文献类型：期刊文献

英文题名：Design, Synthesis, Crystal Structure Analysis, and Insecticidal Evaluation of Phenylazoneonicotinoids

作者：Ye, Zhenjun[1];Xia, Shuang[1];Shao, Xusheng[1];Cheng, Jiagao[1];Xu, Xiaoyong[1];Xu, Zhiping[1];Li, Zhong[1];Qian, Xuhong[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份：2011

卷号：59

期号：19

起止页码：10615

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20114114414297);WOS:【SCI-EXPANDED(收录号:WOS:000295488000028)】；

基金：This work was financially supported by the National Basic Research Program of China (973 Program, 2010CB126100), National High Technology Research, the Development Program of China (863 Program, 2011AA10A207), the National Key Technology R&D Program of China (2011BAEO6B01), and the Special Fund for Agro-scientific Research in the Public Interest (201103007). This work was also partly supported by the Shanghai Foundation of Science and Technology (09391911800, 09XD1401300), the Shanghai Leading Academic Discipline Project (Project B507), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：phenylazo compounds; neonicotinoids; pi-pi stacking; insecticide

摘要：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.