Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology , Shanghai 200237, China.
J Agric Food Chem. 2014 Jan 15;62(2):381-90. doi: 10.1021/jf4046683. Epub 2014 Jan 7.
Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.
设计并合成了三系列新型氮杂桥型烟碱类似物，它们由起始原料 A、戊二醛和伯胺盐酸盐（脂肪族伯胺、苯肼和苯胺）构建而成。大多数八元氮杂桥化合物对豇豆蚜（Aphis craccivora）和褐飞虱（Nilaparvata lugens）的杀虫活性均高于氧杂桥化合物 B。与噻虫啉相比，一些氮杂桥化合物对褐飞虱表现出优异的杀虫活性。晶体结构和生物测定表明，将桥原子从 O 改变为 N 可以导致完全不同的构象，这可能是生物活性的重要影响因素。
