Novel protoporphyrinogen oxidase inhibitors: 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives.
A series of 3 H-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-1 H-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 (1)H 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.
Li
Hua-bin
HB
State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Zhu
You-quan
YQ
Song
Xiao-wei
XW
Hu
Fang-zhong
FZ
Liu
Bin
B
Li
Yong-hong
YH
Niu
Zi-xia
ZX
Liu
Pei
P
Wang
Zhi-hong
ZH
Song
Hai-bin
HB
Zou
Xiao-mao
XM
Yang
Hua-zheng
HZ
D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D010940:Plant Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006109:Poaceae / Q000187:drug effects / Q000201:enzymology; D050768:Protoporphyrinogen Oxidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014227:Triazines / Q000138:chemical synthesis / Q000737:chemistry*
D004791:Enzyme Inhibitors; D006540:Herbicides; D010940:Plant Proteins; D011720:Pyrazoles; D014227:Triazines; D050768:Protoporphyrinogen Oxidase