Vinclozolin M2 (Synonyms: M2)

Vinclozolin is a dicarboximide fungicide widely used in Europe and the United States for control of diseases caused by B. cinerea, 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 K_i 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 elegansJ. Agric. Food Chem.48(12)6138-6148(2000) 2.Kelce, W.R., Monosson, E., Gamcsik, M.P., et al.Enviromental hormone disruptors: Evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolitesToxicol. Appl. Pharmacol.126(2)276-285(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 minnowAquatic Toxicology48461-475(2000)