidin and 2.5% emamectin benzoate was almost completely absorbed within 30 days and exhibited a longer duration of insecticide efficiency (>80% mortality) in the upper and lower leaves of the canopy. Treatment with these insecticides also resulted in significantly lower leaf loss and frass amounts. We conclude that emamectin benzoate and emamectin benzoate + clothianidin have a rapid uptake into O. fragrans, and are effective as insecticides over long durations. Hence, they may be a suitable control option for L. lepida in O. fragrans plants.

  3. Evaluation of the effectiveness of insecticide trunk injections for control of Latoia lepida (Cramer) in the sweet olive tree Osmanthus fragrans

    PubMed Central

    Li, Yan; Shi, Xiao-Hua

    2016-01-01

    The screening of suitable insecticides is a key factor in successfully applying trunk injection technology to ornamental plants. In this study, six chemical pesticides were selected and injected into the trunks of Osmanthus fragrans to control the nettle caterpillar, Latoia lepida (Lepidoptera: Limacodidae), using a no-pressure injection system. The absorption rate of the insecticides, the leaf loss due to insect damage, and the mortality and frass amount of L. lepida larvae were evaluated after 77 and 429 days. The results showed that 4% imidacloprid + carbosulfan and 21% abamectin + imidacloprid + omethoate had the fastest conductivity and were completely absorbed into the trunkswithin14 days; however, the efficiencies of these insecticides in controlling L. lepidawere extremely low. Additionally, the treatment 10% emamectin benzoate + clothianidin and 2.5% emamectin benzoate was almost completely absorbed within 30 days and exhibited a longer duration of insecticide efficiency (>80% mortality) in the upper and lower leaves of the canopy. Treatment with these insecticides also resulted in significantly lower leaf loss and frass amounts. We conclude that emamectin benzoate and emamectin benzoate + clothianidin have a rapid uptake into O. fragrans, and are effective as insecticides over long durations. Hence, they may be a suitable control option for L. lepida in O. fragrans plants. PMID:27688974

  4. In vitro dermal disposition of abamectin (avermectin B(1)) in livestock.

    PubMed

    Baynes, Ronald E

    2004-06-01

    Many avermectins are approved for topical application in domestic animals. However, extralabel use may result in significant dermal absorption and consequently the potential for adverse effects or violative residues. The primary aim of this study was to assess dermal disposition of abamectin in vitro in bovine, caprine, ovine, and porcine skin dosed in 100% isopropanol, commercial alcohol-based (Ivomec), or oil-based (Eprinex) formulations. Skin sections were perfused in a flow-through diffusion cell system for 8 h, and the disposition of radiolabel abamectin was determined from perfusate and skin samples. Abamectin absorption ranged from 0.09% to 0.20% dose and there were no significant differences between formulations in each species. Isopropanol significantly increased skin deposition in all species when compared to the oil formulation. Absorption was significantly greater in bovine skin than in porcine skin for the isopropanol-containing formulations, but there were no significant species differences for the oil formulation. While significant levels (11.69-50.23% dose) remained on the skin surface, the highest levels deposited in viable skin were observed in caprine skin (28.09% dose) and the lowest levels were in porcine skin (1.50% dose) which could lead to systemic absorption. In summary, these 8-h experiments demonstrated that the alcohol-based formulations compared to oil-based formulations enhanced abamectin absorption and skin deposition in several animal species, and this effect is more likely to be observed in ruminant species than in porcine species.

  5. 21 CFR 522.1940 - Progesterone and estradiol benzoate.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...: (1) Suckling beef calves—(i) Amount—(A) 100 milligrams (mg) progesterone and 10 mg estradiol benzoate (one implant consisting of 4 pellets, each pellet containing 25 mg progesterone and 2.5 mg estradiol benzoate) per implant dose. (B) 100 mg progesterone and 10 mg estradiol benzoate (one implant consisting...

  6. Catabolism of benzoate and monohydroxylated benzoates by Amycolatopsis and Streptomyces spp

    SciTech Connect

    Grund, E.; Knorr, C.; Eichenlaub, R. )

    1990-05-01

    Eight actinomycetes of the genera Amycolatopsis and Streptomyces were tested for the degradation of aromatic compounds by growth in a liquid medium containing benzoate, monohydroxylated benzoates, or quinate as the principal carbon source. Benzoate was converted to catechol. The key intermediate in the degradation of salicylate was either catechol or gentisate, while m-hydroxybenzoate was metabolized via gentisate or protocatechuate. p-Hydroxybenzoate and quinate were converted to protocatechuate. Catechol, gentisate, and protocatechuate were cleaved catechol 1,2-dioxygenase, gentisate 1,2-dioxygenase, and protocatechuate 3,4-dioxygenase, respectively. The requirement for glutathione in the gentisate pathway was dependent on the substrate and the particular strain. The conversion of p-hydroxybenzoate to protocatechuate by p-hydroxybenzoate hydroxylase was gratuitously induced by all substrates that were metabolized via protocatechuate as an intermediate, while protocatechuate 3,4-dioxygenase was gratuitously induced by benzoate and salicylate in two Amycolatopsis strains.

  7. A point mutation in the glutamate-gated chloride channel of Plutella xylostella is associated with resistance to abamectin.

    PubMed

    Wang, X; Wang, R; Yang, Y; Wu, S; O'Reilly, A O; Wu, Y

    2016-04-01

    The diamondback moth, Plutella xylostella, is a global pest of cruciferous vegetables. Abamectin resistance in a field population of P. xylostella was introgressed into the susceptible Roth strain. The resulting introgression strain Roth-Abm showed 11 000-fold resistance to abamectin compared with Roth. An A309V substitution at the N-terminus of the third transmembrane helix (M3) of the glutamate-gated chloride channel of P. xylostella (PxGluCl) was identified in Roth-Abm. The frequency of the V309 allele of PxGluCl was 94.7% in Roth-Abm, whereas no such allele was detected in Roth. A subpopulation of Roth-Abm was kept without abamectin selection for 20 generations to produce a revertant strain, Roth-Abm-D. Abamectin resistance in Roth-Abm-D declined to 1150-fold compared with Roth, with the V309 allele frequency decreased to 9.6%. After treatment of the Roth-Abm-D strain with 80 mg/l abamectin the V309 allele frequency in the survivors increased to 55%. This demonstrates that the A309V mutation in PxGluCl is strongly associated with a 10-fold increase in abamectin resistance in Roth-Abm relative to Roth-Abm-D. Homology modelling and automated ligand docking results suggest that the A309V substitution allosterically modifies the abamectin-binding site, as opposed to directly eliminating a key binding contact. Other resistance mechanisms to abamectin in Roth-Abm are discussed besides the A309V mutation of PxGluCl.

  8. Determination of abamectin residues in fruits and vegetables by high-performance liquid chromatography.

    PubMed

    Diserens, H; Henzelin, M

    1999-02-12

    A rapid and sensitive HPLC method has been developed and validated for the determination of abamectin residues (avermectin B1a and B1b, as well as the metabolite 8,9-Z-avermectin B1) in apples, pears and tomatoes. Residues are extracted with acetonitrile. The diluted extract is cleaned up on a C18 solid-phase extraction cartridge. Abamectin residues are derivatised with trifluoroacetic acid and 1-methylimidazole and determined by reversed-phase liquid chromatography with fluorescence detection (excitation: 365 nm and emission: 470 nm). High and consistent recoveries, ranging from 88 to 106%, were obtained, at spiking levels of 10, 20 and 50 micrograms/kg, when analysing apples, pears and tomatoes.

  9. Cytotoxic and genotoxic effects of abamectin, chlorfenapyr, and imidacloprid on CHOK1 cells.

    PubMed

    Al-Sarar, Ali S; Abobakr, Yasser; Bayoumi, Alaa E; Hussein, Hamdy I

    2015-11-01

    The cytotoxicity and genotoxicity of abamectin, chlorfenapyr, and imidacloprid have been evaluated on the Chinese hamster ovary (CHOK1) cells. Neutral red incorporation (NRI), total cellular protein content (TCP), and methyl tetrazolium (MTT) assays were followed to estimate the mid-point cytotoxicity values, NRI50, TCP50, and MTT50, respectively. The effects of the sublethal concentration (NRI25) on glutathione S-transferase (GST), glutathione reductase (GRD), glutathione peroxidase (GPX), and total glutathione content have been evaluated in the presence and absence of reduced glutathione (GSH), vitamin C, and vitamin E. The genotoxicity was evaluated using chromosomal aberrations (CA), micronucleus (MN) formation, and DNA fragmentation techniques in the presence and absence of the metabolic activation system, S9 mix. Abamectin was the most cytotoxic pesticide followed by chlorfenapyr, while imidacloprid was the least cytotoxic one. The glutathione redox cycle components were altered by the tested pesticides in the absence and presence of the tested antioxidants. The results of genotoxicity indicate that abamectin, chlorfenapyr, and imidacloprid have potential genotoxic effects on CHOK1 cells under the experimental conditions.

  10. Neuro and renal toxicity induced by chlorpyrifos and abamectin in rats: Toxicity of insecticide mixture.

    PubMed

    Nasr, Hoda M; El-Demerdash, Fatma M; El-Nagar, Wael A

    2016-01-01

    Oxidative stress by increased production of reactive oxygen species has been implicated in pesticides toxicity. This study focused on the toxicological effects of chlorpyrifos, an organophosphate insecticide and abamectin, a biocide each alone or in combination on antioxidant status, and oxidative stress biomarkers in brain and kidney. Animals were divided into four groups. The first group was used as control while groups 2, 3, and 4 were treated with chlorpyrifos (CPF; 14.9 mg/kg BW), abamectin (ABM; 30 mg/kg BW), and chlorpyrifos plus abamectin, respectively. Rats were treated daily with the tested compounds by oral gavages for 30 days. Results revealed that thiobarbituric acid-reactive substances (TBARS) levels were significantly increased in brain and kidney due to insecticides administration. On the other hand, reduced glutathione (GSH) and protein contents in addition to the activities of antioxidant enzymes, alkaline phosphatase (ALP), and acetylcholinesterase (AChE) were significantly decreased in rat organs. A significant induction in lactate dehydrogenase (LDH) activity, urea, and creatinine levels were also observed. The response was more pronounced in rats treated with both CPF and ABM. Results showed that the used insecticides had the propensity to cause significant oxidative damage in rat brain and kidney which is associated with marked perturbations in antioxidant defense system. It can be concluded that antioxidant enzymes can be used as potential biomarkers of toxicity associated with pesticides exposure.

  11. Haematological, biochemical and histopathological alterations induced by abamectin and Bacillus thuringiensis in male albino rats.

    PubMed

    Eissa, F I; Zidan, N A

    2010-03-01

    The renal- and hepato-toxicity induced by abamectin pesticide (Vertimec) and a commercial form of a bio-insecticide Bacillus thuringiensis (Agerin) in male albino rats were evaluated. Blood picture and blood glucose level were investigated. Male albino rats were administered dietary doses each equivalent to 1/10 or 1/100 of the LD50 values of each toxicant for 30 consecutive days. Abamectin was found to pose risks of renal- and hepato-toxicity in rats, since the biochemical parameters of liver function (i.e. aspartate aminotransferase activity, alanine aminotransferase activity, acid phosphatase activity, albumin, and total protein levels) and kidney function (uric acid and creatinine concentration) were severely affected. These effects were verified by histopathological examination of liver and kidney tissues. Likewise, some haematological indices (i.e. erythrocyte count, leukocyte count and haemoglobin concentration) were also influenced; in addition abamectin might cause hypoglycaemia. On the other hand, the above-mentioned lesions were less pronounced in the case of Bacillus thuringiensis -treated rats.

  12. Insecticidal efficacy of abamectin against three stored-product insect pests: influence of dose rate, temperature, commodity, and exposure interval.

    PubMed

    Kavallieratos, Nickolas G; Athanassiou, Christos G; Vayias, Basileios J; Mihail, Spyridon B; Tomanović, Zeljko

    2009-06-01

    The insecticidal efficacy of abamectin against adults of Rhyzopertha dominica (F.), Sitophilus oryzae (L.), and Tribolium confusum Jacquelin du Val was assessed under laboratory conditions. The efficacy of abamectin was assessed on two commodities (wheat, Triticum aestivum L. and maize, Zea mays L.) and two temperatures (25 and 30 degrees C). The dose rates used were 0.01, 0.1, 0.5, and 1 ppm. Mortality of the exposed adults in the treated grains was measured after 7, 14 and 21 d (= days), whereas progeny production was assessed 60 d later. Increase of dose rate, exposure interval, and temperature enhanced the efficacy of abamectin. Noticeable mortality was noted for all species after 21 d of exposure, although for S. oryzae, mortality was very high even at 7 d. For dose rates higher than 0.5 ppm, the efficacy of abamectin was higher in maize than in wheat against all species tested. Finally, progeny production was measured for all three species on commodities treated with 0.01 and 0.1 ppm of abamectin.

  13. 21 CFR 522.1940 - Progesterone and estradiol benzoate.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Progesterone and estradiol benzoate. 522.1940... § 522.1940 Progesterone and estradiol benzoate. (a) Sponsors. See sponsors in § 510.600(c) of this...: (1) Suckling beef calves—(i) Amount—(A) 100 milligrams (mg) progesterone and 10 mg estradiol...

  14. 21 CFR 522.1940 - Progesterone and estradiol benzoate.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Progesterone and estradiol benzoate. 522.1940... § 522.1940 Progesterone and estradiol benzoate. (a) Sponsors. See sponsors in § 510.600(c) of this...: (1) Suckling beef calves—(i) Amount—(A) 100 milligrams (mg) progesterone and 10 mg estradiol...

  15. 21 CFR 522.1940 - Progesterone and estradiol benzoate.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Progesterone and estradiol benzoate. 522.1940... § 522.1940 Progesterone and estradiol benzoate. (a) Sponsors. See sponsors in § 510.600(c) of this...: (1) Suckling beef calves—(i) Amount—(A) 100 milligrams (mg) progesterone and 10 mg estradiol...

  16. Curiouser and Curiouser: The Macrocyclic Lactone, Abamectin, Is also a Potent Inhibitor of Pyrantel/Tribendimidine Nicotinic Acetylcholine Receptors of Gastro-Intestinal Worms.

    PubMed

    Abongwa, Melanie; Buxton, Samuel K; Robertson, Alan P; Martin, Richard J

    2016-01-01

    Nematode parasites may be controlled with drugs, but their regular application has given rise to concerns about the development of resistance. Drug combinations may be more effective than single drugs and delay the onset of resistance. A combination of the nicotinic antagonist, derquantel, and the macrocyclic lactone, abamectin, has been found to have synergistic anthelmintic effects against gastro-intestinal nematode parasites. We have observed in previous contraction and electrophysiological experiments that derquantel is a potent selective antagonist of nematode parasite muscle nicotinic receptors; and that abamectin is an inhibitor of the same nicotinic receptors. To explore these inhibitory effects further, we expressed muscle nicotinic receptors of the nodular worm, Oesophagostomum dentatum (Ode-UNC-29:Ode-UNC-63:Ode-UNC-38), in Xenopus oocytes under voltage-clamp and tested effects of abamectin on pyrantel and acetylcholine responses. The receptors were antagonized by 0.03 μM abamectin in a non-competitive manner (reduced Rmax, no change in EC50). This antagonism increased when abamectin was increased to 0.1 μM. However, when we increased the concentration of abamectin further to 0.3 μM, 1 μM or 10 μM, we found that the antagonism decreased and was less than with 0.1 μM abamectin. The bi-phasic effects of abamectin suggest that abamectin acts at two allosteric sites: one high affinity negative allosteric (NAM) site causing antagonism, and another lower affinity positive allosteric (PAM) site causing a reduction in antagonism. We also tested the effects of 0.1 μM derquantel alone and in combination with 0.3 μM abamectin. We found that derquantel on these receptors, like abamectin, acted as a non-competitive antagonist, and that the combination of derquantel and abamectin produced greater inhibition. These observations confirm the antagonistic effects of abamectin on nematode nicotinic receptors in addition to GluCl effects, and illustrate more complex

  17. Endectocide activity of a pour-on formulation containing 1.5 per cent ivermectin +0.5 per cent abamectin in cattle

    PubMed Central

    Silva, Heloisa Cristina; Prette, Nancy; Lopes, Welber Daniel Zanetti; Sakamoto, Cláudio Alessandro M; Buzzulini, Carolina; dos Santos, Thais Rabelo; Cruz, Breno Cayeiro; Teixeira, Weslen F Pires; Felippelli, Gustavo; Carvalho, Rafael Silveira; Maciel, Willian Giquelin; Soares, Vando Edésio; da Costa, Alvimar José

    2015-01-01

    The present work aimed to evaluate, through ten different studies, the therapeutic efficacy of a new pour-on formulation, containing 1.5 per cent ivermectin +0.5 per cent abamectin, against parasites of cattle. Results obtained on trials against Rhipicephalus (Boophilus) microplus showed that the pour-on combination of 1.5 per cent ivermectin +0.5 per cent abamectin obtained superior efficacy indexes against this ectoparasite, when compared with formulations containing 0.5 per cent ivermectin, 1 per cent ivermectin and the combination of 1 per cent abamectin +20 per cent levamisole. The results of efficacy of the ivermectin+abamectin and the 0.5 per cent ivermectin against Haematobia irritans were similar. Against Cochliomyia hominivorax larvae, all pour-on formulations tested (1.5 per cent ivermectin +0.5 per cent abamectin, 0.5 per cent ivermectin and 0.5 per cent abamectin), as well as 1 per cent doramectin administered subcutaneously, were considered ineffective. Cattle medicated with 1.5 per cent ivermectin +0.5 per cent abamectin, pour-on, remained free from parasitism by Dermatobia hominis larvae during 42 days (96 per cent efficacy), while values superior to 90 per cent were obtained by 0.5 per cent ivermectin (92 per cent) and 0.5 per cent abamectin (93 per cent) until the 42nd and 35th days post treatment, respectively. Against Haemonchus placei and Oesophagostomum radiatum, the pour-on of ivermectin+abamectin showed better efficacy than the 0.5 per cent ivermectin and 0.5 per cent abamectin. As to Cooperia punctata, there was no difference regarding efficacy results obtained by the avermectins combination and abamectin. The pour-on combination of 1.5 per cent ivermectin +0.5 per cent abamectin obtained high efficacy against R. (B.) microplus, D. hominis and some species of cattle gastrointestinal helminths when compared with formulations of 0.5 per cent ivermectin and 0.5 per cent abamectin administered through the same route. PMID:26392893

  18. Eco-toxicological effects of the avermectin family with a focus on abamectin and ivermectin.

    PubMed

    Bai, Shahla Hosseini; Ogbourne, Steven

    2016-07-01

    Avermectin family members are categorised as highly effective but toxic natural products that are used as pharmaceuticals in both humans and animals and for crop protection. Abamectin and ivermectin are the two most commonly used compounds from this family with abamectin the only compound to be used for both crop protection and pharmaceutical purposes. Avermectins are produced by the soil dwelling actinomycetes Streptomyces avermitilis and despite having complex chemical structures, they are manufactured via synthesis in large scales for commercial use. Although the extent of the eco-toxicological effects of avermectins is not well documented, reports of eco-toxicity exist. Avermectins have short half-lives and their residues can be eliminated through different food processing methods. However, avermectins can persist in water, sediment, soil and food products and therefore management practices that reduce the potential risks associated with eco-toxicity of these highly toxic compounds need to be further developed. This manuscript provides a critical review of the eco-toxicological risks and the potential for food contamination associated with avermectin use.

  19. Discovery of berberine, abamectin and ivermectin as antivirals against chikungunya and other alphaviruses.

    PubMed

    Varghese, Finny S; Kaukinen, Pasi; Gläsker, Sabine; Bespalov, Maxim; Hanski, Leena; Wennerberg, Krister; Kümmerer, Beate M; Ahola, Tero

    2016-02-01

    Chikungunya virus (CHIKV) is an arthritogenic arbovirus of the Alphavirus genus, which has infected millions of people after its re-emergence in the last decade. In this study, a BHK cell line containing a stable CHIKV replicon with a luciferase reporter was used in a high-throughput platform to screen approximately 3000 compounds. Following initial validation, 25 compounds were chosen as primary hits for secondary validation with wild type and reporter CHIKV infection, which identified three promising compounds. Abamectin (EC50 = 1.5 μM) and ivermectin (EC50 = 0.6 μM) are fermentation products generated by a soil dwelling actinomycete, Streptomyces avermitilis, whereas berberine (EC50 = 1.8 μM) is a plant-derived isoquinoline alkaloid. They inhibited CHIKV replication in a dose-dependent manner and had broad antiviral activity against other alphaviruses--Semliki Forest virus and Sindbis virus. Abamectin and ivermectin were also active against yellow fever virus, a flavivirus. These compounds caused reduced synthesis of CHIKV genomic and antigenomic viral RNA as well as downregulation of viral protein expression. Time of addition experiments also suggested that they act on the replication phase of the viral infectious cycle.

  20. Acetate inhibition of methanogenic, syntrophic benzoate degradation. [Methanospirillum

    SciTech Connect

    Dolfing, J.; Tiedje, J.M.

    1988-07-01

    Acetate inhibited benzoate degradation by a syntrophic coculture of an anaerobic benzoate degrader (strain BZ-2) and Methanospirillum strain PM-1; the apparent K/sub i/ for acetate was approximately 40 mM. The addition of acetate resulted in a decrease in the hydrogen concentration in the coculture, indicating that phenomena related to interspecies hydrogen transfer affected this value and that the effect of acetate on the benzoate-degrading partner was probably greater than the apparent K/sub i/ for the coculture suggests.

  1. Testing Spirotetramat as an Alternative Solution to Abamectin for Cacopsylla pyri (Hemiptera: Psyllidae) Control: Laboratory and Field Tests.

    PubMed

    Civolani, Stefano; Boselli, Mauro; Butturini, Alda; Chicca, Milvia; Cassanelli, Stefano; Tommasini, Maria Grazia; Aschonitis, Vassilis; Fano, Elisa Anna

    2015-12-01

    Aim of the study was to investigate the performance of the new insecticide "spirotetramat" as an alternative solution of "abamectin" for the control of Cacopsylla pyri L. (Hemiptera: Psyllidae) in the context of an IPM program in European pear, Pyrus communis L.. Laboratory bioassays for the estimation of LC50 and LC90 of both insecticides were performed using four populations collected in Emilia-Romagna (Italy) orchards where different pest management strategies were used (organic, integrated, and conventional). The same populations were also analyzed for the main insecticide detoxifying activities in nymphs by spectrofluorimetric in vitro assays. The performance of the two insecticides was also tested on field on one population under integrated pest management conditions. The laboratory experiments showed that the LC90 of spirotetramat were lower than the highest field concentration allowed in Europe (172.80 mg AI liter(-1)) giving reassurance about the efficacy of the product. Concerning the abamectin, the laboratory bioassays did not show strong indications of resistance development of C. pyri populations of Emilia-Romagna. A similarity in enzyme detoxifying activity was observed in both insecticides indicating a general absence of a significant insecticide resistance. The field trial showed a high efficacy (>90 %) of spirotetramat on C. pyri already after 15 d from application, and it was significantly higher from abamectin. Overall, spirotetramat is one more choice for C. pyri control, as well as abamectin in order to minimize the risks of occurrence of insecticide resistance.

  2. Determination of abamectin in citrus fruits using SPE combined with dispersive liquid-liquid microextraction and HPLC-UV detection.

    PubMed

    Rezaee, Mohammad; Mashayekhi, Hossein Ali; Saleh, Abolfazl; Abdollahzadeh, Yaser; Naeeni, Mohammad Hosein; Fattahi, Nazir

    2013-08-01

    A new pretreatment method, SPE combined with dispersive liquid-liquid microextraction, was proposed for the determination of abamectin in citrus fruit samples for the first time. In this method, fruit samples were extracted by ultrasound-assisted extraction followed by SPE. Then, the SPE was used as a disperser solvent in the next dispersive liquid-liquid microextraction step for further purification and enrichment of abamectin. The effects of various parameters on the extraction efficiency of the proposed method were investigated and optimized. Good linearity of abamectin was obtained from 0.005 to 10.0 mg/kg for B1a and from 0.05 to 10.0 mg/kg for B1b with correlation coefficient (r(2)) of 0.998 for B1a and 0.991 for B1b, respectively. The LODs were 0.001 and 0.008 mg/kg (S/N = 3) for B1a and B1b, respectively. The relative recoveries at three spiked levels were ranged from 87 to 96% with the RSD less than 11% (n = 3). The method has been successfully applied to the determination of abamectin in citrus fruit samples.

  3. Safety assessment of alkyl benzoates as used in cosmetics.

    PubMed

    'Becker, Lillian C; Bergfeld, Wilma F; Belsito, Donald V; Hill, Ronald A; Klaassen, Curtis D; Liebler, Daniel; Marks, James G; Shank, Ronald C; Slaga, Thomas J; Snyder, Paul W; Andersen, F Alan

    2012-01-01

    The functions of alkyl benzoates in cosmetics include fragrance ingredients, skin-conditioning agents--emollient, skin-conditioning agents--miscellaneous, preservatives, solvents, and plasticizers. The Cosmetic Ingredient Review Expert Panel reviewed the relevant animal and human data and noted gaps in the available safety data for some of the alkyl benzoates. Similar structure activity relationships, biologic functions, and cosmetic product usage allowed the available data of many of the alkyl benzoates to be extended to the entire group. Carcinogenicity data were not available, but available data indicated that these alkyl benzoate cosmetic ingredients are not genotoxic. Also benzoic acid and tested component alcohols were not reproductive or developmental toxicants, are not genotoxic in almost all assays, and are not carcinogenic. These ingredients were determined to be safe in the present practices of use and concentration.

  4. Field efficacy and safety of an oral formulation of the novel combination anthelmintic, derquantel-abamectin, in sheep in New Zealand

    PubMed Central

    Little, PR; Hodge, A; Watson, TG; Seed, JA; Maeder, SJ

    2011-01-01

    AIM: To evaluate the efficacy and safety of the novel anthelmintic combination, derquantel-abamectin, against gastrointestinal nematode populations in sheep, under field-use conditions. METHODS: Controlled faecal egg count reduction tests (FECRT) were conducted in New Zealand in 14 trials, covering a range of geographic locations, farming enterprises, breeds, nematode populations, and anthelmintic-resistance profiles. Enrolled animals were naturally infected with mixed populations of gastrointestinal nematodes. All trials included a group treated with derquantel-abamectin, and a negative control group. Nine trials included additional groups each treated with a single- or dual-active oral reference anthelmintic, selected from albendazole, levamisole, albendazole-levamisole, ivermectin, abamectin and moxidectin. A total of 838 animals were enrolled across all trials, and were randomly allocated to treatment groups within blocks defined by faecal nematode egg counts (FEC) pre-treatment. On Day 0 derquantel-abamectin was administered orally at 1 ml/5 kg bodyweight (2 mg/kg derquantel, 0.2 mg/ kg abamectin), and each reference anthelmintic was given at the recommended label dose. Faecal samples were collected on Day 14 (± 1 day), to determine the percentage reduction in mean FEC for each anthelmintic tested. Larval differentiation was also performed post-treatment, to estimate efficacy at the genus level. Animals were weighed on or before Day 0, and on Day 14 (± 1 day) in 13 trials. RESULTS: The efficacy of derquantel-abamectin against mixed strongyle populations was ≥99.2%, based on the percentage reduction in geometric mean FEC. Nematodirus sp. was present in six trials at a level sufficient for efficacy calculations to be conducted; in all cases, the efficacy of derquantel-abamectin was 100%. In those trials where the efficacy of at least one reference anthelmintic was <95% against strongyles and/or Nematodirus sp., derquantel-abamectin was 100% effective. In

  5. Abamectin is metabolized by CYP392A16, a cytochrome P450 associated with high levels of acaricide resistance in Tetranychus urticae.

    PubMed

    Riga, M; Tsakireli, D; Ilias, A; Morou, E; Myridakis, A; Stephanou, E G; Nauen, R; Dermauw, W; Van Leeuwen, T; Paine, M; Vontas, J

    2014-03-01

    Abamectin is one of the most important insecticides worldwide. It is used against major agricultural pests and insects of public health importance, as well as against endoparasites in animal health. Abamectin has been used successfully for the control of the spider mite Tetranychus urticae, a major agricultural pest with global distribution, an extremely diverse host range, and a remarkable ability to develop resistance against insecticides including abamectin. Target site resistance mutations may explain a large part of resistance, although genetic evidence and transcriptomic data indicated that additional mechanisms may also be implicated in the abamectin resistant phenotype. To investigate a functional link between cytochrome P450-mediated metabolism and abamectin resistance, we recombinantly expressed three cytochrome P450s (CYP392A16, CYP392D8 and CYP392D10) that have been associated with high levels of abamectin resistance in a resistant T. urticae strain isolated from Greece. CYP392A16 was expressed predominately in its P450 form however, both CYP392D8 and CYP392D10 were expressed predominately as P420, despite optimization efforts on expression conditions. CYP392A16 catalyses the hydroxylation of abamectin (Kcat=0.54 pmol/min/pmol P450; Km=45.9 μM), resulting in a substantially less toxic compound as confirmed by bioassays with the partially purified metabolite. However, CYP392A16 did not metabolize hexythiazox, clofentezine and bifenthrin, active ingredients that also showed reduced toxicity in the abamectin resistant strain. Among a number of fluorescent and luminescent substrates screened, Luciferin-ME EGE was preferentially metabolized by CYP392A16, and it may be a potential diagnostic probe for metabolic resistance detection and monitoring.

  6. Sub-lethal toxicity of the antiparasitic abamectin on earthworms and the application of neutral red retention time as a biomarker.

    PubMed

    Jensen, John; Diao, Xiaoping; Scott-fordsmand, Janeck J

    2007-06-01

    The antiparasitic abamectin has been proven effective against both endo- and ectoparasites of farm animals and hence used widely in animal husbandry. It may enter the soil environment with the excreta of treated animals. Very little information is available with regard to the sub-lethal effects of abamectin on soil invertebrates, such as earthworms. The objective of this study was to evaluate the toxic effect of abamectin on earthworms, using Eisenia fetida, by analyzing changes in the survival, growth, reproduction and cocoon hatchability of exposed earthworms. Furthermore, a biomarker of the lysosomal membrane stability, measured by neutral red retention time (NRR-time), was also applied. Abamectin showed significant toxicity on the growth of earthworms with increasing concentrations up to 5mg/kg. The most sensitive parameter was reproduction (cocoons production and hatchability) and NRR-time. The number of cocoons was reduced at concentrations above 0.25mg/kg and no cocoons were present at the highest concentration of 5mg/kg. Cocoons exposed to abamectin exhibited a reduced hatching success at concentrations above 1.5mg/kg. The NRR-time was reduced significantly at exposure concentrations of abamectin above 0.25mg/kg. The change in lysosomal membrane stability showed a good correlation with reproduction and may hence be a potential predicator of the effects on earthworm populations.

  7. Sodium benzoate and potassium sorbate preservatives in Iranian doogh.

    PubMed

    Zamani Mazdeh, F; Esmaeili Aftabdari, F; Moradi-Khatoonabadi, Z; Shaneshin, M; Torabi, P; Shams Ardekani, M R; Hajimahmoodi, M

    2014-01-01

    Sodium benzoate and potassium sorbate are two common preservatives used in Iran, yet use of these preservatives in doogh (Iranian dairy-based drink) is forbidden according to national standards. The aim of this study was to consider the presence of these preservatives in doogh by high-performance liquid chromatography with UV detection (HPLC-UV). The method was performed using a C18 column and detection at 225 nm. The mobile phase contained ammonium acetate buffer (pH = 4.2) and acetonitrile (80:20 v/v). The survey included 130 samples of doogh for identification and quantification of the named preservatives. All samples contained sodium benzoate, but potassium sorbate was detected in only 13% of them. The means of benzoate and sorbate were 21.3 ± 2.7 and 13.3 ± 39.6 mg kg(-1), respectively. The limits of detection were 2 and 40 ng g(-1) for benzoate and sorbate, respectively. Results indicate that sodium benzoate may occur in doogh naturally.

  8. Baseline susceptibility of persea mite (Acari: Tetranychidae) to abamectin and milbemectin in avocado groves in Southern California.

    PubMed

    Humeres, Eduardo C; Morse, Joseph G

    2005-01-01

    Persea mite, Oligonychus perseae Tuttle, Baker, and Abatiello, susceptibility to abamectin and milbemectin was evaluated in 2003 to determine baseline susceptibility levels in avocado groves in San Diego and Ventura Counties (California, USA) where more than 70% of the state's avocado production is concentrated. Milbemectin has yet to be used in avocado production in California and abamectin has been available for use since 1999. Baseline susceptibility ratios (in relation to the most susceptible population) of five persea mite field strains to milbemectin varied 2.1- to 2.8-fold at the LC50 and LC90, respectively. The susceptibility of seven field strains to abamectin varied slightly more (2.1- to 3.5-fold) with one strain subjected to seven sprays over the past 4 years showing slight but significant separation of LC50 and LC90's from the most susceptible strain, which is suggestive of the early stages of resistance to this product. Based on these data, baseline susceptibility levels are proposed that might be used to monitor for future persea mite resistance to these chemicals as their use in California avocado production continues.

  9. Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters.

    PubMed

    Semak, Vladislav; Metcalf, Thomas A; Endoma-Arias, Mary Ann A; Mach, Pavel; Hudlicky, Tomas

    2012-06-14

    A series of ortho-, meta-, and para- halogen-substituted methyl benzoate esters was subjected to enzymatic dihydroxylation via the whole-cell fermentation with E. coli JM109 (pDTG601A). Only ortho-substituted benzoates were metabolized. Methyl 2-fluorobenzoate yielded one diol regioselectively whereas methyl 2-chloro-, methyl 2-bromo- and methyl 2-iodobenzoates each yielded a mixture of regioisomers. Absolute stereochemistry was determined for all new metabolites. Computational analysis of these results and a possible rationale for the regioselectivity of the enzymatic dihydroxylation is advanced.

  10. Identification and Characterization of the Gene CYP340W1 from Plutella xylostella and Its Possible Involvement in Resistance to Abamectin

    PubMed Central

    Gao, Xue; Yang, Jiaqiang; Xu, Baoyun; Xie, Wen; Wang, Shaoli; Zhang, Youjun; Yang, Fengshan; Wu, Qingjun

    2016-01-01

    Abamectin has been used to control the diamondback moth, Plutella xylostella (P. xylostella), which is a major agricultural pest that can rapidly develop resistance against insecticides including abamectin. Although cytochrome P450 has been confirmed to play an important role in resistance in P. xylostella, the specific P450 genes associated with the resistance are unclear. The full-length cDNA of the cytochrome P450 gene CYP340W1 was cloned and characterized in the present study. The cDNA assembly yielded a sequence of 1929 bp, containing the open reading frame (ORF) 1491 bp and encodes a 496-amino acid peptide. CYP340W1 was expressed in all P. xylostella developmental stages but its expression level was highest in larvae and especially in the heads of larvae. The expression of CYP340W1 was significantly higher in an abamectin-resistant strain (ABM-R) than in its susceptible counterpart (ABM-S). In addition, expression of CYP340W1 was increased when the ABM-R strain was exposed to abamectin. When injected into third-stage ABM-R larvae, CYP340W1 dsRNA significantly reduced CYP340W1 expression at 6 h and reduced expression by 83% at 12 h. As a consequence of RNAi, the mortality of the injected abamectin-resistant larvae increased after a 48-h exposure to abamectin. The results indicate that the overexpression of CYP340W1 plays an important role in abamectin resistance in P. xylostella. PMID:26999122

  11. Anthelmintic efficacy of ivermectin and abamectin, administered orally for seven consecutive days (100 µg/kg/day), against nematodes in naturally infected pigs.

    PubMed

    Lopes, Welber Daniel Zanetti; Teixeira, Weslen Fabricio Pires; Felippelli, Gustavo; Cruz, Breno Cayeiro; Buzulini, Carolina; Maciel, Willian Giquelin; Fávero, Flávia Carolina; Gomes, Lucas Vinicius Costa; Prando, Luciana; Bichuette, Murilo A; Dos Santos, Thais Rabelo; da Costa, Alvimar José

    2014-12-01

    The present study aimed to evaluate ivermectin and abamectin, both administered orally in naturally infected domestic swine, as well as analysing if the EPG (eggs per gram of faeces) values were equivalent with the ivermectin and abamectin efficacy obtained by parasitological necropsies. The animals were randomly selected based on the average of three consecutive EPG counts of Strongylida, Ascaris suum and Trichuris for experiment I, and of Strongylida and Trichuris for experiment II. After the random draw, eight animals were treated, orally, during seven consecutive days with 100 µg/kg/day ivermectin (Ivermectina® premix, Ouro Fino Agronegócios), eight other animals were treated, orally, during seven consecutive days with 100 µg/kg/day abamectin (Virbamax® premix - Virbac do Brasil Indústria e Comércio Ltda.), and eight pigs were kept as controls. EPG counts were performed for each individual animal at 14th day post-treatment (DPT). All animals (control and treatment) were necropsied at the 14th DPT. The results from both experiments demonstrate that both ivermectin and abamectin, administered orally for a continuous period of seven days, at a daily dosage of 100 µg/kg, were highly effective (>95%) against Hyostrongylus rubidus, Strongyloides ransomi, Ascaris suum and Metastrongylus salmi. Against Oesophagostomum dentatum, abamectin presented over 95% efficacy against both evaluated strains, while ivermectin reached other strain as resistant. Regarding T. suis, both ivermectin and abamectin were effective (efficacies >90%) against one of the tested strains, while the other one was classified as resistant. Furthermore, the EPG values were equivalent with the ivermectin and abamectin efficacy obtained by parasitological necropsies.

  12. Benzoate Allergy in Children--From Foods to Personal Hygiene Products.

    PubMed

    Jacob, Sharon E; Hill, Hannah; Lucero, Hanna; Nedorost, Susan

    2016-01-01

    Benzoate allergy may be an overlooked allergen in children and one that may be of increasing importance with its increasing role as a preservative in pediatric personal hygiene formulations. The cases herein report an association with cola and benzoate allergy and discusses the implications of replacement of formaldehyde by benzoates in personal hygiene products.

  13. Correlation between pesticide resistance and enzyme activity in the diamondback moth, Plutella xylostella.

    PubMed

    Gong, Ya-Jun; Wang, Ze-Hua; Shi, Bao-Cai; Kang, Zong-Jiang; Zhu, Liang; Jin, Gui-Hua; Weig, Shu-Jun

    2013-01-01

    The diamondback moth, Plutella xylostella (L.) (Lepidoptera: Plutellidae), is one of the most important pests that has developed high pesticide resistance. The resistances of five Chinese populations of this moth, four resistant strains (from Beijing, Henan, Fujian, and Guangdong) and one susceptible strain, to five pesticides were determined, and the activities of carboxylesterase, glutathione S-transferase, and acetylcholine esterase were tested in all five populations. The correlations between pesticide resistance and enzyme activity were analyzed. The results showed that the resistance status to the five pesticides was different among the five populations. The resistance ratios of the Beijing and Henan populations to spinosad were 5.84 and 8.22, respectively, and those to beta-cypermethrin were 4.91 and 4.98, respectively. These ratios were higher than those for the Fujian and Guangdong populations. The Fujian population was more sensitive to abamectin and chlorpyrifos than the susceptible population (the resistance ratios were 0.14 and 0.91, respectively); in fact, the median lethal concentration for P. xylostella was significantly higher for chlorpyrifos than that for any of the other four pesticides. The carboxylesterase activity in P. xylostella showed positive correlations with the resistance to spinosad, beta-cypermethrin, chlorpyrifos, and abamectin, but no correlation was observed between the carboxylesterase activity and resistance to emamectin benzoate, between glutathione S-transferase activity and resistance to any of the five pesticides tested, or between acetylcholine esterase activity and any of the pesticides except for emamectin benzoate.

  14. Development of abamectin loaded plant virus nanoparticles for efficacious plant parasitic nematode control.

    PubMed

    Cao, Jing; Guenther, Richard H; Sit, Tim L; Lommel, Steven A; Opperman, Charles H; Willoughby, Julie A

    2015-05-13

    Plant parasitic nematodes are one of the world's major agricultural pests, causing in excess of $157 billion in worldwide crop damage annually. Abamectin (Abm) is a biological pesticide with a strong activity against a wide variety of plant parasitic nematodes. However, Abm's poor mobility in the soil compromises its nematicide performance because of the limited zone of protection surrounding the growing root system of the plant. In this study, we manipulated Abm's soil physical chemistry by encapsulating Abm within the Red clover necrotic mosaic virus (RCNMV) to produce a plant virus nanoparticle (PVN) delivery system for Abm. The transmission electron microscopic and dynamic light scattering characterization of Abm-loaded PVN (PVN(Abm)) indicated the resultant viral capsid integrity and morphology comparable to native RCNMV. In addition, the PVN(Abm) significantly increased Abm's soil mobility while enabling a controlled release strategy for Abm's bioavailability to nematodes. As a result, PVN(Abm) enlarged the zone of protection from Meloidogyne hapla root knot nematodes in the soil as compared to treating with free Abm molecules. Tomato seedlings treated with PVN(Abm) had healthier root growth and a reduction in root galling demonstrating the success of this delivery system for the increased efficacy of Abm to control nematode damage in crops.

  15. Antimicrobial activity of synthetic bornyl benzoates against Trypanosoma cruzi

    PubMed Central

    Corrêa, P R C; Miranda, R R S; Duarte, L P; Silva, G D F; Filho, S A Vieira; Okuma, A A; Carazza, F; Morgado-Díaz, J A; Pinge-Filho, P; Yamauchi, L M; Nakamura, C V; Yamada-Ogatta, S F

    2012-01-01

    We report here for the first time the in vitro effects of (1S,2R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-yl-3′,4′,5′-trimethoxy benzoate (1) and (1S,2R,4S)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-yl benzoate (2) on the growth and ultrastructure of Trypanosoma cruzi. These two synthetic compounds exerted an antiproliferative effect on the epimastigote forms of the parasite. The ICs50/72h of two synthetic L-bornyl benzoates, 1 and 2, was 10.1 and 12.8 μg/ml, respectively. Both compounds were more selective against epimastigotes than HEp-2 cells. Ultrastructural analysis revealed intense cytoplasmic vacuolization and the appearance of cytoplasmic materials surrounded by membranes. The treatment of peritoneal macrophages with compounds 1 and 2 caused a significant decrease in the number of T. cruzi-infected cells. L-Bornyl benzoate derivatives may serve as a potential source for the development of more effective and safer chemotherapeutic agents against T. cruzi infections. PMID:22943546

  16. 21 CFR 522.842 - Estradiol benzoate and testosterone propionate.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Estradiol benzoate and testosterone propionate. 522.842 Section 522.842 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS IMPLANTATION OR INJECTABLE DOSAGE FORM...

  17. 21 CFR 522.842 - Estradiol benzoate and testosterone propionate.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Estradiol benzoate and testosterone propionate. 522.842 Section 522.842 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS IMPLANTATION OR INJECTABLE DOSAGE FORM...

  18. 21 CFR 522.842 - Estradiol benzoate and testosterone propionate.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Estradiol benzoate and testosterone propionate. 522.842 Section 522.842 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS IMPLANTATION OR INJECTABLE DOSAGE FORM...

  19. 21 CFR 522.842 - Estradiol benzoate and testosterone propionate.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Estradiol benzoate and testosterone propionate. 522.842 Section 522.842 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS IMPLANTATION OR INJECTABLE DOSAGE FORM...

  20. 21 CFR 522.842 - Estradiol benzoate and testosterone propionate.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Estradiol benzoate and testosterone propionate. 522.842 Section 522.842 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS IMPLANTATION OR INJECTABLE DOSAGE FORM...

  1. 21 CFR 522.2478 - Trenbolone acetate and estradiol benzoate.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... consists of: (1) 8 pellets, each pellet containing 25 milligrams (mg) trenbolone acetate and 3.5 mg estradiol benzoate. (2) 4 pellets, each pellet containing 25 mg trenbolone acetate and 3.5 mg estradiol...) For an implant as described in paragraph (a)(1) of this section: (A) Amount. 200 mg trenbolone...

  2. 21 CFR 522.2478 - Trenbolone acetate and estradiol benzoate.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... consists of: (1) 8 pellets, each pellet containing 25 milligrams (mg) trenbolone acetate and 3.5 mg estradiol benzoate. (2) 4 pellets, each pellet containing 25 mg trenbolone acetate and 3.5 mg estradiol...) For an implant as described in paragraph (a)(1) of this section: (A) Amount. 200 mg trenbolone...

  3. Effects of azadirachtin, abamectin, and spinosad on sweetpotato whitefly (Homoptera: Aleyrodidae) on tomato plants under laboratory and greenhouse conditions in the humid tropics.

    PubMed

    Kumar, Prabhat; Poehling, H M

    2007-04-01

    Direct and residual toxicity of NeemAzal-T/S (azadirachtin), Success (spinosad), and abamectin was tested against different life stages of sweetpotato whitefly, Bemisia tabaci (Gennadius) (Homoptera: Aleyrodidae), under air-conditioned laboratory conditions and in a tropical net greenhouse. NeemAzal-T/S and abamectin deterred the settling of adults on tomato, Lycopersicon esculentum Mill (Solanaceae), plants and consequently reduced egg deposition. No such effect was detected for Success. All three pesticides influenced egg hatch. Effects of NeemAzal-T/ S were significantly altered if applied to different-aged eggs (1, 3, and 5 d old). In contrast, abamectin-treated eggs failed to hatch at any given age class. All three products caused heavy mortality of the three nymphal stages of B. tabaci, with the first instars being most susceptible, abamectin-treated nymphs died within 24 h postapplication. In contrast, 100% nymphal mortality with NeemAzal-T/S and Success was reached 6-9 d postapplication. abamectin caused 100% immature mortality at all residue ages (1, 5, 10, and 15 d) in the laboratory and greenhouse as well. Persistence of Success was comparably high in the laboratory, but in the greenhouse a faster decline of activity was evident by increased egg deposition, egg hatch, and reduced rates of immature mortality. Toxicity of NeemAzal-T/S however gradually declined under greenhouse conditions with time (5 d) postapplication. The findings are discussed within the context of integrated management of whitefly under protected cultivation in the humid tropics.

  4. Assessment of estimated daily intakes of benzoates for average and high consumers in Korea.

    PubMed

    Yoon, Hae Jung; Cho, Yang Hee; Park, Juyeon; Lee, Chang Hee; Park, Sung Kwan; Cho, Young Ju; Han, Ki Won; Lee, Jong Ok; Lee, Chul Won

    2003-02-01

    A study was performed to evaluate the estimated daily intakes (EDI) of benzoates for the average and high (90th percentile) consumers by age and sex categories in Korea. The estimation of daily intakes of benzoates was based on individual dietary intake data from the National Health and Nutrition Survey in 1998 and on the determination of benzoates in eight food categories. The EDI of benzoates for average consumers of different age groups ranged from 0.009 to 0.025 mg kg(-1) bw day(-1). For high consumers, the range of EDI of benzoates was 0.195-1.878 mg kg(-1) bw day(-1). The intakes represented 0.18-0.50% of the acceptable daily intake (ADI) of benzoates for average consumers and 3.9-37.6% of the ADI for high consumers. Foods that contributed most to the daily intakes of benzoates were mixed beverages and soy sauce in Korea.

  5. [Study on THz spectra and vibrational modes of benzoic acid and sodium Benzoate].

    PubMed

    Zheng, Zhuan-Ping; Fan, Wen-Hui; Yan, Hui; Liu, Jia; Xu, Li-Min

    2013-03-01

    Terahertz time-domain spectroscopy was employed to measure the terahertz absorption spectra of benzoic acid and sodium benzoate at room temperature. The origins of the measured features of benzoic acid were summarized based on previous study. Density functional theory was used to compute and analyze the molecular structure and vibrational modes of sodium benzoate in monomer. Based on the obtained results, the authors found that the THz spectral features can be used to distinguish benzoic acid and sodium benzoate totally; the essential reason for the THz spectral difference between benzoic acid and sodium benzoate is that the electrovalent bond of sodium benzoate affects the values of covalent bond lengths and bond angles, as well as the molecular interactions and arrangement in unit cell; the measured features of benzoic acid and sodium benzoate come from the collective vibrations except the peaks located at 107 cm-1 of benzoic acid and 54 cm-1 of sodium benzoate.

  6. Toxicity of Vertimec® 18 EC (active ingredient abamectin) to the neotropical cladoceran Ceriodaphnia silvestrii.

    PubMed

    Casali-Pereira, Maressa P; Daam, Michiel A; de Resende, Juliana C; Vasconcelos, Ana M; Espíndola, Evaldo L G; Botta, Clarice M R

    2015-11-01

    The aim of the present study was to evaluate the toxicity of abamectin to the neotropical cladoceran Ceriodaphnia silvestrii. To this end, acute and chronic bioassays were conducted with the commercial formulation Vertimec® 18 EC. In addition, the toxicity of water samples taken from a microcosm experiment evaluating the effects of a single application (144μga.i./L) and two applications (2×36μga.i./L) of Vertimec® 18 EC, in the presence or absence of a tadpole species (Lithobates catesbeianus), was also assessed. The acute LC50-48h for immobilization was 1.47μga.i./L and chronic NOEC-8d for survival and fertility (number of neonates per female) were 169 and 84nga.i./L, respectively. Irrespective of the presence of tadpoles, water samples from the microcosms applied with the single concentration of 144μga.i./L remained toxic until the end of the experiment, even when samples were diluted 32 times with culture medium. Water in the repeated pesticide treatment showed a similar toxic response after both applications. Toxicity of water samples from the microcosms was lower than that expected based on the generated LC50 values, which is explained by a potential reduced bioavailability of the test compound resulting from absorbance to organic material. Potential side-effects on C. silvestrii related with the use of Vertimec® 18 EC in Brazil and the suitability of this species for tropical toxicity testing are discussed.

  7. Interspecies acetate transfer influences the extent of anaerobic benzoate degradation by syntrophic consortia

    SciTech Connect

    Warikoo, V.; McInerney, M.J.; Suflita, J.M.

    1997-03-01

    Benzoate degradation by an anaerobic, syntrophic bacterium, strain SB, in coculture with Desulfovibrio strain G-11 reached a threshold value which depended on the amount of acetate added, and ranged from about 2.5 to 29.9 {mu}M. Increasing acetate concentrations also uncompetitively inhibited benzoate degradation. The apparent V{sub max} and K{sub m} for benzoate degradation decreased with increasing acetate concentration, but the benzoate degradation capacity (V{sub max}/K{sub m}) of cell suspensions remained comparable. The addition of an acetate-using bacterium to cocultures after the threshold was reached resulted in the degradation of benzoate to below the detection limit. Mathematical simulations showed that the benzoate threshold was not predicted by the inhibitory effect of acetate on benzoate degradation kinetics. With nitrate instead of sulfate as the terminal electron acceptor, no benzoate threshold was observed in the presence of 20 mM acetate even though the degradation capacity was lower with nitrate than with sulfate. When strain SB was grown with a hydrogen-using partner that had a 5-fold lower hydrogen utilization capacity, a 5 to 9-fold lower the benzoate degradation capacity was observed compared to SB/G-11 cocultures. The Gibb`s free energy for benzoate degradation was less negative in cell suspensions with threshold compared to those without threshold. These studies showed that the threshold was not a function of the inhibition of benzoate degradation capacity by acetate, or the toxicity of the undissociated form of acetate. Rather a critical or minimal Gibb`s free energy may exist where thermodynamic constraints preclude further benzoate degradation.

  8. Determination of Hammett Equation Rho Constant for the Hydrolysis of p-Nitrophenyl Benzoate Esters

    ERIC Educational Resources Information Center

    Keenan, Sheue L.; Peterson, Karl P.; Peterson, Kelly; Jacobson, Kyle

    2008-01-01

    Seven p-nitrophenyl benzoate esters (p-nitrophenyl benzoate, p-nitrophenyl m-anisate, p-nitrophenyl p-anisate, p-nitrophenyl m-chlorobenzoate, p-nitrophenyl p-chlorobenzoate, p-nitrophenyl m-toluate, p-nitrophenyl p-toluate) were synthesized and characterized by students in a second-semester organic laboratory course. In a subsequent laboratory…

  9. 40 CFR 721.10062 - 2,5-Furandione, polymer with oxybis[propanol], benzoate.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2,5-Furandione, polymer with oxybis... Specific Chemical Substances § 721.10062 2,5-Furandione, polymer with oxybis , benzoate. (a) Chemical...-furandione, polymer with oxybis , benzoate (PMN P-04-627; CAS No. 103458-14-6) is subject to reporting...

  10. 40 CFR 721.10062 - 2,5-Furandione, polymer with oxybis[propanol], benzoate.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2,5-Furandione, polymer with oxybis... Specific Chemical Substances § 721.10062 2,5-Furandione, polymer with oxybis , benzoate. (a) Chemical...-furandione, polymer with oxybis , benzoate (PMN P-04-627; CAS No. 103458-14-6) is subject to reporting...

  11. 40 CFR 721.10062 - 2,5-Furandione, polymer with oxybis[propanol], benzoate.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false 2,5-Furandione, polymer with oxybis... Specific Chemical Substances § 721.10062 2,5-Furandione, polymer with oxybis , benzoate. (a) Chemical...-furandione, polymer with oxybis , benzoate (PMN P-04-627; CAS No. 103458-14-6) is subject to reporting...

  12. 40 CFR 721.10062 - 2,5-Furandione, polymer with oxybis[propanol], benzoate.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false 2,5-Furandione, polymer with oxybis... Specific Chemical Substances § 721.10062 2,5-Furandione, polymer with oxybis , benzoate. (a) Chemical...-furandione, polymer with oxybis , benzoate (PMN P-04-627; CAS No. 103458-14-6) is subject to reporting...

  13. 40 CFR 721.10062 - 2,5-Furandione, polymer with oxybis[propanol], benzoate.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 2,5-Furandione, polymer with oxybis... Specific Chemical Substances § 721.10062 2,5-Furandione, polymer with oxybis , benzoate. (a) Chemical...-furandione, polymer with oxybis , benzoate (PMN P-04-627; CAS No. 103458-14-6) is subject to reporting...

  14. Reduced efficacy of moxidectin and abamectin in young red deer (Cervus elaphus) after 20 years of moxidectin pour-on use on a New Zealand deer farm.

    PubMed

    Mackintosh, C G; Cowie, C; Fraser, K; Johnstone, P; Mason, P C

    2014-01-17

    A study was undertaken on weaned 4-5 month old farmed red deer to test the efficacy of moxidectin and abamectin anthelmintics, given by three different routes of administration, compared with an untreated control. Faecal samples were collected on days 0, 7 and 14 for a faecal egg count reduction test (FECRT), blood samples were collected on days 0, 0.5, 1, 2, 3, 5, 7, 10 and 14 for pharmacokinetics, and the deer were killed on days 14 or 15 for total nematode count. The control group averaged 1264 adult Ostertagia-type nematode parasite species and treatment efficacy was 77.4% for moxidectin injection, 26% for oral moxidectin and 27.6% for pour-on moxidectin, while the treatment efficacy was 72.4% for abamectin injection, 70.1% for oral abamectin (Hi-Mineral) and 34.1% for pour-on abamectin. Both moxidectin and abamectin injections were significantly more efficacious than their equivalent pour-ons. There was a significant difference in efficacy between oral abamectin (Hi-Mineral) and oral moxidectin (P<0.01). The control group averaged 2956 adult lungworm (Dictyocaulus eckerti) and 50 Oesophagostomum venulosum in the large intestine and treatment efficacy against these nematodes was 100% for all treatments. There were negligible numbers of other gastro-intestinal nematodes. At slaughter, there was a significant correlation (P=0.02) between FEC and Ostertagia-type nematodes in the untreated controls. Relatively few eggs were found in faeces from treated animals at 7 and 14 days post-treatment despite significant worm burdens in all six treatment groups, suggesting egg-laying suppression in resistant nematodes, and all three different FECRT calculations tended to overestimate the efficacy of the treatments compared with actual nematode counts. Peak plasma concentrations (Cmax) for both actives were measured 12h after treatment for injection and oral and at 5 days for pour-on. Cmax (ng/ml) for moxidectin injection, oral and pour-on were 71.8, 8.3 and 0.4, respectively

  15. 40 CFR 721.4060 - Alkylene glycol tereph-tha-late and substituted benzoate esters (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... substituted benzoate esters (generic name). 721.4060 Section 721.4060 Protection of Environment ENVIRONMENTAL... substituted benzoate esters (generic name). (a) Chemical substance and significant new uses subject to... substituted benzoate esters (PMN P-89-596) is subject to reporting under this section for the significant...

  16. 40 CFR 721.4060 - Alkylene glycol tereph-tha-late and substituted benzoate esters (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... substituted benzoate esters (generic name). 721.4060 Section 721.4060 Protection of Environment ENVIRONMENTAL... substituted benzoate esters (generic name). (a) Chemical substance and significant new uses subject to... substituted benzoate esters (PMN P-89-596) is subject to reporting under this section for the significant...

  17. Comparative proteomic analysis reveals mechanistic insights into Pseudomonas putida F1 growth on benzoate and citrate

    PubMed Central

    2013-01-01

    Pseudomonas species are capable to proliferate under diverse environmental conditions and thus have a significant bioremediation potential. To enhance our understanding of their metabolic versatility, this study explores the changes in the proteome and physiology of Pseudomonas putida F1 resulting from its growth on benzoate, a moderate toxic compound that can be catabolized, and citrate, a carbon source that is assimilated through central metabolic pathways. A series of repetitive batch cultivations were performed to ensure a complete adaptation of the bacteria to each of these contrasting carbon sources. After several growth cycles, cell growth stabilized at the maximum level and exhibited a reproducible growth profile. The specific growth rates measured for benzoate (1.01 ± 0.11 h-1) and citrate (1.11 ± 0.12 h-1) were similar, while a higher yield was observed for benzoate (0.6 and 0.3 g cell mass per g of benzoate and citrate, respectively), reflecting the different degrees of carbon reduction in the two substrates. Comparative proteomic analysis revealed an enrichment of several oxygenases/dehydrogenases in benzoate-grown cells, indicative of the higher carbon reduction of benzoate. Moreover, the upregulation of all 14 proteins implicated in benzoate degradation via the catechol ortho-cleavage pathway was observed, while several stress-response proteins were increased to aid cells to cope with benzoate toxicity. Unexpectedly, citrate posed more challenges than benzoate in the maintenance of pH homeostasis, as indicated by the enhancement of the Na+/H+ antiporter and carbonic anhydrase. The study provides important mechanistic insights into Pseudomonas adaptation to varying carbon sources that are of great relevance to bioremediation efforts. PMID:24156539

  18. Intensification of abamectin pesticide degradation using the combination of ultrasonic cavitation and visible-light driven photocatalytic process: Synergistic effect and optimization study.

    PubMed

    Mosleh, Soleiman; Rahimi, Mahmood Reza

    2017-03-01

    Degradation of abamectin pesticide was carried out using visible light driven Cu2(OH)PO4-HKUST-1 MOF photocatalyst through the sonophotocatalytic technique. Cu2(OH)PO4-HKUST-1 MOF as a visible-light driven photocatalyst, was synthesized and characterized by XRD, SEM, EDS and DRS. The direct bang gaps of HKUST-1 MOF and Cu2(OH)PO4-HKUST-1 MOF were estimated about 2.63 and 2.59eV, respectively, which reveals that these photocatalysts can be activated under blue light illumination. All sonophotodegradation experiments were performed using a continuous flow-loop reactor. The central composite design (CCD) methodology was applied for modeling, optimization and investigation of influence of operational parameters, i.e. irradiation time, pH, solution flow rate, oxygen flow rate, initial concentration and photocatalyst dosage on the sonophotocatalytic degradation of abamectin. The maximum degradation efficiency of 99.93% was found at optimal values as 20min, 4, 90mL/min, 0.2mL/min, 30mg/L and 0.4g/L, for irradiation time, pH, solution flow rate, oxygen flow rate, initial concentration and photocatalyst dosage, respectively. Evaluation of the synergism in the combination of ultrasonic and photocatalysis lead to a synergistic index of 2.19, which reveals that coupling of ultrasonic and photocatalysis has a greater efficiency than the sum of individual procedures for degradation of abamectin.

  19. [Reductive Dechlorination of Trichloroethylene by Benzoate-Enriched Anaerobic Cultures].

    PubMed

    Li, Jiang-wei; Yang, Xiao-yong; Hu, An-yi; Yu, Chang-ping

    2015-10-01

    Gas chromatography was used to monitor the reductive dechlorination of trichloroethylene (TCE) by anaerobic enrichment cultures with benzoate as the sole carbon source. The 454 pyrosequencing technique was used to investigate the microbial community and the real-time quantitative PCR was used to quantify the gene copies of Dehalococcoides spp. (DHC). The results showed that TCE was dechlorinated to vinyl chloride along with the formation of methane in 94 days. The anaerobic enrichment cultures exhibited a high diversity, which were classified into 16 phyla, 33 classes, 52 orders, 88 families and 129 genera, while 51.2% of them belonged to unclassified group, which inferred that there were a large portion of bacteria with unknown functional in this system. Degradation of TCE was accomplished by reductive dechlorinating and other functional populations, and the DHC which carried tceA gene could be the dominant reductive dechlorinating populations in the system.

  20. 2-Amino-5-methyl-pyridinium 2-amino-benzoate.

    PubMed

    Thanigaimani, Kaliyaperumal; Farhadikoutenaei, Abbas; Khalib, Nuridayanti Che; Arshad, Suhana; Razak, Ibrahim Abdul

    2012-11-01

    In the 2-amino-benzoate anion of the title salt, C(6)H(9)N(2) (+)·C(7)H(6)NO(2) (-), an intra-molecular N-H⋯O hydrogen bond is observed. The dihedral angle between the ring and the CO(2) group is 8.41 (13)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The ion pairs are further connected via N-H⋯O hydrogen bonds, resulting in a donor-donor-acceptor-acceptor (DDAA) array of quadruple hydrogen bonds. The crystal structure also features a weak N-H⋯O hydrogen bond and a C-H⋯π inter-action, resulting in a three-dimensional network.

  1. Anaphylaxis Triggered by Benzyl Benzoate in a Preparation of Depot Testosterone Undecanoate

    PubMed Central

    Ong, Gregory S. Y.; Somerville, Colin P.; Jones, Timothy W.; Walsh, John P.

    2012-01-01

    We report the first case of an anaphylactic reaction to Reandron 1000 (depot testosterone undecanoate with a castor oil and benzyl benzoate vehicle). While considered to have a favourable safety profile, serious complications such as oil embolism and anaphylaxis can occur. In our patient, skin testing identified benzyl benzoate to be the trigger, with no reaction to castor oil or testosterone undecanoate components. As benzyl benzoate exists in multiple pharmaceuticals, foods, and cosmetics, individual components of pharmaceuticals should be tested when investigating drug allergies. Doctors should be alert to the potential for serious reactions to any of the components of Reandron 1000. PMID:22272209

  2. A computer simulation study to evaluate resistance development with a derquantel-abamectin combination on UK sheep farms.

    PubMed

    Learmount, J; Taylor, M A; Bartram, D J

    2012-06-08

    UK guidelines for the sustainable control of parasites in sheep (SCOPS) aim to delay further development of anthelmintic drug resistance. This study describes a computer model evaluation of resistance development with a novel oral formulation of derquantel-abamectin, to inform recommendations for use. Two different farm management scenarios, based on UK field data, were modelled to simulate low refugia (non SCOPS) or high refugia (SCOPS) worm populations. The effect on resistance allele frequencies and field efficacy of several treatment scenarios using the novel active derquantel (DQL), a spiroindole (SI), as either a single or multiple active formulation with abamectin (ABA), a macrocyclic lactone (ML), under the two farm management systems was evaluated. The initial resistance allele frequency for DQL was set at 0.0001, assuming that resistance in the UK is low, and for ML at 0.165 or 0.8, assuming that resistant nematode populations exist in the UK. DQL resistance reached a level at which a reduction in field efficacy might be detected (resistance allele frequency 0.25) by year 16 when used sequentially, and by year 31 when used in annual rotation (ABA) with SCOPS management inputs, and by year 5 (sequential) and by year 10 (annual rotation) with non SCOPS management inputs. ML resistance reached a level at which a reduction in ABA field efficacy might be detected (resistance allele frequency 0.25) by year 4 when used sequentially, and by year 8 when used in annual rotation with DQL and SCOPS management inputs, and by year 1 (sequential) and by year 2 (annual rotation) with non SCOPS management inputs. No detectable reduction in field efficacy was observed for DQL-ABA after 40 years of use with SCOPS management inputs for simulations using an initial ML resistance allele frequency of 0.165 and 0.8. A detectable reduction in field efficacy was observed for DQL-ABA by year 32 (initial ML resistance allele frequency=0.165) and by year 6 (initial ML resistance

  3. Hyperammonemic encephalopathy after chemotherapy. Survival after treatment with sodium benzoate and sodium phenylacetate.

    PubMed

    del Rosario, M; Werlin, S L; Lauer, S J

    1997-12-01

    A 16-year-old boy had hyperammonemia and encephalopathy develop after high-dose chemotherapy for acute lymphoblastic leukemia. He was treated successfully with the ammonia-trapping agents sodium benzoate and sodium phenylacetate.

  4. Laboratory Evaluation of Two Commercial Abamectin-Based Insecticides Against Anastrepha ludens (Diptera: Tephritidae): Lethal and Sublethal Effects.

    PubMed

    Díaz-Fleischer, Francisco; Pérez-Staples, Diana; Valle-Mora, Javier; Antonio García-Pérez, José

    2016-10-05

    Toxic environmental effects of most insecticides have led to a search for bio-organic insecticides. In this study, we tested the effects of lethal and sublethal exposure to two abamectin-based insecticides (VOLIAM TARGO and LUQ-THOR) on survival, mating, and oviposition of the tephritid Anastrepha ludens (Loew). Different doses of insecticides (0.001-2.00% of the commercial products) were offered mixed with the phagostimulant bait Captor commonly used in spraying and in trapping activities for the control of flies. Both insecticides exhibited 90% killing effectiveness (Abbott index) when offered in doses between 0.02 to 2.00%. The LC50 obtained from the bioassay at 72 h after treatment was 0.003% of commercial product for TARGO and 0.008% for LUQ-THOR. Sublethal exposures to insecticides (0.003%; LC50 for TARGO and LC30 for LUQ-THOR) caused a reduction in oviposition but not in mating parameters, indicating that females were more susceptible than males to reduced doses of insecticide. The mean amount of eggs deposited 5 d after feeding on the insecticide-bait mixtures was reduced up to a third compared with the amount of eggs deposited by untreated females. Both insecticides are promising bio-organic alternatives to malathion in bait control programs against A. ludens.

  5. Estimated crop loss due to coconut mite and financial analysis of controlling the pest using the acaricide abamectin.

    PubMed

    Rezende, Daniela; Melo, José W S; Oliveira, José E M; Gondim, Manoel G C

    2016-07-01

    Reducing the losses caused by Aceria guerreronis Keifer has been an arduous task for farmers. However, there are no detailed studies on losses that simultaneously analyse correlated parameters, and very few studies that address the economic viability of chemical control, the main strategy for managing this pest. In this study the objectives were (1) to estimate the crop loss due to coconut mite and (2) to perform a financial analysis of acaricide application to control the pest. For this, the following parameters were evaluated: number and weight of fruits, liquid albumen volume, and market destination of plants with and without monthly abamectin spraying (three harvests). The costs involved in the chemical control of A. guerreronis were also quantified. Higher A. guerreronis incidence on plants resulted in a 60 % decrease in the mean number of fruits harvested per bunch and a 28 % decrease in liquid albumen volume. Mean fruit weight remained unaffected. The market destination of the harvested fruit was also affected by higher A. guerreronis incidence. Untreated plants, with higher A. guerreronis infestation intensity, produced a lower proportion of fruit intended for fresh market and higher proportions of non-marketable fruit and fruit intended for industrial processing. Despite the costs involved in controlling A. guerreronis, the difference between the profit from the treated site and the untreated site was 18,123.50 Brazilian Real; this value represents 69.1 % higher profit at the treated site.

  6. Effect of Larvae Treated with Mixed Biopesticide Bacillus thuringiensis - Abamectin on Sex Pheromone Communication System in Cotton Bollworm, Helicoverpa armigera

    PubMed Central

    Shen, Li-Ze; Chen, Peng-Zhou; Xu, Zhi-Hong; Deng, Jian-Yu; Harris, Marvin-K; Wanna, Ruchuon; Wang, Fu-Min; Zhou, Guo-Xin; Yao, Zhang-Liang

    2013-01-01

    Third instar larvae of the cotton bollworm (Helicoverpa armigera) were reared with artificial diet containing a Bacillus thuringiensis - abamectin (BtA) biopesticide mixture that resulted in 20% mortality (LD20). The adult male survivors from larvae treated with BtA exhibited a higher percentage of “orientation” than control males but lower percentages of “approaching” and “landing” in wind tunnel bioassays. Adult female survivors from larvae treated with BtA produced higher sex pheromone titers and displayed a lower calling percentage than control females. The ratio of Z-11-hexadecenal (Z11–16:Ald) and Z-9-hexadecenal (Z9–16:Ald) in BtA-treated females changed and coefficients of variation (CV) of Z11–16:Ald and Z9–16:Ald were expanded compared to control females. The peak circadian calling time of BtA-treated females occurred later than that of control females. In mating choice experiment, both control males and BtA-treated males preferred to mate with control females and a portion of the Bt-A treated males did not mate whereas all control males did. Our Data support that treatment of larvae with BtA had an effect on the sex pheromone communication system in surviving H.armigera moths that may contribute to assortative mating. PMID:23874751

  7. Photochemistry of 2-alkoxymethyl-5-methylphenacyl chloride and benzoate.

    PubMed

    Plístil, Lukás; Solomek, Tomás; Wirz, Jakob; Heger, Dominik; Klán, Petr

    2006-10-13

    Irradiation of 2-(alkoxymethyl)-5-methyl-alpha-chloroacetophenones (1a-c) and 2-(methoxymethyl)-5-methylphenacyl benzoate (1d) in dry, nonnucleophilic solvents afforded 3-alkoxy-6-methylindan-1-ones (3a-c) in very high chemical yields. 3-Methylisobenzofuran-1(3H)-one (2) was, however, isolated as a major photoproduct in the presence of trace amounts of water. Quenching experiments and laser flash spectroscopy revealed that the indanone derivatives 3 are formed by 1,5-hydrogen migration from the lowest triplet excited state of the acetophenones 1 and cyclization of the resulting photoenols. In contrast, production of the lactone 2 in wet solvents was found to result from two consecutive photochemical transformations. The photoenols produced by photolysis of 1a-c add water as a nucleophile to form 2-acetyl-4-methylbenzaldehyde (4), which is further converted to 2 via a second, singlet state photoenolization process. Exhaustive photolysis of 1a in methanol produced the acetal 2-(dimethoxymethyl)-5-methylacetophenone (7a) as the exclusive product. The remarkable selectivity of these photoreactions may well be useful in synthetic organic chemistry.

  8. A Floral Fragrance, Methyl Benzoate, is An Efficient Green Pesticide

    NASA Astrophysics Data System (ADS)

    Feng, Yan; Zhang, Aijun

    2017-02-01

    Over-reliance on synthetic pesticides in insect pest control has caused widespread public and scientific concerns for human health and the environment, especially since many insect pests have already developed resistances to conventional pesticides and Bt products. For this reason, there is a considerable interest in development of alternative control methods for insect pest management. Based on laboratory studies, we report that methyl benzoate (MB), a naturally-occurring compound in many plants, may possess toxicity against various stages of a variety of insect pests, including the brown marmorated stinkbug, Halyomorpha halys, diamondback moth, Plutella xylostella, and tobacco hornworm, Manduca sexta, as well as the spotted wing drosophila, Drosophila suzukii. Based on our laboratory toxicity data, MB was at least 5 to 20 times more toxic than the conventional pyrethroid (β-cyfluthrin), sulfur & pyrethrin mixture, and some organic commercial products available on the market against H. halys, P. xylostella, and M. sexta, eggs. Because MB is considered an environment-friendly, it has great potential to be used as an alternative tool to synthetic pesticide for insect pest management in crop production, thereby, reducing threats to natural ecosystems and human health caused by over-application of conventional synthetic pesticides.

  9. A Floral Fragrance, Methyl Benzoate, is An Efficient Green Pesticide

    PubMed Central

    Feng, Yan; Zhang, Aijun

    2017-01-01

    Over-reliance on synthetic pesticides in insect pest control has caused widespread public and scientific concerns for human health and the environment, especially since many insect pests have already developed resistances to conventional pesticides and Bt products. For this reason, there is a considerable interest in development of alternative control methods for insect pest management. Based on laboratory studies, we report that methyl benzoate (MB), a naturally-occurring compound in many plants, may possess toxicity against various stages of a variety of insect pests, including the brown marmorated stinkbug, Halyomorpha halys, diamondback moth, Plutella xylostella, and tobacco hornworm, Manduca sexta, as well as the spotted wing drosophila, Drosophila suzukii. Based on our laboratory toxicity data, MB was at least 5 to 20 times more toxic than the conventional pyrethroid (β-cyfluthrin), sulfur & pyrethrin mixture, and some organic commercial products available on the market against H. halys, P. xylostella, and M. sexta, eggs. Because MB is considered an environment-friendly, it has great potential to be used as an alternative tool to synthetic pesticide for insect pest management in crop production, thereby, reducing threats to natural ecosystems and human health caused by over-application of conventional synthetic pesticides. PMID:28181532

  10. Do Biopesticides Affect the Demographic Traits of a Parasitoid Wasp and Its Biocontrol Services through Sublethal Effects?

