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Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: replacement of nitromethylene with nitroconjugated system.

Authors
  • Shao, Xusheng
  • Li, Zhong
  • Qian, Xuhong
  • Xu, Xiaoyong
Type
Published Article
Journal
Journal of Agricultural and Food Chemistry
Publisher
American Chemical Society
Publication Date
Feb 11, 2009
Volume
57
Issue
3
Pages
951–957
Identifiers
DOI: 10.1021/jf803305f
PMID: 19138119
Source
Medline
License
Unknown

Abstract

To replace nitromethylene pharmacophore with a nitroconjugated system, a series of novel neonicotinoid analogues bearing five-membered aromatic heterocycles were designed and synthesized. Bioassays indicated that some of the synthesized compounds exhibited higher insecticidal activities than imidacloprid against cowpea aphids ( Aphis craccivora ), armyworm ( Pseudaletia separate Walker), Nephotettix bipunctatus (Fabricius), and small brown rice planthopper ( Laodelphasx striatellus ). Exhilaratingly, the activity levels of derivatives 13a and 13j rivaled that of imidacloprid.

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