期刊
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
卷 59, 期 19, 页码 10615-10623出版社
AMER CHEMICAL SOC
DOI: 10.1021/jf2029708
关键词
phenylazo compounds; neonicotinoids; pi-pi stacking; insecticide
资金
- National Basic Research Program of China (973 Program) [2010CB126100]
- National High Technology Research, the Development Program of China (863 Program) [2011AA10A207]
- National Key Technology R&D Program of China [2011BAEO6B01]
- Special Fund for Agro-scientific Research in the Public Interest [201103007]
- Shanghai Foundation of Science and Technology [09391911800, 09XD1401300]
- Shanghai Leading Academic Discipline Project [B507]
- Fundamental Research Funds for the Central Universities
On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the pi-pi interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral (H-1 NMR, C-13 NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids (Aphis craccivora). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.
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