To find novel herbicidal compounds with high activity and broad spectrum, a series of phenylpyridine moiety-containing α-trifluoroanisole derivatives were designed, synthesized, and identified via nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). Greenhouse-based herbicidal activity assays revealed that compound 7a exhibited > 80% inhibitory activity against Abutilon theophrasti, Amaranthus retroflexus, Eclipta prostrate, Digitaria sanguinalis, and Setaria viridis at a dose of 37.5 g a.i./hm², which was better than fomesafen. Compound 7a further exhibited excellent herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus in this greenhouse setting, with respective median effective dose (ED₅₀) values of 13.32 and 5.48 g a.i./hm², both of which were slightly superior to fomesafen (ED₅₀ = 36.39, 10.09 g a.i./hm²). The respective half-maximal inhibitory concentration (IC₅₀) for compound 7a and fomesafen when used to inhibit the Nicotiana tabacum protoporphyrinogen oxidase (NtPPO) enzyme, were 9.4 and 110.5 nM. The docking result of compound 7a indicated that the introduction of 3-chloro-5-trifluoromethylpyridine and the trifluoromethoxy group was beneficial to the formation of stable interactions between these compounds and NtPPO. This work demonstrated that compound 7a could be further optimized as a PPO herbicide candidate to control various weeds.

中文翻译：

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新型含苯基吡啶类除草剂α-三氟苯甲醚衍生物的合成

为了寻找具有高活性和广谱性的新型除草化合物，设计、合成了一系列含苯基吡啶基团的α-三氟苯甲醚衍生物，并通过核磁共振（NMR）和高分辨率质谱（HRMS）对其进行了鉴定。基于温室的除草活性测定显示化合物7a在 37.5 g ai/hm ²的剂量下对想、反枝苋、旱莲草、马唐和狗尾草表现出 > 80% 的抑制活性，优于氟磺草胺。化合物7a在这种温室环境中进一步表现出对苁蓉和反枝苋的优异除草活性，各自的中位有效剂量 (ED ₅₀ ) 值为 13.32 和 5.48 g ai/hm ²，均略优于氟磺草胺 (ED ₅₀ = 36.39, 10.09 克活性成分/hm ² )。当用于抑制烟草原卟啉原氧化酶 ( Nt PPO) 时，化合物7a和氟磺胺草醚的各自半数最大抑制浓度 (IC _{50 ) 分别为 9.4 和 110.5 nM。}化合物7a的对接结果表明3-氯-5-三氟甲基吡啶和三氟甲氧基的引入有利于这些化合物与Nt PPO之间形成稳定的相互作用。这项工作表明化合物7a可以进一步优化为 PPO 除草剂候选物以控制各种杂草。