Design, Synthesis, and Biological Evaluation of Novel Osthole-Based Isoxazoline Derivatives as Insecticide Candidates
Design, Synthesis, and Biological Evaluation of Novel Osthole-Based Isoxazoline Derivatives as Insecticide Candidates
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DOI：
10.1021/acs.jafc.2c01925
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发表时间：
2022-06-22
影响因子：
6.1
通讯作者：
Guo, Yong
中科院分区：
文献类型：
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作者：
Liu, Zhiyan;Han, Meiyue;Guo, Yong
摘要：天然产物是防治植物病原体和害虫的丰富且环境友好的来源。为了开发新型天然产物农药，本文采用[3 + 2]环合法合成了一系列以蛇床子素为基础的异恶唑啉衍生物，并对其杀虫活性和毒性进行了评价。所有衍生物的结构均通过光谱分析进行了表征，其中衍生物B13的结构通过X射线单晶衍射进行了确证。在所有的蛇床子素衍生物中，B2对粘虫的生长抑制效果最好，校正死亡率为96.4%。3.3，是蛇床子素和川楝素的1.80倍。衍生物B13对小菜蛾幼虫的LC_（50）为0.220 mg/mL，其活性上级优于鱼藤酮。盆栽试验表明，B13和B21对小菜蛾的防效均优于鱼藤酮。此外，毒性评价表明，这些基于蛇床子素的异恶唑啉衍生物对非靶生物显示出相对较低的毒性。鉴于这些结果，蛇床子素衍生物B2、B13和B21可作为农业上的天然杀虫剂进行深入开发。
ABSTRACT: Natural products are an abundant and environmentally friendly source for controlling plant pathogens and insect pests. Toward the development of new natural product-based pesticides, here, a series of osthole-based isoxazoline derivatives were prepared by [3 + 2] annulation and evaluated for their insecticidal activities and toxicities. The structures of all osthole-based isoxazoline derivatives were characterized by various spectral analyses, and derivative B13 was further confirmed by X-ray crystallography. Among all the osthole derivatives, B2 displayed the most promising growth inhibitory effect on Mythimna separata with a final corrected mortality rate of 96.4% ?? 3.3, which was 1.80 times higher than those of both osthole and toosendanin. Derivative B13 displayed the most promising larvicidal activity against Plutella xylostella with an LC50 value of 0.220 mg/mL, which was superior to rotenone. Furthermore, both B13 and B21 also exhibited better control efficacy against P. xylostella than rotenone in the pot experiments. Additionally, the toxicity evaluation suggested that these osthole-based isoxazoline derivatives showed relatively low toxicity toward nontarget organisms. Given these results, osthole derivatives B2, B13, and B21 could be deeply developed as natural insecticidal agents in agriculture.