    PubMed Central

    Biondi, Antonio; Zappalà, Lucia; Stark, John D.; Desneux, Nicolas

    2013-01-01

    Pesticide risk assessments are usually based on short-term acute toxicity tests, while longer-term population dynamic related traits, critical to the success of biological control and Integrated Pest Management (IPM) programs, are often overlooked. This is increasingly important with respect to new biopesticides that frequently cause no short-term acute effects, but that can induce multiple physiological and behavioral sublethal effects, leading to a decrease in population growth and ecosystem services. In this study we assessed the lethal and sublethal effects of six biopesticides [abamectin, azadirachtin, Bacillus thuringiensis, borax plus citrus oil (Prev-Am®), emamectin benzoate, and spinosad], used in tomato crops to control the invasive pest Tuta absoluta (Lepidoptera: Gelechiidae), on adults and pupae of the parasitoid Bracon nigricans (Hymenoptera: Braconidae). Data on female survival and production of female offspring were used to calculate population growth indexes as a measure of population recovery after pesticide exposure. Spinosad caused 100% and 80% mortality in exposed adults (even 10 d after the treatment) and pupae, respectively. Although most of the biopesticides had low levels of acute toxicity, multiple sublethal effects were observed. The biocontrol activity of both females that survived 1-h and 10-d old residues, and females that emerged from topically treated pupae was significantly affected by the application of the neurotoxic insecticides emamectin benzoate and abamectin. Furthermore, very low B. nigricans demographic growth indices were estimated for these two insecticides, indicating potential local extinction of the wasp populations. Among the tested products, Bt proved to be the safest for B. nigricans adults and pupae. Our findings emphasize that acute toxicity assessment alone cannot fully predict the actual impact of pesticides on non-target parasitoids. Thus, sublethal effects related to the species specific life-history variables

  11. Do biopesticides affect the demographic traits of a parasitoid wasp and its biocontrol services through sublethal effects?

    PubMed

    Biondi, Antonio; Zappalà, Lucia; Stark, John D; Desneux, Nicolas

    2013-01-01

    Pesticide risk assessments are usually based on short-term acute toxicity tests, while longer-term population dynamic related traits, critical to the success of biological control and Integrated Pest Management (IPM) programs, are often overlooked. This is increasingly important with respect to new biopesticides that frequently cause no short-term acute effects, but that can induce multiple physiological and behavioral sublethal effects, leading to a decrease in population growth and ecosystem services. In this study we assessed the lethal and sublethal effects of six biopesticides [abamectin, azadirachtin, Bacillus thuringiensis, borax plus citrus oil (Prev-Am®), emamectin benzoate, and spinosad], used in tomato crops to control the invasive pest Tuta absoluta (Lepidoptera: Gelechiidae), on adults and pupae of the parasitoid Bracon nigricans (Hymenoptera: Braconidae). Data on female survival and production of female offspring were used to calculate population growth indexes as a measure of population recovery after pesticide exposure. Spinosad caused 100% and 80% mortality in exposed adults (even 10 d after the treatment) and pupae, respectively. Although most of the biopesticides had low levels of acute toxicity, multiple sublethal effects were observed. The biocontrol activity of both females that survived 1-h and 10-d old residues, and females that emerged from topically treated pupae was significantly affected by the application of the neurotoxic insecticides emamectin benzoate and abamectin. Furthermore, very low B. nigricans demographic growth indices were estimated for these two insecticides, indicating potential local extinction of the wasp populations. Among the tested products, Bt proved to be the safest for B. nigricans adults and pupae. Our findings emphasize that acute toxicity assessment alone cannot fully predict the actual impact of pesticides on non-target parasitoids. Thus, sublethal effects related to the species specific life-history variables

  12. Sensitivity of Eisenia andrei (Annelida, Oligochaeta) to a commercial formulation of abamectin in avoidance tests with artificial substrate and natural soil under tropical conditions.

    PubMed

    Nunes, Maria Edna Tenório; Espíndola, Evaldo Luiz Gaeta

    2012-05-01

    Obtaining ecotoxicological data on pesticides in tropical regions is imperative for performing more realistic risk analysis, and avoidance tests have been proposed as a useful, fast and cost-effective tool. Therefore, the present study aimed to evaluate the avoidance behavior of Eisenia andrei to a formulated product, Vertimec® 18 EC (a.i abamectin), in tests performed on a reference tropical artificial soil (TAS), to derive ecotoxicological data on tropical conditions, and a natural soil (NS), simulating crop field conditions. In TAS tests an adaptation of the substrate recommended by OECD and ISO protocols was used, with residues of coconut fiber as a source of organic matter. Concentrations of the pesticide on TAS test ranged from 0 to 7 mg abamectin/kg (dry weight-d.w.). In NS tests, earthworms were exposed to samples of soils sprayed in situ with: 0.9 L of Vertimec® 18 EC/ha (RD); twice as much this dosage (2RD); and distilled water (Control), respectively, and to 2RD: control dilutions (12.5, 25, 50, 75%). All tests were performed under 25 ± 2°C, to simulate tropical conditions, and a 12hL:12hD photoperiod. The organisms avoided contaminated TAS for an EC(50,48h) = 3.918 mg/kg soil d.w., LOEC = 1.75 mg/kg soil d.w. and NOEC = 0.85 mg/kg soil d.w. No significant avoidance response occurred for any NS test. Abamectin concentrations in NS were rather lower than EC(50, 48h) and LOEC determined in TAS tests. The results obtained contribute to overcome a lack of ecotoxicological data on pesticides under tropical conditions, but more tests with different soil invertebrates are needed to improve pesticides risk analysis.

  13. Expression, purification and kinetic characterization of recombinant benzoate dioxygenase from Rhodococcus ruber UKMP-5M

    PubMed Central

    Tavakoli, Arezoo; Hamzah, Ainon; Rabu, Amir

    2016-01-01

    In this study, benzoate dioxygenase from Rhodococcus ruber UKMP-5M was catalyzed by oxidating the benzene ring to catechol and other derivatives. The benzoate dioxygenase (benA gene) from Rhodococcus ruber UKMP-5M was then expressed, purified, characterized, The benA gene was amplified (642 bp), and the product was cloned into a pGEM-T vector. The recombinant plasmid pGEMT-benA was digested by double restriction enzymes BamHI and HindIII to construct plasmid pET28b-benA and was then ligated into Escherichia coli BL21 (DE3). The recombinant E. coli was induced with 0.5 mM isopropyl β-D-thiogalactoside (IPTG) at 22˚C to produce benzoate dioxygenase. The enzyme was then purified by ion exchange chromatography after 8 purification folds. The resulting product was 25 kDa, determined by sodium dodecyl sulphate polyacrylamide gel electrophoresis (SDS-PAGE) and western blotting. Benzoate dioxygenase activity was found to be 6.54 U/mL and the optimal pH and temperature were 8.5 and 25°C, respectively. Maximum velocity (Vmax) and Michaelis constant (Km) were 7.36 U/mL and 5.58 µM, respectively. The end metabolite from the benzoate dioxygenase reaction was cyclohexane dione, which was determined by gas chromatography mass spectrometry (GC-MS). PMID:28097167

  14. [Clinico-immunological study of 16 cases of benzoate intolerance in children].

    PubMed

    Pétrus, M; Bonaz, S; Causse, E; Micheau, P; Rhabbour, M; Netter, J C; Bildstein, G

    1997-02-01

    The authors report a sery of 16 cases of intolerance to the benzoates in children. Sixteen children (9 boys and 7 girls) were directed to the Hospital of Tarbes from June 1995 to July 1995, for recurring urticaria (7/16) combined with asthma (1/16), atopic eczema (2/16), dermorespiratory syndrome (2/16) and asthma (1/16). All were subject to an immunological examination comprising alimentation inquiry, prick test, IgE determination, RAST, oral provocation test to benzoates, which establishes the diagnosis, whose confirmation is certified by the benefit of the food eviction. To conclusion, the authors underline several points: the presumable underestimation of the intolerance, the often mentioned atopic familial context, the observed pathology (urticaria, asthma, eczema), the importance of the provocation test. Finally, besides food such as grey shrimps, sodas and antibiotic syrups, one finds benzoates in the antiallergic syrups initially prescribed as a preventive measure.

  15. Genome-scale analysis of anaerobic benzoate and phenol metabolism in the hyperthermophilic archaeon Ferroglobus placidus

    PubMed Central

    Holmes, Dawn E; Risso, Carla; Smith, Jessica A; Lovley, Derek R

    2012-01-01

    Insight into the mechanisms for the anaerobic metabolism of aromatic compounds by the hyperthermophilic archaeon Ferroglobus placidus is expected to improve understanding of the degradation of aromatics in hot (>80° C) environments and to identify enzymes that might have biotechnological applications. Analysis of the F. placidus genome revealed genes predicted to encode enzymes homologous to those previously identified as having a role in benzoate and phenol metabolism in mesophilic bacteria. Surprisingly, F. placidus lacks genes for an ATP-independent class II benzoyl-CoA (coenzyme A) reductase (BCR) found in all strictly anaerobic bacteria, but has instead genes coding for a bzd-type ATP-consuming class I BCR, similar to those found in facultative bacteria. The lower portion of the benzoate degradation pathway appears to be more similar to that found in the phototroph Rhodopseudomonas palustris, than the pathway reported for all heterotrophic anaerobic benzoate degraders. Many of the genes predicted to be involved in benzoate metabolism were found in one of two gene clusters. Genes for phenol carboxylation proceeding through a phenylphosphate intermediate were identified in a single gene cluster. Analysis of transcript abundance with a whole-genome microarray and quantitative reverse transcriptase polymerase chain reaction demonstrated that most of the genes predicted to be involved in benzoate or phenol metabolism had higher transcript abundance during growth on those substrates vs growth on acetate. These results suggest that the general strategies for benzoate and phenol metabolism are highly conserved between microorganisms living in moderate and hot environments, and that anaerobic metabolism of aromatic compounds might be analyzed in a wide range of environments with similar molecular targets. PMID:21776029

  16. Evaluation of media for enumerating heat-stressed, benzoate-resistant Zygosaccharomyces bailii.

    PubMed

    Makdesi, A K; Beuchat, L R

    1996-12-01

    A study was undertaken to determine the efficacy of yeast malt extract agar (YMA), acidified YMA (YMAA), acidified tryptone glucose yeast extract agar (TGYA) and Zygosaccharomyces bailii agar (ZBA) for enumerating two strains of Z. bailii (FRR 2227 and FRR 3680) grown and heated in blueberry syrup containing 0, 300 and 600 micrograms/ml sodium benzoate. Cells were heated at 50, 51 or 52 degrees C for 0, 15, 30 or 45 min before spread plating diluted samples on enumeration media and incubating at 30 degrees C for 5 days. Strain FRR 3680 exhibited higher heat resistance than did strain FRR 2227. Regardless of the sodium benzoate concentration in growth and heating media, or the temperature and time of heating, non-selective YMA supported recovery of the highest number of viable cells, followed by TGYA for strain FRR 2227 and TGYA or ZBA for strain FRR 3680. YMAA supported the lowest recovery of heat-stressed cells. The concentration of sodium benzoate in the growth medium did not have a significant effect on tolerance of strain FRR 3680 to heat; however, tolerance of strain FRR 2227 to heat decreased when cells were grown in blueberry syrup containing increased concentrations of sodium benzoate. Regardless of the sodium benzoate concentration in the growth medium, both strains exhibited increased sensitivity when heated in blueberry syrup containing increased concentrations of sodium benzoate. Overall, TGYA was judged best among selective media for enumerating Z. bailii because of its ability to support colony development by heat-stressed cells and because of the ease of counting and differentiating colonies.

  17. 2-Amino-4-methyl­pyridinium 4-amino­benzoate

    PubMed Central

    Shen, Hong; Nie, Jing-Jing; Xu, Duan-Jun

    2008-01-01

    In the structure of the title salt, C6H9N2 +·C7H6NO2 −, the 4-amino­benzoate anions are linked to adjacent anions and 2-amino-4-methyl­pyridinium cations via N—H⋯O hydrogen bonds, forming a three-dimensional supra­molecular structure. The crystal structure also shows a weak C—H⋯O hydrogen bond between adjacent anions. Within the 4-amino­benzoate anion, the carboxyl­ate group is twisted by 14.0 (4)° with respect to the benz­ene ring. PMID:21202640

  18. Hyperargininemia: clinical course and treatment with sodium benzoate and phenylacetic acid.

    PubMed

    Mizutani, N; Maehara, M; Hayakawa, C; Kato, T; Watanabe, K; Suzuki, S

    1983-01-01

    In a patient with hyperargininemia, oral administration of sodium benzoate or phenylacetic acid together with an essential amino acid mixture was used to prevent hyperammonemia and to decrease plasma and CSF concentrations of arginine. Sodium benzoate reduced the plasma ammonia levels, which was confirmed by the increase of urinary excretion of hippuric acid. Phenylacetic acid also controlled hyperammonemia, and EEG findings also improved. By these treatments, plasma and CSF concentrations of arginine showed a slight decrease, but were far above the normal range. There was no clinical improvement, and spasticity of the lower and upper extremities was progressive with mental deterioration.

  19. Conductive iron oxide minerals accelerate syntrophic cooperation in methanogenic benzoate degradation.

    PubMed

    Zhuang, Li; Tang, Jia; Wang, Yueqiang; Hu, Min; Zhou, Shungui

    2015-08-15

    Recent studies have suggested that conductive iron oxide minerals can facilitate syntrophic metabolism of the methanogenic degradation of organic matter, such as ethanol, propionate and butyrate, in natural and engineered microbial ecosystems. This enhanced syntrophy involves direct interspecies electron transfer (DIET) powered by microorganisms exchanging metabolic electrons through electrically conductive minerals. Here, we evaluated the possibility that conductive iron oxides (hematite and magnetite) can stimulate the methanogenic degradation of benzoate, which is a common intermediate in the anaerobic metabolism of aromatic compounds. The results showed that 89-94% of the electrons released from benzoate oxidation were recovered in CH4 production, and acetate was identified as the only carbon-bearing intermediate during benzoate degradation. Compared with the iron-free controls, the rates of methanogenic benzoate degradation were enhanced by 25% and 53% in the presence of hematite and magnetite, respectively. This stimulatory effect probably resulted from DIET-mediated methanogenesis in which electrons transfer between syntrophic partners via conductive iron minerals. Phylogenetic analyses revealed that Bacillaceae, Peptococcaceae, and Methanobacterium are potentially involved in the functioning of syntrophic DIET. Considering the ubiquitous presence of iron minerals within soils and sediments, the findings of this study will increase the current understanding of the natural biological attenuation of aromatic hydrocarbons in anaerobic environments.

  20. Enzyme-catalysed synthesis and reactions of benzene oxide/oxepine derivatives of methyl benzoates.

    PubMed

    Boyd, Derek R; Sharma, Narain D; Harrison, John S; Malone, John F; McRoberts, W Colin; Hamilton, John T G; Harper, David B

    2008-04-07

    A series of twelve benzoate esters was metabolised, by species of the Phellinus genus of wood-rotting fungi, to yield the corresponding benzyl alcohol derivatives and eight salicylates. The isolation of a stable oxepine metabolite, from methyl benzoate, allied to evidence of the migration and retention of a carbomethoxy group (the NIH Shift), during enzyme-catalysed ortho-hydroxylation of alkyl benzoates to form salicylates, is consistent with a mechanism involving an initial arene epoxidation step. This mechanism was confirmed by the isolation of a remarkably stable, optically active, substituted benzene oxide metabolite of methyl 2-(trifluoromethyl)benzoate, which slowly converted into the racemic form. The arene oxide was found to undergo a cycloaddition reaction with 4-phenyl-1,2,4-triazoline-3,5-dione to yield a crystalline cycloadduct whose structure and racemic nature was established by X-ray crystallography. The metabolite was also found to undergo some novel benzene oxide reactions, including epoxidation to give an anti-diepoxide, base-catalysed hydrolysis to form a trans-dihydrodiol and acid-catalysed aromatisation to yield a salicylate derivative via the NIH Shift of a carbomethoxy group.

  1. Effects of sodium benzoate on storage stability of previously improved beverage from tamarind (Tamarindus indica L.)

    PubMed Central

    Adeola, Abiodun A; Aworh, Ogugua C

    2014-01-01

    The effect of sodium benzoate on the quality attributes of improved tamarind beverage during storage was investigated. Tamarind beverages were produced according to a previously reported improved method, with or without chemical preservatives (100 mg/100 mL sodium benzoate). Tamarind beverage produced according to traditional processing method served as the control. The tamarind beverages were stored for 4 months at room (29 ± 2°C) and refrigerated (4–10°C) temperatures. Samples were analyzed, at regular intervals, for chemical, sensory, and microbiological qualities. Appearance of coliforms or overall acceptability score of 5.9 was used as deterioration index. The control beverages deteriorated by 2nd and 10th days at room and refrigerated temperatures, respectively. Improved tamarind beverage produced without the inclusion of sodium benzoate was stable for 3 and 5 weeks at room and refrigerated temperatures, respectively. Sodium benzoate extended the shelf life of the improved tamarind beverage to 6 and 13 weeks, respectively, at room and refrigerated temperatures. PMID:24804061

  2. Mechanisms for aqueous photolysis of adsorbed benzoate, oxalate, and succinate on iron oxyhydroxide (goethite) surfaces

    USGS Publications Warehouse

    Cunningham, K.M.

    1988-01-01

    Photolysis of carboxylate anions adsorbed onto highly crystalline goethite (??-FeOOH) with 300-400-nm light produces Fe2+(aq) and ??OH from surface and solution redox reactions. The production of Fe2+(aq) and ??OH was studied in N2-purged and aerated aqueous suspensions, respectively, of goethite containing equimolar (10-3 M) concentrations of oxalate and benzoate (ob + g), succinate and benzoate (sb + g), benzoate alone (b + g), and goethite alone (g). The hydroxyl radical was measured by fluorescence analysis of salicylate formed in a reaction between benzoate and ??OH. Fe2+(aq) was determined colorimetrically. A proposed reaction mechanism includes the photoexcitation of Fe(III) surface complexes with OH-, HCO3-, and RCOO- ligands to form Fe2+(aq) and corresponding ligand radicals. Additional ??OH is made by the O2 oxidation of Fe2+(aq) (Haber-Weiss mechanism). Comparison of Fe2+(aq) and ??OH yields permitted an estimate of the relative importance of pathways leading to ??OH.

  3. Benzoate-induced stress enhances xylitol yield in aerobic fed-batch culture of Candida mogii TISTR 5892.

    PubMed

    Wannawilai, Siwaporn; Sirisansaneeyakul, Sarote; Chisti, Yusuf

    2015-01-20

    Production of the natural sweetener xylitol from xylose via the yeast Candida mogii TISTR 5892 was compared with and without the growth inhibitor sodium benzoate in the culture medium. Sodium benzoate proved to be an uncompetitive inhibitor in relatively poorly oxygenated shake flask aerobic cultures. In a better controlled aerobic environment of a bioreactor, the role of sodium benzoate could equally well be described as competitive, uncompetitive or noncompetitive inhibitor of growth. In intermittent fed-batch fermentations under highly aerobic conditions, the presence of sodium benzoate at 0.15gL(-1) clearly enhanced the xylitol titer relative to the control culture without the sodium benzoate. The final xylitol concentration and the average xylitol yield on xylose were nearly 50gL(-1) and 0.57gg(-1), respectively, in the presence of sodium benzoate. Both these values were substantially higher than reported for the same fermentation under microaerobic conditions. Therefore, a fed-batch aerobic fermentation in the presence of sodium benzoate is promising for xylitol production using C. mogii.

  4. Effect of sodium benzoate preservative on micronucleus induction, chromosome break, and Ala40Thr superoxide dismutase gene mutation in lymphocytes.

    PubMed

    Pongsavee, Malinee

    2015-01-01

    Sodium benzoate is food preservative that inhibits microbial growth. The effects of sodium benzoate preservative on micronucleus induction, chromosome break, and Ala40Thr superoxide dismutase gene mutation in lymphocytes were studied. Sodium benzoate concentrations of 0.5, 1.0, 1.5, and 2.0 mg/mL were treated in lymphocyte cell line for 24 and 48 hrs, respectively. Micronucleus test, standard chromosome culture technique, PCR, and automated sequencing technique were done to detect micronucleus, chromosome break, and gene mutation. The results showed that, at 24- and 48-hour. incubation time, sodium benzoate concentrations of 1.0, 1.5, and 2.0 mg/mL increased micronucleus formation when comparing with the control group (P < 0.05). At 24- and 48-hour. incubation time, sodium benzoate concentrations of 2.0 mg/mL increased chromosome break when comparing with the control group (P < 0.05). Sodium benzoate did not cause Ala40Thr (GCG→ACG) in superoxide dismutase gene. Sodium benzoate had the mutagenic and cytotoxic toxicity in lymphocytes caused by micronucleus formation and chromosome break.

  5. Physiological adaptation of Corynebacterium glutamicum to benzoate as alternative carbon source - a membrane proteome-centric view.

    PubMed

    Haussmann, Ute; Qi, Su-Wei; Wolters, Dirk; Rögner, Matthias; Liu, Shuang-Jiang; Poetsch, Ansgar

    2009-07-01

    The ability of microorganisms to assimilate aromatic substances as alternative carbon sources is the basis of biodegradation of natural as well as industrial aromatic compounds. In this study, Corynebacterium glutamicum was grown on benzoate as sole carbon and energy source. To extend the scarce knowledge about physiological adaptation processes occurring in this cell compartment, the membrane proteome was investigated under quantitative and qualitative aspects by applying shotgun proteomics to reach a comprehensive survey. Membrane proteins were relatively quantified using an internal standard metabolically labeled with (15)N. Altogether, 40 proteins were found to change their abundance during growth on benzoate in comparison to glucose. A global adaptation was observed in the membrane of benzoate-grown cells, characterized by increased abundance of proteins of the respiratory chain, by a starvation response, and by changes in sulfur metabolism involving the regulator McbR. Additional to the relative quantification, stable isotope-labeled synthetic peptides were used for the absolute quantification of the two benzoate transporters of C. glutamicum, BenK and BenE. It was found that both transporters were expressed during growth on benzoate, suggesting that both contribute substantially to benzoate uptake.

  6. Growth and studies of cyclohexylammonium 4-methoxy benzoate single crystal for nonlinear optical applications

    SciTech Connect

    Sathya, P.; Gopalakrishnan, R.

    2015-06-24

    Cyclohexylammonium 4-Methoxy Benzoate (C4MB) was synthesised and the functional groups were confirmed by FTIR analysis. The purified C4MB (by repeated recrystallisation) was used for single crystal growth. Single crystal of cyclohexylammonium 4-methoxy benzoate was successfully grown by slow evaporation solution growth method at ambient temperature. Structural orientations were determined from single crystal X-ray diffractometer. Optical absorption and cut off wavelength were identified by UV-Visible spectroscopy. Thermal stability of the crystal was studied from thermogravimetric and differential thermal analyses curves. Mechanical stability of the grown crystal was analysed by Vicker’s microhardness tester. The Second Harmonic Generation (SHG) study revealed that the C4MB compound exhibits the SHG efficiency 3.3 times greater than KDP crystal.

  7. Metabolic effects of benzoate and sorbate in the yeast Saccharomyces cerevisiae at neutral pH.

    PubMed

    Burlini, N; Pellegrini, R; Facheris, P; Tortora, P; Guerritore, A

    1993-01-01

    Preincubation of yeast cells in the presence of benzoate or sorbate at an extracellular pH value of 6.8 elicited a set of metabolic effects on sugar metabolism, which became apparent after the subsequent glucose addition. They can be summarized as follows: a) reduced glucose consumption; b) inhibition of glucose- and fructose-phosphorylating activities; c) suppression of glucose-triggered peak of hexoses monophosphates; d) substantial reduction of glucose-triggered peak of fructose 2,6-bisphosphate; e) block of catabolite inactivation of fructose-1,6-bisphosphatase and phosphoenolpyruvate carboxy-kinase, but not of cytoplasmic malate dehydrogenase. On the whole this pattern resulted in prevention of glucose-induced switch of metabolism from a gluconeogenetic to a glycolytic state. Our data also show that, unlike former assumptions, intracellular acidification is not likely to mediate the bulk of metabolic effects of benzoate and sorbate, since under our working conditions intracellular pH kept close to neutrality.

  8. Growth and studies of cyclohexylammonium 4-methoxy benzoate single crystal for nonlinear optical applications

    NASA Astrophysics Data System (ADS)

    Sathya, P.; Gopalakrishnan, R.

    2015-06-01

    Cyclohexylammonium 4-Methoxy Benzoate (C4MB) was synthesised and the functional groups were confirmed by FTIR analysis. The purified C4MB (by repeated recrystallisation) was used for single crystal growth. Single crystal of cyclohexylammonium 4-methoxy benzoate was successfully grown by slow evaporation solution growth method at ambient temperature. Structural orientations were determined from single crystal X-ray diffractometer. Optical absorption and cut off wavelength were identified by UV-Visible spectroscopy. Thermal stability of the crystal was studied from thermogravimetric and differential thermal analyses curves. Mechanical stability of the grown crystal was analysed by Vicker's microhardness tester. The Second Harmonic Generation (SHG) study revealed that the C4MB compound exhibits the SHG efficiency 3.3 times greater than KDP crystal.

  9. Developmental toxicity of benzyl benzoate in rats after maternal exposure throughout pregnancy.

    PubMed

    Koçkaya, E Arzu; Kılıç, Aysun

    2014-01-01

    The maternal and fetal toxicity of benzyl benzoate, commonly used as antiparasitic insecticide, was evaluated in pregnant rats after a daily oral dose of 25 and 100 mg/kg. Biochemical, histopathological, and morphological examinations were performed. Dams were observed for maternal body weights and food and water consumption and subjected to caesarean section on (GD) 20. Maternal and fetal liver, kidney, heart, brain, and placenta were examined histopathologically under light microscope. Maternal and fetal liver and placenta were stained immunohistochemically for vascular endothelial growth factor (VEGF). Morphometric analysis of fetal body lengths, placental measurements, and fetal skeletal stainings was performed. Statistically significant alterations in biochemical parameters and placental and skeletal measurements were determined in treatment groups. In addition to histopathological changes, considerable differences were observed in the immunolocalization of VEGF in treatment groups. These results demonstrated that benzyl benzoate and its metabolites can transport to the placenta and eventually enter the fetuses.

  10. Comparison of ivermectin and benzyl benzoate lotion for scabies in Nigerian patients.

    PubMed

    Sule, Halima M; Thacher, Tom D

    2007-02-01

    Few studies have compared ivermectin directly with topical agents in developing countries. We compared the effectiveness of oral ivermectin (200 microg/kg) with topical 25% benzyl benzoate and monosulfiram soap in 210 subjects of age 5 to 65 years with scabies. Subjects with persistent lesions after 2 weeks received a second course of treatment. All lesions had resolved after 2 weeks in 77 of 98 (79%) subjects treated with ivermectin and in 60 of 102 (59%) subjects treated topically (P = 0.003). The improvement in severity score was greater in the ivermectin group than in the topical treatment group (P < 0.001). The overall cure rate after 4 weeks was 95% in the ivermectin group and 86% in the topical treatment group (P = 0.04). Compared with topical benzyl benzoate and monosulfiram in the treatment of scabies, ivermectin was at least as effective and led to more rapid improvement.

  11. Bacteria and acid drainage from coal refuse: inhibition by sodium lauryl sulphate and sodium benzoate

    SciTech Connect

    Dugan, P.R.; Apel, W.A.

    1983-01-01

    Studies have shown that the application of an aqueous solution of sodium lauryl sulphate and sodium benzoate to the surface of high-sulphur coal refuse inhibits the activity of iron- and sulphur-oxidising chemo-autotrophic bacteria and reduces the amount of acid drainage from the refuse. Further studies are recommended to assess the usefulness of this method for controlling formation of acid mine drainage in the field.

  12. Synthesis, structure and some properties of a manganese(II) benzoate containing diimine

    NASA Astrophysics Data System (ADS)

    Paul, Pranajit; Roy, Subhadip; Sarkar, Sanjoy; Chowdhury, Shubhamoy; Purkayastha, R. N. Dutta; Raghavaiah, Pallepogu; McArdle, Patrick; Deb, Lokesh; Devi, Sarangthem Indira

    2015-12-01

    A new monomeric manganese(II) benzoate complex containing nitrogen donor 2,2‧-bipyridine, [Mn(OBz)2(bipy)(H2O)] (OBz = benzoate, bipy = 2,2‧-bipyridine) has been synthesized from aqueous methanol medium and characterized by analytical, spectroscopic and single crystal X-ray diffraction studies. The compound exhibits moderate to appreciable antimicrobial activity. The complex crystallizes in space group P21/n. Mn(II) atom is ligated by two N atoms of bipyridine, three O atoms from a monodentate and a bidentate benzoate ligand and a water molecule forming distorted octahedral structure. The coordinated water molecule forms intramolecular hydrogen bonds and links the monomer molecules into hydrogen bonded dimer. The hydrogen bonded dimers are involved in intermolecular C-H···O and π-π stacking interactions. Density functional theory (DFT) computation was carried out to compute the frequencies of relevant vibrational modes and electronic properties, the results are in compliance with the experimentally obtained structural and spectral data.

  13. Copper(II) benzoate dimers coordinated by different linear alcohols - A systematic study of crystal structures

    NASA Astrophysics Data System (ADS)

    Katzsch, Felix; Münch, Alexander S.; Mertens, Florian O. R. L.; Weber, Edwin

    2014-05-01

    Three new copper(II) benzoates coordinated by 1-propanol, [Cu2(PhCOO)4(1-PrOH)2] [Cu2(PhCOO)4(H2O)2] (3), 1-butanol, [Cu2(PhCOO)4(1-BuOH)2] (4) and 1-pentanol, [Cu2(PhCOO)4(1-PentOH)2] (5) at the available metal coordination sites, have been prepared and investigated with reference to their X-ray crystal structures. In all cases, dimeric paddle-wheel complexes where two copper(II) ions are held together by four benzoates were found. Moreover, the complexes show 1-propanol and water (3), 1-butanol (4) and 1-pentanol (5) coordinated to the free coordination sites of the Cu(II) ions. The dimeric complex units are connected with each other by strong Osbnd H⋯O hydrogen bonds to form strands linked together via weaker Csbnd H⋯O and Csbnd H⋯π interactions. Comparative discussion including the redetermined crystal structures obtained from copper(II) benzoate in the presence of methanol (1) or ethanol (2) allows to draw argumentation regarding the coordination of linear alcohols in corresponding crystals of paddle-wheel complexes.

  14. Impact of runoff water from an experimental agricultural field applied with Vertimec® 18EC (abamectin) on the survival, growth and gill morphology of zebrafish juveniles.

    PubMed

    Novelli, Andréa; Vieira, Bruna Horvath; Braun, Andréa Simone; Mendes, Lucas Bueno; Daam, Michiel Adriaan; Espíndola, Evaldo Luiz Gaeta

    2016-02-01

    Edge-of-field waterbodies in tropical agroecosystems have been reported to be especially prone to pesticide contamination through runoff resulting from intensive irrigation practices and tropical rainfall. In the present study, the effects of runoff from an experimental agricultural field applied with Vertimec(®) 18EC (active ingredient: abamectin) on zebrafish were evaluated. To this end, the experimental field was applied with the Vertimec(®) 18EC dose recommended for strawberry crop in Brazil, whereas another field was treated with water only to serve as control. No effects of runoff water from either plot were recorded on survival. Water from the treated field led to increased growth and gill alterations. In general, these alterations were of the first and second degree, including proliferation of cells between the secondary lamellae, dilation at the lamellar apex, detachment of the respiratory epithelium and aneurism. These results confirm the high toxic potential of Vertimec(®) 18EC and provide evidence that environmental risks are likely to occur in areas subject to runoff containing this pesticide.

  15. The Electrical Properties for Phenolic Isocyanate-Modified Bisphenol-Based Epoxy Resins Comprising Benzoate Group.

    PubMed

    Lee, Eun Yong; Chae, Il Seok; Park, Dongkyung; Suh, Hongsuk; Kang, Sang Wook

    2016-03-01

    Epoxy resin has been required to have a low dielectric constant (D(k)), low dissipation factor (Df), low coefficient of thermal expansion (CTE), low water absorption, high mechanical, and high adhesion properties for various applications. A series of novel phenolic isocyanate-modified bisphenol-based epoxy resins comprising benzoate group were prepared for practical electronic packaging applications. The developed epoxy resins showed highly reduced dielectric constants (D(k)-3.00 at 1 GHz) and low dissipation values (Df-0.014 at 1 GHz) as well as enhanced thermal properties.

  16. 2-(4-Methyl­phen­yl)-2-oxoethyl 3-bromo­benzoate

    PubMed Central

    Khan, Imtiaz; Ibrar, Aliya; Korzański, Artur; Kubicki, Maciej

    2012-01-01

    The mol­ecule of the title compound, C16H13BrO3, is built of two approximately planar fragments, viz. 3-bromo­benzoate [maximum deviation = 0.055 (2) Å and 2-oxo-2-p-tolyl­ethyl [maximum deviation = 0.042 (2) Å], inclined by 46.51 (7)°. In the crystal, weak C—H⋯O hydrogen bonds and Br⋯Br contacts [3.6491 (7) Å] connect the mol­ecules into infinite layers parallel to (-221). PMID:23476275

  17. Three cases of intravenous sodium benzoate and sodium phenylacetate toxicity occurring in the treatment of acute hyperammonaemia.

    PubMed

    Praphanphoj, V; Boyadjiev, S A; Waber, L J; Brusilow, S W; Geraghty, M T

    2000-03-01

    Intravenous sodium benzoate and sodium phenylacetate have been used successfully in the treatment of acute hyperammonaemia in patients with urea cycle disorders. They provide alternative pathways for waste nitrogen disposal and help maintain nitrogen homeostasis. However, we report three patients with hyperammonaemia who received inappropriate doses of intravenous sodium benzoate and sodium phenylacetate that resulted in severe complications. Ambiguous medical prescriptions and inadequate cross-checking of drug dosage by physicians, nurses and pharmacists were the main causes of these incidents. All the patients presented with alteration in mental status, Kussmaul respiration and a partially compensated metabolic acidosis with an increased anion gap. Two patients developed cerebral oedema and hypotension and died. The third survived after haemodialysis. Plasma levels of benzoate and phenylacetate were excessively high. The possible mechanisms of toxicity, management and safety measures are discussed.

  18. Syntheses, structures and magnetisms of copper(II)-azido coordination compounds with p-substituted benzoates as coligands

    NASA Astrophysics Data System (ADS)

    Sun, Cuiyu; Yu, Nan; Bu, Huaitian; Sun, Ce; Bu, Huaiyu

    2016-01-01

    Employing p-substituted benzoates with electron-withdrawing/electron-donating groups as coligands, four copper-azido compounds, [Cu1.5(p-NO2-benzoate)(N3)2(H2O)]n (1), [Cu(p-NO2-benzoate)(N3)(H2O)]n (2), [Cu(p-OH-benzoate)(N3)(H2O)]n·nH2O (3) and [Cu(p-CH3-benzoate)(N3)]n (4), have been hydrothermally synthesized and structurally charactierized by single crystal X-ray diffraction. Structural analysis reveals that all compounds are composed of mixed EO-azido and syn-syn carboxylato-bridged Cu-N3/COO chains. Compound 1 features the alternating triple-bridged (μ-EO-N3)(μ-COO)(μ-H2O) and the double-bridged (EO-N3)2 modes. Both of 2 and 3 display the triple-bridged fashion (μ-EO-N3)(μ-COO)(μ-H2O). While 4 exhibits the double-bridged mode (μ-EO-N3)(μ-COO). Based on hydrogen-bonding interactions, Cu-N3/COO chains in 1-3 are further connected to form 3D supramolecular frameworks. As for compound 4, there are not hydrogen-bonding interactions when the p-CH3 substituted benzoate is employed as coligand. These compounds show intrachain ferromagnetic performance and different bulk properties. Remarkably, 1 features metamagnetism from antiferromagnetism to ferrimagnetism, while 3 reveals long-range ferromagnetic ordering between Cu(II) ions. Magneto-structural correlation has been also investigated.

  19. Biochemical Characterization of Inducible 'Reductase' Component of Benzoate Dioxygenase and Phthalate Isomer Dioxygenases from Pseudomonas aeruginosa strain PP4.

    PubMed

    Karandikar, Rohini; Badri, Abinaya; Phale, Prashant S

    2015-09-01

    The first step involved in the degradation of phthalate isomers (phthalate, isophthalate and terephthalate) is the double hydroxylation by respective aromatic-ring hydroxylating dioxygenases. These are two component enzymes consisting of 'oxygenase' and 'reductase' components. Soil isolate Pseudomonas aeruginosa strain PP4 degrades phthalate isomers via protocatechuate and benzoate via catechol 'ortho' ring cleavage pathway. Metabolic studies suggest that strain PP4 has carbon source-specific inducible phthalate isomer dioxygenase and benzoate dioxygenase. Thus, it was of interest to study the properties of reductase components of these enzymes. Reductase activity from phthalate isomer-grown cells was 3-5-folds higher than benzoate grown cells. In-gel activity staining profile showed a reductase activity band of R f 0.56 for phthalate isomer-grown cells as compared to R f 0.73 from benzoate-grown cells. Partially purified reductase components from phthalate isomer grown cells showed K m in the range of 30-40 μM and V max = 34-48 μmol min(-1) mg(-1). However, reductase from benzoate grown cells showed K m = 49 μM and V max = 10 μmol min(-1) mg(-1). Strikingly similar molecular and kinetic properties of reductase component from phthalate isomer-grown cells suggest that probably the same reductase component is employed in three phthalate isomer dioxygenases. However, reductase component is different, with respect to kinetic properties and zymogram analysis, from benzoate-grown cells when compared to that from phthalate isomer grown cells of PP4.

  20. Elicitor(s) in Sogatella furcifera (Horváth) causing the Japanese rice plant (Oryza sativa L.) to induce the ovicidal substance, benzyl benzoate.

    PubMed

    Yang, Jeong-Oh; Nakayama, Naoya; Toda, Kyohei; Tebayashi, Shinichi; Kim, Chul-Sa

    2013-01-01

    We elucidate the mechanism for inducing the production of ovicidal benzyl benzoate by Japonica rice varieties to kill eggs of the whitebacked planthopper, Sogatella furcifera (Horváth), lying in the rice plant. Even when subjected to physical damage by a needle or damage with water, the rice plant produced no benzyl benzoate. However, significant benzyl benzoate was produced when the plant was damaged with a methanol extract or homogenate of S. furcifera. The extract of the male did not induce the production of benzyl benzoate, but that of the female did. We concluded from these results that benzyl benzoate was induced by some elicitor(s) in the female of S. furcifera.

  1. Formulation of rizatriptan benzoate fast dissolving buccal films by emulsion evaporation technique

    PubMed Central

    Vidyadhara, Suryadevara; Sasidhar, Reddyvallam Lankapalli; Balakrishna, Thalamanchi; Vardhan, Malapolu Santha

    2015-01-01

    Aim: The present study deals with the formulation of fast dissolving films of Rizatriptan benzoate that is used for the treatment of Migraine. The concept of fast-dissolving drug delivery emerged from the desire to provide patient with more conventional means of taking their medication. Materials and Methods: In the present research work, various trials were carried out using film forming agents such as maltodextrin, gum karaya and xanthan gum to prepare an ideal film. Emulsion evaporation method was used for the preparation of films. The prepared films were evaluated for weight uniformity, drug content, film thickness, folding endurance, dispersion test and curling. The in vitro dissolution studies were carried out using simulated salivary fluid (pH 6.8 phosphate buffer). Results: About 97% of the drug was found to be released from the film within 10 min that is a desirable character for fast absorption. The drug excipient interaction studies carried out by differential scanning calorimetry analysis and Fourier transform infrared studies revealed that there were no major interactions between the drugs and excipients used for the preparation of films. Conclusion: Fast dissolving films of Rizatriptan benzoate prepared by emulsion evaporation technique were found to be suitable for eliciting better therapeutic effect in the treatment of migraine. PMID:25838995

  2. Factors influencing benzene formation from the decarboxylation of benzoate in liquid model systems.

    PubMed

    Medeiros Vinci, Raquel; De Meulenaer, Bruno; Andjelkovic, Mirjana; Canfyn, Michael; Van Overmeire, Ilse; Van Loco, Joris

    2011-12-28

    Benzene may occur in foods due to the oxidative decarboxylation of benzoate in the presence of hydroxyl radicals. This study investigated factors influencing benzene formation in liquid model systems. The type of buffer, other sources of hydroxyl radical formation in food (photo oxidation of riboflavin and lipid oxidation), transition metal ion concentrations, and the inhibitory effect of antioxidants were tested in benzoate containing model systems. Regarding the hydroxyl radical sources tested, the highest benzene formation was observed in light exposed model systems containing ascorbic acid, Cu(2+), and riboflavin in Na-citrate buffer (1250 ± 131 μg kg(-1)). In practice, it seems that the combination ascorbic acid/transition metal ion remains the biggest contributor to benzene formation in food. However, the concentration of Cu(2+) influences significantly benzene formation in such a system with highest benzene yields observed for Cu(2+) 50 μM (1400 μg kg(-1)). The presence of antioxidants with metal chelation or reduction properties could prevent completely benzene formation.

  3. Efficacy of systemic insecticides for protection of loblolly pine against southern pine engraver beetles (Coleoptera: Curculionidae: Scolytinae) and wood borers (Coleoptera: Cerambycidae).

    PubMed

    Grosman, Donald M; Upton, William W

    2006-02-01

    We evaluated the efficacy of the systemic insecticides dinotefuran, emamectin benzoate, fipronil, and imidacloprid for preventing attacks and brood production of southern pine engraver beetles (Coleoptera: Curculionidae: Scolytinae) and wood borers (Coleoptera: Cerambycidae) on standing, stressed trees and bolt sections of loblolly pine, Pinus taeda L., in eastern Texas. Emamectin benzoate significantly reduced the colonization success of engraver beetles and associated wood borers in both stressed trees and pine bolt sections. Fipronil was nearly as effective as emamectin benzoate in reducing insect colonization of bolts 3 and 5 mo after injection but only moderately effective 1 mo after injection. Fipronil also significantly reduced bark beetle-caused mortality of stressed trees. Imidacloprid and dinotefuran were ineffective in preventing bark beetle and wood borer colonization of bolts or standing, stressed trees. The injected formulation of emamectin benzoate was found to cause long vertical lesions in the sapwood-phloem interface at each injection point.

  4. Investigation on sodium benzoate release from poly(butylene adipate-co-terephthalate)/organoclay/sodium benzoate based nanocomposite film and their antimicrobial activity.

    PubMed

    Mondal, Dibyendu; Bhowmick, Biplab; Maity, Dipanwita; Mollick, Md Masud R; Rana, Dipak; Rangarajan, Vivek; Sen, Ramkrishna; Chattopadhyay, Dipankar

    2015-03-01

    Polymeric nanocomposites embedded with nontoxic antimicrobial agents have recently gained potential industrial significance, mainly for their applicability to preserve food quality and ensure safety. In this study, a poly(butylene adipate-co-terephthalate) (PBAT)/organoclay (CMMT) based nanocomposite film doped with sodium benzoate (SB) as antimicrobial agent was prepared by a solution mixing process. A homogenous dispersion of organoclay (cetyltrimethylammonium-modified montmorillonite [CMMT]) in PBAT matrix was observed by X-ray diffraction and transmission electron microscopy. PBAT/CMMT nanocomposite film showed higher barrier properties against water and methanol vapor compared to the PBAT film. The release of SB from PBAT and its nanocomposite film was measured and the relevant data were fitted to the Weibull model. The higher values of Weibull's shape factor and scale parameter as corroborated by experimental findings indicated faster rate of SB release from PBAT/CMMT/SB nanocomposite film, when compared to the pristine PBAT film. Bacterial inhibition studies were accomplished against 2 food pathogenic bacteria, Bacillus subtilis and Staphylococcus aureus, by determining the zone of inhibition and corresponding growth profiles. Both bacterial inhibition studies and growth profiles established that PBAT/CMMT/SB demonstrated better antimicrobial activity than PBAT/SB film. Therefore, PBAT/CMMT/SB nanocomposite film can be used for food packaging application as it showed good barrier properties and antimicrobial activity against food pathogenic bacteria.

  5. NEONATAL LOW- AND HIGH-DOSE EXPOSURE TO ESTRADIOL BENZOATE IN THE MALE RAT: I. EFFECTS ON THE PROSTATE GLAND

    EPA Science Inventory

    Neonatal Low- And High-Dose Exposure To Estradiol Benzoate In The Male Rat: 1. Effects On The Prostate Gland. Oliver Putz, Christian B. Schwartz, Steve Kim, Gerald A. LeBlanc Ralph L. Cooper, Gail S. Prins

    ABSTRACT
    Brief exposure of rats to high doses of natural estro...

  6. Growth response of Escherichia coli ATCC 35218 adapted to several concentrations of sodium benzoate and potassium sorbate.

    PubMed

    Santiesteban-López, N Angélica; Rosales, Mónica; Palou, Enrique; López-Malo, Aurelio

    2009-11-01

    Escherichia coli ATCC 35218 growth response was evaluated after repetitive cultivation in stepwise increasing antimicrobial agent concentrations (potassium sorbate or sodium benzoate) to observe its adaptation process to high weak-acid concentrations. The effect of antimicrobial (potassium sorbate or sodium benzoate) concentration (0 to 7,000 ppm) was tested using laboratory media. Cells adapted at 1,000 ppm were inoculated in media containing the same concentration of the antimicrobial; after that, cells were transferred to media containing a higher concentration, followed by repetitive cultivations. In every case, viable cells were determined by surface plating every hour up to 48 h. Logarithmic representations of survival or growing fraction were modeled using the Gompertz equation. Adapted and nonadapted cells were analyzed for plasmid presence as well as phosphofructokinase and succinate dehydrogenase activity. Bacterial growth was observed after adaptation processes in media formulated up to 7,000 ppm of potassium sorbate or sodium benzoate. Analyses of variance demonstrated that no significant difference (P > 0.05) in lag time or growth rate was observed among adapted cells cultured in media containing the studied concentrations for each of the antimicrobials tested. These results suggest that E. coli can be adapted to high weak-acid concentrations if the exposure is performed under sublethal conditions. Furthermore, there was demonstrated inhibition of the enzymes phosphofructokinase and succinate dehydrogenase by action of sodium benzoate and potassium sorbate, respectively. E. coli adaptation to antimicrobial agents was not related to plasmid presence but appears to be due to other action mechanisms.

  7. Food preservatives sodium benzoate and propionic acid and colorant curcumin suppress Th1-type immune response in vitro.

    PubMed

    Maier, Elisabeth; Kurz, Katharina; Jenny, Marcel; Schennach, Harald; Ueberall, Florian; Fuchs, Dietmar

    2010-07-01

    Food preservatives sodium benzoate and propionic acid and colorant curcumin are demonstrated to suppress in a dose-dependent manner Th1-type immune response in human peripheral blood mononuclear cells (PBMC) in vitro. Results show an anti-inflammatory property of compounds which however could shift the Th1-Th2-type immune balance towards Th2-type immunity.

  8. Ivermectin alone or in combination with benzyl benzoate in the treatment of human immunodeficiency virus-associated scabies.

    PubMed

    Alberici, F; Pagani, L; Ratti, G; Viale, P

    2000-05-01

    In order to establish a safe and reliable treatment for human immunodeficiency virus (HIV)-associated scabies, we have treated 60 episodes of scabies in this setting, occurring in 39 patients, with one of the following regimens: (i) topical treatment with benzyl benzoate solution; (ii) single-dose oral treatment with ivermectin alone; and (iii) combination therapy with benzyl benzoate solution and oral ivermectin, employing the same regimens as single-agent therapy. Patients were stratified according to the severity score of the disease and the outcome (eradication, relapse, failure). We found that both benzyl benzoate and ivermectin alone were quite effective in mild to moderate scabies, but they were both associated with an unacceptable rate of relapse and failure in severe or crusted scabies. In contrast, combined treatment produced an optimal rate of success, without significant treatment-related side-effects. Therefore, we consider that combination treatment with benzyl benzoate solution and oral ivermectin is preferable to single-agent therapy in crusted scabies occurring in HIV/acquired immune deficiency syndrome patients.

  9. Syntheses, structures and magnetisms of copper(II)–azido coordination compounds with p-substituted benzoates as coligands

    SciTech Connect

    Sun, Cuiyu; Yu, Nan; Bu, Huaitian; Sun, Ce; Bu, Huaiyu

    2016-01-15

    Employing p-substituted benzoates with electron-withdrawing/electron-donating groups as coligands, four copper–azido compounds, [Cu{sub 1.5}(p-NO{sub 2}-benzoate)(N{sub 3}){sub 2}(H{sub 2}O)]{sub n} (1), [Cu(p-NO{sub 2}-benzoate)(N{sub 3})(H{sub 2}O)]{sub n} (2), [Cu(p-OH-benzoate)(N{sub 3})(H{sub 2}O)]{sub n}·nH{sub 2}O (3) and [Cu(p-CH{sub 3}-benzoate)(N{sub 3})]{sub n} (4), have been hydrothermally synthesized and structurally charactierized by single crystal X-ray diffraction. Structural analysis reveals that all compounds are composed of mixed EO-azido and syn–syn carboxylato-bridged Cu-N{sub 3}/COO chains. Compound 1 features the alternating triple-bridged (μ-EO-N{sub 3})(μ-COO)(μ-H{sub 2}O) and the double-bridged (EO-N{sub 3}){sub 2} modes. Both of 2 and 3 display the triple-bridged fashion (μ-EO-N{sub 3})(μ-COO)(μ-H{sub 2}O). While 4 exhibits the double-bridged mode (μ-EO-N{sub 3})(μ-COO). Based on hydrogen-bonding interactions, Cu–N{sub 3}/COO chains in 1–3 are further connected to form 3D supramolecular frameworks. As for compound 4, there are not hydrogen-bonding interactions when the p-CH{sub 3} substituted benzoate is employed as coligand. These compounds show intrachain ferromagnetic performance and different bulk properties. Remarkably, 1 features metamagnetism from antiferromagnetism to ferrimagnetism, while 3 reveals long-range ferromagnetic ordering between Cu(II) ions. Magneto-structural correlation has been also investigated. - Graphical abstract: With p-substituted benzoates as coligands, copper–azido compounds were isolated and structrually, magnetically characterized. Magneto-structural correlation has been investigated in detail.

  10. Effect of sodium benzoate and sodium phenylacetate on brain serotonin turnover in the ornithine transcarbamylase-deficient sparse-fur mouse.

    PubMed

    Batshaw, M L; Hyman, S L; Coyle, J T; Robinson, M B; Qureshi, I A; Mellits, E D; Quaskey, S

    1988-04-01

    Herein we examine the effects of sodium benzoate and sodium phenylacetate on feeding and central serotonin turnover in a child with citrullinemia and in an animal model of congenital hyperammonemia, the ornithine transcarbamylase-deficient sparse-fur (spf/y) mouse. In the child, when the benzoate/phenylacetate dosage was increased from 200 to 375 mg/kg/day each, feeding decreased. There was an accumulation of benzoate and phenylacetate in blood and cerebrospinal fluid as well as an increased concentration of 5-hydroxyindoleacetic acid, a neurochemical marker for serotonin turnover, in cerebrospinal fluid. In the mouse, sodium benzoate had a biphasic effect on both plasma ammonium levels and brain serotonin turnover. Two percent oral benzoate was associated with an increase in ammonium level, while a 3% dose led to a decrease in ammonium. There was a similar effect on serotonin turnover noted in both the hyperammonemic spf/y and control CD-1/y mice. Sodium phenylacetate did not have a consistent effect on serotonin turnover. The mechanism by which benzoate increases brain serotonin turnover appears to involve competition with tryptophan for albumin binding sites. This results in increased free tryptophan in serum and brain. We speculate that some of the clinical symptoms of benzoate intoxication may be a consequence of altered serotonin turnover in the brain. We suggest that drug levels be monitored during therapy.

  11. BadR and BadM Proteins Transcriptionally Regulate Two Operons Needed for Anaerobic Benzoate Degradation by Rhodopseudomonas palustris

    PubMed Central

    Hirakawa, Hidetada; Hirakawa, Yuko; Greenberg, E. Peter

    2015-01-01

    The bacterium Rhodopseudomonas palustris grows with the aromatic acid benzoate and the alicyclic acid cyclohexanecarboxylate (CHC) as sole carbon sources. The enzymatic steps in an oxygen-independent pathway for CHC degradation have been elucidated, but it was unknown how the CHC operon (badHI aliAB badK) encoding the enzymes for CHC degradation was regulated. aliA and aliB encode enzymes for the conversion of CHC to cyclohex-1-enecarboxyl–coenzyme A (CHene-CoA). At this point, the pathway for CHC degradation merges with the pathway for anaerobic benzoate degradation, as CHene-CoA is an intermediate in both degradation pathways. Three enzymes, encoded by badK, badH, and badI, prepare and cleave the alicyclic ring of CHene-CoA to yield pimelyl-CoA. Here, we show that the MarR transcription factor family member, BadR, represses transcription of the CHC operon by binding near the transcription start site of badH. 2-Ketocyclohexane-1-carboxyl–CoA, an intermediate of CHC and benzoate degradation, interacts with BadR to abrogate repression. We also present evidence that the transcription factor BadM binds to the promoter of the badDEFGAB (Bad) operon for the anaerobic conversion of benzoate to CHene-CoA to repress its expression. Contrary to previous reports, BadR does not appear to control expression of the Bad operon. These data enhance our view of the transcriptional regulation of anaerobic benzoate degradation by R. palustris. PMID:25888170

  12. Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin.

    PubMed

    Di Loreto, H E; Czarnowski, J; dos Santos Afonso, M

    2002-10-01

    The cyclization of ethyl 2-(aminosulfonyl)benzoate (ASB) to give saccharin was investigated in aqueous solutions at pH between 5.2 and 9.5 and in the temperature range of 296.2-334.2 K. The initial concentration of the reactant was varied between 1.45 x 10(-5) and 3.86 x 10(-4) M. Ultraviolet spectroscopy was used to obtain the kinetic data. The reaction is acid catalyzed and follows pseudo-first-order kinetics. The experimental rate constant, k(obs), increases with temperature and pH. Its dependence on the temperature and pH is well described by: k(obs) = k1 [OH-] = [(2.52 +/- 0.9) x 10(16) exp(-20.2 +/- 1 kcalmol(-1)/RT) s(-1)][OH-] A mechanism is proposed and the half-life of ethyl ASB is calculated.

  13. 2-Amino-5-methyl­pyridinium 3-chloro­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Farhadikoutenaei, Abbas; Khalib, Nuridayanti Che; Arshad, Suhana; Razak, Ibrahim Abdul

    2012-01-01

    The 3-chloro­benzoate anion of the title salt, C6H9N2 +·C7H4ClO2 −, is nearly planar with a dihedral angle of 2.44 (13)° between the benzene ring and the carboxyl­ate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms of the anion via a pair of N—H⋯O hydrogen bonds with an R 2 2(8) ring motif, forming an approximately planar ion pair with a dihedral angle of 7.92 (5)° between the pyridinium and benzene rings. The ion pairs are further connected via N—H⋯O and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. PMID:23284506

  14. 2-Amino-5-methyl­pyridinium 4-methyl­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Farhadikoutenaei, Abbas; Arshad, Suhana; Razak, Ibrahim Abdul

    2013-01-01

    The 4-methyl­benzoate anion of the title salt, C6H9N2 +·C8H7O2 −, is nearly planar, with a dihedral angle of 6.26 (10)° between the benzene ring and the carboxyl­ate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms of the anion via a pair of N—H⋯O hydrogen bonds with an R 2 2(8) ring motif, forming an approximately planar ion pair with a dihedral angle of 9.63 (4)° between the pyridinium and benzene rings. The ion pairs are further connected via N—H⋯O and weak C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. PMID:23476474

  15. Some clinical observations on the effect of an implant of oestradiol benzoate in brood mares.

    PubMed

    Azzie, M A

    1975-10-01

    The clinical effects and therapeutic value of a 500 mg implant of oestradiol benzoate was observed in thirty-nine Thoroughbred brood mares showing various abnormalities of the ovary and/or the reproductive tract. Sixteen similarly affected, untreated mares acted as controls. The implant was inserted during the early part of the normal anoestrous period and was removed 6 to 10 weeks later. The conception rate among the treated group (59%) during the onset of the ensuing breeding season was significantly higher (P less than 0-02) than that in the control group. The value of this form of treatment in septic endometritis and as an anabolic aid in cases of immaturity is also discussed.

  16. 2-Amino-6-methyl­pyridinium 3-chloro­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Khalib, Nuridayanti Che; Arshad, Suhana; Razak, Ibrahim Abdul

    2013-01-01

    In the title salt, C6H9N2 +·C7H4ClO2 −, the 3-chloro­benzoate anion shows a whole-mol­ecule disorder over two positions with a refined occupancy ratio of 0.505 (4):0.495 (4). In the crystal, the cations and anions are linked via N—H⋯O hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R 2 2(8) and R 4 2(8) ring motifs. The crystal structure also features a π–π stacking inter­action between the pyridinium rings with a centroid–centroid distance of 3.8339 (9) Å. PMID:23476517

  17. 2-Amino-5-methyl­pyridinium 2-amino­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Farhadikoutenaei, Abbas; Khalib, Nuridayanti Che; Arshad, Suhana; Razak, Ibrahim Abdul

    2012-01-01

    In the 2-amino­benzoate anion of the title salt, C6H9N2 +·C7H6NO2 −, an intra­molecular N—H⋯O hydrogen bond is observed. The dihedral angle between the ring and the CO2 group is 8.41 (13)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms via a pair of N—H⋯O hydrogen bonds, forming an R 2 2(8) ring motif. The ion pairs are further connected via N—H⋯O hydrogen bonds, resulting in a donor–donor–acceptor–acceptor (DDAA) array of quadruple hydrogen bonds. The crystal structure also features a weak N—H⋯O hydrogen bond and a C—H⋯π inter­action, resulting in a three-dimensional network. PMID:23284507

  18. Phenylacetate and benzoate clearance in a hyperammonemic infant on sequential hemodialysis and hemofiltration.

    PubMed

    Bunchman, Timothy E; Barletta, Gina-Marie; Winters, John W; Gardner, John J; Crumb, Teri L; McBryde, Kevin D

    2007-07-01

    An infant with a suspected inborn metabolism error was treated with a metabolic cocktail of intravenous sodium phenylacetate (NaPh) and sodium benzoate (NaBz) for hyperammonemia. Sequential hemodialysis (HD) then hemofiltration (HF) was performed due to hyperammonemia. Dialytic and convective clearance (K; ml/min) of ammonia, NaPh, and NaBz was measured. The K of ammonia was 57 and 37 for HD and HF, respectively. The K of NaBz was 37 and 12 for HD and HF, respectively. The K of NaPh was 38 and 14 ml/min for HD and HF, respectively. Despite high clearance of both NaPh and NaBz by HD and HF, the hyperammonemia was corrected.

  19. A novel 3α-p-Nitrobenzoylmultiflora-7:9(11)-diene-29-benzoate and two new triterpenoids from the seeds of zucchini (Cucurbita pepo L).

    PubMed

    Tanaka, Reiko; Kikuchi, Takashi; Nakasuji, Saori; Ue, Yasuhiro; Shuto, Daisuke; Igarashi, Keishi; Okada, Rina; Yamada, Takeshi

    2013-06-26

    Three novel multiflorane-type triterpenoids, 3α-p-nitrobenzoylmultiflora-7:9(11)-diene-29-benzoate (1), 3α-acetoxymultiflora-7:9(11)-diene-29-benzoate (2), and 3α-acetoxymultiflora-5(6):7:9(11)-triene-29-benzoate (3), along with two known related compounds 4 and 5 were isolated from the seeds of zucchini (Cucurbita pepo L). Their structures were determined on the basis of 1D and 2D NMR spectroscopy and HREIMS. Triterpenoids possessing a nitro group were not isolated previously.

  20. Ligand sensitized luminescence of uranyl by benzoic acid in acetonitrile medium: a new luminescent uranyl benzoate specie.

    PubMed

    Kumar, Satendra; Maji, S; Joseph, M; Sankaran, K

    2015-03-05

    Benzoic acid (BA) is shown to sensitize and enhance the luminescence of uranyl ion in acetonitrile medium. Luminescence spectra and especially UV-Vis spectroscopy studies reveal the formation of tri benzoate complex of uranyl i.e. [UO2(C6H5COO)3](-) which is highly luminescent. In particular, three sharp bands at 431, 443, 461nm of absorption spectra provides evidence for tri benzoate specie of uranyl in acetonitrile medium. The luminescence lifetime of uranyl in this complex is 68μs which is much more compared to the lifetime of uncomplexed uranyl (20μs) in acetonitrile medium. In contrary to aqueous medium where uranyl benzoate forms 1:1 and 1:2 species, spectroscopic data reveal formation of 1:3 complex in acetonitrile medium. Addition of water to acetonitrile results in decrease of luminescence intensity of this specie and the luminescence features implode at 20% (v/v) of water content. For the first time, to the best of our knowledge, the existence of [UO2(C6H5COO)3](-) specie in acetonitrile is reported. Mechanism of luminescence enhancement is discussed.

  1. Adsorption of choline benzoate ionic liquid on graphene, silicene, germanene and boron-nitride nanosheets: a DFT perspective.

    PubMed

    García, Gregorio; Atilhan, Mert; Aparicio, Santiago

    2015-07-07

    The adsorption of choline benzoate ([CH][BE]) ionic liquid (IL) on the surface of different hexagonal nanosheets has been studied using Density Functional Theory (DFT) methods. For this, the interaction mechanism, binding energies and electronic structure of [CH][BE] ionic liquid on four types of nanosheets, i.e., graphene, silicene, germanene and boron-nitride, were estimated and compared. The adsorption of [CH][BE] ionic liquid on different nanosheets is mainly featured by van der Waals forces, leading to strong benzoate ion-surface π-stacking. Likewise, there is also an important charge transfer from the anion to the sheet. The electronic structure analysis shows that Si- and Ge-based sheets lead to the largest changes in the HOMO and LUMO levels of choline benzoate. This paper provides new insights into the capability of DFT methods to provide useful information about the adsorption of ionic liquids on nanosheets and how ionic liquid features could be tuned through the adsorption on the suitable nanosheet.

  2. Spectroscopic, optical, thermal, antimicrobial and density functional theory studies of 4-aminopyridinium 4-hydroxy benzoate hydrate crystal

    NASA Astrophysics Data System (ADS)

    Karthiga Devi, P.; Venkatachalam, K.; Poonkothai, M.

    2016-09-01

    The organic crystal 4-aminopyridinium 4-hydroxy benzoate hydrate was grown using slow evaporation method. Various characterization techniques such as single crystal X-ray diffraction, powder X-ray diffraction, FTIR, UV-visible-NIR spectroscopy and thermal analysis (TG-DSC) were employed to assay the structure and properties of the grown crystal. The antimicrobial evaluation of 4-aminopyridinium 4-hydroxy benzoate hydrate crystal was also performed against some bacteria and fungi. The minimum inhibitory concentration (MIC) values of 4-aminopyridinium 4-hydroxy benzoate hydrate were determined for bacterial and fungal strains. The assessment of optimized structure of the molecule and vibrational frequencies were done using DFT/B3LYP method with 6-31 G (d, p) basis set. The stability of the molecule, hyperconjugative interactions, delocalization of charges and intermolecular hydrogen bond were studied by applying natural bond orbital (NBO) analysis. TD-DFT method employing polarizable continuum model (PCM) was used to examine the electronic absorption spectrum. Evaluation of molecular electrostatic potential (MEP), Mulliken population charges and nonlinear optical (NLO) properties were also carried out. In addition, from the optimized geometry, frontier molecular orbitals analysis was executed.

  3. Effects of heat shocks on microbial community structure and microbial activity of a methanogenic enrichment degrading benzoate.

    PubMed

    Mei, R; Narihiro, T; Nobu, M K; Liu, W-T

    2016-11-01

    In anaerobic digesters, temperature fluctuation could lead to process instability and failure. It is still not well understood how digester microbiota as a whole respond to heat shock, and what specific organisms are vulnerable to perturbation or responsible for process recovery after perturbation. To address these questions, a mesophilic benzoate-degrading methanogenic culture enriched from digester was subjected to different levels of heat shock. Three types of methane production profiles after perturbation were observed in comparison to the control: uninhibited, inhibited with later recovery, and inhibited without recovery. These responses were correlated with the microbial community compositions based on the analyses of 16S rRNA and 16S rRNA gene. Specifically, the primary benzoate-degrading syntroph was highly affected by heat shock, and its abundance and activity were both crucial to the restoration of benzoate degradation after heat shock. In contrast, methanogens were stable regardless whether methane production was inhibited. Populations related to 'Candidatus Cloacimonetes' and Firmicutes showed stimulated growth. These observations indicated distinct physiological traits and ecological niches associated with individual microbial groups. The results obtained after exposure to heat shock can be critical to more comprehensive characterization of digester ecology under perturbations.

  4. Biosynthesis and emission of insect-induced methyl salicylate and methyl benzoate from rice

    SciTech Connect

    Zhao, Nan; Guan, Ju; Ferrer, Jean-Luc; Engle, Nancy L; Chern, Mawsheng; Ronald, Pamela; Tschaplinski, Timothy J; Chen, Feng

    2010-01-01

    Two benzenoid esters, methyl salicylate (MeSA) and methyl benzoate (MeBA), were detected from insect-damaged rice plants. By correlating metabolite production with gene expression analysis, five candidate genes encoding putative carboxyl methyltransferases were identified. Enzymatic assays with Escherichia coli-expressed recombinant proteins demonstrated that only one of the five candidates, OsBSMT1, has salicylic acid (SA) methyltransferase (SAMT) and benzoic acid (BA) methyltransferase (BAMT) activities for producing MeSA and MeBA, respectively. Whereas OsBSMT1 is phylogenetically relatively distant from dicot SAMTs, the three-dimensional structure of OsBSMT1, which was determined using homology-based structural modeling, is highly similar to those of characterized SAMTs. Analyses of OsBSMT1 expression in wild-type rice plants under various stress conditions indicate that the jasmonic acid (JA) signaling pathway plays a critical role in regulating the production and emission of MeSA in rice. Further analysis using transgenic rice plants overexpressing NH1, a key component of the SA signaling pathway in rice, suggests that the SA signaling pathway also plays an important role in governing OsBSMT1 expression and emission of its products, probably through a crosstalk with the JA signaling pathway. The role of the volatile products of OsBSMT1, MeSA and MeBA, in rice defense against insect herbivory is discussed.

  5. 2-Amino-5-methyl­pyridinium 4-chloro­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Farhadikoutenaei, Abbas; Arshad, Suhana; Razak, Ibrahim Abdul

    2013-01-01

    The 4-chloro­benzoate anion of the title salt, C6H9N2 +·C7H4ClO2 −, is nearly planar with a dihedral angle of 5.14 (16)° between the benzene ring and the carboxyl­ate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms of the anion via a pair of N—H⋯O hydrogen bonds with an R 2 2(8) ring motif. The ion pairs are further connected via N—H⋯O and weak C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. The crystal structure also features a π–π stacking inter­action between the pyridinium and benzene rings with a centroid–centroid distance of 3.7948 (9) Å. PMID:23476392

  6. Monitoring benzene formation from benzoate in model systems by proton transfer reaction-mass spectrometry

    NASA Astrophysics Data System (ADS)

    Aprea, Eugenio; Biasioli, Franco; Carlin, Silvia; Märk, Tilmann D.; Gasperi, Flavia

    2008-08-01

    The presence of benzene in food and in particular in soft drinks has been reported in several studies and should be considered in fundamental investigations about formation of this carcinogen compound as well as in quality control. Proton transfer reaction-mass spectrometry (PTR-MS) has been used here for rapid, direct quantification of benzene and to monitor its formation in model systems related to the use of benzoate, a common preservative, in presence of ascorbic acid: a widespread situation that yields benzene in, e.g., soft drinks and fruit juices. Firstly, we demonstrate here that PTR-MS allows a rapid determination of benzene that is in quantitative agreement with independent solid phase micro-extraction/gas chromatography (SPME/GC) analysis. Secondly, as a case study, the effect of different sugars (sucrose, fructose and glucose) on benzene formation is investigated indicating that they inhibit its formation and that this effect is enhanced for reducing sugars. The sugar-induced inhibition of benzene formation depends on several parameters (type and concentration of sugar, temperature, time) but can be more than 80% in situations that can be expected in the storage of commercial soft drinks. This is consistent with the reported observations of higher benzene concentrations in sugar-free soft drinks.

  7. Molecular modeling of layered double hydroxide intercalated with benzoate, modeling and experiment.

    PubMed

    Kovár, Petr; Pospísil, M; Nocchetti, M; Capková, P; Melánová, Klára

    2007-08-01

    The structure of Zn4Al2 Layered Double Hydroxide intercalated with benzencarboxylate (C6H5COO-) was solved using molecular modeling combined with experiment (X-ray powder diffraction, IR spectroscopy, TG measurements). Molecular modeling revealed the arrangement of guest molecules, layer stacking, water content and water location in the interlayer space of the host structure. Molecular modeling using empirical force field was carried out in Cerius(2) modeling environment. Results of modeling were confronted with experiment that means comparing the calculated and measured diffraction pattern and comparing the calculated water content with the thermogravimetric value. Good agreement has been achieved between calculated and measured basal spacing: d(calc) = 15.3 A and d(exp) = 15.5 A. The number of water molecules per formula unit (6H2O per Zn4Al2(OH)12) obtained by modeling (i.e., corresponding to the energy minimum) agrees with the water content estimated by thermogravimetry. The long axis of guest molecules are almost perpendicular to the LDH layers, anchored to the host layers via COO- groups. Mutual orientation of benzoate ring planes in the interlayer space keeps the parquet arrangement. Water molecules are roughly arranged in planes adjacent to host layers together with COO- groups.

  8. RIFM fragrance ingredient safety assessment, linalyl benzoate, CAS Registry Number 126-64-7.

    PubMed

    Api, A M; Belsito, D; Bhatia, S; Bruze, M; Calow, P; Dagli, M L; Dkant, W; Fryer, A D; Kromidas, L; La Cava, S; Lalko, J F; Lapczynski, A; Liebler, D C; Penning, T M; Politano, V T; Ritacco, G; Salvito, D; Schultz, T W; Shen, J; Sipes, I G; Wall, B; Wilcox, D K

    2016-11-01

    The use of this material under current conditions is supported by existing information. This material was evaluated for genotoxicity, repeated dose toxicity, developmental and reproductive toxicity, local respiratory toxicity, phototoxicity/photoallergenicity, skin sensitization, as well as environmental safety. Data show that this material is not genotoxic. Data from the suitable read across analog linalyl phenylacetate (CAS # 7143-69-3) show that this material does not have skin sensitization potential. The repeated dose toxicity endpoint was completed using linalyl cinnamate (CAS # 78-37-5) as a suitable read across analog, which provided a MOE > 100. The developmental and reproductive toxicity endpoint was completed using linalool (CAS # 78-70-6), dehydrolinalool (CAS # 29171-20-8), benzoic acid (CAS # 65-85-0) and sodium benzoate (CAS # 532-32-1) as suitable read across analogs, which provided a MOE > 100. The local respiratory toxicity endpoint was completed using linalool (CAS # 78-70-6) and benzoic acid (CAS # 65-85-0) as suitable read across analogs, which provided a MOE > 100. The phototoxicity/photoallergenicity endpoint was completed based on suitable UV spectra. The environmental endpoint was completed as described in the RIFM Framework along with data from the suitable read across analog linalyl cinnamate (CAS # 78-375).

  9. BadR, a new MarR family member, regulates anaerobic benzoate degradation by Rhodopseudomonas palustris in concert with AadR, an Fnr family member.

    PubMed

    Egland, P G; Harwood, C S

    1999-04-01

    A cluster of genes for the anaerobic degradation of benzoate has been described for the phototrophic bacterium Rhodopseudomonas palustris. Here we provide an initial analysis of the regulation of anaerobic benzoate degradation by examining the contributions of two regulators: a new regulator, BadR, encoded by the benzoate degradation gene cluster, and a previously described regulator, AadR, whose gene lies outside the cluster. Strains with single mutations in either badR or aadR grew slowly on benzoate but were relatively unimpaired in growth on succinate and several intermediates of benzoate degradation. A badR aadR double mutant was completely defective in anaerobic growth on benzoate. Effects of the regulators on transcriptional activation were monitored with an R. palustris strain carrying a chromosomal fusion of 'lacZ to the badE gene of the badDEFG operon. This operon encodes benzoyl-coenzyme A (benzoyl-CoA) reductase, an unusual oxygen-sensitive enzyme that catalyzes the benzene ring reduction reaction that is the rate-limiting step in anaerobic benzoate degradation. Expression of badE::'lacZ was induced 100-fold when cells grown aerobically on succinate were shifted to anaerobic growth on succinate plus benzoate. The aadR gene was required for a 20-fold increase in expression that occurred in response to anaerobiosis, and badR was responsible for a further 5-fold increase in expression that occurred in response to benzoate. Further studies with the badE::'lacZ fusion strain grown with various kinds of aromatic acids indicated that BadR probably responds to benzoyl-CoA acting as an effector molecule. Sequence information indicates that BadR is a member of the MarR family of transcriptional regulators. These studies expand the range of functions regulated by MarR family members to include anaerobic aromatic acid degradation and provide an example of a MarR-type protein that acts as a positive regulator rather than as a negative regulator, as do most Mar

  10. Complexation of U(VI) with benzoic acid at variable temperatures (298-353 K): thermodynamics and crystal structures of U(VI)/benzoate complexes.

