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To find novel herbicidal compounds with high activity and broad spectrum, a series of phenylpyridine moiety-containing <i>α</i>-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 <b>7a</b> exhibited > 80% inhibitory activity against <i>Abutilon theophrasti</i>, <i>Amaranthus retroflexus</i>, <i>Eclipta prostrate</i>, <i>Digitaria sanguinalis</i>, and <i>Setaria viridis</i> at a dose of 37.5 g a.i./hm², which was better than fomesafen. Compound <b>7a</b> further exhibited excellent herbicidal activity against <i>Abutilon theophrasti</i> and <i>Amaranthus retroflexus</i> 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 <b>7a</b> and fomesafen when used to inhibit the <i>Nicotiana tabacum</i> protoporphyrinogen oxidase (<i>Nt</i>PPO) enzyme, were 9.4 and 110.5 nM. The docking result of compound <b>7a</b> 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 <i>Nt</i>PPO. This work demonstrated that compound <b>7a</b> could be further optimized as a PPO herbicide candidate to control various weeds.