+)-Traps and (+)-cis isomers of phenothrin [3-phenoxybenzyl (+)-cis, traps-chrysanthemate] labeled with 14C at the methylene group of the alcohol moiety disappeared rapidly from the treated leaves of bean and rice plants with half-lives of less than one day under greenhouse conditions. On and/or in these plants, both isomers underwent ozonolysis at the isobutenyl double bond to yield ozonides of phenothrin isomers which were rapidly decomposed to the corresponding aldehydes and carboxylic acids. These ester products were further metabolized via cleavage of the ester linkage, hydroxylation at 2'-and 4'-positions of the alcohol moiety, and oxidation of benzyl alcohols to benzoic acids. The resulted alcohols and carboxylic acids were subsequently conjugated with sugars. Bean plant seedlings planted in Kodaira soil, Katano soil and Muko sand treated with 1. 0 ppm of 14C-phenothrin isomers took up very little 14C into shoots, and pods and seeds, whereas roots retained 0. 21-3. 48 ppm of 14C. No parent compounds were detected in shoots. 14C-Phenothrin isomers were rapidly decomposed in Kodaira and Katano soils with half-lives of 1 to 2 days under upland conditions. On the other hand, degradation of both isomers was much slower under flooded conditions, and half-lives were 2 to 4 weeks and 1 to 2 months for the (+ )-traps and (+)-cis isomers, . respectively.Degradation of phenothrin isomers in the soils proceeded via cleavage of the ester linkage, hydroxylation at 4'-position of the alcohol moiety, cleavage of the Biphenyl ether linkage and oxidation of benzyl alcohols to benzoic acids. These products were not persistent in the soils under both conditions and the labeled carbon was finally decomposed to 14CO2.
14C-Labeled (+)-traps and (+)-cis isomers of phenothrin [3-phenoxybenzyl (+)-cis, traps-chrysanthemate] were each applied at the concentration of 4 ppm to wheat grains 11% moisture content, and stored at 15 or 30C in the dark. Both traps and cis were decomposed slowly, and 79 and 87% of the applied radiocarbon remained intact in after 12-month storage at 30C, respectively. Both isomers majorly metabolized via hydrolysis of ester linkage, oxidation of the benzyl alcohol to the benzoic acid and of the benzoic acid. The joint application with piperonyl butoxide and fenitrothion inhed the degradation of phenothrin isomers to some extent. The phenothrin isomers and their decomposition products were mainly located at seed coat during 12-month storage, and residue levels of both isomers in flour and bran were 0.77 and 11.4 The phenothrin residues in flour somewhat decreased through the baking process, leaving of phenothrin isomers in bread. These findings were compared with those of 14C-m which was rapidly decomposed to desmethylmalathion, malathion-monoacids, -and 14CO2i with respective half-lives of 8 and 1.1 months at 15 and 30C .
3H-Cremart(R), O-ethyl O-(3-methyl-6-nitrophenyl) N-sec-butylphosphoramidothioate, labeled at the phenyl group is readily and substantially completely excreted, majorly into urine on oral administration to rat at 70 mg/kg. Less than 1% of Cremart initially given is present only in the feces, but no oxygen analog is detected in the excreta, although it is formed in the animal body. The major metabolites in the urine are 3-methyl-6-nitrophenol, 3-hydroxymethyl-6-nitrophenol and 3-carboxy-6-nitrophenol, free and conjugated with sulfuric and glucuronic acid, together with a trace amount in the excreta of the metabolites carrying intact P-0-C (aryl) linkage such as Cremart, 0-ethyl 0-(6-amino-3carboxyphenyl) N-sec-butylphosphoramidate, aminocremart and 0-ethyl 0-hydrogen 0-(3methyl-6-nitrophenyl)-phosphorothioate. No significant differences are observed between males and females in excretion and metabolism. Therefore, apparently Cremart is biodegradable and unlikely to leave any persistent residues in mammals. 3H-Cremart added to nutrient solution at 2. 0 ppm is steadily absorbed into bean plants, rice plants and carrots. The bulk of the absorbed 3H is present in the roots, and its level in the shoots is low. After 10-day cultivation Cremart accounts for 70 up to 85% of 3H absorbed in the plants, with other radioactive metabolites including cremart-oxon, 3methyl-6-nitrophenol as well as its glucoside and 0-ethyl 0-(3-hydroxymethyl-6-nitrophenyl) N-sec-butylphosphoramidothioate.
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