    PubMed

    Yang, Yanqiu; Teat, Simon J; Zhang, Zhicheng; Luo, Shunzhong; Rao, Linfeng

    2016-01-07

    Thermodynamics of the U(VI) complexation with benzoic acid (HL) was studied by spectrophotometry at varied temperatures (298-353 K) with constant ionic strength (1.05 mol kg(-1) NaClO4). Two U(VI) benzoate complexes, UO2L(+) and UO2(OH)L(aq), were identified and their formation constants determined. The formation of both complexes is endothermic and driven exclusively by entropy. Two types of U(VI)/benzoate complex crystals were synthesized from aqueous solutions at different pH and ligand/metal ratios. Their structures were determined by single-crystal X-ray diffractometry. One structure is a 1 : 3 U(VI) benzoate complex (Na[UO2(C7H5O2)3]·2H2O), each benzoate holding a bidentate coordination mode to U(VI) in the equatorial plane of UO2(2+). The other is a U(VI) hydroxobenzoate complex with unique μ3-OH bridging ([(UO2)2(C7H5O2)2(μ3-OH)2]·4H2O). In the structure, each UO2(2+) ion holds five coordination oxygens in its equatorial plane, two carboxylate oxygens from two benzoate ligands and three oxygens from three μ3-OH groups.

  11. Effect of sulfate on anaerobic degradation of benzoate in UASB reactors

    SciTech Connect

    Fang, H.H.P.; Liu, Y.; Chen, T.

    1997-04-01

    Anaerobic processes have been widely used for the treatment of various high-strength industrial wastewaters. However, application has been limited for the treatment of sulfate-rich industrial wastewaters, such as those from the petrochemical, and mining industries. Wastewaters containing benzoate and sulfate were treated in two upflow anaerobic sludge blanket (UASB) reactors at 34--37 C for 320 d. The sulfate concentration was increased stepwise in Reactor-A up to 7,500 mg/L, and was kept mostly constant at 3,000 mg/L in Reactor-B. Both reactors removed over 98% of organic chemical-oxygen demand (COD) for sulfate up to 6,000 mg/L, despite the fact that the mixed liquor contained up to 769 mg S/L of total sulfides and up to 234 mg S/L of dissolved H{sub 2}S. Sulfate0reducing efficiency decreased with the increase in sulfate concentration, but increased with time at each sulfate concentration. Reactor-B consistently reduced 89% of sulfate. However, both organic COD removal and sulfate-reducing efficiencies of Reactor-A dropped drastically at 7,500 mg SO{sub 4}{sup {minus}2}/L, and showed no sign of recovery after 50 d. The system failure was likely due to the increased sulfate, instead of sulfide, toxicity. From the COD balance, 93.4% of COD removed was converted to methane instead of sulfides, with a net sludge yield of 0.047 g volatile suspended solids (VSS)/g COD. The sulfur balance was over 97%.

  12. Multivariate Optimization of Rizatriptan Benzoate-Loaded Solid Lipid Nanoparticles for Brain Targeting and Migraine Management.

    PubMed

    Girotra, Priti; Singh, Shailendra Kumar

    2017-02-01

    The present investigation aimed at development of brain-targeted rizatriptan benzoate-loaded solid lipid nanoparticles (RB-SLNs) by design of experiment, for improvement of its anti-migraine potential. Several formulation variables affecting the fabrication of RB-SLNs were screened using the Plackett-Burman design (PBD). The PBD results demonstrated lipid (Precirol® ATO 5) concentration, co-surfactant (Phospholipon® 90 H) concentration and temperature of lipid melt to be the critical variables, having a significant effect on the achievement of minimum particle size, maximum entrapment efficiency coupled with sustained drug release. The interactions between these formulation parameters and the variability between the batches were further explored employing the Box-Behnken design (BBD). The BBD results were validated by fabricating the suggested optimized solution, which yielded 220.4 ± 2.3 nm particle size with a sufficiently high entrapment efficiency of 71.8 ± 1.9% and 45.9 ± 2.7% cumulative drug release in 8 h. The optimized formulation was, thereafter, characterized by FTIR spectroscopy, wide angle XRD, thermal analysis and TEM imaging technique. The in vivo studies revealed the brain uptake potential of optimized RB-SLNs to be 18.43-folds higher with respect to the pure drug in its free form, post 2 h of oral drug administration. The significant anti-migraine efficacy of RB-SLNs was corroborated through the pharmacodynamic studies on adult male Swiss albino mice. The results hence explicate that RB-SLNs have distinctly improved brain target ability and offer an apt approach for the efficient therapeutic management of migraine.

  13. Intragastric infusion of denatonium benzoate attenuates interdigestive gastric motility and hunger scores in healthy female volunteers.

    PubMed

    Deloose, Eveline; Janssen, Pieter; Corsetti, Maura; Biesiekierski, Jessica; Masuy, Imke; Rotondo, Alessandra; Van Oudenhove, Lukas; Depoortere, Inge; Tack, Jan

    2017-03-01

    Background: Denatonium benzoate (DB) has been shown to influence ongoing ingestive behavior and gut peptide secretion.Objective: We studied how the intragastric administration of DB affects interdigestive motility, motilin and ghrelin plasma concentrations, hunger and satiety ratings, and food intake in healthy volunteers.Design: Lingual bitter taste sensitivity was tested with the use of 6 concentrations of DB in 65 subjects. A placebo or 1 μmol DB/kg was given intragastrically to assess its effect on fasting gastrointestinal motility and hunger ratings, motilin and ghrelin plasma concentrations, satiety, and caloric intake.Results: Women (n = 39) were more sensitive toward a lingual bitter stimulus (P = 0.005) than men (n = 26). In women (n = 10), intragastric DB switched the origin of phase III contractions from the stomach to the duodenum (P = 0.001) and decreased hunger ratings (P = 0.04). These effects were not observed in men (n = 10). In women (n = 12), motilin (P = 0.04) plasma concentrations decreased after intragastric DB administration, whereas total and octanoylated ghrelin were not affected. The intragastric administration of DB decreased hunger (P = 0.008) and increased satiety ratings (P = 0.01) after a meal (500 kcal) in 13 women without affecting gastric emptying in 6 women. Caloric intake tended to decrease after DB administration compared with the placebo (mean ± SEM: 720 ± 58 compared with 796 ± 45 kcal; P = 0.08) in 20 women.Conclusions: Intragastric DB administration decreases both antral motility and hunger ratings during the fasting state, possibly because of a decrease in motilin release. Moreover, DB decreases hunger and increases satiety ratings after a meal and shows potential for decreasing caloric intake. This trial was registered at clinicaltrials.gov as NCT02759926.

  14. Evaluation of Effects of Topical Estradiol Benzoate Application on Cutaneous Wound Healing in Ovariectomized Female Mice

    PubMed Central

    Mukai, Kanae; Urai, Tamae; Asano, Kimi; Nakajima, Yukari; Nakatani, Toshio

    2016-01-01

    Estrogen promotes cutaneous wound healing in ovariectomized (OVX) female mice. However, the effects of topical estrogen application on wounds remain unclear. Therefore, the aim of this study was to compare the effects of topical estrogen application on wounds with standard treatment methods. Eight-week-old C57BL/6J female mice underwent OVX and received two full-thickness wounds four weeks later. Mice were divided into three groups: topical estradiol benzoate (EB) (0.75 μg/g/day) wound treatment, subcutaneous estradiol (E2) pellets (0.05 mg, 21 days), and topical E2 (0.01 g/day) skin application. Wound healing was observed until day 14. Wound area ratios were significantly smaller in the topical EB wound treatment group than in the subcutaneous E2 pellet group on days 1–14 (p < 0.05) and topical E2 skin application group on days 1–9 (p < 0.05). Neutrophil and macrophage numbers were significantly smaller in the topical EB wound treatment group than in the subcutaneous E2 pellet and topical E2 skin application groups on day 7 (p < 0.05). Moreover, the number of new blood vessels and ratio of myofibroblasts were significantly larger in the topical EB wound treatment group than in the subcutaneous E2 pellet and topical E2 application skin groups on day 7 (p < 0.05). These results demonstrate that the application of estrogen to wounds reduced inflammatory responses and promoted angiogenesis and wound contraction more than the two other standard treatment methods. PMID:27658263

  15. Exogenous Estradiol Benzoate Induces Spermatogenesis Disorder through Influencing Apoptosis and Oestrogen Receptor Signalling Pathway.

    PubMed

    Lei, X; Cui, K; Liu, Q; Zhang, H; Li, Z; Huang, B; Shi, D

    2016-02-01

    As the exact role for exogenous oestrogen in spermatogenesis is not fully understood, the aim of this study was to investigate the effect of estradiol benzoate (EB) exposure to male mice on their spermatogenesis and fertility. Sixty male mice aged 4 weeks were randomly divided into three groups, including a control group and two treatment groups. The mice of the control group were injected with 250 μl paraffin oil only by every other day subcutaneous injection for 4 weeks. Meantime, the mice of the treatment groups were injected with EB at the concentration of 5 or 10 mg/kg, respectively. Results showed that EB slowed down the body weight gains and generated testicular atrophy with spermatogenesis disorder compared with that of the control mice, and consequently induced their infertility. Moreover, the number of TUNEL-positive cells in the testis of EB-treated mice was significantly increased with the EB concentration rise. In comparison with controls, the mRNA expression level of pro-apoptosis factors (Fas, TNF, Cytochrome C, Apaf1, Chop, Caspase-3, Caspase-8, Caspase-9 and Caspase-12) and key genes in oestrogen receptor (ER) signalling pathway (ER α, ER β, Erk1/2, Hsp90 and DAX-1) were upregulated in the testes of the treatment groups. Furthermore, Western blotting results proved the protein expression level of Fas, TNF, Cytochrome C, Chop, Caspase-3, cleaved Caspase-3, Caspase-9, Erk1/2 and Hsp90 were upregulated, and the phosphorylation level of Erk1/2 was also increased. These results indicate that EB may impair spermatogenesis through influencing the apoptosis and ER signalling pathway.

  16. Synthesis of Active Hexafluoroisopropyl Benzoates through a Hydrogen-Bond-Enabled Palladium(II)-Catalyzed C-H Alkoxycarbonylation Reaction.

    PubMed

    Wang, Yang; Gevorgyan, Vladimir

    2017-03-13

    A Pd(II) -catalyzed ortho C-H alkoxycarbonylation reaction of aryl silanes toward active hexafluoroisopropyl (HFIP) benzoate esters has been developed. This efficient reaction features high selectivity and good functional-group tolerance. Notably, given the general nature of the silyl-tethered directing group, this method delivers products bearing two independently modifiable sites. NMR studies reveal the presence of hydrogen bonding between HFIP and a pyrimidine nitrogen atom of the directing group, and it is thought to be crucial for the success of this alkoxycarbonylation reaction.

  17. Plasmid pCBI carries genes for anaerobic benzoate catabolism in Alcaligenes xylosoxidans subsp. denitrificans PN-1.

    PubMed Central

    Blake, C K; Hegeman, G D

    1987-01-01

    Pseudomonas sp. strain PN-1 is reclassified as Alcaligenes xylosoxidans subsp. denitrificans PN-1. Strain PN-1 is a gram-negative, rod-shaped organism, is motile by means of lateral flagella, is oxidase positive, and does not ferment sugars. Plasmid pCBI, carrying genes for the anaerobic degradation of benzoate in strain PN-1, is 17.4 kilobase pairs in length and is transmissible to a number of denitrifying Pseudomonas aeruginosa and Pseudomonas stutzeri strains. A restriction endonuclease map was constructed. PMID:2822651

  18. Two new benzoate derivatives and one new phenylacetate derivative from a marine-derived fungus Engyodontium album.

    PubMed

    Wang, Weiyi; Chen, Ruixuan; Luo, Zhuhua; Wang, Wei; Chen, Jianming

    2017-04-01

    Two new benzoate derivatives, ethyl 3,5-dimethoxy-2-propionylbenzoate (1) and ethyl 3,5-dihydroxy-2-propionylbenzoate (2), and one new phenylacetate derivative, ethyl 3,5-dimethoxy-2-propionylphenylacetate (3), together with 9 known compounds, were isolated from the fermentation of Engyodontium album derived from deep sea sediment. Their structures were elucidated by spectroscopic techniques, such as NMR, IR and HRESIMS. Compound 3 exhibited inhibitory activities against methicillin-resistant Staphylococcus aureus ATCC 43300 (MRSA) and Vibrio vulnificus, with MIC values of 7.8 and 15.6 μg/mL, respectively.

  19. PLASMID-ENCODED PHTHALATE CATABOLIC PATHWAY IN ARTHROBACTER KEYSERI 12B: BIOTRANSFORMATIONS OF 2-SUBSTITUTED BENZOATES AND THEIR USE IN CLONING AND CHARACTERIZATION OF PHTHALATE CATABOLISM GENES AND GENE PRODUCTS

    EPA Science Inventory

    Several 2-substituted benzoates (including 2-trifluoromethyl-, 2-chloro-, 2-bromo-, 2-iodo-, 2-nitro-, 2-methoxy-, and 2-acetyl-benzoates) were converted by phthalate-grown Arthrobacter keyseri 12B to the corresponding 2-substituted 3,4-dihydroxybenzoates (protocatechuates)...

  20. Purification and characterization of benzoate-coenzyme A ligase and 2-aminobenzoate-coenzyme A ligases from a denitrifying Pseudomonas sp.

    PubMed Central

    Altenschmidt, U; Oswald, B; Fuchs, G

    1991-01-01

    The enzymes catalyzing the formation of coenzyme A (CoA) thioesters of benzoate and 2-aminobenzoate were studied in a denitrifying Pseudomonas sp. anaerobically grown with these aromatic acids and nitrate as sole carbon and energy sources. Three different rather specific aromatic acyl-CoA ligases, E1, E2, and E3, were found which catalyze the formation of CoA thioesters of benzoate, fluorobenzoates, and 2-aminobenzoate. ATP is cleaved into AMP and pyrophosphate. The enzymes were purified, their N-terminal amino acid sequences were determined, and their catalytic and molecular properties were studied. Cells anaerobically grown on benzoate and nitrate contain one CoA ligase (AMP forming) for benzoic acid (E1). It is a homodimer of Mr 120,000 which prefers benzoate as a substrate but shows some activity also with 2-aminobenzoate and fluorobenzoates, although with lower Km. Cells anaerobically grown on 2-aminobenzoate and nitrate contain three different CoA ligases for aromatic acids. The first one is identical with benzoate-CoA ligase (E1). The second enzyme is a 2-aminobenzoate-CoA ligase (E2). It is a monomer of Mr 60,000 which prefers 2-aminobenzoate but also activates benzoate, fluorobenzoates and, less effectively, 2-methylbenzoate, with lower affinities to the latter substrates. The enzymes E1 and E2 have similar activity levels; a third minor CoA ligase activity is due to a different 2-aminobenzoate-CoA ligase. The enzyme (E3) is a monomer of Mr, 65,000 which 2-aminobenzoate pathway (U. Altenschmidt, C. Eckerskorn, and G. Fuchs, Eur. J. Biochem. 194:647-653, 1990); apparently, it is not completely repressed under anaerobic conditions and therefore also is induced to a small extent by 2-aminobenzoate under anaerobic growth conditions. Images PMID:1885526

  1. The effects of calcium benzoate in diets with or without organic acids on dietary buffering capacity, apparent digestibility, retention of nutrients, and manure characteristics in swine.

    PubMed

    Mroz, Z; Jongbloed, A W; Partanen, K H; Vreman, K; Kemme, P A; Kogut, J

    2000-10-01

    Eight barrows (Yorkshire x [Finnish Landrace x Dutch Landrace]), initially 30 kg BW, were fitted with ileal cannulas to evaluate the effects of supplementing Ca benzoate (2.4%) and organic acids (OA) in the amount of 300 mEq acid/kg feed on dietary buffering capacity (BC), apparent digestibility and retention of nutrients, and manure characteristics. Swine were allotted in a 2 x 4 factorial arrangement of treatments according to a cyclic (8 x 5) changeover design. Two tapioca-corn-soybean meal-based diets were formulated without and with acidogenic Ca benzoate. Each diet was fed in combination with OA (none, formic, fumaric, or n-butyric acid). Daily rations were equal to 2.8 x maintenance requirement (418 kJ ME/BW(.75)) and were given in two portions. Chromic oxide (.25 g/kg) was used as a marker. On average, Ca benzoate lowered BC by 54 mEq/kg feed. This salt enhanced (P < .05) the ileal digestibility (ID) of DM, OM, arginine, isoleucine, leucine, phenylalanine, alanine, aspartic acid, and tyrosine (by up to 2.4 percentage units). Also, the total tract digestibility (TD) of DM, ash, Ca and GE, and Ca retention (percentage of intake) was greater (P < .05) in swine fed Ca benzoate, whereas N retention remained unaffected. Addition of all OA (formic and n-butyric acid, in particular) exerted a positive effect (P < .05) on the ID of amino acids (except for arginine, methionine, and cysteine). A similar effect (P < .05) was found for the TD of DM, OM, CP, Ca and total P and for the retention of N and Ca. In swine fed Ca benzoate, urinary pH decreased by 1.6 units (P < .001). In conclusion, dietary OA have a beneficial effect on the apparent ileal/total tract nutrient digestibilities, and Ca benzoate increased urine acidity, which could be effective against a rapid ammonia emission from manure of swine.

  2. Hydrogen-bonded supra­molecular motifs in pyrimethaminium 4-methyl­benzoate, pyrimethaminium 3-hydroxy­picolinate and pyri­meth­aminium 2,4-di­chloro­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Muthiah, Packianathan Thomas

    2010-01-01

    In 2,4-diamino-5-(4-chloro­phenyl)-6-ethyl­pyrimidin-1-ium (pyri­methaminium, PMNH) 4-methyl­benzoate, C12H14ClN4 +·C8H7O2 −, (I), pyrimethaminium 3-hydroxy­picolinate, C12H14ClN4 +·C6H4NO3 −, (II), and pyrimethaminium 2,4-dichloro­benzoate, C12H14ClN4 +·C7H3Cl2O2 −, (III), the PMNH cations inter­act with the carboxyl­ate groups of the corresponding anion via nearly parallel N—H⋯O hydrogen bonds, forming R 2 2(8) ring motifs. A description of the observed arrays of quadruple hydrogen bonds in (I) and (II) in terms of hydrogen donors and acceptors (the DA model), their graph-set motifs and the resulting supra­molecular ladder is given. In (III), supra­molecular chains along the b axis and helical chains along the a axis are formed via N—H⋯O hydrogen bonds involving the 2-amino and 4-amino groups of the PMNH cation, respectively. Weak Cl⋯Cl inter­actions are also found in (III). PMID:20203404

  3. Synergistic Processing of Biphenyl and Benzoate: Carbon Flow Through the Bacterial Community in Polychlorinated-Biphenyl-Contaminated Soil.

    PubMed

    Leewis, Mary-Cathrine; Uhlik, Ondrej; Leigh, Mary Beth

    2016-02-26

    Aerobic mineralization of PCBs, which are toxic and persistent organic pollutants, involves the upper (biphenyl, BP) and lower (benzoate, BZ) degradation pathways. The activity of different members of the soil microbial community in performing one or both pathways, and their synergistic interactions during PCB biodegradation, are not well understood. This study investigates BP and BZ biodegradation and subsequent carbon flow through the microbial community in PCB-contaminated soil. DNA stable isotope probing (SIP) was used to identify the bacterial guilds involved in utilizing (13)C-biphenyl (unchlorinated analogue of PCBs) and/or (13)C-benzoate (product/intermediate of BP degradation and analogue of chlorobenzoates). By performing SIP with two substrates in parallel, we reveal microbes performing the upper (BP) and/or lower (BZ) degradation pathways, and heterotrophic bacteria involved indirectly in processing carbon derived from these substrates (i.e. through crossfeeding). Substrate mineralization rates and shifts in relative abundance of labeled taxa suggest that BP and BZ biotransformations were performed by microorganisms with different growth strategies: BZ-associated bacteria were fast growing, potentially copiotrophic organisms, while microbes that transform BP were oligotrophic, slower growing, organisms. Our findings provide novel insight into the functional interactions of soil bacteria active in processing biphenyl and related aromatic compounds in soil, revealing how carbon flows through a bacterial community.

  4. Elucidation of the thermophilic phenol biodegradation pathway via benzoate during the anaerobic digestion of municipal solid waste.

    PubMed

    Hoyos-Hernandez, Carolina; Hoffmann, Marieke; Guenne, Angeline; Mazeas, Laurent

    2014-02-01

    Anaerobic digestion makes it possible to valorize municipal solid waste (MSW) into biogas and digestate which are, respectively, a renewable energy source and an organic amendment for soil. Phenols are persistent pollutants present in MSW that can inhibit the anaerobic digestion process and have a toxic effect on microbiota if they are applied to soil together with digestate. It is then important to define the operational conditions of anaerobic digestion which allow the complete degradation of phenol. In this context, the fate of phenol during the anaerobic digestion of MSW at 55°C was followed using an isotopic tracing approach ((13)C6-phenol) in experimental microcosms with inoculum from an industrial thermophilic anaerobic digester. With this approach, it was possible to demonstrate the complete phenol biodegradation into methane and carbon dioxide via benzoate. Benzoate is known to be a phenol metabolite under mesophilic conditions, but in this study it was found for the first time to be a phenol degradation product at thermophilic temperature.

  5. Short communication: Use of a mixture of sodium nitrite, sodium benzoate, and potassium sorbate in aerobically challenged silages.

    PubMed

    Knicky, Martin; Spörndly, Rolf

    2015-08-01

    Aerobic instability is still a common problem with many types of silages, particularly well-fermented silages. This study evaluated the effect of adding an additive mixture based on sodium nitrite, sodium benzoate, and potassium sorbate to a variety of crop materials on fermentation quality and aerobic stability of silages. Ensiling conditions were challenged by using a low packing density (104±4.3kg of dry matter/m(3)) of forage and allowing air ingression into silos (at 14 and 7 d before the end of the storage, for 8 h per event). Additive-treated silages were found to have significantly lower pH and reduced formation of ammonia-N, 2.3-butanediol, and ethanol compared with untreated control silages. Yeast growth was significantly reduced by additive treatment in comparison with untreated control silage. Consequently, additive-treated silages were considerably more aerobically stable (6.7 d) than untreated control silages (0.5 d). Overall, adding 5mL/kg of fresh crop of the additive based on sodium nitrite, sodium benzoate, and potassium sorbate reduced undesirable microorganisms in silages and thereby provided suitable ensiling conditions and prolonged aerobic stability, even under air-challenged laboratory ensiling conditions.

  6. Synergistic Processing of Biphenyl and Benzoate: Carbon Flow Through the Bacterial Community in Polychlorinated-Biphenyl-Contaminated Soil

    NASA Astrophysics Data System (ADS)

    Leewis, Mary-Cathrine; Uhlik, Ondrej; Leigh, Mary Beth

    2016-02-01

    Aerobic mineralization of PCBs, which are toxic and persistent organic pollutants, involves the upper (biphenyl, BP) and lower (benzoate, BZ) degradation pathways. The activity of different members of the soil microbial community in performing one or both pathways, and their synergistic interactions during PCB biodegradation, are not well understood. This study investigates BP and BZ biodegradation and subsequent carbon flow through the microbial community in PCB-contaminated soil. DNA stable isotope probing (SIP) was used to identify the bacterial guilds involved in utilizing 13C-biphenyl (unchlorinated analogue of PCBs) and/or 13C-benzoate (product/intermediate of BP degradation and analogue of chlorobenzoates). By performing SIP with two substrates in parallel, we reveal microbes performing the upper (BP) and/or lower (BZ) degradation pathways, and heterotrophic bacteria involved indirectly in processing carbon derived from these substrates (i.e. through crossfeeding). Substrate mineralization rates and shifts in relative abundance of labeled taxa suggest that BP and BZ biotransformations were performed by microorganisms with different growth strategies: BZ-associated bacteria were fast growing, potentially copiotrophic organisms, while microbes that transform BP were oligotrophic, slower growing, organisms. Our findings provide novel insight into the functional interactions of soil bacteria active in processing biphenyl and related aromatic compounds in soil, revealing how carbon flows through a bacterial community.

  7. 2-Amino-3-(hy­droxy­meth­yl)pyridinium 2-benzoyl­benzoate monohydrate

    PubMed Central

    Odabaşoğlu, Hakkı Yasin; Büyükgüngör, Orhan; Avinç, Osman Ozan; Odabaşoğlu, Mustafa

    2012-01-01

    In the title hydrated salt, C6H9N2O+·C14H9O3 −·H2O, the dihedral angle between the benzene rings of the 2-benzoyl­benzoate anion is 82.04 (14)°, while the angles between the aromatic ring of the pyridinium cation and each of the benzene rings of the anion are 4.42 (14) and 82.04 (14)°. In the crystal, mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, generating a three-dimensional network with R 2 2(8), R 6 6(16) and R 4 4(6) motifs. The crystal packing is further stabilized by two π–π inter­actions, one between pyridinium rings, and another between the benzene benzoate and pyridinium rings of neighbouring mol­ecules, with centroid-to-centroid distances of 3.559 (2) and 3.606 (2) Å, respectively. PMID:22412594

  8. Changes induced by UV radiation in the presence of sodium benzoate in films formulated with polyvinyl alcohol and carboxymethyl cellulose.

    PubMed

    Villarruel, S; Giannuzzi, L; Rivero, S; Pinotti, A

    2015-11-01

    This work was focused on: i) developing single and blend films based on carboxymethyl cellulose (CMC) and polyvinyl alcohol (PVOH) studying their properties, ii) analyzing the interactions between CMC and PVOH and their modifications UV-induced in the presence of sodium benzoate (SB), and iii) evaluating the antimicrobial capacity of blend films containing SB with and without UV treatment. Once the blend films with SB were exposed to UV radiation, they exhibited lower moisture content as well as a greater elongation at break and rougher surfaces compared to those without treatment. Considering oxygen barrier properties, the low values obtained would allow their application as packaging with selective oxygen permeability. Moreover, the characteristics of the amorphous phase of the matrix prevailed with a rearrangement of the structure of the polymer chain, causing a decrease of the crystallinity degree. These results were supported by X-rays and DSC analysis. FT-IR spectra reflected some degree of polymer-polymer interaction at a molecular level in the amorphous regions. The incorporation of sodium benzoate combined with UV treatment in blend films was positive from the microbial point of view because of the growth inhibition of a wide spectrum of microorganisms. From a physicochemical perspective, the UV treatment of films also changed their morphology rendering them more insoluble in water, turning the functionalized blend films into a potential material to be applied as food packaging.

  9. Synergistic Processing of Biphenyl and Benzoate: Carbon Flow Through the Bacterial Community in Polychlorinated-Biphenyl-Contaminated Soil

    PubMed Central

    Leewis, Mary-Cathrine; Uhlik, Ondrej; Leigh, Mary Beth

    2016-01-01

    Aerobic mineralization of PCBs, which are toxic and persistent organic pollutants, involves the upper (biphenyl, BP) and lower (benzoate, BZ) degradation pathways. The activity of different members of the soil microbial community in performing one or both pathways, and their synergistic interactions during PCB biodegradation, are not well understood. This study investigates BP and BZ biodegradation and subsequent carbon flow through the microbial community in PCB-contaminated soil. DNA stable isotope probing (SIP) was used to identify the bacterial guilds involved in utilizing 13C-biphenyl (unchlorinated analogue of PCBs) and/or 13C-benzoate (product/intermediate of BP degradation and analogue of chlorobenzoates). By performing SIP with two substrates in parallel, we reveal microbes performing the upper (BP) and/or lower (BZ) degradation pathways, and heterotrophic bacteria involved indirectly in processing carbon derived from these substrates (i.e. through crossfeeding). Substrate mineralization rates and shifts in relative abundance of labeled taxa suggest that BP and BZ biotransformations were performed by microorganisms with different growth strategies: BZ-associated bacteria were fast growing, potentially copiotrophic organisms, while microbes that transform BP were oligotrophic, slower growing, organisms. Our findings provide novel insight into the functional interactions of soil bacteria active in processing biphenyl and related aromatic compounds in soil, revealing how carbon flows through a bacterial community. PMID:26915282

  10. NEONATAL LOW- AND HIGH-DOSE EXPOSURE TO ESTRADIOL BENZOATE IN THE MALE RAT: II. EFFECTS ON THE MALE PUBERTY AND THE REPRODUCTIVE TRACT

    EPA Science Inventory

    NEONATAL LOW- AND HIGH-DOSE EXPOSURE TO ESTRADIOL BENZOATE IN THE MALE RAT: II. EFFECTS ON MALE PUBERTY AND THE REPRODUCTIVE TRACT. Oliver Putz, Christian B. Schwartz, Gerald A. LeBlanc, Ralph L. Cooper, Gail S. Prins

    ABSTRACT
    Environmental contaminants with estrogen...

  11. Using NMR Spectroscopy to Probe the Chemo- and Diastereoselectivity in the NaBH[subscript 4] Reduction of Benzoin Acetate and Benzoin Benzoate

    ERIC Educational Resources Information Center

    Saba, Shahrokh; Cagino, Kristen; Bennett, Caitlin

    2015-01-01

    A pedagogically useful discovery-based undergraduate organic chemistry lab experiment probing the chemo- and diastereoselectivity in the NaBH[subscript 4] reduction of two chiral ketoesters (benzoin acetate and benzoin benzoate) has been developed. This experiment complements a previously described and highly popular discovery-based experiment…

  12. Methyl 2-((succinimidooxy)carbonyl)benzoate (MSB): a new, efficient reagent for N-phthaloylation of amino acid and peptide derivatives.

    PubMed

    Casimir, J Richard; Guichard, Gilles; Briand, Jean-Paul

    2002-05-31

    A new, efficient, and readily available reagent, methyl 2-((succinimidooxy)carbonyl)benzoate (MSB), for N-phthaloylation of amino acids and amino acid derivatives is described. The phthaloylation procedure is simple and racemization-free and gives excellent results with alpha-amino acids, alpha-amino alcohols, dipeptides, alpha-amino carboxamides, and alpha-amino esters.

  13. The ZbYME2 gene from the food spoilage yeast Zygosaccharomyces bailii confers not only YME2 functions in Saccharomyces cerevisiae, but also the capacity for catabolism of sorbate and benzoate, two major weak organic acid preservatives.

    PubMed

    Mollapour, M; Piper, P W

    2001-11-01

    A factor influencing resistances of food spoilage microbes to sorbate and benzoate is whether these organisms are able to catalyse the degradation of these preservative compounds. Several fungi metabolize benzoic acid by the beta-ketoadipate pathway, involving the hydroxylation of benzoate to 4-hydroxybenzoate. Saccharomyces cerevisiae is unable to use benzoate as a sole carbon source, apparently through the lack of benzoate-4-hydroxylase activity. However a single gene from the food spoilage yeast Zygosaccharomyces bailii, heterologously expressed in S. cerevisiae cells, can enable growth of the latter on benzoate, sorbate and phenylalanine. Although this ZbYME2 gene is essential for benzoate utilization by Z. bailii, its ZbYme2p product has little homology to other fungal benzoate-4-hydroxylases studied to date, all of which appear to be microsomal cytochrome P450s. Instead, ZbYme2p has strong similarity to the matrix domain of the S. cerevisiae mitochondrial protein Yme2p/Rna12p/Prp12p and, when expressed as a functional fusion to green fluorescent protein in S. cerevisiae growing on benzoate, is largely localized to mitochondria. The phenotypes associated with loss of the native Yme2p from S. cerevisiae, mostly apparent in yme1,yme2 cells, may relate to increased detrimental effects of endogenous oxidative stress. Heterologous expression of ZbYME2 complements these phenotypes, yet it also confers a potential for weak acid preservative catabolism that the native S. cerevisiae Yme2p is unable to provide. Benzoate utilization by S. cerevisiae expressing ZbYME2 requires a functional mitochondrial respiratory chain, but not the native Yme1p and Yme2p of the mitochondrion.

  14. Recombination of the bph (Biphenyl) Catabolic Genes from Plasmid pWW100 and Their Deletion during Growth on Benzoate

    PubMed Central

    Lloyd-Jones, Gareth; de Jong, Caroline; Ogden, Richard C.; Duetz, Wouter A.; Williams, Peter A.

    1994-01-01

    Pseudomonas sp. strain CB406 was isolated from polychlorinated biphenyl-contaminated soil and harbors a nontransmissible plasmid, pWW100, of approximately 200 kb which carries the genes required for biphenyl and 4-chlorobiphenyl catabolism. The catabolic phenotype was mobilized following the construction in vivo of a cointegrate plasmid containing functional upper and lower biphenyl operons inserted into the broad-host-range R plasmid RP4. The Bph+ phenotype carried by pWW100 was stable in nonselective media but was unstable during growth on benzoate, where the sequential selection of two species of bph deletion derivatives occurs at high frequency. This mirrors observations made with TOL plasmids (encoding toluene and xylene catabolism) grown under similar conditions. Subcloning of dioxygenase genes involved in biphenyl catabolism confirmed the localization of the bph genes on the wild-type plasmid and the RP4 cointegrate plasmid. Images PMID:16349195

  15. Degradation of organic ultraviolet filter diethylamino hydroxybenzoyl hexyl benzoate in aqueous solution by UV/H2O2.

    PubMed

    Gong, Ping; Yuan, Haixia; Zhai, Pingping; Dong, Wenbo; Li, Hongjing

    2015-07-01

    Steady-state and transient-state photolysis experiments were conducted to investigate the degradation of organic ultraviolet filter diethylamino hydroxybenzoyl hexyl benzoate (DHHB) in the aqueous solution by UV/H2O2. Results showed that the obvious degradation of DHHB was not observed under UV irradiation (λ = 254 nm), and the DHHB degradation was conducted due to the oxidation by hydroxyl radical (HO·). While the H2O2 concentration was between 0.05 and 0.10 mol L(-1), the highest DHHB degradation efficiency was obtained. The lower solution pH favored the transformation of DHHB, and the coexisting Cl(-) and NO3(-) ions slightly enhanced the conversion. The degradation of DHHB by HO· followed a pseudo-first-order kinetic model with different initial DHHB concentrations. By intermediate products during DHHB oxidation and laser flash photolysis spectra analysis, a primary degradation pathway was proposed.

  16. Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors.

    PubMed

    Saeed, Aamer; Khan, Muhammad Siraj; Rafique, Hummera; Shahid, Mohammad; Iqbal, Jamshed

    2014-02-01

    Thioureas are exceptionally versatile building blocks towards the synthesis of wide variety of heterocyclic systems, which also possess extensive range of pharmacological activities. The substituted benzoic acids were converted into corresponding acid chlorides, these acid chlorides were then treated with potassium thiocyanate in acetone and then the reaction mixture was refluxed for 1-2h afford ethyl 4-(3-benzoylthioureido)benzoates thioureas in good yields. All the newly synthesized compounds were evaluated for their urease inhibitory activities and were found to be potent inhibitors of urease enzyme. Compounds 1f and 1g were identified as the most potent urease inhibitors (IC50 0.21 and 0.13 μM, respectively), and was 100-fold more potent than the standard inhibitors. Further molecular docking studies were carried out using the crystal structure of urease to find out the binding mode of the inhibitors with the enzyme.

  17. Rate-determining Attack on Substrate Precedes Rieske Cluster Oxidation during cis-Dihydroxylation by Benzoate Dioxygenase

    PubMed Central

    Rivard, Brent S.; Rogers, Melanie S.; Marell, Daniel J.; Neibergall, Matthew B.; Chakrabarty, Sarmistha; Cramer, Christopher J.; Lipscomb, John D.

    2015-01-01

    Rieske dearomatizing dioxygenases utilize a Rieske iron-sulfur cluster and a mononuclear Fe(II) located 15 Å across a subunit boundary to catalyze O2-dependent formation of cis-dihydrodiol products from aromatic substrates. During catalysis, O2 binds to the Fe(II) while the substrate bind nearby. Single turnover reactions have shown that one electron from each metal center is required for catalysis. This finding suggested that the reactive intermediate is Fe(III)-(H)peroxo or HO-Fe(V)=O formed by O-O bond scission. Surprisingly, several kinetic phases were observed during the single turnover Rieske cluster oxidation. Here, the Rieske cluster oxidation and product formation steps of a single turnover of benzoate 1,2-dioxygenase are investigated using benzoate and three fluorinated analogs. It is shown that the rate constant for product formation correlates with the reciprocal relaxation time of only the fastest kinetic phase (RRT-1) for each substrate, suggesting that the slower phases are not mechanistically relevant. RRT-1 is strongly dependent on substrate type, suggesting a role for substrate in electron transfer from the Rieske cluster to the mononuclear iron site. This insight, together with the substrate and O2 concentration dependencies of RRT-1, indicates that a reactive species is formed after substrate and O2 binding, but before electron transfer from the Rieske cluster. Computational studies show that RRT-1 is correlated with the electron density at the substrate carbon closest to the Fe(II), consistent with initial electrophilic attack by an Fe(III)-superoxo intermediate. The resulting Fe(III)-peroxo-aryl radical species would then readily accept an electron from the Rieske cluster to complete the cis-dihydroxylation reaction. PMID:26154836

  18. Comparison of safety, efficacy, and cost effectiveness of benzyl benzoate, permethrin, and ivermectin in patients of scabies

    PubMed Central

    Bachewar, Narendra P.; Thawani, Vijay R.; Mali, Smita N.; Gharpure, Kunda J.; Shingade, Vaishali P.; Dakhale, Ganesh N.

    2009-01-01

    Objective: To compare three treatment modalities in scabies for safety, efficacy, and economy in a local population of Nagpur. Materials and Methods: This was a prospective, randomized, comparative clinical trial conducted in 103 participants, randomly allocated to three groups. First group received benzyl benzoate (BB) 25% lotion, second group received permethrin 5% cream, whereas third group received tablet ivermectin 200 μg/kg as a single dose. The participants were recalled after one week for follow-up evaluation. If there were no signs of cure, the same intervention was repeated. The participants were followed up for two weeks for cure rate, adverse drug reaction (ADR) monitoring, and postintervention observation. The follow-up was stopped after two weeks. Statistics: Fischer's exact test using Graph pad Instat v 3.05. Results: Ivermectin showed 100% cure rate after two weeks of treatment. Permethrin decreased pruritus by 76% at the end of one week and had significantly better cure rate than ivermectin. At the end of two weeks treatment, this finding was reversed, that is, cure rate in ivermectin group was 100%. For cost-effectiveness analysis, treatment regimens were formulated hypothetically for comparison from Markov population tree for decision analysis. It was found that BB and ivermectin each consecutively for two weeks were most cost effective regimens giving complete cure in four weeks, while ivermectin was the fastest regimen giving the same results in two weeks. Conclusion: Benzyl benzoate as first line intervention and ivermectin in the remaining gave best cost-effective results in the study patients of scabies. PMID:20177574

  19. 78 FR 49932 - Emamectin; Pesticide Tolerance

    Federal Register 2010, 2011, 2012, 2013, 2014

    2013-08-16

    .... There is evidence that avermectin B 1a binds to GABA A receptors and activates Cl\\-\\ flux into neurons... alterations in cellular excitability of mammalian neurons and neural networks (i.e., changes in...

  20. I. Mechanism of the formation of methylenecyclobutenone by the flash vacuum pyrolysis of ufrfuryl benzoate. II. Chemistry of 2-methylenebenzocyclobutenone and indenone prepared by the flash vacuum pyrolysis of 3-benzoyloxymethylbenzofuran

    SciTech Connect

    Amah, A.N.

    1984-06-01

    The flash vacuum pyrolysis chemistry of a series of deuterated furfuryl benzoates, furfuryl-..cap alpha.., ..cap alpha..-d/sub 2/ benzoate, furfuryl-5-d/sub 1/ benzoate, and furfuryl-3-d/sub 1/ benzoate have been investigated. Mechanisms were proposed for the formation of the pyrolysis products, methylenecyclobutenone, vinylacetylene, and the dimer of cyclopentadienone, from each of the compounds studies which involved initial alpha elimination of benzoic acid, a single (3,3) migration followed by alpha elimination of benzoic acid, and two (3,3) migrtions followed by alpha elimination of benzoic acid. Synthesis of 2-methylenebenzocyclobutenone and indenone by the flash vacuum pyrolysis of 3-benzoyloxymethylbenzofuran is described. A procedure was developed for the decarboxylation of 2,3-benzofurandicarboxylic acid in > 80% yield to the key intermediate 3-benzofurancarboxylic acid. Mechanisms were proposed for the formation of the pyrolysis products 2-methylenebenzocyclobutenone, indenone, phenylacetylene, and o-ethynylbenzaldehyde.

  1. A Validated Stability-Indicating RP-UPLC Method for Simultaneous Determination of Desloratadine and Sodium Benzoate in Oral Liquid Pharmaceutical Formulations

    PubMed Central

    Kumar, Navneet; Sangeetha, Dhanaraj; Reddy, Pingili Sunil; Prakash, Lakkireddy

    2012-01-01

    A novel, sensitive and selective stability-indicating gradient reverse phase ultra performance liquid chromatographic method was developed and validated for the quantitative determination of desloratadine and sodium benzoate in pharmaceutical oral liquid formulation. The chromatographic separation was achieved on Acquity BEH C8 (100 mm × 2.1 mm) 1.7 μm column by using mobile phase containing a gradient mixture of solvent A (0.05 M KH2PO4 and 0.07 M triethylamine, pH 3.0) and B (50:25:25 v/v/v mixture of acetonitrile, methanol and water) at flow rate of 0.4 mL/min. Column temperature was maintained at 40°C and detection was carried out at a wavelength of 272 nm. The described method shows excellent linearity over a range of 0.254 μg/mL to 76.194 μg/mL for desloratadine and 1.006 μg/mL to 301.67 μg/mL for sodium benzoate. The correlation coefficient for desloratadine and sodium benzoate was more than 0.999. To establish stability-indicating capability of the method, drug product was subjected to the stress conditions of acid, base, oxidative, hydrolytic, thermal and photolytic degradation. The degradation products were well resolved from desloratadine and sodium benzoate. The developed method was validated as per international ICH guidelines with respect to specificity, linearity, LOD, LOQ, accuracy, precision and robustness. PMID:22396911

  2. Reversible Nε-Lysine Acetylation Regulates the Activity of Acyl-CoA Synthetases Involved in Anaerobic Benzoate Catabolism in Rhodopseudomonas palustris

    PubMed Central

    Crosby, Heidi A.; Heiniger, Erin K.; Harwood, Caroline S.; Escalante-Semerena, Jorge C.

    2010-01-01

    Rhodopseudomonas palustris grows photoheterotrophically on aromatic compounds available in aquatic environments rich in plant-derived lignin. Benzoate degradation is regulated at the transcriptional level in R. palustris in response to anoxia and the presence of benzoate and/or benzoyl-CoA (Bz-CoA). Here, we report evidence that anaerobic benzoate catabolism in this bacterium is also regulated at the posttranslational level. In this pathway, benzoate is activated to Bz-CoA by the AMP-forming Bz-CoA synthetase (BadA) enzyme. Mass spectrometry and mutational analysis data indicate that residue Lys512 is critical to BadA activity. Acetylation of Lys512 inactivated BadA; deacetylation reactivated BadA. Likewise, 4-hydroxybenzoyl-CoA (HbaA) and cyclohexanecarboxyl-CoA (AliA) synthetases were also reversibly acetylated. We identified one acetyltransferase that modified BadA, Hba, and AliA in vitro. The acetyltransferase enzyme is homologous to the protein acetyltransferase (Pat) enzyme of Salmonella enterica sv Typhimurium LT2, thus we refer to it as RpPat. RpPat also modified acetyl-CoA (Ac-CoA) synthetase (Acs) from R. palustris. In vivo data indicate that at least two deacetylases reactivate BadAAc. One is SrtN (encoded by srtN, formerly rpa2524), a sirtuin-type NAD+-dependent deacetylase (O-acetyl-ADP-ribose-forming); the other deacetylase is LdaA (encoded by ldaA, for lysine deacetylase A; formerly rpa0954), an acetate-forming protein deacetylase. LdaA reactivated HbaAc and AliAAc in vitro. PMID:20345662

  3. Surfactant gradient methods using mixed systems of cethyltrimethylammonium chloride and nonionic surfactants possessing polyoxyethylene chains for electrokinetic separation of benzoate anions as model analytes.

    PubMed

    Esaka, Yukihiro; Sawamura, Mika; Murakami, Hiroya; Uno, Bunji

    2006-12-01

    Surfactant gradient methods for electrokinetic separation of 10 benzoates as model organic anions were investigated using mixed micellar solutions of cetyltrimethylammonium chloride (CTAC) and nonionic surfactants possessing polyoxyethylene chains, polyoxyethylene sorbitan monolaurate (Tween 20) or polyoxyethylene lauryl ether (Brij 35). Electroosmotic flow (EOF) was eliminated virtually by a coating of the inner wall of the capillaries, and then the benzoates were detected fundamentally in the order of their hydrophobicity. In a pure CTAC system, the synergistic influences of attractive electrostatic and hydrophobic interactions gave rise to quite large retention factors of many of the benzoate anions, resulting in their coelution. Addition of an adequate amount of Tween 20 to the pure CTAC system decreased the electrostatic interaction significantly to give remarkably improved separation of the analytes, but long analysis time was required. A surfactant gradient method would be useful to decrease analysis time and to improve separation simultaneously. Under slight EOF, the micelles in the inlet reservoir can pass through and, thus, interact with all of the analytes before they were detected. In the present system, surfactant gradient separations could be performed simply by changing compositions of the surfactant solutions in the inlet reservoir during a single run. Additionally, we carried out continuous gradient separation using a simple device. Brij 35 gave an effect parallel to that by Tween 20 in migration behavior of the analytes. A practically negligible change in the level of the baseline was observed in a stepwise gradient elution with the CTAC/Brij 35 system because of the small absorbance at the detection wavelength, while that with the CTAC/Tween 20 was considerable. All the benzoates were separated completely within reasonable analysis times using both stepwise and continuous gradient programs for the concentrations of Tween 20 or Brij 35 in the

  4. A Validated Stability-Indicating RP-UPLC Method for Simultaneous Determination of Desloratadine and Sodium Benzoate in Oral Liquid Pharmaceutical Formulations.

    PubMed

    Kumar, Navneet; Sangeetha, Dhanaraj; Reddy, Pingili Sunil; Prakash, Lakkireddy

    2012-01-01

    A novel, sensitive and selective stability-indicating gradient reverse phase ultra performance liquid chromatographic method was developed and validated for the quantitative determination of desloratadine and sodium benzoate in pharmaceutical oral liquid formulation. The chromatographic separation was achieved on Acquity BEH C8 (100 mm × 2.1 mm) 1.7 μm column by using mobile phase containing a gradient mixture of solvent A (0.05 M KH(2)PO(4) and 0.07 M triethylamine, pH 3.0) and B (50:25:25 v/v/v mixture of acetonitrile, methanol and water) at flow rate of 0.4 mL/min. Column temperature was maintained at 40°C and detection was carried out at a wavelength of 272 nm. The described method shows excellent linearity over a range of 0.254 μg/mL to 76.194 μg/mL for desloratadine and 1.006 μg/mL to 301.67 μg/mL for sodium benzoate. The correlation coefficient for desloratadine and sodium benzoate was more than 0.999. To establish stability-indicating capability of the method, drug product was subjected to the stress conditions of acid, base, oxidative, hydrolytic, thermal and photolytic degradation. The degradation products were well resolved from desloratadine and sodium benzoate. The developed method was validated as per international ICH guidelines with respect to specificity, linearity, LOD, LOQ, accuracy, precision and robustness.

  5. Administration of estradiol benzoate before insemination could skew secondary sex ratio toward males in Holstein dairy cows.

    PubMed

    Emadi, S R; Rezaei, A; Bolourchi, M; Hovareshti, P; Akbarinejad, V

    2014-07-01

    The present study was conducted to investigate the effect of estradiol benzoate administration before insemination on secondary sex ratio (proportion of male calves at birth) in Holstein dairy cows. Cows (n = 1,647) were randomly assigned to 2 experimental groups by parity over a 1-yr period. Cows in the control group (n = 827; 232 primiparous and 595 multiparous cows) received 2 administrations of PGF2α (500 μg) 14 d apart, started at 30 to 35 d postpartum. Twelve d after the second PGF2α injection, cows received GnRH (100 μg), followed by administration of PGF2α 7 d later. Cows in the treatment group (n = 820; 238 primiparous and 582 multiparous cows) received the same hormonal administrations as the cows in the control group. Additionally, cows in the treatment group received estradiol benzoate (1 mg) 1 d after the third PGF2α injection. Estrus detection by visual observation was started 1 d after the third PGF2α injection and after estradiol administration in the control (for 6 d) and treatment (for 36 h) groups, respectively. Artificial insemination was carried out 12 h after observation of standing estrus. Exposure of cows to heat stress at conception was determined based on temperature-humidity index. Estrus detection rate was lower in primiparous than in multiparous cows (P < 0.05), but conception rate was higher in primiparous vs multiparous cows (P < 0.05). Estradiol administration improved estrus detection rate and fertility (P < 0.05); moreover, it increased secondary sex ratio (adjusted odds ratio: 1.645; P = 0.017). Exposure to heat stress diminished heat detection rate and fertility (P < 0.05), and altered secondary sex ratio toward males (adjusted odds ratio: 2.863; P = 0.012). In conclusion, the present study revealed that estradiol administration before insemination could improve fertility and increase the probability of calves being male in Holstein dairy cows. Moreover, the results showed that cows exposed to heat stress around

  6. Synthesis, structure and temperature-depended 2D IR correlation spectroscopy of an organo-bismuth benzoate with 1,10-phenanthroline

    NASA Astrophysics Data System (ADS)

    Sun, Yan-Qiong; Zhong, Jie-Cen; Liu, Le-Hui; Qiu, Xing-Tai; Chen, Yi-Ping

    2016-11-01

    An organo-bismuth benzoate with phen as auxiliary ligand, [Bi(phen)(C6H5COO)(C6H4COO)] (1) (phen = 1,10-phenanthroline) has been hydrothermally synthesized from bismuth nitrate, 2-mercaptonbenzoic acid with phen as auxiliary ligand and characterized by single-crystal X-ray diffraction, elemental analyses, PXRD, IR spectra, TG analyses, temperature-depended 2D-IR COS (two-dimensional infrared correlation spectroscopy). Interestingly, benzoate anions in 1 came from the desulfuration reaction of 2-mercaptonbenzoic acid under hydrothermal condition. Compound 1 is a discrete organo-bismuth compound with benzoate and phen ligands. The offset face-to-face π-π stacking interactions and C-H⋯O hydrogen bonds link the isolate complex into a 3D supramolecular network. The temperature-depended 2D-IR COS indicates that the stretching vibrations of Cdbnd C/Cdbnd N of aromatic rings and Cdbnd O bonds are sensitive to the temperature change.

  7. Syntrophus aciditrophicus sp. nov., a new anaerobic bacterium that degrades fatty acids and benzoate in syntrophic association with hydrogen-using microorganisms

    NASA Technical Reports Server (NTRS)

    Jackson, B. E.; Bhupathiraju, V. K.; Tanner, R. S.; Woese, C. R.; McInerney, M. J.

    1999-01-01

    Strain SBT is a new, strictly anaerobic, gram-negative, nonmotile, non-sporeforming, rod-shaped bacterium that degrades benzoate and certain fatty acids in syntrophic association with hydrogen/formate-using microorganisms. Strain SBT produced approximately 3 mol of acetate and 0.6 mol of methane per mol of benzoate in coculture with Methanospirillum hungatei strain JF1. Saturated fatty acids, some unsaturated fatty acids, and methyl esters of butyrate and hexanoate also supported growth of strain SBT in coculture with Desulfovibrio strain G11. Strain SBT grew in pure culture with crotonate, producing acetate, butyrate, caproate, and hydrogen. The molar growth yield was 17 +/- 1 g cell dry mass per mol of crotonate. Strain SBT did not grow with fumarate, iron(III), polysulfide, or oxyanions of sulfur or nitrogen as electron acceptors with benzoate as the electron donor. The DNA base composition of strain SBT was 43.1 mol% G+C. Analysis of the 16 S rRNA gene sequence placed strain SBT in the delta-subdivision of the Proteobacteria, with sulfate-reducing bacteria. Strain SBT was most closely related to members of the genus Syntrophus. The clear phenotypic and genotypic differences between strain SBT and the two described species in the genus Syntrophus justify the formation of a new species, Syntrophus aciditrophicus.

  8. An assessment of detection canine alerts using flowers that release methyl benzoate, the cocaine odorant, and an evaluation of their behavior in terms of the VOCs produced.

    PubMed

    Cerreta, Michelle M; Furton, Kenneth G

    2015-06-01

    In recent years, the high frequency of illicit substance abuse reported in the United States has made the development of efficient and rapid detection methods important. Biological detectors, such as canines (Canis familiaris), are valuable tools for rapid, on-site identification of illicit substances. However, research indicates that in many cases canines do not alert to the contraband, but rather to the volatile organic compounds (VOCs) that are released from the contraband, referred to as the "active odor." In 2013, canine accuracy and reliability were challenged in the Supreme Court case, State of Florida v. Jardines. In this case, it was stated that if a canine alerts to the active odor, and not the contraband, the canine's accuracy and selectivity could be questioned, since many of these compounds have been found in common household products. Specifically, methyl benzoate, the active odor of cocaine, has been found to be the most abundant compound produced by snapdragon flowers. Therefore, the purpose of this study is to evaluate the odor profiles of various species of snapdragon flowers to assess how significantly methyl benzoate contributes to the total VOC profile or fragrance that is produced. Particularly, this study examines the VOCs released from newly grown snapdragon flowers and determines its potential at eliciting a false alert from specially trained detection canines. The ability of detection canines to differentiate between cocaine and snapdragon flowers was determined in order to validate the field accuracy and discrimination power of these detectors. An optimized method using headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry (HS-SPME/GC-MS) was used to test the different types and abundances of compounds generated from snapdragon flowers at various stages throughout the plants' life cycle. The results indicate that although methyl benzoate is present in the odor profile of snapdragon flowers, other

  9. Vibrational spectroscopy, intramolecular CH⋯O interaction and conformational analysis of 2,5-dimethyl-benzyl benzoate

    NASA Astrophysics Data System (ADS)

    Viana, Rommel B.; Ribeiro, Gabriela L. O.; Valencia, Leidy J.; Varela, Jaldyr J. G.; Viana, Anderson B.; da Silva, Albérico B. F.; Moreno-Fuquen, Rodolfo

    2016-12-01

    The aim of this study was to report the spectroscopic and electronic properties of 2,5-dimethyl-benzyl benzoate. FT-IR and Raman vibrational spectral analyses were performed, while a computational approach was used to elucidate the vibrational frequency couplings. The electronic properties were predicted using the Density Functional Theory, while the G3MP2 method was employed in the thermochemical calculation. A conformational analysis, frontier orbitals, partial atomic charge distribution and the molecular electrostatic potential were also estimated. Concerning to the dihedral angles in the ester group, a conformational analysis showed a barrier energy of 10 kcal mol-1, while other small barriers (below 0.6 kcal mol-1) were predicted within the potential surface energy investigation. Insights into the relative stability among the different positions of methyl groups in the phenyl ring demonstrated that the energy gaps were lower than 1 kcal mol-1 among the regioisomers. In addition, the Quantum Theory of Atoms in Molecules (QTAIM) was used to understand the intramolecular CH⋯O interaction in the title compound, while various methodologies were applied in the atomic charge distribution to evaluate the susceptibility to the population method.

  10. Crystal structure of 2-(4-chloro­phen­yl)-2-oxoethyl 3-bromo­benzoate

    PubMed Central

    Khan, Imtiaz; Ibrar, Aliya; Hameed, Shahid; White, Jonathan M.; Simpson, Jim

    2014-01-01

    2-(4-Chloro­phen­yl)-2-oxoethyl 3-bromo­benzoate, C15H10BrClO3, was synthesized in a single-step reaction by condensation of 3-bromo­benzoic acid with 2-bromo-1-(4-chloro­phen­yl)ethanone in di­methyl­formamide in the presence of tri­ethyl­amine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methyl­ene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, mol­ecules form five separate sets of inversion dimers. Three of these are generated by two C—H⋯O inter­actions and a C—H⋯Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π–π stacking inter­actions between like aryl rings again form chains of mol­ecules but in this instance along the bc diagonal. These contacts generate infinite layers of mol­ecules parallel to (011) and stack the mol­ecules along the a-axis direction. PMID:25484728

  11. In vitro and in vivo metabolism of ethyl 4-[(2-hydroxy-1-naphthyl)azo]benzoate.

    PubMed

    Bekce, Banu; Sener, Göksel; Oktav, Mehmet; Ulgen, Mert; Rollas, Sevim

    2005-01-01

    Azo compounds are extensively used for colouring food, drink, pharmaceuticals, cosmetics, textiles and printing inks. Publications in the literature have shown that azo dyes can pose threats to public health by metabolic and chemical oxidation and reduction reactions. In the present study, the in vivo and in vitro biotransformation of ethyl 4-[(2-hydroxy-1-naphthyl)azo]benzoate, an azo compound which is structurally similar to 1-phenylazo-2-naphthol was studied to investigate its in vivo and in vitro metabolic products. For the in vitro biotransformation study, rat liver microsomal preparations fortified with NADPH as a co-factor were used. Three unidentified metabolic products were observed. For the in vivo biotransformation study, a concentrated solution of this substrate was given orally to female rats. After the administration of substrate, blood samples of rats are taken at certain intervals. The blood plasma were obtained by centrifuging blood samples. The cold acetonitrile was added to plasma to precipitate plasma proteins and plasma was centrifuged. The supernatant was evaporated at room temperature. The residue was reconstituted with acetonitrile and examined by the HPLC. The unchanged substrate together with the corresponding reduction and acetylation products were detected in plasma. However, no initial hydrolysis occurred in the ester moiety.

  12. Observation of transient alignment-inversion walls in nematics of phenyl benzoates in the presence of a magnetic field.

    PubMed

    Hinov, Hristo P; Vistin', Leonard K; Marinov, Yordan G

    2014-04-17

    Formation of new transient walls by a constant magnetic field at the Fréedericsz critical value has been observed. They are oriented along the initial alignment of the nematic phase of phenyl benzoates and appeared only in relatively thick samples with a thickness between 50 and 100 μm of the cells. The excellent planarity of the liquid crystal orientation is considered to be the most important condition for their presence These magnetic walls are transient as they disappear either after a few seconds for 100 μm thick nematic cells or after parts of a second for thinner (50 μm) nematic cells. Nonregular stable magnetic walls, incorporating disclinations with core, appear immediately after the relaxation of the transient walls, when the planarity of the nematic orientation is not perfect. In thinner nematic cells of 20 μm or less, a Fréedericksz transition has only been observed. The formation of transient magnetic walls can be described by a model taking into account alignment-inversion, twisted along Y regions. The transient walls accompanied by a system of Becke lines relax by going through three-dimensional twist-splay-bend deformations.

  13. Sodium benzoate, a food preservative, affects the functional and activation status of splenocytes at non cytotoxic dose.

    PubMed

    Yadav, Ashish; Kumar, Arvind; Das, Mukul; Tripathi, Anurag

    2016-02-01

    Sodium benzoate (SB) is a widely used food preservative due to its bacteriostatic and fungistatic properties. The acceptable daily intake of SB is 5 mg/kg-bw, however, it has been found to be used in the food commodities at relatively high levels (2119 mg/kg). Earlier studies on SB have shown its immunosuppressive properties, but comprehensive immunotoxicity data is lacking. Our studies have shown that SB was non cytotoxic in splenocytes up to 1000 μg/ml for 72 h, however at 2500 μg/ml it was found to be cytotoxic. Thus, 1000 μg/ml dose of SB was chosen for the subsequent experiments. SB significantly suppresses the proliferation of Con A and LPS stimulated splenocytes at 72 h, while allogenic response of T cells was significantly decreased after 96 h. SB did not affect the relative expression of CD3e or CD4 molecules following 72 h exposure, however, it downregulated the relative expression of CD8 co-receptor. Further, exposure of splenocytes to SB for 72 h led to reduced expression of CD28 and CD95, which play a vital role in T cell activation. SB also suppresses the relative expression of CD19, CD40 and CD95 receptors on B cells after 72 h. In addition to the functional responses, SB lowered the expression of IL4, IL6, IFNγ and IL17 cytokines in Con A stimulated splenocytes; and IL6, IFNγ and TNFα in LPS stimulated splenocytes following 48 h of exposure. Taken together, the present study is suggestive of the immunomodulatory potential of SB.

  14. Up-regulation of neurotrophic factors by cinnamon and its metabolite sodium benzoate: therapeutic implications for neurodegenerative disorders.

    PubMed

    Jana, Arundhati; Modi, Khushbu K; Roy, Avik; Anderson, John A; van Breemen, Richard B; Pahan, Kalipada

    2013-06-01

    This study underlines the importance of cinnamon, a widely-used food spice and flavoring material, and its metabolite sodium benzoate (NaB), a widely-used food preservative and a FDA-approved drug against urea cycle disorders in humans, in increasing the levels of neurotrophic factors [e.g., brain-derived neurotrophic factor (BDNF) and neurotrophin-3 (NT-3)] in the CNS. NaB, but not sodium formate (NaFO), dose-dependently induced the expression of BDNF and NT-3 in primary human neurons and astrocytes. Interestingly, oral administration of ground cinnamon increased the level of NaB in serum and brain and upregulated the levels of these neurotrophic factors in vivo in mouse CNS. Accordingly, oral feeding of NaB, but not NaFO, also increased the level of these neurotrophic factors in vivo in the CNS of mice. NaB induced the activation of protein kinase A (PKA), but not protein kinase C (PKC), and H-89, an inhibitor of PKA, abrogated NaB-induced increase in neurotrophic factors. Furthermore, activation of cAMP response element binding (CREB) protein, but not NF-κB, by NaB, abrogation of NaB-induced expression of neurotrophic factors by siRNA knockdown of CREB and the recruitment of CREB and CREB-binding protein to the BDNF promoter by NaB suggest that NaB exerts its neurotrophic effect through the activation of CREB. Accordingly, cinnamon feeding also increased the activity of PKA and the level of phospho-CREB in vivo in the CNS. These results highlight a novel neutrophic property of cinnamon and its metabolite NaB via PKA - CREB pathway, which may be of benefit for various neurodegenerative disorders.

  15. DNA methylome changes by estradiol benzoate and bisphenol A links early-life environmental exposures to prostate cancer risk

    PubMed Central

    Cheong, Ana; Zhang, Xiang; Cheung, Yuk-Yin; Tang, Wan-yee; Chen, Jing; Ye, Shu-Hua; Medvedovic, Mario; Leung, Yuet-Kin; Prins, Gail S.; Ho, Shuk-Mei

    2016-01-01

    ABSTRACT Developmental exposure to endocrine-disrupting chemicals (EDCs), 17β-estradiol-3-benzoate (EB) and bisphenol A (BPA), increases susceptibility to prostate cancer (PCa) in rodent models. Here, we used the methylated-CpG island recovery assay (MIRA)-assisted genomic tiling and CpG island arrays to identify treatment-associated methylome changes in the postnatal day (PND)90 dorsal prostate tissues of Sprague-Dawley rats neonatally (PND1, 3, and 5) treated with 25 µg/pup or 2,500 µg EB/kg body weight (BW) or 0.1 µg BPA/pup or 10 µg BPA/kg BW. We identified 111 EB-associated and 86 BPA-associated genes, with 20 in common, that have significant differentially methylated regions. Pathway analysis revealed cancer as the top common disease pathway. Bisulfite sequencing validated the differential methylation patterns observed by array analysis in 15 identified candidate genes. The methylation status of 7 (Pitx3, Wnt10b, Paqr4, Sox2, Chst14, Tpd52, Creb3l4) of these 15 genes exhibited an inverse correlation with gene expression in tissue samples. Cell-based assays, using 5-aza-cytidine-treated normal (NbE-1) and cancerous (AIT) rat prostate cells, added evidence of DNA methylation-mediated gene expression of 6 genes (exception: Paqr4). Functional connectivity of these genes was linked to embryonic stem cell pluripotency. Furthermore, clustering analyses using the dataset from The Cancer Genome Atlas revealed that expression of this set of 7 genes was associated with recurrence-free survival of PCa patients. In conclusion, our study reveals that gene-specific promoter methylation changes, resulting from early-life EDC exposure in the rat, may serve as predictive epigenetic biomarkers of PCa recurrence, and raises the possibility that such exposure may impact human disease. PMID:27415467

  16. Comparison of early morphological and molecular changes induced by 17-alpha-methyltestosterone and estradiol benzoate in the rat ovary.

    PubMed

    Ferre, Céline; Belluco, Sara; Tinwell, Helen; Bars, Rémi; Benahmed, Mohamed; Rouquie, David; Schorsch, Frédéric

    2013-05-01

    Repeated exposure to 17-α-methyltestosterone (17MT) and estradiol benzoate (EB) for 28 or 90 days in rats induce similar ovarian atrophy. The objective of the present work was to identify and compare the early effects induced by 17MT and EB on the ovary using molecular and histopathological tools. Female rats were evaluated after 1, 3 or 7 days following an oral exposure by gavage at a daily dose of 600 mg/kg/day for 17MT and 5 mg/kg/day for EB. All animals were found to be acyclic after 3 or 7 days of treatment with 17MT and EB. Histopathological changes were present in the ovary, uterus, vagina and mammary gland after both treatments. Ovarian atrophy known as the long term effect of 17MT and EB was not yet detected after 7 days of treatment. But non regressive corpora lutea and cystic follicles were identically observed in the ovary of 17MT and EB treated females. Both compounds induced a decrease of LH transcripts together with an increase of plasma progesterone and prolactin levels. Differences in the profile of regulation of the aromatase were noted after 1 and 3 days of treatment in 17MT treated animals (upregulated) when compared to EB treated animals (downregulated). In summary, we have shown that despite the different nature of hormonal activity, EB and 17MT induce very early endocrine perturbation which presents several similarities. Our work indicated that the detection of early key hormonal markers in short term studies can help to predict the adverse long term effects on target tissues.

  17. Effects of Sodium Benzoate Treatment in Combination with An Extinction Training on the Maintenance of Cocaine-Supported Memory.

    PubMed

    Tsai, Yi-Ni; Tzeng, Wen-Yu; Cherng, Chianfang G; Liao, Tien You; Wu, Hsin-Hua; Lin, Jie-Kuan; Yu, Lung

    2016-02-29

    Activation of N-methyl-D-aspartate (NMDA) receptor can facilitate the extinction of various maladaptive memories. Sodium benzoate (NaB) has been known to enhance a naturally occurring full agonist on the glycine binding site of the NMDA receptor. This study aimed to test whether systemic NaB treatment can affect the extinction of a cocaine-supported memory, the cocaine-induced conditioned place preference (CPP). Following the establishment of the cocaine (10 mg/kg/conditioning × 3)-induced CPP, an extinction protocol, consisting of two consecutive extinction training bouts at an 8-h interval, was used. NaB (500 mg/kg) or an equivalent volume of saline was given immediately following each extinction training bout to test the modulating effect of NaB on the maintenance of cocaine-induced CPP. Moreover, NaB was bilaterally micro-infused into the medial prefrontal cortex (mPFC) to validate the involvement of this brain region in mediating systemic NaB treatment-produced effect on cocaine-induced CPP. Systemic (500 mg/kg) and intra-mPFC (10 μg/side) NaB treatment significantly decreased subsequent cocaine-induced CPP magnitude, although the NaB treatment or the extinction training alone did not affect such CPP magnitude. It was of importance to note that systemic or intra-mPFC NaB delivery did not affect mouse locomotor activity in the retests. These results, taken together, suggest that NaB treatment in combination with the extinction training may facilitate the extinction of the cocaine-supported memory. Moreover, systemic NaB treatment exerts such effects, at least in part, via its effect in the mPFC.

  18. Sodium benzoate, a metabolite of cinnamon and a food additive, upregulates ciliary neurotrophic factor in astrocytes and oligodendrocytes

    PubMed Central

    Modi, Khushbu K.; Jana, Malabendu; Mondal, Susanta; Pahan, Kalipada

    2015-01-01

    Ciliary neurotrophic factor (CNTF) is a promyelinating trophic factor that plays an important role in multiple sclerosis (MS). However, mechanisms by which CNTF expression could be increased in the brain are poorly understood. Recently we have discovered anti-inflammatory and immunomodulatory activities of sodium benzoate (NaB), a metabolite of cinnamon and a widely-used food additive. Here, we delineate that NaB is also capable of increasing the mRNA and protein expression of CNTF in primary mouse astrocytes and oligodendrocytes and primary human astrocytes. Accordingly, oral administration of NaB and cinnamon led to the upregulation of astroglial and oligodendroglial CNTF in vivo in mouse brain. Induction of experimental allergic encephalomyelitis (EAE), an animal model of MS, reduced the level of CNTF in the brain, which was restored by oral administration of cinnamon. While investigating underlying mechanisms, we observed that NaB induced the activation of protein kinase A (PKA) and H-89, an inhibitor of PKA, abrogated NaB-induced expression of CNTF. The activation of cAMP response element binding (CREB) protein by NaB, the recruitment of CREB and CREB-binding protein to the CNTF promoter by NaB and the abrogation of NaB-induced expression of CNTF in astrocytes by siRNA knockdown of CREB suggest that NaB increases the expression of CNTF via the activation of CREB. These results highlight a novel myelinogenic property of NaB and cinnamon, which may be of benefit for MS and other demyelinating disorders. PMID:26399250

  19. Development and validation of reversed-phase high-performance liquid chromatography method for estimation of rizatriptan benzoate in oral strip formulations

    PubMed Central

    Bhagawati, S. T.; Reddy, M. Sreenivasa; Avadani, Kiran; Muddukrishna, B.S.; Dengale, Swapnil J.; Bhat, Krishnamurthy

    2014-01-01

    Aim: A simple, accurate, precise, and reproducible reversed-phase high-performance liquid chromatography (RP-HPLC) method was developed and validated for the determination of rizatriptan benzoate in oral strip formulations. Methodology: Separation was achieved under optimized chromatographic condition on a Hiper C18 column (250 mm × 4.6 mm, 5 m) using Shimadzu HPLC. The mobile phase consisted of phosphate buffer (20 mM pH adjusted to 3.2 ± 0.005 with ortho phosphoric acid): Methanol in the ratio of 70:30 v/v with isocratic elution at a flow rate of 1 ml/min at ambient temperature was performed. The detection was carried out at 225 nm using photodiode array detector. The method was validated as per Q1A (R2) guidelines and suitability of developed method was ascertained by using optimized oral strip formulation. Results: The retention time of rizatriptan benzoate was found to be 5.17 min, and the calibration curve was linear in the concentration range of 0.20-20 mg/mL (r2= 0.9998). The limit of detection and the limit of quantitation were found to be 0.016 mg/mL and 0.0528 mg/mL, respectively. Method validation parameters were found to be within the specified limits. The percentage drug content of oral strips formulation was found to be 98.96 ± 1.37. Conclusion: The proposed HPLC method may be used efficiently for routine and quality control analysis of rizatriptan benzoate in pharmaceutical formulations. PMID:25538465

  20. The effects of a double blind, placebo controlled, artificial food colourings and benzoate preservative challenge on hyperactivity in a general population sample of preschool children

    PubMed Central

    Bateman, B; Warner, J; Hutchinson, E; Dean, T; Rowlandson, P; Gant, C; Grundy, J; Fitzgerald, C; Stevenson, J

    2004-01-01

    Aims: To determine whether artificial food colourings and a preservative in the diet of 3 year old children in the general population influence hyperactive behaviour. Methods: A sample of 1873 children were screened in their fourth year for the presence of hyperactivity at baseline (HA), of whom 1246 had skin prick tests to identify atopy (AT). Children were selected to form the following groups: HA/AT, not-HA/AT, HA/not-AT, and not-HA/not-AT (n = 277). After baseline assessment, children were subjected to a diet eliminating artificial colourings and benzoate preservatives for one week; in the subsequent three week within subject double blind crossover study they received, in random order, periods of dietary challenge with a drink containing artificial colourings (20 mg daily) and sodium benzoate (45 mg daily) (active period), or a placebo mixture, supplementary to their diet. Behaviour was assessed by a tester blind to dietary status and by parents' ratings. Results: There were significant reductions in hyperactive behaviour during the withdrawal phase. Furthermore, there were significantly greater increases in hyperactive behaviour during the active than the placebo period based on parental reports. These effects were not influenced by the presence or absence of hyperactivity, nor by the presence or absence of atopy. There were no significant differences detected based on objective testing in the clinic. Conclusions: There is a general adverse effect of artificial food colouring and benzoate preservatives on the behaviour of 3 year old children which is detectable by parents but not by a simple clinic assessment. Subgroups are not made more vulnerable to this effect by their prior levels of hyperactivity or by atopy. PMID:15155391

  1. Crystal structure of ethyl 4-[(E)-(4-hy-droxy-3-meth-oxy-benzyl-idene)amino]-benzoate: a p-hy-droxy Schiff base.

    PubMed

    Ling, Jing; Kavuru, Padmini; Wojtas, Lukasz; Chadwick, Keith

    2016-07-01

    The title p-hy-droxy Schiff base, C17H17NO4, was synthesized via the condensation reaction of benzocaine with vanillin. The benzyl-idine and benzoate rings are inclined to one another by 24.58 (8)°, and the conformation about the C=N bond is E. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming zigzag chains propagating along [010]. Adjacent chains are linked by C-H⋯π and weak offset π-π inter-actions [inter-centroid distance = 3.819 (1) Å], forming sheets parallel to (10-2).

