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Vinclozolin Structural Formula
Vinclozolin Structural Formula
CAS Number: 50471-44-8
Synonyms: BAS 352F, Ronilan, Vorlan
Contaminant Type: Chemical

Vinclozolin is a synthetic organic compound of the imide group of the dicarboximide class of fungicides. Its IUPAC name is 3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione. Vinclozolin has been registered for use in the United States since 1981, and is manufactured by BASF Corporation. Prior to 2000, it was used to control various diseases on raspberries, lettuce, kiwi, canola, snap beans, dry bulb onions, ornamental plants, and turf. [1443] However, in order to mitigate risk associated with the use of vinclozolin, USEPA accepted a proposal submitted by the registrant which included a phase out of all domestic food uses of vinclozolin except for use on canola, and revocation of all import tolerances except for wine grapes. [1443]

Vinclozolin is not regulated by USEPA in drinking water, but is an unregulated chemical drinking water contaminant listed on the USEPA's Contaminant Candidate List 3. [620]

Vinclozolin generally has been shown to have low acute oral/dermal/inhalation toxicity and that the principal toxic effects induced by vinclozolin and/or its metabolites are related to its antiandrogenic activity. [1443] Studies show that vinclozolin may have minimal antiandrogenic activity at relevant dose levels but that at least two vinclozolin metabolites occurring in mammals, plants, and soil and are responsible for much of the antiandrogenic activity attributable to vinclozolin. Vinclozolin exerts its effects most dramatically during the developmental stages of animals ultimately resulting in negative reproductive effects. Since the androgen receptor is widely conserved across species lines, antiandrogenic effects would be expected in humans. [1443] However, the human consequences are unknown. There is also evidence in published literature that vinclozolin may affect the development and function of the neuroendocrine system. It has been determined that vinclozolin's terminal metabolite, 3,5-dichloroaniline (3,5-DCA), should be regulated based on potential carcinogenic concerns. [1443]

Vinclozolin degrades in the environment by microbial-mediated hydrolysis, abiotic degradation, and transport with water. The principal degradation products of vinclozolin are metabolite B, metabolite E, which is believed to be a degradation product of parent and metabolite B, and 3,5-dichloroaniline (3,5-DCA), which is a degradation product of metabolite E. [1443] Experimental evidence has shown 3,5-DCA to be resistant to degradation processes. Vinclozolin and its principal degradates are potentially very mobile to slightly mobile in soil. Metabolites B, E and 3,5-DCA may be transported with water through the soil profile or with surface runoff. Residues are likely to be most mobile in sandy soils low in organic matter. [1443]

Date of Literature Search: June 2009

620 USEPA Office of Ground Water and Drinking Water; 2008; Contaminant Candidate List 3 (CCL3); USEPA Office of Ground Water and Drinking Water; http://www/epa.gov/OGWDW/ccl/ccl3.html
1443 USEPA; 2000; R.E.D. Facts - Vinclozolin; R.E.D. Facts - Vinclozolin; EPA Report 738-F-00-021. Prevention, Pesticides And Toxic Substances.

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