Synthesis, biological activities and structureĝ'activity relationships for new avermectin analogues

Jian Zhang, Xiang Nan, Hai Tao Yu, Pi Le Cheng, Yan Zhang, Ying Qian Liu, Shao Yong Zhang, Guan Fang Hu, Huanxiang Liu, An Liang Chen

研究成果: Article同行評審

43 引文 斯高帕斯(Scopus)

摘要

In an effort to discover new molecules with good insecticidal activities, more than 40 new avermectin derivatives were synthesized and evaluated for their biological activities against three species of arachnids, insects and nematodes, namely, Tetranychus Cinnabarinus, Aphis craccivora and Bursaphelenchus xylophilus. All the tested compounds showed potent inhibitory activities against three insect species. Notably, the majority of compounds exhibited high selectivity against T. cinnabarinus, some of which were much better in comparison with avermectin. Especially compounds 9j (LC50: 0.005 μM) and 16d (LC50: 0.002 μM) were 2.5-and 4.7-fold more active than avermectin (LC50: 0.013 μM), respectively, against T. cinnabarinus. Moreover, compounds 9b, 9def, 9h, 9j, 9l, 9n, 9p, 9r, 9v and 17d showed superior activities with LC50 values of 2.959e5.013 mM compared to that of 1 (LC50: 6.746 mM) against B. xylophilus. Meanwhile, the insecticidal activities of compounds 9f, 9g, 9h, and 9m against A. craccivora were 7e8 times better than that of avermectin, with LC50 values of 7.744, 5.634, 6.809, 7.939 and 52.234 mM, respectively. Furthermore, QSAR analysis showed that the molecular shape, size, connectivity degree and electronic distribution of avermectin analogues had substantial effects on insecticidal potency. These preliminary results provided useful insight in guiding further modifications of avermectin in the development of potential new insecticides.

原文English
頁(從 - 到)422-432
頁數11
期刊European Journal of Medicinal Chemistry
121
DOIs
出版狀態Published - 4 10月 2016
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