Discovery of bis-aromatic ring neonicotinoid analogues fixed as cis-configuration: Synthesis, insecticidal activities, and molecular docking studies

A novel series of bis-aromatic ring neonicotinoid analogues (1a-1l, 2a-2c), were designed and prepared by introducing a new substituted aromatic ring into nitenpyram and forming a tetrahydropyrimidine ring, with the cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed most analogues exhibited good insecticidal activities at 100 mg/L, and compound 1d and 2a were highly potent even at 10 mg/L. Modeling the ligand-receptor complexes by molecular docking study explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides. (C) 2010 Elsevier Ltd. All rights reserved.