Divalent and Oxabridged Neonicotinoids Constructed by Dialdehydes and Nitromethylene Analogues of Imidacloprid: Design, Synthesis, Crystal Structure, and Insecticidal Activities

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 5; pp. 2696 - 2702
• Main Authors: Shao, Xusheng, Fu, Hua, Xu, Xiaoyong, Xu, Xinglei, Liu, Zewen, Li, Zhong, Qian, Xuhong
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 10-03-2010
• Subjects: agricultural research; agrochemicals; Animals; Aphids; Biological and medical sciences; crystal structure; Crystallography, X-Ray; design; dialdehydes; Food industries; Fundamental and applied biological sciences. Psychology; Imidazoles - chemistry; insecticidal properties; Insecticides - chemical synthesis; Insecticides - chemistry; Insecticides - pharmacology; Magnetic Resonance Spectroscopy; Moths; neonicotinoid insecticides; Neonicotinoids; Nicotine - chemical synthesis; Nicotine - chemistry; Nicotine - pharmacology; Nitro Compounds - chemistry; nitromethylene analogs; product development; synthesis; Neonicotinoids; insecticide; oxabridge; dialdehydes; imidacloprid; Design; Insecticide; Synthesis; Pesticides; Dialdehyde; Crystalline structure
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf902531y

A series of divalent and oxabridged neonicotinoids were synthesized by reactions of nitromethylene analogues of imidacloprid and dialdehydes, and their structures were confirmed by 1H NMR, 13C NMR, high-resolution mass spectroscopy, and X-ray diffraction analysis. The bioassays indicated that some of them were endowed with excellent insecticidal activities against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nilaparvata lugens). Divalent neonicotinoid 6 and oxabridged 8a had higher activities than imidacloprid against cowpea aphids and armyworm; furthermore, the activity of 8a was 40.4-fold higher than that of imidacloprid against imidacloprid-resistant brown planthopper.