9192. Tetrachlorvinphos

Nomenclature

CAS number: 22248-79-9
Phosphoric acid (Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl ester; (Z)-2-chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate; stirofos; ENT-25841; SD-8447; Equitrol (Farnam); Gardona (BASF); Rabon (Wyeth); Rabond (Wyeth).
C10H9Cl4O4P; mol wt 365.96.
C 32.82%, H 2.48%, Cl 38.75%, O 17.49%, P 8.46%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: D. D. Phillips, L. F. Ward, Jr., US 3102842; D. E. Ramey, US 3553297 (1963, 1971 both to Shell). Properties: R. R. Whetstone et al., J. Agric. Food Chem. 14, 352 (1966) DOI. Metabolism in cows: M. H. Akhtar, T. S. Foster, ibid. 28, 698 (1980) DOI PubMed. Pharmacology in horses: J. Berger et al., Vet. Res. Commun. 32, 75 (2008) DOI PubMed. Determn of residues in foods: V. Leoni et al., J. AOAC Int. 75, 511 (1992). Toxicology studies: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969) DOI PubMed; A. I. T. Walker et al., Pestic. Sci. 3, 517 (1972) DOI. Review of agricultural use: A. G. Jennings, Int. Pest Control 12, 28-33 (1970); of carcinogenic risk: IARC Monographs 30, 197-206 (1983).

Chemical structure

Properties

mp 97-98°. Vapor pressure at 20° = 4.2 × 10-8. Soly: 11 ppm in water; <15% in xylene; 40-50% in chloroform at room temp. LD50 in male, female rats (mg/kg): 1100, 1125 orally (Gaines).

Use

Insecticide.

Therapeutic Category (Veterinary)

Ectoparasiticide.