Synthesis and Insecticidal Activity of Lignan Analogs (1)

Abstract

Several analogs modifying the 6-methoxy-2-methoxymethyl-3-(3, 4-methylenedioxyphenyl)-1, 4-benzodioxan-7-yl group of haedoxans were synthesized and their insecticidal activity was examined. 2-(2, 6-Dimethoxyphenoxy)-1-hydroxy-6-(2-methoxy-5-methoxyethoxyphenyl)-3, 7-dioxabicyclo[3.3.0]octane, which lacked the 3-(3, 4-methylenedioxybenzyloxy) moiety of the benzodioxanyl group, was not insecticidal, but caused prolonged paralysis of the housefly. A compound replacing the 6-(2-methoxy-5-methoxyethoxyphenyl) by 6-(5-butoxy-2-methoxyphenyl) exhibited insecticidal activity comparable to one thirty-thousandth of that of haedosan A. It became evident that the 1, 4-benzodioxane framework charging the 3-(3, 4-methylenedioxy)phenyl group is important for the insecticidal activity of haedoxans.