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受天然新木脂素启发的新型农药候选物:含 2-氨基苯并恶唑融合核心骨架的厚朴酚类似物的制备及杀虫活性研究。

Novel Pesticide Candidates Inspired by Natural Neolignan: Preparation and Insecticidal Investigation of Honokiol Analogs Containing 2-Aminobenzoxazole-Fused Core Scaffold.

机构信息

Shanxi Key Laboratory of Integrated Pest Management in Agriculture, College of Plant Protection, Shanxi Agricultural University, Taigu, 030801 Shanxi Province, P. R. China.

出版信息

J Agric Food Chem. 2024 Sep 25;72(38):20805-20815. doi: 10.1021/acs.jafc.4c03080. Epub 2024 Sep 12.

DOI:10.1021/acs.jafc.4c03080
PMID:39263791
Abstract

As a continuation of our efforts to develop new agrochemicals with typical architecture and efficient bioactivity from plant natural products, natural neolignan honokiol was used as a lead compound to prepare novel analogs bearing the core 2-aminobenzoxazole scaffold. Their insecticidal potency against two representative agricultural pests, Linnaeus and (Walker), were evaluated in vivo. The pesticide bioassay results revealed that compounds , , , and exhibited prominent larvicidal activity against the larvae of (LC = 7.95, 11.85, 15.51, and 12.06 μg/mL, respectively), superior to the precursor honokiol (LC = 43.35 μg/mL) and two botanical insecticides, toosendanin (LC = 26.20 μg/mL) and rotenone (LC = 23.65 μg/mL). Compounds , , and displayed a more pronounced nonchoice antifeedant effect (AFC = 9.48, 9.14, and 12.41 μg/mL, respectively) than honokiol (AFC = 54.81 μg/mL) on . Moreover, compounds , , , , , and showed better growth inhibitory activity against (LC = 0.36, 0.34, 0.28, 0.16, 0.26, and 0.11 mg/mL, respectively) than honokiol, toosendanin, and rotenone (LC = 1.48, 0.53, and 0.46 mg/mL, respectively). A potted plant assay under greenhouse conditions illustrated that compounds and continued to provide good control efficacy against and an apparent protective effect on plants. Further cytotoxicity assay revealed that the aforementioned potent compounds showed relatively moderate toxicity and a good safety profile for non-target mammalian cells. Overall, the current work provides valuable insight into the agrochemical innovation of honokiol-derived analogs for use as natural-inspired pesticides in agricultural pest management.

摘要

作为我们从植物天然产物中开发具有典型结构和高效生物活性的新型农用化学品努力的延续,天然新木脂素和厚朴酚被用作先导化合物,制备具有核心 2-氨基苯并恶唑支架的新型类似物。它们对两种代表性农业害虫 和 的体内杀虫活性进行了评估。农药生物测定结果表明,化合物 、 、 和 对 的幼虫表现出突出的杀幼虫活性(LC = 7.95、11.85、15.51 和 12.06 μg/mL),优于前体和厚朴酚(LC = 43.35 μg/mL)和两种植物性杀虫剂,川楝素(LC = 26.20 μg/mL)和鱼藤酮(LC = 23.65 μg/mL)。化合物 、 和 对 表现出更显著的非选择性拒食作用(AFC = 9.48、9.14 和 12.41 μg/mL),优于和厚朴酚(AFC = 54.81 μg/mL)。此外,化合物 、 、 、 、 和 对 的生长抑制活性优于和厚朴酚、川楝素和鱼藤酮(LC = 0.36、0.34、0.28、0.16、0.26 和 0.11 mg/mL)。温室盆栽植物试验表明,化合物 和 对 和 仍能提供良好的防治效果,对植物有明显的保护作用。进一步的细胞毒性试验表明,上述有效化合物显示出相对适中的毒性和对非靶标哺乳动物细胞良好的安全性。总的来说,本研究为利用厚朴酚衍生类似物进行农业害虫管理的天然启发型农药的农用化学品创新提供了有价值的见解。

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