Preparation and Biological Evaluation of Novel Osthole-Derived N-Benzoylthioureas as Insecticide Candidates
Preparation and Biological Evaluation of Novel Osthole-Derived N-Benzoylthioureas as Insecticide Candidates
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DOI：
10.1021/acs.jafc.2c06558
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发表时间：
2022-12-12
影响因子：
6.1
通讯作者：
Guo，Yong
中科院分区：
文献类型：
--
作者：
Yang，Ruige;Liu，Zhiyan;Guo，Yong
为了发现新的天然产物为基础的杀虫剂候选物，本文合成了多种蛇床子素衍生的N-苯甲酰基硫脲，并评估了它们对三种害虫的杀虫活性。杀虫活性测试表明，在蛇床子素的C-3′位引入N-苯甲酰基硫脲后，大多数目标化合物的杀虫活性都比母体蛇床子素强，且杀虫谱广。化合物B24对粘虫表现出最强的生长抑制（GI）作用，当以1 mg/mL的浓度处理时，最终校正死亡率为82.1%，其分别是蛇床子素和植物杀虫剂川楝素的1.64倍和1.53倍。化合物B22、B23和B25对桃蚜的LD 50分别为0.015、0.017和0.019 μg/头，上级市售的鱼藤酮（0.024 μg/头）。衍生物B19、B20、B23和B25对小菜蛾（Plutella xylostellaLinnaeus）表现出更强的杀幼虫活性，LC 50值分别为0.22、0.26、0.15和0.30 mg/mL，超过了鱼藤酮（0.37 mg/mL）。此外，化合物B19和B23对P.在温室条件下的控制功效测定中，发现木黄酮比鱼藤酮更有效。构效关系（SAR）表明，在大多数情况下，当R基团为吸电子基团时，衍生的N-苯甲酰基硫脲比R基团为供电子基团时具有更高的活性，特别是对卤代基团。此外，B19和B23具有良好的选择性，对非靶标生物的毒性较小。本研究表明，这些衍生物可作为环境友好的天然产物农药在作物保护中进行深入研究。
To discover novel natural-product-based insecticide candidates, herein, a variety of osthole-derivedN-benzoylthioureas were synthesized and assessed for their insecticidal activities against three insect pests. An insecticidal assay showed that most of the target osthole-derivedN-benzoylthioureas displayed a more potent and broad-spectrum insecticidal effect than the parent osthole after the introduction ofN-benzoylthioureas on the C-3′ position of osthole. CompoundB24displayed the most potent growth inhibitory (GI) effect onMythimna separataWalker, with a final corrected mortality rate of 82.1% when treated with a concentration of 1 mg/mL, which was 1.64- and 1.53-fold higher in comparison to osthole and the botanical insecticide toosendanin, respectively. CompoundsB22,B23, andB25displayed a more promising aphicidal effect onMyzus persicaeSulzer, and their LD50values were 0.015, 0.017, and 0.019 μg/larvae, respectively, superior to the commercially available insecticide rotenone (0.024 μg/larvae). DerivativesB19,B20,B23, andB25displayed more potent larvicidal activity againstPlutella xylostellaLinnaeus, with LC50values of 0.22, 0.26, 0.15, and 0.30 mg/mL, respectively, exceeding that of rotenone (0.37 mg/mL). Furthermore, both compoundsB19andB23againstP. xylostellawere found to be more effective than rotenone in a control efficacy assay under greenhouse conditions. The structure–activity relationship (SAR) suggested that osthole-derivedN-benzoylthioureas are more active in most cases when the R group is an electron-withdrawing group than when it is an electron-donating group, especially for halogenated groups. Additionally, the potent compoundsB19andB23possessed good selectivity and were less toxic to non-target organisms. This study suggests that these osthole-derivedN-benzoylthioureas could be further studied in depth as eco-friendly natural product pesticides in crop protection.