Saligenin Cyclic Methyl Phosphate and its Thiono Analogue: New Insecticides related to the Active Metabolite of Tri-o-cresyl Phosphate

Abstract

SALIGENIN cyclic phosphate was discovered as the active metabolite of tri-o-cresyl phosphate (TOCP) (ref. 1 and 2). Analogous cyclic phosphorus esters were synthetically prepared for examination of their chemical properties^3,4 and biological activities^5,6. The biological activity is not always coincidental with the chemical reactivity and appears to be influenced by the size of a substituent on phosphorus being outside the hetero-ring of the cyclic esters. The TOCP-metabolite causes ataxia in hens but has no insecticidal activity, while its analogous cyclic phosphates carrying a small alkyl group appear to have insecticidal activity. The following two esters are new promising insecticides in this unique series.