  2. Transcription analysis of stx1, marA, and eaeA genes in Escherichia coli O157:H7 treated with sodium benzoate.

    PubMed

    Critzer, Faith J; Dsouza, Doris H; Golden, David A

    2008-07-01

    Expression of the multiple antibiotic resistance (mar) operon causes increased antimicrobial resistance in bacterial pathogens. The activator of this operon, MarA, can alter expression of >60 genes in Escherichia coli K-12. However, data on the expression of virulence and resistance genes when foodborne pathogens are exposed to antimicrobial agents are lacking. This study was conducted to determine transcription of marA (mar activator), stx1 (Shiga toxin 1), and eaeA (intimin) genes of E. coli O157:H7 EDL933 as affected by sodium benzoate. E. coli O157:H7 was grown in Luria-Bertani broth containing 0 (control) and 1% sodium benzoate at 37 degrees C for 24 h, and total RNA was extracted. Primers were designed for hemX (209 bp; housekeeping gene), marA (261 bp), and eaeA (223 bp) genes; previously reported primers were used for stx1. Tenfold dilutions of RNA were used in a real-time one-step reverse transcriptase PCR to determine transcription levels. All experiments were conducted in triplicate, and product detection was validated by gel electrophoresis. For marA and stx1, real-time one-step reverse transcriptase PCR products were detected at a 1-log-greater dilution in sodium benzoate-treated cells than in control cells, although cell numbers for each were similar (7.28 and 7.57 log CFU/ml, respectively). This indicates a greater (albeit slight) level of their transcription in treated cells than in control cells. No difference in expression of eaeA was observed. HemX is a putative uroporphyrinogen III methylase. The hemX gene was expressed at the same level in control and treated cells, validating hemX as an appropriate housekeeping marker. These data indicate that stx1 and marA genes could play a role in pathogen virulence and survival when treated with sodium benzoate, whereas eaeA expression is not altered. Understanding adaptations of E. coli O157:H7 during antimicrobial exposure is essential to better understand and implement methods to inhibit or control

  3. Loss of the toluene-xylene catabolic genes of TOL plasmid pWW0 during growth of Pseudomonas putida on benzoate is due to a selective growth advantage of 'cured' segregants.

    PubMed

    Williams, P A; Taylor, S D; Gibb, L E

    1988-07-01

    During growth on benzoate-minimal medium Pseudomonas putida mt-2 (PaW1) segregates derivative ('cured') strains which have lost the ability to use the pathway encoded by its resident catabolic plasmid pWW0. Experiments with two plasmids identical to pWW0 but each with an insert of Tn401, which confers resistance to carbenicillin, suggested that the 'benzoate curing' occurs far more frequently by the specific deletion of the 39 kbp region carrying the catabolic genes than by total plasmid loss. This effect was not pH-dependent, and was not produced during growth on other weak organic acids, such as succinate or propionate, or when benzoate was present in the medium with an alternative, preferentially used carbon source such as succinate. Growth on benzoate did not cause loss from strain PaW174 of the plasmid pWW0174, a derivative of pWW0 which has deleted the 39 kbp region but carries Tn401. Similarly the naphthalene-catabolic plasmid pWW60-1, of the same incompatibility group as pWW0, was not lost from PaW701 during growth on benzoate. Competition between wild-type PaW1 and PaW174, which has the 'cured' phenotype, showed that the latter has a distinct growth advantage on benzoate over the wild-type even when initially present as only 1% of the population: when PaW174 was seeded at lower cell ratios, spontaneously 'cured' derivatives of PaW1 took over the culture after 60-80 generations, indicating that they are present in PaW1 cultures at frequencies between 10(-2) and 10(-3). We conclude that the progressive takeover of populations of PaW1 only occurs when benzoate is present as the sole growth source and that neither benzoate, nor other weak acids, affect plasmid segregation or deletion events: a sufficient explanation is that the 'cured' segregants grow faster than the wild-type using the chromosomally determined beta-ketoadipate pathway.

  4. Effects of estradiol benzoate on 5'-iodothyronine deiodinase activities in female rat anterior pituitary gland, liver and thyroid gland.

    PubMed

    Lisbôa, P C; Curty, F H; Moreira, R M; Pazos-Moura, C C

    1997-12-01

    There is little information on the possible effects of estrogen on the activity of 5'-deiodinase (5'-ID), an enzyme responsible for the generation of T3, the biologically active thyroid hormone. In the present study, anterior pituitary sonicates or hepatic and thyroid microsomes from ovariectomized (OVX) rats treated or not with estradiol benzoate (EB, 0.7 or 14 micrograms/100 g body weight, s.c., for 10 days) were assayed for type I 5'-ID (5'-ID-I) and type II 5'-ID (5'-ID-II, only in pituitary) activities. The 5'-ID activity was evaluated by the release of 125I from deiodinated 125I rT3, using specific assay conditions for type I or type II. Serum TSH and free T3 and free T4 were measured by radioimmunoassay. OVX alone induced a reduction in pituitary 5'-ID-I (control = 723.7 +/- 67.9 vs OVX = 413.9 +/- 26.9; P < 0.05), while the EB-treated OVX group showed activity similar to that of the normal group. Thyroid 5'-ID-I showed the same pattern of changes, but these changes were not statistically significant. Pituitary and hepatic 5'-ID-II did not show major alterations. The treatment with the higher EB dose (14 micrograms), contrary to the results obtained with the lower dose, had no effect on the reduced pituitary 5'-ID-I of OVX rats. However, it induced an important increment of 5'-ID-I in the thyroid gland (0.8 times higher than that of the normal group: control = 131.9 +/- 23.7 vs OVX + EB 14 micrograms = 248.0 +/- 31.2; P < 0.05), which is associated with increased serum TSH (0.6-fold vs OVX, P < 0.05) but normal serum free T3 and free T4. The data suggest that estrogen is a physiological stimulator of anterior pituitary 5'-ID-I and a potent stimulator of the thyroid enzyme when employed at high doses.

  5. Detectability of testosterone esters and estradiol benzoate in bovine hair and plasma following pour-on treatment.

    PubMed

    Stolker, A A M; Groot, M J; Lasaroms, J J P; Nijrolder, A W J M; Blokland, M H; Riedmaier, I; Becker, C; Meyer, H H D; Nielen, M W F

    2009-10-01

    The abuse of synthetic esters of natural steroids such as testosterone and estradiol in cattle fattening and sports is hard to detect via routine urine testing. The esters are rapidly hydrolysed in vivo into substances which are also endogenously present in urine. An interesting alternative can be provided by the analysis of the administered synthetic steroids themselves, i.e., the analysis of intact steroid esters in hair by liquid chromatography tandem mass spectrometry (LC/MS/MS). However, retrospective estimation of the application date following a non-compliant finding is hindered by the complexity of the kinetics of the incorporation of steroid esters in hair. In this study, the incorporation of intact steroid esters in hair following pour-on treatment has been studied and critically compared with results from intramuscular treatment. To this end animals were pour-on treated with a hormone cocktail containing testosterone cypionate, testosterone decanoate and estradiol benzoate in different carriers. The animals were either treated using injection and pour-on application once or three times having 1 week between treatments using injection and pour-on application. Animals were slaughtered from 10-12 weeks after the last treatment. Both hair and blood plasma samples were collected and analysed by LC/MS/MS. From the results, it is concluded that after single treatment the levels of steroid esters in hair drop to CCbeta levels (5-20 microg/kg) after 5-7 weeks. When treatment is repeated two times, the CCbeta levels are reached after 9-11 weeks. Furthermore, in plasma, no steroid esters were detected; not even at the low microgramme per litre level but--in contrast with the pour-on application--after i.m. injection, significant increase of 17beta-testosterone and 17beta-estradiol were observed. These observations suggest that transport of steroid esters after pour-on application is not only performed by blood but also by alternative fluids in the animal so

  6. Oestradiol-17β plasma concentrations after intramuscular injection of oestradiol benzoate or oestradiol cypionate in llamas (Lama glama)

    PubMed Central

    2010-01-01

    Background Llamas (Lama glama) are induced ovulators and the process of ovulation depends on dominant follicular size. In addition, a close relationship between behavioural estrus and ovulation is not registered in llamas. Therefore, the exogenous control of follicular development with hormones aims to predict the optimal time to mate. Oestradiol-17β (E2) and its esters are currently used in domestic species, including camelids, in synchronization treatments. But, in llamas, there is no reports regarding the appropriate dosages to be used and most protocols have been designed by extrapolation from those recommended for other ruminants. The aim of the present study was to characterize plasma E2 concentrations in intact female llamas following a single intramuscular (i.m.) injection of two oestradiol esters: oestradiol benzoate (EB) and oestradiol cypionate (ECP). Methods Twelve non pregnant and non lactating sexually mature llamas were i.m. injected on day 0 with 2.5 mg of EB (EB group, n = 6) or ECP (ECP group, n = 6). Blood samples were collected immediately before injection, at 1, 6, 12, 24 h after treatment and then daily until day 14 post injection. Changes in hormone concentrations with time were analyzed in each group by analysis of variance (ANOVA) using a repeated measures (within-SS) design. Plasma E2 concentrations and area under the concentration-time curve (AUC) values were compared between groups by ANOVA. In all cases a Least-Significant Difference test (LSD) was used to determine differences between means. Hormonal and AUC data are expressed as mean ± S.E.M. Results Peak plasma E2 concentrations were achieved earlier and were higher in EB group than in ECP group. Thereafter, E2 returned to physiological concentrations earlier in EB group (day 5) than in ECP group (day 9). Although plasma E2 profiles differed over time among groups there were no differences between them on AUC values. Conclusions The i.m. injection of a single dose of both

  7. 78 FR 18519 - Abamectin; Pesticide Tolerances

    Federal Register 2010, 2011, 2012, 2013, 2014

    2013-03-27

    ... onions, chives, dry beans, and okra. Acute anticipated residues for the remaining commodities were... were used for bulb onions, chives, dry beans, and and okra. Average residues from field trials...

  8. 76 FR 69653 - Abamectin (avermectin); Pesticide Tolerances

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-11-09

    ... crops and okra and anticipated residues for the remaining commodities. Empirical processing factors and... okra, and average residues from field trials for the remaining crops. Empirical processing factors...

  9. Inhibitor effects of sodium benzoate on corrosion resistance of Al6061-B4C composites in NaCl and H3BO3 solutions

    NASA Astrophysics Data System (ADS)

    Rafi-ud-din; Shafqat, Q. A.; Shahzad, M.; Ahmad, Ejaz; Asghar, Z.; Rafiq, Nouman; Qureshi, A. H.; Syed, Waqar adil; asim Pasha, Riffat

    2016-12-01

    Sodium benzoate (SB) is used for the first time to inhibit the corrosion of Al6061-B4C composites in H3BO3 and NaCl solutions. Al6061100-x -x wt% B4C (x = 0, 5, and 10) composites are manufactured by a powder metallurgy route. The corrosion inhibition efficiency of SB is investigated as a function of the volume fractions of B4C particles by using potentiodynamic polarization and electrochemical impedance techniques. Without the use of an inhibitor, an increase of the B4C particles in the composite decreases the corrosion resistance of Al6061-B4C composites. It is found that SB is an efficient corrosion inhibitor for Al6061-B4C composites in both investigated solutions. The corrosion inhibition efficiency of SB increases with an increase in B4C content. Since SB is an adsorption type inhibitor, it is envisaged that an extremely thin layer of molecules adsorbs onto the surface and suppresses the oxidation and reduction. It is found that the inhibitor effect of SB is more pronounced in a H3BO3 environment than in NaCl solution. Further, the mechanism of corrosion inhibition by SB is illustrated by using optical and scanning electron microscopy of corroded samples. It is found that the adsorption of benzoate ions on the Al surface and its bonding with Al3+ ions forms a hydrophobic layer on top of the exposed Al surface, which enhances the protection against dissolved boride ions.

  10. Identification of halogenated photoproducts generated after ultraviolet-irradiation of parabens and benzoates in water containing chlorine by solid-phase microextraction and gas chromatography-mass spectrometry.

    PubMed

    Alvarez-Rivera, Gerardo; Llompart, Maria; Garcia-Jares, Carmen; Lores, Marta

    2014-07-04

    This work presents a new solid-phase microextraction (SPME)-based approach to investigate the formation of halogenated by-products generated by the UV-induced photodegradation of parabens and their congener benzoates in water containing chlorine. Degradation of parent species, and further identification of their transformation by-products were monitored by gas chromatography coupled to mass spectrometry (GC/MS). In order to improve detectability, SPME was applied as a preconcentration step after UV-irradiation of target preservatives. Experiments performed with dechlorinated water, ultrapure water, and tap water showed that under UV-light, the presence of even low levels of free chlorine, increases the photodegradation rate of target preservatives, enhancing the formation of halogenated photoproducts. Monobrominated, dibrominated and bromochlorinated hydroxybenzoates were identified, and the transformation of benzoates into halogenated parabens was also confirmed. Bromination is expected to occur when free chlorine is present, due to the presence of traces of bromide in water samples. Five halogenated phenols (mainly brominated) were detected as breakdown photoproducts from both families of target preservatives. On the basis of the appearance of the aforementioned by-products, a tentative transformation pathway, consistent with the photoformation-photodecay kinetics of the by-products, is proposed herein for the first time.

  11. Fixation of chiral smectic liquid crystal (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate using UV curing techniques

    SciTech Connect

    Afrizal, Nurdelima,; Umeir; Hikam, Muhammad; Soegiyono, Bambang; Riswoko, Asep

    2014-03-24

    Chiral Smectic Liquid Crystal (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate has been synthesized using method of steglich esterification at room temperature. The mesomorphic behavior of chiral smectic at 55°C that showed schlieren texture in POM analysis. Fixation of structure chiral smectic liquid crystal by means of photopolymerization of monomer (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate under UV irradiation which called UV curing techniques. The curing process using UV 3 lamps 100 volt at 60°C for an hour. The product of photopolymerization could be seen by analysis of FTIR spectra both monomer and polymer. FTIR spectra of monomer, two peaks for ester carbonyl and C-C double bond groups appeared at 1729.09 cm-1and 3123.46 cm{sup −1}. After UV curing process, peak for the carbonyl group at 1729.09 cm{sup −1} decreased and a new peak at 1160.21 cm{sup −1} appeared due to the carbonyl group attached to a C-C bond group and then peak at 3123.46 cm{sup −1} for C-C double bond group was disappeared.

  12. Low-temperature Heat Capacities and Thermodynamic Properties of Crystalline 2-Aminopyridinium Benzoate (C12H12N2O2) (s).

    PubMed

    He, Dong-Hua; Di, You-Ying; Dan, Wen-Yan; Liu, Yu-Pu; Wang, Da-Qi

    2010-06-01

    2-Aminopyridinium benzoate was synthesized. Chemical analysis, elemental analysis, and X-ray crystallography were applied to characterize the composition and crystal structure of the compound. The lattice potential energy of the title compound was calculated to be UPOT = 284.297 kJ mol-1. Low-temperature heat capacities of the compound were measured by a precision automatic adiabatic calorimeter over the temperature range from 78 K to 365 K. A polynomial equation of heat capacities against the temperature in the region of 78 K to 365 K was fitted by a least square method. Based on the fitted polynomial equation, the smoothed heat capacities and thermodynamic functions of the compound relative to the standard reference temperature 298.15 K were calculated at intervals of 5 K. According to the synthesis reaction, the standard molar enthalpies of dissolution for the reactants and product in the selected solvent were measured by an isoperibol solution-reaction calorimeter, respectively. Accordingly, the enthalpy change of the synthesis reaction was calculated to be ΔrHom = -(20.016 ± 0.182) kJ mol-1. Finally, the standard molar enthalpy of formation of 2-aminopyridinium benzoate was determined to be ΔfHom = - (365.416 ± 0.961) kJ mol-1 in accordance with Hess law.

  13. Efficacy of Four Nematicides Against the Reproduction and Development of Pinewood Nematode, Bursaphelenchus xylophilus.

    PubMed

    Bi, Zhenzhen; Gong, Yanting; Huang, Xiaojuan; Yu, Hongshi; Bai, Liqun; Hu, Jiafu

    2015-06-01

    To understand the efficacy of emamectin benzoate, avermectin, milbemectin, and thiacloprid on the reproduction and development of Bursaphelenchus xylophilus, seven parameters, namely population growth, fecundity, egg hatchability, larval lethality, percent larval development, body size, and sexual ratio, were investigated using sublethal (LC20) doses of these compounds in the laboratory. Emamectin benzoate treatment led to a significant suppression in population size, brood size, and percent larval development with 411, 3.50, and 49.63%, respectively, compared to 20850, 24.33, and 61.43% for the negative control. The embryonic and larval lethality increased obviously from 12.47% and 13.70% to 51.37% and 75.30%, respectively. In addition, the body length was also significantly reduced for both males and females in the emamectin benzoate treatment. Avermectin and milbemectin were also effective in suppressing population growth by increasing larval lethality and reducing larval development, although they did not affect either brood size or embryonic lethality. Body length for both male and female worms was increased by avermectin. Thiacloprid caused no adverse reproductive effects, although it suppressed larval development. Sexual ratio was not affected by any of these four nematicides. Our results indicate that emamectin benzoate, milbemectin, and avermectin are effective against the reproduction of B. xylophilus. We think these three nematicides can be useful for the control of pine wilt disease.

  14. Efficacy of Four Nematicides Against the Reproduction and Development of Pinewood Nematode, Bursaphelenchus xylophilus

    PubMed Central

    Bi, Zhenzhen; Gong, Yanting; Huang, Xiaojuan; Yu, Hongshi; Bai, Liqun; Hu, Jiafu

    2015-01-01

    To understand the efficacy of emamectin benzoate, avermectin, milbemectin, and thiacloprid on the reproduction and development of Bursaphelenchus xylophilus, seven parameters, namely population growth, fecundity, egg hatchability, larval lethality, percent larval development, body size, and sexual ratio, were investigated using sublethal (LC20) doses of these compounds in the laboratory. Emamectin benzoate treatment led to a significant suppression in population size, brood size, and percent larval development with 411, 3.50, and 49.63%, respectively, compared to 20850, 24.33, and 61.43% for the negative control. The embryonic and larval lethality increased obviously from 12.47% and 13.70% to 51.37% and 75.30%, respectively. In addition, the body length was also significantly reduced for both males and females in the emamectin benzoate treatment. Avermectin and milbemectin were also effective in suppressing population growth by increasing larval lethality and reducing larval development, although they did not affect either brood size or embryonic lethality. Body length for both male and female worms was increased by avermectin. Thiacloprid caused no adverse reproductive effects, although it suppressed larval development. Sexual ratio was not affected by any of these four nematicides. Our results indicate that emamectin benzoate, milbemectin, and avermectin are effective against the reproduction of B. xylophilus. We think these three nematicides can be useful for the control of pine wilt disease. PMID:26170474

  15. A redetermination from the original data of the crystal structure of 2-amino-4,6-di-meth-oxy-pyrimidin-1-ium 4-amino-benzoate.

    PubMed

    Fábry, Jan

    2016-04-01

    The title structure, C6H9.5N3O2 (0.5+)·C7H6.5NO2 (0.5-), which might be named schematically as 2-amino-4,6-di-meth-oxy-pyrimidine-(μ2-hydrogen)-4-amino-benzoate to indicate a bridging H atom, has been redetermined from the data published by Thanigaimani, Mu-thiah & Lynch [Acta Cryst. (2006), E62, o2976-o2978]. The improvement of the present redetermination consists in a released geometry of the primary amine groups, which were originally assumed to be planar, as well as in a redetermination of the position of the hy-droxy H atom. This H atom, whose parameters were originally constrained, turns out to be situated about the centre of the O⋯N hydrogen bond in two disordered positions with occupancies of 0.5 each.

  16. Bis(tetra-methyl-amonium) bis-(2,4,5-carboxy-benzoate)-benzene-1,2,4,5-tetra-carboxylic acid (1/1).

    PubMed

    Cunha-Silva, Luís; Girginova, Penka I; Trindade, Tito; Rocha, João; Klinowski, Jacek; Almeida Paz, Filipe A

    2007-12-06

    The asymmetric unit of the title compound, 2C(4)H(12)N(+)·2C(10)H(5)O(8) (-)·C(10)H(6)O(8), consists of a tetra-methyl-amonium cation, an anion derived from the singly deprotonated pyromellitic acid anion, 2,4,5-carboxy-benzoate (H(3)bta(-)), and one-half of a benzene-1,2,4,5-tetra-carboxylic acid (H(4)bta) mol-ecule, which has the centroid of the aromatic ring positioned at a crystallographic centre of inversion. The H(4)bta and H(3)bta(-) residues are involved in an extensive inter-molecular O-H⋯O hydrogen-bonding network, which leads to a three-dimensional supra-molecular structure containing one-dimensional channels running parallel to the [001] crystallographic direction. These channels house the tetra-methyl-amonium cations.

  17. Excess parameters for binary mixtures of ethyl benzoate with 1-propanol, 1-butanol and 1-pentanol at T=303, 308, 313, 318, and 323 K

    NASA Astrophysics Data System (ADS)

    Sreehari Sastry, S.; Babu, Shaik; Vishwam, T.; Parvateesam, K.; Sie Tiong, Ha.

    2013-07-01

    Various thermo-acoustic parameters, such as excess isentropic compressibility (KsE), excess molar volume (VE), excess free length (LfE), excess Gibb's free energy (ΔG*E), and excess Enthalpy (HE), have been calculated from the experimentally determined data of density, viscosity and speed of sound for the binary mixtures of ethyl benzoate+1-propanol, or +1-butanol, or +1-pentanol over the entire range of composition at different temperatures (303, 308, 313, 318 and 323 K). The excess functions have been fitted to the Redlich-Kister type polynomial equation. The deviations for excess thermo-acoustic parameters have been explained on the basis of the intermolecular interactions present in these binary mixtures.

  18. Multi-photon absorption effect and intra-molecular charge transfer of donor-π-acceptor chromophore ethyl p-amino benzoate.

    PubMed

    Sajan, D; Vijayan, N; Safakath, K; Philip, Reji; Karabacak, M

    2013-05-01

    Fourier transform (FT)-Raman and infrared (IR) spectra of the nonlinear optical (NLO) material ethyl p-amino benzoate (EPAB) have been recorded and analyzed. The geometry and harmonic vibrational wavenumbers are calculated with the help of B3LYP density functional theory method. The detailed interpretation of the vibrational spectra has been carried out with the aid of normal coordinate analysis following the scaled quantum mechanical force field methodology. Stability of the molecule arising from hyperconjugative interactions leading to its NLO activity and charge delocalization have been analyzed using natural bond orbital (NBO) analysis. Employing the open-aperture z-scan technique, NLO absorption of the sample has been studied in two excitation regimes, using 100 fs and 5 ns laser pulses respectively. It is found that EPAB is a three-photon absorber for 100 fs pulses at the excitation wavelength of 800 nm. For ns pulses at 532 nm it exhibits strong optical limiting, indicating possible photonics applications.

  19. Simultaneous Determination of Potassium Sorbate, Sodium Benzoate, Quinoline Yellow and Sunset Yellow in Lemonades and Lemon Sauces by HPLC Using Experimental Design.

    PubMed

    Dinç Zor, Şule; Aşçı, Bürge; Aksu Dönmez, Özlem; Yıldırım Küçükkaraca, Dilek

    2016-07-01

    In this study, development and validation of a HPLC method was described for simultaneous determination of potassium sorbate, sodium benzoate, quinoline yellow and sunset yellow. A Box-Behnken design using three variables at three levels was employed to determine the optimum conditions of chromatographic separation: pH of mobile phase, 6.0-7.0; flow rate, 0.8-1.2 mL min(-1) and the ratio of mobile phase composed of a 0.025 M sodium acetate/acetic acid buffer, 80-90%. Resolution was chosen as a response. The optimized method was validated for linearity, the limits of detection and quantification, accuracy, precision and stability. All the validation parameters were within the acceptance range. The applicability of the developed method to the determination of these food additives in commercial lemonade and lemon sauce samples was successfully demonstrated.

  20. Crystal structure of zwitterionic 4-(ammonio­methyl)­benzoate: a simple mol­ecule giving rise to a complex supra­molecular structure

    PubMed Central

    Atria, Ana María; Garland, Maria Teresa; Baggio, Ricardo

    2014-01-01

    The asymmetric unit of the title compound, C8H9NO2·H2O consists of an isolated 4-(ammonio­meth­yl)benzoate zwitterion derived from 4-amino­methyl­benzoic acid through the migration of the acidic proton, together with a water molecule of crystallization that is disordered over three sites with occupancy ratios (0.50:0.35:0.15). In the crystal structure, N—H⋯O hydrogen bonds together with π–π stacking of the benzene rings [centroid–centroid distance = 3.8602 (18) Å] result in a strongly linked, compact three-dimensional structure. PMID:25484753

  1. Genetic Analysis of Natural Variation in Antirrhinum Scent Profiles Identifies BENZOIC ACID CARBOXYMETHYL TRANSFERASE As the Major Locus Controlling Methyl Benzoate Synthesis

    PubMed Central

    Ruiz-Hernández, Victoria; Hermans, Benjamin; Weiss, Julia; Egea-Cortines, Marcos

    2017-01-01

    The Antirrhinum genus has a considerable complexity in the scent profiles produced by different species. We have analyzed the genetic differences between A. majus and A. linkianum, two species divergent in the emission of methyl benzoate, methyl cinnamate, acetophenone, and ocimene. The genetic analysis showed that all compounds segregated in a Mendelian fashion attributable to one or two loci with simple or epistatic interactions. Several lines lacked methyl benzoate, a major Volatile Organic Compound emitted by A. majus but missing in A. linkianum. Using a candidate gene approach, we found that the BENZOIC ACID CARBOXYMETHYL TRANSFERASE from A. linkianum appeared to be a null allele as we could not detect mRNA expression. The coding region did not show significant differences that could explain the loss of expression. The intron-exon boundaries was also conserved indicating that there is no alternative splicing in A. linkianum as compared to A. majus. However, it showed multiple polymorphisms in the 5′ promoter region including two insertions, one harboring an IDLE MITE transposon with additional sequences with high homology to the PLENA locus and a second one with somewhat lower homology to the regulatory region of the VENOSA locus. It also had a 778 bp deletion as compared to the A. majus BAMT promoter region. Our results show that the differences in scent emission between A. majus and A. linkianum may be traced back to single genes involved in discrete biosynthetic reactions such as benzoic acid methylation. Thus, natural variation of this complex trait maybe the result of combinations of wild type, and loss of function alleles in different genes involved in discrete VOCs biosynthesis. Furthermore, the presence of active transposable elements in the genus may account for rapid evolution and instability, raising the possibility of adaptation to local pollinators. PMID:28154577

  2. Genetic Analysis of Natural Variation in Antirrhinum Scent Profiles Identifies BENZOIC ACID CARBOXYMETHYL TRANSFERASE As the Major Locus Controlling Methyl Benzoate Synthesis.

    PubMed

    Ruiz-Hernández, Victoria; Hermans, Benjamin; Weiss, Julia; Egea-Cortines, Marcos

    2017-01-01

    The Antirrhinum genus has a considerable complexity in the scent profiles produced by different species. We have analyzed the genetic differences between A. majus and A. linkianum, two species divergent in the emission of methyl benzoate, methyl cinnamate, acetophenone, and ocimene. The genetic analysis showed that all compounds segregated in a Mendelian fashion attributable to one or two loci with simple or epistatic interactions. Several lines lacked methyl benzoate, a major Volatile Organic Compound emitted by A. majus but missing in A. linkianum. Using a candidate gene approach, we found that the BENZOIC ACID CARBOXYMETHYL TRANSFERASE from A. linkianum appeared to be a null allele as we could not detect mRNA expression. The coding region did not show significant differences that could explain the loss of expression. The intron-exon boundaries was also conserved indicating that there is no alternative splicing in A. linkianum as compared to A. majus. However, it showed multiple polymorphisms in the 5' promoter region including two insertions, one harboring an IDLE MITE transposon with additional sequences with high homology to the PLENA locus and a second one with somewhat lower homology to the regulatory region of the VENOSA locus. It also had a 778 bp deletion as compared to the A. majus BAMT promoter region. Our results show that the differences in scent emission between A. majus and A. linkianum may be traced back to single genes involved in discrete biosynthetic reactions such as benzoic acid methylation. Thus, natural variation of this complex trait maybe the result of combinations of wild type, and loss of function alleles in different genes involved in discrete VOCs biosynthesis. Furthermore, the presence of active transposable elements in the genus may account for rapid evolution and instability, raising the possibility of adaptation to local pollinators.

  3. LC/MS study of the UV filter hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]-benzoate (DHHB) aquatic chlorination with sodium hypochlorite.

    PubMed

    Grbović, G; Trebše, P; Dolenc, D; Lebedev, A T; Sarakha, M

    2013-11-01

    The fate of modern personal care products in the environment is becoming a matter of increasing concern because of the growing production and assortment of these compounds. More and more chemicals of this class are treated as emerging contaminants. Transformation of commercially available products in the environment may result in the formation of a wide array of their metabolites. Personal care products in swimming pools and in drinking water reservoirs may undergo oxidation or chlorination. There is much data on the formation of more toxic metabolites from original low toxicity commercial products. Therefore, reliable identification of all possible transformation products and a thorough study of their physicochemical and biological properties are of high priority. The present study deals with the identification of the products of the aquatic chlorination of the hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]-benzoate ultraviolet filter. High-performance liquid chromatography/mass spectrometry (HPLC/MS) and HPLC/MS/MS with accurate mass measurements were used for this purpose. As a result, three chlorinated transformation products were identified.

  4. The Gibbs free energy of formation of halogenated benzenes, benzoates and phenols and their potential role as electron acceptors in anaerobic environments.

    PubMed

    Dolfing, Jan; Novak, Igor

    2015-02-01

    The sequence of redox reactions in the natural environment generally follows the electron affinity of the electron acceptors present and can be rationalized by the redox potentials of the appropriate half-reactions. Answering the question how halogenated aromatics fit into this sequence requires information on their Gibbs free energy of formation values. In 1992 Gibbs free energy data for various classes of halogenated aromatic compounds were systematically explored for the first time based on Benson's group contribution method. Since then more accurate quantum chemical calculation methods have become available. Here we use these methods to estimate enthalpy and Gibbs free energy of formation values of all chlorinated and brominated phenols. These data and similar state-of-the-art datasets for halogenated benzenes and benzoates were then used to calculate two-electron redox potentials of halogenated aromatics for standard conditions and for pH 7. The results underline the need to take speciation into consideration when evaluating redox potentials at pH 7 and highlight the fact that halogenated aromatics are excellent electron acceptors in aqueous environments.

  5. Characterization of process-related impurities including forced degradation products of alogliptin benzoate and the development of the corresponding reversed-phase high-performance liquid chromatography method.

    PubMed

    Zhou, YuXia; Zhou, WenTao; Sun, LiLi; Zou, QiaoGen; Wei, Ping; OuYang, PingKai

    2014-06-01

    The characterization of process-related impurities and forced degradants of alogliptin benzoate (Alb) in bulk drugs and a stability-indicating HPLC method for the separation and quantification of all the impurities were investigated. Alb was found to be unstable under acid and alkali stress conditions and two major degradation products (Imp-F and Imp-G) were observed. The optimum separation was achieved on Kromasil C18 (250 × 4.6 mm, 5 μm) using 0.1% perchloric acid (pH adjusted to 3.0 with triethylamine) and acetonitrile as a mobile phase in gradient mode. The proposed method was found to be stability indicating, precise, linear (0.10-75.0 μg/mL), accurate, sensitive, and robust for the quantitation of Alb and its process-related substances and degradation products. The structures of 11 impurities were characterized and confirmed by NMR spectroscopy, MS, and IR spectroscopy, and the most probable formation mechanisms of all impurities were proposed according to the synthesis route.

  6. Inhibitory Effect of Methyl 2-(4'-Methoxy-4'-oxobutanamide) Benzoate from Jerusalem Artichoke (Helianthus tuberosus) on the Inflammatory Paracrine Loop between Macrophages and Adipocytes.

    PubMed

    Jung, Yun Joo; Kim, Byung Oh; Kwak, Jong Hwan; Pyo, Suhkneung

    2016-12-14

    The interaction between macrophages and adipocytes is known to aggravate inflammation of the adipose tissue, leading to decreased insulin sensitivity. Hence, attenuation of the inflammatory paracrine loop between macrophages and adipocytes is deemed essential to ameliorate insulin resistance and diabetes mellitus type 2. Methyl 2-(4'-methoxy-4'-oxobutanamide) benzoate (compound 1), a newly isolated compound from Jerusalem srtichoke (JA), has not been biologically characterized yet. Here, we investigated whether JA-derived compound 1 attenuates the inflammatory cycle between RAW 264.7 macrophages and 3T3-L1 adipocytes. Compound 1 suppressed the inflammatory response of RAW 264.7 cells to lipopolysaccharide through decreased secretion of IL-1β, IL-6, and TNF-α. Moreover, the mRNA expression of TNF-α, IL-6, IL-1β, MCP-1, and Rantes and MAPK pathway activation in 3T3-L1 adipocytes, incubated in macrophage-conditioned media, were inhibited. These findings suggest an anti-inflammatory effect of a newly extracted compound against adipose tissue inflammation and insulin resistance.

  7. Food additives: Sodium benzoate, potassium sorbate, azorubine, and tartrazine modify the expression of NFκB, GADD45α, and MAPK8 genes.

    PubMed

    Raposa, B; Pónusz, R; Gerencsér, G; Budán, F; Gyöngyi, Z; Tibold, A; Hegyi, D; Kiss, I; Koller, Á; Varjas, T

    2016-09-01

    It has been reported that some of the food additives may cause sensitization, inflammation of tissues, and potentially risk factors in the development of several chronic diseases. Thus, we hypothesized that expressions of common inflammatory molecules - known to be involved in the development of various inflammatory conditions and cancers - are affected by these food additives. We investigated the effects of commonly used food preservatives and artificial food colorants based on the expressions of NFκB, GADD45α, and MAPK8 (JNK1) from the tissues of liver. RNA was isolated based on Trizol protocol and the activation levels were compared between the treated and the control groups. Tartrazine alone could elicit effects on the expressions of NFκB (p = 0.013) and MAPK8 (p = 0.022). Azorubine also resulted in apoptosis according to MAPK8 expression (p = 0.009). Preservatives were anti-apoptotic in high dose. Sodium benzoate (from low to high doses) dose-dependently silenced MAPK8 expression (p = 0.004 to p = 0.002). Addition of the two preservatives together elicited significantly greater expression of MAPK8 at half-fold dose (p = 0.002) and at fivefold dose (p = 0.008). This study suggests that some of the food preservatives and colorants can contribute to the activation of inflammatory pathways.

  8. Metallo-porphyrazines with eight [5-thiopentyl 3,4,5-tris(benzyloxy)benzoate] groups: Synthesis, characterization, aggregation, and solubility behavior

    NASA Astrophysics Data System (ADS)

    Gonca, Ergün

    2017-02-01

    Metal-free and metallo-porphyrazines having eight 5-hydroxypentylthio units at the peripheral positions have been prepared from 2,3-bis(5-hydroxypentylthio)maleonitrile. By the esterification reaction of magnesium hydroxy-porphyrazine with 3,4,5-tris(benzyloxy)benzoic acid in dicyclohexylcarbodiimide and toluene-p-sulfonic acid, the reactivity of the hydroxypentyl units was indicated. On the other hand, iron porphyrazine derivatives with eight [5-thiopentyl 3,4,5-tris(benzyloxy)benzoate] groups attached to the periphery positions were synthesized. By the reaction of metal-free porphyrazine with iron (II) acetate and further processing with HCl solution, FePzCl was obtained. Finally, by reacting FePzCl with pyridine or pyrazine, [FePz(py)2] and [FePz(pyz)]n complexes were prepared, respectively. The characterizations of target complexes were carried out by utilizing different spectroscopic methods such as FT-IR, UV-vis, mass, 1H NMR, and 13C NMR together with elemental analysis.

  9. Comparison of aminolysis of 2-pyridyl and 4-pyridyl x-substituted benzoates in acetonitrile: evidence for a concerted mechanism involving a cyclic transition state.

    PubMed

    Um, Ik-Hwan; Bae, Ae-Ri; Um, Tae-Il

    2014-02-07

    A kinetic study on reactions of 2-pyridyl X-substituted benzoates (6a-i) with a series of cyclic secondary amines in MeCN is reported. The Hammett plot for the reaction of 6a-i with piperidine consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX = 1.28 and r = 0.63, indicating that the nonlinear Hammett plot is not caused by a change in the rate-determining step but rather by resonance stabilization of substrates possessing an electron-donating group (EDG) in the benzoyl moiety. The Brønsted-type plots are linear with βnuc = 0.59 ± 0.02, which is typical of reactions reported to proceed through a concerted mechanism. A cyclic transition state (TS), which forces the reaction to proceed through a concerted mechanism, is proposed. The deuterium kinetic isotope effect of 1.3 ± 0.1 is consistent with the proposed mechanism. Analysis of activation parameters reveals that ΔH(‡) increases linearly as the substituent X changes from an electron-withdrawing group (EWG) to an EDG, while TΔS(‡) remains nearly constant with a large negative value. The constant TΔS(‡) value further supports the proposal that the reaction proceeds through a concerted mechanism with a cyclic TS.

  10. Determination of hormonal growth promoters in bovine hair: comparison of liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry methods for estradiol benzoate and nortestosterone decanoate.

    PubMed

    Duffy, Eleanor; Rambaud, Lauriane; Le Bizec, Bruno; O'Keeffe, Michael

    2009-04-01

    The detection of steroid residues in hair is a powerful strategy to demonstrate long-term administration of these growth promoters in meat production animals. Analysis of the ester form of administered steroids is an unambiguous approach to prove the illegal use of natural hormones. For detection, gas chromatography-mass spectrometry (GC-MS/MS) was generally used. However, recent advances in liquid chromatography-tandem mass spectrometry (LC-MS/MS) technology have improved the robustness and potential sensitivity of this method. This paper describes development and validation, according to Commission Decision 2002/657/EC, of LC-MS/MS and GC-MS/MS methods, in two separate laboratories, for determination of steroid esters in bovine hair. Bovine hair samples taken from animals treated with estradiol-3-benzoate and nortestosterone decanoate, as well as from an untreated animal, were used to evaluate the comparability of the results of the two validated methods. The results of the inter-comparison demonstrate that both the LC-MS/MS and the GC-MS/MS methods are fit for purpose and capable of determining steroid esters in hair samples from treated bovine animals.

  11. Simultaneous LC-MS/MS determination of phenylbutyrate, phenylacetate benzoate and their corresponding metabolites phenylacetylglutamine and hippurate in blood and urine.

    PubMed

    Laryea, Maurice D; Herebian, Diran; Meissner, Thomas; Mayatepek, Ertan

    2010-12-01

    Inborn errors of urea metabolism result in hyperammonemia. Treatment of urea cycle disorders can effectively lower plasma ammonium levels and results in survival in the majority of patients. Available medications for treating urea cycle disorders include sodium benzoate (BA), sodium phenylacetate (PAA), and sodium phenylbutyrate (PBA) and are given to provide alternate routes for disposition of waste nitrogen excretion. In this study, we develop and validate a liquid chromatography tandem mass spectrometry (LC-MS/MS) method for simultaneous determination of benzoic acid, phenylacetic acid, phenylbutyric acid, phenylacetylglutamine, and hippuric acid in plasma and urine from children with inborn errors of urea synthesis. Plasma extracts and diluted urine samples were injected on a reverse-phase column and identified and quantified by selected reaction monitoring (SRM) in negative ion mode. Deuterated analogues served as internal standards. Analysis time was 7 min. Assay precision, accuracy, and linearity and sample stability were determined using enriched samples. Quantification limits of the method were 100 ng/ml (0.3-0.8 μmol/L) for all analytes, and recoveries were >90%. Inter- and intraday relative standard deviations were <10%. Our newly developed LC-MS/MS represents a robust, sensitive, and rapid method that allows simultaneous determination of the five compounds in plasma and urine.

  12. An electrochemical sensor for rizatriptan benzoate determination using Fe3O4 nanoparticle/multiwall carbon nanotube-modified glassy carbon electrode in real samples.

    PubMed

    Madrakian, Tayyebeh; Maleki, Somayeh; Heidari, Mozhgan; Afkhami, Abbas

    2016-06-01

    In this paper a sensitive and selective electrochemical sensor for determination of rizatriptan benzoate (RZB) was proposed. A glassy carbon electrode was modified with nanocomposite of multiwalled carbon nanotubes (MWCNTs) and Fe3O4 nanoparticles (Fe3O4/MWCNTs/GCE). The results obtained clearly show that the combination of MWCNTs and Fe3O4 nanoparticles definitely improves the sensitivity of modified electrode to RZB determination. The morphology and electroanalytical performance of the fabricated sensor were characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), energy dispersive X-ray spectroscopy (EDS), square wave voltammetry (SWV) and cyclic voltammetry (CV). Also, the effect of experimental and instrumental parameters on the sensor response was evaluated. The square wave voltammetric response of the electrode to RZB was linear in the range 0.5-100.0 μmol L(-1) with a detection limit of 0.09 μmol L(-1) under the optimum conditions. The investigated method showed good stability, reproducibility and repeatability. The proposed sensor was successfully applied for real life samples of blood serum and RZB determination in pharmaceutical.

  13. Crystal structure of bis-(tri-ethano-lamine-κ(3) N,O,O')nickel(II) bis-(3-hy-droxy-benzoate) tetra-hydrate.

    PubMed

    Ibragimov, Aziz B

    2016-05-01

    The reaction of 3-hy-droxy-benzoic (m-hy-droxy-benzoic) acid (MHBA), tri-ethano-lamine (TEA) and Ni(NO3)2 in aqueous solution led to formation of the hydrated title salt, [Ni(C6H15NO3)2](C7H5O3)·4H2O. In the complex cation, the Ni(2+) ion is located on an inversion centre. Two symmetry-related TEA ligands occupy all coordination sites in an N,O,O'-tridentate coordination, leading to a slightly distorted NiN2O4 octa-hedron. Two ethanol groups of each TEA ligand form two five-membered chelate rings around Ni(2+), while the third ethanol group does not coordinate to the metal atom. Two MHBA(-) anions in the benzoate form are situated in the outer coordination sphere for charge compensation. An intricate network of hydrogen bonds between the free and coordinating hy-droxy groups of the TEA ligands, the O atoms of the MHBA(-) anions and the water mol-ecules leads to the formation of a two-dimensional structure extending parallel to (010).

  14. H-bond and dipole-dipole interactions between water and COO functional group in methyl benzoate derivatives: Substituent and heteroatom effects.

    PubMed

    Sarhadinia, S; Ebrahimi, A

    2016-11-01

    Interactions of COOCH3 functional group of methyl benzoate (MB) and its derivatives can substantially be affected by substituents and heteroatoms. The substituent and heteroatom effects on the intermolecular interactions in the complexes of MB and its derivatives with the water molecule have been investigated by the quantum mechanical calculations in the present study. Electron donating (ED)/electron withdrawing (EW) substituents increase/decrease the binding energy (ΔEbin) between mentioned functional group and hydrogen bond donor, and the N heteroatom in the six membered ring weakens the effect. The effects of the N heteroatoms depend on their positions in the ring, and the effects of substituents depend on the number and the positions of heteroatoms. Some relations were obtained between the dipole moment of carbonyl group, results obtained from the natural bond orbital (NBO) and the atoms in molecules (AIM) analysis, binding energy and Hammett constants of substituents. The results can be used to predict the factors affect the intermolecular interactions, and to improve the ligand-protein bindings in biological systems.

  15. 40 CFR 180.505 - Emamectin; tolerances for residues.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...). Commodity Parts per million Cattle, fat 0.010 Cattle, liver 0.050 Cattle, meat 0.003 Cattle, meat byproducts, except liver 0.020 Goat, fat 0.010 Goat, liver 0.050 Goat, meat 0.003 Goat, meat byproducts, except liver 0.020 Hog, fat 0.003 Hog, liver 0.020 Hog, meat 0.002 Hog, meat byproducts (except liver)...

  16. 40 CFR 180.505 - Emamectin; tolerances for residues.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ..., fat 0.010 Cattle, liver 0.050 Cattle, meat 0.003 Cattle, meat byproducts, except liver 0.020 Goat, fat 0.010 Goat, liver 0.050 Goat, meat 0.003 Goat, meat byproducts, except liver 0.020 Hog, fat 0.003 Hog, liver 0.020 Hog, meat 0.002 Hog, meat byproducts (except liver) 0.005 Horse, fat 0.010...

  17. 40 CFR 180.505 - Emamectin; tolerances for residues.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...). Commodity Parts per million Cattle, fat 0.010 Cattle, liver 0.050 Cattle, meat 0.003 Cattle, meat byproducts, except liver 0.020 Goat, fat 0.010 Goat, liver 0.050 Goat, meat 0.003 Goat, meat byproducts, except liver 0.020 Hog, fat 0.003 Hog, liver 0.020 Hog, meat 0.002 Hog, meat byproducts (except liver)...

  18. 40 CFR 180.505 - Emamectin; tolerances for residues.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., fat 0.010 Cattle, liver 0.050 Cattle, meat 0.003 Cattle, meat byproducts, except liver 0.020 Goat, fat 0.010 Goat, liver 0.050 Goat, meat 0.003 Goat, meat byproducts, except liver 0.020 Hog, fat 0.003 Hog, liver 0.020 Hog, meat 0.002 Hog, meat byproducts (except liver) 0.005 Horse, fat 0.010...

  19. 40 CFR 180.505 - Emamectin; tolerances for residues.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., fat 0.010 Cattle, liver 0.050 Cattle, meat 0.003 Cattle, meat byproducts, except liver 0.020 Goat, fat 0.010 Goat, liver 0.050 Goat, meat 0.003 Goat, meat byproducts, except liver 0.020 Hog, fat 0.003 Hog, liver 0.020 Hog, meat 0.002 Hog, meat byproducts (except liver) 0.005 Horse, fat 0.010...

  20. Ovarian dynamics in response to two modified intravaginal progesterone releasing device and oestradiol benzoate based ovulation synchronisation protocols designed for use in Brahman heifers.

    PubMed

    Edwards, S A A; Atkinson, P C; Satake, N; Boe-Hansen, G; McGowan, M R

    2014-07-01

    The objective was to investigate the ovarian response of Brahman heifers to two modified ovulation synchronisation protocols developed to increase the proportion of normal synchronous ovulations. Experiment 1 characterised the growth of the ovulatory follicle in heifers (n=19) treated with an intravaginal progesterone releasing device (IPRD) and oestradiol benzoate (ODB), to determine the optimal time to induce ovulation. Using the findings from Experiment 1, Experiment 2 investigated the effect of reducing the duration of IPRD insertion and increasing the interval from IPRD removal to ODB treatment (modified protocol 1 - OPO-6; n=20), and omitting ODB treatment at the time of IPRD insertion (modified protocol 2 - PO-6; n=20). An IPRD (0.78 g progesterone) was inserted at Day 0 (OPO-8) or Day 2 (OPO-6 and PO-6) and all heifers also received 1 mg ODB i.m. Day 8: IPRD removed + 500 μg cloprostenol i.m. At 24 h (OPO-8) and 36 h (OPO-6 and PO-6) post IPRD removal: 1 mg ODB i.m. Fixed-time AI (FTAI) occurred at 54 h for OPO-8 and 72 h for OPO-6 and PO-6, post IPRD removal. After IPRD treatment all OPO-6 and OPO-8 heifers initiated a new follicular wave whereas 25% of PO-6 heifers failed. Diameter of the dominant follicle was larger at FTAI in the PO-6 (11.34 ± 0.50 mm) compared to the OPO-8 protocol (9.74 ± 0.51 mm; P<0.05), but similar to the OPO-6 protocol (10.52 ± 0.51 mm). Proportion of ovulations occurring 12 h prior and 24 h post FTAI was similar for the PO-6 (80%) and OPO-6 (75%) protocols but numerically lower in the OPO-8 heifers (60%). The apparent improvement in ovarian response in heifers treated with the modified protocols needs to be confirmed in larger field studies.

  1. Ovarian responses in Bos indicus heifers treated to synchronise ovulation with intravaginal progesterone releasing devices, oestradiol benzoate, prostaglandin F(2α) and equine chorionic gonadotrophin.

    PubMed

    Butler, S A A; Phillips, N J; Boe-Hansen, G B; Bo, G A; Burns, B M; Dawson, K; McGowan, M R

    2011-12-01

    The objectives were: (i) improve understanding of the ovarian responses of Bos indicus heifers treated with different ovulation synchronisation protocols, (ii) compare ovarian responses of B. indicus heifers treated with intravaginal progesterone releasing device (IPRD)+oestradiol benzoate (ODB) versus a conventional prostaglandin F(2α) (PGF(2α)) protocol and (iii) investigate whether reducing the amount of progesterone (P(4)) in the IPRD, and treatment with equine chorionic gonadotrophin (eCG) would increase the proportion of heifers with normal ovarian function during the synchronised and return cycles. Two-year-old Brahman (n=30) and Brahman-cross (n=34) heifers were randomly allocated to three IPRD-treatment groups: (i) standard-dose IPRD (Cue-Mate(®) 1.56g P(4); n=17); (ii) half-dose IPRD (Cue-Mate(®) 0.78g P(4); n=15); (iii) half-dose IPRD+300IU eCG at IPRD removal (n=14), and a non-IPRD control group (iv) 2×PGF(2α) (500μg cloprostenol) on Days -16 and -2 (n=18). IPRD-treated heifers received 250μg cloprostenol at IPRD insertion (Day -10) and IPRD removal (Day -2) and 1mg ODB on Days -10 and -1. Ovarian function was evaluated by ultrasonography and plasma P(4) throughout the synchronised and return cycles. The mean diameter of the dominant follicle observed at 54-56h after IPRD removal, was greater for heifers which ovulated than heifers which did not ovulate (P<0.001; 14.5±1.1 vs. 9.3±0.6mm, respectively). The prevalence of IPRD-treated heifers with ovarian dysfunction (persistent CL, failure to re-ovulate, shortened luteal phase) was 39%. This relatively high prevalence of ovarian dysfunction may explain the commonly reported, lower than expected pregnancy rates to FTAI in B. indicus heifers treated to synchronise ovulation.

  2. Sodium Benzoate, a Food Additive and a Metabolite of Cinnamon, Enriches Regulatory T Cells via STAT6-Mediated Upregulation of TGF-β.

    PubMed

    Kundu, Madhuchhanda; Mondal, Susanta; Roy, Avik; Martinson, Jeffrey L; Pahan, Kalipada

    2016-10-15

    Upregulation and/or maintenance of regulatory T cells (Tregs) during autoimmune insults may have therapeutic efficacy in autoimmune diseases. Earlier we have reported that sodium benzoate (NaB), a metabolite of cinnamon and a Food and Drug Administration-approved drug against urea cycle disorders, upregulates Tregs and protects mice from experimental allergic encephalomyelitis, an animal model of multiple sclerosis. However, mechanisms by which NaB increases Tregs are poorly understood. Because TGF-β is an important inducer of Tregs, we examined the effect of NaB on the status of TGF-β. In this study, we demonstrated that NaB induced the expression of TGF-β mRNA and protein in normal as well as proteolipid protein-primed splenocytes. The presence of a consensus STAT6 binding site in the promoter of the TGF-β gene, activation of STAT6 in splenocytes by NaB, recruitment of STAT6 to the TGF-β promoter by NaB, and abrogation of NaB-induced expression of TGF-β in splenocytes by small interfering RNA knockdown of STAT6 suggest that NaB induces the expression of TGF-β via activation of STAT6. Furthermore, we demonstrated that blocking of TGF-β by neutralizing Abs abrogated NaB-mediated protection of Tregs and experimental allergic encephalomyelitis. These studies identify a new function of NaB in upregulating TGF-β via activation of STAT6, which may be beneficial in MS patients.

  3. Synergistic Potentiation of Cystic Fibrosis Transmembrane Conductance Regulator Gating by Two Chemically Distinct Potentiators, Ivacaftor (VX-770) and 5-Nitro-2-(3-Phenylpropylamino) Benzoate.

    PubMed

    Lin, Wen-Ying; Sohma, Yoshiro; Hwang, Tzyh-Chang

    2016-09-01

    Cystic fibrosis (CF) is caused by loss-of-function mutations of the cystic fibrosis transmembrane conductance regulator (CFTR) gene encoding a phosphorylation-activated but ATP-gated chloride channel. Previous studies suggested that VX-770 [ivacaftor, N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide], a CFTR potentiator now used in clinics, increases the open probability of CFTR by shifting the gating conformational changes to favor the open channel configuration. Recently the chloride channel blocker and CFTR potentiator 5-nitro-2-(3-phenylpropylamino) benzoate (NPPB) has been reported to enhance CFTR activity by a mechanism that exploits the ATP hydrolysis-driven, nonequilibrium gating mechanism unique to CFTR. Surprisingly however, NPPB increased the activity of nonhydrolytic G551D-CFTR, the third most common disease-associated mutation. Here, we further investigated the mechanism of NPPB's effects on CFTR gating by assessing its interaction with well-studied VX-770. Interestingly, once G551D-CFTR was maximally potentiated by VX-770, NPPB further increased its activity. However, quantitative analysis of this drug-drug interaction suggests that this pharmacologic synergism is not due to independent actions of NPPB and VX-770 on CFTR gating; instead, our data support a dependent mechanism involving two distinct binding sites. This latter idea is further supported by the observation that the locked-open time of a hydrolysis-deficient mutant K1250A was shortened by NPPB but prolonged by VX-770. In addition, the effectiveness of NPPB, but not of VX-770, was greatly diminished in a mutant whose second nucleotide-binding domain was completely removed. Interpreting these results under the framework of current understanding of CFTR gating not only reveals insights into the mechanism of action for different CFTR potentiators but also brings us one step forward to a more complete schematic for CFTR gating.

  4. Structural and spectroscopic characterization of 1-(diaminomethylene) thiouron-1-ium benzoate and bis(1-(diaminomethylene)thiouron-1-ium) phthalate trihydrate

    NASA Astrophysics Data System (ADS)

    Perpétuo, Genivaldo Julio; Janczak, Jan

    2016-02-01

    Two single crystals of 1-(diaminomethylene) thiouron-1-ium benzoate (1) and bis(1-(diaminomethylene)thiouron-1-ium) phthalate trihydrate (2) were grown using a solution growth technique. The compound 1 crystallises in the centrosymmetric P21/c space group of the monoclinic system, whereas the compound 2 in the centrosymmetric Pbcn space group of orthorhombic system. The solid-state organisation of 1 and 2 has been analysed with respect to cation-anion and hydrogen bonding interactions. The oppositely charged units interact via almost linear hydrogen bonds with the graphs of R22(8) and R21(6) forming molecular complexes. In the crystal 1 the R22(8) motif is formed by donation to the carboxylate group from amine group joined to C1 and from imine group and R21(6) motif is formed by donation to the O2 from amine group joined to C2 and from imine group, whereas in crystal 2 the graphs are formed oppositely. Interactions between the hydrogen-bonded molecular complexes in 1 lead to formation of layered 2D structure, whereas in 2, due to presence of hydrated water molecules lead to formation of 3D hydrogen-bonded supramolecular network. The obtained deuterated analogues of 1 and 2 crystallise similar as H-compound in the monoclinic and orthorhombic system with quite similar lattice parameters. The compounds were also characterised by the FT-IR and Raman spectroscopies. The characteristic bands of the functional and skeletal groups are discussed.

  5. Effects of Exposure to Estradiol Benzoate or Flutamide at the Weaning Age on Expression of Connexins in the Caudal Epididymis of Adult Rat

    PubMed Central

    Lee, Ki-Ho

    2016-01-01

    ABSTRACT The present research was chiefly designed to determine the effect of the treatment of estrogenic agonist, estradiol benzoate (EB), or antiandrogenic compound, flutamide (Flu), at the weaning age on the expression of connexin (Cx) isoforms in the caudal epididymis of adult male rat. Animals were subcutaneously administrated with a single shot of either EB at a low-dose (0.015 µg of EB/kg body weight (BW)) or a high-dose (1.5 µg of EB/kg BW) or Flu at a low-dose (500 µg of EB/kg BW) or a high-dose (5 mg of EB/kg BW). Expressional changes of Cx isoforms in the adult caudal epididymis were examined by quantitative real-time PCR analysis. The treatment of a low-dose EB caused significant increases of Cx30.3, Cx31, Cx32, and Cx43 transcript levels but reduction of Cx31.1, Cx37, and Cx45 expression. Exposure to a high-dose EB resulted in very close responses observed in a low-dose EB treatment, except no significant expressional change of Cx37 and a significant induction of Cx40. Expression of all Cx isoforms, except Cx45, was significantly increased by a low-dose Flu treatment. Expressional increases of all Cx isoforms were detected by a high-dose Flu treatment. The current study demonstrates that a single exposure to estrogenic or antiandrogenic compound during the early postnatal developmental period is sufficient to disrupt normal expression of Cx isoforms in the adult caudal epididymis. PMID:28144639

  6. Cinnamon and Its Metabolite Sodium Benzoate Attenuate the Activation of p21rac and Protect Memory and Learning in an Animal Model of Alzheimer's Disease.

    PubMed

    Modi, Khushbu K; Roy, Avik; Brahmachari, Saurabh; Rangasamy, Suresh B; Pahan, Kalipada

    2015-01-01

    This study underlines the importance of cinnamon, a commonly used natural spice and flavoring material, and its metabolite sodium benzoate (NaB) in attenuating oxidative stress and protecting memory and learning in an animal model of Alzheimer's disease (AD). NaB, but not sodium formate, was found to inhibit LPS-induced production of reactive oxygen species (ROS) in mouse microglial cells. Similarly, NaB also inhibited fibrillar amyloid beta (Aβ)- and 1-methyl-4-phenylpyridinium(+)-induced microglial production of ROS. Although NaB reduced the level of cholesterol in vivo in mice, reversal of the inhibitory effect of NaB on ROS production by mevalonate, and geranylgeranyl pyrophosphate, but not cholesterol, suggests that depletion of intermediates, but not end products, of the mevalonate pathway is involved in the antioxidant effect of NaB. Furthermore, we demonstrate that an inhibitor of p21rac geranylgeranyl protein transferase suppressed the production of ROS and that NaB suppressed the activation of p21rac in microglia. As expected, marked activation of p21rac was observed in the hippocampus of subjects with AD and 5XFAD transgenic (Tg) mouse model of AD. However, oral feeding of cinnamon (Cinnamonum verum) powder and NaB suppressed the activation of p21rac and attenuated oxidative stress in the hippocampus of Tg mice as evident by decreased dihydroethidium (DHE) and nitrotyrosine staining, reduced homocysteine level and increased level of reduced glutathione. This was accompanied by suppression of neuronal apoptosis, inhibition of glial activation, and reduction of Aβ burden in the hippocampus and protection of memory and learning in transgenic mice. Therefore, cinnamon powder may be a promising natural supplement in halting or delaying the progression of AD.

  7. Mycoflora of two types of Portuguese dry-smoked sausages and inhibitory effect of sodium benzoate, potassium sorbate, and methyl p-hydroxybenzoate on mold growth rate.

    PubMed

    Matos, T J S; Jensen, B B; Bernardo, F M A; Barreto, A H S; Hojberg, O

    2007-06-01

    The mycoflora of chouriqo types Alentejano and Ribatejano, two varieties of Portuguese dry-smoked sausages, have been investigated after a producer-defined shelf life period (120 days at 20 +/- 5 degrees C) in modified atmosphere packaging (55% N2 and 45% CO2). On the basis of morphological and physiological characteristics, the isolates were identified as Penicillium, Aspergillus, Fusarium, Rhizopus, Monilia, Absidia, and Cephalosporium. The species identified were as follows: Penicillium terrestres (43.4%), Penicillium sp. (13.3%), Fusarium sp. (10%), Aspergillus glaucus (10%), Aspergillus versicolor (6.8%), Monilia fruticola (3.3%), Absidia sp. (3.3%), Cephalosporium sp. (3.3%), Rhizopus stolonifer (3.3%), and Fusarium tricinctum (3.3%). Additionally, the effects of three preservatives (potassium sorbate [PS], sodium benzoate [SB], and methyl p-hydroxybenzoate [MHB]) were studied on the growth rate of mold representative isolates. MHB showed a greater inhibitory effect than SB and PS in all fungi isolates, except in A. glaucus [Tm30(A)], in which the inhibitory effect of MHB was similar to PS. At 0.05% (wt/vol), all fungi were inhibited with MHB, except for R. stolonifer [Tm25(A)], which started to decrease the growth rate only at a concentration higher than 0.1%. PS was more effective at inhibiting mold growth than SB, except in Absidia sp. [Tm16(R)], in which both showed a similar inhibitory effect. MHB showed great promise as an application to the surface at 0.1% (wt/vol) to improve the stability and safety of the product through the inhibition of potential spoilage and toxigenic molds.

  8. Food additives such as sodium sulphite, sodium benzoate and curcumin inhibit leptin release in lipopolysaccharide-treated murine adipocytes in vitro.

    PubMed

    Ciardi, Christian; Jenny, Marcel; Tschoner, Alexander; Ueberall, Florian; Patsch, Josef; Pedrini, Michael; Ebenbichler, Christoph; Fuchs, Dietmar

    2012-03-01

    Obesity leads to the activation of pro-inflammatory pathways, resulting in a state of low-grade inflammation. Recently, several studies have shown that the exposure to lipopolysaccharide (LPS) could initiate and maintain a chronic state of low-grade inflammation in obese people. As the daily intake of food additives has increased substantially, the aim of the present study was to investigate a potential influence of food additives on the release of leptin, IL-6 and nitrite in the presence of LPS in murine adipocytes. Leptin, IL-6 and nitrite concentrations were analysed in the supernatants of murine 3T3-L1 adipocytes after co-incubation with LPS and the food preservatives, sodium sulphite (SS), sodium benzoate (SB) and the spice and colourant, curcumin, for 24 h. In addition, the kinetics of leptin secretion was analysed. A significant and dose-dependent decrease in leptin was observed after incubating the cells with SB and curcumin for 12 and 24 h, whereas SS decreased leptin concentrations after 24 h of treatment. Moreover, SS increased, while curcumin decreased LPS-stimulated secretion of IL-6, whereas SB had no such effect. None of the compounds that were investigated influenced nitrite production. The food additives SS, SB and curcumin affect the leptin release after co-incubation with LPS from cultured adipocytes in a dose- and time-dependent manner. Decreased leptin release during the consumption of nutrition-derived food additives could decrease the amount of circulating leptin to which the central nervous system is exposed and may therefore contribute to an obesogenic environment.

  9. Changes in Expression of Connexin Isoforms in the Caudal Epididymis of Adult Sprague-Dawley Rats exposed to Estradiol Benzoate or Flutamide at the Neonatal Age

    PubMed Central

    Lee, Ki-Ho

    2016-01-01

    Direct communication between neighboring cells via gap junction in tissue is important for maintenance and regulation of its physiological functions. Each epididymal region has different composition of cell types. It is well recognized that the epididymis is a steroid hormone-responsive tissue. The present study was designed to determine the effect of estradiol benzoate (EB) or flutamide exposured at the early postnatal age on the expression of connexin (Cx) isoforms in the caudal epididymis. The EB or flutamide was subcutaneously administrated to male Spragure Dawley rat at 7 days of age, and expressional changes of Cx isoforms in the adult corpus epididymis were determined by quantitative real-time PCR. The treatment of low-dose EB resulted in decreases of Cx30.3, Cx31.1, Cx37, and Cx45 expression but caused an increase of Cx32 expression. Exposure to high-dose EB led into expressional increases of Cx31, Cx31.1, Cx32, Cx40, and Cx43, even though a decrease of Cx37 expression was found with a high-dose EB treatment. A low-dose flutamide induced increases of Cx31, Cx31.1, Cx32, and Cx43 expression but a decrease of Cx37 expression. Expression of most Cx genes were significantly increased by a high-dose flutamide, while no expressional change of Cx26 and Cx40 was detected by a high-dose flutamide. These results indicate that expression of Cx isoforms in the caudal epididymis is altered by exposure to steroidal compounds at the prepubertal age. It is suggested that a contact with environmental exogenous materials during the early postnatal period would lead to alteration of epididymal functions at the adult. PMID:27796005

  10. Addition of fumaric acid and sodium benzoate as an alternative method to achieve a 5-log reduction of Escherichia coli O157:H7 populations in apple cider.

    PubMed

    Comes, Justin E; Beelman, Robert B

    2002-03-01

    A study was conducted to develop a preservative treatment capable of the Food and Drug Administration-mandated 5-log reduction of Escherichia coli O157:H7 populations in apple cider. Unpreserved apple cider was treated with generally recognized as safe acidulants and preservatives before inoculation with E. coli O157:H7 in test tubes and subjected to mild heat treatments (25, 35, and 45 degrees C) followed by refrigerated storage (4 degrees C). Fumaric acid had significant (P < 0.05) bactericidal effect when added to cider at 0.10% (wt/vol) and adjusted to pH 3.3, but citric and malic acid had no effect. Strong linear correlation (R2 = 0.96) between increasing undissociated fumaric acid concentrations and increasing log reductions of E. coli O157:H7 in apple cider indicated the undissociated acid to be the bactericidal form. The treatment that achieved the 5-log reduction in three commercial ciders was the addition of fumaric acid (0.15%, wt/vol) and sodium benzoate (0.05%, wt/vol) followed by holding at 25 degrees C for 6 h before 24 h of refrigeration at 4 degrees C. Subsequent experiments revealed that the same preservatives added to cider in flasks resulted in a more than 5-log reduction in less than 5 and 2 h when held at 25 and 35 degrees C, respectively. The treatment also significantly (P < 0.05) reduced total aerobic counts in commercial ciders to populations less than those of pasteurized and raw ciders from the same source (after 5 and 21 days of refrigerated storage at 4 degrees C, respectively). Sensory evaluation of the same ciders revealed that consumers found the preservative-treated cider to be acceptable.

  11. Signal-regulator interactions. Genetic analysis of the effector binding site of xylS, the benzoate-activated positive regulator of Pseudomonas TOL plasmid meta-cleavage pathway operon.

    PubMed

    Ramos, J L; Michan, C; Rojo, F; Dwyer, D; Timmis, K

    1990-01-20

    This study reports a genetic analysis of the interactions between a positive regulator of gene expression and its effector molecules. Transcription of the TOL plasmid meta-cleavage pathway operon is specifically stimulated by the XylS protein positive regulator either through activation of this regulator by benzoate effectors or through its hyperproduction. One xylS mutant that exhibits constitutive expression of the operon promoter has been characterized, together with six mutants encoding altered XylS proteins that recognize as effectors benzoate analogues that are non-effectors for the XylS wild-type protein. The changes in two mutant regulators are located at the N-terminal end of the protein, within a putative beta-pleated domain. These mutant proteins exhibit a markedly increased affinity for normal benzoate effectors, with K's values fivefold to 60-fold lower than those of the wild-type XylS protein. They are additionally activated by new effectors having certain substituents at position 2, 3 and 4 of the aromatic ring. Two other mutant proteins recognize new effectors having substituents at position 4 and 5 of the aromatic ring, and contain mutations at their C-terminal end within a putative alpha-helix-rich domain. Three other mutations, one of which leads to constitutive expression from Pm, each result in an amino acid change in the central region of the regulator. These findings suggest but do not prove that the effector binding pocket of the XylS protein may be composed of two or more non-contiguous segments of its primary structure. The XylS protein exhibits homology with the AraC protein of Escherichia coli, a protein that stimulates transcription from ara promoters when it is activated by arabinose or benzoate. Mutations influencing effector activation of the XylS protein characterized in this study are all located in regions exhibiting a high degree of homology with the corresponding aligned sequence of AraC protein.

  12. Translational diffusion in sucrose benzoate near the glass transition: Probe size dependence in the breakdown of the Stokes-Einstein equation

    NASA Astrophysics Data System (ADS)

    Rajian, Justin Rajesh; Quitevis, Edward L.

    2007-06-01

    The translational diffusion coefficient Dtrans for rubrene, 9,10-bis(phenylethynyl)anthracene (BPEA), and tetracene in the fragile molecular glass-former sucrose benzoate (SB) (Tg=337K) was studied as a function of temperature from Tg+3KtoTg+71K by use of the holographic fluorescence recovery after photobleaching technique. The values of Dtrans vary by five to six orders of magnitude in this temperature range. Contrary to the predictions of the Stokes-Einstein equation, the temperature dependence of probe diffusion in SB over the temperature range of the measurements is weaker than that of T /η, where η is the shear viscosity. In going from the crossover temperature Tx≈1.2Tg to Tg, Dtransη/T increases by factors of 2.4±0.2 decades for rubrene, 3.4±0.2 decades for BPEA, and 3.8±0.4 decades for tetracene. The decoupling between probe diffusion in SB and viscosity is characterized by the scaling law Dtrans˜T/ηξ, with ξ =0.621 for tetracene, 0.654 for BPEA, and 0.722 for rubrene. Data for probe diffusion in SB are combined with data from the literature for probe diffusion in ortho-terphenyl and ααβ-tris(naphthyl)benzene in a plot of enhancement versus the relative probe size parameter ρm=(mp/mh)1/3, where mp and mh are, respectively, the molecular weights of the probe and host solvent. The plot clearly shows a sharp increase in enhancement of translational diffusion at ρm≈1. By applying temperature shifts, Dtrans for probe diffusion in SB and the dielectric relaxation time τD can be superimposed on a single master curve based on the Williams-Landel-Ferry equation. This suggests that the dynamics of probe diffusion in SB is described by the scaling relationship Dtrans˜1/τD(T +ΔT), where τD(T+ΔT) is the temperature-shifted dielectric relaxation time. The results from this study are discussed within the context of dynamic heterogeneity in glass-forming liquids.

  13. Translational diffusion in sucrose benzoate near the glass transition: probe size dependence in the breakdown of the Stokes-Einstein equation.

    PubMed

    Rajian, Justin Rajesh; Quitevis, Edward L

    2007-06-14

    The translational diffusion coefficient D(trans) for rubrene, 9,10-bis(phenylethynyl)anthracene (BPEA), and tetracene in the fragile molecular glass-former sucrose benzoate (SB) (Tg=337 K) was studied as a function of temperature from Tg+3 K to Tg+71 K by use of the holographic fluorescence recovery after photobleaching technique. The values of D(trans) vary by five to six orders of magnitude in this temperature range. Contrary to the predictions of the Stokes-Einstein equation, the temperature dependence of probe diffusion in SB over the temperature range of the measurements is weaker than that of T/eta, where eta is the shear viscosity. In going from the crossover temperature Tx approximately 1.2Tg to Tg, D(trans)eta/T increases by factors of 2.4+/-0.2 decades for rubrene, 3.4+/-0.2 decades for BPEA, and 3.8+/-0.4 decades for tetracene. The decoupling between probe diffusion in SB and viscosity is characterized by the scaling law D(trans) approximately T/eta(xi), with xi=0.621 for tetracene, 0.654 for BPEA, and 0.722 for rubrene. Data for probe diffusion in SB are combined with data from the literature for probe diffusion in ortho-terphenyl and alphaalphabeta-tris(naphthyl)benzene in a plot of enhancement versus the relative probe size parameter rho(m)=(m(p)m(h))(1/3), where m(p) and m(h) are, respectively, the molecular weights of the probe and host solvent. The plot clearly shows a sharp increase in enhancement of translational diffusion at rho(m) approximately 1. By applying temperature shifts, D(trans) for probe diffusion in SB and the dielectric relaxation time tau(D) can be superimposed on a single master curve based on the Williams-Landel-Ferry equation. This suggests that the dynamics of probe diffusion in SB is described by the scaling relationship D(trans) approximately 1/tau(D)(T+DeltaT), where tau(D)(T+DeltaT) is the temperature-shifted dielectric relaxation time. The results from this study are discussed within the context of dynamic heterogeneity in

  14. Preclinical Pharmacokinetics, Tissue Distribution, and Plasma Protein Binding of Sodium (±)-5-Bromo-2-(α-Hydroxypentyl) Benzoate (BZP), an Innovative Potent Anti-ischemic Stroke Agent

    PubMed Central

    Tian, Xin; Li, Hong-Meng; Wei, Jing-Yao; Liu, Bing-Jie; Zhang, Yu-Hai; Wang, Gao-Ju; Chang, Jun-Biao; Qiao, Hai-Ling

    2016-01-01

    Sodium (±)-5-bromo-2-(α-hydroxypentyl) benzoate (BZP) is a potential cardiovascular drug and exerts potent neuroprotective effect against transient and long-term ischemic stroke in rats. BZP could convert into 3-butyl-6-bromo-1(3H)-isobenzofuranone (Br-NBP) in vitro and in vivo. However, the pharmacokinetic profiles of BZP and Br-NBP still have not been evaluated. For the purpose of investigating the pharmacokinetic profiles, tissue distribution, and plasma protein binding of BZP and Br-NBP, a rapid, sensitive, and specific method based on liquid chromatography coupled to mass spectrometry (LC-MS/MS) has been developed for determination of BZP and Br-NBP in biological samples. The results indicated that BZP and Br-NBP showed a short elimination half-life, and pharmacokinetic profile in rats (3, 6, and 12 mg/kg; i.v.) and beagle dogs (1, 2, and 4 mg/kg; i.v.gtt) were obtained after single dosing of BZP. After multiple dosing of BZP, there was no significant accumulation of BZP and Br-NBP in the plasma of rats and beagle dogs. Following i.v. single dose (6 mg/kg) of BZP to rats, BZP and Br-NBP were distributed rapidly into all tissues examined, with the highest concentrations of BZP and Br-NBP in lung and kidney, respectively. The brain distribution of Br-NBP in middle cerebral artery occlusion (MCAO) rats was more than in normal rats (P < 0.05). The plasma protein binding degree of BZP at three concentrations (8000, 20,000, and 80,000 ng/mL) from rat, beagle dog, and human plasma were 98.1–98.7, 88.9–92.7, and 74.8–83.7% respectively. In conclusion, both BZP and Br-NBP showed short half-life, good dose-linear pharmacokinetic profile, wide tissue distribution, and different degree protein binding to various species plasma. This was the first preclinical pharmacokinetic investigation of BZP and Br-NBP in both rats and beagle dogs, which provided vital guidance for further preclinical research and the subsequent clinical trials. PMID:27588003

  15. Alternative solvent-based methyl benzoate vortex-assisted dispersive liquid-liquid microextraction for the high-performance liquid chromatographic determination of benzimidazole fungicides in environmental water samples.

