Synthesis and Insecticidal Activity of Acyclic Nitroethene Compounds Containing a Heteroarylmethylamino Group

Abstract

Several 1 - [N- (heteroaromatic-methyl) -N-methyl] amino-1 -methylamino- 2 -nitroethenes (5a) were prepared, and their insecticidal activities against Nilaparvata lugens were examined. Among them 6-chloro-3-pyridyl (5a-8), 6-bromo-3-pyridyl (5a-9), 6-fluoro-3-pyridyl (5a-10) and 2-chloro-5-thiazolyl (5a-11) congeners showed 100% mortality against the insect at 0.5 or 0.8 ppm. Modifications of these compounds and the 2-bromo-5-thiazolyl congener by changing the methylamino group to (substituted) amino groups and/or the methyl group attaching to the heteroaromatic-methylamino group to other groups revealed that a lot of compounds were effective against the insect at 0.5 or 0.8 ppm. Compounds that showed 100% mortality at 0.5 or 0.8 ppm, and 5b-1 whose activity at lower concentrations was not determined were chosen for further evaluations. As a result, l-[N-(6-chloro-3-pyridylmethyl)-N-ethyl]amino-l-methylamino-2-nitroethene (5b-8, TI-304, nitenpyram) was selected as a candidate. © 1993, Pesticide Science Society of Japan. All rights reserved.