Vinclozolin is a dicarboximide fungicide widely used in Europe and the United States for control of diseases caused by B. cineera, S. sclerotiorum, and Monilinia species in grapes, fruits, vegetables, ornamental plants, and turfgrass.1 Metabolites of vinclozolin, M1 and M2, are effective antagonists of the androgen receptor in rats exhibiting Ki values of 92 and 9.7 µM respectively.2 In fathead minnow, M1 and M2 failed to compete for high-affinity, low capacity testosterone binding sites in brain and ovary cytosolic fractions suggesting that they are not anti-androgens in this species.3
1
Pothuluri, J.V., Freeman, J.P., Heinze, T.M., et al. Biotransformation of vinclozolin by the fungus Cunninghemella elegans. J Agric Food Chem486138-6148(2000).
2
Kelce, W.R., Monosson, E., Gamcsik, M.P., et al. Enviromental hormone disruptors: Evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites. Toxicol Appl Pharmacol126276-285(1994).
3
Makynen, E.A., Kahl, M.D., Jensen, K.M., et al. Effects of the mammalian antiandrogen vinclozolin on development and reproduction of the fathead minnow. Aquat Toxicol48461-475(2000).
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C=CC(C)(O)C(=O)Nc1cc(Cl)cc(Cl)c1
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Pothuluri, J.V., Freeman, J.P., Heinze, T.M., et al. Biotransformation of vinclozolin by the fungus Cunninghemella elegans. J Agric Food Chem486138-6148(2000).
Makynen, E.A., Kahl, M.D., Jensen, K.M., et al. Effects of the mammalian antiandrogen vinclozolin on development and reproduction of the fathead minnow. Aquat Toxicol48461-475(2000).
Kelce, W.R., Monosson, E., Gamcsik, M.P., et al. Enviromental hormone disruptors: Evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites. Toxicol Appl Pharmacol126276-285(1994).
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