Resolution and Stereoselective Action of Sulprofos and Related S-propyl Phosphorothiolates

Akinori Hirashima, Ian Holden, John E. Casida, Haim Leader

研究成果: Contribution to journalArticle査読

22 被引用数 (Scopus)

抄録

The enantiomers of sulprofos [O-ethyl O-[4-(methylthio)phenyl] S-propyl phosphorodithioate] and its phosphorothiolate analogue were prepared by acid-catalyzed ethanolysis of the diastereoisomers of N-[(2S)-2-(carboxyethyl)pyrrolidinyl] S-propyl phosphoramidodithioate and the corresponding phosphoramidothiolate, respectively. Peracid oxidation converted the phosphorodithioate and phosphorothiolate to the sulfone derivative of sulprofos oxon. Analogous procedures were used to resolve profenofos [O-(4-bromo-2-chlorophenyl) O-ethyl S-propyl phosphorothiolate] and its O-methyl and O-pentachlorophenyl analogues. The (+)-isomers are most toxic to house flies in the sulprofos series and the (-)-isomers in the profenofos series. The chiral specificity is reversed in each case relative to potency as inhibitors of house fly head acetylcholinesterase (AChE) activity. Most of these phosphorothiolates are activated to more potent inhibitors of electric eel AChE on coincubation with a mouse liver microsomal oxidase system. (+)-Profenofos and (-)-sulprofos oxon sulfone are the only exceptions, undergoing stereoselective detoxification when unwashed microsomes are used.

本文言語英語
ページ(範囲)1302-1307
ページ数6
ジャーナルJournal of Agricultural and Food Chemistry
32
6
DOI
出版ステータス出版済み - 9 1984
外部発表はい

All Science Journal Classification (ASJC) codes

  • 化学 (全般)
  • 農業および生物科学(全般)

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