Pyrethroid photochemistry: mechanistic aspects in reactions of the (dihalogenovinyl)cyclopropanecarboxylate substituent
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 728-732
- https://doi.org/10.1039/p19800000728
Abstract
The reaction quantum yields of six pyrethroid insecticides in methanol at 300 nm vary 3–10-fold between compounds with a cyclopentenone chromophore (allethrin) as compared with the phenoxybenzyl group (e.g., permethrin, decamethrin) in the alcohol moiety. Chlorine confers greater photostability than bromine in pyrethroids with dihalogenovinyl substituents in the acid moiety. Pathways for photodecomposition of methyl [1R,cis]-2,2dimethyl-3-(2,2-dibromovinyl)cyclopanecarboxylate in methanol at 250 or 300 nm involve cis-trans isomerization, reductive debromination, and conversion of the dibromovinyl group into a bromomethoxy-epoxide derivative. Isomerization, but not debromination, involves a triplet excited state.This publication has 4 references indexed in Scilit:
- Synthesis and reactions of chloroalkene epoxidesThe Journal of Organic Chemistry, 1978
- Pyrethroid photodecomposition: PydrinJournal of Agricultural and Food Chemistry, 1978
- Pyrethroid photodecomposition: permethrinJournal of Agricultural and Food Chemistry, 1978
- Pyrethroid photochemistry: decamethrinJournal of Agricultural and Food Chemistry, 1977