    PubMed

    Santaladchaiyakit, Yanawath; Srijaranai, Supalax

    2014-11-01

    Vortex-assisted dispersive liquid-liquid microextraction using methyl benzoate as an alternative extraction solvent for extracting and preconcentrating three benzimidazole fungicides (i.e., carbendazim, thiabendazole, and fluberidazole) in environmental water samples before high-performance liquid chromatographic analysis has been developed. The selected microextraction conditions were 250 μL of methyl benzoate containing 300 μL of ethanol, 1.0% w/v sodium acetate, and vortex agitation speed of 2100 rpm for 30 s. Under optimum conditions, preconcentration factors were 14.5-39.0 for the target fungicides. Limits of detection were obtained in the range of 0.01-0.05 μg/L. The proposed method was then applied to surface water samples and the recovery evaluations at three spiked concentration levels of 5, 30, and 50 μg/L were obtained in the range of 77.4-110.9% with the relative standard deviation <7.4%. The present method was simple, rapid, low cost, sensitive, environmentally friendly, and suitable for the trace analysis of the studied fungicides in environmental water samples.

  16. Assessment of insecticide resistance of Lobesia botrana (Lepidoptera: Tortricidae) in Emilia-Romagna region.

    PubMed

    Civolani, Stefano; Boselli, Mauro; Butturini, Alda; Chicca, Milvia; Fano, Elisa Anna; Cassanelli, Stefano

    2014-06-01

    The European grapevine moth, Lobesia botrana (Denis & Schiffermüller) (Lepidoptera: Tortricidae), is the key pest of vineyard, Vitis vinifera L. In Italy, failures in field chemical pest control have been recently reported. The susceptibility to insecticides indoxacarb, methoxyfenozide, and emamectin benzoate was then evaluated in a L. botrana population collected from a vineyard in Emilia-Romagna (northeastern Italy) where pest management programs achieved unsatisfactory results. The field trial showed that the indoxacarb efficacy toward L. botrana was very low in the two timings of application (7.9 and -1.5%) in comparison with untreated control, while the efficacy of methoxyfenozide (76.1%) and emamectin benzoate (88.8%) was high. The decreased efficacy of indoxacarb was also supported by the results of the laboratory bioassay on neonate L. botrana larvae, in which the resistance ratio was 72-fold in comparison with that of the susceptible strain.

  17. Effect of estradiol benzoate used at the start of a progestagen treatment on superovulatory response and embryo yield in lactating and non-lactating llamas.

    PubMed

    Aller, J F; Cancino, A K; Rebuffi, G E; Alberio, R H

    2010-06-01

    Two experiments were conducted to determine the effect of estradiol benzoate (EB) and intravaginal progestagen treatment on ovarian follicular dynamics and superstimulatory response in eCG-treated llamas. The purpose of Experiment 1 was to evaluate the effect of EB and progestagen treatment starting at different phases of dominant follicle (DF1) development on regression pattern and subsequent follicle wave emergence (WE2) in lactating and non-lactating llamas. Early lactating (n=24, 30+/-4 days postpartum) and non-lactating (n=24) females were assigned in equal numbers (n=8) to one of three groups according to the phase of DF1 (growing, static or regressing) determined by ultrasonography from day -3 to day 0. At day 0, llamas received an intravaginal sponge (MPA, 150 mg) and 5mg of MPA (i.m.). Half of the females (n=4) of each group were injected with 2mg (i.m.) of EB and half were not (control group). A 2 x 2 x 3 (lactational status, EB treatment and follicular phases) factorial design was used. Each sponge was removed 8 days later. Ovaries were monitored from day 0 to day 12. Daily blood samples were taken to determine 17beta-estradiol (E(2)) profiles from day 0 to day 8. The DF1 regression pattern was not affected (P>0.05) by the phase of follicle wave at the start of the treatment or any interactions among main effects. Follicle wave emergence in EB-treated llamas was delayed (P<0.05) by 2.3 days compared with non-treated llamas. Following EB treatment, plasma concentrations of E(2) were greater (P<0.05) from day 1 to day 5 in the treated than in non-treated females, but not from day 6 onward (P>0.05). Experiment 2 was designed to evaluate the effect of this treatment on the ovarian superovulatory response and embryo yield following eCG treatment administered on day of follicular wave emergence as determined in the Experiment 1. The same lactating (n=18, 61+/-4 days postpartum) and non-lactating (n=18) llamas at random stages of follicle wave were treated as

  18. Do antiparasitic medicines used in aquaculture pose a risk to the Norwegian aquatic environment?

    PubMed

    Langford, Katherine H; Øxnevad, Sigurd; Schøyen, Merete; Thomas, Kevin V

    2014-07-15

    Aquaculture production is an important industry in many countries and there has been a growth in the use of medicines to ensure the health and cost effectiveness of the industry. This study focused on the inputs of sea lice medication to the marine environment. Diflubenzuron, teflubenzuron, emamectin benzoate, cypermethrin, and deltamethrin were measured in water, sediment, and biota samples in the vicinity of five aquaculture locations along the Norwegian coast. Deltamethrin and cypermethrin were not detected above the limits of detection in any samples. Diflubenzuron, teflubenzuron, and emamectin benzoate were detected, and the data was compared the UK Environmental Quality Standards. The concentrations of emamectin benzoate detected in sediments exceed the environmental quality standard (EQS) on 5 occasions in this study. The EQS for teflubenzuron in sediment was exceeded in 67% of the samples and exceeded for diflubenzuron in 40% of the water samples collected. A crude assessment of the concentrations detected in the shrimp collected from one location and the levels at which chronic effects are seen in shrimp would suggest that there is a potential risk to shrimp. It would also be reasonable to extrapolate this to any species that undergoes moulting during its life cycle.

  19. Efficacy of two systemic insecticides injected into loblolly pine for protection against southern pine bark beetles (Coleoptera: Curculionidae).

    PubMed

    Grosman, Donald M; Clarke, Stephen R; Upton, William W

    2009-06-01

    We evaluated the efficacy of systemic insecticides emamectin benzoate and fipronil for preventing mortality of individual loblolly pines, Pinus taeda L., as a result of attacks by southern pine bark beetles (Coleoptera: Curculionidae, Scolytinae) for two consecutive years in Mississippi (2005-2006) and Alabama (2006-2007). Trees were injected once in the spring of 2005 (Mississippi) or 2006 (Alabama) and then were baited with species-specific bark beetle lures several weeks later. The southern pine beetle, Dendroctonus frontalis Zimmermann, was the target species but was changed to Ips spp. in Mississippi (but not Alabama) the second year because of few southern pine beetle attacks on baited trees. Single injections of emamectin benzoate were effective in reducing tree mortality caused by bark beetles compared with untreated checks. Although less effective overall, fipronil also significantly reduced tree mortality from southern pine beetle compared with the checks during the second year in Alabama. Tree mortality continued well after the lures had been removed. Evaluations of bolts taken from experimental trees killed in 2006 indicated that emamectin benzoate effectively prevented parent bark beetle gallery construction and that fipronil significantly reduced lengths of galleries constructed by adult beetles, brood development, and emergence, compared with checks. In contrast, neither insecticide treatment prevented the bark beetles from inoculating blue stain fungi, Ophiostoma spp., into treated trees.

  20. Crystal structure of {[2-hy­droxy-2-(3-meth­oxy­phen­yl)cyclo­hex­yl]meth­yl}di­methyl­ammonium benzoate

    PubMed Central

    Sheshadri, S. N.; Nagendra, P.; Siddaraju, B. P.; Hemakumar, K. H.; Byrappa, K.; Lokanath, N. K.; Madan Kumar, S.

    2015-01-01

    The title compound, C16H26NO2 +·C7H5O2 −, is a benzoate salt of the painkiller Tramadol. The six-membered cyclo­hexane ring of the cation adopts a slightly distorted chair conformation and carries OH and 3-meth­oxy­phenyl substituents at the 2-position and a protonated methyl­aza­niumylmethyl group at the 3-position. In addition, a weak intra­molecular C—H⋯O hydrogen bond is observed in the cation. In the crystal, weak O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds link the components into chains along [010]. A C—H⋯π contact is also observed. PMID:26594567

  1. Crystal structure of ethyl 4-[(E)-(4-hy­droxy-3-meth­oxy­benzyl­idene)amino]­benzoate: a p-hy­droxy Schiff base

    PubMed Central

    Ling, Jing; Kavuru, Padmini; Wojtas, Lukasz; Chadwick, Keith

    2016-01-01

    The title p-hy­droxy Schiff base, C17H17NO4, was synthesized via the condensation reaction of benzocaine with vanillin. The benzyl­idine and benzoate rings are inclined to one another by 24.58 (8)°, and the conformation about the C=N bond is E. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming zigzag chains propagating along [010]. Adjacent chains are linked by C—H⋯π and weak offset π–π inter­actions [inter­centroid distance = 3.819 (1) Å], forming sheets parallel to (10-2). PMID:27555938

  2. Crystal structure of μ-4-oxidobenzoato-κ(2)O(1):O(4)-bis-[bis-(1,10-phenanthroline-κ(2)N,N')copper(II)] bis-(4-hy-droxy-benzoate) 7.5-hydrate.

    PubMed

    Su, Jian-Rong; Li, Yu

    2016-10-01

    The title hydrated complex, [Cu2(C7H4O3)(C12H8N2)4](C7H5O3)2·7.5H2O, is composed of dinuclear Cu(II) complex cations, noncoordinating 4-hy-droxy-benzoate anions and water mol-ecules of crystallization. In the dinuclear complex cation, the Cu(II) ions are bridged by a 4-oxidobenzoate ligand and thus each metal ion is five-coordinated by two chelating 1,10-phenanthroline (phen) mol-ecules and one anionic O atom in a distorted trigonal-bipyramid geometry. In the crystal, aromatic π-π stacking occurs between phen rings of neighbouring dinuclear Cu(II) complex cations, forming two-dimensional supra-molecular systems parallel to (100).

  3. (/sup 3/H)Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs

    SciTech Connect

    McNeal, E.T.; Lewandowski, G.A.; Daly, J.W.; Creveling, C.R.

    1985-03-01

    (/sup 3/H)Batrachotoxinin A benzoate ((/sup 3/H)BTX-B) binds with high affinity to sites on voltage-dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex. In this preparation, local anesthetics competitively antagonize the binding of (/sup 3/H)BTX-B. The potencies of some 40 classical local anesthetics and a variety of catecholamine, histamine, serotonin, adenosine, GABA, glycine, acetylcholine, and calcium antagonists, tranquilizers, antidepressants, barbiturates, anticonvulsants, steroids, vasodilators, antiinflammatories, anticoagulants, analgesics, and other agents have been determined. An excellent correlation with the known local anesthetic activity of many of these agents indicate that antagonism of binding of (/sup 3/H)BTX-B binding provides a rapid, quantitative, and facile method for the screening and investigation of local anesthetic activity.

  4. Dietary exposure to benzoates (E210-E213), parabens (E214-E219), nitrites (E249-E250), nitrates (E251-E252), BHA (E320), BHT (E321) and aspartame (E951) in children less than 3 years old in France.

    PubMed

    Mancini, F R; Paul, D; Gauvreau, J; Volatier, J L; Vin, K; Hulin, M

    2015-01-01

    This study aimed to estimate the exposure to seven additives (benzoates, parabens, nitrites, nitrates, BHA, BHT and aspartame) in children aged less than 3 years old in France. A conservative approach, combining individual consumption data with maximum permitted levels, was carried out for all the additives. More refined estimates using occurrence data obtained from products' labels (collected by the French Observatory of Food Quality) were conducted for those additives that exceeded the acceptable daily intake (ADI). Information on additives' occurrence was obtained from the food labels. When the ADI was still exceeded, the exposure estimate was further refined using measured concentration data, if available. When using the maximum permitted level (MPL), the ADI was exceeded for benzoates (1.94 mg kg(-1) bw day(-1)), nitrites (0.09 mg kg(-1) bw day(-1)) and BHA (0.39 mg kg(-1) bw day(-1)) in 25%, 54% and 20% of the entire study population respectively. The main food contributors identified with this approach were current foods as these additives are not authorised in specific infant food: vegetable soups and broths for both benzoates and BHA, delicatessen and meat for nitrites. The exposure estimate was significantly reduced when using occurrence data, but in the upper-bound scenario the ADI was still exceeded significantly by the age group 13-36 months for benzoates (2%) and BHA (1%), and by the age group 7-12 months (16%) and 13-36 months (58%) for nitrites. Measured concentration data were available exclusively for nitrites and the results obtained using these data showed that the nitrites' intake was below the ADI for all the population considered in this study. These results suggest that refinement of exposure, based on the assessment of food levels, is needed to estimate the exposure of children to BHA and benzoates for which the risk of exceeding the ADI cannot be excluded when using occurrence data.

  5. A redetermination from the original data of the crystal structure of 2-amino-4,6-di­meth­oxy­pyrimidin-1-ium 4-amino­benzoate

    PubMed Central

    Fábry, Jan

    2016-01-01

    The title structure, C6H9.5N3O2 0.5+·C7H6.5NO2 0.5−, which might be named schematically as 2-amino-4,6-di­meth­oxy­pyrimidine-(μ2-hydrogen)-4-amino­benzoate to indicate a bridging H atom, has been redetermined from the data published by Thanigaimani, Mu­thiah & Lynch [Acta Cryst. (2006), E62, o2976–o2978]. The improvement of the present redetermination consists in a released geometry of the primary amine groups, which were originally assumed to be planar, as well as in a redetermination of the position of the hy­droxy H atom. This H atom, whose parameters were originally constrained, turns out to be situated about the centre of the O⋯N hydrogen bond in two disordered positions with occupancies of 0.5 each. PMID:27375878

  6. A redetermination of 2-(6-diethyl-amino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate-ethyl gallate (1/1) at room temperature.

    PubMed

    Mizuguchi, Jin; Sato, Kazuyuki

    2009-03-06

    The title compound, C(28)H(30)N(2)O(3)·C(9)H(10)O(5), is a well known red leuco complex of 2-(6-diethyl-amino-3-diethyl-iminio-3H-xanthene-9-yl)benzoate (rhodamine B base abbreviated to RBB: leuco dye) with ethyl gallate (EG: developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [(2007) Chem. Lett. 36, 1010-1011]. The RBB-EG complex forms a dimer (RBB⋯EG⋯EG⋯RBB) through inter-molecular O-H⋯O hydrogen bonds. In a subsequent re-examination of the structure at room temperature, we found the RBB mol-ecule to be disordered with a methyl group of one ethyl substituent of a diethyl-amino group at one extremity of the xanthene unit disordered over two positions [occupancies: 0.735 (5)/0.265 (5)]. Furthermore, at the other end of the xanthene residue, the entire diethyl-amino substituent (i.e. the N atom and the associated C and H atoms) was also disordered over two sites with occupancies 0.653 (7)/0.347 (7). This leads to four kinds of RBB conformations, which, in turn, results in the formation of 16 discrete RBB⋯EG⋯EG⋯RBB dimers in the crystal.

  7. Crystal structure of bis­(tri­ethano­lamine-κ3 N,O,O′)nickel(II) bis­(3-hy­droxy­benzoate) tetra­hydrate

    PubMed Central

    Ibragimov, Aziz B.

    2016-01-01

    The reaction of 3-hy­droxy­benzoic (m-hy­droxy­benzoic) acid (MHBA), tri­ethano­lamine (TEA) and Ni(NO3)2 in aqueous solution led to formation of the hydrated title salt, [Ni(C6H15NO3)2](C7H5O3)·4H2O. In the complex cation, the Ni2+ ion is located on an inversion centre. Two symmetry-related TEA ligands occupy all coordination sites in an N,O,O′-tridentate coordination, leading to a slightly distorted NiN2O4 octa­hedron. Two ethanol groups of each TEA ligand form two five-membered chelate rings around Ni2+, while the third ethanol group does not coordinate to the metal atom. Two MHBA− anions in the benzoate form are situated in the outer coordination sphere for charge compensation. An intricate network of hydrogen bonds between the free and coordinating hy­droxy groups of the TEA ligands, the O atoms of the MHBA− anions and the water mol­ecules leads to the formation of a two-dimensional structure extending parallel to (010). PMID:27308009

  8. Preparation and physicochemical characterization of a solid dispersion of (3, 5, 6-trimethylpyrazin-2-yl) methyl 3-methoxy-4-[(3, 5, 6-trimethylpyrazin-2-yl) methoxy] benzoate (VA-T) and polyvinylpyrrolidone.

    PubMed

    Cao, Sa-Li; Hou, Peng; Li, Bin; Fu, Jing; Yin, Xing-Bin; Dang, Xiao-Fang; Yang, Chun-Jing; Zhang, Jin; Zhang, Hui; Lei, Hai-Min; Ni, Jian

    2015-11-01

    Ischemic brain injury is a major disease which threatens human health and safety. (3, 5, 6-trimethylpyrazin-2-yl) methyl 3-methoxy-4-[(3, 5, 6-trimethylpyrazin-2-yl) methoxy] benzoate (VA-T), a newly discovered lead compound, is effective for the treatment of ischemic brain injury and its sequelae. But the poor solubility of VA-T leads to poor dissolution and limited clinical application. In order to improve the dissolution of VA-T, the pharmaceutical technology of solid dispersions was used in the present study. VA-T/polyvinylpyrrolidone (PVP) solid dispersion was prepared by the solvent method. The dissolution studies were carried out and solid state characterization was evaluated by differential scanning calorimetry (DSC), infrared spectroscopy (IR), x-ray diffraction (XRD) and scanning electron microscopy (SEM). The dissolution rate of VA-T was significantly improved by solid dispersion compared to that of the pure drug and physical mixture. The results of DSC and XRD indicated that the VA-T solid dispersion was amorphous. The IR spectra showed the possible interaction between VA-T and PVP was the formulation of hydrogen bonding. The SEM analysis demonstrated that there was no VA-T crystal observed in the solid dispersions. The ideal drug-to-PVP ratio was 1:5. In conclusion, the solid dispersion technique can be successfully used for the improvement of the dissolution profile of VA-T.

  9. Biphenyl alkyloxy benzoates ferroelectric liquid crystals : structural, thermodynamic and dielectric studies of the octyl and the decyl homologous ; electroclinic effect in the N^* phase near a N^*-SA-SC^* multicritical point

    NASA Astrophysics Data System (ADS)

    Legrand, C.; Isaert, N.; Hmine, J.; Buisine, J. M.; Parneix, J. P.; Nguyen, H. T.; Destrade, C.

    1992-08-01

    A new biphenyl alkyloxy benzoate series is synthesized. Thermodynamic, structural and dielectric measurements have been performed on the two homologous n=8 and n=10. For these two compounds, the sequences N^*-SC^* or N^*-SA-SC^* are respectively observed under atmospheric pressure. Pressure-Temperature phase diagrams show that these phase transitions appear near a N^*-SA-SC^* multicritical point : for n=8, the SA phase is induced under moderate pressure ; for n=10, the SA temperature range is less than 1 °C at atmospheric pressure and slightly increases under pressure. The dielectric charcterization detects a relaxation process in the N^* phase near the N^*-SC^* or the N^*-SA phase transitions whose temperature dependence of the characteristic parameters are similar to these of the classical soft mode observed near the SA-SC^* phase transition. This relaxation process is attributed to an electroclinic effect in the N^* phase near the N^*-SC^* or the N^*-SA phase transitions. This is the first dielectric observation of such an effect, furthermore it is observed it is observed in pure compounds and it is of large amplitude. This is probably connected with hte high polarization, the local smectic order and the proximity of a N^*-SA-SC^* multicritical point. Une nouvelle série de biphényles benzoates a été synthétisée. Des mesures thermodynamiques, structurales et diélectriques ont été entreprises pour les homologues n=8 et n=10. Pour ces deux composés, les deux séquences N^*-SC^* et N^*-SA-SC^* sont respectivement observées sous pression atmosphérique. Les diagrammes de phase Pression-Température montrent que ces transitions de phases apparaissent près d'un point multicritique : pour n=8, la phase SA est induite sous une pression modérée ; pour n=10, le domaine d'existence de la phase SA inférieur à 1 °C à pression atmosphérique s'accroît légèrement avec la pression. La caractérisation diélectrique met en évidence un mécanisme de

  10. A low-temperature phase of the 1:1 complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate with ethyl gallate at 93 K.

    PubMed

    Mizuguchi, Jin

    2008-06-07

    The title compound, C(28)H(30)N(2)O(3)·C(9)H(10)O(5), is a well known red leuco complex of 2-(6-diethylamino-3-diethyl-iminio-3H-xanthen-9-yl)benzoate (rhodamine B base abbreviated to RBB, a leuco dye) with ethyl gallate (EG, developer). The structure of the complex at room temperature has recently been reported by Sekiguchi, Takayama, Gotanda & Sano [Chem. Lett. (2007 ▶), 36, 1010-1011]. We have found a new phase of the material with two discrete base/developer complexes (RBB-A/EG-A and RBB-B/EG-B) in the asymmetric unit at 93 K. There are no significant differences between the two developer mol-ecules EG-A and EG-B. The lactone ring of RBB is opened in each mol-ecule to form a zwitterionic structure. However, the xanthene system is almost flat in RBB-A (r.m.s. deviation 0.0234 Å) but is less so in RBB-B (r.m.s. deviation 0.1095 Å). Furthermore, the ethyl groups of the xanthene diethyl-amino substituents lie on the same side of the xanthene plane in RBB-A but on opposite sides in RBB-B. Dimeric dye/developer complexes are formed through inter- and intra-molecular O-H⋯O hydrogen bonds and are linked further into dimers by additional O-H⋯O hydrogen bonds involving either EG-A or EG-B developer mol-ecules.

  11. Engineering crystals that facilitate the acyl-transfer reaction: insight from a comparison of the crystal structures of myo-inositol-1,3,5-orthoformate-derived benzoates and carbonates.

    PubMed

    Tamboli, Majid I; Krishanaswamy, Shobhana; Gonnade, Rajesh G; Shashidhar, Mysore S

    2016-11-01

    Minor variations in the molecular structure of constituent molecules of reactive crystals often yield crystals with significantly different properties due to altered modes of molecular association in the solid state. Hence, these studies could provide a better understanding of the complex chemical processes occurring in the crystalline state. However, reactions that proceed efficiently in molecular crystals are only a small fraction of the reactions that are known to proceed (with comparable efficiency) in the solution state. Hence, for consistent progress in this area of research, investigation of newer reactive molecular crystals which support different kinds of reactions and their related systems is essential. The crystal structures and acyl-transfer reactivity of a myo-inositol-1,3,5-orthoformate-derived dibenzoate and its carbonate (4-O-benzoyl-2-O-phenoxycarbonyl-myo-inositol 1,3,5-orthoformate, C21H18O9) and thiocarbonate (4-O-benzoyl-2-O-phenoxythiocarbonyl-myo-inositol 1,3,5-orthoformate, C21H18O8S) analogs are compared with the aim of understanding the relationship between crystal structure and acyl-transfer reactivity. Insertion of an O atom in the acyl (or thioacyl) group of an ester gives the corresponding carbonate (or thiocarbonate). This seemingly minor change in molecular structure results in a considerable change in the packing of the molecules in the crystals of myo-inositol-1,3,5-orthoformate-derived benzoates and the corresponding carbonates. These differences result in a lack of intermolecular acyl-transfer reactivity in crystals of myo-inositol-1,3,5-orthoformate-derived carbonates. Hence, this study illustrates the sensitivity of the relative orientation of molecules, their packing and ensuing changes in the reactivity of resulting crystals to minor changes in molecular structure.

  12. Quality by Design-Based Development of a Stability-Indicating RP-HPLC Method for the Simultaneous Determination of Methylparaben, Propylparaben, Diethylamino Hydroxybenzoyl Hexyl Benzoate, and Octinoxate in Topical Pharmaceutical Formulation

    PubMed Central

    Roy, Chinmoy; Chakrabarty, Jitamanyu

    2014-01-01

    Abstract A stability-indicating RP-HPLC method has been developed and validated for the simultaneous determination of methylparaben (MP), propylparaben (PP), diethylamino hydroxybenzoyl hexyl benzoate (DAHHB), and octinoxate (OCT) in topical pharmaceutical formulation. The desired chromatographic separation was achieved on the KinetexTM C18 (250 × 4.6 mm, 5 μm) column using gradient elution at 257 nm detection wavelength. The optimized mobile phase consisted of a buffer : acetonitrile : tetrahydrofuran (60 : 30 : 10, v/v/v) as solvent A and acetonitrile : tetrahydrofuran (70 : 30, v/v) as solvent B. The method showed linearity over the range of 0.19–148.4 μg/mL, 0.23–15.3 μg/mL, 1.97–600.5 μg/mL, and 1.85–451.5 μg/mL for MP, PP, DAHHB, and OCT, respectively. Recovery for all the components was found to be in the range of 98–102%. The stability-indicating capability of the developed method was established by analysing the forced degradation samples in which the spectral purity of MP, PP, DAHHB, and OCT, along with the separation of the degradation products from the analyte peaks, was achieved. The proposed method was successfully applied for the quantitative determination of MP, PP, DAHHB, and OCT in the lotion sample. The design expert with ANOVA software with the linear model was applied and a 24 full factorial design was employed to estimate the model coefficients and also to check the robustness of the method. Results of the two-level full factorial design, 24 with 20 runs including four centrepoint analysis based on the variance analysis (ANOVA), demonstrated that all four factors, as well as the interactions of resolution between DAHHB and OCT are statistically significant. PMID:25853065

  13. Final report of the safety assessment of Alcohol Denat., including SD Alcohol 3-A, SD Alcohol 30, SD Alcohol 39, SD Alcohol 39-B, SD Alcohol 39-C, SD Alcohol 40, SD Alcohol 40-B, and SD Alcohol 40-C, and the denaturants, Quassin, Brucine Sulfate/Brucine, and Denatonium Benzoate.

    PubMed

    2008-01-01

    Alcohol Denat. is the generic term used by the cosmetics industry to describe denatured alcohol. Alcohol Denat. and various specially denatured (SD) alcohols are used as cosmetic ingredients in a wide variety of products. Many denaturants have been previously considered, on an individual basis, as cosmetic ingredients by the Cosmetic Ingredient Review (CIR) Expert Panel, whereas others, including Brucine and Brucine Sulfate, Denatonium Benzoate, and Quassin, have not previously been evaluated. Quassin is a bitter alkaloid obtained from the wood of Quassia amara. Quassin has been used as an insect antifeedant and insecticide and several studies demonstrate its effectiveness. At oral doses up to 1000 mg/kg using rats, Quassin was not toxic in acute and short-term tests, but some reversible piloerection, decrease in motor activity, and a partial loss of righting reflex were found in mice at 500 mg/kg. At 1000 mg/kg given intraperitoneally (i.p.), all mice died within 24 h of receiving treatment. In a cytotoxicity test with brine shrimp, 1 mg/ml of Quassin did not possess any cytotoxic or antiplasmodial activity. Quassin administered to rat Leydig cells in vitro at concentrations of 5-25 ng/ml inhibited both the basal and luteinizing hormone (LH)-stimulated testosterone secretion in a dose-related fashion. Quassin at doses up to 2.0 g/kg in drinking water using rats produced no significant effect on the body weights, but the mean weights of the testes, seminal vesicles, and epididymides were significantly reduced, and the weights of the anterior pituitary glands were significantly increased. The sperm counts and levels of LH, follicle-stimulating hormone (FSH), and testosterone were significantly lower in groups treated with Quassin. Brucine is a derivative of 2-hydroxystrychnine. Swiss-Webster mice given Brucine base, 30 ml/kg, had an acute oral LD(50) of 150 mg/kg, with central nervous system depression followed by convulsions and seizures in some cases. In those

  14. Hydrogen-bonding synthons in lamotrigine salts: 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 2-[(2-carboxyphenyl)disulfanyl]benzoate in its monohydrate and anhydrous forms.

    PubMed

    Freire, Eleonora; Polla, Griselda; Baggio, Ricardo

    2016-11-01

    Lamotrigine is a drug used in the treatment of epilepsy and related convulsive diseases. The drug in its free form is rather inadequate for pharmacological use due to poor absorption by the patient, which limits its bioavailability. On the other hand, the lamotrigine molecule is an excellent hydrogen-bonding agent and this has been exploited intensively in the search for better formulations. The formulation presently commercialized (under the brand name Lamictal) is rather complex and includes a number of anions in addition to the active pharmaceutical ingredient (API). The title salts of lamotrigine, namely 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 2-[(2-carboxyphenyl)disulfanyl]benzoate monohydrate, C9H8Cl2N5(+)·C14H9O4S2(-)·H2O, (I), and the anhydrate, C9H8Cl2N5(+)·C14H9O4S2(-), (II), contain a lamotriginium cation (L), a hydrogen dithiodibenzoate monoanion (D) and, in the case of (I), a disordered solvent water molecule. Both L and D present their usual configurations severely twisted around their central C-C and S-S bonds, respectively. The supramolecular structure generated by the many available donor and acceptor sites is characterized by a planar antisymmetric motif of the form D-L-L-D, i.e. the structural building block. Although this characteristic motif is extremely similar in both structures, its conformation involves different donors and acceptors in its R2(2)(8) central L-L homosynthon. The lateral R2(2)(8) D-L heterosynthons are, on the other hand, identical. These substructures are further connected by strong hydrogen bonds into broad two-dimensional structures, in turn weakly linked to each other. Even if the homo- and heterosynthons in (I) and (II) are rather frequent in lamotrigine structural chemistry, the composite tetrameric synthon appears to be much less common. The occurrence of these motifs among lamotrigine salts and cocrystals is analyzed.

  15. Crystal structures of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13RS,14SR)-13-hy-droxy-7-meth-oxy-meth-oxy-11,15,18,18-tetra-methyl-3-oxo-2,4-dioxa-tetra-cyclo-[12.3.1.0(1,5).0(6,11)]octa-dec-15-en-10-yl benzoate, its 13-epimer and 13-one derivative.

    PubMed

    Oishi, Takeshi; Fukaya, Keisuke; Yamaguchi, Yu; Sugai, Tomoya; Watanabe, Ami; Sato, Takaaki; Chida, Noritaka

    2015-05-01

    The title compounds, C29H38O8·0.25C5H12, (A), C29H38O8, (B), and C29H36O8, (C), are tetra-cyclic benzoates possessing a taxane skeleton with a fused dioxolane ring as the core structure. In the asymmetric unit of (A), there are two independent benzoate mol-ecules (A and A') and a half mol-ecule of solvent pentane disordered about an inversion center. The mol-ecular conformations of (A), (B) and (C) are similar except for the flexible meth-oxy-meth-oxy group. The cyclo-hexane, cyclo-hexene and central cyclo-octane rings adopt chair, half-chair and chair-chair (extended crown) forms, respectively. The dioxolane rings are essentially planar, while the dioxolane ring of A' is slightly twisted from the mean plane. In the crystal of (A), inter-molecular O-H⋯O, C-H⋯O and C-H⋯π inter-actions link the independent benzoates alternately, forming a chain structure. In the crystals of (B) and (C), mol-ecules are linked through O-H⋯O and C-H⋯π inter-actions, and C-H⋯O hydrogen bonds, respectively, into similar chains. Further, weak inter-molecular C-H⋯O inter-actions connect the chains into a three-dimensional network in (A) and a sheet in (B), whereas no other interactions are observed for (C).

  16. Toxicity and bioefficacy of individual and combination of diversified insecticides against jute hairy caterpillar, Spilarctia obliqua.

    PubMed

    Selvaraj, K; Ramesh, V; Gotyal, B S; Satpathy, S

    2015-11-01

    Toxicity of conventional (profenofos 50 EC and λ-cyhalothrin 5 EC) and non-conventional (flubendiamide 480 SC, chlorantraniliprole 18.5 SC, emamectin benzoate 5 SG) insecticides was determined on the basis of median lethal concentration (LC50) values on third instar larvae of jute hairy caterpillar, Spilarctia obliqua under laboratory conditions. Further, the promising binary insecticides combinations with lesser LC50 values and adequate synergistic activity were evaluated under field conditions. The LC50 values calculated for insecticides viz., chlorantraniliprole, flubendiamide emamectin benzoate, λ-cyhalothrin and profenophos were 0.212, 0.232, 0.511, 0.985 and 3.263 ppm, respectively. Likewise, the LC50 values for flubendiamide with λ-cyhalothrin in 3:1 proportion was most toxic (0.103 ppm) amongst all the other binary combinations with λ-cyhalothrin. Chlorantraniliprole in combination with λ-cyhalothrin at 1:1 proportion (0.209 ppm) was most toxic followed by 3:1 proportion (0.345 ppm). Similarly, emamectin benzoate in combination with λ-cyhalothrin at 1:1 proportion was more toxic (0.271 ppm) than 3:1 ratio (0.333 ppm). Toxicity index of flubendiamide + λ-cyhalothrin (3:1 ratio) was highest (970.87). Bioefficacy of synergistic binary combinations along with individual insecticides established the superiority of profenophos + λ-cyhalothrin (3:1) with 89.12% reduction in infestation and recorded maximum fibre yield 38.67qha' under field condition. Moreover, combination of diverse insecticides group might sustain toxicity against the target insect for longer period with least probability of resistance development.

  17. Current status of insecticide resistance in Helicoverpa armigera after 15 years of Bt cotton planting in China.

    PubMed

    Yang, Yihua; Li, Yapeng; Wu, Yidong

    2013-02-01

    Insecticide resistance was an important factor responsible for outbreaks of Helicoverpa armigera (Hübner) in China in the early 1990s. Bt cotton has been adopted in China since 1997, and has resulted in a reduction of insecticide use for H. armigera control. After 15 yr of Bt cotton planting, in 2011 we surveyed resistance to fenvalerate, phoxim, and emamectin benzoate in 16 field populations of H. armigera collected from major cotton production areas of China. Fourteen populations from northern China showed very strong resistance to fenvalerate (from 43- to 830-fold) and low levels of resistance to phoxim (3.0- to 8.9-fold) when compared with the susceptible SCD strain of H. armigera, whereas two populations from northwestern China showed low levels of resistance to fenvalerate (3.0- and 10-fold) and no resistance to phoxim (0.7- and 0.9-fold). Synergist bioassays demonstrated that oxidase-based detoxification was involved in fenvalerate resistance and esterase-based detoxification in phoxim resistance in the resistant field populations. In comparison with the resistance in field populations before Bt cotton adoption, we observed a maintenance of high levels of fenvalerate resistance, but a reversion of phoxim resistance from high levels to low levels in the field populations of H. armigera from northern China. All 16 field populations from both northern China and northwestern China were susceptible to emamectin benzoate (with about two-fold variations in LD50s among populations), but the SCD strain has an inherent tolerance of 11-fold compared with the most susceptible field population (Xiajin-1). Emamectin benzoate is not cross resistant to fenvalerate and may provide an alternative option for H. armigera control in China, if the efficacy of Bt cotton is compromised by Bt resistance in the field.

  18. Sorbate and benzoate in Turkish retail foodstuffs.

    PubMed

    Ulca, Pelin; Atamer, Beril; Keskin, Mehtap; Senyuva, Hamide Z

    2013-01-01

    From 2008 to 2011, surveys were conducted to determine the levels of benzoic and sorbic acids and their respective salts in 983 retail food samples which included sauces, vegetable and fruit preparations, flavoured syrups, food supplements, cereals, bakery products, jelly, synthetic cream, sprays, mustards, jam and preserves, molasses, chewing gum, confectionery, non-alcoholic beverages, tea, wine, vinegar, brine and beers. The analysis involved methanol extraction of the foodstuff and direct determination by HPLC with UV detection. Quality assurance was employed with each batch of samples. Accuracy was ensured through regular participation in proficiency tests. Over this four-year period, a total of 23 samples (2.3%), some syrups, tomato sauces and fruit contained individual or combined levels of sorbic and benzoic acids above regulatory limits. Unauthorised use of benzoic acid was also detected in a syrup sample, bakery products and fruit preserves.

  19. Follicle stimulating hormone secretion and dominant follicle growth during treatment of Bos indicus heifers with intra-vaginal progesterone releasing devices, oestradiol benzoate, equine chorionic gonadotrophin and prostaglandin F(2α).

    PubMed

    Edwards, S A A; Phillips, N J; Boe-Hansen, G B; Bo, G A; Burns, B M; Dawson, K; McGowan, M R

    2013-03-01

    The aim of this study was to investigate the effects on follicle stimulating hormone (FSH) secretion and dominant follicle (DF) growth, of treatment of Bos indicus heifers with different combinations of intra-vaginal progesterone releasing devices (IPRD), oestradiol benzoate (ODB), PGF2α and eCG. Two-year-old Brahman (BN; n=30) and Brahman-cross (BNX; n=34) heifers were randomly allocated to three IPRD-treatments: (i) standard-dose IPRD [CM 1.56g; 1.56g progesterone (P4); n=17]; (ii) half-dose IPRD (CM 0.78g; 0.78g P4; n=15); (iii) half-dose IPRD+300IU eCG at IPRD removal (CM 0.78g+G; n=14); and, (iv) non-IPRD control (2×PGF2α; n=18) 500μg cloprostenol on Days -16 and -2. IPRD-treated heifers received 250μg PGF2α at IPRD insertion (Day -10) and IPRD removal (Day -2) and 1mg ODB on Day -10 and Day -1. Follicular dynamics were monitored daily by trans-rectal ultrasonography from Day -10 to Day 1. Blood samples for determination of P4 were collected daily and samples for FSH determination were collected at 12h intervals from Day -9 to Day -2. A significant surge in concentrations of FSH was observed in the 2×PGF2α treatment 12h prior and 48h after follicular wave emergence, but not in the IPRD-treated heifers. Estimated mean concentrations of total plasma P4 during the 8 days of IPRD insertion was greater (P<0.001) in the CM 1.56g P4 treated heifers compared to the CM 0.78g P4 treated heifers (18.38ng/ml compared with 11.09ng/ml, respectively). A treatment by genotype interaction (P=0.036) was observed in the mean plasma P4 concentration in heifers with no CL during IPRD insertion, whereby BN heifers in the CM 1.56g treatment had greater plasma P4 than the BNX heifers on Days-9, -7, -6, -5, and -4. However, there was no genotype effect in the CM 0.78g±G or the 2×PGF2α treatment. Treatment had no effect on the DF growth from either day of wave emergence (P=0.378) or day of IPRD removal (P=0.780) to ovulation. This study demonstrates that FSH secretion in B

  20. Determination of avermectins: a QuEChERS approach to the analysis of food samples.

    PubMed

    Rúbies, A; Antkowiak, S; Granados, M; Companyó, R; Centrich, F

    2015-08-15

    We present a simple method for extracting avermectines from meat, based on a QuEChERS approach followed by liquid chromatography (LC) coupled to triple quadrupole (QqQ) tandem mass spectrometry (MS/MS). The compounds considered are ivermectin, abamectin, emamectin, eprinomectin, doramectin and moxidectin. The new method has been fully validated according to the requirements of European Decision 657/2002/CE (EU, 2002). The method is suitable for the analysis of avermectins at concentration as low as 2.5 μg kg(-1), and allows high sample throughput. In addition, the detection of avermectins by high resolution mass spectrometry using a quadrupole-Orbritrap (Q-Orbitrap) hybrid instrument has been explored, and the target Selected Ion Monitoring data dependent MS/MS (t-SIM-dd MS/MS) mode has been found to provide excellent performance for residue determination of target analytes.

  1. Crystal structure of hexa-prop-2-en-1-yl 4,4',4'',4''',4'''',4'''''-[1,3,5,2λ(5),4λ(5),6λ(5)-tri-aza-triphosphinine-2,2,4,4,6,6-hexa-yl-hexa-kis-(-oxy)]hexa-benzoate.

    PubMed

    Zhu, Jing; Li, Qian; Zheng, Fu-Wei; He, Juan; Qu, Ling-Bo

    2015-12-01

    In the title compound, C60H54N3O18P3, the central phosphazene ring is essentially planar, with an r.m.s. deviation of the six fitted atoms of 0.068 Å. The P-N bond lengths are within the narrow range 1.575 (2)-1.585 (2) Å, indicating the electrons are delocalized within the ring. The two ethenyl benzoate substituents on each P atom are located up and down with respect to the plane of the central P3N3 ring. The atoms of two terminal propenyl groups are disordered over two sets of sites, with refined site-occupancy ratios of 0.249 (12):0.751 (12) and 0.476 (9):0.524 (9). No intermolecular interactions are observed.

  2. Crystal structure of μ-4-oxidobenzoato-κ2 O 1:O 4-bis­[bis­(1,10-phenanthroline-κ2 N,N′)copper(II)] bis­(4-hy­droxy­benzoate) 7.5-hydrate

    PubMed Central

    Su, Jian-Rong; Li, Yu

    2016-01-01

    The title hydrated complex, [Cu2(C7H4O3)(C12H8N2)4](C7H5O3)2·7.5H2O, is composed of dinuclear CuII complex cations, noncoordinating 4-hy­droxy­benzoate anions and water mol­ecules of crystallization. In the dinuclear complex cation, the CuII ions are bridged by a 4-oxidobenzoate ligand and thus each metal ion is five-coordinated by two chelating 1,10-phenanthroline (phen) mol­ecules and one anionic O atom in a distorted trigonal-bipyramid geometry. In the crystal, aromatic π–π stacking occurs between phen rings of neighbouring dinuclear CuII complex cations, forming two-dimensional supra­molecular systems parallel to (100). PMID:27746927

  3. A Review on the Toxicity and Non-Target Effects of Macrocyclic Lactones in Terrestrial and Aquatic Environments

    PubMed Central

    Lumaret, Jean-Pierre; Errouissi, Faiek; Floate, Kevin; Römbke, Jörg; Wardhaugh, Keith

    2012-01-01

    The avermectins, milbemycins and spinosyns are collectively referred to as macrocyclic lactones (MLs) which comprise several classes of chemicals derived from cultures of soil micro-organisms. These compounds are extensively and increasingly used in veterinary medicine and agriculture. Due to their potential effects on non-target organisms, large amounts of information on their impact in the environment has been compiled in recent years, mainly caused by legal requirements related to their marketing authorization or registration. The main objective of this paper is to critically review the present knowledge about the acute and chronic ecotoxicological effects of MLs on organisms, mainly invertebrates, in the terrestrial and aquatic environment. Detailed information is presented on the mode-of-action as well as the ecotoxicity of the most important compounds representing the three groups of MLs. This information, based on more than 360 references, is mainly provided in nine tables, presenting the effects of abamectin, ivermectin, eprinomectin, doramectin, emamectin, moxidectin, and spinosad on individual species of terrestrial and aquatic invertebrates as well as plants and algae. Since dung dwelling organisms are particularly important non-targets, as they are exposed via dung from treated animals over their whole life-cycle, the information on the effects of MLs on dung communities is compiled in an additional table. The results of this review clearly demonstrate that regarding environmental impacts many macrocyclic lactones are substances of high concern particularly with larval instars of invertebrates. Recent studies have also shown that susceptibility varies with life cycle stage and impacts can be mitigated by using MLs when these stages are not present. However information on the environmental impact of the MLs is scattered across a wide range of specialised scientific journals with research focusing mainly on ivermectin and to a lesser extent on abamectin

  4. Toxicity of nine insecticides on four natural enemies of Spodoptera exigua.

    PubMed

    Liu, Yongqiang; Li, Xiangying; Zhou, Chao; Liu, Feng; Mu, Wei

    2016-12-13

    Spodoptera exigua, which feeds on various crops worldwide, has natural enemies that are susceptible to the insecticides used against S. exigua. We investigate the toxicity and residue risk of 9 insecticides on the development of H. axyridis, C. sinica, S. manilae and T. remus. S. manilae and T. remus adults were sensitive to all 9 insecticides (LC50 less than 2.75 mg a.i. liter(-1)), while H. axyridis and C. sinica adults were less sensitive (LC50 between 6 × 10(-5) mg a.i. liter(-1) and 78.95 mg a.i. liter(-1)). Emamectin benzoate, spinosad, indoxacarb, alpha-cypermethrin, chlorfenapyr and chlorantraniliprole showed no toxicity on H. axyridis, C. sinica, S. manilae and T. remus pupae with the recommended field concentrations. The risk analysis indicated that chlorantraniliprole is harmless to larvae of four natural enemies and adult of H. axyridis, C. sinica and S. manilae. Emamectin benzoate and spinosad had higher safety to the development of H. axyridis, C. sinica, S. manilae and T. remus with the risk duration less than 4d. Indoxacarb, tebufenozide, chlorfenapyr, methomyl, alpha-cypermethrin and chlorpyrifos showed dangerously toxic and long risk duration on S. manilae and T. remus adults.

  5. Toxicity of nine insecticides on four natural enemies of Spodoptera exigua

    PubMed Central

    Liu, Yongqiang; Li, Xiangying; Zhou, Chao; Liu, Feng; Mu, Wei

    2016-01-01

    Spodoptera exigua, which feeds on various crops worldwide, has natural enemies that are susceptible to the insecticides used against S. exigua. We investigate the toxicity and residue risk of 9 insecticides on the development of H. axyridis, C. sinica, S. manilae and T. remus. S. manilae and T. remus adults were sensitive to all 9 insecticides (LC50 less than 2.75 mg a.i. liter−1), while H. axyridis and C. sinica adults were less sensitive (LC50 between 6 × 10−5 mg a.i. liter−1 and 78.95 mg a.i. liter−1). Emamectin benzoate, spinosad, indoxacarb, alpha-cypermethrin, chlorfenapyr and chlorantraniliprole showed no toxicity on H. axyridis, C. sinica, S. manilae and T. remus pupae with the recommended field concentrations. The risk analysis indicated that chlorantraniliprole is harmless to larvae of four natural enemies and adult of H. axyridis, C. sinica and S. manilae. Emamectin benzoate and spinosad had higher safety to the development of H. axyridis, C. sinica, S. manilae and T. remus with the risk duration less than 4d. Indoxacarb, tebufenozide, chlorfenapyr, methomyl, alpha-cypermethrin and chlorpyrifos showed dangerously toxic and long risk duration on S. manilae and T. remus adults. PMID:27958333

  6. Bursaphelenchus xylophilus is killed by homologues of 2-(1-undecyloxy)-1-ethanol

    NASA Astrophysics Data System (ADS)

    Kim, Junheon; Lee, Sang-Myeong; Park, Chung Gyoo

    2016-07-01

    2-(1-Undecyloxy)-1-ethanol, monochamol, is a male-produced aggregation pheromone of the Monochamus species, which are efficient vectors of the pine wood nematode (PWN), Bursaphelenchus xylophilus, which cause devastating damage to pines worldwide. The nematicidal activity of synthetic monochamol and its homologues (ROEtOH: R = C7-C13) were investigated to find potential alternatives to the currently used PWN control agents abamectin and emamectin. Compounds with C7-C13 chain length alkyl groups exhibited 100% nematicidal activity at a concentration of 1000 mg/L. At a concentration of 100 mg/L, 2-(1-nonyloxy)-1-ethanol (C9OEtOH), 2-(1-decyloxy)-1-ethanol (C10OEtOH), 2-(1-undecyloxy)-1-ethanol (C11OEtOH), and 2-(1-dodecyloxy)-1-ethanol (C12OEtOH) showed 100% nematicidal activity, but the others showed weaker activities. C11OEtOH showed similar nematicidal activity to abamectin in terms of LD90 values, which were 13.30 and 12.53 mg/L, respectively. However, C9OEtOH, C10OEtOH, and C12OEtOH (LC90 values: 53.63, 38.18, and 46.68 mg/L, respectively) were less effective than C11OEtOH and abamectin. These results indicate that monochamol could be an effective alternative agent against PWN. The relationship of insecticidal and nematicidal activity to different carbon chain lengths in compounds is discussed.

  7. Bursaphelenchus xylophilus is killed by homologues of 2-(1-undecyloxy)-1-ethanol

    PubMed Central

    Kim, Junheon; Lee, Sang-Myeong; Park, Chung Gyoo

    2016-01-01

    2-(1-Undecyloxy)-1-ethanol, monochamol, is a male-produced aggregation pheromone of the Monochamus species, which are efficient vectors of the pine wood nematode (PWN), Bursaphelenchus xylophilus, which cause devastating damage to pines worldwide. The nematicidal activity of synthetic monochamol and its homologues (ROEtOH: R = C7-C13) were investigated to find potential alternatives to the currently used PWN control agents abamectin and emamectin. Compounds with C7-C13 chain length alkyl groups exhibited 100% nematicidal activity at a concentration of 1000 mg/L. At a concentration of 100 mg/L, 2-(1-nonyloxy)-1-ethanol (C9OEtOH), 2-(1-decyloxy)-1-ethanol (C10OEtOH), 2-(1-undecyloxy)-1-ethanol (C11OEtOH), and 2-(1-dodecyloxy)-1-ethanol (C12OEtOH) showed 100% nematicidal activity, but the others showed weaker activities. C11OEtOH showed similar nematicidal activity to abamectin in terms of LD90 values, which were 13.30 and 12.53 mg/L, respectively. However, C9OEtOH, C10OEtOH, and C12OEtOH (LC90 values: 53.63, 38.18, and 46.68 mg/L, respectively) were less effective than C11OEtOH and abamectin. These results indicate that monochamol could be an effective alternative agent against PWN. The relationship of insecticidal and nematicidal activity to different carbon chain lengths in compounds is discussed. PMID:27403600

  8. Crystal structures of (E)-4-[1-(2-carbamo­thio­yl­hydrazinyl­idene)eth­yl]phenyl acetate and (E)-4-[1-(2-carbamo­thio­ylhydrazinyl­idene)eth­yl]phenyl benzoate

    PubMed Central

    Viswanathan, Vijayan; Ananth, Mani Karthik; Narasimhan, S.; Velmurugan, Devadasan

    2017-01-01

    In the title compounds, C11H13N3O2S, (I), and C16H15N3O2S, (II), the thio­semicarbazone group adopts an extended conformation. The acetate ester (I) crystallizes with two independent mol­ecules in the asymmetric unit. In the benzoate ester (II), the planes of the two aryl rings are inclined to one another by 46.70 (7)°. In both compounds, there is a short intra­molecular N—H⋯N contact present, forming an S(5) ring motif. In the crystals of both compounds, mol­ecules are linked via pairs of N—H⋯S hydrogen bonds, forming dimers with R 2 2(8) ring motifs. The dimers are linked by N—H⋯S and N—H⋯O hydrogen bonds, forming slabs parallel to (01-1). In (I), there are N—H⋯π and C—H⋯π inter­actions present within the slabs, while in (II), there are only N—H⋯π inter­actions present. PMID:28083126

  9. N-Succinimidyl 3-((4-(4-[18F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(guanidinomethyl)benzoate ([18F]SFBTMGMB): A Residualizing Label for 18F-labeling of internalizing biomolecules

    PubMed Central

    Vaidyanathan, Ganesan; McDougald, Darryl; Choi, Jaeyeon; Pruszynski, Marek; Koumarianou, Eftychia; Zhou, Zhengyuan; Zalutsky, Michael R.

    2015-01-01

    Residualizing labeling methods for internalizing peptides and proteins are designed to trap the radionuclide inside the cell after intracellular degradation of the biomolecule. The goal of this work was to develop a residualizing label for the 18F-labeling of internalizing biomolecules based on a template used successfully for radioiodination. N-succinimidyl 3-((4-(4-[18F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(bis-Boc-guanidinomethyl)benzoate (Boc2-[18F]SFBTMGMB) was synthesized by click reaction of an azide precursor and [18F]fluorohexyne in 8.5 ± 2.8% average decay-corrected radiochemical yield (n =15). An anti-HER2 nanobody 5F7 was labeled with 18F using [18F]SFBTMGMB ([18F]RL-I), obtained by the deprotection of Boc2-[18F]SFBTMGMB, in 31.2 ± 6.7% (n =5) conjugation efficiency. Thus labeled nanobody had a radiochemical purity of >95%, bound to the HER2-expressing BT474M1 breast cancer cells with an affinity of 4.7 ± 0.9 nM, and had an immunoreactive fraction of 62–80%. In summary, a novel residualizing prosthetic agent for labeling biomolecules with 18F has been developed. An anti-HER2 nanobody was labeled using this prosthetic group with retention of affinity and immunoreactivity to HER2. PMID:26645790

  10. Characterization of multidrug transporter-mediated efflux of avermectins in human and mouse neuroblastoma cell lines.

    PubMed

    Dalzell, Abigail M; Mistry, Pratibha; Wright, Jayne; Williams, Faith M; Brown, Colin D A

    2015-06-15

    ABC transporters play an important role in the disposition of avermectins in several animal species. In this study the interactions of three key avermectins, abamectin, emamectin and ivermectin, with human and mouse homologues of MDR1 (ABCB1/Abcb1a) and MRP (ABCC/Abcc), transporters endogenously expressed by human SH-SY5Y and mouse N2a neuroblastoma cells were investigated. In both cell lines, retention of the fluorescent dye H33342 was found to be significantly increased in the presence of avermectins and cyclosporin A. These effects were shown to be unresponsive to the BCRP inhibitor Ko-143 and therefore MDR1/Mdr1-dependent. Avermectins inhibited MDR1/Mdr1a-mediated H33342 dye efflux, with apparent Ki values of 0.24±0.08 and 0.18±0.02μM (ivermectin); 0.60±0.07 and 0.56±0.02μM (emamectin) and 0.95±0.08 and 0.77±0.25μM (abamectin) in SH-SY5Y and N2a cells, respectively. There were some apparent affinity differences for MDR1 and Mdr1a within each cell line (affinity for ivermectin>emamectin≥abamectin, P<0.05 by One-Way ANOVA), but importantly, the Ki values for individual avermectins for human MDR1 or mouse Mdr1a were not significantly different. MK571-sensitive retention of GSMF confirmed the expression of MRP/Mrp efflux transporters in both cell lines. Avermectins inhibited MRP/Mrp-mediated dye efflux with IC50 values of 1.58±0.51 and 1.94±0.72μM (ivermectin); 1.87±0.57 and 2.74±1.01μM (emamectin) and 2.25±0.01 and 1.68±0.63μM (abamectin) in SH-SY5Y and N2a cells, respectively. There were no significant differences in IC50 values between individual avermectins or between human MRP and mouse Mrp. Kinetic data for endogenous human MDR1/MRP isoforms in SH-SY5Y cells and mouse Mdr1a/b/Mrp isoforms in N2a cells are comparable for the selected avermectins. All are effluxed at concentrations well above 0.05-0.1μM ivermectin detected in plasma (Ottesen and Campbell, 1994; Ottesen and Campbell, 1994) This is an important finding in the light of

  11. Survey of Susceptibilites to Monosultap, Triazophos, Fipronil, and Abamectin in Chilo suppressalis (Lepidoptera: Crambidae)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    To provide a foundation for national resistance management of the rice stem borer, Chilo suppressalis (Walker), a systematic study was carried out to determine dose response and susceptibility changes over a five-year period in the insect from representative rice production regions. A total of eleve...

  12. Realization of unusual ligand binding motifs in metalated container molecules: synthesis, structures, and magnetic properties of the complexes [(LMe)Ni2(mu-L')]n+ with L'=NO3-, NO2-, N3-, N2H4, pyridazine, phthalazine, pyrazolate, and benzoate.

    PubMed

    Hausmann, Julia; Klingele, Marco H; Lozan, Vasile; Steinfeld, Gunther; Siebert, Dieter; Journaux, Yves; Girerd, Jean Jacques; Kersting, Berthold

    2004-04-02

    A series of dinickel(II) complexes with the 24-membered macrocyclic hexaazadithiophenol ligand H(2)L(Me) was prepared and examined. The doubly deprotonated form (L(Me))(2-) forms complexes of the type [(L(Me))Ni2II(mu-L')](n+) with a bioctahedral N(3)Ni(II)(mu-SR)(2)(mu-L')Ni(II)N(3) core and an overall calixarene-like structure. The bridging coordination site L' is accessible for a wide range of exogenous coligands. In this study L'=NO(3)(-), NO(2)(-), N(3)(-), N(2)H(4), pyrazolate (pz), pyridazine (pydz), phthalazine (phtz), and benzoate (OBz). Crystallographic studies reveal that each substrate binds in a distinct fashion to the [(L(Me))Ni(2)](2+) portion: NO(2)(-), N(2)H(4), pz, pydz, and phtz form mu(1,2)-bridges, whereas NO(3)(-), N(3)(-), and OBz(-) are mu(1,3)-bridging. These distinctive binding motifs and the fact that some of the coligands adopt unusual conformations is discussed in terms of complementary host-guest interactions and the size and form of the binding pocket of the [(L(Me))Ni(2)](2+) fragment. UV/Vis and electrochemical studies reveal that the solid-state structures are retained in the solution state. The relative stabilities of the complexes indicate that the [(L(Me))Ni(2)](2+) fragment binds anionic coligands preferentially over neutral ones and strong-field ligands over weak-field ligands. Secondary van der Waals interactions also contribute to the stability of the complexes. Intramolecular ferromagnetic exchange interactions are present in the nitrito-, pyridazine-, and the benzoato-bridged complexes where J=+6.7, +3.5, and +5.8 cm(-1) (H=-2 JS(1)S(2), S(1)=S(2)=1) as indicated by magnetic susceptibility data taken from 300 to 2 K. In contrast, the azido bridge in [(L(Me))Ni(2)(mu(1,3)-N(3))](+) results in an antiferromagnetic exchange interaction J=-46.7 cm(-1). An explanation for this difference is qualitatively discussed in terms of bonding differences.

  13. Methyl 4-(piperidin-1-ylcarbon­yl)benzoate

    PubMed Central

    Ávila, R. M. D.; Landre, I. M. R.; Souza, T. E.; Veloso, M. P.; Doriguetto, A. C

    2010-01-01

    In the title compound, C14H17NO3, the piperidine ring has a chair conformation and an intra­molecular C—H⋯O inter­action stabilizes the mol­ecular conformation. In the crystal, weak inter­molecular C—H⋯O inter­actions occur. PMID:21587861

  14. 21 CFR 522.1940 - Progesterone and estradiol benzoate.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS IMPLANTATION OR INJECTABLE DOSAGE FORM NEW ANIMAL DRUGS... 400 pounds (lb) of body weight. For subcutaneous ear implantation, one dose per animal. Do not use in bull calves intended for reproduction. Safety and effectiveness have not been established in...

  15. [Zuclopenthixol benzoate poisoning in a child: evidence from chromatography].

    PubMed

    Menager, C; Boimond, N; Cheron, G

    2013-03-01

    Zuclopenthixol is a thioxanthene-based neuroleptic. It may cause acute intoxication in children with neurological and consciousness disorders. Immunochromatography is unable to identify the molecule and diagnosis requires mass spectroscopy and HP chromatography. The short time needed for this technique significantly improves the exploration and treatment of Clopixol(®) poisoning.

  16. Efficacy of some oils and chemical compounds on Insignorthezia insignis (Browne) (Hemiptera: Ortheziidae) infesting Lantana camara in Alexandria, Egypt.

    PubMed

    Moursi, S Khadiga; Abo-Shanab, A S H; Mesbah, H A; Abdel-Razak, S I; Mourad, A K; Zaghloul, O A; Abdel-Fatah, R S

    2010-01-01

    Field and laboratory experiments were conducted in March, 2008 in El-Nouzha garden, Alexandria governorate. Pre-and post treatment inspections of the insects were examined and recorded before and after (2,4,8, and 12 weeks). Spraying was applied to evaluate the efficiency of the tested compounds, [Mineral oils (KZ oil and Star oil); IGRs (Chlorfluazuron, lufenuron and pyriproxyfen); Neem oil; emamectin benzoate and thiamethoxam]. Percentages of reduction were calculated. The ensign scale insects Insignorthezia insignis (Browne) were collected from treated Lantana camara shrubs to investigate the effect of the tested chemicals on Aspartate transferase (AST), Alanine transferase (ALT) and Alkaline-phosphatase (ALPK) of the insect enzymes activities. From the obtained results, it could be concluded that the tested materials gave good results for controlling both adult and immature stages of the ensign scale insect Insignorthezia insignis (Browne) that infested Lantana camara shrubs, through affecting enzymes activities of the assigned insect pest.

  17. Biocatalytic Conversion of Avermectin to 4"-Oxo-Avermectin: Characterization of Biocatalytically Active Bacterial Strains and of Cytochrome P450 Monooxygenase Enzymes and Their Genes

    PubMed Central

    Jungmann, Volker; Molnár, István; Hammer, Philip E.; Hill, D. Steven; Zirkle, Ross; Buckel, Thomas G.; Buckel, Dagmar; Ligon, James M.; Pachlatko, J. Paul

    2005-01-01

    4"-Oxo-avermectin is a key intermediate in the manufacture of the agriculturally important insecticide emamectin benzoate from the natural product avermectin. Seventeen biocatalytically active Streptomyces strains with the ability to oxidize avermectin to 4"-oxo-avermectin in a regioselective manner have been discovered in a screen of 3,334 microorganisms. The enzymes responsible for this oxidation reaction in these biocatalytically active strains were found to be cytochrome P450 monooxygenases (CYPs) and were termed Ema1 to Ema17. The genes for Ema1 to Ema17 have been cloned, sequenced, and compared to reveal a new subfamily of CYPs. Ema1 to Ema16 have been overexpressed in Escherichia coli and purified as His-tagged recombinant proteins, and their basic enzyme kinetic parameters have been determined. PMID:16269732

  18. A comparative assessment of cytotoxicity of commonly used agricultural insecticides to human and insect cells.

    PubMed

    Yun, Xinming; Huang, Qingchun; Rao, Wenbing; Xiao, Ciying; Zhang, Tao; Mao, Zhifan; Wan, Ziyi

    2017-03-01

    The cytotoxic potential of 13 commonly used agricultural insecticides was examined using cell-based systems with three human HepG2, Hek293, HeLa cells and three insect Tn5B1-4, Sf-21, and Drosophila S2 cells. Data showed that (1) an enhancement of some insecticides (e.g. pyrethroids) on cells proliferation; (2) an inhibition of some insecticides on cells viability; (3) various levels of susceptibility of different cells to the same insecticide; and (4) the cell type dependent sensitivity to different insecticides. The degree of cytotoxicity of insecticides on human cells was significantly lower than that on insect cells (P<0.05). Methomyl, even 20μg/ml, showed little cytotoxicity at 24h exposure whereas emamectin benzoate possessed the strongest cytotoxic potential in a dose-dependent fashion. The results revealed comparable cytotoxic property of agricultural insecticides against intact cells.

  19. Resistance of Dusky Cotton Bug, Oxycarenus hyalinipennis Costa (Lygaidae: Hemiptera), to Conventional and Novel Chemistry Insecticides.

    PubMed

    Ullah, Saif; Shad, Sarfraz Ali; Abbas, Naeem

    2016-02-01

    The dusky cotton bug, Oxycarenus hyalinipennis Costa (Lygaidae: Hemiptera), is polyphagous in nature and has become one of the severe sucking pests of cotton in Pakistan. O. hyalinipennis has the potential to develop resistance to a number of insecticides, and as a result, O. hyalinipennis outbreaks occur. There is no previous study from Pakistan regarding O. hyalinipennis resistance to insecticides. Therefore, the aim of this study was to assess the resistance of different field populations of O. hyalinipennis to conventional (bifenthrin, deltamethrin, lambda-cyhalothrin, profenofos, triazophos) and novel chemistry (emamectin benzoate, spinosad, chlorfenapyr, imidacloprid, and nitenpyram) insecticides. Five populations of O. hyalinipennis, collected from Multan, Khanewal, Muzaffargarh, Lodhran, and Bahawalpur, were tested for resistance to selected insecticides by the leaf dip method. For three pyrethroids, the resistance ratios were in the range of 14- to 30-fold for bifenthrin, 2.14- to 8.41-fold for deltamethrin, and 9.12- to 16-fold for lambda-cyhalothrin, compared with the laboratory susceptible strain (Lab-PK). For two organophosphates, the range of resistance ratios was 12- to 14-fold for profenofos and 9.04- to 15-fold for triazophos. For five novel chemistry insecticides, the range of resistance ratios was 4.68- to 9.83-fold for emamectin benzoate, 6.38- to 17-fold for spinosad, 16- to 46-fold for chlorfenapyr, 11- to 22-fold for imidacloprid, and 1.32- to 11-fold for nitenpyram. Regular assessment of resistance to insecticides and integrated management plans like judicious use of insecticides and rotation of insecticides along with different modes of action are required to delay resistance development in O. hyalinipennis.

  20. Characterizing heat shock protein 90 gene of Apolygus lucorum (Meyer-Dür) and its expression in response to different temperature and pesticide stresses.

    PubMed

    Sun, Yang; Sheng, Yang; Bai, Lixin; Zhang, Yongjun; Xiao, Yingfang; Xiao, Liubin; Tan, Yongan; Shen, Youmi

    2014-09-01

    In this study, we cloned a full-length cDNA of heat shock protein (HSP) gene of Apolygus lucorum (Meyer-Dür) [AlHSP90, KC109781] and investigated its expression in response to temperature and pesticide stresses. The open reading frame (ORF) of AlHSP90 is 2,169 bp in length, encoding a 722 amino acid polypeptide with a predicted molecular weight of 82.99 kDa. Transcriptional and translational expression profiles of AlHSP90 under extreme temperature or pesticide stresses were examined by fluorescent real-time quantitative PCR and Western blot. Results showed that the expression profiles of AlHSP90 protein were in high agreement with those of AlHSP90 RNA and indicated that AlHSP90 was not only an important gene for A. lucorum adults in response to extremely high temperature, but also involved in the resistance or tolerance to cyhalothrin, imidacloprid, chlorpyrifos, and emamectin benzoate, especially for female adults to emamectin benzoate and for male adults to cyhalothrin. Transcriptional results of AlHSP90 also confirmed that AlHSP90 was an important gene involved in the resistance or tolerance to both temperature and pesticide stresses. In addition, our study also revealed that ∼24 °C may be the suitable temperature range for A. lucorum survival, which is also confirmed by the results of the expression of AlHSP90, the nymph mortality, and the intrinsic rate of increase (r m) when A. lucorum is reared at six different temperatures. Therefore, these studies are significant in elucidating the AlHSP90 in response to temperature and pesticide stresses and would provide guidance for A. lucorum management with different pesticides or temperatures in fields.

  1. Field resistance of Spodoptera litura (Lepidoptera: Noctuidae) to organophosphates, pyrethroids, carbamates and four newer chemistry insecticides in Hunan, China.

    PubMed

    Tong, Hong; Su, Qi; Zhou, Xiaomao; Bai, Lianyang

    2013-01-01

    The present studies were carried out to evaluate resistance in the populations of Spodoptera litura Fab. (Lepidoptera, Noctuidae) from five districts of Hunan Province in China to various insecticides from 2010 to 2012 using a standard leaf dip bioassay method. For organophosphates and pyrethroids, resistance ratios compared with a susceptible Lab-BJ strain were in the range of 14-229-fold for organophosphates and 12-227-fold for pyrethroids. Similarly, relative low levels of resistance to emamectin, indoxacarb, and chlorfenapyr were observed in all five populations. In contrast, the resistance to carbamates (thiodicarb or methomyl) was significantly higher than that of organophosphates, pyrethroids and newer chemistry insecticides. The pairwise correlation coefficients of LC50 values indicated that the newer chemistry insecticides and old generation insecticides were not significant except abamectin, which was negatively significantly correlated with methomyl. A significant correlation was observed between thiodicarb, methomyl, and deltamethrin, whereas resistance to bifenthrin showed no correlations with resistance to other insecticides except deltamethrin. The results are discussed in relation to integrated pest management for S. litura with special reference to management of field evolved resistance to insecticides.

  2. Effect of some commonly used pesticides on seed germination, biomass production and photosynthetic pigments in tomato (Lycopersicon esculentum).

    PubMed

    Shakir, Shakirullah Khan; Kanwal, Memoona; Murad, Waheed; Zia ur Rehman; Shafiq ur Rehman; Daud, M K; Azizullah, Azizullah

    2016-03-01

    Pesticides are highly toxic substances. Their toxicity may not be absolutely specific to the target organisms but can adversely affect different processes in the non-target host plants. In the present study, the effect of over application of four commonly used pesticides (emamectin benzoate, alpha-cypermethrin, lambda-cyhalothrin and imidacloprid) was evaluated on the germination, seedling vigor and photosynthetic pigments in tomato. The obtained results revealed that seed germination was decreased by the pesticides and this effect was more prominent at early stages of exposure. All the tested pesticides reduced the growth of tomato when applied in higher concentration than the recommended dose, but at lower doses the pesticides had some stimulatory effects on growth as compared to the control. A similar effect of pesticides was observed on the photosynthetic pigments, i.e. a decrease in pigments concentrations was caused at higher doses but an increase was observed at lower doses of pesticides. The calculation of EC50 values for different parameters revealed the lowest EC50 values for emamectin (ranged as 51-181 mg/L) followed by alpha-cypermethrin (191.74-374.39), lambda-cyhalothrin (102.43-354.28) and imidacloprid (430.29-1979.66 mg/L). A comparison of the obtained EC50 values for different parameters of tomato with the recommended doses revealed that over application of these pesticides can be harmful to tomato crop. In a few cases these pesticides were found toxic even at the recommended doses. However, a field based study in this regard should be conducted to further verify these results.

  3. The Effect of Temperature on the Toxicity of Insecticides against Musca domestica L.: Implications for the Effective Management of Diarrhea

    PubMed Central

    Khan, Hafiz Azhar Ali; Akram, Waseem

    2014-01-01

    Background Diarrhea is an important cause of childhood mortality in developing countries like Pakistan because of unhygienic conditions, lack of awareness, and unwise use of preventive measures. Mechanical transmission of diarrheal pathogens by house flies, Musca domestica, is believed as the most effective route of diarrhea transmission. Although the use of insecticides as a preventive measure is common worldwide for the management of house flies, success of the measure could be compromised by the prevailing environmental temperature since it significantly affects toxicity of insecticides and thus their efficacy. Peaks of the house fly density and diarrheal cases are usually coincided and season specific, yet little is known about the season specific use of insecticides. Methodology/Principal Findings To determine the temperature-toxicity relationship in house flies, the effect of post-bioassays temperature (range, 20–34°C) on the toxicity of seven insecticides from organophosphate (chlorpyrifos, profenofos), pyrethroid (cypermethrin, deltamethrin) and new chemical (emamectin benzoate, fipronil, spinosad) classes was evaluated by using a feeding bioassay method. From 20–34°C, the toxicities of chlorpyrifos, profenofos, emamectin and fipronil increased 2.10, 2.93, 2.40 and 3.82 fold (i.e. positive temperature coefficient), respectively. Whereas, the toxicities of cypermethrin, deltamethrin and spinosad decreased 2.21, 2.42 and 3.16 fold (i.e. negative temperature coefficient), respectively. Conclusion/Significance These findings suggest that for the reduction in diarrheal cases, house flies should be controlled with insecticides according to the prevailing environmental temperature. Insecticides with a positive temperature coefficient may serve as potential candidates in controlling house flies and diarrhea epidemics in hot season and vice versa. PMID:24743188

  4. Systemically applied insecticides for treatment of erythrina gall wasp, quadrastichus erythrinae kim hymenoptera: Eulophidae

    USGS Publications Warehouse

    Doccola, J.J.; Smith, S.L.; Strom, B.L.; Medeiros, A.C.; Von Allmen, E.

    2009-01-01

    Abstract The erythrina gall wasp (EGW), believed native to Africa, is a recently described species and now serious invasive pest of Erythrina (coral trees) in tropical and subtropical locales. Erythrina are favored ornamental and landscape trees, as well as native members of threatened ecosystems. The EGW is a tiny, highly mobile, highly invasive wasp that deforms (galls) host trees causing severe defoliation and tree death. The first detection of EGW in the United States was in O'ahu, Hawai'i in April 2005. It quickly spread through the Hawai'ian island chain (U.S.) killing ornamental and native Erythrina in as little as two years. At risk are endemic populations of Erythrinaas well as ornamental landscape species in the same genus, the latter of which have already been killed and removed from O'ahu at a cost of more than USD $1 million. Because EGW are so small and spread so quickly, host injury is usually detected before adult wasps are observed, making prophylactic treatments less likely than therapeutic ones. This study evaluates two stem-injected insecticides, imidacloprid (IMA-jet??) and emamectin benzoate, delivered through Arborjet Tree I.V.?? equipment, for their ability to affect E. sandwicensis (wiliwili) canopy demise under severe EGW exposure. IMA-jet, applied at a rate of 0.16 g AI/cm basal diameter (0.4 g AI/in. dia.), was the only effective treatment for maintaining canopy condition of wiliwili trees. Emamectin benzoate, applied at a rate of -0.1 g AI/cm basal diameter (-0.25 g AI/in. dia.), was not effective in this application, although it was intermediate in effect between IMA-jet and untreated trees. The relatively high concentrations of imidacloprid in leaves, and its durability for at least 13 months in native wiliwili growing on a natural, dryland site, suggest that treatment applications against EGW can impact canopy recovery even under suboptimal site and tree conditions. ?? 2009 International Society of Arboriculture.

