Natural products-based pesticides: Design, synthesis and pesticidal activities of novel fraxinellone derivatives containing N-phenylpyrazole moiety
Natural products-based pesticides: Design, synthesis and pesticidal activities of novel fraxinellone derivatives containing N-phenylpyrazole moiety
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基于天然产物的农药：含N-苯基吡唑部分的新型fraxinellone衍生物的设计、合成及其农药活性
DOI：
10.1016/j.indcrop.2018.02.088
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发表时间：
2018-07-01
影响因子：
5.9
通讯作者：
Guo, Yong
中科院分区：
文献类型：
--
作者：
Yang, Ruige;Xu, Ting;Guo, Yong
白蜡酮是一种降解性的柠檬苦素类化合物，主要从十字花科和十字花科的一些可再生植物中分离得到。为了不断寻找新的天然产物类农药，设计、合成了两个含N-苯基吡唑基团的秦皮酮类化合物，并评价了它们对粘虫和小菜蛾的杀虫活性。X-射线衍射仪进一步明确确定了化合物7g和8k的两个结构。生物活性测定表明，半数以上的目标化合物比先驱物秦皮酮具有更好的杀虫活性。在所有目标化合物中，化合物7G-I和8G-J的杀虫活性强于市售植物性农药川蒿素。化合物8G对小菜蛾有较好的杀灭活性，其LC_(50)值为0.31mU·moL·mL~(-1)。构效关系(SAR)研究表明，在秦皮酮的呋喃甲环上引入多卤代苯基吡唑环，可以得到比一卤代苯基吡唑环或给电子基取代苯基吡唑环更有效的化合物。
Fraxinellone, a degraded limonoid, has been mainly isolated from some renewable plants in Meliaceae and Rutaceae. In a continuous effort to discover new natural products-based pesticides, two series of fraxinellone derivatives containing N-phenylpyrazole moiety were designed, synthesized and evaluated for their pesticidal activities against Mythimna separata Walker and Plutella xylostella Linnaeus. Two structures of compounds 7g and 8k were unambiguously determined by X-ray diffraction further. The bioassay showed that over half of the target compounds exhibited better insecticidal activity against M. separata than the precursor fraxinellone. Among all the target compounds, the compounds 7g-i and 8g-j exhibited more potent insecticidal activity than toosendanin, a commercial botanical pesticide. Furthermore, the compound 8g displayed more promising larvicidal activity with the LC50 value of 0.31 mu mol mL(-1) than the toosendanin against P. xylostella. The structure activity relationship (SAR) revealed that introduction of polyhalogenated phenylpyrazole ring on furyl-ring of fraxinellone could lead more potent compounds both against M. separata and P. xylostella than that of monohalogenated phenylpyrazole ring or electron-donating groups substituted phenylpyrazole ring.