20863-88-1Relevant academic research and scientific papers
1,3,4(2H)-Isoquinolinetrione Herbicides: Novel Redox Mediators of Photosystem I
Mitchell, Glynn,Clarke,Eric D.,Ridley, Stuart M.,Greenhow, Daren T.,Gillen, Kevin J.,et al.
, p. 49 - 58 (1995)
A series of 1,3,4(2H)-isoquinolinetriones have found to be fast-acting post-emergence herbicides, producing symptoms of desiccation. These redox-active compounds are very potent stimulators of the light-dependent consumption of oxygen at photosystem I in
Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones
Di Mola, Antonia,Tedesco, Consiglia,Massa, Antonio
, (2019)
Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to
1,3,4(2H)-isoquinolinetriones: Evaluation of amino-substituted derivatives as redox mediator herbicides
Mitchell, Glynn,Clarke, Eric D.,Ridley, Stuart M.,Bartlett, David W.,Gillen, Kevin J.,Vohra, Shaheen K.,Greenhow, Daren T.,Ormrod, John C.,Wardman, Peter
, p. 120 - 126 (2007/10/03)
Amino-substituted derivatives of 2-ethyl-1,3,4(2H)-isoquinolinetrione have been prepared with the aim of enhancing their hydrolytic stabilities relative to other isoquinolinetriones, and hence potentially improving their herbicidal effects. 5-Amino-2-ethyl-1,3,4(2H)-isoquinolinetrione has been shown to be 12 and 8 times more stable towards hydrolysis than the isomeric 7- and 8-amino derivatives, respectively, and 120 times more stable than 2- ethyl-1,3,4(2H)-isoquinolinetrione itself. Pulse radiolysis studies have shown 5-amino-2-ethyl-1,3,4(2H)-isoquinolinetrione to have free-radical properties which could enhance the generation of superoxide radicals in plants. The compound is a potent stimulator of the light-dependent consumption of oxygen at photosystem I in isolated chloroplasts and also shows high activity in isolated leaf discs. Evidence is presented which indicates that the rate of foliar uptake is a major factor affecting herbicidal activity for this compound. (C) 2000 Society of Chemical Industry.
On the reactions of 1,3-isoquinolinediones with singlet oxygen
Ling, Ke-Qing,Ye, Jia-Hai,Chen, Xian-Yang,Ma, De-Jian,Xu, Jian-Hua
, p. 9185 - 9204 (2007/10/03)
Reactions of 1,3-isoquinolinediones 5 and 4-alkylated 1,3- isoquinolinediones 13 with singlet oxygen are entirely dominated by their enolization and proceed smoothly in benzene in the presence of pyridine as a base and a hydrogen bond acceptor. The products are triketones 6 and benzoisofuranones 7 for 5, and hydroperoxides 14, hydroxides 15 and benzoisofuranones 16 for 13. It was found that hydrolysis of 6 afforded the isoindolones 8 and not products 7, whereas alkaline cleavage of the hydroperoxide 14a yielded not only 16a, but also the isoindolone 19a, In view of these observations, an unusual [4+2] cycloaddition of the electron-rich enol 21 with singlet oxygen is proposed to be responsible for the formation of products 7 and 16, while products 6, 14 and 15 arise from both the [4+2] cycloaddition and the usual Schenck ene reaction pathways. This special diene reactivity of the isoquinolinone system towards singlet oxygen is further interpreted by frontier molecular orbital (FMO) interaction considerations.
