新型吡唑芳酮类似物的合成及作为 HPPD 抑制剂的除草活性。
Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor.
机构信息
Institute of Pesticide, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, China.
Synthesis Centre, Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou, China.
出版信息
Pest Manag Sci. 2020 Mar;76(3):868-879. doi: 10.1002/ps.5591. Epub 2019 Sep 10.
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 . 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 . 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.
背景
4-羟苯基丙酮酸双加氧酶（HPPD，EC 1.13.11.27）是一种优秀的除草剂发现目标。为了发现新型 HPPD 除草剂，设计并合成了一系列吡唑芳酮类似物。
结果
测试了 25 种合成的吡唑芳酮类似物的除草活性，化合物 A1、A3、A4、A17、A20 和 A25 在 37.5 g/ha 时对藜、繁缕和芥菜表现出优异的除草活性。此外，化合物 A1、A5、A9、A10、A16、A17、A20 和 A25 在 150 g/ha 时对小麦、玉米和水稻表现出良好的作物选择性。对 AtHPPD 的抑制活性证明这些化合物是 HPPD 抑制剂。采用分子对接研究了这些吡唑芳酮类似物的构效关系。
结论
这些吡唑芳酮衍生物可作为进一步结构修饰的开发防治阔叶杂草的 HPPD 除草剂的先导结构。© 2019 化学工业协会。
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