School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Avenue, Zhengzhou, Henan 450001, People's Republic of China.
J Agric Food Chem. 2022 Dec 21;70(50):15737-15746. doi: 10.1021/acs.jafc.2c06558. Epub 2022 Dec 12.
To discover novel natural-product-based insecticide candidates, herein, a variety of osthole-derived -benzoylthioureas were synthesized and assessed for their insecticidal activities against three insect pests. An insecticidal assay showed that most of the target osthole-derived -benzoylthioureas displayed a more potent and broad-spectrum insecticidal effect than the parent osthole after the introduction of -benzoylthioureas on the C-3' position of osthole. Compound displayed the most potent growth inhibitory (GI) effect on Walker, 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. Compounds , , and displayed a more promising aphicidal effect on Sulzer, and their LD values were 0.015, 0.017, and 0.019 μg/larvae, respectively, superior to the commercially available insecticide rotenone (0.024 μg/larvae). Derivatives , , , and displayed more potent larvicidal activity against Linnaeus, with LC values of 0.22, 0.26, 0.15, and 0.30 mg/mL, respectively, exceeding that of rotenone (0.37 mg/mL). Furthermore, both compounds and against were found to be more effective than rotenone in a control efficacy assay under greenhouse conditions. The structure-activity relationship (SAR) suggested that osthole-derived -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 compounds and possessed good selectivity and were less toxic to non-target organisms. This study suggests that these osthole-derived -benzoylthioureas could be further studied in depth as eco-friendly natural product pesticides in crop protection.
为了发现新型天然产物杀虫剂候选物，本文合成了多种奥士妥因衍生的 -苯甲酰基硫脲，并评估了它们对三种害虫的杀虫活性。杀虫测定表明，大多数引入奥士妥因 C-3'位的 -苯甲酰基硫脲的目标奥士妥因衍生 -苯甲酰基硫脲比母体奥士妥因具有更强和更广泛的杀虫作用。化合物 在处理浓度为 1mg/mL 时，对 Walker 的生长抑制（GI）作用最强，最终校正死亡率为 82.1%，分别比奥士妥因和植物性杀虫剂川楝素高 1.64 倍和 1.53 倍。化合物 、 、 和 对 Sulzer 具有更有希望的杀蚜作用，其 LD 值分别为 0.015、0.017 和 0.019μg/幼虫，优于市售杀虫剂鱼藤酮（0.024μg/幼虫）。衍生物 、 、 、 对 Linnaeus 具有更强的杀幼虫活性，LC 值分别为 0.22、0.26、0.15 和 0.30mg/mL，均超过鱼藤酮（0.37mg/mL）。此外，在温室条件下的防治效果测定中，化合物 和 对 的防治效果均优于鱼藤酮。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，奥士妥因衍生的 -苯甲酰基硫脲比为供电子基团时更具活性，特别是对于卤代基团。此外，具有较强活性的化合物 和 具有良好的选择性，对非靶标生物的毒性较低。本研究表明，这些奥士妥因衍生的 -苯甲酰基硫脲可以作为环保型天然产物杀虫剂在作物保护中进一步深入研究。
