Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor
2020
Fu, Qing | Cai, Peng‐Peng | Cheng, Long | Zhong, Liang‐Kun | Tan, Cheng‐Xia | Shen, Zhong‐Hua | Han, Liang | Xu, Tian‐Ming | Liu, Xing‐Hai
BACKGROUND: 4‐Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been a good target for herbicide discovery. In order to discover novel HPPD herbicides, a series of pyrazole aromatic ketone analogs were designed and synthesized. RESULTS: The 25 pyrazole aromatic ketone analogs synthesized were tested for herbicidal activity and compounds A1, A3, A4, A17, A20 and A25 displayed excellent herbicidal activity against Chenopodium serotinum, Stellaria media and Brassica juncea at 37.5 g ha⁻¹. In addition, compounds A1, A5, A9, A10, A16, A17, A20 and A25 exhibited good crop selectivity for wheat, maize and rice at 150 g ha⁻¹. Inhibition activities against AtHPPD proved the compounds were HPPD inhibitors. The structure–activity relationship of these pyrazole aromatic ketone analogs was studied using molecular docking. CONCLUSION: These pyrazole aromatic ketone derivatives could be used as lead structures for development of HPPD herbicides against dicotyledonous weeds with further structure modification. © 2019 Society of Chemical Industry
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