2600. Crotoxyphos

Nomenclature

CAS number: 7700-17-6
(2E)-3-[(Dimethoxyphosphinyl)oxy]-2-butenoic acid 1-phenylethyl ester; (E)-3-hydroxycrotonic acid α-methylbenzyl ester dimethyl phosphate; 1-phenylethel (E)-3-[(dimethoxyphosphinyl)oxy]-2-butenoate; Ciodrin; ENT-24717; SD-4294.
C14H19O6P; mol wt 314.27.
C 53.50%, H 6.09%, O 30.55%, P 9.86%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: GB 855238 (1960 to Bataafse Petroleum Maatschappij N.V.); Whetstone, Stiles, US 2982686 (1961 to Shell). Activity: C. P. Weidenback, R. L. Younger, J. Econ. Entomol. 55, 793 (1962). Metabolism and degradn: K. I. Beynon et al., Residue Rev. 47, 55 (1973) PubMed. Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969) DOI PubMed.

Chemical structure

Properties

Light straw-colored liq, bp0.03 135°. nD25 1.4988. d25 1.19. Poisonous. Vapor pressure at 20°: 1.4 × 10-5 mm Hg. Soly in water at room temp: 0.1%. Slightly sol in kerosine, saturated hydrocarbons. Sol in acetone, chloroform, ethanol, highly chlorinated hydrocarbons. LD50 in female, male rats (mg/kg): 74, 110 orally (Gaines).

Use

Insecticide.

Therapeutic Category (Veterinary)

Ectoparasiticide.