Synthesis, Insecticidal Assay and Molecular Docking Study of Novel Neonicotinoids N-Oxide Analogues

Eight novel neonicotinoids N-oxide analogues were designed and synthesized. All the compounds have been identified by 1H NMR and HRMS. The N-oxide analogues exhibit high insecticidal activity against cowpea aphids （Aphis craccivora） at 250 mg,L-1. The influence of N-oxide formation on the biological...

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Published inChinese journal of chemistry Vol. 30; no. 2; pp. 357 - 361
Main Author Zhang, Wenwen Fan, Yefeng Yu, Tao Xu, Zhiping Xu, Xiaoyong Cheng, Jiagao Li, Zhong
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.02.2012
WILEY‐VCH Verlag
Wiley
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Subjects
Aphididae
Aphis craccivora
bioactivity
Chemistry
Chemistry, Multidisciplinary
computational chemical study
HRMS
N-oxide
N-氧化物
NPA atomic charges
Physical Sciences
Science & Technology
分子对接
合成
新烟碱类
杀虫活性
生物活性
类似物
COMPLEX
DOMAIN
N-oxide
CRYSTAL-STRUCTURE
ACHBP
CYTOTOXINS
computational chemical study
bioactivity
NICOTINIC ACETYLCHOLINE-RECEPTOR
BINDING-SITE
NITROMETHYLENE
NPA atomic charges
DERIVATIVES
REVEALS
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Summary:Eight novel neonicotinoids N-oxide analogues were designed and synthesized. All the compounds have been identified by 1H NMR and HRMS. The N-oxide analogues exhibit high insecticidal activity against cowpea aphids （Aphis craccivora） at 250 mg,L-1. The influence of N-oxide formation on the biological activity was elucidated by computational chemical study, and it indicated that the water bridge hydrogen bonding network was broken due to the influence of the O atom connected with the pyridine ring.
Bibliography:31-1547/O6
N-oxide, bioactivity, computational chemical study, NPA atomic charges
Eight novel neonicotinoids N-oxide analogues were designed and synthesized. All the compounds have been identified by 1H NMR and HRMS. The N-oxide analogues exhibit high insecticidal activity against cowpea aphids （Aphis craccivora） at 250 mg,L-1. The influence of N-oxide formation on the biological activity was elucidated by computational chemical study, and it indicated that the water bridge hydrogen bonding network was broken due to the influence of the O atom connected with the pyridine ring.
the Doctoral Startup Foundation of China Three Gorges University - No. KJ2009B046
National Natural Science Foundation of China - No. 20802018
the Fundamental Research Funds for the Central Universities
National High Technology Research and Development Program of China (863 Program) - No. 2011AA10A207
ark:/67375/WNG-B3R0Q3FM-J
National Key Technology R&D Program of China - No. 2011BAE06B01
Shanghai Leading Academic Discipline Project - No. B507
Shanghai Foundation of Science and Technology - No. 09391911800, 08391911600, 08ZR1406500
Special Fund for Agro-scientific Research in the Public Interest - No. 201103007
ArticleID:CJOC201100177
Doctoral Program of Higher Education - No. 200802511002
National Basic Research Program of China (973 Program) - No. 2010CB126100
istex:688EF35B888911B28D3D2218606B778B6403134F
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201100177