Seven-Membered Azabridged Neonicotinoids: Synthesis, Crystal Structure, Insecticidal Assay, and Molecular Docking Studies

• Published in: Journal of agricultural and food chemistry 2014-11, Vol.62 (46), p.11070-11079
• Main Authors: Xu, Renbo, Luo, Ming, Xia, Rui, Meng, Xiaoqing, Xu, Xiaoyong, Xu, Zhiping, Cheng, Jiagao, Shao, Xusheng, Li, Houju, Li, Zhong
• Format: Article
• Language: English
• Subjects: aniline; Animals; Aphids - drug effects; Aphis craccivora; Biological Assay; crystal structure; Crystallography, X-Ray; Hemiptera - drug effects; hydrophobic bonding; imidacloprid; insecticidal properties; Insecticides - chemical synthesis; Insecticides - chemistry; Insecticides - toxicity; Molecular Docking Simulation; molecular models; Molecular Structure; Moths - drug effects; Mythimna separata; Nilaparvata lugens
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf504014y

To study the influence of the ring sizes, 37 novel seven-membered azabridged neonicotinoid analogues were synthesized by reactions of nitromethylene analogues, succinaldehyde, and aniline hydrochlorides. Most of the title compounds presented higher insecticidal activities than that of imidacloprid (IMI), cycloxaprid (CYC), and eight-membered compounds against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nilaparvata lugens), which indicated that introducing the structure of a seven-membered azabridge could significantly improve the insecticidal activities of neonicotinoid analogues. Docking study and binding mode analysis also revealed that introducing methyl group into position 2 of phenyl ring could increase the hydrophobic interactions with receptor, which implied that position 2 might be the key site to get high insecticidal compounds.