Quantitative structure-activity studies of pyrethroids. 31. Insecticidal activity of meta-substituted benzyl esters of 1-(para-ethoxyphenyl)2,2-dichlorocyclopropane- and -2,2,3,3-tetrafluorocyclobutane-1-carboxylic acids
1994
Nishimura, K. | Kato, S. | Holan, G. | Ueno, T. | Fujita, T.
Esters of racemic 1-(para-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane- and 1-(para-ethoxyphenyl) 2,2-dichlorocyclopropane-1-carboxylic acids with a number of meta-substituted benzyl alcohols were prepared. Their insecticidal activity against American cockroaches was measured by injection under synergistic conditions with inhibitors of oxidative and hydrolytic metabolic mechanisms. The insecticidal activity of the tetrafluorocyclobutanecarboxylates was usually more potent than that of the corresponding dichlorocyclopropanecarboxylates, although the degree was not uniform. Variations in the insecticidal potency were quantitatively examined using physicochemical substituent and structural parameters and regression analyses. The introduction of substituents possessing a benzene ring per se was favorable for the activity when factors due to physicochemical and steric features were equal among analogs in the two series of esters. The less bulky the substituents, the higher the insecticidal potency of both series, when the effect of the benzene ring was separated. For F4-cyclobutanecarboxylates, the hydrophobicity of substituents augmented the potency. In each series, the effect of substituents introduced into the phenoxy-benzene ring as the component of the primary substituent was such that there is an optimum hydrophobicity for the interaction of this local moiety with a hypothetical receptor. The para-substituted phenoxy groups were more favorable than ortho- and meta-substituted phenoxy groups.
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