Synthesis, crystal structure, and insecticidal activity of (Z)-nitenpyram derivatives with optical activity

Article abstract of DOI:10.1002/jhet.1660

Fourteen novel nitenpyram derivatives (Z)-4-substituted-3-acetyl-6- methylamino -6-[N-(6-chloro-3-pyridinylmethyl)-N-ethyl]amino-5-nitno-2-oxa-5- hexene 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n were synthesized, and their structures were confirmed by ¹H NMR, IR, and elemental analysis. The stereostructure of 4h was determined by the single-crystal X-ray analysis. The preliminary bioassay tests showed that most of the title compounds exhibited good insecticide activities against Nilaparvata lugens as well as Aphis medicaginis at 500 mg/L, whereas compound 4h afforded the best activity, with 100% mortality against A. medicaginis at 100 mg/L.