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

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• 作者：Renbo Xu ; Ming Luo ; Rui Xia ; Xiaoqing Meng ; Xiaoyong Xu ; Zhiping Xu ; Jiagao Cheng ; Xusheng Shao ; Houju Li ; Zhong Li
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2014
• 出版时间：November 19, 2014
• 年：2014
• 卷：62
• 期：46
• 页码：11070-11079
• 全文大小：392K
• ISSN：1520-5118

文摘

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.

Keywords:

cycloxaprid; seven-membered azabridge; neonicotinoids; insecticide