Ethyl-1-(14)C-ethion and some of its degradation products have been prepared for comparison purposes. Cotton plants were treated with (14)C-ethion alone and in the presence of deltamethrin and dimilin pesticides under conditions simulating local agricultural practice. (14)C-Residues in seeds were determined at harvest time; about 47.5% of (14)C-activity was associated with oil. After further extraction of seeds with ethanol, the ethanol-soluble (14)C-residues accounted for 10.6% of the total seed residues, whereas the cake contained about 37.3% of the total residues as bound residues in the case of ethion only. The bound residues decreased in the presence of deltamethrin and dimilin pesticides and amounted to 8.1 and 10.4% of the total residues, respectively. About 95% of the (14)C-activity in the crude oil could be eliminated by simulated commercial processes locally used for oil refining. Chromatographic analysis of crude cotton oil revealed the presence of ethion monooxon, O,O-diethyl phosphorothioate, and O,O-diethyl phosphoric acid in addition to one unknown compound in the case of ethion alone or ethion and dimilin. The same degradation products are found in the case of ethion and deltamethrin in addition to ethion dioxon, whereas ethanol extract revealed the presence of ethion dioxon and O,O-diethyl phosphoric acid as free metabolites. Acid hydrolysis of the conjugated metabolites in the ethanol extract yielded O,O-diethyl S-hydroxymethyl phosphorodithioate. The bound residues were quite readily bioavailable to the rats. After feeding rats with the cake containing ethion-bound residues, a substantial amount (60%) of (14)C-residues was eliminated in the urine, whereas the (14)C-residues excreted in expired air and feces were 10 and 9%, respectively. About 11% of the radioactive residues were distributed among various organs.
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