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■ NOVEL NITENPYRAM ANALOGUES WITH TETRAHYDROPYRIDONE-FIXED CIS-CONFIGURATION: SYNTHESIS, INSECTICIDAL ACTIVITIES, AND MOLECULAR DOCKING STUDIES

Chuan-Wen Sun,* Jing Wang, Ying Wu, Shi-Bin Nan, and Wang-Geng Zhang

*College of Life and Environmental Science, Shanghai Normal University , No. 100 Guilin road, Shanghai 200234, China

Abstract

To make further researches on the diversity of nitenpyram analogues with a cis-nitromethylene configuration, a series of cis-nitenpyram analogues (3a-q) with tetrahydropyridone fixed cis-configuration were designed and synthesized. Preliminary bioassays showed that most of the designed nitenpyram analogues exhibited good insecticidal activity at 100 mg/L against Nilaparvata lugens and Myzus persicae, while analogues 3n afforded the best in vitro activity. Modeling the ligand-receptor complexes by molecular docking study revealed the analogues 3 with various substituents on phenyl show their different binding affinities to the insect nAChR, which also explained the structure-activity relationships observed in vitro.