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.

中文翻译：

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新型吡唑芳族酮类似物作为HPPD抑制剂的合成及其除草活性。

背景技术4-羟基苯基丙酮酸双加氧酶（HPPD，EC 1.13.11.27）已经成为除草剂发现的良好靶标。为了发现新型的HPPD除草剂，设计并合成了一系列吡唑芳族酮类似物。结果测试了所合成的25种吡唑芳族酮类似物的除草活性，化合物A1，A3，A4，A17，A20和A25在37.5 g ha-1下显示出对浆液藜，满天星和芥菜的优异除草活性。此外，化合物A1，A5，A9，A10，A16，A17，A20和A25在150 g ha-1下对小麦，玉米和大米表现出良好的作物选择性。对AtHPPD的抑制活性证明该化合物是HPPD抑制剂。使用分子对接研究了这些吡唑芳族酮类似物的结构-活性关系。结论这些吡唑芳族酮衍生物可作为潜在的先导结构用于开发HPPD除草剂，以对双子叶杂草进行进一步的结构修饰。©2019化学工业协会。