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Novel Protoporphyrinogen Oxidase Inhibitors: 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives
- Source :
- Journal of Agricultural and Food Chemistry. 56:9535-9542
- Publication Year :
- 2008
- Publisher :
- American Chemical Society (ACS), 2008.
-
Abstract
- 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.
- Subjects :
- Magnetic Resonance Spectroscopy
Herbicides
Triazines
Stereochemistry
General Chemistry
Protoporphyrinogen oxidase activity
Pyrazole
Poaceae
Structure-Activity Relationship
chemistry.chemical_compound
Aniline
Isomerism
chemistry
Heteronuclear molecule
Propargyl
Proton NMR
Pyrazoles
Protoporphyrinogen Oxidase
Protoporphyrinogen oxidase
Enzyme Inhibitors
General Agricultural and Biological Sciences
Heteronuclear single quantum coherence spectroscopy
Plant Proteins
Subjects
Details
- ISSN :
- 15205118 and 00218561
- Volume :
- 56
- Database :
- OpenAIRE
- Journal :
- Journal of Agricultural and Food Chemistry
- Accession number :
- edsair.doi.dedup.....6c2e49762c32fcce41fc8f45e81f8275