Metabolism of Di-Syston by Insects, Isolated Cotton Leaves, and Rats1

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Abstract
Di-Syston (O,O-diethyl S[2-(ethylthio)ethyl] phosphorodithioate) was absorbed, metabolized, and excreted rapidly by fifth-instar bollworms, Heliothis zea (Boddie). and adult boll weevils. Anthonomus grandis Boheman. Insects excreted the toxic oxidative derivatives as well as the hydrolytic products of Di-Syston metabolism but was slowly excreted only hydrolytic products. As many as 4 oxidative and 9 hydrolytic metabolites of Di-Syston were detected in the biological systems used. The oxidative products included the sulfoxide and sulfone derivatives of Di-Syston and of the oxygen analog of Di-Syston. In animals and plants, the initial oxidative reaction with the Di-Syston molecule occurred at the mercapto sulfur atom. In plants, Di-Syston was converted almost quantitatively to its sulfoxide derivative during the first few minutes after treatment. The chief hydrolytic products of Di-Syston metabolism were diethyl phosphate and O,O-diethyl phosphorothioate. In addition, small concentrations of ethyl phosphate phosphoric acid, and 5 unidentified products were detected in certain samples. O,O-diethyl phosphorodithioate was not formed in insects or plants but trace amounts of the metabolite were detected in the urine of treated rats. Similar products were formed in the different biological systems but the rates of metabolicm varied considerably.

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