Reference

Stereoselectivity in metabolism of the optical isomers of cyanofenphos (O-p-cyanophenyl O-ethyl phenylphosphonothioate) in rats and liver microsomes

Stereoselectivity in metabolism of the optical isomers of cyanofenphos (O-p-cyanophenyl O-ethyl phenylphosphonothioate) in rats and liver microsomes.Some chemicals with cas registry numbers like 62421-63-0 and 62421-61-8 are also used. Ohkawa, Hideo; Mikami, Nobuyoshi; Miyamoto, Junshi (Pestic. Div., Sumitomo Chem. Co., Ltd., Takarazuka, Japan). Agric. Biol. Chem., 41(2), 369-76 (English) 1977. CODEN: ABCHA6. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) Racemic (+)- [62421-63-0] and (-)-cyanofenphos (O-p-cyanophenyl O-ethyl phenylphosphonothioate) [62421-61-8] were rapidly metabolized in the rat by cleavage of the P-O-aryl linkage, cleavage of the P-O-alkyl linkage, and conjugation of p-cyanophenol [767-00-0] with sulfuric acid. There was a marked difference in the proportion of the major urinary metabolites, p-cyanophenol and p-cyanophenyl sulfate [31377-14-7], with 3 forms of cyanofenphos (I). The 3 forms of I were metabolized at almost equal rates in rat liver microsomes-NADPH system. (+)-Cyanofenphos underwent oxidn. of P:S to P:O and cleavage of the P-O-aryl linkage predominantly. In contrast, the (-)-isomer was converted to the corresponding oxon analog [62266-03-9] by mixed function oxidase, and then the oxon analog was rapidly hydrolyzed to p-cyanophenol by microsomal arylesterase-type enzyme. This microsomal enzyme had a remarkable selectivity in hydrolyzing (-)-cyanofenphos oxon vs. the (+)-isomer. Stereoselectivity in the metab. of the I isomers in the rat appears likely to be mainly due to selective hydrolysis of the (-)-oxon analog by the arylesterase-type enzyme. .

Photodecomposition of Surecide (O-ethyl O-4-cyanophenylphosphonothioate) and Cyanox (O,O-dimethyl O-4-cyanophenyl phosphorothioate)

Photodecomposition of Surecide (O-ethyl O-4-cyanophenylphosphonothioate) and Cyanox (O,O-dimethyl O-4-cyanophenyl phosphorothioate). Mikami, Nobuyuki; Ohkawa, Hideo; Miyamoto, Junshi (Sumitomo Chem. Co., Takarazuka, Japan). Nippon Noyaku Gakkaishi, 1(4), 271-81 (English) 1976. CODEN: NNGADV. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemicals) Surecide (I) [13067-93-1] and Cyanox (II) [2636-26-2] underwent rapid photodecompn. in Me2CO when exposed to UV light for 60-240 min. Photodecompn. products detected were: HCN, CO2, 4-cyanophenol [767-00-0], O-Et phenylphosphoric acid [4546-19-4], I and II P:O analogs, 4-cyano- [619-65-8] and 2-hydroxy-5-cyanobenzoic acid [10435-57-1], and desmethylcyanox oxon (III) [31328-16-2]. I and III (in water and on soil and silica gel) were more slowly decompd. in sunlight than in UV light, although decompn. in water was slower than on solid surface; HCN and CO2 were not formed from I or II in sunlight. Principal photodecompn. products formed in sunlight were the oxon analogs, 4-cyanophenol, and III. Sunlight may significantly promote I and II decompn.Except for chemicals metioned above, 2636-26-2 and 619-65-8 are also used. .