Novel Pesticide Candidates Inspired by Natural Neolignan: Preparation and Insecticidal Investigation of Honokiol Analogs Containing 2-Aminobenzoxazole-Fused Core Scaffold,Journal of Agricultural and Food Chemistry

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Novel Pesticide Candidates Inspired by Natural Neolignan: Preparation and Insecticidal Investigation of Honokiol Analogs Containing 2-Aminobenzoxazole-Fused Core Scaffold
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-12 , DOI: 10.1021/acs.jafc.4c03080
Xiao-Yan Zhi ₁ , Ying Liu ₁ , Jing Liang ₁ , Xin Yuan ₁ , Hong-Cheng Shi ₁ , Jin-Qiu Duan ₁ , Ming-Tao He ₁ , Yi Wang ₁ , Hui Cao ₁ , Chun Yang ₁

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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, Plutella xylostella Linnaeus and Mythimna separata (Walker), were evaluated in vivo. The pesticide bioassay results revealed that compounds 7″a, 9, 10d, and 10j exhibited prominent larvicidal activity against the larvae of P. xylostella (LC₅₀ = 7.95, 11.85, 15.51, and 12.06 μg/mL, respectively), superior to the precursor honokiol (LC₅₀ = 43.35 μg/mL) and two botanical insecticides, toosendanin (LC₅₀ = 26.20 μg/mL) and rotenone (LC₅₀ = 23.65 μg/mL). Compounds 7d, 10d, and 10j displayed a more pronounced nonchoice antifeedant effect (AFC₅₀ = 9.48, 9.14, and 12.41 μg/mL, respectively) than honokiol (AFC₅₀ = 54.81 μg/mL) on P. xylostella. Moreover, compounds 7b, 7″a, 9, 10d, 10f, and 10j showed better growth inhibitory activity against M. separata (LC₅₀ = 0.36, 0.34, 0.28, 0.16, 0.26, and 0.11 mg/mL, respectively) than honokiol, toosendanin, and rotenone (LC₅₀ = 1.48, 0.53, and 0.46 mg/mL, respectively). A potted plant assay under greenhouse conditions illustrated that compounds 10d and 10j continued to provide good control efficacy against P. xylostella 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.

中文翻译：

受天然新木酚素启发的新型候选农药：含有2-氨基苯并恶唑稠合核心支架的和厚朴酚类似物的制备及杀虫研究

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的继续努力，天然新木脂素和厚朴酚被用作先导化合物，制备带有核心2-氨基苯并恶唑支架的新型类似物。在体内评估了它们对两种代表性农业害虫小菜蛾和粘虫的杀虫效力。农药生物测定结果表明，化合物7'a 、 9、10d和10j对小菜蛾幼虫具有显着的杀幼虫活性（LC ₅₀分别为7.95、11.85、15.51和12.06 μg/mL），优于化合物7'a、 9、10d和10j。前体和厚朴酚 (LC ₅₀ = 43.35 μg/mL) 和两种植物杀虫剂川楝素 (LC ₅₀ = 26.20 μg/mL) 和鱼藤酮 (LC ₅₀ = 23.65 μg/mL)。化合物7d 、 10d和10j对小菜蛾表现出比和厚朴酚 (AFC ₅₀ = 54.81 μg/mL) 更显着的非选择拒食作用 (AFC ₅₀ = 9.48、9.14 和 12.41 μg/mL)。此外，化合物7b 、 7''a 、 9 、 10d 、 10f和10j对M. separata表现出比和厚朴酚更好的生长抑制活性（LC ₅₀分别为 0.36、0.34、0.28、0.16、0.26 和 0.11 mg/mL）。、川楝素和鱼藤酮（LC ₅₀分别 = 1.48、0.53 和 0.46 mg/mL）。温室条件下的盆栽植物测定表明，化合物10d和10j继续对小菜蛾提供良好的防治功效并对植物具有明显的保护作用。进一步的细胞毒性测定表明，上述有效化合物对非靶哺乳动物细胞表现出相对中等的毒性和良好的安全性。总体而言，当前的工作为和厚朴酚衍生类似物在农业害虫防治中用作天然农药的农用化学创新提供了宝贵的见解。

更新日期：2024-09-12

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