NEW TYPES OF INSECT CHEMOSTERILANTS - BENZYLPHENOLS AND BENZYL-1,3-BENZODIOXOLE DERIVATIVES AS ADDITIVES TO HOUSEFLY DIET

Benzyl and cinnamyl derivatives of 2, 4-di-tert-butylphenol and of 1, 3-benzodioxoles sterilize mixed sexes of houseflies when fed at concentrations as low as 0.025% in the diet. Several of the compounds are also active against males, the most effective male sterilants being 2, 4-bis(l, l-dimethylethyl)-6-[(4-methoxyphenyl)methyl]phenol (lc), 5-propoxy-6-[(4-methoxyphenyl)methyl]-l, 3-benzodioxole (9d), and 5-ethoxy-6-[l-(4-methoxyphenyl)ethyl]-l, 3-benzodioxole (10c) at concentrations of 0.25, 0.1, and 0.05%,respectively. Benzyl-2, 6-di-tert-butylphenols are generally inactive. Structure-activity correlations suggest that sterilant activity is due to in vivo oxidation of the compounds to reactive quinone methides. lc(and other benzylphenols) is only slightlytoxic to mice and is nonmutagenic in standard Ames bacterial tests. © 1979, American Chemical Society. All rights reserved.