Chlorfenvinphos

Title: Chlorfenvinphos
CAS Registry Number: 470-90-6
CAS Name: Phosphoric acid 2-chloro-1-(2,4-dichlorophenyl)ethenyl diethyl ester
Additional Names: O,O-diethyl O-[2-chloro-1-(2,4-dichlorophenyl)vinyl] phosphate; 2,4-dichloro-a-(chloromethylene)benzyl alcohol diethyl phosphate; CVP
Manufacturers' Codes: SD-7859; Compd 4072
Trademarks: Birlane (BASF); Steladone (Syngenta); Supona (BASF)
Molecular Formula: C12H14Cl3O4P
Molecular Weight: 359.57
Percent Composition: C 40.08%, H 3.92%, Cl 29.58%, O 17.80%, P 8.61%
Literature References: Organophosphorous insecticide; acetylcholinesterase inhibitor. Commercial prepn contains at least 90% of the active Z-isomer. Prepn: E. E. Gilbert et al., US 3003916 (1961 to Allied Chemical); Phillips et al., US 3102842 (1963 to Shell); Whetstone, Phillips et al., J. Agric. Food Chem. 14, 352 (1966). Metabolism: W. F. Chamberlain, D. E. Hopkins, J. Econ. Entomol. 55, 86 (1962); D. H. Hotson et al., Biochem. J. 102, 133 (1967). Toxicity studies: A. M. Ambrose et al., Toxicol. Appl. Pharmacol. 17, 323 (1970); Bunyan et al., Pestic. Sci. 2, 148 (1971). Review of toxicology and human exposure: Toxicological Profile for Chlorfenvinphos (PB98-101116, 1997) 220 pp.
Properties: Amber liquid, mild odor, bp0.001 120°, bp0.5 167-170°. Vapor press at 25°C: 7.5 ´ 10-6 mm Hg. nD25 1.5272. Soly in water at 23°: 145 ppm. Miscible with acetone, ethanol, propylene glycol. Slowly hydrolyzed by water. Corrosive to metal. LD50 in rats (mg/kg): 6.6 i.v.; 9.66 orally (Ambrose).
Boiling point: bp0.001 120°; bp0.5 167-170°
Index of refraction: nD25 1.5272
Toxicity data: LD50 in rats (mg/kg): 6.6 i.v.; 9.66 orally (Ambrose)
CAUTION: Potential symptoms of overexposure are headache, dizziness, weakness, feeling of anxiety, confusion, runny nose, constriction of pupils, blurred vision, nausea, vomiting, abdominal cramps, slow pulse, diarrhea, difficulty breathing, fainting (PB98-101116).
Use: Insecticide; acaricide.
Chlorhexadol Chlorhexidine Chloric Acid Chlorimuron-ethyl Chlorinated Lime

Chlorfenvinphos
Chlorfenvinphos Structures V.1.svg
Identifiers
CAS number 470-90-6 (EZ) YesY, 18708-86-6 (E) YesY, 18708-87-7 (Z) YesY
PubChem 5377784
ChemSpider 4526760 YesY
UNII F2G9XS1W91 YesY
EC number 207-432-0
Jmol-3D images Image 1
Properties
Molecular formula C12H14Cl3O4P
Molar mass 359.57 g mol−1
Appearance Amber liquid
Solubility in water 145 mg/L
Hazards
LD50 15  mg/kg (rat, oral)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chlorfenvinphos is the common name of an organophosphorus compound that was widely used as an insecticide and an acaricide.[2] The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic 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 cancelled in 1991.[3]

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.[4]