Plant Constituents Biologically Active to Insects. IV. Antifeedants for the Larvae of the Yellow Butterfly, Eurema hecabe mandarina, in Arachniodes standishii

Abstract

Nine species of plants having antifeeding activities for the larvae of the yellow butterfly, Eurema hecabe mandarina DE L'ORZA, were found. From one of them, Arachniodes standishii (MOORE) OHWI, the known compound, 1-(2, 4, 6-trimethoxyphenyl) but-trans-2-en-1-one (I), was isolated as an antifeedant. This compound was synthesized according to the Friedel-Crafts procedure, which also gave two new compounds, 1, 3-bis (2, 4, 6-trimethoxyphenyl) butan-1-one (VI) and 1-(2, 4, 6-trimethoxyphenyl)-3-[3-(2-trans-butenoyl)-2, 4, 6-trimethoxyphenyl] butan-1-one (VII), as by-products. Treatment of 1, 3, 5-trimethoxybenzene (V) with ferric chloride was found to afford 2, 2', 4, 4', 6, 6'-hexamethoxybiphenyl (VIII), which has been synthesized according to Ullmann's procedure.