Diamide derivatives containing a trifluoromethylpyridine skeleton: Design, synthesis, and insecticidal activity

Abstract

Diamide derivatives are biologically active molecules that have been widely applied in recent years in research on pesticides, especially insecticides. Using a simple and environmentally friendly scheme, a series of new diamide derivatives containing a trifluoromethylpyridine skeleton was designed, synthesized, and confirmed by 1H, 19F and 13C NMR, and HR-MS. Their insecticidal activities against Plutella xylostella and Helicoverpa armigera were measured and the relationship between structure and activity was investigated. Eight of the title compounds (D2, D5, D10, D21, D28, D29, D30 and D33) showed 100% activity against P. xylostella at 500 mg L–1. One compound, D33, still showed 100% activity against P. xylostella at 100 mg L–1 and had the lowest LC50 (lethal concentration 50%, 3.7 mg L–1) among the synthesized compounds. Molecular docking analysis revealed that D33 could be thoroughly embedded in the active pocket of the ryanodine receptor via hydrogen bonding in a manner similar to the commercial insecticide chlorantraniliprole.

Keywords

• diamide derivatives
• trifluoromethylpyridine
• synthesis
• insecticidal activity
• molecular docking