Design, synthesis and insecticidal activities of aryloxypyridinyl ethanone oxime ethers

Based on the structure of the plug-in molecule aryloxypyridine methanone, a novel series of aryloxypyridine methanone oxime ethers containing several active units (pyridine, thiazole, diaryl ether, and oxime ether) were synthesized and characterized by ¹H NMR, ¹³C NMR and HRMS. The insecticidal activities were also investigated. The target compounds had moderate to good activity against Aphis gossypii (Glover), while compounds 5a and 6i showed excellent insecticidal activities with the lethal rate of 76.8% and 70.1% at the concentration of 50 μg/mL, respectively. However, the lethal rate of the target compounds was lower than 30% at the concentration of 100 μg/mL, showing poor insecticidal activities against Plutella xylostella. This series of compounds mainly demonstrated the active characteristics of neonicotinoids, and provided a new idea for further study of their structure-activity relationship.