Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives

A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore (CNO2) were synthesized via practical aza-ene reaction and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens) and cowpea aphids (Aphis craccivora) at 500 mg L−1. Among them, compound 11h was active against brown planthopper at 100 mg L−1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.

Graphical abstractA series of new tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives were synthesized via convenient and practical aza-ene reaction. Some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens).Figure optionsDownload full-size imageDownload as PowerPoint slide