Kinetic study of reversible conversion of methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl) to methyl 2-benzimidazolecarbamate (MBC) and butyl isocyanate (BIC) in organic solvents

Chiba, Mikio; Cherniak, E. A.

doi:10.1021/jf60217a015

Cited by 39 publications

(27 citation statements)

References 8 publications

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“…Based on these findings, the benomyl-induced increase in aromatase activity appears to be mainly regulated by the transcription of CYP19. Importantly, the rapidly produced metabolite of benomyl, carbendazim (15)(16)(17), was equally effective in stimulating aromatase activity. Thus, the effect of benomyl could be mediated by carbendazim, rather than benomyl itself, as suggested in benomyl-induced testicular toxicity (32).…”

Section: Discussionmentioning

confidence: 99%

“…Using this system, we screened 55 candidate chemicals for endocrine disruption in assays of aromatase activity and found that only benomyl [methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate], a benzimidazole fungicide commonly used on a variety of food crops and ornamental plants, induces aromatase activity in KGN cells. Benomyl is also able to interfere with the assembly of fungal microtubules (14), can rapidly degrade into carbendazim in aqueous (15) or organic (16) solutions, or as a result of hydroxylation in the microsomal monooxygenase system (17). In this study we investigated some of the mechanisms involved in benomylinduced aromatase activity in association with the properties stated above.…”

Section: )mentioning

confidence: 99%

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A Benzimidazole Fungicide, Benomyl, and Its Metabolite, Carbendazim, Induce Aromatase Activity in a Human Ovarian Granulose-Like Tumor Cell Line (KGN)

et al. 2004

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Endocrine disruptor chemicals are known to cause a range of abnormalities in sexual differentiation and reproduction. One mechanism underlying such effects may be via alteration of aromatase activity, which is responsible for estrogen production. A good screening system for identifying endocrine disruptors has long been desired. We have recently established a human ovarian granulosa-like tumor cell line, KGN, which possesses a relatively high level of aromatase expression and is considered a useful mammalian model for investigating the in vitro effects of various chemicals on aromatase activity. In this study we screened 55 different candidate chemicals for endocrine disruptors by assaying aromatase activity. Only benomyl, known as both a benzimidazole fungicide and a microtubule-interfering agent, was found to induce aromatase activity in association with increased levels of aromatase mRNA in KGN cells. The effect of benomyl was presumed to be mediated by its metabolite carbendazim, because it produced an effect equivalent to that of benomyl. The mechanism underlying the benomyl-induced increase in aromatase activity appears independent of the cAMP-protein kinase A pathway. Treatment with taxol, another class of microtubule-interfering agents, also caused induction of aromatase in KGN cells. Both benomyl and taxol changed KGN cell morphology, including the development of cell roundness and a disorganized network of microtubules. These results indicate that benomyl is a potential endocrine disruptor that provides a novel estrogenicity and operates through a microtubule-interfering mechanism.

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Section: Discussionmentioning

confidence: 99%

Section: )mentioning

confidence: 99%

A Benzimidazole Fungicide, Benomyl, and Its Metabolite, Carbendazim, Induce Aromatase Activity in a Human Ovarian Granulose-Like Tumor Cell Line (KGN)

et al. 2004

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“…Several authors studied the conversion of benomyl to carbendazim in aqueous and in partially aqueous solutions [3,4] as well as in common organic solvents [5]. Calmon and Sayag [3,4] determined the pseudo firstorder rate constants of benomyl decomposition to carbendazim, and they studied the dependence of pH on degradation rate in aqueous buffers-methanol (50:50, v/v) media.…”

Section: Introductionmentioning

confidence: 99%

Degradation study of benomyl and carbendazim in water by liquid chromatography and multivariate curve resolution methods

Mallat

Barceló²,

Tauler

1997

Chromatographia

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The degradation of benomyl and carbendazim in different organic solvents, distilled and ground waters was studied by on-line solid-phase extraction (SPE) followed by liquid chromatography (LC), diode array detection (DAD) or atmospheric pressure chemicalionization mass spectrometry detection (APCI-MS), UV spectrophotometry and multivariate curve resolution. Stability studies were performed in different organic solvents, such as acetonitrile and methanol, and in aqueous solution at different pH. Samples were stored in dark conditions at 4 ~ and analysed by LC-DAD over 10 days. Photodegradation products of benomyl were resolved by spectrophotometry and multivariate curve resolution between pH 3 to 9. These results were correlated with those from LC-DAD and LC-APCI-MS. Photolysis studies were carried out at low concentration levels (2 lag L -1) of carbendazim under different storage conditions in order to evaluate the effect of parameters, such as pH, temperature and sunlight exposure. Water samples (50 mL) were preconcentrated using on-line SPE-LC-DAD. Photodegradation products of benomyl and carbendazim were identified by on-line-SPE-LC-DAD and SPE-LC-APCI-MS, leading to identification of carbendazim, 3-butyl-2,4-dioxo-s-triazinol,2-abenzimidazole (STB) and 2-aminobenzimidazole (2-AB).

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“…Overall, among of tested antifungal agents, benomyl inhibited mycelial growth and conidia germination of the four Trichoderma species at all tested concentrations. Benomyl was reported to inhibit assembly of fungal microtubules (Davidse, 1986), rapidly degrade into carbendazim in aqueous (Tang et al, 1992) or organic (Chiba and Cherniak, 1978) solution, or induce hydroxylation in the microsomal monooxygenase system (Danielson and Davey, 1973). While, mushroom strains of Chamaram and Sanjo 701ho could grow at all the fungicide concentration (data not shown).…”

Section: Resultsmentioning

confidence: 99%

Isolation and Characterization of Airborne Mushroom Damaging Trichoderma spp. from Indoor Air of Cultivation Houses Used for Oak Wood Mushroom Production Using Sawdust Media

et al. 2019

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Kinetic study of reversible conversion of methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl) to methyl 2-benzimidazolecarbamate (MBC) and butyl isocyanate (BIC) in organic solvents

Cited by 39 publications

References 8 publications

A Benzimidazole Fungicide, Benomyl, and Its Metabolite, Carbendazim, Induce Aromatase Activity in a Human Ovarian Granulose-Like Tumor Cell Line (KGN)

A Benzimidazole Fungicide, Benomyl, and Its Metabolite, Carbendazim, Induce Aromatase Activity in a Human Ovarian Granulose-Like Tumor Cell Line (KGN)

Degradation study of benomyl and carbendazim in water by liquid chromatography and multivariate curve resolution methods

Isolation and Characterization of Airborne Mushroom Damaging Trichoderma spp. from Indoor Air of Cultivation Houses Used for Oak Wood Mushroom Production Using Sawdust Media

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