Abstract
α-Cyano-3-phenoxybenzyl 2, 2, 3, 3-tetramethylcyclopropanecarboxylate (fenpropathrin), a new potent synthetic pyrethroid, was labelled with carbon-14 at the cyclopropyl group for studies on its metabolism in mammals, fishes, plants and soils. Condensation of potassium cyanide-14C (2) with 1, 3-diphenyl-2-thiourea (3) in the presence of basic lead carbonate gave 1-eyano-14C-N, N'-diphenylformamidine (4) . Reduction of 4 followed by hydrolysis with barium hydroxide afforded glycine-2-14C (6) . Esterification of 6 with ethanol in the presence of anhydrous hydrogen chloride gave ethyl glycinate-2-14C hydrochloride (7) . Diazotization of 7 followed by condensation with 2, 3-dimethyl-2-butene yielded ethyl 2, 2, 3, 3-tetramethylcyclopropane-1-14C-earboxylate (8) . Hydrolysis of 8 gave 2, 2, 3, 3-tetramethylcyclopropane-1-14C-carboxylic acid (9), which was esteri feed with a-eyano-3-phenoxybenzyl bromide (10) to afford fenpropathrin- (cyelopropyl-1-14C) (1) in 13% yield from 2.
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