6165. Mevinphos

Nomenclature

CAS number: 7786-34-7
3-[(Dimethoxyphosphinyl)oxy]-2-butenoic acid methyl ester; 3-hydroxycrotonic acid methyl ester dimethyl phosphate; 1-methoxycarbonyl-1-propen-2-yl dimethyl phosphate; methyl 3-(dimethoxyphosphinyloxy)crotonate; O,O-dimethyl 1-carbomethoxy-1-propen-2-yl phosphate; 2-carbomethoxy-1-methylvinyl dimethyl phosphate; ENT-22374; OS-2046; Phosdrin (AMVAC).
C7H13O6P; mol wt 224.15.
C 37.51%, H 5.85%, O 42.83%, P 13.82%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Commercial product is a mixture of isomers, containing ≈60% of the more active (E)- (also referred to as cis-) isomer. Prepn: A. R. Stiles, US 2685552 (1954 to Shell). Activity: R. A. Corey et al., J. Econ. Entomol. 46, 386 (1953); of isomers: J. E. Casida et al., J. Agric. Food Chem. 4, 236 (1956) DOI. Configuration of isomers: T. R. Fukuto et al., J. Org. Chem. 26, 4620 (1961) DOI. 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. GC-MS determn in animal tissue: W. J. Allender, J. Keegan, J. Chromatogr. 609, 315 (1992) DOI PubMed.

Chemical structure

Properties

Yellow liquid. d420 1.25. nD20 1.4494. bp1 106-107.5°. Poisonous. Misc with water, acetone, benzene, carbon tetrachloride, chloroform, ethyl and isopropyl alcohols, toluene and xylene. One gram dissolves in 20 ml carbon disulfide and 20 ml kerosene. Practically insol in hexane. LD50 in female, male rats (mg/kg): 3.7, 6.1 orally; 4.2, 4.7 dermally (Gaines).

Caution

Potential symptoms of overexposure are miosis; rhinorrhea; headache; tight chest, wheezing, laryngeal spasm, salivation and cyanosis; anorexia, nausea, vomiting, abdominal cramps and diarrhea; paralysis; ataxia, convulsions; low blood pressure, cardiac irregularities; irritation of skin, eyes and respiratory system. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 252.

Use

Insecticide.