二价和氧桥型新烟碱类化合物由二醛和硝基亚甲基类似物构建：设计、合成、晶体结构和杀虫活性。

Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities.

机构信息

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.

出版信息

J Agric Food Chem. 2010 Mar 10;58(5):2696-702. doi: 10.1021/jf902531y.

DOI:10.1021/jf902531y

PMID:20000569

Abstract

A series of divalent and oxabridged neonicotinoids were synthesized by reactions of nitromethylene analogues of imidacloprid and dialdehydes, and their structures were confirmed by (1)H NMR, (13)C NMR, high-resolution mass spectroscopy, and X-ray diffraction analysis. The bioassays indicated that some of them were endowed with excellent insecticidal activities against cowpea aphid ( Aphis craccivora ), armyworm ( Pseudaletia separata Walker), and brown planthopper ( Nilaparvata lugens ). Divalent neonicotinoid 6 and oxabridged 8a had higher activities than imidacloprid against cowpea aphids and armyworm; furthermore, the activity of 8a was 40.4-fold higher than that of imidacloprid against imidacloprid-resistant brown planthopper.

摘要

一系列二价和氧桥型新烟碱类化合物通过硝基亚甲基类似物与二醛的反应合成，并通过（1）H NMR、（13）C NMR、高分辨率质谱和 X 射线衍射分析确认其结构。生物测定表明，其中一些化合物对豇豆蚜（Aphis craccivora）、粘虫（Pseudaletia separata Walker）和褐飞虱（Nilaparvata lugens）具有优异的杀虫活性。二价新烟碱类化合物 6 和氧桥型 8a 对豇豆蚜和粘虫的活性均高于吡虫啉；此外，8a 的活性比吡虫啉对吡虫啉抗性褐飞虱高 40.4 倍。