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Background In recent years, protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors have been widely studied as important agricultural herbicides. Our research effort was focused on the design and synthesis of novel PPO inhibitor herbicides, done through the linking of a diphenylether pyridine bioisostere structure to substituted coumarins, which aims to enhance environmental and crop safety while retaining high efficacy. The work done in our research are the design and synthesize of a series of phenoxypyridine derivatives. Results In this work, a total of 21 compounds were synthesized via acylation reactions and all the compounds were characterized using IR, 1 H-NMR, 13 C-NMR, and high-resolution mass spectra. The respective configuration of compound IV-6 and IV-12 were also confirmed using single crystal X-ray diffraction. The bioassay results showed that the title compounds displayed notable herbicidal activity, especially compound IV-6 which displayed better herbicidal activity in greenhouse and field experiments, crop selectivity and safety for cotton and soybean as compared to that of the commercial herbicide oxyfluorfen. Conclusion The present work revealed that the compound IV-6 deserves further attention as the candidate structure of novel and safe herbicide. This article is protected by copyright. All rights reserved.