College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi China.
School of Marine Sciences, Ningbo University, Ningbo 315211, Zhejiang China.
J Agric Food Chem. 2024 Apr 3;72(13):6913-6920. doi: 10.1021/acs.jafc.3c07015. Epub 2024 Mar 22.
To explore natural product-based pesticide candidates, a series of indole derivatives containing the isoxazoline skeleton at the N-1 position were synthesized by 1,3-dipolar [2 + 3] cycloaddition reaction. Their structures were characterized by melting points (mp), infrared (IR) spectra, proton nuclear magnetic resonance spectra (H NMR), carbon-13 nuclear magnetic resonance spectra (C NMR), and high resolution mass spectrometry (HRMS). The single-crystal structures of five compounds were presented. Against Boisduval, compound showed greater than 3.8-fold acaricidal activity of indole and good control effects under glasshouse conditions. Against Van der Goot, compounds and exhibited 48.3- and 36.8-fold aphicidal activity of indole and 6-methylindole, respectively. Particularly, compound showed good bioactivities against and . Against Hausmann, compound and showed 2.1 and 1.9 times higher aphicidal activity compared to indole. Furthermore, the construction of the epidermal cuticle layer of -treated carmine spider mites was distinctly damaged, which ultimately led to their death.
为了探索基于天然产物的农药候选物，我们通过 1,3-偶极子[2+3]环加成反应合成了一系列在 N-1 位含有异恶唑啉骨架的吲哚衍生物。它们的结构通过熔点（mp）、红外（IR）光谱、质子核磁共振谱（H NMR）、碳-13 核磁共振谱（C NMR）和高分辨率质谱（HRMS）进行了表征。给出了五个化合物的单晶结构。在针对 Boisduval 的测试中，化合物表现出比吲哚高出 3.8 倍的杀螨活性，并且在温室条件下具有良好的防治效果。在针对 Van der Goot 的测试中，化合物和表现出比吲哚和 6-甲基吲哚高出 48.3 倍和 36.8 倍的杀蚜活性。特别是，化合物对和表现出良好的生物活性。在针对 Hausmann 的测试中，化合物和的杀蚜活性分别比吲哚高出 2.1 倍和 1.9 倍。此外，处理过的朱砂叶螨的表皮角质层层明显受损，最终导致它们死亡。
