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chlorfenvinphos
Sign in to saveAlso known as chlorfenvinfos, Chlorfenvinfos, O,O-Diethyl-O-1-(2',4'-dichloro-phenyl)-2-chlorovinyl-phosphate, 2,4-Dichloro-alpha-(chloromethylene)benzyl diethyl phosphate
Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphoric acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was discontinued in 1991.
Chemical data
- Formula
- C12H14Cl3O4P
- Molecular weight
- 359.6 g/mol
- IUPAC name
- [2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate
- SMILES
- CCOP(=O)(OCC)OC(=CCl)C1=C(C=C(C=C1)Cl)Cl
- InChIKey
- FSAVDKDHPDSCTO-UHFFFAOYSA-N
- XLogP
- 3.1
- Polar surface area
- 44.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
399 papers- PMID 376474611997
- Combined toxicities of binary mixtures of alachlor, chlorfenvinphos, diuron and isoproturon.Chemosphere · 2020
- Sorption/Desorption and Kinetics of Atrazine, Chlorfenvinphos, Endosulfan Sulfate and Trifluralin on Agro-Industrial and Composted Organic Wastes.Toxics · 2022
- Study of the chlorfenvinphos pesticide removal under different anodic materials and different reactor configuration.Chemosphere · 2022
- Comparison of supercritical fluid chromatography-tandem mass spectrometry and liquid chromatography-tandem mass spectrometry for the stereoselective analysis of chlorfenvinphos and dimethylvinphos in tobacco.Journal of separation science · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 357.969529
- Has use
- acaricide
Show 5 more facts
- chemical formula
- C₁₂H₁₄Cl₃O₄P
- canonical SMILES
- CCOP(=O)(OCC)OC(=CCl)C1=C(C=C(C=C1)Cl)Cl
- isomeric SMILES
- CCOP(=O)(OCC)O/C(=C/Cl)c1ccc(Cl)cc1Cl
- subject has role
- acetylcholinesterase inhibitor
- Commons category
- Chlorphenvinfos
Sources (2)
via Wikidata · CC0
~13 min read
Encyclopedic overview
16 sectionsContents
- Pesticide use
- History
- Regulation and advisories
- Production
- Toxicokinetics
- Mechanism of toxicity
- Toxicity
- Toxic effects
- Acute toxicity
- Long-term toxicity
- Biomarkers
- Biomarkers of exposure
- Biomarkers of effect
- Treatments of exposure
- References
- External links
Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphoric acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was discontinued in 1991.
The pure chemical is a colorless solid, but for commercial purposes, it is often marketed as an amber liquid. The insecticides, mostly used in liquid form, contain between 50% and 90% chlorfenvinphos. The substance easily mixes with acetone, ethanol, and propylene glycol. Furthermore, chlorfenvinphos is corrosive to metal and hydrolyzes in the environment.
Excerpted from Wikipedia’s “chlorfenvinphos” article, available under the CC BY-SA 4.0 licence.
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