Synthesis and quantitative structure-activity relationship (QSAR) studies of novel rosin-based diamide insecticides
Synthesis and quantitative structure-activity relationship (QSAR) studies of novel rosin-based diamide insecticides
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新型松香基二酰胺杀虫剂的合成及定量构效关系（QSAR）研究
DOI：
10.1039/c4ra10125a
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发表时间：
2014-01-01
期刊：
影响因子：
3.9
通讯作者：
Wang, Zongde
中科院分区：
文献类型：
--
作者：
Li, Jian;Gao, Yanqing;Wang, Zongde
为了不断开发对哺乳动物低毒性的新型天然产物杀虫剂，合成了两个系列的松香基二酰胺，并评估了它们对小菜蛾和粘虫的杀虫活性。大多数合成的化合物表现出中等至显着的杀虫活性。其中，含噻二唑的二酰胺6a-n表现出优于其他化合物的活性，特别是化合物6f和6n对小菜蛾表现出优异的杀虫活性，LC50值分别为0.223和0.214 mg·L-1，接近或低于对照氟虫酰胺（0.222 mg·L-1）。初步构效关系分析表明，苯环上带有吸电子基团的松香基二酰胺比带有给电子基团的松香基二酰胺表现出更好的杀虫活性。通过最佳的多线性回归分析，生成的定量构效关系（QSAR）模型（R-2 = 0.9566）揭示了对小菜蛾的杀虫活性与这些化合物的分子结构之间存在很强的相关性。这些结果有望指导新型松香基杀虫剂的设计和开发。
In a continuing effort to develop novel natural product-based insecticidal agents endowed with low mammalian toxicity, two series of rosin-based diamides have been synthesized, and their insecticidal activities against Plutella xylostella and Mythimna separata were evaluated. Most of the synthesized compounds exhibited moderate to significant insecticidal activity. Among them, thiadiazole-containing diamides 6a-n displayed better activity than others, especially compounds 6f and 6n which exhibited excellent insecticidal activity against P. xylostella, with LC50 values of 0.223 and 0.214 mg L-1, respectively, which approximate to, or are lower than that of, the control flubendiamide (0.222 mg L-1). The preliminary structure-activity relationship analysis indicated that rosin-based diamides with electron-withdrawing groups on the benzene ring showed better insecticidal activity than those with electron-donating groups. Via a best multilinear regression analysis, the generated quantitative structure-activity relationship (QSAR) model (R-2 = 0.9566) revealed a strong correlation of insecticidal activity against P. xylostella with molecular structures of these compounds. These consequences can be expected to instruct the design and development of new rosin-based insecticides.