SYNTHESIS AND LARVICIDAL PROPERTIES OF SOME CYCLOPROPYLCARBOXAMIDES RELATED TO CIS-PERMETHRIN

Twenty-seven carboxamide derivatives of ichloroethenyl)-2,2-dimethylcy clopropanecarboxylic acid (permethrin acid) have been synthesized and evaluated in the laboratory against mosquito larvae (Aedes aegypti). T hese cis-cyclopropylcarboxamides, with N-(substituted)phenyl, N-(subst ituted)phenylmethyl, N-(substituted)phenylethyl, N-phenylpropyl, and N -phenylbutyl groups, were synthesized from the acid chloride of permet hrin acid and various arylamines in methylene chloride. The samples we re characterized by C-13 NMR spectroscopy and mass spectrometry. Secon dary amides with electron-donating (e.g., methoxy) and electron-withdr awing (e.g., trifluoromethyl) substituents on the phenyl ring as well as nine tertiary amides were investigated. l-N-(3-phenoxyphenyl)methyl cyclopropanecarboxamide was the most active experimental compound and was 25 times less potent than (+/-)-cis-permethrin. Cyclopropylcarboxa mides of the N-(substituted)phenyl, N-(substituted)phenylethyl, and N- phenylpropyl types were essentially inactive in the larvicidal tests.