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Pyrethroid chemistry reactive alpha beta unsaturated keto aldehydes from peracid oxidation oxidative photodecomposition and metabolism of 5 benzyl 3 furylmethyl derivatives

Pyrethroid chemistry reactive alpha beta unsaturated keto aldehydes from peracid oxidation oxidative photodecomposition and metabolism of 5 benzyl 3 furylmethyl derivatives

Journal of Agricultural and Food Chemistry 33(4): 622-625

ISSN/ISBN: 0021-8561

DOI: 10.1021/jf00064a014

Oxidation of 5-benzyl-3-furylmethyl 2,2,3,3-tetramethylcyclopropanecarboxylate or the analogous methyl ether with 1.5 equiv of m-chloroperoxybenzoic acid proceeds by 4,5-addition, furan ring opening, and rearrangement to form the (Z)-2-[(acyloxy)methyl]-or (Z)-2(methoxymethyl)-4-keto-5-phenyl-2-pentenal, respectively, together with small amounts of the corresponding carboxylic acids. The 2-methoxymethyl keto aldehyde also forms in small yield on oxidative photodecomposition and microsomal metabolism. In biomimetic systems, both this methoxymethyl .alpha.,.beta.-unsaturated keto aldehyde and peracid-oxidized 5-benzyl-3-furylmethyl cis-chrysanthemate (resmethrin) form covalent derivatives with bovine serum albumin and the methoxymethyl keto aldehyde also forms a thioether derivative with 3,4-dichlorobenzenethiol. Oxidative furan ring opening of 5-benzyl-3-furylmethyl derivatives, including pyrethroids, may therefore contribute to their photochemical and metabolic lability and to tissue binding and persisting fragments in mammals. The 7a,.beta.-unsaturated keto aldehyde products are not detected as mutagens in several types of Salmonella typhimurium assays.

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