  5. Using organic-certified rather than synthetic pesticides may not be safer for biological control agents: selectivity and side effects of 14 pesticides on the predator Orius laevigatus.

    PubMed

    Biondi, Antonio; Desneux, Nicolas; Siscaro, Gaetano; Zappalà, Lucia

    2012-05-01

    The generalist predator Orius laevigatus (Fieber) (Hemiptera: Anthocoridae) is a key natural enemy of various arthropods in agricultural and natural ecosystems. Releases of this predator are frequently carried out, and it is included in the Integrated Pest Management (IPM) programs of several crops. The accurate assessment of the compatibility of various pesticides with predator activity is key for the success of this strategy. We assessed acute and sublethal toxicity of 14 pesticides on O. laevigatus adults under laboratory conditions. Pesticides commonly used in either conventional or organic farming were selected for the study, including six biopesticides, three synthetic insecticides, two sulfur compounds and three adjuvants. To assess the pesticides' residual persistence, the predator was exposed for 3d to pesticide residues on tomato sprouts that had been treated 1 h, 7 d or 14 d prior to the assay. The percentage of mortality and the sublethal effects on predator reproductive capacity were summarized in a reduction coefficient (E(x)) and the pesticides were classified according to the IOBC (International Organization for Biological Control) toxicity categories. The results showed that the pesticides greatly differed in their toxicity, both in terms of lethal and sub lethal effects, as well as in their persistence. In particular, abamectin was the most noxious and persistent, and was classified as harmful up to 14 d after the treatment, causing almost 100% mortality. Spinosad, emamectin, metaflumizone were moderately harmful until 7 d after the treatment, while the other pesticides were slightly harmful or harmless. The results, based on the combination of assessment of acute mortality, predator reproductive capacity pesticides residual and pesticides residual persistence, stress the need of using complementary bioassays (e.g. assessment of lethal and sublethal effects) to carefully select the pesticides to be used in IPM programs and appropriately time the

  6. Uncinataflavone, a new flavonoid with a methyl benzoate substituent from Selaginella uncinata.

    PubMed

    Zou, Hui; Xu, Kang-Ping; Li, Fu-Shuang; Zou, Zhen-Xing; Long, Hong-Ping; Li, Guang; Wang, Hui; Tan, Gui-Shan

    2013-01-01

    Uncinataflavone (1), a new flavonoid, together with four known compounds (2-5), was isolated from Selaginella uncinata (Desv.) Spring. Compounds 2 and 3 were isolated from the genus selaginella for the first time. The structure of the new compound was determined as methyl 3-(5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl)-4-methoxybenzoate by means of spectroscopic evidence, including UV, IR, 1D and 2D NMR analyses as well as HR-ESI-MS. These compounds (1-5) were evaluated for the antioxidant activity in 1,1-diphenyl-2-picrylhydrazyl assay system.

  7. 4-(2-Hydroxy­ethyl)anilinium 3,5-dinitro­benzoate

    PubMed Central

    Smith, Graham; Wermuth, Urs D.

    2009-01-01

    In the title compound, C8H12NO+·C7H3N2O6 −, the anilinium and hydroxyl protons of the cation result in N—H⋯O, N—H⋯(O,O) and O—H⋯O hydrogen-bonding inter­actions with carboxyl­ate O-atom acceptors, forming a two-dimensional network structure. An intermolecular C—H⋯O interaction is also present. PMID:21577524

  8. Phenyl 3,5-di-tert-butyl-2-hy­droxy­benzoate

    PubMed Central

    Carreño, Alexander; Preite, Marcelo; Manriquez, Juan Manuel; Vega, Andrés; Chavez, Ivonne

    2010-01-01

    The title mol­ecule, C21H26O3, has a six-membered planar carbon ring as the central core, substituted at position 1 with phen­oxy­carbonyl, at position 2 with hy­droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol­ecules within the asymmetric unit. For both independent mol­ecules, the ester carboxyl­ate group is coplanar with the central core, as reflected by the small C—C—O—C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl­ate –CO2 fragment, as reflected by C—O—C—C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl­ate –CO2– group allows the formation of an intra­molecular hydrogen bond, with O⋯O distances of 2.563 (2) and 2.604 (2) Å. PMID:21589569

  9. 2-Amino-5-bromo­pyridinium 5-chloro-2-hy­droxy­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Khalib, Nuridayanti Che; Arshad, Suhana; Razak, Ibrahim Abdul

    2013-01-01

    In the 5-chloro­salicylate anion of the title salt, C5H6BrN2 +·C7H4ClO3 −, an intra­molecular O—H⋯O hydrogen bond with an S(6) graph-set motif is formed, so that the anion is essentially planar with a dihedral angle of 1.3 (5)° between the benzene ring and the carboxyl­ate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms via a pair of N—H⋯O hydrogen bonds, forming an R 2 2(8) ring motif. The crystal structure also features N—H⋯O and weak C—H⋯O inter­actions, resulting in a layer parallel to the (10-1) plane. PMID:23634078

  10. 76 FR 12873 - Potassium Benzoate; Exemption From the Requirement of a Tolerance

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-03-09

    ....'' This includes exposure through drinking water and in residential settings, but does not include... the inert ingredient through food, drinking water, and through other exposures that occur as a result... (food and drinking water), or for the short, intermediate, and long term residential...

  11. 77 FR 31722 - New Animal Drugs; Change of Sponsor; Estradiol; Estradiol Benzoate and Testosterone Propionate...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2012-05-30

    ... and testosterone propionate) with TYLAN (tylosin tartrate). 200-221 COMPONENT TE-IS 522.2477 (trenbolone acetate and estradiol). COMPONENT TE-S (trenbolone acetate and estradiol). COMPONENT TE-G (trenbolone acetate and estradiol). COMPONENT TE-IS (trenbolone acetate and estradiol) with TYLAN...

  12. 2-Isopropyl-4-meth­oxy-5-methyl­phenyl benzoate

    PubMed Central

    Moumou, Mohamed; Akssira, Mohamed; Elhakmaoui, Ahmed; El Ammari, Lahcen; Benharref, Ahmed; Berraho, Moha

    2010-01-01

    The title compound, C18H20O3, a hemisynthetic product, was obtained by the reaction of benzoyl chloride and p-methoxy­thymol. The structure comprises two benzene rings bridged by a carboxyl group; the dihedral angle between the rings is 73.54 (8)°. PMID:21580674

  13. 40 CFR 721.10352 - Dimethyl terephthalate, polymer with alkyl diol and substituted benzoates (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Dimethyl terephthalate, polymer with... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10352 Dimethyl terephthalate, polymer... subject to reporting. (1) The chemical substance identified generically as dimethyl terephthalate,...

  14. 40 CFR 721.10352 - Dimethyl terephthalate, polymer with alkyl diol and substituted benzoates (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Dimethyl terephthalate, polymer with... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10352 Dimethyl terephthalate, polymer... subject to reporting. (1) The chemical substance identified generically as dimethyl terephthalate,...

  15. 40 CFR 721.10352 - Dimethyl terephthalate, polymer with alkyl diol and substituted benzoates (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Dimethyl terephthalate, polymer with... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10352 Dimethyl terephthalate, polymer... subject to reporting. (1) The chemical substance identified generically as dimethyl terephthalate,...

  16. Crystal structure of quinolinium 2-carboxy-6-nitro­benzoate monohydrate

    PubMed Central

    Mohana, J.; Divya Bharathi, M.; Ahila, G.; Chakkaravarthi, G.; Anbalagan, G.

    2015-01-01

    In the anion of the title hydrated mol­ecular salt, C9H8N+·C8H4NO6 −·H2O, the protonated carboxyl and nitro groups makes dihedral angles of 27.56 (5) and 6.86 (8)°, respectively, with the attached benzene ring, whereas the deprotonated carb­oxy group is almost orthogonal to it with a dihedral angle of 80.21 (1)°. In the crystal, the components are linked by O—H⋯O and N—H⋯O hydrogen bonds, generating [001] chains. The packing is consolidated by weak C—H⋯N and C—H⋯O inter­actions as well as aromatic π–π stacking [centroid-to-centroid distances: 3.7023 (8) & 3.6590 (9)Å] inter­actions, resulting in a three-dimensional network. PMID:25995899

  17. Biotinyl-methyl 4-(amidomethyl) benzoate is a competitive inhibitor of human biotinidase

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Posttranslational modification of histones by biotinylation can be catalyzed by both biotinidase (BTD) and holocarboxylase synthetase (HCS). Biotinylation of histones is an important epigenetic mechanism to regulate gene expression, DNA repair, and chromatin remodeling. The role of BTD in histone ...

  18. Effects of Some Pesticides on Development of Ascaris suum Eggs

    PubMed Central

    Yu, Yong-Man; Kim, Jin-Won; Na, Won-Seok; Youn, Young-Nam; Choi, In-Wook

    2014-01-01

    To evaluate the effects of pesticides to parasite eggs, Ascaris suum eggs were incubated with 5 different pesticides (1:1,500-1:2,000 dilutions of 2% emamectin benzoate, 5% spinetoram, 5% indoxacarb, 1% deltamethrin, and 5% flufenoxuron; all v/v) at 20℃ for 6 weeks, and microscopically evaluated the egg survival and development on a weekly basis. The survival rate of A. suum eggs incubated in normal saline (control eggs) was 90±3% at 6 weeks. However, the survival rates of eggs treated with pesticides were 75-85% at this time, thus significantly lower than the control value. Larval development in control eggs commenced at 3 weeks, and 73±3% of eggs had internal larvae at 6 weeks. Larvae were evident in pesticide-treated eggs at 3-4 weeks, and the proportions of eggs carrying larvae at 6 weeks (36±3%-54±3%) were significantly lower than that of the control group. Thus, pesticides tested at levels similar to those used in agricultural practices exhibited low-level ovicidal activity and delayed embryogenesis of A. suum eggs, although some differences were evident among the tested pesticides. PMID:24623893

  19. Effects of some pesticides on development of Ascaris suum eggs.

    PubMed

    Yu, Yong-Man; Kim, Jin-Won; Na, Won-Seok; Youn, Young-Nam; Choi, In-Wook; Lee, Young-Ha

    2014-02-01

    To evaluate the effects of pesticides to parasite eggs, Ascaris suum eggs were incubated with 5 different pesticides (1:1,500-1:2,000 dilutions of 2% emamectin benzoate, 5% spinetoram, 5% indoxacarb, 1% deltamethrin, and 5% flufenoxuron; all v/v) at 20℃ for 6 weeks, and microscopically evaluated the egg survival and development on a weekly basis. The survival rate of A. suum eggs incubated in normal saline (control eggs) was 90±3% at 6 weeks. However, the survival rates of eggs treated with pesticides were 75-85% at this time, thus significantly lower than the control value. Larval development in control eggs commenced at 3 weeks, and 73±3% of eggs had internal larvae at 6 weeks. Larvae were evident in pesticide-treated eggs at 3-4 weeks, and the proportions of eggs carrying larvae at 6 weeks (36±3%-54±3%) were significantly lower than that of the control group. Thus, pesticides tested at levels similar to those used in agricultural practices exhibited low-level ovicidal activity and delayed embryogenesis of A. suum eggs, although some differences were evident among the tested pesticides.

  20. Identification of heat shock cognate protein 70 gene (Alhsc70) of Apolygus lucorum and its expression in response to different temperature and pesticide stresses.

    PubMed

    Sun, Yang; Zhao, Jing; Sheng, Yang; Xiao, Ying-Fang; Zhang, Yong-Jun; Bai, Li-Xin; Tan, Yongan; Xiao, Liu-Bin; Xu, Guang-Chun

    2016-02-01

    Heat shock cognate protein 70 (Hsc70) is a very important stress-resistance protein of insects against environmental stresses. We employed fluorescent real-time quantitative polymerase chain reaction and Western-blot techniques to analyze the transcriptional and translational expression profiles of AlHSC70 under extreme temperature (4°C and 40°C) or 4 pesticide stresses in Apolygus lucorum. The results showed that the expression of AlHSC70 were significantly induced by cyhalothrin or extremely high temperature (40°C) in both transcriptional and translational levels (P < 0.05), while the transcriptional and translational level of AlHSC70 decreased significantly in treatments of chlorpyrifos or extreme cold temperature (4°C) (P < 0.05). Moreover, after Apolygus lucorum treated by imidacloprid or emamectin benzoate, the expression of AlHSC70 was only up-regulated significantly at the transcriptional level (P < 0.05), although obviously up-regulated at the translational level of AlHSC70. Therefore, this study confirmed that the Alhsc70 gene played important roles in response to both temperature and pesticide stresses, especially for cyhalothrin or extremely high temperature (40°C). In addition, the significant polynomial regression correlations between temperature and the Alhsc70 expression level were shown in all the nymph and adult stages (P < 0.01), indicating temperature was an important factor to affect the relative expression of Alhsc70.

  1. The Toxicology and Biochemical Characterization of Cantharidin on Cydia pomonella.

    PubMed

    Wu, Zheng-Wei; Yang, Xue-Qing; Zhang, Ya-Lin

    2015-02-01

    Cantharidin, a natural toxin produced by beetles in the families Meloidae and Oedemeridae, reported to be toxic to some pests, is being developed as a biopesticide in China. This study evaluates the toxicity and biochemical characterization of cantharidin on the codling moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae), an economically important fruit pest, under both laboratory and field conditions. Laboratory dose response bioassays showed that the LC50 value of cantharidin against neonate larvae was 0.057 mg ml(-1). Exposure of the larvae to 0.024 and 0.057 mg ml(-1) of cantharidin resulted in significant reduction in larval body weight. Neonate larvae exposed to LC10 of cantharidin showed increased glutathione S-transferase activity and significantly reduced the carboxylesterase and cytochrome P450-dependent mixed-function oxidase activities. Results also showed 16 and 25% ovicidal activity at concentrations of 0.057 and 0.14 mg ml(-1) of cantharidin, respectively. Field trials demonstrated cantharidin has a significant effect on both the first and second generations of C. pomonella larvae, but it exhibits a lower control efficiency than the chemical reference emamectin benzoate. Cantharidin may be considered a valuable tool for the control of codling moth.

  2. Endocrine disruption in crustaceans due to pollutants: a review.

    PubMed

    Rodríguez, Enrique M; Medesani, Daniel A; Fingerman, Milton

    2007-04-01

    The main endocrine-regulated processes of crustaceans have been reviewed in relation to the effects of endocrine-disrupting compounds (EDCs). Molting has been shown to be inhibited by several organic pollutants, such as xenoestrogens and related compounds, as well as by some pesticides. Most of these disrupters are thought to interfere with ecdysone at target tissues, although only for a few has this action been demonstrated in vitro. The heavy metal cadmium appears to inhibit some ecdysone secretion. Juvenoid compounds have also been shown to inhibit molting, likely by interfering with the stimulatory effect of methyl farnesoate. A molt-promoting effect of emamectin benzoate, a pesticide, has also been reported. As for reproduction, a variety of organic compounds, including xenoestrogens, juvenoids and ecdysteroids, has produced abnormal development of male and female secondary sexual characters, as well as alteration of the sex ratio. Cadmium and copper have been shown to interfere with hormones that stimulate reproduction, such as methyl farnesoate, as well as with secretion of the gonad inhibiting hormone, therefore affecting, for example, ovarian growth. Several heavy metals were able to produce hyperglycemia in crustaceans during short times of exposure; while a hypoglycemic response was noted after longer exposures, due to inhibition of secretion of the crustacean hyperglycemic hormone. The ecological relevance of EDCs on crustaceans is discussed, mainly in relation to the identification of useful biomarkers and sentinel species. New experimental approaches are also proposed.

  3. First report of field evolved resistance to agrochemicals in dengue mosquito, Aedes albopictus (Diptera: Culicidae), from Pakistan

    PubMed Central

    2011-01-01

    Background Agrochemicals have been widely used in Pakistan for several years. This exposes mosquito populations, particularly those present around agricultural settings, to an intense selection pressure for insecticide resistance. The aim of the present study was to investigate the toxicity of representative agrochemicals against various populations of Aedes albopictus (Skuse) collected from three different regions from 2008-2010. Results For organophosphates and pyrethroids, the resistance ratios compared with susceptible Lab-PK were in the range of 157-266 fold for chlorpyrifos, 24-52 fold for profenofos, 41-71 fold for triazofos, and 15-26 fold for cypermethrin, 15-53 fold for deltamethrin and 21-58 fold for lambdacyhalothrin. The resistance ratios for carbamates and new insecticides were in the range of 13-22 fold for methomyl, 24-30 fold for thiodicarb, and 41-101 fold for indoxacarb, 14-27 fold for emamectin benzoate and 23-50 fold for spinosad. Pair wise comparisons of the log LC50s of insecticides revealed correlation among several insecticides, suggesting a possible cross resistance mechanism. Moreover, resistance remained stable across 3 years, suggesting field selection for general fitness had also taken place for various populations of Ae. albopictus. Conclusion Moderate to high level of resistance to agrochemicals in Pakistani field populations of Ae. albopictus is reported here first time. The geographic extent of resistance is unknown but, if widespread, may lead to problems in future vector control. PMID:21781290

  4. Impact of early salmon louse, Lepeophtheirus salmonis, infestation and differences in survival and marine growth of sea-ranched Atlantic salmon, Salmo salar L., smolts 1997-2009.

    PubMed

    Skilbrei, O T; Finstad, B; Urdal, K; Bakke, G; Kroglund, F; Strand, R

    2013-03-01

    The impact of salmon lice on the survival of migrating Atlantic salmon smolts was studied by comparing the adult returns of sea-ranched smolts treated for sea lice using emamectin benzoate or substance EX with untreated control groups in the River Dale in western Norway. A total of 143 500 smolts were released in 35 release groups in freshwater from 1997 to 2009 and in the fjord system from 2007 to 2009. The adult recaptures declined gradually with release year and reached minimum levels in 2007. This development corresponded with poor marine growth and increased age at maturity of ranched salmon and in three monitored salmon populations and indicated unfavourable conditions in the Norwegian Sea. The recapture rate of treated smolts was significantly higher than the controls in three of the releases performed: the only release in 1997, one of three in 2002 and the only group released in sea water in 2007. The effect of treating the smolts against salmon lice was smaller than the variability in return rates between release groups, and much smaller that variability between release years, but its overall contribution was still significant (P < 0.05) and equivalent to an odds ratio of the probability of being recaptured of 1.17 in favour of the treated smolts. Control fish also tended to be smaller as grilse (P = 0.057), possibly due to a sublethal effect of salmon lice.

  5. Single-dose field bioassay for sensitivity testing in sea lice, Lepeophtheirus salmonis: development of a rapid diagnostic tool.

    PubMed

    Helgesen, K O; Horsberg, T E

    2013-03-01

    Sea lice on farmed salmonids are often treated with chemicals. Sensitivity testing of sea lice can reduce the number of treatments by identifying substances the sea lice are susceptible to. This study describes a simpler protocol for field sensitivity testing than today's six-dose bioassay. The protocol, which uses a single dose of the delousing agents deltamethrin, azamethiphos and emamectin benzoate, was developed on four different strains of sea lice and their subsequent generations. A sensitive strain and a strain showing reduced sensitivity were identified for each chemical after performing traditional bioassays and small-scale treatments. The single doses for each chemical were established by modelling dose-response curves from 24-h bioassays on strains with differences in sensitivity. The largest difference between the lower 80% prediction interval for the sensitive strain and the upper 80% prediction interval for the strain showing reduced sensitivity was identified for each delousing agent. The concentration of the chemical and the % mortality corresponding to each of the 80% prediction intervals were subsequently established. To validate the protocol for field use, further studies on both sensitive and resistant strains of sea lice under field conditions are required.

  6. Toxicity of 25 synthetic insecticides to the field population of Culex quinquefasciatus Say.

    PubMed

    Shah, Rizwan Mustafa; Alam, Mahbob; Ahmad, Daniyal; Waqas, Muhammad; Ali, Qasim; Binyamin, Muhammad; Shad, Sarfraz Ali

    2016-11-01

    The Culex quinquefaciatus Say, commonly known as the southern house mosquito, is well known for biting nuisance and vectoring of some fatal diseases. Synthetic chemicals have been relied upon as the major control measure to control mosquitoes. Therefore, we have evaluated 21 insecticides belonging to different chemical classes for their toxicity to C. quinquefaciatus females. Chlorfenapyr was the most toxic adulticide among all the tested insecticides. Among pyrethroids, deltamethrin was the least toxic adulticide, and all other have same toxicity. In case of organophosphates, the chlorpyrifos was the most toxic insecticide. Neonicotinoids such as acetamiprid, nitenpyram, and clothianidin have similar toxicity based on overlapping of 95 % confidence intervals (CI) and were more toxic when compared with the imidacloprid. The spinetoram was more toxic as compared with the spinosad (based on non-overlapping 95 % Cl). In case of ketoenoles, spirotetrament was more toxic as compared with the spiromesifen. Emamectin benzoate was the most toxic insecticide when compared with fipronil and indoxacarb. We also have tested four insect growth regulators (IGRS) including lufenuron, methoxyfenozide, pyriproxyfen, and cyromazine as larvicides. The lufenuron and pyriproxyfen have similar toxicity based upon their overlapping 95 % CI and were more toxic as compared with the methoxyfenozide and cyromazine. The methoxyfenozide was the moderately toxic among all the tested IGRS, and cyromazine was the least toxic among all the tested IGRS. These results will prove helpful in effectuating an effective integrated vector management program for C. quinquefaciatus.

  7. Crystal structure of 2-oxo-2H-chromen-3-yl 4-chloro­benzoate and Hirshfeld surface analysis

    PubMed Central

    Ziki, Eric; Sosso, Siaka; Mansilla-Koblavi, Frédérica; Djandé, Abdoulaye; Kakou-Yao, Rita

    2017-01-01

    In the title compound, C16H9ClO4 the dihedral angle between the coumarin ring system [maximum deviation = 0.023 (1) Å] and the benzene ring is 73.95 (8)°. In the crystal, π–π inter­actions link the dimers into a three-dimensional framework. A quantum chemical calculation is in generally good agreement with the observed structure, although the calculated dihedral angle between the ring systems (85.7%) is somewhat larger than the observed value [73.95 (8)°]. Hirshfeld surface analysis has been used to confirm and qu­antify the supra­molecular inter­actions. PMID:28083133

  8. A tetrahedron in a cube: a dodecanuclear Zn(II) benzoate cluster from the use of 2-pyridinealdoxime.

    PubMed

    Konidaris, Konstantis F; Katsoulakou, Eugenia; Kaplanis, Michalis; Bekiari, Vlasoula; Terzis, Aris; Raptopoulou, Catherine P; Manessi-Zoupa, Evy; Perlepes, Spyros P

    2010-05-21

    The reactions of 2-pyridinealdoxime with Zn(O(2)CPh)(2)·2H(2)O have led to a mononuclear complex and a dodecanuclear cluster; the Zn(12) compound, whose metallic skeleton describes a tetrahedron encapsulated in a distorted cube, is the biggest Zn(II) oxime cluster discovered to date and displays photoluminescence with a maximum at 354 nm upon maximum excitation at 314 nm.

  9. Bis(quinolin-8-ol)silver(I) 2-hydr-oxy-3,5-dinitro-benzoate.

    PubMed

    Zhang, Chun-Lan; Jian, Fang-Fang

    2009-11-07

    The title compound, [Ag(C(9)H(7)NO)(2)](C(7)H(3)N(2)O(7)), was prepared from 3,5-dinitro-salicylic acid (DNS), quinolin-8-ol and AgNO(3). The Ag(I) atom is coordinated by two N atoms and two O atoms from two quinolin-8-ols in a roughly planar [maximum deviation = 0.223 (2) Å] environment. The two quinolin-8-ol ligands are bent slightly with respect to each other, making a dihedral angle of 9.55 (9)°. The DNS anion inter-acts with the silver complex through O-H⋯O hydrogen bonds.

  10. Crystal structure of 2-oxo-2H-chromen-3-yl 4-chloro-benzoate and Hirshfeld surface analysis.

    PubMed

    Ziki, Eric; Sosso, Siaka; Mansilla-Koblavi, Frédérica; Djandé, Abdoulaye; Kakou-Yao, Rita

    2017-01-01

    In the title compound, C16H9ClO4 the dihedral angle between the coumarin ring system [maximum deviation = 0.023 (1) Å] and the benzene ring is 73.95 (8)°. In the crystal, π-π inter-actions link the dimers into a three-dimensional framework. A quantum chemical calculation is in generally good agreement with the observed structure, although the calculated dihedral angle between the ring systems (85.7%) is somewhat larger than the observed value [73.95 (8)°]. Hirshfeld surface analysis has been used to confirm and qu-antify the supra-molecular inter-actions.

  11. 2-Amino-5-methyl­pyridinium 2-hy­droxy-5-chloro­benzoate

    PubMed Central

    Thanigaimani, Kaliyaperumal; Farhadikoutenaei, Abbas; Arshad, Suhana; Razak, Ibrahim Abdul

    2013-01-01

    In the 5-chloro­salicylate anion of the title salt, C6H9N2 +·C7H4ClO3 −, an intra­molecular O—H⋯O hydrogen bond with an S(6) graph-set motif is observed and the dihedral angle between the benzene ring and the –CO2 group is 1.6 (6)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms via a pair of N—H⋯O hydrogen bonds, forming an R 2 2(8) ring motif. The crystal structure also features N—H⋯O and weak C—H⋯O inter­actions, resulting in a layer parallel to (10-1). PMID:23476391

  12. Methyl 2-(methylthio)benzoate: A sex attractant for the June beetles, Phyllophaga tristis and P. apicata

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Male antennae of Phyllophaga tristis (Fabricius) (Coleoptera: Scarabaeidae: Melolonthinae) were tested using a coupled gas chromatograph-electroantennogram detector (GC-EAD) system for electrophysiological responses to five sex pheromones identified from other Phyllophaga species including L-valine ...

  13. Evaluation of accelerated UV and thermal testing for benzene formation in beverages containing benzoate and ascorbic acid.

    PubMed

    Nyman, Patricia J; Wamer, Wayne G; Begley, Timothy H; Diachenko, Gregory W; Perfetti, Gracia A

    2010-04-01

    Under certain conditions, benzene can form in beverages containing benzoic and ascorbic acids. The American Beverage Assn. (ABA) has published guidelines to help manufacturers mitigate benzene formation in beverages. These guidelines recommend accelerated testing conditions to test product formulations, because exposure to ultraviolet (UV) light and elevated temperature over the shelf life of the beverage may result in benzene formation in products containing benzoic and ascorbic acids. In this study, the effects of UVA exposure on benzene formation were determined. Benzene formation was examined for samples contained in UV stabilized and non-UV stabilized packaging. Additionally, the usefulness of accelerated thermal testing to simulate end of shelf-life benzene formation was evaluated for samples containing either benzoic or ascorbic acid, or both. The 24 h studies showed that under intense UVA light benzene levels increased by as much as 53% in model solutions stored in non-UV stabilized bottles, whereas the use of UV stabilized polyethylene terephthalate bottles reduced benzene formation by about 13% relative to the non-UV stabilized bottles. Similar trends were observed for the 7 d study. Retail beverages and positive and negative controls were used to study the accelerated thermal testing conditions. The amount of benzene found in the positive controls and cranberry juice suggests that testing at 40 degrees C for 14 d may more reliably simulate end of shelf-life benzene formation in beverages. Except for cranberry juice, retail beverages were not found to contain detectable amounts of benzene (<0.05 ng/g) at the end of their shelf lives.

  14. Crystal structure of 8-hy-droxy-quinolin-ium 2-carboxy-6-nitro-benzoate mono-hydrate.

    PubMed

    Divya Bharathi, M; Ahila, G; Mohana, J; Chakkaravarthi, G; Anbalagan, G

    2015-04-01

    In the title hydrated salt, C9H8NO(+)·C8H4NO6 (-)·H2O, the deprotonated carboxyl-ate group is almost normal to its attached benzene ring [dihedral angle = 83.56 (8)°], whereas the protonated carboxyl-ate group is close to parallel [dihedral angle = 24.56 (9)°]. In the crystal, the components are linked by N-H⋯O and O-H⋯O hydrogen bonds, generating [001] chains. The packing is consolidated by C-H⋯O and π-π [centroid-to-centroid distances = 3.6408 (9) and 3.6507 (9) Å] inter-actions, which result in a three-dimensional network.

  15. Spectroscopic (FT-IR, FT-Raman, UV) and microbiological studies of di-substituted benzoates of alkali metals

    NASA Astrophysics Data System (ADS)

    Kalinowska, M.; Świsłocka, R.; Borawska, M.; Piekut, J.; Lewandowski, W.

    2008-06-01

    The FT-IR, FT-Raman and UV spectra of 3,5-dihydroxybenzoic and 3,5-dichlorobenzoic acids as well as lithium, sodium, potassium, rubidium, caesium 3,5-dihydroxy- and 3,5-dichlorobenzoates were recorded, assigned and compared. The theoretical geometries, Mulliken atomic charges, IR wavenumbers were obtained in B3LYP/6-311++G** level. On the basis of the gathered experimental and theoretical data the effect of metals and substituents on the electronic system of studied compounds were investigated. Moreover, the antimicrobiological activity of studied compounds against two species of bacteria: Bacillus subtilis, Staphylococus aureus and one species of yeast: Candida albicans were studied after 24 and 48 h of incubation. The attempt was made, to find out whether there is any correlation between the first principal component and the degree of growth inhibition exhibited by studied compounds in relation to selected microorganisms.

  16. Spectroscopic (FT-IR, FT-Raman, UV) and microbiological studies of di-substituted benzoates of alkali metals.

    PubMed

    Kalinowska, M; Swisłocka, R; Borawska, M; Piekut, J; Lewandowski, W

    2008-06-01

    The FT-IR, FT-Raman and UV spectra of 3,5-dihydroxybenzoic and 3,5-dichlorobenzoic acids as well as lithium, sodium, potassium, rubidium, caesium 3,5-dihydroxy- and 3,5-dichlorobenzoates were recorded, assigned and compared. The theoretical geometries, Mulliken atomic charges, IR wavenumbers were obtained in B3LYP/6-311++G** level. On the basis of the gathered experimental and theoretical data the effect of metals and substituents on the electronic system of studied compounds were investigated. Moreover, the antimicrobiological activity of studied compounds against two species of bacteria: Bacillus subtilis, Staphylococus aureus and one species of yeast: Candida albicans were studied after 24 and 48 h of incubation. The attempt was made, to find out whether there is any correlation between the first principal component and the degree of growth inhibition exhibited by studied compounds in relation to selected microorganisms.

  17. Insecticide resistance status of field populations of Spodoptera exigua (Lepidoptera: Noctuidae) from China.

    PubMed

    Che, Wunan; Shi, Tian; Wu, Yidong; Yang, Yihua

    2013-08-01

    Beet armyworm, Spodoptera exigua (Hübner), is a serious pest of vegetables in China, and its control is heavily dependent on chemical insecticides. The current resistance status of nine insecticides was investigated in 16 field populations collected from seven provinces of China during 2009-2012. Compared with the susceptible strain WH-S, some field populations evolved various levels of resistance to eight of the nine insecticides tested: emamectin benzoate (4- to 348-fold), indoxacarb (2- to 41-fold), spinosad (5- to 38-fold), chlorantraniliprole (2- to 44-fold), tebufenozide (2- to 87-fold), chlorfluazuron (3- to 31-fold), cypermethrin (79- to 1240-fold), and chlorpyrifos (8- to 3,080-fold), but no significant resistance was detected to chlorfenapyr (0.4- to 7-fold). This indicates that chlorfenapyr has no cross-resistance with these other currently used insecticides. Four consecutive years' resistance screening at two places shows that resistance patterns were different between populations from Luhe (Jiangsu Province) and Fengxian (Shanghai), which are approximately 300 km apart. Resistance levels to chlorpyrifos were much higher in populations from Luhe (877- to 3,080-fold) than from Fengxian (8- to 110-fold). Fengxian populations developed moderate levels of resistance to tebufenozide (13- to 87-fold), but no resistance in Luhe populations (2- to 6-fold). However, Luhe populations developed moderate levels of resistance to chlorfluazuron (21- to 31-fold), but there was no resistance in Fengxian populations (3- to 5-fold). It is suggested that local insecticide selection determined resistance patterns although S. exigua has long-distance migratory potential. Adaptive resistance management tactics (such as rotations) should be designed and implemented based on the resistance patterns of S. exigua for each geographic area.

  18. Reducing the impact of pesticides on biological control in Australian vineyards: pesticide mortality and fecundity effects on an indicator species, the predatory mite Euseius victoriensis (Acari: Phytoseiidae).

    PubMed

    Bernard, Martina B; Cole, Peter; Kobelt, Amanda; Horne, Paul A; Altmann, James; Wratten, Stephen D; Yen, Alan L

    2010-12-01

    Laboratory bioassays on detached soybean, Glycine max (L.) Merr., leaves were used to test 23 fungicides, five insecticides, two acaricides, one herbicide, and two adjuvants on a key Australian predatory mite species Euseius victoriensis (Womersley) in "worst-case scenario" direct overspray assays. Zero- to 48-h-old juveniles, their initial food, and water supply were sprayed to runoff with a Potter tower; spinosad and wettable sulfur residues also were tested. Tests were standardized to deliver a pesticide dose comparable with commercial application of highest label rates at 1,000 liter/ha. Cumulative mortality was assessed 48 h, 4 d, and 7 d after spraying. Fecundity was assessed for 7 d from start of oviposition. No significant mortality or fecundity effects were detected for the following compounds at single-use application at 1,000 liter/ha: azoxystrobin, Bacillus thuringiensis (Bt) subsp. kurstaki, captan, chlorothalonil, copper hydroxide, fenarimol, glyphosate, hexaconazole, indoxacarb, metalaxyl/copper hydroxide, myclobutanil, nonyl phenol ethylene oxide, phosphorous acid, potassium bicarbonate, pyraclostrobin, quinoxyfen, spiroxamine, synthetic latex, tebufenozide, triadimenol, and trifloxystrobin. Iprodione and penconazole had some detrimental effect on fecundity. Canola oil as acaricide (2 liter/100 liter) and wettable sulfur (200 g/100 liter) had some detrimental effect on survival and fecundity and cyprodinil/fludioxonil on survivor. The following compounds were highly toxic (high 48-h mortality): benomyl, carbendazim, emamectin benzoate, mancozeb, spinosad (direct overspray and residue), wettable sulfur (> or = 400 g/100 liter), and pyrimethanil; pyrimethanil had no significant effect on fecundity of surviving females. Indoxacarb safety to E. victoriensis contrasts with its toxicity to key parasitoids and chrysopid predators. Potential impact of findings is discussed.

  19. A Fungal Insecticide Engineered for Fast Per Os Killing of Caterpillars Has High Field Efficacy and Safety in Full-Season Control of Cabbage Insect Pests

    PubMed Central

    Liu, Yong-Jie; Liu, Jing; Ying, Sheng-Hua; Liu, Shu-Sheng

    2013-01-01

    Fungal insecticides developed from filamentous pathogens of insects are notorious for their slow killing action through cuticle penetration, depressing commercial interest and practical application. Genetic engineering may accelerate their killing action but cause ecological risk. Here we show that a Beauveria bassiana formulation, HV8 (BbHV8), engineered for fast per os killing of caterpillars by an insect midgut-acting toxin (Vip3Aa1) overexpressed in conidia has both high field efficacy and safety in full-season protection of cabbage from the damage of an insect pest complex dominated by Pieris rapae larvae, followed by Plutella xylostella larvae and aphids. In two fields repeatedly sprayed during summer, BbHV8 resulted in overall mean efficacies of killing of 71% and 75%, which were similar or close to the 70% and 83% efficacies achieved by commercially recommended emamectin benzoate but much higher than the 31% and 48% efficacies achieved by the same formulation of the parental wild-type strain (WT). Both BbHV8 and WT sprays exerted no adverse effect on a nontarget spider community during the trials, and the sprays did not influence saprophytic fungi in soil samples taken from the field plots during 4 months after the last spray. Strikingly, BbHV8 and the WT showed low fitness when they were released into the environment because both were decreasingly recovered from the field lacking native B. bassiana strains (undetectable 5 months after the spray), and the recovered isolates became much less tolerant to high temperature and UV-B irradiation. Our results highlight for the first time that a rationally engineered fungal insecticide can compete with a chemical counterpart to combat insect pests at an affordable cost and with low ecological risk. PMID:23956386

  20. Thiamethoxam resistance selected in the western flower thrips Frankliniella occidentalis (Thysanoptera: Thripidae): cross-resistance patterns, possible biochemical mechanisms and fitness costs analysis.

    PubMed

    Gao, Cong-Fen; Ma, Shao-Zhi; Shan, Cai-Hui; Wu, Shun-Fan

    2014-09-01

    The western flower thrips (WFT) Frankliniella occidentalis (Pergande) (Thysanoptera: Thripidae), an important pest of various crops in the world, has invaded China since 2003. To understand the risks and to determine possible mechanisms of resistance to thiamethoxam in WFT, a resistant strain was selected under the laboratory conditions. Cross-resistance and the possible biochemical resistance mechanisms were investigated in this study. A 15.1-fold thiamethoxam-resistant WFT strain (TH-R) was established after selection for 55 generations. Compared with the susceptible strain (TH-S), the selected TH-R strain showed extremely high level cross-resistance to imidaclothiz (392.1-fold) and low level cross-resistance to dinotefuran (5.7-fold), acetamiprid (2.9-fold) and emamectin benzoate (2.1-fold), respectively. No cross-resistance to other fourteen insecticides was detected. Synergism tests showed that piperonyl butoxide (PBO) and triphenyl phosphate (TPP) produced a high synergism of thiamethoxam effects in the TH-R strain (2.6- and 2.6-fold respectively). However, diethyl maleate (DEM) did not act synergistically with thiamethoxam. Biochemical assays showed that mixed function oxidase (MFO) activities and carboxylesterase (CarE) activity of the TH-R strain were 2.8- and 1.5-fold higher than that of the TH-S strain, respectively. When compared with the TH-S strain, the TH-R strain had a relative fitness of 0.64. The results show that WFT develops resistance to thiamethoxam after continuous application and thiamethoxam resistance had considerable fitness costs in the WFT. It appears that enhanced metabolism mediated by cytochrome P450 monooxygenases and CarE was a major mechanism for thiamethoxam resistance in the WFT. The use of cross-resistance insecticides, including imidaclothiz and dinotefuran, should be avoided for sustainable resistance management.

  1. Tri-Trophic Insecticidal Effects of African Plants against Cabbage Pests

    PubMed Central

    Amoabeng, Blankson W.; Gurr, Geoff M.; Gitau, Catherine W.; Nicol, Helen I.; Stevenson, Phil C.

    2013-01-01

    Botanical insecticides are increasingly attracting research attention as they offer novel modes of action that may provide effective control of pests that have already developed resistance to conventional insecticides. They potentially offer cost-effective pest control to smallholder farmers in developing countries if highly active extracts can be prepared simply from readily available plants. Field cage and open field experiments were conducted to evaluate the insecticidal potential of nine common Ghanaian plants: goat weed, Ageratum conyzoides (Asteraceae), Siam weed, Chromolaena odorata (Asteraceae), Cinderella weed, Synedrella nodiflora (Asteraceae), chili pepper, Capsicum frutescens (Solanaceae), tobacco, Nicotiana tabacum (Solanaceae) cassia, Cassia sophera (Leguminosae), physic nut, Jatropha curcas (Euphorbiaceae), castor oil plant, Ricinus communis (Euphorbiaceae) and basil, Ocimum gratissimum (Lamiaceae). In field cage experiments, simple detergent and water extracts of all botanical treatments gave control of cabbage aphid, Brevicoryne brassicae and diamondback moth, Plutella xylostella, equivalent to the synthetic insecticide Attack® (emamectin benzoate) and superior to water or detergent solution. In open field experiments in the major and minor rainy seasons using a sub-set of plant extracts (A. conyzoides, C. odorata, S. nodiflora, N. tabacum and R. communis), all controlled B. brassicae and P. xylostella more effectively than water control and comparably with or better than Attack®. Botanical and water control treatments were more benign to third trophic level predators than Attack®. Effects cascaded to the first trophic level with all botanical treatments giving cabbage head weights, comparable to Attack® in the minor season. In the major season, R. communis and A conyzoides treatment gave lower head yields than Attack® but the remaining botanicals were equivalent or superior to this synthetic insecticide. Simply-prepared extracts from readily

  2. A fungal insecticide engineered for fast per os killing of caterpillars has high field efficacy and safety in full-season control of cabbage insect pests.

    PubMed

    Liu, Yong-Jie; Liu, Jing; Ying, Sheng-Hua; Liu, Shu-Sheng; Feng, Ming-Guang

    2013-10-01

    Fungal insecticides developed from filamentous pathogens of insects are notorious for their slow killing action through cuticle penetration, depressing commercial interest and practical application. Genetic engineering may accelerate their killing action but cause ecological risk. Here we show that a Beauveria bassiana formulation, HV8 (BbHV8), engineered for fast per os killing of caterpillars by an insect midgut-acting toxin (Vip3Aa1) overexpressed in conidia has both high field efficacy and safety in full-season protection of cabbage from the damage of an insect pest complex dominated by Pieris rapae larvae, followed by Plutella xylostella larvae and aphids. In two fields repeatedly sprayed during summer, BbHV8 resulted in overall mean efficacies of killing of 71% and 75%, which were similar or close to the 70% and 83% efficacies achieved by commercially recommended emamectin benzoate but much higher than the 31% and 48% efficacies achieved by the same formulation of the parental wild-type strain (WT). Both BbHV8 and WT sprays exerted no adverse effect on a nontarget spider community during the trials, and the sprays did not influence saprophytic fungi in soil samples taken from the field plots during 4 months after the last spray. Strikingly, BbHV8 and the WT showed low fitness when they were released into the environment because both were decreasingly recovered from the field lacking native B. bassiana strains (undetectable 5 months after the spray), and the recovered isolates became much less tolerant to high temperature and UV-B irradiation. Our results highlight for the first time that a rationally engineered fungal insecticide can compete with a chemical counterpart to combat insect pests at an affordable cost and with low ecological risk.

  3. The application of co-melt-extruded poly(ε-caprolactone) as a controlled release drug delivery device when combined with novel bioactive drug candidates: Membrane permeation and Hanson dissolution studies

    PubMed Central

    Gardyne, Stephen J.; Mucalo, Michael R.; Rathbone, Michael J.

    2011-01-01

    Eight bioactive drug compounds (abamectin, amoxicillin, dexamethasone, dexamethasone valerate, ketoprofen, melatonin, oestradiol 17β, and oestradiol benzoate) were combined via melt extrusion and disc pressing processes with a polycaprolactone (PCL) matrix and were then evaluated and compared via membrane diffusion and Hanson dissolution studies. This investigation was to determine the potential of this matrix to act as a controlled release drug delivery vehicle for a number of drugs not previously combined with PCL in a melt extrusion mix. The inclusion of the progesterone/PCL system, for which the drug release behaviour has been well studied before was intended for comparison with the PCL systems incorporating drugs that have received little research attention in the past. Initial studies centred on an evaluation of the permeation ability of the bioactive drugs dissolved in aqueous cyclodextrin solutions through a poly(ε-caprolactone) (PCL) membrane using Valia-Chien side-by-side cells. Permeation rates were mostly low and found to range from 0 to 122 μg h−1 with only ketoprofen, melatonin, and progesterone displaying rates exceeding 20 μg h−1. Hanson dissolution release profiles in aqueous alcohol were subsequently measured for the 9 melt extruded PCL/drug combinations and led to Hanson release rates of 0–556 μg cm−2 h−0.5 with dexamethasone, dexamethasone valerate, ketoprofen, melatonin, and progesterone giving values exceeding 100 μg cm−2 h−0.5. A number of drugs such as the dexamethasones probably performed better than they did in the permeability rate measurements because of the less polar aqueous alcoholic solvent used. In searching for useful correlations between the drug physicochemical properties and release rate, only a moderate correlation (R2=0.5675) between Hanson dissolution release rate and permeation rate was found. This suggests that the release rate and the permeation are both controlled by the rate of drug

  4. Concerted Proton-Electron Transfer in a Ruthenium Terpyridyl-Benzoate System with a Large Separation between the Redox and Basic Sites

    PubMed Central

    Manner, Virginia W.; Mayer, James M.

    2009-01-01

    In order to understand how the separation between the electron and proton-accepting sites affects proton-coupled electron transfer (PCET) reactivity, we have prepared ruthenium complexes with 4′-(4-carboxyphenyl)terpyridine ligands, and studied reactivity with hydrogen atom donors (H-X). RuII(pydic)(tpy-PhCOOH) (RuIIPhCOOH), was synthesized in one pot from [(p-cymene)RuCl2]2, sodium 4′-(4-carboxyphenyl)-2,2′:6′,2″-terpyridine ([Na+]tpy-PhCOO−), and disodium pyridine-2,6-dicarboxylate (Na2pydic). RuIIPhCOOH plus nBu4NOH in DMF yields the deprotonated Ru(II) complex, nBu4N[RuII(pydic)(tpy-PhCOO)] (RuIIPhCOO−). The Ru(III) complex (RuIIIPhCOO) has been isolated by one-electron oxidation of RuIIPhCOO− with triarylaminium radical cations (NAr3•+). The bond dissociation free energy (BDFE) of the O–H bond in RuIIPhCOOH is calculated from pKa and E1/2 measurements as 87 kcal mol-1, making RuIIIPhCOO a strong hydrogen atom acceptor. There are 10 bonds and ca. 11.2 Å separating the metal from the carboxylate basic site in RuIIIPhCOO. Even with this separation, RuIIIPhCOO oxidizes the hydrogen atom donor TEMPOH (BDFE = 66.5 kcal mol-1, ΔG°rxn = -21 kcal mol-1) by removal of an electron and a proton to form RuIIPhCOOH and TEMPO radical in a concerted proton-electron transfer (CPET) process. The second order rate constant for this reaction is (1.1 ± 0.1) × 105 M-1 s-1 with kH/kD = 2.1 ± 0.2, similar to the observed kinetics in an analogous system without the phenyl spacer, RuIII(pydic)(tpy-COO) (RuIIICOO−). In contrast, hydrogen transfer from 2,6-di-tert-butyl-p-methoxyphenol [tBu2(OMe)ArOH] to RuIIIPhCOO is several orders of magnitude slower than the analogous reaction with RuIIICOO. PMID:19569636

  5. Comparison of the crystal structures of methyl 4-bromo-2-(meth-oxy-meth-oxy)benzoate and 4-bromo-3-(meth-oxy-meth-oxy)benzoic acid.

    PubMed

    Suchetan, P A; Suneetha, V; Naveen, S; Lokanath, N K; Krishna Murthy, P

    2016-04-01

    The title compounds, C10H11BrO4, (I), and C9H9BrO4, (II), are derivatives of bromo-hy-droxy-benzoic acids. Compound (II) crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In both (I) and (II), the O-CH2-O-CH3 side chain is not in its fully extended conformation; the O-C-O-C torsion angle is 67.3 (3) ° in (I), and -65.8 (3) and -74.1 (3)° in mol-ecules A and B, respectively, in compound (II). In the crystal of (I), mol-ecules are linked by C-H⋯O hydrogen bonds, forming C(5) chains along [010]. The chains are linked by short Br⋯O contacts [3.047 (2) Å], forming sheets parallel to the bc plane. The sheets are linked via C-H⋯π inter-actions, forming a three-dimensional architecture. In the crystal of (II), mol-ecules A and B are linked to form R 2 (2)(8) dimers via two strong O-H⋯O hydrogen bonds. These dimers are linked into ⋯A-B⋯A-B⋯A-B⋯ [C 2 (2)(15)] chains along [011] by C-H⋯O hydrogen bonds. The chains are linked by slipped parallel π-π inter-actions [inter-centroid distances = 3.6787 (18) and 3.8431 (17) Å], leading to the formation of slabs parallel to the bc plane.

  6. NEONATAL LOW- AND HIGH-DOSE EXPOSURE TO ESTRADIOL BENZOATE IN THE MALE RAT: II. EFFECTS ON MALE PUBERTY AND THE REPRODUCTIVE TRACT. (R826129)

    EPA Science Inventory

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  7. NEONATAL LOW- AND HIGH-DOSE EXPOSURE TO ESTRADIOL BENZOATE IN THE MALE RAT: I. EFFECTS ON THE PROSTATE GLAND. (R826129)

    EPA Science Inventory

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  8. DFT studies of calcium(II), strontium(II) and barium(II) benzoates with N,N,N‧,N‧-Tetrakis(2-hydroxyethyl/propyl)ethylenediamine

    NASA Astrophysics Data System (ADS)

    Obrai, Sangeeta; Kumar, Rakesh; Goyal, Milli; Kaushal, Svati

    2016-06-01

    The computational study of some s-block metal nitrobenzoateate complexes: [Ca(THEEN)(H2O)]2+ (1), [Ca(THPEN)(H2O)2]2+ (2), [Sr(THPEN)(H2O)3]2+ (3), [Ba(THPEN)(H2O)2]22+(4), [Ba(THEEN)(H2O)2]22+ (5), (where THEEN (N,N,N‧,N'-Tetrakis(2-hydroxyethyl)ethylenediamine) and THPEN (N,N,N‧,N'- Tetrakis(2-hydroxypropyl)ethylenediamine) are tetrapodal ligands) is presented here using density functional theory (DFT) in its hybrid form B3LYP. The geometries of the title complexes are described by the quantum-chemical approach using input coordinates obtained from the previously synthesized and X-ray characterized diffraction data of [Ca(THEEN)(H2O)](DNB)2.H2O, [Ca(THPEN)(H2O)2](DNB)2.H2O [Sr(THPEN)(H2O)3](DNB)2, [Ba(THPEN)(H2O)2]2(DNB)4.2H2O and [Ba(THEEN)(H2O)2]2(ONB)4 (where DNB- is 3,5-dinitrobenzoate anion and ONB- is 2-nitrobenzoate). Only the primary coordination sphere of complexes (1) - (5) is optimized in the gaseous state. The calculation of energy gaps of frontier orbitals (HOMO-LUMO), 13C -NMR shifts and vibrational bands is carried out using B3LYP/6-31G**/LANL2DZ level of theory. The calculated geometric and spectral parameters reproduced the experimental data with well-agreement. HOMO-LUMO energy gap suggest that [Ca(THPEN)(H2O)2]2+ (2) is the most stable (HLG = 6.893 eV) among all the similar previously and presently reported complexes.

  9. 4-Carb­oxy­pyridin-1-ium 2,4,5-tri­carb­oxy­benzoate monohydrate

    PubMed Central

    Arman, Hadi D.; Tiekink, Edward R. T.

    2013-01-01

    The title hydrated salt, C6H6NO2 +·C10H5O8 −·H2O, was isolated from the 1:1 cocrystallization of benzene-1,2,4,5-tetra­carb­oxy­lic acid and isonicotinic acid in ethanol solution. In the crystal, the cation is close to planar [r.m.s. deviation = 0.085 Å for the nine fitted atoms; the C—C—C—O(carbon­yl) torsion angle = −8.7 (4)°], but twists are evident in the anion, with all but the carb­oxy­lic acid group diagonally opposite the carboxyl­ate group being significantly twisted out of the plane of the benzene ring [C—C—C—O(carbon­yl) torsion angles = −118.1 (2), −157.6 (2), 4.3 (3) and 77.3 (3)°]. In the crystal, the ions and water mol­ecules are consolidated into a three-dimensional architecture by O—H⋯O and N—H⋯O hydrogen bonding along with C—H⋯O inter­actions. PMID:24046677

  10. Crystal stucture of methyl 2-({[2-(meth­oxy­carbon­yl)phen­yl]carbamo­yl}amino)­benzoate

    PubMed Central

    Yassine, Hasna; Khouili, Mostafa; El Ammari, Lahcen; Saadi, Mohamed; Ketatni, El Mostafa

    2015-01-01

    In the title compound, C17H16N2O5, the dihedral angles between the central urea [N—C(=O)—N] fragment and its attached benzene rings are 20.20 (14) and 24.24 (13)°; the dihedral angle between the aromatic rings is 42.1 (1)°. The mol­ecular conformation is consolidated by two intra­molecular N—H⋯O hydrogen bonds, which both generate S(6) rings. In the crystal, inversion dimers linked by pairs of C—H⋯O inter­actions generate R 2 2(14) loops. The dimers are linked by further C—H⋯O inter­actions into (011) sheets. PMID:25995913

  11. Crystal structure of trans-bis-(di-ethano-lamine-κ(3) O,N,O')manganese(II) bis-(3-amino-benzoate).

    PubMed

    Ibragimov, Aziz B; Zakirov, Bakhtiyar S; Ashurov, Jamshid M

    2016-04-01

    Reaction of m-amino-benzoic acid (MABA), di-ethano-lamine (DEA) and MnCl2·4H2O led to the formation of the title salt, [Mn(C4H11NO2)2](C7H6NO2)2. In the complex cation, the Mn(2+) ion is located on an inversion centre and is coordinated by two symmetry-related tridentate DEA mol-ecules, leading to the formation of a slightly distorted MnN2O4 octa-hedron. The MABA(-) counter-anions are connected to the complex ion by a pair of rather strong O-H⋯O hydrogen bonds, yielding a 1:2 supra-molecular aggregate. Much weaker N-H⋯O hydrogen bonds connect neighbouring aggregates into a three-dimensional network structure.

  12. Application of sequential expanded granular sludge bed reactors for biodegradation of acetate, benzoate, terephtalate and p-toluate in purified terephtalic acid production wastewater.

    PubMed

    Lee, Y S; Han, G B

    2016-01-01

    The anaerobic degradation of four major constituents from purified terephtalic acid production wastewater in sequential two expanded granular sludge bed (EGSB) reactors was studied. The performance of the system was evaluated in terms of chemical oxygen demand (COD) removal efficiencies, methane production, stability, granular sludge adaptability as well as reversion of bacterial inhibition. With volumetric loading rates of 1.9-25 kg-COD m(-3) d(-1) and terephtalate and p-toluate of 584-821 mg L(-1), average removal efficiencies of 97.6% and 75.2% were achieved in the EGSB reactors, respectively. In these conditions, gas production reached a total methane production rate of 0.33 L g-COD(-1) in the two-stage EGSB reactor system. The disturbance of the EGSB reactors was observed at a feed concentration above around 6.9 g-COD L(-1) because of higher influent COD concentration compared to other experiments.

  13. Diethylamino hydroxybenzoyl hexyl benzoate (DHHB) as additive to the UV filter avobenzone in cosmetic sunscreen formulations - Evaluation of the photochemical behavior and photostabilizing effect.

    PubMed

    Kawakami, Camila Martins; Máximo, Leandro Nériton Cândido; Fontanezi, Bianca Bueno; da Silva, Roberto Santana; Gaspar, Lorena Rigo

    2017-03-01

    The aim of the present study was to investigate the photochemical behavior of DHHB and its photostabilizing effect on avobenzone (AVO) in different sunscreen formulations. The formulations were subjected to photostability studies by HPLC and spectrophotometry. In vitro phototoxicity was assessed using 3T3 fibroblast cultures. The mechanism of interaction between DHHB and AVO was investigated by steady state and time-resolved fluorescence spectroscopy. All formulations provided ultra-protection against UVA radiation. HPLC results demonstrated that DHHB did not present a photostabilizing effect on AVO. Fluorescence spectroscopy showed that AVO and DHHB interact by a static quenching mechanism and DHHB did not affect the AVO excited state lifetime. In addition, the energy transfer by Förster mechanism (FRET), which is the most often mechanism responsible for singlet-singlet quenching, is unlikely in this work. These results suggest why DHHB did not work as a photostabilizer on AVO singlet excited state. Phototoxicity results demonstrated that combinations containing DHHB (C2) did not show a phototoxic potential. Finally, although DHHB was considered to be photostable for all formulations studied (F2 and F3) it did not increase the photostability of AVO (F3). Thus, we suggested that formulations containing DHHB (F2) should be considered more advantageous than formulations containing AVO and AVO/DHHB (F1 and F3 respectively).

  14. Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures1[W][OA

    PubMed Central

    Gaid, Mariam M.; Sircar, Debabrata; Müller, Andreas; Beuerle, Till; Liu, Benye; Ernst, Ludger; Hänsch, Robert; Beerhues, Ludger

    2012-01-01

    Although a number of plant natural products are derived from benzoic acid, the biosynthesis of this structurally simple precursor is poorly understood. Hypericum calycinum cell cultures accumulate a benzoic acid-derived xanthone phytoalexin, hyperxanthone E, in response to elicitor treatment. Using a subtracted complementary DNA (cDNA) library and sequence information about conserved coenzyme A (CoA) ligase motifs, a cDNA encoding cinnamate:CoA ligase (CNL) was isolated. This enzyme channels metabolic flux from the general phenylpropanoid pathway into benzenoid metabolism. HcCNL preferred cinnamic acid as a substrate but failed to activate benzoic acid. Enzyme activity was strictly dependent on the presence of Mg2+ and K+ at optimum concentrations of 2.5 and 100 mm, respectively. Coordinated increases in the Phe ammonia-lyase and HcCNL transcript levels preceded the accumulation of hyperxanthone E in cell cultures of H. calycinum after the addition of the elicitor. HcCNL contained a carboxyl-terminal type 1 peroxisomal targeting signal made up by the tripeptide Ser-Arg-Leu, which directed an amino-terminal reporter fusion to the peroxisomes. Masking the targeting signal by carboxyl-terminal reporter fusion led to cytoplasmic localization. A phylogenetic tree consisted of two evolutionarily distinct clusters. One cluster was formed by CoA ligases related to benzenoid metabolism, including HcCNL. The other cluster comprised 4-coumarate:CoA ligases from spermatophytes, ferns, and mosses, indicating divergence of the two clades prior to the divergence of the higher plant lineages. PMID:22992510

  15. Study on growth, structural, optical, thermal and mechanical properties of organic single crystal ethyl p-amino benzoate (EPAB) grown using vertical Bridgman technique

    NASA Astrophysics Data System (ADS)

    Muthuraja, A.; Kalainathan, S.

    2017-02-01

    Ethyl p-aminobenzoate (EPAB) single crystal was grown using vertical Bridgman technique (VBT). The crystal system of grown crystal was identified, and lattice parameters have been measured from the powder X-ray diffraction (PXRD). The optical transparency of EPAB single crystal was 55%, and the cut-off wavelength was found to be 337 nm. The thermal stability of EPAB single crystal was analyzed by thermogravimetric analysis. Etching studie were carried out for the grown crystal using different solvents, and etch pit density (EPD) was calculated and compared. Vickers microhardness (Hv) measurements revealed that EPAB belongs to the category of soft material. The dielectric studies reveal that the dielectric constant and dielectric loss of grown crystal decreases with increasing frequency for various temperatures. The third-order nonlinear optical property of EPAB was investigated and compared with other organic crystals. The evaluation of third-order optical properties such as nonlinear refractive index (n2), nonlinear absorption (β) and third-order nonlinear susceptibility (χ3) have found to be in the range of 10-11 m2/W, 10-4 m/W and 10-5 esu respectively. The Laser damage threshold energy of EPAB was measured using Nd: YAG laser. The blue emission of the grown crystal was identified by photoluminescence (PL) spectra measurements. The second harmonic generation (SHG) for the grown EPAB crystal was confirmed by Kurtz powder technique.

  16. Benzoylation of Ergosterol through Nucleophilic Acyl Substitution and Subsequent Formation of Ergosterol Benzoate Endoperoxide by Reaction with Singlet Oxygen Generated by Photosensitization

    ERIC Educational Resources Information Center

    Roslaniec, Mary C.; Sanford, Elizabeth M.

    2011-01-01

    Reactive oxygen species such as singlet oxygen have been a major focus of research in medicine. The effect of singlet oxygen on sterols within biological membranes is becoming increasingly more important. Ergosterol, a vitamin D precursor, is one such sterol. The benzoylation of ergosterol and subsequent reaction with singlet oxygen to form an…

  17. Crystal structure of 8-hy­droxy­quinolin­ium 2-carboxy-6-nitro­benzoate mono­hydrate

    PubMed Central

    Divya Bharathi, M.; Ahila, G.; Mohana, J.; Chakkaravarthi, G.; Anbalagan, G.

    2015-01-01

    In the title hydrated salt, C9H8NO+·C8H4NO6 −·H2O, the deprotonated carboxyl­ate group is almost normal to its attached benzene ring [dihedral angle = 83.56 (8)°], whereas the protonated carboxyl­ate group is close to parallel [dihedral angle = 24.56 (9)°]. In the crystal, the components are linked by N—H⋯O and O—H⋯O hydrogen bonds, generating [001] chains. The packing is consolidated by C—H⋯O and π–π [centroid-to-centroid distances = 3.6408 (9) and 3.6507 (9) Å] inter­actions, which result in a three-dimensional network. PMID:26029446

  18. Crystal structures of 1,4-di-aza-bicyclo-[2.2.2]octan-1-ium 4-nitro-benzoate dihydrate and 1,4-di-aza-bicyclo-[2.2.2]octane-1,4-diium bis-(4-nitro-benzoate): the influence of solvent upon the stoichiometry of the formed salt.

    PubMed

    Akhmad Aznan, Aina Mardia; Abdullah, Zanariah; Tiekink, Edward R T

    2014-07-01

    The 1:1 co-crystallization of 1,4-di-aza-bicyclo-[2.2.2]octane (DABCO) with 4-nitro-benzoic acid in ethanol-water (3/1) gave the salt dihydrate C6H13N2 (+)·C7H4NO4 (-)·2H2O, (1), whereas from methanol, the salt C6H14N2 (2+)·2C7H4NO4 (-), (2), was isolated. In (1), the cation and anion are linked by a strong N-H⋯O hydrogen bond, and the carboxyl-ate anion is close to planar [dihedral angle between terminal residues = 6.83 (9)°]. In (2), a three-ion aggregate is assembled by two N-H⋯O hydrogen bonds, and the carboxyl-ate anions are again close to planar [dihedral angles between terminal residues = 1.7 (3) and 5.9 (3)°]. Through the inter-vention of solvent water mol-ecules, which self-assemble into helical supra-molecular chains along the b axis, the three-dimensional architecture in (1) is stabilized by water-DABCO O-H⋯N and water-carboxyl-ate O-H⋯O hydrogen bonds, with additional stability afforded by C-H⋯O inter-actions. The global crystal structure comprises alternating layers of water mol-ecules and ion pairs stacked along the c axis. In the crystal of (2), the three-ion aggregates are assembled into a three-dimensional architecture by a large number of methyl-ene-carboxyl-ate/nitro C-H⋯O inter-actions as well as π-π contacts between inversion-related benzene rings [inter-centroid distances = 3.5644 (16) and 3.6527 (16) Å]. The cations and anions assemble into alternating layers along the c axis.

  19. [Effects of insecticides on insect pest-natural enemy community in early rice fields].

    PubMed

    Jiang, Junqi; Miao, Yong; Zou, Yunding; Li, Guiting

    2006-05-01

    This paper studied the effects of triazophos, shachongshuang, abamectin, and Bt + imidacloprid on the insect pest-natural enemy community in early rice fields in the Yangtze-Huaihe region of Anhui Province. The results showed that all of the test insecticides had significant effects in controlling the growth of major insect pest populations. The average value of insect pest-natural enemy community diversity under effects of triazophos, shachongshuang, abamectin, and Bt + imidacloprid was 1.545, 1.562, 1.691 and 1.915, respectively, while that in control plot was 1.897. After two weeks of applying insecticides, the plots applied with shachongshuang and abamectin had a similar composition of insect pest-natural enemy community, but the community composition was significantly different between the plots applied with triazophos and Bt + imidacloprid. From the viewpoints of community stability and pest control, Bt + imidacloprid had the best effect, and shachongshuang and abamectin were better than triazophos.

  20. Stage-Specific Expression of Resistance to Different Acaricides in Four Field Populations of Tetranychus urticae (Acari: Tetranychidae).

    PubMed

    Tang, Xiaofeng; Zhang, Youjun; Wu, Qingjun; Xie, Wen; Wang, Shaoli

    2014-10-01

    The two-spotted spider mite, Tetranychus urticae Koch, is a worldwide crop pest. The resistance to commonly applied acaricides (in this report, "acaricide" refers to both acaricides and insecticides that are toxic to mites) has seriously impaired T. urticae control in the field. Here, the sensitivity of eggs, larvae, and adults of laboratory and field populations of T. urticae to various acaricides was investigated. Based on data obtained with an acaricide-sensitive laboratory strain collected in 2009, abamectin was the most toxic of the tested acaricides. For each acaricide, susceptibility was greatest for larvae, least for adults, and intermediate for eggs. The egg was the most sensitive stage to abamectin, bifenazate, and hexythiazox; the larva was the most sensitive stage to abamectin, hexythiazox, bifenazate, propargite, and chlorfenapyr; and the adult was the most sensitive stage to abamectin, bifenazate, and chlorfenapyr. Based on the results obtained with the acaricide-sensitive laboratory strain, acaricides were selected to test against eggs, larvae, and adults of four field populations of T. urticae from Beijing, China. Although the field populations differed in their resistance to the acaricides in laboratory bioassays, the eggs, larvae, and adults of the four populations were sensitive to bifenazate and highly resistant to abamectin. Field trials for control of T. urticae in Beijing, China, should be conducted with bifenazate and other acaricides rather than with abamectin.

  1. 78 FR 14636 - Food Ingredients and Sources of Radiation Listed and Approved for Use in the Production of Meat...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2013-03-07

    ... amending the Federal meat and poultry products inspection regulations to remove sodium benzoate, sodium... document (77 FR 26706). FSIS proposed to remove sodium benzoate, sodium propionate, and benzoic acid from... phydroxybenzoate), calcium propionate, sodium propionate, benzoic acid, and sodium benzoate. In 2006, Kraft...

  2. Comparison of the crystal structures of methyl 4-bromo-2-(meth­oxy­meth­oxy)benzoate and 4-bromo-3-(meth­oxy­meth­oxy)benzoic acid

    PubMed Central

    Suchetan, P. A.; Suneetha, V.; Naveen, S.; Lokanath, N. K.; Krishna Murthy, P.

    2016-01-01

    The title compounds, C10H11BrO4, (I), and C9H9BrO4, (II), are derivatives of bromo–hy­droxy–benzoic acids. Compound (II) crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In both (I) and (II), the O—CH2—O—CH3 side chain is not in its fully extended conformation; the O—C—O—C torsion angle is 67.3 (3) ° in (I), and −65.8 (3) and −74.1 (3)° in mol­ecules A and B, respectively, in compound (II). In the crystal of (I), mol­ecules are linked by C—H⋯O hydrogen bonds, forming C(5) chains along [010]. The chains are linked by short Br⋯O contacts [3.047 (2) Å], forming sheets parallel to the bc plane. The sheets are linked via C—H⋯π inter­actions, forming a three-dimensional architecture. In the crystal of (II), mol­ecules A and B are linked to form R 2 2(8) dimers via two strong O—H⋯O hydrogen bonds. These dimers are linked into ⋯A–B⋯A–B⋯A–B⋯ [C 2 2(15)] chains along [011] by C—H⋯O hydrogen bonds. The chains are linked by slipped parallel π–π inter­actions [inter-centroid distances = 3.6787 (18) and 3.8431 (17) Å], leading to the formation of slabs parallel to the bc plane. PMID:27375868

  3. A Novel Pan-Negative-Gating Modulator of KCa2/3 Channels, Fluoro-Di-Benzoate, RA-2, Inhibits Endothelium-Derived Hyperpolarization–Type Relaxation in Coronary Artery and Produces Bradycardia In Vivo

    PubMed Central

    Oliván-Viguera, Aida; Valero, Marta Sofía; Coleman, Nicole; Brown, Brandon M.; Laría, Celia; Divina Murillo, María; Gálvez, José A.; Díaz-de-Villegas, María D.; Wulff, Heike; Badorrey, Ramón

    2015-01-01

    Small/intermediate conductance KCa channels (KCa2/3) are Ca2+/calmodulin regulated K+ channels that produce membrane hyperpolarization and shape neurologic, epithelial, cardiovascular, and immunologic functions. Moreover, they emerged as therapeutic targets to treat cardiovascular disease, chronic inflammation, and some cancers. Here, we aimed to generate a new pharmacophore for negative-gating modulation of KCa2/3 channels. We synthesized a series of mono- and dibenzoates and identified three dibenzoates [1,3-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate) (RA-2), 1,2-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate), and 1,4-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate)] with inhibitory efficacy as determined by patch clamp. Among them, RA-2 was the most drug-like and inhibited human KCa3.1 with an IC50 of 17 nM and all three human KCa2 subtypes with similar potencies. RA-2 at 100 nM right-shifted the KCa3.1 concentration-response curve for Ca2+ activation. The positive-gating modulator naphtho[1,2-d]thiazol-2-ylamine (SKA-31) reversed channel inhibition at nanomolar RA-2 concentrations. RA-2 had no considerable blocking effects on distantly related large-conductance KCa1.1, Kv1.2/1.3, Kv7.4, hERG, or inwardly rectifying K+ channels. In isometric myography on porcine coronary arteries, RA-2 inhibited bradykinin-induced endothelium-derived hyperpolarization (EDH)–type relaxation in U46619-precontracted rings. Blood pressure telemetry in mice showed that intraperitoneal application of RA-2 (≤100 mg/kg) did not increase blood pressure or cause gross behavioral deficits. However, RA-2 decreased heart rate by ≈145 beats per minute, which was not seen in KCa3.1−/− mice. In conclusion, we identified the KCa2/3–negative-gating modulator, RA-2, as a new pharmacophore with nanomolar potency. RA-2 may be of use to generate structurally new types of negative-gating modulators that could help to define the physiologic and pathomechanistic roles of KCa2/3 in the vasculature, central nervous system, and during inflammation in vivo. PMID:25468883

  4. A novel pan-negative-gating modulator of KCa2/3 channels, fluoro-di-benzoate, RA-2, inhibits endothelium-derived hyperpolarization-type relaxation in coronary artery and produces bradycardia in vivo.

    PubMed

    Oliván-Viguera, Aida; Valero, Marta Sofía; Coleman, Nicole; Brown, Brandon M; Laría, Celia; Murillo, María Divina; Gálvez, José A; Díaz-de-Villegas, María D; Wulff, Heike; Badorrey, Ramón; Köhler, Ralf

    2015-02-01

    Small/intermediate conductance KCa channels (KCa2/3) are Ca(2+)/calmodulin regulated K(+) channels that produce membrane hyperpolarization and shape neurologic, epithelial, cardiovascular, and immunologic functions. Moreover, they emerged as therapeutic targets to treat cardiovascular disease, chronic inflammation, and some cancers. Here, we aimed to generate a new pharmacophore for negative-gating modulation of KCa2/3 channels. We synthesized a series of mono- and dibenzoates and identified three dibenzoates [1,3-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate) (RA-2), 1,2-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate), and 1,4-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate)] with inhibitory efficacy as determined by patch clamp. Among them, RA-2 was the most drug-like and inhibited human KCa3.1 with an IC50 of 17 nM and all three human KCa2 subtypes with similar potencies. RA-2 at 100 nM right-shifted the KCa3.1 concentration-response curve for Ca(2+) activation. The positive-gating modulator naphtho[1,2-d]thiazol-2-ylamine (SKA-31) reversed channel inhibition at nanomolar RA-2 concentrations. RA-2 had no considerable blocking effects on distantly related large-conductance KCa1.1, Kv1.2/1.3, Kv7.4, hERG, or inwardly rectifying K(+) channels. In isometric myography on porcine coronary arteries, RA-2 inhibited bradykinin-induced endothelium-derived hyperpolarization (EDH)-type relaxation in U46619-precontracted rings. Blood pressure telemetry in mice showed that intraperitoneal application of RA-2 (≤100 mg/kg) did not increase blood pressure or cause gross behavioral deficits. However, RA-2 decreased heart rate by ≈145 beats per minute, which was not seen in KCa3.1(-/-) mice. In conclusion, we identified the KCa2/3-negative-gating modulator, RA-2, as a new pharmacophore with nanomolar potency. RA-2 may be of use to generate structurally new types of negative-gating modulators that could help to define the physiologic and pathomechanistic roles of KCa2/3 in the vasculature, central nervous system, and during inflammation in vivo.

  5. New mu(4)-oxido-bridged copper benzoate quasi-tetrahedron and bis-mu(3)-hydroxido-bridged copper azide and copper thiocyanate stepped cubanes: core conversion, structural diversity, and magnetic properties.

