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

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

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1302-1307
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume32
Issue number6
DOIs
Publication statusPublished - Sep 1984
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Fingerprint Dive into the research topics of 'Resolution and Stereoselective Action of Sulprofos and Related S-propyl Phosphorothiolates'. Together they form a unique fingerprint.

  • Cite this