Effect on Insecticidal Activity of Substituents at the 1, 4-Benzodioxanyl Moiety of Haedoxan

Abstract

The haedoxan analog, (±)-2-(2, 6-dimethoxyphenoxy)-1-hydroxy-6-(6-methoxy-1, 4-benzodioxan-7-yl)-3, 7-dioxabicyclo[3.3.0]octane, and its congeners with 2-alkoxymethyl, 2-hydroxymethyl, 2-chloro-methyl and 3-(3, 4-methylenedioxyphenyl) substituents on the 1, 4-benzodioxanyl group were synthesized from 6-methoxy-1, 4-benzodioxan-7-carbaldehyde and its (±)-2-and 3-substituted derivatives, respectively. Some analogs were considerably insecticidal, although much less active than natural haedoxan A. The assay results suggest that 2, 3-disubstitution on the 1, 4-benzodioxanyl group was necessary to intensify the insecticidal activity.