Synthesis, structure and biological activities of pyrethroids with nitrogen containing five-membered heterocyclic ketone moieties

Ten new pyrethroids with nitrogen containing five-membered heterocyclic ketone moieties were synthesized by the reaction of 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (1a) or 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane-1-carboxylic acid (1b), with thionyl chloride, and then condensation reaction with 2-oxazolidinone, 2-thiazolidinethione, 2-thiazolidinone, 1-acetylimidazolidin-2-one and 1-(methylsulfonyl)imidazolidin-2-one respectively in the presence of triethylamine. Their structures were confirmed by H-1 NMR, IR, Mass Spectra and elemental analysis. The crystal structure of 3-(1-(4-ethoxyphenyl)-2,2-dichlorocyclopropylcarbonyl)oxazolidin-2-one (4a-1) was determined by X-ray diffraction analysis. The preliminary bioassay showed that some of the compounds exhibited certain fungicidal activities against Botrytis cinerea, 4a-1 and 3-(3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2-dimethylcyclopropylcarbonyl)thiazolidin-2-one (4b-3) exhibited 50% and 90% inhibition activities against Mythimnaseparate respectively.