    PubMed

    Sarkar, Mrinal; Clérac, Rodolphe; Mathonière, Corine; Hearns, Nigel G R; Bertolasi, Valerio; Ray, Debashis

    2010-07-19

    [Cu(2)(mu(4)-O)Cu(2)] and [Cu(2)(mu(3)-OH)(2)Cu(2)] geometrical arrangements are found in a new family of tetranuclear complexes: [Cu(4)(mu(4)-O)(mu-bip)(2)(mu-O(2)CPh)(4)].0.5CH(2)Cl(2) (1.0.5CH(2)Cl(2)), [Cu(4)(mu(3)-OH)(2)(mu-bip)(2)(N(3))(4)] (2), and [Cu(4)(mu(3)-OH)(2)(mu-bip)(2)(NCS)(4)(DMF)(2)] (3.2DMF) [Hbip = 2,6-bis(benzyliminomethyl)-4-methylphenol; DMF = dimethylformamide]. These complexes have been characterized by X-ray crystallography, and their magnetic properties have been studied. Complex 1 reacts with azide and thiocyanate anions, leading to 2 and 3 with a change of the [Cu(4)(mu(4)-O)] core into [Cu(4)(mu(3)-OH)(2)] units. These compounds are new examples of [Cu(4)] complexes where Cu(II) ions are connected by two types of water-derived ligands: oxide and hydroxide. Formation of these [Cu(4)] complexes can be controlled by changing the bridging ligands, which allows an effective tuning of the self-assembly. The study of the magnetic properties reveals that these complexes exhibit strong intramolecular antiferromagnetic interactions to yield a S(T) = 0 ground state. For the three complexes, the temperature dependence of the magnetic susceptibility was fitted using a model with two isolated S = 1/2 dimers based on the H = -2J{S(Cu,1).S(Cu,2)} spin Hamiltonian with J/k(B) = -289 K for 1; J/k(B) = -464 and -405 K for 2 and 3, respectively (where J is the exchange constant through the oxido-phenoxido or hydroxido-phenoxido bridges, respectively).

  6. (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl benzoate

    PubMed Central

    Oubabi, Radouane; Auhmani, Aziz; Ait Itto, My Youssef; Auhmani, Abdelwahed; Daran, Jean-Claude

    2014-01-01

    The title compound, C27H34O2, was hemisynthesized through direct benzoyl­ation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. The S,S chirality of the mol­ecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter. PMID:25249914

  7. Methyl 4-{[6-(4-bromo­phen­yl)-3-oxo-2,3,4,5-tetra­hydro­pyridazin-4-yl]methyl}benzoate

    PubMed Central

    Bortoluzzi, Adailton J.; Souza, Luciana B. P.; Joussef, Antônio C.; Meyer, Emerson

    2011-01-01

    The structure of the title compound, C19H17BrN2O3, consists of two cyclic groups, viz. 4-(meth­oxy­carbon­yl)phenyl and 6-(4-bromo­phen­yl)-3-oxo-2,3,4,5-dihydro­pyridazin-4-yl, which are linked by a methyl­ene spacer. The pyridazine ring is twisted and the dihedral angle between its mean plane and that of the bromo­phenyl mean plane is 17.2 (2)°. The 4-(meth­oxy­carbon­yl)phenyl group shows a quasi-planar conformation, where the dihedral angle between the mean planes of the phenyl ring and carboxyl­ate ester group is 7.9 (4)°. Centrosymmetric inter­molecular N—H⋯O hydrogen bonds form dimers. These are linked by C—Br⋯O=C inter­actions [Br⋯O = 3.10 (1) Å] to form a one-dimensional polymeric structure running along the [10] direction. PMID:21754527

  8. FT-IR Study of CO2 Adsorption in a Dynamic Copper(II) Benzoate-Pyrazine Host with CO2-CO2 Interactions in the Adsorbed State

    SciTech Connect

    Kauffman, Kristi L.; Culp, Jeffrey T.; Goodman, Angela; Matranga, Christopher

    2011-02-10

    A detailed correlation is presented between the in situ Fourier transform-infrared (FT-IR) spectra of adsorbed CO2, CuBzPyz host bands, and CO2 adsorption sites using previously reported crystal structures of CO2- loaded CuBzPyz and CO2 adsorption. isotherms. Through the analysis of both in situ attenuated total reflectance FT-IR spectra taken at several points on the high pressure isotherm and in situ transmission FT-IR spectra acquired at low pressures and cryogenic temperatures, we provide additional insight into the pore-filling mechanism of CO2 on the structurally dynamic CuBzPyz host. The FT-IR spectrum of adsorbed CO2 shows distinct v2 and v3 spectral features that can be attributed to known CO2 adsorption sites observed in the reported crystal structure of the CO2-saturated phase of CuBzPyz. The availability of detailed high quality CO2-loaded structural data for CuBzPyz makes this system a case study for associating infrared spectral features with CO2 adsorption sites and should prove valuable for future interpretations of CO2 host-guest and guest-guest interactions when X-ray quality structural data is unavailable.

  9. Laboratory evaluation of insecticide-treated sugar baits for control of phlebotomine sand flies (Diptera: Psychodidae).

    PubMed

    Mascari, T M; Foil, L D

    2010-12-01

    The purpose of this study was to evaluate the use of boric acid, imidacloprid, ivermectin, or abamectin incorporated into sugar baits as oral toxicants for adult phlebotomine sand flies. Variable toxicity of insecticide-sugar bait solutions to adult male and female sand flies was demonstrated, based on male female median lethal concentration values of 0.10-0.08, 6.13-9.53, and 9.03-18.11 mg/liter of imidacloprid, ivermectin, and abamectin, respectively. Complete control of sand flies could not be achieved with as high as 40 g/liter of boric acid in sugar bait solution; concentrations >40 g/liter were found repellent to the sand flies. Uranine O (a fluorescent tracer dye that can be used to measure the ingestion of sugar baits by sand flies) did not interact negatively with imidacloprid, ivermectin, or abamectin when it was combined with the insecticides in a sugar bait. Also, incorporation of imidacloprid, ivermectin, or abamectin into sugar baits did not reduce the effect whether adult male and female sand flies fed on these sugar baits. We propose that imidacloprid, ivermectin, or abamectin could be used to control adult sand fly populations with targeted use of insecticide-treated sugar baits.

  10. Knockdown mortality, repellency, and residual effects of insecticides for control of adult Bactericera cockerelli (Hemiptera: Psyllidae).

    PubMed

    Gharalari, A H; Nansen, C; Lawson, D S; Gilley, J; Munyaneza, J E; Vaughn, K

    2009-06-01

    The psyllid Bactericera cockerelli (Sulc) (Hemiptera: Psyllidae) is the vector of a bacterial pathogen causing zebra chip (ZC) disease in potato, Solanum tuberosum L. (Solanaceae). Recently, ZC has become important to potato growers and the potato chipping industry in the southwestern United States, Mexico, Central America, and New Zealand. In the current study, we evaluated the knockdown effect of 12 insecticides against adult B. cockerelli, and we examined the effects of treating potato leaves: top side only, bottom side only, or both sides. Within 48 h of exposure, abamectin showed the highest and most consistent rate of adult B. cockerelli mortality and a dosage response to three dosages within labeled field rates. Choice tests conducted in petri dishes, involving untreated potato leaves and leaves treated with abamectin, revealed that abamectin did not affect host preference of adult B. cockerelli. A residual test under field conditions revealed that, although highly effective immediately after application, abamectin-effect was nonsignificantly different from control treatments 24 and 48 h after field application. Higher adult B. cockerelli mortality was recorded from potato plants treated with ground application compared with aerial 48 h after application. Our results indicated that abamectin has a high knockdown effect on adult B. cockerelli and that it can be used effectively in insecticide rotation programs against adult B. cockerelli and ZC control in potatoes.

  11. Toxicity of insecticides to the sweetpotato whitefly (Hemiptera: Aleyrodidae) and its natural enemies.

    PubMed

    Bacci, Leandro; Crespo, André L B; Galvan, Tederson L; Pereira, Eliseu J G; Picanço, Marcelo C; Silva, Gerson A; Chediak, Mateus

    2007-07-01

    Efficient chemical control is achieved when insecticides are active against insect pests and safe to natural enemies. In this study, the toxicity of 17 insecticides to the sweetpotato whitefly, Bemisia tabaci (Gennadius), and the selectivity of seven insecticides to natural enemies of this insect pest were evaluated. To determine the insecticide toxicity, B. tabaci adults were exposed to abamectin, acephate, acetamiprid, cartap, imidacloprid, malathion, methamidophos, bifenthrin, cypermethrin, deltamethrin, esfenvalerate, fenitrothion, fenpropathrin, fenthion, phenthoate, permethrin and trichlorphon at 50 and 100% of the field rate (FR), and to water (untreated control). To determine the insecticide selectivity, adults of Encarsia sp., Acanthinus sp., Discodon sp. and Lasiochilus sp. were exposed to abamectin, acephate, acetamiprid, cartap, imidacloprid, malathion and methamidophos at 50 and 100% FR, and to water. Groups of each insect species were exposed to kale leaves preimmersed in each treatment under laboratory conditions. Mortality of exposed individuals was recorded 24 h after treatment. Cartap and imidacloprid at 50 and 100% FR and abamectin and acetamiprid at 100% FR showed insecticidal activity to B. tabaci adults. Abamectin at 50 and 100% FR was the least insecticidal compound to the natural enemies Acanthinus sp., Discodon sp. and Lasiochilus sp. The present results suggest that abamectin at 100% FR may decrease B. tabaci field populations but can still be harmless to predators. Implications of these results within an integrated pest management context are discussed.

  12. Juvenile and sublethal effects of selected pesticides on the leafminer parasitoids Hemiptarsenus varicornis and Diglyphus isaea (Hymenoptera: Eulophidae) from Australia.

    PubMed

    Bjorksten, Tracey A; Robinson, Michelle

    2005-12-01

    The pest leafminers Liriomyza huidobrensis (Blanchard), Liriomyza sativae (Blanchard), and Liriomyza trifolii (Burgess) (Diptera: Agromyzidae) have spread into South East Asia and Oceania, and they are likely to reach Australia in the near future. Two translaminar pesticides, cyromazine and abamectin, currently provide effective chemical control of these pests, but because parasitoids can play an important role in controlling and preventing leafminer outbreaks, understanding the impact of pesticides on leafminer parasitoids is vital. Here, we tested larval and pupal mortality and sublethal effects of abamectin, cyromazine, and the widely used fungicide mancozeb on two common Australian leafminer parasitoids, Hemiptarsenus varicornis (Girault) and Diglyphus isaea (Walker). Abamectin caused significant mortality to larvae and pupae of both parasitoid species but cyromazine and mancozeb did not. Progeny production and longevity of H. varicornis were not affected by adult exposure to cyromazine and mancozeb, nor did direct pupal exposure decrease number of progeny produced by either parasitoid. Mortality of H. varicornis females emerging from leaves treated with abamectin was high for up to 72 h after eclosion but those surviving beyond 72 h did not differ from control females in the number of progeny produced. Mancozeb did not influence leaf residence time or parasitism by H. varicornis females. Cyromazine and the fungicide mancozeb were concluded to be compatible with the parasitoids tested and suitable for integrated pest management of leafminers should outbreaks of pest species occur in Australia. Abamectin should be used with caution because it caused significant mortality in both parasitoids tested here.

  13. Effects of a Chenopodium-based botanical insecticide/acaricide on Orius insidiosus (Hemiptera: Anthocoridae) and Aphidius colemani (Hymenoptera: Braconidae).

    PubMed

    Bostanian, Noubar J; Akalach, Mohammed; Chiasson, Hélène

    2005-10-01

    UDA-245 is a Chenopodium-based natural insecticide. Forty-eight hours after treatment with this compound, Orius insidiosus (Say) and Aphidius colemani Viereck showed slight contact toxicity at 5 g AI liter(-1). There was no residual toxicity to A colemani. These two beneficials are currently used in commercial flower and vegetable greenhouses for the management of thrips, spider mites, aphids and small caterpillars. In contrast, abamectin and insecticidal soap were toxic by contact to both species. UDA-245 did not reduce the number of eggs laid by treated O insidiosus. The eclosion of these eggs was also not adversely affected by UDA-245. The other two insecticides, abamectin and insecticidal soap had no effect on the emergence of A colemani from treated aphid mummies. However, abamectin decreased the percentage of aphid parasitism by A colemani following a residual treatment. The LC50 for UDA-245 for the two beneficials is slightly over twice the recommended field dose.

  14. Energetics and kinetics of anaerobic aromatic and fatty acid degradation. Progress report, March 1992--June 1995

    SciTech Connect

    McInerney M.J.

    1995-06-23

    Factors affecting the rate and extent of benzoate degradation by anaerobic syntrophic consortia were studied. Cocultures of a syntrophic benzoate degrader, strain SB, with a hydrogen/formate-using sulfate reducer degraded benzoate to a threshold that depended on the amount of substrate and acetate present. The benzoate threshold was not a function of the inhibition of benzoate degradation capacity by acetate or the toxicity of the undissociated form of acetate. Rather, a critical or minimal Gibb`s free energy value may exist where thermodynamic constraints preclude further benzoate degradation. A sensitive assay to detect low formate concentrations was developed to measure the formate levels when the benzoate threshold was reached. We showed that increased acetate concentrations, even when hydrogen and formate levels are low, affects the extent of benzoate degradation, implicating the importance of interspecies acetate transfer. In addition to benzoate, various saturated and unsaturated fatty acids, 2-methylbutyrate, and methyl esters of fatty acids supported growth in coculture with a hydrogen-using partner. SB is the only syntrophic bacterium known to use both benzoate and fatty acids. Phylogenetic analysis showed that SB clustered with sulfate reducers in the delta subclass of the Proteobacteria. SB grew well in coculture with Desulfoarculus baarsii, a sulfate reducer that uses formate but not hydrogen. This unequivocally shows that SB can grow by interspecies formate transfer.

  15. Energetics and kinetics of anaerobic aromatic and fatty acid degradation. Final report

    SciTech Connect

    Michael J. McInerney

    1996-06-24

    The factors that affect the rate and extent of a model aromatic compound, benzoate, in methanogenic environments was studied. Benzoate is degraded to a threshold concentration below which no further substrate degradation occurs. The threshold concentration depended on the substrate concentration and the amount of acetate present. The threshold value was not a function of the kinetic ability of the organism or toxicity of the end products. Rather a minimal Gibb's free energy value may exist where thermodynamic constraints preclude further benzoate degradation. In addition, new bacterial species were isolated and described, that degrade benzoate or reduce iron, cobalt and other metals.

  16. 40 CFR 180.600 - Propoxycarbazone; tolerances for residues.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... combined residues of the herbicide propoxycarbazone methyl 2- amino]sulfonyl]benzoate and its metabolite....05 (2) Tolerances are established for residues of the herbicide propoxycarbazone methyl 2-...

  17. 40 CFR 180.600 - Propoxycarbazone; tolerances for residues

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... combined residues of the herbicide propoxycarbazone methyl 2- amino]sulfonyl]benzoate and its metabolite....05 (2) Tolerances are established for residues of the herbicide propoxycarbazone methyl 2-...

  18. 40 CFR 180.600 - Propoxycarbazone; tolerances for residues.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... combined residues of the herbicide propoxycarbazone methyl 2- amino]sulfonyl]benzoate and its metabolite....05 (2) Tolerances are established for residues of the herbicide propoxycarbazone methyl 2-...

  19. 40 CFR 180.600 - Propoxycarbazone; tolerances for residues

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... combined residues of the herbicide propoxycarbazone methyl 2- amino]sulfonyl]benzoate and its metabolite....05 (2) Tolerances are established for residues of the herbicide propoxycarbazone methyl 2-...

  20. 40 CFR 180.600 - Propoxycarbazone; tolerances for residues

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... combined residues of the herbicide propoxycarbazone methyl 2- amino]sulfonyl]benzoate and its metabolite....05 (2) Tolerances are established for residues of the herbicide propoxycarbazone methyl 2-...

  1. [Analysis of preservatives in cosmetics by gas chromatography].

    PubMed

    Liu, Gang; Zhao, Gang; Wang, Xiao-fang

    2002-05-01

    The wide bore capillary column HP-1701(15 m x 0.53 mm i.d. x 1.0 micron) has been used to analyze benzyl alcohol, methyl-p-hydroxy benzoate, ethyl-p-hydroxy benzoate, propyl-p-hydroxy benzoate, and butyl-p-hydroxy benzoate in cosmetics. The results showed that these preservatives could be separated with the capillary column completely and their peaks were not interfered with those of other components in cosmetics. The detection limits were 13 ng, 70 ng, 70 ng, 100 ng and 100 ng respectively and the linear range was 50 ng-500 ng.

  2. Three new multiflorane-type triterpenes from pumpkin (Cucurbita maxima) seeds.

    PubMed

    Kikuchi, Takashi; Takebayashi, Mika; Shinto, Mayumi; Yamada, Takeshi; Tanaka, Reiko

    2013-05-14

    Three new multiflorane-type triterpenes; 7a-methoxymultiflor-8-ene-3a,29-diol 3-acetate-29-benzoate (1), 7-oxomultiflor-8-ene-3a,29-diol 3-acetate-29-benzoate (2), and multiflora-7,9(11)-diene-3a,29-diol 3-p-hydroxybenzoate-29-benzoate (3), were isolated from seeds of Cucurbita maxima, along with three known compounds. Compound 3 and multiflora-7,9(11)-diene-3a-29-diol 3-benzoate (5) exhibited potent inhibitory effects on melanogenesis, with low cytotoxicities, and 2 exhibited single-digit micromolar cytotoxicity against HL-60 and P388 cells.

  3. Metabolism of aromatic compounds by Caulobacter crescentus

    SciTech Connect

    Chatterjee, D.K.; Bourquin, A.W.

    1987-05-01

    Cultures of Caulobacter crescentus were found to grow on a variety of aromatic compounds. Degradation of benzoate, p-hydroxybenzoate, and phenol was found to occur via ..beta..-ketoadipate. The induction of degradative enzymes such as benzoate 1,2-dioxygenase, the ring cleavage enzyme catechol 1,2-dioxygenase, and cis,cis-muconate lactonizing enzyme appeared similar to the control mechanism present in Pseudomonas spp. Both benzoate 1,2-dioxygenase and catechol 1,2-dioxygenase had stringent specificities, as revealed by their action toward substituted benzoates and substituted catechols, respectively.

  4. Changes in insecticide resistance of the rice striped stem borer (Lepidoptera: Crambidae).

    PubMed

    Su, Jianya; Zhang, Zhenzhen; Wu, Min; Gao, Congfen

    2014-02-01

    Application of insecticides is the most important method to control Chilo suppressalis (Walker) (Lepidoptera: Crambidae), and continuous use of individual insecticides has driven the rapid development of insecticide resistance in C. suppressalis during the past 30 yr. Monitoring insecticide resistance provides information essential for integrated pest management. Insecticide resistance of field populations to monosultap, triazophos, chlorpyrifos, and abamectin in China was examined in 2010 and 2011. The results indicated that the resistance levels of 14 field populations to four insecticides were significantly different. Four populations showed moderate resistance, and other populations possessed low-level resistance or were susceptible to monosultap. Nine populations displayed an extremely high or a high level of resistance to triazophos, whereas four populations were sensitive to this agent. Five populations exhibited a low level of resistance to abamectin, while the others remained sensitive. When compared with historical data, resistance to monosultap and triazophos decreased significantly, and the percentage of populations with high-level or extremely high-level resistance was obviously reduced. By contrast, the resistance to abamectin increased slightly. The increasing and decreasing resistance levels reported in this study highlight the different evolutionary patterns of insecticide resistance in C. suppressalis. An overreliance on one or two insecticides may promote rapid development of resistance. Slow development of resistance to abamectin, which was used mainly in mixtures with other insecticides, implies that the use of insecticide mixtures may be an effective method to delay the evolution of resistance to insecticides.

  5. Evaluation of selected acaricides against two-spotted spider mite (Acari: Tetranychidae) on greenhouse cotton using multispectral data

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Two-spotted spider mite (TSSM), Tetranychus urticae (Koch), is an early season pest of cotton in the mid-southern United States and causes reduction in yield, fiber quality and impaired seed germination. Objectives of this study were to investigate the efficacy of abamectin and spiromesifen with two...

  6. Spectral response of spider mite infested cotton: Mite density and miticide rate study

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Two-spotted spider mites are important pests in many agricultural systems. Spider mites (Acari: Tetranychidae) have been found to cause economic damage in corn, cotton, and sorghum. Adult glass vial bioassays indicate that Temprano™ (abamectin) is the most toxic technical miticide for adult two-spot...

  7. Resistance to Bacillus thuringiensis Mediated by an ABC Transporter Mutation Increases Susceptibility to Toxins from Other Bacteria in an Invasive Insect.

    PubMed

    Xiao, Yutao; Liu, Kaiyu; Zhang, Dandan; Gong, Lingling; He, Fei; Soberón, Mario; Bravo, Alejandra; Tabashnik, Bruce E; Wu, Kongming

    2016-02-01

    Evolution of pest resistance reduces the efficacy of insecticidal proteins from the gram-positive bacterium Bacillus thuringiensis (Bt) used widely in sprays and transgenic crops. Recent efforts to delay pest adaptation to Bt crops focus primarily on combinations of two or more Bt toxins that kill the same pest, but this approach is often compromised because resistance to one Bt toxin causes cross-resistance to others. Thus, integration of Bt toxins with alternative controls that do not exhibit such cross-resistance is urgently needed. The ideal scenario of negative cross-resistance, where selection for resistance to a Bt toxin increases susceptibility to alternative controls, has been elusive. Here we discovered that selection of the global crop pest, Helicoverpa armigera, for >1000-fold resistance to Bt toxin Cry1Ac increased susceptibility to abamectin and spineotram, insecticides derived from the soil bacteria Streptomyces avermitilis and Saccharopolyspora spinosa, respectively. Resistance to Cry1Ac did not affect susceptibility to the cyclodiene, organophospate, or pyrethroid insecticides tested. Whereas previous work demonstrated that the resistance to Cry1Ac in the strain analyzed here is conferred by a mutation disrupting an ATP-binding cassette protein named ABCC2, the new results show that increased susceptibility to abamectin is genetically linked with the same mutation. Moreover, RNAi silencing of HaABCC2 not only decreased susceptibility to Cry1Ac, it also increased susceptibility to abamectin. The mutation disrupting ABCC2 reduced removal of abamectin in live larvae and in transfected Hi5 cells. The results imply that negative cross-resistance occurs because the wild type ABCC2 protein plays a key role in conferring susceptibility to Cry1Ac and in decreasing susceptibility to abamectin. The negative cross-resistance between a Bt toxin and other bacterial insecticides reported here may facilitate more sustainable pest control.

  8. Resistance to Bacillus thuringiensis Mediated by an ABC Transporter Mutation Increases Susceptibility to Toxins from Other Bacteria in an Invasive Insect

    PubMed Central

    Zhang, Dandan; Gong, Lingling; He, Fei; Soberón, Mario; Bravo, Alejandra; Tabashnik, Bruce E.; Wu, Kongming

    2016-01-01

    Evolution of pest resistance reduces the efficacy of insecticidal proteins from the gram-positive bacterium Bacillus thuringiensis (Bt) used widely in sprays and transgenic crops. Recent efforts to delay pest adaptation to Bt crops focus primarily on combinations of two or more Bt toxins that kill the same pest, but this approach is often compromised because resistance to one Bt toxin causes cross-resistance to others. Thus, integration of Bt toxins with alternative controls that do not exhibit such cross-resistance is urgently needed. The ideal scenario of negative cross-resistance, where selection for resistance to a Bt toxin increases susceptibility to alternative controls, has been elusive. Here we discovered that selection of the global crop pest, Helicoverpa armigera, for >1000-fold resistance to Bt toxin Cry1Ac increased susceptibility to abamectin and spineotram, insecticides derived from the soil bacteria Streptomyces avermitilis and Saccharopolyspora spinosa, respectively. Resistance to Cry1Ac did not affect susceptibility to the cyclodiene, organophospate, or pyrethroid insecticides tested. Whereas previous work demonstrated that the resistance to Cry1Ac in the strain analyzed here is conferred by a mutation disrupting an ATP-binding cassette protein named ABCC2, the new results show that increased susceptibility to abamectin is genetically linked with the same mutation. Moreover, RNAi silencing of HaABCC2 not only decreased susceptibility to Cry1Ac, it also increased susceptibility to abamectin. The mutation disrupting ABCC2 reduced removal of abamectin in live larvae and in transfected Hi5 cells. The results imply that negative cross-resistance occurs because the wild type ABCC2 protein plays a key role in conferring susceptibility to Cry1Ac and in decreasing susceptibility to abamectin. The negative cross-resistance between a Bt toxin and other bacterial insecticides reported here may facilitate more sustainable pest control. PMID:26872031

  9. Toxicity of chemicals commonly used in Indonesian vegetable crops to Liriomyza huidobrensis populations and the Indonesian parasitoids Hemiptarsenus varicornis, Opius sp., and Gronotoma micromorpha, as well as the Australian parasitoids Hemiptarsenus varicornis and Diglyphus isaea.

    PubMed

    Prijono, Djoko; Robinson, Michelle; Rauf, Aunu; Bjorksten, Tracey; Hoffmann, Ary A

    2004-08-01

    Liriomyza huidobrensis (Blanchard) and Liriomyza sativae (Blanchard) are important pests of vegetable crops in Indonesia and are likely to spread to neighboring countries. Three pesticides (dimehypo, abamectin, and cyromazine) are currently used to control these pests, but there is little information on their effectiveness against field populations and on their impact on parasitoids controlling Liriomyza species. The toxicity of these chemicals to L. huidobrensis and three common parasitoids (Hemiptarsenus varicornis Gerault, Opius sp., and Gronotoma micromorpha Perkins) was therefore evaluated in Indonesia with mortality laboratory assays. All three chemicals were effective against larvae of three populations of L. huidobrensis with different histories of chemical exposure. Dimehypo caused mortality in adult Opius sp., G. micromorpha, and H. varicornis, whereas abamectin was toxic only at concentrations substantially higher than the field rate. Cyromazine did not influence survival of the parasitoids. A commonly used fungicide, mancozeb, had no impact on parasitoid mortality. Trials were repeated with a strain of H. varicornis from Australia and a different parasitoid (Diglyphus isaea) recently found in Australia. Neither parasitoid was influenced by mancozeb or cyromazine. Abamectin applied at field rates caused some mortality among the adults of both species, but was less toxic than chlorpyrifos. Abamectin produced lower LC50s against Australian H. varicornis than against Indonesian H. varicornis. These results suggest that cyromazine can be incorporated into Liriomyza control programs in Indonesia that conserve parasitoids, whereas dimehypo and abamectin need to be used cautiously. Local Australian parasitoids should help control L. huidobrensis as long as only cyromazine and nontoxic fungicides are applied.

  10. SIMULTANEOUS DTERMINATION OF CHROMATE AND AROMATIC HYDROCARBONS IN ENVIRONMENTAL SAMPLES BY CAPILLARY ELECTROPHORESIS

    EPA Science Inventory

    An analytical method was developed to determine simultaneously, the inorganic anion CrO2-4, and organic aromatic compounds including benzoate, 2-Cl-benzoate, phenol, m-cresol and o-/p-cresol by capillary electrophoresis (CE). Chromate and the aromatics were separated in a relativ...

  11. 77 FR 26706 - Food Ingredients and Sources of Radiation Listed and Approved for Use in the Production of Meat...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2012-05-07

    ... Inspection Service (FSIS) is proposing to remove sodium benzoate, sodium propionate, and benzoic acid from... potassium sorbate, propylparaben (propyl p- hydroxybenzoate), calcium propionate, sodium propionate, benzoic acid, and sodium benzoate. The regulations provide that these substances ``* * * may be used in or...

  12. Identification of the Geobacter metallireducens BamVW Two-Component System, Involved in Transcriptional Regulation of Aromatic Degradation▿

    PubMed Central

    Juárez, Javier F.; Zamarro, María Teresa; Barragán, María J. L.; Blázquez, Blas; Boll, Matthias; Kuntze, Kevin; García, José Luis; Díaz, Eduardo; Carmona, Manuel

    2010-01-01

    Regulation of aromatic degradation in obligate anaerobes was studied in the Fe(III)-respiring model organism Geobacter metallireducens GS-15. A two-component system and a σ54-dependent promoter were identified that are both involved in the regulation of the gene coding for benzoate-coenzyme A ligase, catalyzing the initial step of benzoate degradation. PMID:19915033

  13. Microbiological preservation of cucumbers for bulk storage by the use of acetic acid and food preservatives

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Microbial growth did not occur when cucumbers were preserved without a thermal process by storage in solutions containing acetic acid, sodium benzoate, and calcium chloride to maintain tissue firmness. The concentrations of acetic acid and sodium benzoate required to assure preservation were low en...

  14. The metabolism of aromatic compounds by Rhodopseudomonas palustris. A new, reductive, method of aromatic ring metabolism

    PubMed Central

    Dutton, P. L.; Evans, W. C.

    1969-01-01

    1. Rhodopseudomonas palustris grows both aerobically and photosynthetically on aromatic acids. p-Hydroxybenzoate and protocatechuate are able to support aerobic growth; these compounds are metabolized by the protocatechuate 4,5-oxygenase pathway. 2. The photoassimilation of benzoate and hydroxybenzoates and the effects of air and darkness on the photoassimilation of benzoate are described. 3. Evidence in conflict with the pathway previously proposed for the photometabolism of benzoate is discussed. 4. The photometabolism of benzoate is accomplished by a novel reductive pathway involving its reduction to cyclohex-1-ene-1-carboxylate, followed by hydration to 2-hydroxycyclohexanecarboxylate and after dehydrogenation to 2-oxocyclohexanecarboxylate further hydration results in ring-fission and the production of pimelate. 5. Attempts were made to prepare cell-free extracts capable of dissimilating benzoate. PMID:5807211

  15. Benzoic acid fermentation from starch and cellulose via a plant-like β-oxidation pathway in Streptomyces maritimus

    PubMed Central

    2012-01-01

    Background Benzoic acid is one of the most useful aromatic compounds. Despite its versatility and simple structure, benzoic acid production using microbes has not been reported previously. Streptomyces are aerobic, Gram-positive, mycelia-forming soil bacteria, and are known to produce various kinds of antibiotics composed of many aromatic residues. S. maritimus possess a complex amino acid modification pathway and can serve as a new platform microbe to produce aromatic building-block compounds. In this study, we carried out benzoate fermentation using S. maritimus. In order to enhance benzoate productivity using cellulose as the carbon source, we constructed endo-glucanase secreting S. maritimus. Results After 4 days of cultivation using glucose, cellobiose, or starch as a carbon source, the maximal level of benzoate reached 257, 337, and 460 mg/l, respectively. S. maritimus expressed β-glucosidase and high amylase-retaining activity compared to those of S. lividans and S. coelicolor. In addition, for effective benzoate production from cellulosic materials, we constructed endo-glucanase-secreting S. maritimus. This transformant efficiently degraded the phosphoric acid swollen cellulose (PASC) and then produced 125 mg/l benzoate. Conclusions Wild-type S. maritimus produce benzoate via a plant-like β-oxidation pathway and can assimilate various carbon sources for benzoate production. In order to encourage cellulose degradation and improve benzoate productivity from cellulose, we constructed endo-glucanase-secreting S. maritimus. Using this transformant, we also demonstrated the direct fermentation of benzoate from cellulose. To achieve further benzoate productivity, the L-phenylalanine availability needs to be improved in future. PMID:22545774

  16. 2-({[(Pyridin-1-ium-2-ylmeth­yl)carbamo­yl]form­amido}­meth­yl)pyridin-1-ium bis­(3,5-di­carb­oxy­benzoate): crystal structure and Hirshfeld surface analysis

    PubMed Central

    Jotani, Mukesh M.; Syed, Sabrina; Halim, Siti Nadiah Abdul; Tiekink, Edward R. T.

    2016-01-01

    The asymmetric unit of the title salt, C14H16N4O2 2+·2C9H5O6 −, comprises half a dication, being located about a centre of inversion, and one anion, in a general position. The central C4N2O2 group of atoms in the dication are almost planar (r.m.s. deviation = 0.009 Å), and the carbonyl groups lie in an anti disposition to enable the formation of intra­molecular amide-N—H⋯O(carbon­yl) hydrogen bonds. To a first approximation, the pyridinium and amide N atoms lie to the same side of the mol­ecule [Npy—C—C—Namide torsion angle = 34.8 (2)°], and the anti pyridinium rings are approximately perpendicular to the central part of the mol­ecule [dihedral angle = 68.21 (8)°]. In the anion, one carboxyl­ate group is almost coplanar with the ring to which it is connected [Cben—Cben—Cq—O torsion angle = 2.0 (3)°], whereas the other carboxyl­ate and carb­oxy­lic acid groups are twisted out of the plane [torsion angles = 16.4 (3) and 15.3 (3)°, respectively]. In the crystal, anions assemble into layers parallel to (10-4) via hy­droxy-O—H⋯O(carbon­yl) and charge-assisted hy­droxy-O—H⋯O(carboxyl­ate) hydrogen bonds. The dications are linked into supra­molecular tapes by amide-N—H⋯O(amide) hydrogen bonds, and thread through the voids in the anionic layers, being connected by charge-assisted pyridinium-N—O(carboxyl­ate) hydrogen bonds, so that a three-dimensional architecture ensues. An analysis of the Hirshfeld surface points to the importance of O—H⋯O hydrogen bonding in the crystal structure. PMID:26958398

  17. Crystal structure of tri-aqua-(1,10-phen-anthroline-κ(2) N,N')(2,4,5-tri-fluoro-3-meth-oxy-benzoato-κO (1))cobalt(II) 2,4,5-tri-fluoro-3-meth-oxy-benzoate.

    PubMed

    Sun, Junshan

    2014-11-01

    The title salt, [Co(C8H4F3O3)(C12H8N2)(H2O)3](C8H4F3O3), was obtained under solvothermal conditions by the reaction of 2,4,5-tri-fluoro-3-meth-oxy-benzoic acid with CoCl2 in the presence of 1,10-phenanthroline (phen). The Co(II) ion is octa-hedrally coordinated by two N atoms [Co-N = 2.165 (2) and 2.129 (2) Å] from the phen ligand, by one carboxyl-ate O atom [Co-O = 2.107 (1) Å] and by three O atoms from water mol-ecules [Co-O = 2.093 (1), 2.102 (1) and 2.114 (1) Å]. The equatorial positions of the slightly distorted octa-hedron are occupied by the N atoms, the carboxyl-ate O and one water O atom. An intra- and inter-molecular O-H⋯O hydrogen-bonding network between the water-containing complex cation and the organic anion leads to the formation of ribbons parallel to [010].

  18. Di-methyl-ammonium 2,4,5-tri-carb-oxy-benzoate: an example of the deca-rbonylation of N,N-di-methyl-formamide in the presence of a metal and a benzene-polycarb-oxy-lic acid. Is zirconium(IV) the Tsotsi?

    PubMed

    Hulushe, S T; Hosten, E C; Watkins, G M

    2016-11-01

    The title salt, C2H8N(+)·C10H5O8(-), was the unexpected product of an attempt to prepare a Zr(IV) metal-organic framework with benzene-1,2,4,5-tetra-carb-oxy-lic acid (1,2,4,5-H3B4C). In the reaction, the DMF solvent has been decarb-on-yl-ated, forming the di-methyl-ammonium cation, with one proton lost from the tetra-carb-oxy-lic acid. It is proposed that the Zr(IV) salt acts as a Tsotsi or robber, plundering CO from the DMF mol-ecule. The resulting salt crystallizes with two cations and two anions in the asymmetric unit. An intra-molecular hydrogen bond forms between a carb-oxy-lic acid substituent and the carboxyl-ate group of each of the monodeprotonated (1,2,4,5-H3B4C(-)) anions. In the crystal, an extensive array of O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds generates a three-dimensional network, with columns of cations and anions forming along the b axis.

  19. Di­methyl­ammonium 2,4,5-tri­carb­oxy­benzoate: an example of the deca­rbonylation of N,N-di­methyl­formamide in the presence of a metal and a benzene­polycarb­oxy­lic acid. Is zirconium(IV) the Tsotsi?

    PubMed Central

    Hulushe, S. T.; Hosten, E. C.; Watkins, G. M.

    2016-01-01

    The title salt, C2H8N+·C10H5O8 −, was the unexpected product of an attempt to prepare a ZrIV metal–organic framework with benzene-1,2,4,5-tetra­carb­oxy­lic acid (1,2,4,5-H3B4C). In the reaction, the DMF solvent has been decarb­on­yl­ated, forming the di­methyl­ammonium cation, with one proton lost from the tetra­carb­oxy­lic acid. It is proposed that the ZrIV salt acts as a Tsotsi or robber, plundering CO from the DMF mol­ecule. The resulting salt crystallizes with two cations and two anions in the asymmetric unit. An intra­molecular hydrogen bond forms between a carb­oxy­lic acid substituent and the carboxyl­ate group of each of the monodeprotonated (1,2,4,5-H3B4C−) anions. In the crystal, an extensive array of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds generates a three-dimensional network, with columns of cations and anions forming along the b axis. PMID:27840699

  20. Safety assessment of poloxamers 101, 105, 108, 122, 123, 124, 181, 182, 183, 184, 185, 188, 212, 215, 217, 231, 234, 235, 237, 238, 282, 284, 288, 331, 333, 334, 335, 338, 401, 402, 403, and 407, poloxamer 105 benzoate, and poloxamer 182 dibenzoate as used in cosmetics.

    PubMed

    Singh-Joy, Subhashni D; McLain, Valerie C

    2008-01-01

    Poloxamers are polyoxyethlyene, polyoxypropylene block polymers. The impurities of commercial grade Poloxamer 188, as an example, include low-molecular-weight substances (aldehydes and both formic and acetic acids), as well as 1,4-dioxane and residual ethylene oxide and propylene oxide. Most Poloxamers function in cosmetics as surfactants, emulsifying agents, cleansing agents, and/or solubilizing agents, and are used in 141 cosmetic products at concentrations from 0.005% to 20%. Poloxamers injected intravenously in animals are rapidly excreted in the urine, with some accumulation in lung, liver, brain, and kidney tissue. In humans, the plasma concentration of Poloxamer 188 (given intravenously) reached a maximum at 1 h, then reached a steady state. Poloxamers generally were ineffective in wound healing, but were effective in reducing postsurgical adhesions in several test systems. Poloxamers can cause hypercholesterolemia and hypertriglyceridemia in animals, but overall, they are relatively nontoxic to animals, with LD(50) values reported from 5 to 34.6 g/kg. Short-term intravenous doses up to 4 g/kg of Poloxamer 108 produced no change in body weights, but did result in diffuse hepatocellular vacuolization, renal tubular dilation in kidneys, and dose-dependent vacuolization of epithelial cells in the proximal convoluted tubules. A short-term inhalation toxicity study of Poloxamer 101 at 97 mg/m(3) identified slight alveolitis after 2 weeks of exposure, which subsided in the 2-week postexposure observation period. A short-term dermal toxicity study of Poloxamer 184 in rabbits at doses up to 1000 mg/kg produced slight erythema and slight intradermal inflammatory response on histological examination, but no dose-dependent body weight, hematology, blood chemistry, or organ weight changes. A 6-month feeding study in rats and dogs of Poloxamer 188 at exposures up to 5% in the diet produced no adverse effects. Likewise, Poloxamer 331 (tested up to 0.5 g/kg day(-1)), Poloxamer 235 (tested up to 1.0 g/kg day(-1)), and Poloxamer 338 (at 0.2 or 1.0 g/kg day(-1)) produced no adverse effects in dogs. Poloxamer 338 (at 5.0 g/kg day(-1)) produced slight transient diarrhea in dogs. Poloxamer 188 at levels up to 7.5% in diet given to rats in a 2-year feeding study produced diarrhea at 5% and 7.5% levels, a small decrease in growth at the 7.5% level, but no change in survival. Doses up to 0.5 mg/kg day(-1) for 2 years using rats produced yellow discoloration of the serum, high serum alkaline phosphatase activity, and elevated serum glutamicpyruvic transaminase and glutamic-oxalacetic transaminase activities. Poloxamers are minimal ocular irritants, but are not dermal irritants or sensitizers in animals. Data on reproductive and developmental toxicity of Poloxamers were not found. An Ames test did not identify any mutagenic activity of Poloxamer 407, with or without metabolic activation. Several studies have suggested anticarcinogenic effects of Poloxamers. Poloxamers appear to increase the sensitivity to anticancer drugs of multidrug-resistant cancer cells. In clinical testing, Poloxamer 188 increased the hydration of feces when used in combination with a bulk laxative treatment. Compared to controls, one study of angioplasty patients receiving Poloxamer 188 found a reduced myocardial infarct size and a reduced incidence of reinfarction, with no evidence of toxicity, but two other studies found no effect. Poloxamer 188 given to patients suffering from sickle cell disease had decreased pain and decreased hospitilization, compared to controls. Clinical tests of dermal irritation and sensitization were uniformly negative. The Cosmetic Ingredient Review (CIR) Expert Panel stressed that the cosmetic industry should continue to use the necessary purification procedures to keep the levels below established limits for ethylene oxide, propylene oxide, and 1,4-dioxane. The Panel did note the absence of reproductive and developmental toxicity data, but, based on molecular weight and solubility, there should be little skin penetration and any penetration of the skin should be slow. Also, the available data demonstrate that Poloxamers that are introduced into the body via routes other than dermal exposure have a rapid clearance from the body, suggesting that there would be no risk of reproductive and/or developmental toxicity. Overall, the available data do not suggest any concern about carcinogenesis. Although there are gaps in knowledge about product use, the overall information available on the types of products in which these ingredients are used, and at what concentration, indicates a pattern of use. Based on these safety test data and the information that the manufacturing process can be controlled to limit unwanted impurities, the Panel concluded that these Poloxamers are safe as used.

  1. Effects of sarcoptic mange and its control with oil of Cedrus deodara, Pongamia glabra, Jatropha curcas and benzyl benzoate, both with and without ascorbic acid on growing sheep: assessment of weight gain, liver function, nutrient digestibility, wool production and meat quality.

    PubMed

    Dimri, U; Sharma, M C

    2004-03-01

    The aim of this study was to evaluate the therapeutic efficacy of commonly used acaricidal drugs in India and also to assess the effect of ascorbic acid as adjunct therapy in 72 growing sheep with sarcoptic mange, aged 5-6 months and weighing 20.4-31.7 kg. Eight replicates of nine animals were formed based on sex, and day 0 body weight. Drugs were applied locally on the affected parts daily and recovery changes in skin lesions were observed at the time of every application. L-ascorbic acid was administered intramuscularly. Skin scrapings were collected daily from each group and examined for the presence of mites. Body weights were measured every 10th day from day 0 to 60. Nutrient digestiblity was evaluated by studying digestibility coefficients for dry matter, crude protein, ether extract, crude fibre, nitrogen free extract, total carbohydrates and nutrient balance (nitrogen, calcium and phosphorus) for a 30-day period. The liver function was evaluated by bromosulphophthalein (BSP) dye retention time. The animals were shorn on day 60 post-treatment (PT). Meat quality assesment was carried out by killing sheep at 60 days PT and estimating pH, water-holding capacity (WHC), tenderness, muscle colour, rib eye area and fat thickness. The lambs treated with oil of Jatropha curcas ascorbic acid had significantly (P < 0.05) greater mean daily body weight gains (63.29 g) than the infected untreated control (41.10 g). This was also higher than the mean daily weight gain in other treated groups. Infected untreated sheep showed significantly (P < 0.01) reduced digestibility coefficients for dry matter, crude protein, crude fibre, ether extract and total carbohydrate, but no significant differences for nitrogen-free extract. Treated sheep had significantly higher positive nitrogen, calcium and phosphorus balances compared with infested untreated sheep. Oil of J. curcas plus ascorbic acid (OJC-AA) treated group was better over all other treated groups with respect to nutrient digestibility. The BSP test revealed significant (P < 0.05) increase in BSP retention time in sheep with sarcoptic mange. Post -treatment, the BSP retention time decreased in all treated groups and the decrease was maximum in OJC-AA treated group. The carcasses of sheep treated with OJC-AA had significantly (P < 0.01) higher water holding capacity, rib eye area and back fat thickness than the untreated infected control group. The muscle pH and tenderness values were significantly lower in OJC-AA treated group post-slaughter than infested untreated control group. Muscle colour of OJC-AA treated group was maximum bright red. The lambs treated with OJC-AA had significantly (P < 0.05) greater clean fleece weight and fleece yield than the untreated infected group. It is concluded that OJC was the better therapy for sarcoptic mange of sheep and ascorbic acid as adjunct therapy is advisable. OJC-AA therapy may be better from the point of view of improving two most important production parameters in sheep, that is, wool yield and meat production.

  2. Determination of an ion exchange constant by the use of a kinetic probe: a new semiempirical kinetic approach involving the effects of 3-F- and 4-F-substituted benzoates on the rate of piperidinolysis of anionic phenyl salicylate in aqueous cationic micelles.

    PubMed

    Yusof, Nor Saadah M; Khan, M Niyaz

    2010-07-06

    Pseudo-first-order rate constants (k(obs)) for the nucleophilic substitution reaction of piperidine (Pip) with ionized phenyl salicylate (PS(-)), obtained at a constant [Pip](T) (= 0.1 M), [PS(-)](T) (= 2 x 10(-4) M), [CTABr](T) (cetyltrimethylammonium bromide), < or = 0.06 M NaOH, and a varying concentration of MX (= 3-FC(6)H(4)CO(2)Na, 3-FBzNa and 4-FC(6)H(4)CO(2)Na, 4-FBzNa), follow the kinetic relationship k(obs) = (k(0) + thetaK(X/S)[MX])/(1 + K(X/S)[MX]) which is derived by the use of the pseudophase micellar (PM) model coupled with an empirical equation. The empirical equation explains the effects of [MX] on CTABr micellar binding constant (K(S)) of PS(-) that occur through X(-)/PS(-) ion exchange. Empirical constants theta and K(X/S) give the parameters F(X/S) and K(X/S), respectively. The magnitude of F(X/S) gives the measure of the fraction of micellized PS(-) transferred to the aqueous phase by the limiting concentration of X(-) through X(-)/PS(-) ion exchange. The values of F(X/S) and K(X/S) have been used to determine the usual thermodynamic ion exchange constant (K(X)(Y)) for ion exchange process X(-)/Y(-) on the CTABr micellar surface. The values of K(X)(Br) (where Br = Y) have been calculated for X = 3-FBzNa and 4-FBzNa. The mean values of K(X)(Br) are 12.8 +/- 0.9 and 13.4 +/- 0.6 for X(-) = 3-FBz(-) and 4-FBz(-), respectively. Nearly 3-fold-larger values of K(X)(Br) for X = 3-FBz(-) and 4-FBz(-) than those for X = Bz(-), 2-ClBz(-), 2-CH(3)Bz(-), and the 2,6-dichlorobenzoate ion (2,6-Cl(2)Bz(-)) are attributed to the presence of wormlike micelles in the presence of > 50 mM 3-FBz(-) and 4-FBz(-) in the [CTABr](T) range of 5-15 mM. Rheological properties such as shear thinning behavior of plots of shear viscosity versus the shear rate at a constant [3-FBz(-)] or [4-FBz(-)] as well as shear viscosity (at a constant shear rate) maxima as a function of the concentrations of 3-FBz(-) and 4-FBz(-) support the conclusion, derived from the values of K(X)(Br), for the probable presence of wormlike/viscoelastic micellar solutions under the conditions of the present study.

  3. Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.

    PubMed

    Wu, T; Wang, C; Wang, X; Ma, Q

    2008-10-01

    An ultra performance liquid chromatography (UPLC) method has been developed for the simultaneous determination of 21 preservatives: 2-methyl-4-isothiazoline-3-ketone, bronopol, 5-chloro-2-methyl-4-isothiazoline-3-ketone, benzyl alcohol, 2-phenoxyethanol, methyl-p-hydroxy benzoate, ethyl-p-hydroxy benzoate, methyl benzoate, 4-hydroxybenzoic acid iso-propyl ester, propyl-p-hydroxy benzoate, 4-chloro-3-methylphenol, ethyl benzoate, 2-phenylphenol, 4-hydroxybenzoic acid iso-butyl ester, butyl-p-hydroxy benzoate, 4-chloro-3,5-dimethylphenol, phenyl benzoate, 2,4-dichloro-3,5-dimethylphenol, 2-benzyl-4-chlorophenol, triclocarban and triclosan in cosmetics. A Waters ACQUITY UPLC BEH C(18) column was used with 0.1% formic acid solution as the mobile phase under the condition of gradient elution. Preservatives were extracted with methanol by ultrasonicator, and then they were analysed by UPLC-PDA detector. All these preservatives were baseline separated in 8.5 min. The pre-treatment method of samples and the chromatographic condition of analysis were critically examined in this study. The recoveries ranged from 90.5 to 97.8%, with RSD values below 3.2%, and all correlation coefficients (r) were no less than 0.9997. Thus, this method could be used for analysing the preservatives in cosmetic products.

  4. Iridium-Catalysed ortho-Directed Deuterium Labelling of Aromatic Esters--An Experimental and Theoretical Study on Directing Group Chemoselectivity.

    PubMed

    Devlin, Jennifer; Kerr, William J; Lindsay, David M; McCabe, Timothy J D; Reid, Marc; Tuttle, Tell

    2015-06-25

    Herein we report a combined experimental and theoretical study on the deuterium labelling of benzoate ester derivatives, utilizing our developed iridium N-heterocyclic carbene/phosphine catalysts. A range of benzoate esters were screened, including derivatives with electron-donating and -withdrawing groups in the para- position. The substrate scope, in terms of the alkoxy group, was studied and the nature of the catalyst counter-ion was shown to have a profound effect on the efficiency of isotope exchange. Finally, the observed chemoselectivity was rationalized by rate studies and theoretical calculations, and this insight was applied to the selective labelling of benzoate esters bearing a second directing group.

  5. [Selection of isolates of entomopathogenic fungi for controlling Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae) and their compatibility with insecticides used in tomato crop].

    PubMed

    Pires, Lauricí M; Marques, Edmilson J; Oliveira, José V de; Alves, Sérgio B

    2010-01-01

    The activity of Metarhizium anisopliae and Beauveria bassiana towards eggs and larvae of Tuta absoluta (Meyrick) was evaluated. Our data showed that the isolates were pathogenic to both developmental stages tested and the eggs were more susceptible than the 1st instars. The isolates URPE-6 and URPE-19 of M. anisopliae were more pathogenic to eggs and larvae, respectively. The compatibility of these two isolates with the insecticides chlorfenapyr, spinosad, indoxacarb, abamectin, and neem were evaluated. Spinosad and indoxacarb were compatible with the two M. anisopliae isolates in all tested concentrations. At the average recommended concentration, chlorfenapyr was compatible to URPE-6 and abamectin to UFPE-19. The use of entomopathogenic fungi associated with compatible insecticides may be a useful alternative to control T. absoluta.

  6. Factors influencing dissipation of avermectins in sheep faeces.

    PubMed

    Virant Celestina, Tina; Kolar, Lucija; Gobec, Ivan; Kuzner, Jernej; Flajs, Vesna Cerkvenik; Pogacnik, Milan; Erzen, Nevenka Kozuh

    2010-01-01

    Factors influencing fate of avermectins (abamectin, doramectin) in faeces of treated sheep were investigated under different experimental conditions. In the laboratory, concentrations of both avermectins were declined in homogenised faeces of treated animals until day 14 of exposure, regardless of experimental conditions. After that day, no significant decrease in concentrations was observed till the end of the experiment. Established DT(50) did not exceed 9 days. In the karst pasture, an average DT(50) of 27 days was established for abamectin and 23 days for doramectin in natural faeces of treated sheep. In the compost mixture, doramectin concentration was decreased by 38.9+/-2.6% during 21 days of the thermophilic phase of composting. Therefore, DT(50) was not established. A possible influence of moisture content of sheep faeces on concentrations of avermectins was observed.

  7. Residue behaviour of six pesticides in button crimini during home canning.

    PubMed

    Du, Pengqiang; Liu, Xingang; Gu, Xiaojun; Dong, Fengshou; Xu, Jun; Kong, Zhiqiang; Li, Yuanbo; Zheng, Yongquan

    2014-01-01

    The effect of home canning (including washing, boiling, cooling, adding solution and sterilisation) on residue levels of imidacloprid, diflubenzuron, abamectin, pyriproxyfen and β-cypermethrin and chlorothalonilin on button crimini was assessed. Residues of imidacloprid, diflubenzuron, abamectin and pyriproxyfen were measured by UPLC-MS/MS; the residues of β-cypermethrin and chlorothalonil were measured by GC. Results showed that washing resulted in a 3.8% reduction of the initial residue level of imidacloprid (p ≤ 0.05). From washing to sterilisation the processing effect was significant compared with raw crimini (p ≤ 0.05), but processing through cooling and adding solution had no effect. For diflubenzuron, from raw crimini to sterilisation the processing effect was significant by comparison with the initial level (p ≤ 0.05); the processing effect was not obvious between two sequential steps, and the sequential steps have list: washing and boiling, boiling and cooling, boiling and adding of solution, cooling and adding solution. The changes in abamectin levels were also significant from raw crimini to sterilisation compared with raw crimini (p ≤ 0.05), but the changes were not obvious from boiling to adding solution and amongst them. For pyriproxyfen, washing resulted in a 39% reduction, but changes were not obvious from washing to sterilisation, p ≤ 0.05 between two consecutive steps. The whole procedure could significantly decrease residues of β-cypermethrin (p ≤ 0.05); washing could significantly reduce residues of β-cypermethrin; the effects of last procedures were complicated, and p ≤ 0.05 between two consecutive steps. Washing resulted in an 80% reduction of chlorothalonil; after washing there were no detectable residues. After the whole process, the processing factors for imidacloprid, diflubenzuron, abamectin, pyriproxyfen, β-cypermethrin and chlorothalonil were 0.40, 0.22, 0.04, 0.85, 0.28 and 0, respectively.

  8. Generation of Breast Cancer Stem Cells by the EMT

    DTIC Science & Technology

    2009-10-01

    non-CSCs. Strikingly, we found that salinomycin treatment reduced the representation of CSCs down to 0.2%, more than 300-fold decrease in the...relative representation of these cells in the cell population. In addition, we noted that salinomycin halted tumor growth in vivo and caused extensive...cells. In an initial proof-of-principle screen, we discovered two compounds – salinomycin and abamectin – that were characterized in detail. These

  9. Insecticide toxicity to oriental fruit fly Bactrocera dorsalis (Diptera: Tephritidae) is influenced by environmental factors.

    PubMed

    Lin, Yuying; Jin, Tao; Zeng, Ling; Lu, Yongyue

    2013-02-01

    In this study, we investigated the effects of environmental factors (temperature, dose, dietary source, and feeding density) on the insecticide tolerance of Bactrocera dorsalis (Hendel) (Diptera: Tephritidae). The results indicated that the toxicities of trichlorphon and abamectin to B. dorsalis increased with an increase in temperature. At 15-35 degrees C, the toxicity of beta-cypermethrin decreased with an increase in temperature at low doses (0.82 and 1.86 mg/L), but was similar at a high dose (4.18 mg/L). These results demonstrated that the temperature coefficient of beta-cypermethrin was related to both temperature and dosage. The insecticide sensitivity of B. dorsalis reared on different dietary sources was significantly different. Trichlorphon sensitivity of B. dorsalis fed on banana was the highest with an LC50 of 1.61 mg/L, followed by on apple, carambola, semiartificial diet, pear, mango, guava, orange, and papaya. With an increasing feeding density, the sensitivity of B. dorsalis adults to trichlorphon increased, while the sensitivities of B. dorsalis adults to abamectin and beta-cypermethrin decreased. The differences between LC50 values of insects reared at densities of 10 and 13 eggs/g of semiartificial diet to trichlorphon, abamectin and beta-cypermethrin were not significant. This result suggested that representative toxicity could be obtained by using adults developed at a feeding density between 10-13 eggs/g of semiartificial diet. Adult body weight was positively correlated with the LC50 value of trichlorphon, but was negatively correlated with the toxicities of abamectin and beta-cypermethrin. These results suggested that the effects of adult body weight on the toxicity of insecticides were different among different chemicals.

  10. Selectivity of pesticides used in integrated apple production to the lacewing, Chrysoperla externa.

    PubMed

    Moura, Alexandre Pinho; Carvalho, Geraldo Andrade; Moscardini, Valéria Fonseca; Lasmar, Olinto; Rezende, Denise Tourino; Marques, Márcio Candeias

    2010-01-01

    This research aimed to assess the toxicity of the pesticides abamectin 18 CE (0.02 g a.i. L-1), carbaryl 480 SC (1.73 g a.i. L-1), sulfur 800 GrDA (4.8 g a.i. L-1), fenitrothion 500 CE (0.75 g a.i. L-1), methidathion 400 CE (0.4 g a.i. L-1), and trichlorfon 500 SC (1.5 g a.i. L-1) as applied in integrated apple production in Brazil on the survival, oviposition capacity, and egg viability of the lacewing, Chrysoperla externa (Hagen) (Neuroptera: Chrysopidae) from Bento Gonçalves and Vacaria, Rio Grande do Sul State, Brazil. An attempt was made to study morphological changes caused by some of these chemicals, by means of ultrastructural analysis, using a scanning electronic microscope. Carbaryl, fenitrothion, and methidathion caused 100% adult mortality for both populations, avoiding evaluation of pesticides' effects on predator reproductive parameters. Abamectin and sulfur also affected the survival of these individuals with mortality rates of 10% and 6.7%, respectively, for adults from Bento Gonçalves, and were harmless to those from Vacaria at the end of evaluation. Trichlorfon was also harmless to adults from both populations. No compound reduced oviposition capacity. C. externa from Vacaria presented higher reproductive potential than those from Bento Gonçalves. In relation to egg viability, sulfur was the most damaging compound to both populations of C. externa. Ultrastructural analyses showed morphological changes in the micropyle and the chorion of eggs laid by C. externa treated with either abamectin or sulfur. The treatment may have influenced the fertilization of C. externa eggs and embryonic development. Sulfur was responsible for malformations in the end region of the abdomen and genitals of treated females. When applied to adults, abamectin, sulfur, and trichlorfon were harmless, while carbaryl, fenitrothion, and methidathion were harmful, according to the IOBC classification.

  11. Selectivity of Pesticides used in Integrated Apple Production to the Lacewing, Chrysoperla externa

    PubMed Central

    Moura, Alexandre Pinho; Carvalho, Geraldo Andrade; Moscardini, Valéria Fonseca; Lasmar, Olinto; Rezende, Denise Tourino; Marques, Márcio Candeias

    2010-01-01

    This research aimed to assess the toxicity of the pesticides abamectin 18 CE (0.02 g a.i. L-1), carbaryl 480 SC (1.73 g a.i. L-1), sulfur 800 GrDA (4.8 g a.i. L-1), fenitrothion 500 CE (0.75 g a.i. L-1), methidathion 400 CE (0.4 g a.i. L-1), and trichlorfon 500 SC (1.5 g a.i. L-1) as applied in integrated apple production in Brazil on the survival, oviposition capacity, and egg viability of the lacewing, Chrysoperla externa (Hagen) (Neuroptera: Chrysopidae) from Bento Gonçalves and Vacaria, Rio Grande do Sul State, Brazil. An attempt was made to study morphological changes caused by some of these chemicals, by means of ultrastructural analysis, using a scanning electronic microscope. Carbaryl, fenitrothion, and methidathion caused 100% adult mortality for both populations, avoiding evaluation of pesticides' effects on predator reproductive parameters. Abamectin and sulfur also affected the survival of these individuals with mortality rates of 10% and 6.7%, respectively, for adults from Bento Gonçalves, and were harmless to those from Vacaria at the end of evaluation. Trichlorfon was also harmless to adults from both populations. No compound reduced oviposition capacity. C. externa from Vacaria presented higher reproductive potential than those from Bento Gonçalves. In relation to egg viability, sulfur was the most damaging compound to both populations of C. externa. Ultrastructural analyses showed morphological changes in the micropyle and the chorion of eggs laid by C. externa treated with either abamectin or sulfur. The treatment may have influenced the fertilization of C. externa eggs and embryonic development. Sulfur was responsible for malformations in the end region of the abdomen and genitals of treated females. When applied to adults, abamectin, sulfur, and trichlorfon were harmless, while carbaryl, fenitrothion, and methidathion were harmful, according to the IOBC classification. PMID:20879916

  12. Identification and Functional Expression of a Glutamate- and Avermectin-Gated Chloride Channel from Caligus rogercresseyi, a Southern Hemisphere Sea Louse Affecting Farmed Fish

    PubMed Central

    Niemeyer, María Isabel; Marabolí, Vanessa; González-Nilo, F. Danilo; Teulon, Jacques; Sepúlveda, Francisco V.; Cid, L. Pablo

    2014-01-01

    Parasitic sea lice represent a major sanitary threat to marine salmonid aquaculture, an industry accounting for 7% of world fish production. Caligus rogercresseyi is the principal sea louse species infesting farmed salmon and trout in the southern hemisphere. Most effective control of Caligus has been obtained with macrocyclic lactones (MLs) ivermectin and emamectin. These drugs target glutamate-gated chloride channels (GluCl) and act as irreversible non-competitive agonists causing neuronal inhibition, paralysis and death of the parasite. Here we report the cloning of a full-length CrGluClα receptor from Caligus rogercresseyi. Expression in Xenopus oocytes and electrophysiological assays show that CrGluClα is activated by glutamate and mediates chloride currents blocked by the ligand-gated anion channel inhibitor picrotoxin. Both ivermectin and emamectin activate CrGluClα in the absence of glutamate. The effects are irreversible and occur with an EC50 value of around 200 nM, being cooperative (nH = 2) for ivermectin but not for emamectin. Using the three-dimensional structure of a GluClα from Caenorabditis elegans, the only available for any eukaryotic ligand-gated anion channel, we have constructed a homology model for CrGluClα. Docking and molecular dynamics calculations reveal the way in which ivermectin and emamectin interact with CrGluClα. Both drugs intercalate between transmembrane domains M1 and M3 of neighbouring subunits of a pentameric structure. The structure displays three H-bonds involved in this interaction, but despite similarity in structure only of two these are conserved from the C. elegans crystal binding site. Our data strongly suggest that CrGluClα is an important target for avermectins used in the treatment of sea louse infestation in farmed salmonids and open the way for ascertaining a possible mechanism of increasing resistance to MLs in aquaculture industry. Molecular modeling could help in the design of new, more efficient

  13. Residual bioassay to assess the toxicity of Acaricides against Aceria guerreronis (Acari: Eriophyidae) under laboratory conditions.

    PubMed

    Monteiro, Vaneska B; Lima, Debora B; Gondim, Manoel G C; Siqueira, Herbert A A

    2012-08-01

    Aceria guerreronis Keifer (Acari: Eriophyidae) is considered a major pest of the coconut (Cocos nucifera L.), and the use of pesticides is the current method to control it. However, no standard toxicological tests exist to select and assess the efficiency of molecules against the coconut mite. The aim of this study was to develop a methodology that allows for the evaluation of the relative toxicity of acaricides to A. guerreronis through rapid laboratory procedures. We confined A. guerreronis on arenas made out of coconut leaflets and tested two application methods: immersing the leaf fragments in acaricides and spraying acaricides on the leaf fragments under a Potter spray tower. In the latter application method, we sprayed leaf fragments both populated with and devoid of mites. We evaluated the comparative toxicity of two populations (Itamaracá and Petrolina, Pernambuco, Brazil) by spraying on leaflets without mites and submitted the mortality data to probit analysis after 24 h of exposure. No difference was observed in the LC50, regardless of whether the leaflets were immersed or sprayed with acaricide (abamectin, chlorfenapyr or fenpyroximate). The toxicity of chlorfenapyr and fenpyroximate did not differ, irrespective of whether it was applied directly to the leaflet or to the mite; however, the toxicity of abamectin was higher when applied directly to the mite. Chlorpyrifos and abamectin toxicities were lower for the Petrolina population than for the Itamaracá population. Immersing and spraying coconut leaflets can be used to assess the mortality of A. guerreronis under laboratory conditions.

  14. Toxicity and Residual Activity of Insecticides Against Tamarixia triozae (Hymenoptera: Eulophidae), a Parasitoid of Bactericera cockerelli (Hemiptera: Triozidae).

    PubMed

    Luna-Cruz, Alfonso; Rodríguez-Leyva, Esteban; Lomeli-Flores, J Refugio; Ortega-Arenas, Laura D; Bautista-Martínez, Néstor; Pineda, Samuel

    2015-10-01

    Bactericera cockerelli (Sulc) (Hemiptera: Triozidae) is one of the most economically important pests of potato, tomato, and peppers in Central America, Mexico, the United States, and New Zealand. Its control is based on the use of insecticides; however, recently, the potential of the eulophid parasitoid Tamarixia triozae (Burks) (Hymenoptera: Eulophidae) for population regulation has been studied. Because T. triozae is likely to be exposed to insecticides on crops, the objective of this study was to explore the compatibility of eight insecticides with this parasitoid. The toxicity and residual activity (persistence) of spirotetramat, spiromesifen, beta-cyfluthrin, pymetrozine, azadirachtin, imidacloprid, abamectin, and spinosad against T. triozae adults were assessed using a method based on the residual contact activity of each insecticide on tomato leaf discs collected from treated plants growing under greenhouse conditions. All eight insecticides were toxic to T. triozae. Following the classification of the International Organization of Biological Control, the most toxic were abamectin and spinosad, which could be placed in toxicity categories 3 and 4, respectively. The least toxic were azadirachtin, pymetrozine, spirotetramat, spiromesifen, imidacloprid, and beta-cyfluthrin, which could be placed in toxicity category 2. In terms of persistence, by day 5, 6, 9, 11, 13, 24, and 41 after application, spirotetramat, azadirachtin, spiromesifen, pymetrozine, imidacloprid, beta-cyfluthrin, abamectin, and spinosad could be considered harmless, that is, placed in toxicity category 1 (<25% mortality of adults). The toxicity and residual activity of some of these insecticides allow them to be considered within integrated pest management programs that include T. triozae.

  15. Physiological selectivity and activity reduction of insecticides by rainfall to predatory wasps of Tuta absoluta.

    PubMed

    Barros, Emerson C; Bacci, Leandro; Picanco, Marcelo C; Martins, Júlio C; Rosado, Jander F; Silva, Gerson A

    2015-01-01

    In this study, we carried out three bioassays with nine used insecticides in tomato crops to identify their efficiency against tomato leaf miner Tuta absoluta, the physiological selectivity and the activity reduction of insecticides by three rain regimes to predatory wasps Protonectarina sylveirae and Polybia scutellaris. We assessed the mortality caused by the recommended doses of abamectin, beta-cyfluthrin, cartap, chlorfenapyr, etofenprox, methamidophos, permethrin, phenthoate and spinosad to T. absoluta and wasps at the moment of application. In addition, we evaluated the wasp mortality due to the insecticides for 30 days on plants that did not receive rain and on plants that received 4 or 125 mm of rain. Spinosad, cartap, chlorfenapyr, phenthoate, abamectin and methamidophos caused mortality higher than 90% to T. absoluta, whereas the pyrethroids beta-cyfluthrin, etofenprox and permethrin caused mortality between 8.5% and 46.25%. At the moment of application, all the insecticides were highly toxic to the wasps, causing mortality higher than 80%. In the absence of rain, all the insecticides continued to cause high mortality to the wasps for 30 days after the application. The toxicity of spinosad and methamidophos on both wasp species; beta-cyfluthrin on P. sylveirae and chlorfenapyr and abamectin on P. scutellaris, decreased when the plants received 4 mm of rain. In contrast, the other insecticides only showed reduced toxicity on the wasps when the plants received 125 mm of rain.

  16. Molecular cloning and characterization of a P-glycoprotein from the diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae).

    PubMed

    Tian, Lixia; Yang, Jiaqiang; Hou, Wenjie; Xu, Baoyun; Xie, Wen; Wang, Shaoli; Zhang, Youjun; Zhou, Xuguo; Wu, Qingjun

    2013-11-20

    Macrocyclic lactones such as abamectin and ivermectin constitute an important class of broad-spectrum insecticides. Widespread resistance to synthetic insecticides, including abamectin and ivermectin, poses a serious threat to the management of diamondback moth, Plutella xylostella (L.) (Lepidoptera: Plutellidae), a major pest of cruciferous plants worldwide. P-glycoprotein (Pgp), a member of the ABC transporter superfamily, plays a crucial role in the removal of amphiphilic xenobiotics, suggesting a mechanism for drug resistance in target organisms. In this study, PxPgp1, a putative Pgp gene from P. xylostella, was cloned and characterized. The open reading frame (ORF) of PxPgp1 consists of 3774 nucleotides, which encodes a 1257-amino acid peptide. The deduced PxPgp1 protein possesses structural characteristics of a typical Pgp, and clusters within the insect ABCB1. PxPgp1 was expressed throughout all developmental stages, and showed the highest expression level in adult males. PxPgp1 was highly expressed in midgut, malpighian tubules and testes. Elevated expression of PxPgp1 was observed in P. xylostella strains after they were exposed to the abamectin treatment. In addition, the constitutive expressions of PxPgp1 were significantly higher in laboratory-selected and field-collected resistant strains in comparison to their susceptible counterpart.

  17. Relative Susceptibility of Phyllocnistis citrella (Lepidoptera: Gracillariidae) to Commonly Used Insecticides in Maharashtra, India.

    PubMed

    George, Anjitha; Rao, C N; Ghike, Sonali; Dhengre, Vijay

    2017-03-03

    Foliar application of insecticides has been the most commonly followed practice to manage Phyllocnistis citrella Stainton in nurseries and flush leaves in citrus groves. Leaf dip bioassays were conducted against insecticides, viz., acephate 75SP, dimethoate 30EC, abamectin 1.9EC, fenvalerate 20EC, imidacloprid 17.8SL, and thiamethoxam 25WG, and were tested against P. citrella larvae for their susceptibility. Among six insecticides tested on second-instar P. citrella larvae collected from Nagpur mandarin/acid lime cultivars during 2013-2016, abamectin was the most toxic insecticide for the initial year (LC50 values ranged from 20.99 to 49.00 ppm), while dimethoate (LC50 of 36.57-160.95 ppm) and thiamethoxam (39.90-71.96 ppm) were consistently effective against P. citrella larvae for the rest of the period. Resistance ratio (RR) values calculated based on the baseline susceptible culture, viz., abamectin (1.24-2.33), acephate (1.03-2.31), fenvalerate (1.54-3.45), dimethoate(1.28-5.63), imidacloprid (1.29-8.64), and thiamethoxam (1.05-1.80), indicated that the current RR values were in low levels (RR < 10).

  18. Sediment-associated pesticides in an urban stream in Guangzhou, China: implication of a shift in pesticide use patterns.

    PubMed

    Li, Huizhen; Sun, Baoquan; Lydy, Michael J; You, Jing

    2013-04-01

    Pesticide use patterns in China have changed in recent years; however, the study of the environmental fate of current-use pesticides (CUPs) and their ecotoxicological significance in aquatic ecosystems is limited. In the present study, sediments were collected from an urban stream in the Chinese city of Guangzhou. Sediment-associated legacy organochlorine pesticides and CUPs-including organophosphates, pyrethroids, fipronil, and abamectin-were analyzed. Additionally, the relative toxicity of the sediments was evaluated with 10-d bioassays using Chironomus dilutus. Fifteen of 16 sediments collected from the stream were acutely toxic to C. dilutus, with 81% of the samples causing 100% mortality. Abamectin, fipronil, and pyrethroids (mainly cypermethrin) were identified as the principal contributors to the noted toxicity in the midges, with median predicted toxic units of 1.63, 1.63, and 1.03, respectively. Sediments taken from downstream sites, where residential and industrial regions were located, had elevated CUP concentrations and sediment toxicity compared with upstream sites. The present study is the first of its kind to link sediment CUPs, fipronil, and abamectin concentrations with toxicity in urban streams in China with a focus on shifting pesticide usage patterns.

  19. Molecular Cloning and Characterization of a P-Glycoprotein from the Diamondback Moth, Plutella xylostella (Lepidoptera: Plutellidae)

    PubMed Central

    Tian, Lixia; Yang, Jiaqiang; Hou, Wenjie; Xu, Baoyun; Xie, Wen; Wang, Shaoli; Zhang, Youjun; Zhou, Xuguo; Wu, Qingjun

    2013-01-01

    Macrocyclic lactones such as abamectin and ivermectin constitute an important class of broad-spectrum insecticides. Widespread resistance to synthetic insecticides, including abamectin and ivermectin, poses a serious threat to the management of diamondback moth, Plutella xylostella (L.) (Lepidoptera: Plutellidae), a major pest of cruciferous plants worldwide. P-glycoprotein (Pgp), a member of the ABC transporter superfamily, plays a crucial role in the removal of amphiphilic xenobiotics, suggesting a mechanism for drug resistance in target organisms. In this study, PxPgp1, a putative Pgp gene from P. xylostella, was cloned and characterized. The open reading frame (ORF) of PxPgp1 consists of 3774 nucleotides, which encodes a 1257-amino acid peptide. The deduced PxPgp1 protein possesses structural characteristics of a typical Pgp, and clusters within the insect ABCB1. PxPgp1 was expressed throughout all developmental stages, and showed the highest expression level in adult males. PxPgp1 was highly expressed in midgut, malpighian tubules and testes. Elevated expression of PxPgp1 was observed in P. xylostella strains after they were exposed to the abamectin treatment. In addition, the constitutive expressions of PxPgp1 were significantly higher in laboratory-selected and field-collected resistant strains in comparison to their susceptible counterpart. PMID:24264038

  20. Energetics and kinetics of anaerobic aromatic and fatty acid degradation. Progress report, November 1992--November 1993

    SciTech Connect

    McInerney, M.J.

    1993-11-12

    The kinetics of benzoate degradation by the anaerobic syntrophic bacterium, Syntrophus buswellii, in coculture with different sulfate reducers was studied with sulfate or nitrate as the electron acceptor. A threshold value for benzoate degradation dependent on the acetate concentration was observed with sulfate, but not nitrate, as the electron acceptor. No threshold was observed in tricultures containing an acetate-using sulfate reducer. The addition of the acetate-using sulfate reducer to cocultures that had degraded benzoate to its threshold value resulted in further degradation of benzoate to levels below the analytical detection limit (ca. 200 nM). These data are consistent with a thermodynamic explanation for the threshold, and exclude the possibility that the threshold was the result of the inhibitory action of the undissociated form of acetate.

