Novel Protoporphyrinogen Oxidase Inhibitors: 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives

作者：Li, Hua-bin; Zhu, You-quan; Song, Xiao-wei; Hu, Fang-zhong; Liu, Bin; Li, Yong-hong; Niu, Zi-xia; Liu, Pei; Wang, Zhi-hong; Song, Hai-bin; Zou, Xiao-mao^*; Yang, Hua-zheng

来源：Journal of Agricultural and Food Chemistry, 2008, 56(20): 9535-9542.

DOI：10.1021/jf801774k

• 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one
• PPO inhibitor
• SAR
• herbicidal activity

A series of 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives were synthesized as candidate herbicides by diazotization of different 5(3)-amino-N-phenyl-1H-pyrazole-4-carboxamide derivatives prepared by the reaction of substituted 5(3)-amino-pyrazole-4-carbonyl chloride with a substituted aniline. Their structures were identified by H-1 NMR and elemental analyses. The isomers D and E were isolated, and their structures were identified by two-dimensional NMR analyses (heteronuclear single quantum coherence and heteronuclear multiple-bond correlation) and single-crystal X-ray diffraction analysis. The bioassay results showed that some of the title compounds exhibited both excellent herbicidal activity at a dose of 93.75 g/ha and strong inhibition against protoporphyrinogen oxidase activity in vitro. The structure-activity relationship showed that D16 possessed the highest activities both in vivo and in vitro when the N-substituted group of the pyrazole ring was allyl and the N-substituted group of benzooxazinone was propargyl.

• 单位
  南开大学; 元素有机化学国家重点实验室