Synthesis of optically active cyclic phosphorothionates and phosphoramidothionates with insecticidal activityby using a chiral phosphorylating agent

Akinori Hirashima, Morifusa Eto

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Abstract

Chiral methyl/7-nitrophenyl phosphorochloridothionate (MNPC) was utilized as a phosphorylating agent in the synthesis of optically active cyclic phosphorus esters including the enantiomers of 2-methoxy-4#-l, 3, 2-benzodioxaphosphorin 2-sulfide (salithion) and four diastereomers of 4-isobutyl-2-methoxy-l, 3, 2-oxazaphospholidine 2-sulfide (BMOS). Their insecticidal activity decreased in the following order; (S) > (R) in salithion and (S)P(S)C > (S)P(R)C > (R)P(R)C >(R)P(S)C in BMOS.

Original languageEnglish
Pages (from-to)2831-2839
Number of pages9
JournalAgricultural and Biological Chemistry
Volume47
Issue number12
DOIs
Publication statusPublished - Dec 1983

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All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)
  • Agricultural and Biological Sciences(all)

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