RESUMO
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.
Assuntos
Inibidores Enzimáticos/química , Herbicidas/química , Proteínas de Plantas/antagonistas & inibidores , Protoporfirinogênio Oxidase/antagonistas & inibidores , Pirazóis/química , Triazinas/química , Inibidores Enzimáticos/síntese química , Herbicidas/síntese química , Isomerismo , Espectroscopia de Ressonância Magnética , Proteínas de Plantas/metabolismo , Poaceae/efeitos dos fármacos , Poaceae/enzimologia , Protoporfirinogênio Oxidase/metabolismo , Pirazóis/síntese química , Relação Estrutura-Atividade , Triazinas/síntese químicaRESUMO
In the title mol-ecule, C(19)H(15)F(3)N(2)O, the benzene rings of the tolyl and trifluoro-methyl-phenyl groups form dihedral angles of 64.1â (2) and 38.5â (2)°, respectively, with the pyridazine ring. The CF(3) group is disordered over two orientations, with site-occupancy factors of ca 0.56 and 0.44.
