| Record Information |
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| Version | 1.0 |
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| Creation Date | 2013-04-25 07:56:55 UTC |
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| Update Date | 2016-11-09 01:08:59 UTC |
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| Accession Number | CHEM002903 |
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| Identification |
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| Common Name | Vinclozolin |
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| Class | Small Molecule |
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| Description | 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. It is also used on turf on golf courses. Two common fungi that vinclozolin is used to protect crops against are botrytis cinerea and sclerotinia scleotiorun. First registered in 1981, vinclozolin is widely used but its overall application has declined. As a pesticide, vinclozolin is regulated by the United States Environmental Protection Agency (U.S. EPA). It has gone through a series of tests and regulations in order to evaluate the risks and hazards to the environment and animals. Among the research, a main finding is that vinclozolin has been shown to be an endocrine disruptor with antiandrogenic effects. |
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| Contaminant Sources | - Clean Air Act Chemicals
- HPV EPA Chemicals
- My Exposome Chemicals
- STOFF IDENT Compounds
- T3DB toxins
- ToxCast & Tox21 Chemicals
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| Contaminant Type | - Amide
- Amine
- Carbamate
- Ester
- Ether
- Fungicide
- Organic Compound
- Organochloride
- Pesticide
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 3-(3,5-Dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione | MeSH | | Ronilan | MeSH |
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| Chemical Formula | C12H9Cl2NO3 |
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| Average Molecular Mass | 286.111 g/mol |
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| Monoisotopic Mass | 284.996 g/mol |
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| CAS Registry Number | 50471-44-8 |
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| IUPAC Name | 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-1,3-oxazolidine-2,4-dione |
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| Traditional Name | vinclozolin |
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| SMILES | CC1(OC(=O)N(C1=O)C1=CC(Cl)=CC(Cl)=C1)C=C |
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| InChI Identifier | 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 |
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| InChI Key | FSCWZHGZWWDELK-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Halobenzenes |
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| Direct Parent | Dichlorobenzenes |
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| Alternative Parents | |
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| Substituents | - 1,3-dichlorobenzene
- Oxazolidinedione
- Aryl chloride
- Aryl halide
- Oxazolidinone
- Dicarboximide
- Oxazolidine
- Carbamic acid ester
- Carbonic acid derivative
- Carboxylic acid derivative
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- Carbonyl group
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ug0-9240000000-bf89f1f40075773094c2 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-00di-0900000000-c0e2e62c921a42b43ce7 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-00di-0900000000-4ca08b47b3259fbd8b41 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-02or-0970000000-9694f61d4f6098f1c1b0 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-00di-0920000000-de70432cb5cf65b3c319 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-02ti-0190000000-095efceffc704e6077b2 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-000i-0090000000-c98c4e21d4b81274112a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-b3300389257f8faff5ca | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gbi-9030000000-06d3f48418764eb1a617 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9000000000-942d3569d2c68aa5db43 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000000-7ac69daa2d2d030d875b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0090000000-758f586c440fea004f5e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-1900000000-4cdfab3c8d249dc4f7e7 | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-01p9-7980000000-95f8d8d8e2f4e48d2ccd | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Vinclozolin and some of its metabolites have antiandrogenic activity. Vinclozolin's main toxic effects are related to its antiandrogenic activity. They compete with androgens for the androgen receptor, inhibit androgen receptor-DNA binding, and alter androgen-dependent gene expression. |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | This is a man-made compound that is used as a pesticide. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0259811 |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Vinclozolin |
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| Chemspider ID | 36278 |
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| ChEBI ID | 83732 |
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| PubChem Compound ID | Not Available |
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| Kegg Compound ID | C10981 |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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