Vinclozolin
Vinclozolin (trade names Ronilan, Curalan, Vorlan, Touche) is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, lettuce, kiwi, snap beans, and onions.In addition to these restrictions within the United States, as of 2006 the use of this pesticide was banned in several countries, including Denmark, Finland, Norway, and Sweden.The following is a compilation of data indicating the national use of vinclozolin per crop (lbs AI/yr) in 1987: apricots, 124; cherries, 3,301; green beans, 13,437; lettuce, 24,779; nectarines, 1,449; onions, 829; peaches, 15,203; plums, 163; raspberries, 3,247; and strawberries, 41,006.[4] In 1997, two applications totaling 285 pounds each, were applied to kiwifruit in California to prevent the gray mold and soft rot caused by Botrytis cinerea.[6] The following chemical reactions are used to make vinclozolin:[7] One method combines methyl vinyl ketone, sodium cyanide, 3,5-dichloroaniline, and phosgene.[10] It has been determined that people may be exposed to residues of vinclozolin and its metabolites containing the 3,5-dichloroaniline moiety (3,5-DCA) through diet, and thus tolerance limits have been established for each crop.The main effect induced by vinclozolin is related to its antiandrogenic activity and its ability to act as a competitive antagonist of the androgen receptor.[12] In bird models, vinclozolin and its metabolites were shown in vitro and in vivo to inhibit androgen receptor binding and gene expression.[8] In vertebrates, vinclozolin also acts as a neuroendocrine disruptor, affecting behaviors tied to locomotion, cognition, and anxiety.After three generations, male offspring continued to show low sperm count, prostate disease and high rates of testicular cell apoptosis.The New York State Agricultural Experiment Station has carried out efficacy trials for gray and white mold.Switch was the most promising alternative to vinclozolin for controlling both gray and white mold on pods and for increasing marketable yield.
IUPAC nameCAS NumberChEMBLChemSpiderECHA InfoCardPubChemCompTox DashboardSMILESChemical formulaMolar massstandard statedicarboximide fungicideBotrytis cinereaSclerotinia sclerotiorumUnited States Environmental Protection Agencyendocrine disruptorantiandrogenicmethyl vinyl ketonesodium cyanide3,5-dichloroanilinephosgenecyanohydrinisocyanatecompetitive antagonistandrogen receptorhypospadiassteroid hormone receptorsprogesteroneestrogenvirilizationapoptosisleydig celliprodionefludioxonilThiophanate-methylBibcodemodulators4-Androstenediol4-Dehydroepiandrosterone (4-DHEA)4-Hydroxytestosterone5-Androstenedione11-Ketotestosterone11β-HydroxyandrostenedioneAdrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)Androstenediol (5-androstenediol)Androstenediol 3β-acetateAndrostenediol 17β-acetateAndrostenediol diacetateAndrostenediol dipropionateAndrostenedione (4-androstenedione)AtamestaneBoldenoneBoldenone undecylenateBoldione (1,4-androstadienedione)ClostebolClostebol acetateClostebol caproateClostebol propionateCloxotestosteroneCloxotestosterone acetateDehydroandrosteroneDHEA (androstenolone, prasterone; 5-DHEA)DHEA enanthate (prasterone enanthate)DHEA sulfateExemestaneFormestanePlomestaneQuinboloneSilandroneTestosterone+dutasteridePolytestosterone phloretin phosphate1-Androstenediol1-Androstenedione1-Androsterone (1-andro, 1-DHEA)1-Testosterone3α-Androstanediol5α-Androst-2-en-17-one7β-Hydroxyepiandrosterone11-KetodihydrotestosteroneAndrosteroneBolazineBolazine capronateDihydrofluoxymesteroneDihydrotestosterone (DHT)androstanolone, stanoloneDrostanoloneDrostanolone propionateEpiandrosteroneEpitiostanolMepitiostaneMesaboloneMesteroloneMesterolone cipionateMethyldiazinolNisterimeNisterime acetateProstanozolStenboloneStenbolone acetateTestifenon (testiphenon, testiphenone)7α-Methyl-19-norandrostenedione (MENT dione, trestione)11β-Methyl-19-nortestosterone11β-Methyl-19-nortestosterone dodecylcarbonate19-Nor-5-androstenediol19-Nor-5-androstenedione19-NordehydroepiandrosteroneBolandiolBolandiol dipropionateBolandione (19-nor-4-androstenedione)Bolmantalate (nandrolone adamantoate)DienedioneDienoloneDimethandroloneDimethandrolone buciclateDimethandrolone dodecylcarbonateDimethandrolone undecanoateLS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)Methoxydienone (methoxygonadiene)NandroloneNorclostebolNorclostebol acetateNormethandrone (methylestrenolone, normethisterone)OxaboloneOxabolone cipionate (oxabolone cypionate)Trenbolone