  1. 21 CFR 172.515 - Synthetic flavoring substances and adjuvants.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... appropriate section in this part. Acetal; acetaldehyde diethyl acetal. Acetaldehyde phenethyl propyl acetal.... Benzyl acetoacetate. Benzyl alcohol. Benzyl benzoate. Benzyl butyl ether. Benzyl butyrate. Benzyl... ethyl ether. Benzyl formate. 3-Benzyl-4-heptanone; benzyl dipropyl ketone. Benzyl isobutyrate....

  2. Determination of Aspartame, Caffeine, Saccharin, and Benzoic Acid in Beverages by High Performance Liquid Chromatography.

    ERIC Educational Resources Information Center

    Delaney, Michael F.; And Others

    1985-01-01

    Describes a simple and reliable new quantitative analysis experiment using liquid chromatography for the determinaiton of caffeine, saccharin, and sodium benzoate in beverages. Background information, procedures used, and typical results obtained are provided. (JN)

  3. Determination of Components in Beverages by Thin-Layer Chromatography.

    ERIC Educational Resources Information Center

    Ma, Yinfa; Yeung, Edward S.

    1990-01-01

    Described is a simple and interesting chromatography experiment using three different fluorescence detection principles for the determination of caffeine, saccharin and sodium benzoate in beverages. Experimental procedures and an analysis and discussion of the results are included. (CW)

  4. Further Thymol Derivatives from Ageratina cylindrica.

    PubMed

    Bustos-Brito, Celia; Esquivel, Baldomero; Calzada, Fernando; Yepez-Mulia, Lilian; Calderón, José S; Porras-Ramirez, Javier; Quijano, Leovigildo

    2016-10-01

    From the leaves of Ageratina cylindrica, in addition to the described [(2S)-2-{4-formyl-5-hydroxy-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl]methyl benzoate (cylindrinol A, 8), seven new thymol derivatives were isolated and named cylindrinols B - H (1 - 7). The structures of these compounds were established as (2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (1), (2-{4-formyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (2), (2-{4-[(acetyloxy)methyl]-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (3), [2-(2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (4), [2-(5-hydroxy-2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (5), 2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}prop-2-en-1-yl benzoate (6), and 2-hydroxy-2-[2-hydroxy-4-(hydroxymethyl)-phenyl]-3-[(2-methylpropanoyl)oxy]propyl benzoate (7), by spectroscopic means. Compounds 1 showed moderate antiprotozoal activity on both protozoa. Compounds 4 and 5 showed selectivity on Giardia lamblia trophozoites. All isolated compounds were less active than two antiprotozoal drugs, metronidazole and emetine, used as positive controls. Compound 5 exhibited a high inhibitory effect on hyperpropulsive movement of the small intestine in rats; its effect was best than loperamide, antidiarrheal drug used as a positive control.

  5. Chemoprevention Against Breast Cancer with Genistein and Resveratrol

    DTIC Science & Technology

    2007-03-01

    signaling pathway, the PI3K/Akt pathway, as well as changes in sex steroid receptor co- activators . We have demonstrated that the estrogen receptors play...each estrogen or phytoestrogen individually. Estradiol benzoate. As seen in Table 1, a single s.c. dose of estradiol benzoate was able to...α and β along with an increase in progesterone receptor (PR) levels. We and others have shown that activation of the estrogen receptors by estradiol

  6. Use of aromatic salts for simultaneously removing SO.sub.2 and NO.sub.x pollutants from exhaust of a combustion system

    DOEpatents

    Levendis, Yiannis A.; Wise, Donald L.

    1994-10-04

    A method is disclosed for removing pollutants from the exhaust of combustion systems burning fuels containing substantial amounts of sulfur and nitrogen. An exemplary method of the invention involves the formation and reaction of a sorbent comprising calcium benzoate. The calcium benzoate is either dry-sprayed (in the form of a fine powder) or wet-sprayed in an aqueous solution in a high temperature environment such as a combustion chamber. The latter technique is feasible since calcium benzoate is a water-soluble form of calcium. When the dispersed particles of calcium benzoate are heated to a high temperature, the organic benzoate burns off and fine calcium oxide particles are formed. These particles are cenospheric (hollow) and have thin and highly porous walls, thus, affording optimum external and internal accessibility for reacting with toxic gaseous emissions such as SO.sub.2. Further, the combustion of the organic benzoate portion of the sorbent results in the conversion of NO.sub.x to N.sub.2.

  7. Anaerobic Degradation of Phthalate Isomers by Methanogenic Consortia

    PubMed Central

    Kleerebezem, Robbert; Pol, Look W. Hulshoff; Lettinga, Gatze

    1999-01-01

    Three methanogenic enrichment cultures, grown on ortho-phthalate, iso-phthalate, or terephthalate were obtained from digested sewage sludge or methanogenic granular sludge. Cultures grown on one of the phthalate isomers were not capable of degrading the other phthalate isomers. All three cultures had the ability to degrade benzoate. Maximum specific growth rates (μSmax) and biomass yields (YXtotS) of the mixed cultures were determined by using both the phthalate isomers and benzoate as substrates. Comparable values for these parameters were found for all three cultures. Values for μSmax and YXtotS were higher for growth on benzoate compared to the phthalate isomers. Based on measured and estimated values for the microbial yield of the methanogens in the mixed culture, specific yields for the phthalate and benzoate fermenting organisms were calculated. A kinetic model, involving three microbial species, was developed to predict intermediate acetate and hydrogen accumulation and the final production of methane. Values for the ratio of the concentrations of methanogenic organisms, versus the phthalate isomer and benzoate fermenting organisms, and apparent half-saturation constants (KS) for the methanogens were calculated. By using this combination of measured and estimated parameter values, a reasonable description of intermediate accumulation and methane formation was obtained, with the initial concentration of phthalate fermenting organisms being the only variable. The energetic efficiency for growth of the fermenting organisms on the phthalate isomers was calculated to be significantly smaller than for growth on benzoate. PMID:10049876

  8. Biorational agents--mechanism and importance in IPM and IRM programs for controlling agricultural pests.

    PubMed

    Ishaaya, I; Kontsedalov, S; Mazirov, D; Horowitz, A R

    2001-01-01

    Among the new approaches for controlling agricultural pests is the development of novel compounds affecting specific processes in insects such as chitin synthesis inhibitors, juvenile hormone mimics and ecdysone agonists. In addition, efforts have been made to develop compounds acting selectively on groups of insects by inhibiting or enhancing biochemical sites such as respiration (diafenthiuron), the nicotinyl acetylcholine receptors (imidacloprid and acetamiprid), the GABA receptors (avermectins), the salivary glands of sucking pests (pymetrozine) and others. Among the most recent novel insecticides with selective properties are novaluron, thiamethoxam, emamectin and spinosad. Novaluron (Rimon) is a novel chitin synthesis inhibitor that acts by both ingestion and contact. It is a powerful suppressor of lepidopteran larvae such as Spodoptera littoralis and Helicoverpa armigera (by ingestion) and of whiteflies such as Bemisia tabaci and Trialeurodes vaporariorum (by contact). Thiamethoxam (Actarn), a novel neonicotinoid acts specifically on aphids and whiteflies. Emamectin (Proclaim), an avermectin derivative acts on GABA receptor affecting diversity of insects such as mites, lepidopterans and thrips. Spinosad (Tracer) seems to act on both acetylcholine and GABA receptors affecting diversity of insect species and is considered an important agent for controlling the western flower thrips.

  9. Biocatalytic Conversion of Avermectin to 4″-Oxo-Avermectin: Improvement of Cytochrome P450 Monooxygenase Specificity by Directed Evolution▿ †

    PubMed Central

    Trefzer, Axel; Jungmann, Volker; Molnár, István; Botejue, Ajit; Buckel, Dagmar; Frey, Gerhard; Hill, D. Steven; Jörg, Mario; Ligon, James M.; Mason, Dylan; Moore, David; Pachlatko, J. Paul; Richardson, Toby H.; Spangenberg, Petra; Wall, Mark A.; Zirkle, Ross; Stege, Justin T.

    2007-01-01

    Discovery of the CYP107Z subfamily of cytochrome P450 oxidases (CYPs) led to an alternative biocatalytic synthesis of 4″-oxo-avermectin, a key intermediate for the commercial production of the semisynthetic insecticide emamectin. However, under industrial process conditions, these wild-type CYPs showed lower yields due to side product formation. Molecular evolution employing GeneReassembly was used to improve the regiospecificity of these enzymes by a combination of random mutagenesis, protein structure-guided site-directed mutagenesis, and recombination of multiple natural and synthetic CYP107Z gene fragments. To assess the specificity of CYP mutants, a miniaturized, whole-cell biocatalytic reaction system that allowed high-throughput screening of large numbers of variants was developed. In an iterative process consisting of four successive rounds of GeneReassembly evolution, enzyme variants with significantly improved specificity for the production of 4″-oxo-avermectin were identified; these variants could be employed for a more economical industrial biocatalytic process to manufacture emamectin. PMID:17483257

  10. Crystal structure of (±)-(1SR,5SR,6SR,7SR,10SR,11SR,13SR)-13-benz-yloxy-7-meth-oxy-meth-oxy-11,15,18,18-tetra-methyl-3-oxo-2,4-dioxa-tetra-cyclo-[12.3.1.0(1,5).0(6,11)]octa-deca-14,16-dien-10-yl benzoate.

    PubMed

    Oishi, Takeshi; Fukaya, Keisuke; Yamaguchi, Yu; Sugai, Tomoya; Watanabe, Ami; Sato, Takaaki; Chida, Noritaka

    2015-05-01

    In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by -0.287 (5) and 0.174 (5) Å. The cyclo-hexane, cyclo-hexa-diene and central cyclo-octane rings show chair, half-chair and boat-chair forms, respectively. As a result of the strained ring system, the tetra-subsituted olefin in the cyclo-hexa-diene is skewed from an ideal planar structure. In the crystal, C-H⋯O hydrogen bonds connect the mol-ecules into a sheet parallel to (100). The sheets are further linked by other weak C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

  11. Phenotype fingerprinting suggests the involvement of single-genotype consortia in degradation of aromatic compounds by Rhodopseudomonas palustris

    SciTech Connect

    Karpinets, Tatiana V; Pelletier, Dale A; Pan, Chongle; Uberbacher, Edward C; Hettich, Robert {Bob} L; Samatova, Nagiza F

    2009-01-01

    Understanding of cellular processes involved in the anaerobic degradation of complex organic compounds by microorganisms is crucial for development of innovative biotechnologies for bioethanol production and for efficient degradation of toxic organic compounds. In natural environment the degradation is usually accomplished by syntrophic consortia comprised of different bacterial species. Here we show that the metabolically versatile phototrophic bacterium Rhodopseudomonas palustris may form its own syntrophic consortia, when it grows anaerobically on p-coumarate or benzoate as a sole carbon source. In the study we reveal the consortia from a comparison of large-scale measurements of mRNA and protein expressions under p-coumarate and benzoate degrading conditions using a novel computational approach referred as phenotype fingerprinting. In this approach marker genes for known R. palustris phenotypes are employed to calculate their expression from the gene and protein expressions in each studied condition. Subpopulations of the consortia are inferred from the expression of phenotypes and known metabolic modes of the R. palustris growth. We find that p-coumarate degrading condition leads to at least three R. palustris subpopulations utilizing p-coumarate, benzoate, and CO2 and H2. Benzoate degrading condition also produces at least three subpopulations utilizing benzoate, CO2 and H2, and N2 and formate. Communication among syntrophs and inter-syntrophic dynamics in each consortium are indicated by up-regulation of transporters and genes involved in the curli formation and chemotaxis. The photoautotrphic subpopulation found in both consortia is characterized by activation of two cbb operons and the uptake hydrogenase system. A specificity of N2-fixing subpopulation in the benzoate degrading consortium is the preferential activation of the vanadium nitrogenase over the molybdenum nitrogenase. The N2-fixing subpopulation in the consortium is confirmed by consumption of

  12. An antiprogestin, CDB4124, blocks progesterone's attenuation of the negative effects of a mild stress on sexual behavior.

    PubMed

    Uphouse, Lynda; Hiegel, Cindy

    2013-03-01

    These experiments were designed to test the hypothesis that a progesterone receptor antagonist would block progesterone's ability to reduce the negative effects of a 5 min restraint on female rat sexual behavior. Ovariectomized Fischer rats were injected with 10 μg estradiol benzoate. Two days later, rats were injected subcutaneously (sc) with the progesterone receptor antagonist, CDB4124 (17α-acetoxy-21-methoxy-11β-[4-N,N-dimethyaminopheny]-19-norpregna-4,9-dione-3,20-dione) (60 mg/kg), or vehicle (20% DMSO+propylene glycol). One hour later, rats were injected sc with 500 μg progesterone or vehicle (sesame seed oil). Rats were assigned to one of three different treatment conditions: (1) (ECV) estradiol benzoate, CDB4124, sesame seed oil vehicle, (2) (ECP) estradiol benzoate, CDB4124, progesterone, and (3) (EVP) estradiol benzoate, DMSO/propylene glycol vehicle, progesterone. That afternoon sexual behavior was examined before and after a 5 min restraint experience. Before restraint, lordosis behavior was comparable across treatment conditions but only progesterone-treated rats exhibited proceptive behavior. CDB4124 did not block progesterone's induction of proceptivity. However, after restraint, CDB4124 attenuated the positive effects of progesterone on all sexual behaviors examined. The restraint experience inhibited sexual behavior in rats treated with estradiol benzoate and CDB4124 and in rats treated with estradiol benzoate, CDB4124, and progesterone but not in rats given estradiol benzoate and progesterone without CDB4124. These findings are consistent with the hypothesis that progesterone receptors mediate progesterone's ability to reduce the negative sexual behavioral effects of a mild stressor.

  13. Cholesterol in situ forming gel loaded with doxycycline hyclate for intra-periodontal pocket delivery.

    PubMed

    Phaechamud, Thawatchai; Setthajindalert, Orn

    2017-03-01

    Cholesterol has been widely used in drug delivery systems including implant. Doxycycline hyclate (DH)-loaded cholesterol in situ forming gels using N-methyl pyrrolidone as a solvent were prepared and investigated for their properties including viscosity, rheology, syringeability, gel formation, drug release, degradation and antimicrobial activities. The burst drug release of a DH-loaded in situ forming gel using cholesterol as the gelling agent was minimized when the amount of benzyl benzoate was increased. The viscosity of the system was increased as the amount of benzyl benzoate was increased with Newtonian flow. The systems were easy to inject into the target site because of their minimal force of syringeability. They could transform from solution into matrix-like structures, but formulations with higher concentrations of benzyl benzoate took a longer time. However, the degradability was decreased when the amount of benzyl benzoate was increased. These systems inhibited P. gingivalis, S. mutans and S. aureus effectively. DH-loaded cholesterol in situ forming gel system comprising 10% benzyl benzoate was the most suitable owing to its sustainable release manner for 10days and therefore was the proper formulation for periodontitis treatment.

  14. Degradation of Monochlorinated and Nonchlorinated Aromatic Compounds under Iron-Reducing Conditions

    PubMed Central

    Kazumi, J.; Haggblom, M. M.; Young, L. Y.

    1995-01-01

    The capacity for Fe(sup3+) to serve as an electron acceptor in the microbial degradation of monochlorinated and nonchlorinated aromatic compounds was investigated in anoxic sediment enrichments. The substrates tested included phenol, benzoate, aniline, their respective monochlorinated isomers, o-, m-, and p-cresol, and all six dimethylphenol isomers. Phenol and 2-, 3-, and 4-chlorophenol were utilized by anaerobic microorganisms, with the concomitant reduction of Fe(sup3+) to Fe(sup2+). The amount of Fe(sup2+) produced in the enrichments was 89 to 138% of that expected for the stoichiometric degradation of these substrates to CO(inf2), suggesting complete mineralization at the expense of Fe reduction. Under Fe-reducing conditions, there was initial loss of benzoate and 3-chlorobenzoate but not of 2- or 4-chlorobenzoate. In addition, there was initial microbial utilization of aniline but not of the chloroaniline isomers. There was also initial loss of o-, m-, and p-cresol in our enrichments. None of the dimethylphenol isomers, however, was degraded within 300 days. Furthermore, we tested the capacity of an Fe-reducing, benzoate-grown culture of Geobacter metallireducens GS-15 to utilize monochlorinated benzoates and phenols. G. metallireducens was able to degrade benzoate and phenol but none of their chlorinated isomers, suggesting that the degradation of chlorophenols in our sediment enrichments may be due to novel Fe-reducing organisms that have yet to be isolated. PMID:16535169

  15. Antagonistic control of a dual-input mammalian gene switch by food additives

    PubMed Central

    Xie, Mingqi; Ye, Haifeng; Hamri, Ghislaine Charpin-El; Fussenegger, Martin

    2014-01-01

    Synthetic biology has significantly advanced the design of mammalian trigger-inducible transgene-control devices that are able to programme complex cellular behaviour. Fruit-based benzoate derivatives licensed as food additives, such as flavours (e.g. vanillate) and preservatives (e.g. benzoate), are a particularly attractive class of trigger compounds for orthogonal mammalian transgene control devices because of their innocuousness, physiological compatibility and simple oral administration. Capitalizing on the genetic componentry of the soil bacterium Comamonas testosteroni, which has evolved to catabolize a variety of aromatic compounds, we have designed different mammalian gene expression systems that could be induced and repressed by the food additives benzoate and vanillate. When implanting designer cells engineered for gene switch-driven expression of the human placental secreted alkaline phosphatase (SEAP) into mice, blood SEAP levels of treated animals directly correlated with a benzoate-enriched drinking programme. Additionally, the benzoate-/vanillate-responsive device was compatible with other transgene control systems and could be assembled into higher-order control networks providing expression dynamics reminiscent of a lap-timing stopwatch. Designer gene switches using licensed food additives as trigger compounds to achieve antagonistic dual-input expression profiles and provide novel control topologies and regulation dynamics may advance future gene- and cell-based therapies. PMID:25030908

  16. Anaerobic Degradation of the Benzene Nucleus by a Facultatively Anaerobic Microorganism1

    PubMed Central

    Taylor, Barrie F.; Campbell, William L.; Chinoy, Ira

    1970-01-01

    A bacterium was isolated by elective culture with p-hydroxybenzoate as substrate and nitrate as electron acceptor. It grew either aerobically or anaerobically, by nitrate respiration, on a range of aromatic compounds. The organism was identified as a pseudomonad and was given the trivial name Pseudomonas PN-1. Benzoate and p-hydroxybenzoate were metabolized aerobically via protocatechuate, followed by meta cleavage catalyzed by protocatechuic acid-4,5-oxygenase, to yield α-hydroxy-γ-carboxymuconic semialdehyde. Pseudomonas PN-1 grew rapidly on p-hydroxybenzoate under strictly anaerobic conditions, provided nitrate was present, even though protocatechuic acid-4,5-oxygenase was repressed. Suspensions of cells grown anaerobically on p-hydroxybenzoate oxidized benzoate with nitrate and produced 4 to 5 μmoles of CO2 per μmole of benzoate added; these cells did not oxidize benzoate aerobically. The patterns of the oxidation of aromatic substrates with oxygen or nitrate by cells grown aerobically or anaerobically on different aromatic compounds indicated that benzoate rather than protocatechuate was a key intermediate in the early stages of anaerobic metabolism. It was concluded that the pathway for the anaerobic breakdown of the aromatic ring is different and quite distinct from the aerobic pathway. Mechanisms for the anaerobic degradation of the benzene nucleus by Pseudomonas PN-1 are discussed. PMID:5419260

  17. Antagonistic control of a dual-input mammalian gene switch by food additives.

    PubMed

    Xie, Mingqi; Ye, Haifeng; Hamri, Ghislaine Charpin-El; Fussenegger, Martin

    2014-08-01

    Synthetic biology has significantly advanced the design of mammalian trigger-inducible transgene-control devices that are able to programme complex cellular behaviour. Fruit-based benzoate derivatives licensed as food additives, such as flavours (e.g. vanillate) and preservatives (e.g. benzoate), are a particularly attractive class of trigger compounds for orthogonal mammalian transgene control devices because of their innocuousness, physiological compatibility and simple oral administration. Capitalizing on the genetic componentry of the soil bacterium Comamonas testosteroni, which has evolved to catabolize a variety of aromatic compounds, we have designed different mammalian gene expression systems that could be induced and repressed by the food additives benzoate and vanillate. When implanting designer cells engineered for gene switch-driven expression of the human placental secreted alkaline phosphatase (SEAP) into mice, blood SEAP levels of treated animals directly correlated with a benzoate-enriched drinking programme. Additionally, the benzoate-/vanillate-responsive device was compatible with other transgene control systems and could be assembled into higher-order control networks providing expression dynamics reminiscent of a lap-timing stopwatch. Designer gene switches using licensed food additives as trigger compounds to achieve antagonistic dual-input expression profiles and provide novel control topologies and regulation dynamics may advance future gene- and cell-based therapies.

  18. Pressure drop in fully developed, duct flow of dispersed liquid-vapor mixture at zero gravity

    NASA Technical Reports Server (NTRS)

    Sridhar, K. R.; Chao, B. T.; Soo, S. L.

    1990-01-01

    The dynamics of steady, fully developed dispersed liquid-vapor flow in a straight duct at 0-g is simulated by flowing water containing n-butyl benzoate droplets. Water and benzoate are immiscible and have identical density at room temperature. The theoretical basis of the simulation is given. Experiments showed that, for a fixed combined flow rate of water and benzoate, the frictional pressure drop is unaffected by large changes in the volume fraction of benzoate drops and their size distribution. Measured power spectra of the static wall pressure fluctuations induced by the turbulent water-benzoate flow also revealed that their dynamics is essentially unaltered by the presence of the droplets. These experimental findings, together with the theoretical analysis, led to the conclusion that the pressure drop in fully developed, dispersed liquid-vapor flow in straight ducts of constant cross section at 0-g is identical to that due to liquid flowing alone at the same total volumetric flow rate of the liquid-vapor mixture and, therefore, can be readily determined.

  19. D-003 does not possess oestrogenic potential in-vivo: findings of the uterotrophic assay.

    PubMed

    Noa, Miriam; Mendoza, Sarahí; Mas, Rosa; Gámez, Rafael; Valle, Maikel; Pardo, Balia; Gutiérrez, Ariadne; Mendoza, Nilda

    2007-10-01

    D-003 is a mixture of long-chain fatty acids purified from sugarcane wax that inhibits both cholesterol synthesis prior to mevalonate formation, and lipid peroxidation. D-003 has been shown to prevent bone loss and bone resorption in ovariectomized rats, and significantly improves bone resorption markers in postmenopausal women with reduced bone mineral density. As hormone-replacement therapy, D-003 displays cholesterol-lowering and anti-resorptive effects. We have studied its potential oestrogenic activity in-vivo using the uterotrophic assay. Rats were randomly distributed into five groups: a sham-operated group and four groups of ovariectomized rats, one treated with vehicle, one with D-003 (50 mg kg(-1)), one with oestradiol benzoate (30 microg kg(-1)) and one with D-003 (50 mg kg(-1)) plus oestradiol benzoate (30 microg kg(-1)). Treatments were administered for 14 days. Ovariectomy decreased the values of relative uterus weight, epithelium cell height and endometrial thickness compared with sham-operated rats, and these effects were all significantly reduced with oestradiol benzoate, but not with D-003. Concurrent administration of D-003 and oestradiol benzoate had statistically similar effects on all variables as oestradiol benzoate alone. In conclusions, D-003 orally given at 50 mg kg(-1), a dose that prevents bone loss and bone resorption in ovariectomized rats, did not display oestrogenic/anti-oestrogenic activity in-vivo, as assessed in the uterotrophic assay.

  20. Effects of some insecticides on longevity of the foragers honey bee worker of local honey bee race Apis mellifera jemenatica

    PubMed Central

    Aljedani, Dalal Musleh; Almehmadi, Roqaya Mohammed

    2016-01-01

    Introduction Honeybees are constantly exposed to a wide range of vital and non-vital pressures that may interact with each other and affect the health or survival of the insects. Pesticides are the main danger for the insects, and they subsequently have impacts on human and environmental health. Methods Field research was conducted in the apiary of Hada Al Sham Research Station, where the worker honeybees forager Apis mellifera jemenatica were selected to examine the effect of pesticides on workers’ longevity. We used three insecticides, i.e., deltamethrin, malathion, and abamectin, in different concentrations. The longevity of worker honeybee foragers was calculated; the honeybees were supplied with water, food, natural protein, and sugar solution laced with selected insecticide by mouth under laboratory conditions. Results The longest period of insect longevity was 15.5 days when using deltamethrin concentrate at a concentration of 1.00 ppm; the lowest longevity was two days when using abamectin at a concentration 1.00 ppm. The longevity of the unexposed forager worker honeybees was 18 days, as the variation in the intensity of the effect of the insecticide on the bees appeared with the severity of the effect diminishing in the order of abamectin followed by malathion followed by deltamethrin. Conclusion The study found that the type and concentration of the insecticides that are found in the honeybees’ food had a significant impact on the time of survival of the insects. The longevity of a worker honeybee depends on the health and safety of all of the members of the beehive, and safe alternatives to insecticides must be used because of the danger imposed by the application of insecticides on the continuity of life of the entire society depends on the life of this layer bee community. PMID:26955457

  1. The persistence toxicity of four insecticides against adult Hippodamia varigata (Coleptera: Cocinellidae).

    PubMed

    Almasi, A; Sabahi, Q; Kavousi, A

    2012-01-01

    In order to investigate the effects of four insecticides on Hippodomia variegata (Coleoptera: Coccinellidae), the predator of Aphis fabae, an experiment was carried out using IOBC/wprs method. Persistence toxicity of insecticides has been evaluated in the greenhouse condition. The insecticides abamectin 1.8 EC, deltamethrin 2.5 EC, imidacloprid 350 SC, and proteus OD 110 were used at recommended field rates. The insecticides were applied on broad bean foliage using a hand sprayer, until run-off. Contact toxicity of aged residues of insecticides on adult predator was evaluated using the cage-method. The trials were laid out in randomized complete design (CRD) with 3 replicates and an untreated check. The arcsine transformation was used for analysis. The mortality of adult predator, after 24 h contact with fresh residues of abamectin, deltamethrin, imidacloprid and proteus were 53.4, 52.1, 63.4 and 65.1%, respectively. After 5 days the effect of residues decreased so that the adult mortality diminished to 32.4, 36.5, 56.1 and 57.5% for mentioned above insecticides. 15-day old residues lead to 8.8, 23.1, 56.3 and 57.5%; and 31-day old residues lead to 8.8, 22.7, 29.5 and 41.7% mortality for these insecticides, respectively. Based on this study, abamectin and deltamethrin with persistence less than 5 d are classified as short lived (Class A) while imidacloprid and proteus with persistence between 16 to 31d, classified as moderately persistent (Class C) compounds.

  2. Toxicity of sediment-associated pesticides to Chironomus dilutus and Hyalella azteca.

    PubMed

    Ding, Yuping; Weston, Donald P; You, Jing; Rothert, Amanda K; Lydy, Michael J

    2011-07-01

    Two hundred sediment samples were collected and their toxicity evaluated to aquatic species in a previous study in the agriculturally dominated Central Valley of California, United States. Pyrethroid insecticides were the main contributors to the observed toxicity. However, mortality in approximately one third of the toxic samples could not be explained solely by the presence of pyrethroids in the matrices. Hundreds of pesticides are currently used in the Central Valley of California, but only a few dozen are analyzed in standard environmental monitoring. A significant amount of unexplained sediment toxicity may be due to pesticides that are in widespread use that but have not been routinely monitored in the environment, and even if some of them were, the concentrations harmful to aquatic organisms are unknown. In this study, toxicity thresholds for nine sediment-associated pesticides including abamectin, diazinon, dicofol, fenpropathrin, indoxacarb, methyl parathion, oxyfluorfen, propargite, and pyraclostrobin were established for two aquatic species, the midge Chironomus dilutus and the amphipod Hyalella azteca. For midges, the median lethal concentration (LC₅₀) of the pesticides ranged from 0.18 to 964 μg/g organic carbon (OC), with abamectin being the most toxic and propargite being the least toxic pesticide. A sublethal growth endpoint using average individual ash-free dry mass was also measured for the midges. The no-observable effect concentration values for growth ranged from 0.10 to 633 μg/g OC for the nine pesticides. For the amphipods, fenpropathrin was the most toxic, with an LC₅₀ of 1-2 μg/g OC. Abamectin, diazinon, and methyl parathion were all moderately toxic (LC₅₀s 2.8-26 μg/g OC). Dicofol, indoxacarb, oxyfluorfen, propargite, and pyraclostrobin were all relatively nontoxic, with LC₅₀s greater than the highest concentrations tested. The toxicity information collected in the present study will be helpful in decreasing the

  3. Energetics and kinetics of anaerobic aromatic and fatty acid degradation. Progress report, November 1993--November 1994

    SciTech Connect

    McInerney, M.J.

    1994-12-06

    Factors influencing the rate and extent of benzoate degradation by the anaerobic syntrophic consortia were studied. Nonlinear regression analysis showed that the cause of the benzoate threshold was not a diminished benzoate degradation capacity. Analysis of cocultures with hydrogen users that differed in their hydrogen utilization capacities showed that the threshold did not depend on the kinetic properties of the syntrophic partner. These data support a thermodynamic explanation for the threshold, and exclude the possibility that a change in the affinity of the enzyme system due to acetate inhibition caused the threshold. Modeling studies showed that the threshold value could be predicted from the concentrations of the end products, assuming a critical Gibb`s free energy value. This work shows that interspecies acetate transfer is important in controlling the extent of metabolism by syntrophic organisms.

  4. Effect of community structure on the kinetics of anaerobic degradation of aromatic compounds

    SciTech Connect

    McInerney, M.J.

    1990-11-01

    The kinetics of benzoate degradation by Syntrophus buswellii grown in coculture with Desulfovibrio strain G11 was determined. Benzoate was degraded to a threshold value where no futher benzoate degradation was detected even after long incubation times. The addition of sodium acetate, but not sodium chloride, was found to affect the threshold value with higher values observed at higher acetate concentrations. Syntrophus buswellii was isolated in pure culture with crotonate as the substrate. Also, an anaerobic, fermentative bacterium that metabolizes 3-chlorophenoxyacetate and phenoxyacetate to the corresponding phenol was isolated in pure culture. The synthesis of poly-3-hydroxyalkanoate (PHA) in Syntrophomonas wolfei was studied. The bacterium synthesized PHA directly from the {Beta}-oxidation intermediate during the initial stages of growth. Later, PHA was made by the condensation of two acetyl-CoA molecules. The genes for PHA synthesis in S. wolfei have been cloned into Escherichia coli.

  5. catena-Poly[[[(1,10-phenanthroline-κ(2)N,N')praseodymium(III)]-di-μ-4-hydroxy-benzoato-κ(4)O(1):O(1')-μ-nitrato-κ(3)O,O':O] bis-(1,10-phenanthroline)].

    PubMed

    Wang, Panfeng; Xu, Dingding; Wang, Xinqing

    2012-09-01

    The title complex, [Pr(C(7)H(5)O(3))(2)(NO(3))(C(12)H(8)N(2))]·2C(12)H(8)N(2), has a polymeric chain structure, with two uncoordinated 1,10-phenanthroline mol-ecules in the lattice. The Pr(III) centre has a monocapped square-anti-prismatic coordination geometry, comprised of two N atoms from one chelating 1,10-phenanthroline ligand, four carboxyl-ate O atoms from four 4-hy-droxy-benzoate anions and three O atoms from two nitrate anions. The 4-hy-droxy-benzoate and nitrate anions function as μ(2)-bridging ligands and link the Pr(III) ions into a one-dimensional chain structure along the c axis. Inter-molecular O-H⋯N hydrogen bonds are observed between the 4-hy-droxy-benzoate anions and the uncoordinated 1,10-phenanthroline mol-ecules.

  6. Effects of exogenous oestrogen and experimentally induced endometritis on absorption of sodium benzylpenicillin from the cow's uterus.

    PubMed

    Ayliffe, T R; Noakes, D E

    1982-01-30

    The effects of oestradiol benzoate or of experimentally induced infection on the absorption of sodium benzylpenicillin from the uterus were investigated in three groups of clinically normal, non-pregnant, Friesian cows. All were at day 12 following the day of oestrus. Oestradiol benzoate in oil was administered either into the uterus or intramuscularly one hour before the infusion of 22,000 iu/kg of sodium benzylpenicillin. The dose of oestradiol benzoate was 10 mg, apart from one cow in each group which received 25 mg. Inflammation was induced by infusing a suspension of Corynebacterium pyogenes in Ringer's solution into the uterus, 11 to 18 hours before penicillin infusion. The degree of absorption of penicillin was greater in all three groups than that previously determined in cows given penicillin alone at the same stage of the cycle. The results indicate that factors which might affect blood flow to the uterus may also influence the absorption of sodium benzylpenicillin from the uterus.

  7. Prior hormonal treatment, but not sexual experience, reduces the negative effects of restraint on female sexual behavior.

    PubMed

    Uphouse, Lynda; Hiegel, Cindy; Adams, Sarah; Murillo, Vanessa; Martinez, Monique

    2014-02-01

    These experiments were designed to determine if prior sexual experience reduced the negative effect of mild stress on female sexual behavior. In the first experiment, ovariectomized rats were hormonally primed with estradiol benzoate and progesterone for 3 consecutive weeks during which they received six mating experiences in a male's home cage or received no sexual experience. The next week, females were primed with 10 μg estradiol benzoate two days before a 5 min restraint. Both groups were resistant to the negative effects of the stressor. In the second experiment, females received 0, 1, 2, or 3 weeks of 10 μg estradiol benzoate and were restrained on the fourth week after priming with 10 μg estradiol benzoate. Rats without prior hormonal priming showed a decline in lordosis behavior after restraint but prior priming with estradiol benzoate reduced this effect. In the third experiment, rats received 3 weeks of hormonal priming with estradiol benzoate and progesterone with or without sexual experience. An additional group received no sexual experience or hormonal priming. Females were then given a 3-week hormone vacation before testing in the restraint paradigm. All groups showed a decline in lordosis behavior after restraint. The fourth experiment was identical to the third except that sexual experience in the male's cage and in a pacing apparatus were compared. There was no effect of either type of sexual experience on the response to restraint. Possible mechanisms responsible for effects of prior hormonal priming are presented and the absence of an effect of sexual experience is discussed in comparison to findings in male rats.

  8. Distribution of Heavy Metals in the Soils Associated with the Commonly Used Pesticides in Cotton Fields

    PubMed Central

    Shafiq, Musharaf; Chotana, Ghayoor Abbas

    2016-01-01

    Agricultural soils contain both heavy metals and pesticides originating from various agricultural practices. It is quite important to study the relationships between these two classes of compounds. To accomplish this, 52 soil samples were collected from cotton fields and analyzed for their metal contents (Ni, Cu, Co, Pb, Cr, and Cd) and levels of most commonly used pesticides (imidacloprid, acetamiprid, and emamectin). FAAS was used for metal estimation and the pesticides were determined by HPLC equipped with UV detector. The results of the study revealed slightly enhanced levels of Ni and Cd in these samples while the rest of the metals were present within tolerable range. Acetamiprid residues in soil were strongly positively correlated with Cu and negatively correlated with Cr. Similarly, imidacloprid in soil was negatively correlated with Ni. Thus it was evidenced that Cu stabilizes acetamiprid while Cr and Ni facilitate the degradation of acetamiprid and imidacloprid in the soil. PMID:27051560

  9. Distribution of Heavy Metals in the Soils Associated with the Commonly Used Pesticides in Cotton Fields.

    PubMed

    Tariq, Saadia Rashid; Shafiq, Musharaf; Chotana, Ghayoor Abbas

    2016-01-01

    Agricultural soils contain both heavy metals and pesticides originating from various agricultural practices. It is quite important to study the relationships between these two classes of compounds. To accomplish this, 52 soil samples were collected from cotton fields and analyzed for their metal contents (Ni, Cu, Co, Pb, Cr, and Cd) and levels of most commonly used pesticides (imidacloprid, acetamiprid, and emamectin). FAAS was used for metal estimation and the pesticides were determined by HPLC equipped with UV detector. The results of the study revealed slightly enhanced levels of Ni and Cd in these samples while the rest of the metals were present within tolerable range. Acetamiprid residues in soil were strongly positively correlated with Cu and negatively correlated with Cr. Similarly, imidacloprid in soil was negatively correlated with Ni. Thus it was evidenced that Cu stabilizes acetamiprid while Cr and Ni facilitate the degradation of acetamiprid and imidacloprid in the soil.

  10. The polymorphic and mesomorphic behavior of four esters of cholesterol.

    NASA Technical Reports Server (NTRS)

    Merritt, W. G.; Cole, G. D.; Walker, W. W.

    1971-01-01

    The techniques of differential scanning calorimetry, X-ray powder diffractometry, and positron annihilation have been used to study the polymorphic and mesomorphic behavior of the following esters of cholesterol: cholesteryl formate, cholesteryl butyrate, cholesteryl benzoate, and cholesteryl cinnamate. Each of these compounds exhibits a single mesophase of the cholesteric type. The solid phase formed from the melt for each ester was observed to be structurally different from the solid phase obtained from solution. Solvents from which the solution-grown samples were crystallized were as follows: cholesteryl formate and cholesteryl butyrate from acetone, cholesteryl benzoate from benzene, and cholesteryl cinnamate from 2-butanone.

  11. Structure determination of neptunium(VI) mu3-hydroxobenzoate, [(NpO2)2(mu3-OH)2(H5C6COO)2] x 2 H2O.

    PubMed

    Charushnikova, Iraida A; Krot, Nikolai N; Makarenkov, Vadim I

    2010-09-06

    Neptunium(VI) benzoate with mu(3)-OH(-) has been isolated and studied by the X-ray method. The main structural motive in the crystal is corrugated ribbons [(NpO(2))(2)(mu(3)-OH)(2)(C(7)H(5)O(2))(2)](n) extended along the c axes in which three neptunium pentagonal bipyramids are linked through the mu(3)-OH(-) ligand. The benzoate ions are arranged at both sides of the ribbons, and each anion binds two adjacent NpO(2). The water molecules are arranged in the channels along the c axis.

  12. Biological activity of secondary metabolites from Peltostigma guatemalense.

    PubMed

    Cuca Suarez, Luis Enrique; Pattarroyo, Manuel Elkin; Lozano, Jose Manuel; Delle Monache, Franco

    2009-01-01

    Leaves and wood of Peltostigma guatemalense, a novel species of the family Rutaceae, yielded a total of 14 secondary metabolites, i.e. methyl p-hydroxy benzoate, phenylacetic acid, beta-sitosterol, lupeol, syringaresinol, scopoletin, gardenin B (1), and seven alkaloids: gamma-fagarine (2), skimmianine (3), kokusaginine (4), 7-O-isopentenyl-gamma-fagarine (5), anhydro-evoxine (6), evoxine (7) and 4-methoxy-1-methyl-quinolin-2-one (8). The compounds have been identified by spectroscopic methods. Antibacterial and antimalarial in vitro activity of the isolated compounds were also determined. Methyl p-hydroxy benzoate and quinolone (8) were the most effective on Plasmodium falciparium strains.

  13. [Treatment of scabies with special consideration of the approach in infancy, pregnancy and while nursing].

    PubMed

    Fölster-Holst, R; Rufli, T; Christophers, E

    2000-01-01

    Infestation of human skin with scabies mites remains an persistent problem in daily dermatological practice. There are several therapeutic regiments against scabies which have been proven effective and without major side effects. Because of known neurotoxicity of lindane as well as intoxication/problems following systemic absorption of benzyl alcohol (the metabolite of benzyl benzoate), these two compounds have to be considered with caution in early childhood scabies as well as during pregnancy and nursing. The pharmacology and spectrum of clinical side effects of the approved anti-scabies preparations (lindane, benzyl benzoate, crotamiton) as well as permethrin (not available in Germany) are reviewed.

  14. [Biological activity tests of chemical constituents from two Brazilian Labiatae plants].

    PubMed

    Isobe, Takahiko; Doe, Matsumi; Morimoto, Yoshiki; Nagata, Kumiko; Masuoka, Noriyoshi; Ohsaki, Ayumi

    2007-02-01

    We studied the bioactivities of constituents from two tropical medicinal plants, Cunila spicata and Hyptis fasciculata. These plants found in Brazil belong to the Labiatae family. Four known compounds obtained from these herbs were identified as 3alpha, 24-dihydoxylurs-12-en-28-oic acid, betulinic acid, aurantiamide acetate, and aurantiamide benzoate by spectroscopic means. 3alpha, 24-Dihydoxylurs-12-en-28-oic acid has potent inhibitory activity against Streptococcus salivarius, Streptococcus pneumoniae, Streptococcus pyogenes, and Porphyromomas gingivalis. Aurantiamide benzoate exhibited moderate inhibitory activity against xanthine oxidase. It was clarified that herbs Cunila spicata and Hyptis fasciculata are effective against bronchitis and gout.

  15. Synthesis of bio-based nanocomposites for controlled release of antimicrobial agents in food packaging

    NASA Astrophysics Data System (ADS)

    DeGruson, Min Liu

    The utilization of bio-based polymers as packaging materials has attracted great attention in both scientific and industrial areas due to the non-renewable and nondegradable nature of synthetic plastic packaging. Polyhydroxyalkanoate (PHA) is a biobased polymer with excellent film-forming and coating properties, but exhibits brittleness, insufficient gas barrier properties, and poor thermal stability. The overall goal of the project was to develop the polyhydroxyalkanoate-based bio-nanocomposite films modified by antimicrobial agents with improved mechanical and gas barrier properties, along with a controlled release rate of antimicrobial agents for the inhibition of foodborne pathogens and fungi in food. The ability for antimicrobial agents to intercalate into layered double hydroxides depended on the nature of the antimicrobial agents, such as size, spatial structure, and polarity, etc. Benzoate and gallate anions were successfully intercalated into LDH in the present study and different amounts of benzoate anion were loaded into LDH under different reaction conditions. Incorporation of nanoparticles showed no significant effect on mechanical properties of polyhydroxybutyrate (PHB) films, however, significantly increased the tensile strength and elongation at break of polyhydroxybutyrate-co-valerate (PHBV) films. The effects of type and concentration of LDH nanoparticles (unmodified LDH and LDH modified by sodium benzoate and sodium gallate) on structure and properties of PHBV films were then studied. The arrangement of LDH in the bio-nanocomposite matrices ranged from exfoliated to phase-separated depending on the type and concentration of LDH nanoparticles. Intercalated or partially exfoliated structures were obtained using modified LDH, however, only phase-separated structures were formed using unmodified LDH. The mechanical (tensile strength and elongation at break) and thermo-mechanical (storage modulus) properties were significantly improved with low

  16. Short communication: Macrocyclic lactone residues in butter from Brazilian markets.

    PubMed

    Macedo, Fabio; Marsico, Eliane Teixeira; Conte-Júnior, Carlos Adam; de Almeida Furtado, Leonardo; Brasil, Taila Figueredo; Pereira Netto, Annibal Duarte

    2015-06-01

    Macrocyclic lactones (ML) are commonly used in drug formulations for the treatment of parasites in cattle. In Brazil, except for drugs (or formulations) with long-term (half-life) effects, ML are registered for use in bovines. Indiscriminate use of ML may result in the presence of residues in milk and dairy products due to their lipophilic properties and thermal stability. This study applied a method of liquid chromatography with fluorimetric detection, recently developed and validated for the determination of residues of abamectin, doramectin, ivermectin, and moxidectin in butter. The method was applied to 38 samples of commercial butter purchased in the metropolitan area of Rio de Janeiro, Brazil, between June and September 2013, analyzed in triplicate. Ivermectin was detected in 89.5% of the samples, with concentrations between 0.3 and 119.4 µg/kg; 76.3% of the samples contained doramectin (0.6 to 64.7 µg/kg) and 55.2% contained abamectin (0.7 to 4.5 µg/kg). Most butter samples (76.3%) contained residues of more than 1 ML; however, no residues of moxidectin were detected. The results showed a high incidence of the presence of avermectins in butter samples. Butter is not included in the Brazilian National Plan for Control of Residues and Contaminants in Animal Products. As ML residues concentrate in lipophilic compounds, butter and other fatty dairy products should be screened for the presence of ML residues.

  17. Toxicity of plant essential oils to acaricide-susceptible and -resistant Tetranychus urticae (Acari: Tetranychidae) and Neoseiulus californicus (Acari: Phytoseiidae).

    PubMed

    Han, Jun; Choi, Byeoung-Ryeol; Lee, Sang-Gyeu; Kim, Soon Il; Ahn, Young-Joon

    2010-08-01

    The toxicity of 10 plant essential oils to adults of acaricide-susceptible, chlorfenapyr-resistant (CRT-53), fenpropathrin-resistant (FRT-53), pyridaben-resistant (PRT-53), and abamectin-resistant (ART-53) strains of Tetranychus urticae Koch (Acari: Tetranychidae) and to female Neoseiulus californicus McGregor (Acari: Phytoseiidae) was examined using spray or vapor-phase mortality bioassays. In bioassay with the susceptible adults, lemon eucalyptus (19.3 microg/cm3) was the most toxic oil, followed by peppermint, citronella Java, thyme red, caraway seed, clove leaf, and pennyroyal oils (LC50, 20.6-23.7 microg/cm3). The toxicity of these oils was almost identical against adults from either of the susceptible and resistant strains, even though CRT-53, FRT-53, PRT-53, and ART-53 adults exhibited high levels of resistance to chlorfenapyr (resistance ratio [RR], > 9,140), fenpropathrin (RR, 94), pyridaben (RR, > 390), and abamectin (RR, 85), respectively. Against female N. californicus, lemon eucalyptus (LC50, 21.4 microg/cm3) was the most toxic oil, whereas the LC50 values of the other nine oils ranged from 23.2 to 72.6 microg/cm3. N. californicus was 1-2 times more tolerant than T. urticae to the test essential oils. Thus, these essential oils merit further study as potential acaricides for the control of acaricide-resistant T. urticae populations as fumigants.

  18. Determination of natural pesticides in fresh fruits using liquid chromatography/mass spectrometry.

    PubMed

    Ruiz, Irene; Morales, Ascensión; Barba, Alberto; Oliva, José

    2012-01-01

    An analytical procedure was developed for the determination of some natural pesticides (piperonyl butoxide, nicotine, rotenone, spinosad, and abamectin B1a) in fruit matrixes. The quick, easy, cheap, effective, rugged, and safe (QuEChERS) method was used for extraction. Analysis of the extract was performed by LC-electrospray ionization (ESI)-MS/MS. The ions prominent in the ESI spectra were [M+Na]+ for abamectin B1a, [M+NH4]+ for piperonyl butoxide, and [M+H]+ for the rest of the compounds. A Zorbax SB-C18 column was used with a programmed gradient mobile phase consisting of (A) water containing 0.1% formic acid and 5 mM ammonium formate, and (B) acetonitrile containing 2 mM sodium acetate. The method was linear within the investigated concentration range, displaying a calibration curve correlation factor of 0.99. The CVs obtained were below 20%, and recoveries were in the 70-110% range.

  19. Acaricides and predatory mites against the begonia mite, Polyphagotarsonemus latus (Acari: Tarsonemidae), on Hedera helix.

    PubMed

    Audenaert, Joachim; Vissers, Marc; Haleydt, Bart; Verhoeven, Ruth; Goossens, Frans; Gobin, Bruno

    2009-01-01

    In recent years, the begonia mite (Polyphagotarsonemus lotus) has become an important threat to different ornamental cultures in warm greenhouses. At present there are no professional plant protection products registered in Belgium for the control of mites of the Tarsonemidae family. In a screening trial, we evaluated the efficacy of a range of different acaricides: abamectin, milbemectin, pyridaben, spirodiclofen. Based on the results of the screening trial several products were selected for a full efficacy trial following EPPO guidelines. The best control results were obtained with two products from the avermectine group: abamectin and milbemectin. As growers currently have to rely solely on the use of natural enemies there is a strong need for practical evaluation of efficacies of the various predatory mite species (Amblyseius swirskii, A. cucumeris, A. andersoni) used in biological mite control. In a series of experiments, we screened the use of different species of predatory mites. The first efficacy trials on heavily infested plants at different rates of dosage and under different circumstances (temperature, dose rate, application technique) were started in May 2008. In these experiments Amblyseius swirskii showed good efficacy. But temperature was the limiting factor: the predatory mite needed a minimal temperature of 18 degrees C to obtain good results. Further research is necessary to search for predatory mites that can be used in winter conditions (lower temperatures, less light).

  20. Molecular mechanisms of Tetranychus urticae chemical adaptation in hop fields

    PubMed Central

    Piraneo, Tara G.; Bull, Jon; Morales, Mariany A.; Lavine, Laura C.; Walsh, Douglas B.; Zhu, Fang

    2015-01-01

    The two-spotted spider mite, Tetranychus urticae Koch is a major pest that feeds on >1,100 plant species. Many perennial crops including hop (Humulus lupulus) are routinely plagued by T. urticae infestations. Hop is a specialty crop in Pacific Northwest states, where 99% of all U.S. hops are produced. To suppress T. urticae, growers often apply various acaricides. Unfortunately T. urticae has been documented to quickly develop resistance to these acaricides which directly cause control failures. Here, we investigated resistance ratios and distribution of multiple resistance-associated mutations in field collected T. urticae samples compared with a susceptible population. Our research revealed that a mutation in the cytochrome b gene (G126S) in 35% tested T. urticae populations and a mutation in the voltage-gated sodium channel gene (F1538I) in 66.7% populations may contribute resistance to bifenazate and bifenthrin, respectively. No mutations were detected in Glutamate-gated chloride channel subunits tested, suggesting target site insensitivity may not be important in our hop T. urticae resistance to abamectin. However, P450-mediated detoxification was observed and is a putative mechanism for abamectin resistance. Molecular mechanisms of T. urticae chemical adaptation in hopyards is imperative new information that will help growers develop effective and sustainable management strategies. PMID:26621458

  1. Regression analysis of dynamics of insecticide resistance in field populations of Chilo suppressalis (Lepidoptera: Crambidae) during 2002-2011 in China.

    PubMed

    He, Yueping; Zhang, Juefeng; Gao, Congfen; Su, Jianya; Chen, Jianming; Shen, Jinliang

    2013-08-01

    To understand the evolution of insecticide resistance in the Asiatic rice borer, Chilo suppressalis (Walker) (Lepidoptera: Crambidae), in field, regression analysis based on a linear or nonlinear model was adopted for analyzing resistance dynamics to six insecticides of two field populations of the Lianyungang (LYG) and Ruian (RA) populations during 2002-2011. For the low-level resistance population, LYG population, sustained susceptibilities to abamectin and fipronil were seen for 10 yr; a polynomial curve regression model showed an increase in resistance to chlorpyrifos; exponential growth models fit to the resistance dynamics to triazophos and deltamethrin, and a sigmoidal growth curve for monosultap. For the high-level multiple resistance population, RA population, a slight increase from susceptible to a minor resistance to abamectin could be modeled by a polynomial cubic equation; an exponential growth model fit to the increase of resistance to fipronil from 8.7-fold to 33.6-fold; a sine waveform model fit to the vibrating tendency of resistance to chlorpyrifos; the dynamics of resistance to triazophos could be modeled by two combined curves, with a polynomial growth model and a sine waveform model; the high level of resistance to monosultap could be modeled with a sine waveform model; and a significant linear growth relationship of the resistance to deltamethrin of the RA population over years was found. Then, the relationship between dynamics of resistance development to insecticides among the field populations of C. suppressalis and the application history of pesticides for controlling rice borers was discussed.

  2. Multiresidue method for simultaneous analysis of aflatoxin M1, avermectins, organophosphate pesticides and milbemycin in milk by ultra-performance liquid chromatography coupled to tandem mass spectrometry.

    PubMed

    Dos Anjos, Marianna Ramos; Castro, Izabela Miranda de; Souza, Maria de Lourdes Mendes de; de Lima, Virgínia Verônica; de Aquino-Neto, Francisco Radler

    2016-06-01

    A method developed for the simultaneous analysis of aflatoxin M1, abamectin, doramectin, eprinomectin, ivermectin, moxidectin, acephate, azinphos-ethyl, azinphos-methyl, diazinon, methamidophos, methidathion, mevinphos, pirimiphos-ethyl and pirimiphos-methyl in whole raw milk, based on the QuEChERS method for extraction and clean-up, with detection and quantification by ultra-performance liquid chromatography coupled to tandem mass spectrometry (UPLC-MS/MS) is described. The method was validated according to parameters of the Analytical Quality Assurance Manual from the Brazilian Ministry of Agriculture and Commission Decision 2002/657/EC, and proved suitable for analysis of these analytes within the proposed working range, with recovery values between 77% and 110%, a standard deviation lower than 20%, limits of detection between 0.05 and 0.99 µg l(-)(1), and limits of quantification between 0.15 and 1.98 µg l(-1). Samples from animals treated with abamectin, doramectin, ivermectin and diazinon were analysed by the validated method. Residues of aflatoxin M1 were also found in field samples at levels below the established maximum residue limit.

  3. Curative and Residual Efficacy of Injection Applications of Avermectins for Control of Plant-parasitic Nematodes on Banana

    PubMed Central

    Jansson, Richard K.; Rabatin, Susan

    1997-01-01

    Studies were conducted to determine the curative and residual efficacy of avermectins at controlling plant-parasitic nematodes when injected into the pseudostem of banana, Musa acuminata cv. Cavendish. In addition, we determined the lowest concentration of avermectins that provided satisfactory efficacy as protectants when injected into banana pseudostems. Experiments were conducted with a root-knot nematode, Meleidogyne javanica, and the burrowing nematode, Radopholus similis. Injections (1 ml) of ≥ 100 μg a.i./plant of abamectin into pseudostems were effective at controlling M. javanica and R. similis, and were comparable to control achieved with a conventional chemical nemaficide, fenamiphos, in a protectant assay. Abamecfin injections of 250 and 500 μg a.i./plant were effective at reducing nematode infections 28 to 56 days after inoculation. Abamectin was more effective than ivermectin at controlling nematodes after nematode populations were established in banana roots. Injections of between 100 and 1,000 μg a.i./plant were effective at controlling nematodes for at least 56 days after treatment. These studies confirmed earlier results and demonstrated that abamecfin has potential for controlling nematode parasites on banana when injected into the pseudostem. PMID:19274271

  4. Resistance Monitoring for Eight Insecticides on the Sweetpotato Whitefly (Hemiptera: Aleyrodidae) in China.

    PubMed

    Wang, Shaoli; Zhang, Youjun; Yang, Xin; Xie, Wen; Wu, Qingjun

    2017-03-01

    The sweetpotato whitefly, Bemisia tabaci (Gennadius), is an important pest of many crops worldwide. Because control of B. tabaci still depends on the application of insecticides in China, monitoring the insecticide resistance of B. tabaci populations is essential for achieving control and for managing resistance. In this study, field populations of B. tabaci on vegetables were collected in three regions of China in 2011, 2012, and 2013. The resistance of these populations (all of which were determined to belong to biotype Q) to eight insecticides (abamectin, spinetoram, imidacloprid, thiamethoxam, acetamiprid, nitenpyram, chlorpyrifos, and bifenthrin) was assessed by the leaf-dip method. No resistance to abamectin and spinetoram was detected. All of the B. tabaci populations exhibited resistance to neonicotinoid insecticides; the resistance was 3.6- to 125.0-fold greater than that of a susceptible reference strain. The traditional insecticides chlorpyrifos and bifenthrin had very low toxicity. Bemisia tabaci specimens in some regions exhibited annual differences in resistance to some of the insecticides. The data presented will be helpful for making decisions on the proper insecticide usage in the field.

  5. Behavior of Tamarixia triozae Females (Hymenoptera: Eulophidae) Attacking Bactericera cockerelli (Hemiptera: Triozidae) and Effects of Three Pesticides on This Parasitoid.

    PubMed

    Martinez, Ana-Mabel; Chavarrieta, Juan-Manuel; Morales, Sinue-Isabel; Caudillo, Kiela-Briseida; Figueroa, José-Isaac; Diaz, Ovidio; Bujanos, Rafael; Gomez, Benjamín; Viñuela, Elisa; Pineda, Samuel

    2015-02-01

    The parasitism and host feeding behavior of Tamarixia triozae (Burks) (Hymenoptera: Eulophidae) females on Bactericera cockerelli (Sulc) (Hemiptera: Triozidae) fourth instars that have infested tomato (Lycopersicon esculentum Miller) leaflets are described and quantified. Females took approximately 31.14 ± 4.39 min to search for their first suitable host. The recognition and handling times for oviposition were 2.66 ± 0.18 and 4.26 ± 0.39 min, respectively. T. triozae parasitized 4.66 ± 0.61 nymphs in a period of 6 h. The parasitoid explored and probed its host by walking along the margins of its body while antennating and repeatedly introducing the ovipositor beneath the nymph. The handling times before and during host feeding were 8.42 ± 0.67 and 8.29 ± 0.60 min, respectively. T. triozae females consumed 1.00 ± 0.00 B. cockerelli nymph after parasitizing 3.3 ± 0.48 nymphs. EPA-a refined soybean oil-imidacloprid, and abamectin caused between ~70 and 100% T. triozae adult mortality after a 48-h contact treatment with fresh pesticide residue and a 47-91% decrease (abamectin > imidacloprid > EPA) in adult emergence when parasitized B. cockerelli fourth instars were directly sprayed. These data suggest that the use of these insecticides in combination with T. triozae in integrated pest management programs should be carefully evaluated.

  6. Functional Analysis of Esterase TCE2 Gene from Tetranychus cinnabarinus (Boisduval) involved in Acaricide Resistance

    PubMed Central

    Shi, Li; Wei, Peng; Wang, Xiangzun; Shen, Guangmao; Zhang, Jiao; Xiao, Wei; Xu, Zhifeng; Xu, Qiang; He, Lin

    2016-01-01

    The carmine spider mite, Tetranychus cinnabarinus is an important pest of crops and vegetables worldwide, and it has the ability to develop resistance against acaricides rapidly. Our previous study identified an esterase gene (designated TCE2) over-expressed in resistant mites. To investigate this gene’s function in resistance, the expression levels of TCE2 in susceptible, abamectin-, fenpropathrin-, and cyflumetofen-resistant strains were knocked down (65.02%, 63.14%, 57.82%, and 63.99%, respectively) via RNA interference. The bioassay data showed that the resistant levels to three acaricides were significantly decreased after the down-regulation of TCE2, indicating a correlation between the expression of TCE2 and the acaricide-resistance in T. cinnabarinus. TCE2 gene was then re-engineered for heterologous expression in Escherichia coli. The recombinant TCE2 exhibited α-naphthyl acetate activity (483.3 ± 71.8 nmol/mg pro. min−1), and the activity of this enzyme could be inhibited by abamectin, fenpropathrin, and cyflumetofen, respectively. HPLC and GC results showed that 10 μg of the recombinant TCE2 could effectively decompose 21.23% fenpropathrin and 49.70% cyflumetofen within 2 hours. This is the first report of a successful heterologous expression of an esterase gene from mites. This study provides direct evidence that TCE2 is a functional gene involved in acaricide resistance in T. cinnabarinus. PMID:26725309

  7. Genetics, cross-resistance and mechanism of resistance to spinosad in a field strain of Musca domestica L. (Diptera: Muscidae).

    PubMed

    Khan, Hafiz Azhar Ali; Akram, Waseem; Shad, Sarfraz Ali

    2014-02-01

    The house fly, Musca domestica L., is a cosmopolitan insect with the ability to develop resistance to insecticides used for their management. In the present study, we investigated the genetics of spinosad resistance, and cross-resistance potential to other insecticides by selecting a field strain with a commercial spinosad formulation. Bioassays with the field strain, before selection with spinosad, gave resistance ratios (RRs) of 4, 5, 66, 21 and 5 fold for spinosad, indoxacarb, abamectin, imidacloprid and deltamethrin, respectively, in comparison to a laboratory susceptible (Lab-susceptible) strain. After continuous selection of the field strain (Spin-SEL) with spinosad, the RR was increased up to 155 fold; however, the resistance was unstable (RR decreased 1.43 fold) when this strain was not exposed to spinosad for five generations. The Spin-SEL strain did not show cross-resistance to abamectin, indoxacarb or deltamethrin, but showed negative cross-resistance to imidacloprid. Crosses between the Spin-SEL and Lab-susceptible strains revealed an autosomal and incomplete dominant mode of resistance to spinosad. A direct test using a monogenic inheritance model based on Chi-square analysis revealed that the resistance was governed by more than one gene. Moreover, the resistance was neither overcome with the insecticide synergist piperonyl butoxide nor with S,S,S-tributylphosphorotrithioate. Lack of cross-resistance and instability of resistance suggest that rotation with spinosad could be an effective resistance management strategy.

  8. Attractiveness of insecticide baits for cockroach control (Dictyoptera: Blattellidae): laboratory and field studies.

    PubMed

    Nalyanya, G; Liang, D; Kopanic, R J; Schal, C

    2001-06-01

    Several insecticide bait formulations were evaluated for their attractiveness to cockroaches in olfactometer assays in the laboratory and in trapping experiments in the field. Included in the assays were bait stations, gels, pastes, and a powder that contained one of the following active ingredients: abamectin, boric acid, chlorpyrifos, or hydramethylnon. There were significant differences among the baits in their attractiveness to the German cockroach, Blattella germanica (L.). In trapping experiments, Avert powder (abamectin), Maxforce station and gel, and Siege gel (all hydramethylnon) were consistently attractive to B. germanica adults and nymphs. Laboratory olfactometer assays with adult males confirmed these results and showed that nymphs were as responsive as males whereas females were less responsive. Our bioassays also demonstrate that attractiveness of bait can be dramatically affected by the age of the bait. One week of aging significantly reduced the attractiveness of Avert powder in both laboratory and field assays. Aging, however did not diminish the attractiveness of Maxforce gel, indicating that the formulation may be critical for retention of attractiveness of baits. Baits that were most attractive to the German cockroach were also the most attractive to nymphs and adults of the brownbanded cockroach, Supella longipalpa (F.).

  9. Laboratory and field performance of an indoxacarb bait against German cockroaches (Dictyoptera: Blattellidae).

    PubMed

    Appel, Arthur G

    2003-06-01

    Experimental indoxacarb powder and gel baits were evaluated in the laboratory, and a gel bait was evaluated in subsequent field studies against the German cockroach, Blattella germanica (L.). In continuous exposure tests, LT50 values were 1.90 and 1.10 d for 0.25 and 1% indoxacarb powder baits, respectively. However, 0.25% indoxacarb gel bait had an LT50 value of 0.68 d, similar to a 0.05% abamectin gel bait formulated with the same bait base. There was no difference in toxicity between fresh and 7-d-old gel bait deposits. A pyrethroid-resistant strain of German cockroaches was significantly resistant to both abamectin and indoxacarb gel baits. Gel bait contained approximately 40% water, desiccated rapidly at 25-28 degrees C and 30-45% RH, but did not rehydrate when held at 56.7% RH for 3 d. Powder indoxacarb baits contained <1% water and did not desiccate or gain water. Indoxacarb gel bait (0.25%) was relatively nonrepellent (approximately 30%) and had positive maximum performance index values (approximately 100) in Ebeling choice box experiments. In field experiments in cockroach-infested kitchens, the 0.25% indoxacarb gel bait significantly reduced visual counts of German cockroaches approximately 74% at 3 d and >95% at 14 d. Indoxacarb baits are toxic, relatively nonrepellent, and can significantly reduce German cockroach populations.

  10. Control of root-knot nematodes on tomato in stone wool substrate with biological nematicides.

    PubMed

    López-Pérez, Jose Antonio; Edwards, Scott; Ploeg, Antoon

    2011-06-01

    The efficacy of four biological nematicides on root-galling, root-knot nematode (Meloidogyne incognita) reproduction, and shoot weight of tomato (Solanum lycopersicum) grown in stone wool substrate or in pots with sandy soil was compared to an oxamyl treatment and a non-treated control. In stone wool grown tomato, Avid® (a.i. abamectin) was highly effective when applied as a drench at time of nematode inoculation. It strongly reduced root-galling and nematode reproduction, and prevented a reduction in tomato shoot weight. However, applying the product one week before, or two weeks after nematode inoculation was largely ineffective. This shows that Avid® has short-lived, non-systemic activity. The effects of Avid® on nematode symptoms and reproduction on soil-grown tomato were only very minor, probably due to the known strong adsorption of the active ingredient abamectin to soil particles. The neem derived product Ornazin® strongly reduced tomato root-galling and nematode reproduction only in stone wool and only when applied as a drench one week prior to nematode inoculation, suggesting a local systemic activity or modification of the root system, rendering them less suitable host for the nematodes. This application however also had some phytotoxic effect, reducing tomato shoot weights. The other two products, Nema-Q™ and DiTera®, did not result in strong or consistent effects on nematode symptoms or reproduction.

  11. Curative and Residual Efficacy of Injection Applications of Avermectins for Control of Plant-parasitic Nematodes on Banana.

    PubMed

    Jansson, R K; Rabatin, S

    1997-12-01

    Studies were conducted to determine the curative and residual efficacy of avermectins at controlling plant-parasitic nematodes when injected into the pseudostem of banana, Musa acuminata cv. Cavendish. In addition, we determined the lowest concentration of avermectins that provided satisfactory efficacy as protectants when injected into banana pseudostems. Experiments were conducted with a root-knot nematode, Meleidogyne javanica, and the burrowing nematode, Radopholus similis. Injections (1 ml) of >/= 100 mug a.i./plant of abamectin into pseudostems were effective at controlling M. javanica and R. similis, and were comparable to control achieved with a conventional chemical nemaficide, fenamiphos, in a protectant assay. Abamecfin injections of 250 and 500 mug a.i./plant were effective at reducing nematode infections 28 to 56 days after inoculation. Abamectin was more effective than ivermectin at controlling nematodes after nematode populations were established in banana roots. Injections of between 100 and 1,000 mug a.i./plant were effective at controlling nematodes for at least 56 days after treatment. These studies confirmed earlier results and demonstrated that abamecfin has potential for controlling nematode parasites on banana when injected into the pseudostem.

  12. Synthesis and decomposition of a novel carboxylate precursor to indium oxide

    NASA Technical Reports Server (NTRS)

    Hepp, Aloysius F.; Andras, Maria T.; Duraj, Stan A.; Clark, Eric B.; Hehemann, David G.; Scheiman, Daniel A.; Fanwick, Phillip E.

    1994-01-01

    Reaction of metallic indium with benzoyl peroxide in 4-1 methylpyridine (4-Mepy) at 25 C produces an eight-coordinate mononuclear indium(III) benzoate, In(eta(sup 2)-O2CC6H5)3(4-Mepy)2 4H2O (I), in yields of up to 60 percent. The indium(III) benzoate was fully characterized by elemental analysis, spectroscopy, and X-ray crystallography; (I) exists in the crystalline state as discrete eight-coordinate molecules; the coordination sphere around the central indium atom is best described as pseudo-square pyramidal. Thermogravimetric analysis of (I) and X-ray diffraction powder studies on the resulting pyrolysate demonstrate that this new benzoate is an inorganic precursor to indium oxide. Decomposition of (I) occurs first by loss of 4-methylpyridine ligands (100 deg-200 deg C), then loss of benzoates with formation of In2O3 at 450 C. We discuss both use of carboxylates as precursors and our approach to their preparation.

  13. Comparative 16S rRNA gene surveys of granular sludge from three upflow anaerobic bioreactors treating purified terephthalic acid (PTA) wastewater.

    PubMed

    Perkins, S D; Scalfone, N B; Angenent, L T

    2011-01-01

    The microbial communities from three upflow anaerobic bioreactors treating purified terephthalic acid (PTA) wastewater were characterized with 16S ribosomal RNA gene sequencing surveys. Universal bacterial and archaeal primers were used to compare the bioreactor communities to each other. A total of 1,733 bacterial sequences and 383 archaeal sequences were characterized. The high number of Syntrophus spp. and Pelotomaculum spp. found within these reactors indicates efficient removal of benzoate and terephthalate. Under anaerobic conditions benzoate can be degraded through syntrophic associations between these bacteria and hydrogen-scavenging microbes, such as Desulfovibrio spp. and hydrogenotrophic methanogens, which remove H(2) to force the thermodynamically unfavourable reactions to take place. The authors did not observe a relatively high percentage of hydrogenotrophic methanogens with the archaeal gene survey because of a high acetate flux (acetate is a main component in PTA wastewater and is the main degradation product of terephthalate/benzoate fermentation), and because of the presence of Desulfovibrio spp. (a sulfate reducer that scavenges hydrogen). The high acetate flux also explains the high percentage of acetoclastic methanogens from the genus Methanosaeta among the archaeal sequences. A group of uncultured bacteria (OD1) may be involved in the degradation of p-toluate (4-methyl benzoate), which is a component of PTA wastewater.

  14. Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives.

    PubMed

    Feng, Pengju; Ngai, Ming-Yu

    2016-01-19

    Molecules bearing trifluoromethoxy (OCF3) group often show desired pharmacological and biological properties. However, facile synthesis of trifluoromethoxylated aromatic compounds remains a formidable challenge in organic synthesis. Conventional approaches often suffer from poor substrate scope, or require use of highly toxic, difficult-to-handle, and/or thermally labile reagents. Herein, we report a user-friendly protocol for the synthesis of methyl 4-acetamido-3-(trifluoromethoxy)benzoate using 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one (Togni reagent II). Treating methyl 4-(N-hydroxyacetamido)benzoate (1a) with Togni reagent II in the presence of a catalytic amount of cesium carbonate (Cs2CO3) in chloroform at RT afforded methyl 4-(N-(trifluoromethoxy)acetamido)benzoate (2a). This intermediate was then converted to the final product methyl 4-acetamido-3-(trifluoromethoxy)benzoate (3a) in nitromethane at 120 °C. This procedure is general and can be applied to the synthesis of a broad spectrum of ortho-trifluoromethoxylated aniline derivatives, which could serve as useful synthetic building blocks for the discovery and development of new pharmaceuticals, agrochemicals, and functional materials.

  15. Allylic oxidation of steroidal olefins by vanadyl acetylacetonate and tert-butyl hydroperoxide.

    PubMed

    Grainger, Wendell S; Parish, Edward J

    2015-09-01

    Readily available vanadyl acetylacetonate was found to oxidize the allylic sites of Δ(5) steroidal alcohols without protection of hydroxyl groups. Cholesterol, dehydroepiandrosterone, cholesterol benzoate, cholesterol acetate, pregnenolone, and 5-pregnen-3,20-diene were oxidized to 7-keto products using vanadyl acetylacetonate in one pot reactions at room temperature in the presence of oxygen and water.

  16. In vitro and In vivo Studies on Stilbene Analogs as Potential Treatment Agents for Colon Cancer

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Based upon the potential of resveratrol as a cancer chemopreventive agent, 27 stilbenes analogs were synthesized and tested against colon cancer cell line HT-29. Among these compounds, amino derivative (Z)-4-(3,5-dimethoxystyryl) aniline (4), (Z)-methyl 4-(3,5-dimethoxystyryl) benzoate (6) and (Z)-1...

  17. Incorporation of preservatives in polylactic acid films for inactivating E. coli O157:H7 and extending microbiological shelf-life of strawberry puree

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Antimicrobial films of polylactic acid polymer incorporated with nisin, Ethylenediaminetetraacetic acid (EDTA), sodium benzoate (SB), potassium sorbate (PS) and their combination were developed and their antimicrobial effects on the inactivation of Escherichia coli O157:H7 and natural background mic...

  18. Variable Denticity in Carboxylate Binding to the Uranyl Coordination Complexes

    SciTech Connect

    G. S. Groenewold; W. A. de Jong; J. Oomens; M. J. van Stipdonk

    2010-05-01

    Tris-carboxylate complexes of the uranyl [UO2]2+ cation with acetate and benzoate were generated using electrospray ionization mass spectrometry, and then isolated in a Fourier transform ion cyclotron resonance mass spectrometer. Wavelength-selective infrared multiple photon dissociation (IRMPD) of the tris-acetatouranyl anion resulted in a redox elimination of an acetate radical, which was used to generate an IR spectrum that consisted of six prominent absorption bands. These were interpreted with the aid of density functional theory calculations in terms of a symmetric and antisymmetric –CO2 stretches of both the monodentate and bidentate acetate, CH3 bending and umbrella vibrations, and a uranyl OUO asymmetric stretch. The comparison of the calculated and measured IR spectra indicated that the tris-acetate complex contained two acetate ligands bound in a bidentate fashion, while the third acetate was monodentate. In similar fashion, the tris-benzoate uranyl anion was formed and photodissociated by loss of a benzoate radical, enabling measurement of the infrared spectrum that was in close agreement with that calculated for a structure containing one monodentate, and two bidentate benzoate ligand.

  19. 21 CFR 82.6 - Certifiable mixtures.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... and, in the case of mixtures which are aqueous solutions or aqueous pastes, sodium benzoate in a... 21 Food and Drugs 1 2011-04-01 2011-04-01 false Certifiable mixtures. 82.6 Section 82.6 Food and... PROVISIONALLY LISTED COLORS AND SPECIFICATIONS General Provisions § 82.6 Certifiable mixtures. (a) A batch of...

  20. 21 CFR 82.6 - Certifiable mixtures.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... and, in the case of mixtures which are aqueous solutions or aqueous pastes, sodium benzoate in a... 21 Food and Drugs 1 2010-04-01 2010-04-01 false Certifiable mixtures. 82.6 Section 82.6 Food and... PROVISIONALLY LISTED COLORS AND SPECIFICATIONS General Provisions § 82.6 Certifiable mixtures. (a) A batch of...