2089. Chlorfenvinphos

Nomenclature

CAS number: 470-90-6
Phosphoric acid 2-chloro-1-(2,4-dichlorophenyl)ethenyl diethyl ester; 2-chloro-1-(2,4-dichlorophenyl)vinyl diethyl phosphate; O,O-diethyl O-[2-chloro-1-(2,4-dichlorophenyl)vinyl] phosphate; 2,4-dichloro-α-(chloromethylene)benzyl alcohol diethyl phosphate; CVP; SD-7859; GC-4072; Birlane (BASF); Steladone (Zagro); Supona (BASF).
C12H14Cl3O4P; mol wt 359.57.
C 40.08%, H 3.92%, Cl 29.58%, O 17.80%, P 8.61%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Commercial prepn contains at least 90% of the active (Z)-isomer. Prepn: E. E. Gilbert et al., US 3003916 (1961 to Allied Chemical); R. R. Whetstone et al., J. Agric. Food Chem. 14, 352 (1966) DOI. Dermal absorption and metabolism in cattle: W. F. Chamberlain, D. E. Hopkins, J. Econ. Entomol. 55, 86 (1962). GLC determn in animal tissue: M. C. Ivey et al., J. Agric. Food Chem. 21, 822 (1973) DOI PubMed. Toxicity studies: A. M. Ambrose et al., Toxicol. Appl. Pharmacol. 17, 323 (1970) DOI PubMed. Persistence in soil: K. I. Beynon, A. N. Wright, J. Sci. Food Agric. 18, 143 (1967) DOI PubMed. Review of toxicology and human exposure: Toxicological Profile for Chlorfenvinphos (PB98-101116, 1997) 220 pp.

Chemical structure

Properties

Amber liquid, mild odor. Poisonous. 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).

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.

Therapeutic Category (Veterinary)

Ectoparasiticide.