title: Development of insecticidal cyclic phosphoryl compounds through chemical and biochemical approaches.
abstract: Chemical and biochemical studies on three types of cyclic phosphoryl compounds are discussed in connection with the development of insecticides. They are five-membered cyclic phosphoramidates (I), six-membered cyclic phosphates (II) and bridged bicyclic phosphates (III). Development of I has started from the finding of L-leucine as a neuroactive substance in silkworm blood, followed by its combination with chemically active five-membered cyclic phosphates. Studies on the metabolism of neurotoxic tri-o-tolyl phosphate caused the invention of the insecticide salithion in the series of II. Salithion was chemically converted into its thiolo isomers, which is a convenient phosphorylating agent useful to synthesize biologically interesting phosphate esters. III does not inhibit acetylcholin-esterase but acts as an anti-GABA agent.
mesh_terms: D000596:Amino Acids; D000818:Animals; D001592:Benzyl Alcohols; D055598:Chemical Phenomena; D002621:Chemistry; D002800:Cholinesterase Inhibitors / Q000494:pharmacology; D006793:Houseflies; D007313:Insecta; D007306:Insecticides / Q000138:chemical synthesis / Q000494:pharmacology; D007930:Leucine; D008968:Molecular Conformation; D010755:Organophosphates / Q000494:pharmacology; D063086:Organothiophosphates / Q000494:pharmacology; D010526:Periplaneta; D010766:Phosphorylation; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D001592:Benzyl Alcohols; D002800:Cholinesterase Inhibitors; D007306:Insecticides; D010755:Organophosphates; D063086:Organothiophosphates; C032089:salioxon; C032070:salithion; C010631:salicyl alcohol; D007930:Leucine