3220. Dimethoate

Nomenclature

CAS number: 60-51-5
Phosphorodithioic acid O,O-dimethyl S-[2-(methylamino)-2-oxoethyl] ester; phosphorodithioic acid O,O-dimethyl ester, ester with 2-mercapto-N-methylacetamide; O,O-dimethyl S-methylcarbamoylmethyl phosphorodithioate; American Cyanamid 12880; Danadim (Cheminova); Perfekthion (BASF); Rogor (Isagro).
C5H12NO3PS2; mol wt 229.26.
C 26.19%, H 5.28%, N 6.11%, O 20.94%, P 13.51%, S 27.97%.

Description and references

Organophosphate insecticide; cholinesterase inhibitor. Prepn: Cassaday et al., Young, US 2494283 and US 2996531 (1950, 1961, both to Am. Cyanamid); GB 791824 (1958 to Montecatini), C.A. 52, 18222 (1958). LC-MS/MS determn in blood: P. Salm et al., J. Chromatogr. B 877, 568 (2009) DOI PubMed. Degradation study: L. Zhang et al., J. Hazard. Mater. 149, 675 (2007) DOI PubMed. Toxicity data: E. W. Schafer, Toxicol. Appl. Pharmacol. 21, 315 (1972) DOI PubMed. Teratogenicity study: K. D. Courtney et al., J. Environ. Sci. Health B20, 373 (1985).

Chemical structure

Properties

Crystals, mp 52-52.5°. d65 1.277. nD65 1.5334. Burns readily on contact with flame. Very slightly sol in water. Freely sol in most organic solvents, except saturated hydrocarbons. Stable in aq soln; hydrolyzed by aq alkali. LD50 orally in rats: 250 mg/kg (Schafer).

Use

Acaricide; insecticide.