Dimethylphosphorothioates. Reaction with malathion and effect on malathion toxicity.
Five dimethylphosphorothioates were tested for their toxicity to rats, potentiation of malathion toxicity in rats, inhibition of carboxylesterase in vitro, and reaction with malathion in vitro. The compounds were: potassium salts of (CH3S)2P(O)O-(I), (CH3O)(CH3S)P(O)S-(II), (CH3O)2P(O)S-(III), (CH3O)2P(S)S-(IV), and (CH3O)(CH3S)P(O)O-(V). The dimethylphosphorothioates are not toxic to rats (up to 1 g/kg, orally), they do not potentiate malathion toxicity in rats, and do not inhibit carboxylesterase activity in vitro (up to 1 mM concentrations). However, when the S-acid diesters (II, III, IV) are incubated with malathion for serveral days at room temperature or for several hours at 50 degrees C they become methylated forming the trimethylphosphorothioates OSS-trimethyl phosphorodithioate, OOS-trimethyl phosphorothioate and OOS-trimethyl phosphorodithioate respectively, which potentiate malathion toxicity. Furthermore, these same acid diesters increase the rate of isomerization of malathion into OS-dimethyl-S-(1,2-dicarbethoxyethyl) phosphorodithioate (isomalathion) particularly, diester IV. The formation of the trimethylphosphorothioates and isomalathion from the interaction of the S-acid diesters with malathion was determined by thin layer chromatography (TLC), gas chromatography and mass spectrometry and could be detected by in vitro inhibition of carboxylesterase. TLC methods can detect 1 mg of the trimethylphosphorothioates and isomalathion per gram malathion.
D000818:Animals; D002265:Carboxylic Ester Hydrolases / Q000037:antagonists & inhibitors*; D002855:Chromatography, Thin Layer; D004357:Drug Synergism; D005260:Female; D006168:Guinea Pigs; D066298:In Vitro Techniques; D007928:Lethal Dose 50; D008294:Malathion / Q000633:toxicity*; D009946:Organothiophosphorus Compounds / Q000633:toxicity*; D051381:Rats
D009946:Organothiophosphorus Compounds; D002265:Carboxylic Ester Hydrolases; C021528:malathion esterases; D008294:Malathion