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 - Jan 1 1984

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sulprofos
profenofos
Sulfones
Musca domestica
Acetylcholinesterase
acetylcholinesterase
Diptera
Isomers
isomers
ethanolysis
Electrophorus
diastereomers
Detoxification
Enantiomers
Poisons
enantiomers
microsomes
Microsomes
Liver
Oxidoreductases

All Science Journal Classification (ASJC) codes

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

Cite this

Resolution and Stereoselective Action of Sulprofos and Related S-propyl Phosphorothiolates. / Hirashima, Akinori; Holden, Ian; Casida, John E.; Leader, Haim.

In: Journal of Agricultural and Food Chemistry, Vol. 32, No. 6, 01.01.1984, p. 1302-1307.

Research output: Contribution to journalArticle

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