VINCLOZOLIN

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H9Cl2NO3
Molecular Weight	286.111
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(OC(=O)N(C1=O)C2=CC(Cl)=CC(Cl)=C2)C=C

InChI

InChIKey=FSCWZHGZWWDELK-UHFFFAOYSA-N

InChI=1S/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Distribution of multiple pesticide residues in apple segments after home processing.	2003 Nov	14668155
Effects of vinclozolin administration on sperm production and testosterone biosynthetic pathway in adult male rat.	2003 Oct	14967917
Analysis of pesticide residues in lettuce by large volume-difficult matrix introduction-gas chromatography-time of flight-mass spectrometry (LV-DMI-GC-TOF-MS).	2003 Oct	14667157
Endocrine disruption and hypospadias.	2004	15086029
Determination of impurities in pesticides and their degradation products formed during the wine-making process by solid-phase extraction and gas chromatography with detection by electron impact mass spectrometry. I. Vinclozoline, procymidone and fenitrothion.	2004	15052576
Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells.	2004 Apr	15064155
Testosterone-stimulated weanlings as an alternative to castrated male rats in the Hershberger anti-androgen assay.	2004 Apr	15041151
First evidence of endocrine disruption in feral carp from the Ebro River.	2004 Apr 15	15081271
High-resolution image cytometry of rat sperm nuclear shape, size and chromatin status. Experimental validation with the reproductive toxicant vinclozolin.	2004 Aug-Sep	15279875
Effect of the anti-androgenic endocrine disruptor vinclozolin on embryonic testis cord formation and postnatal testis development and function.	2004 Aug-Sep	15279874
Effects of endocrine disrupters on sex steroid synthesis and metabolism pathways in fish.	2004 Dec	15698553
Cloning and in vitro expression and characterization of the androgen receptor and isolation of estrogen receptor alpha from the fathead Minnow (Pimephales promelas).	2004 Dec 1	15597887
Parameters affecting extraction of selected fungicides from vineyard soils.	2004 Dec 1	15563199
Sensitive trace enrichment of environmental andiandrogen vinclozolin from natural waters and sediment samples using hollow-fiber liquid-phase microextraction.	2004 Dec 17	15633739
Screening of some anti-androgenic endocrine disruptors using a recombinant cell-based in vitro bioassay.	2004 Feb	15084347
Short-time exposure to vinclozolin in utero induces testicular maldescent associated with a spinal nucleus alteration of the genitofemoral nerve in rats.	2004 Feb	14966744
The effect of a prenatal androgen disruptor, vinclozolin, on gubernacular migration and testicular descent in rats.	2004 Feb	14966743
Phthalate ester-induced gubernacular lesions are associated with reduced insl3 gene expression in the fetal rat testis.	2004 Feb 2	14687758
Reproductive disorders in pubertal and adult phase of the male rats exposed to vinclozolin during puberty.	2004 Jul	15297758
Comparison of anti-androgenic activity of flutamide, vinclozolin, procymidone, linuron, and p, p'-DDE in rodent 10-day Hershberger assay.	2004 Jul 1	15147789
Determination of organochlorine compounds in human biological samples by GC-MS/MS.	2004 Mar	15039962
Interactive effects of vinclozolin and testosterone propionate on pregnancy and sexual differentiation of the male and female SD rat.	2004 Mar	14736997
Effects of vinclozolin on spermatogenesis and reproductive success in the Japanese quail (Coturnix coturnix japonica).	2004 May	15253051
Interlaboratory comparison of four in vitro assays for assessing androgenic and antiandrogenic activity of environmental chemicals.	2004 May	15121513
Androgenic and estrogenic response of green mussel extracts from Singapore's coastal environment using a human cell-based bioassay.	2004 Nov	15531429
The effects of the reported active metabolite of methoxychlor, 2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane, on testosterone formation by cultured Leydig cells from young adult rats.	2004 Nov	15336722
Cytotoxicity of the dicarboximide fungicides, vinclozolin and iprodione, in rat hepatoma-derived Fa32 cells.	2004 Oct	15651921
Study on failures to disclose conflicts of interest in Environmental Health Perspectives.	2004 Oct	15471711
Anogenital distance in human male and female newborns: a descriptive, cross-sectional study.	2004 Sep 13	15363098
Liquid chromatography determination of the anti-androgen vinclozolin and its metabolites in rat serum.	2004 Sep 25	15282099
Growth spurt for EDC recognition.	2005 Aug	16106568
Consequences of endocrine disrupting chemicals on reproductive endocrine function in birds: establishing reliable end points of exposure.	2005 Aug	15998506
Myelotoxicity in genistein-, nonylphenol-, methoxychlor-, vinclozolin- or ethinyl estradiol-exposed F1 generations of Sprague-Dawley rats following developmental and adult exposures.	2005 Aug 1	15925024
CAR and PXR: xenosensors of endocrine disrupters?	2005 Aug 15	16054614
The flavoring agent dihydrocoumarin reverses epigenetic silencing and inhibits sirtuin deacetylases.	2005 Dec	16362078
Evidence of detrimental effects of environmental contaminants on growth and reproductive physiology of white sturgeon in impounded areas of the Columbia River.	2005 Dec	16330346
Determination and validation of a simple high-performance liquid chromatographic method for simultaneous assay of iprodione and vinclozolin in human urine.	2005 Dec 15	16203187
Antiandrogenic effects in short-term in vivo studies of the fungicide fenarimol.	2005 Feb 1	15590119
Cancer incidence among glyphosate-exposed pesticide applicators in the Agricultural Health Study.	2005 Jan	15626647
Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays.	2005 Jan	15483189
Gene expression analysis in the ventral prostate of rats exposed to vinclozolin or procymidone.	2005 Jan-Feb	15686871
Endocrine-disrupting chemicals probed as potential pathways to illness.	2005 Jul 20	16030264
Evaluation of the rodent Hershberger bioassay using three reference (anti)androgens.	2005 Jun	15968828
Perinatal exposure to low levels of the environmental antiandrogen vinclozolin alters sex-differentiated social play and sexual behaviors in the rat.	2005 Jun	15929892
Epigenetic transgenerational actions of endocrine disruptors and male fertility.	2005 Jun 3	15933200
Developmental biology. Endocrine disrupters trigger fertility problems in multiple generations.	2005 Jun 3	15933166
Photodegradation of chlorinated pesticides dispersed on sand.	2005 Mar	15686762
Evaluation of phenylaminopyrimidines as antifungal protein kinase inhibitors.	2005 Nov	15952247
Are EDCs blurring issues of gender?	2005 Oct	16203228
Vinclozolin, a widely used fungizide, enhanced BaP-induced micronucleus formation in human derived hepatoma cells by increasing CYP1A1 expression.	2005 Oct 15	15979257

Patents

Name

Type

Language

VINCLOZOLIN

Common Name

English

VINCLOZOLIN, (±)-

Common Name

English

VINCLOZOLIN [ISO]

Common Name

English

RONILAN

Brand Name

English

3-(3,5-DICHLOROPHENYL)-5-ETHENYL-5-METHYL-2,4-OXAZOLIDINEDIONE

Systematic Name

English

VORLAN

Common Name

English

(±)-3-(3,5-DICHLOROPHENYL)-5-ETHENYL-5-METHYL-2,4-OXAZOLIDINEDIONE

Systematic Name

English

VINCLOZOLIN [MI]

Common Name

English

VINCLOZOLIN [HSDB]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

113201