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

Abstract

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 100mg/L, and compound 1d and 2a were highly potent even at 10mg/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.