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

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 (...

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Bibliographic Details
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
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Summary: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.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf504014y