Design, Synthesis, Crystal Structures, and Insecticidal Activities of Eight-Membered Azabridge Neonicotinoid Analogues
Design, Synthesis, Crystal Structures, and Insecticidal Activities of Eight-Membered Azabridge Neonicotinoid Analogues
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八元 Azabridge 新烟碱类似物的设计、合成、晶体结构和杀虫活性
DOI：
10.1021/jf4046683
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发表时间：
2014-01-15
影响因子：
6.1
通讯作者：
Li, Zhong
中科院分区：
文献类型：
--
作者：
Xu, Renbo;Xia, Rui;Li, Zhong
以原料A、戊二醛和伯胺盐酸盐(脂肪胺、苯肼和苯胺)为原料，设计合成了三个新型的氮桥新烟碱类似物。所合成的8元氮杂桥化合物对豌豆蚜虫和褐飞虱的杀虫活性均高于草桥化合物B。与吡虫啉相比，部分氮杂桥联化合物对褐飞虱表现出良好的杀虫活性。晶体结构和生物活性测定表明，桥原子由O变为N可以导致完全不同的构象，这可能是影响其生物活性的重要因素。
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.