Synthesis of Optically Active Cyclic Phosphorothionates and Phosphoramidothionates with Insecticidal Activity by Using a Chiral Phosphorylating Agent

Abstract

Chiral methyl p-nitrophenyl phosphorochloridothionate (MNPC) was utilized as a phosphorylating agent in the synthesis of optically active cyclic phosphorus esters including the enantiomers of 2-methoxy-4H-1, 3, 2-benzodioxaphosphorin 2-sulfide (salithion) and four diastereomers of 4-isobutyl-2-methoxy-1, 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.