Synthesis and Phytotoxic Activities of N-Substituted Phenyl Isothiazolone Derivatives

• Published in: Journal of Pesticide Science Vol. 28; no. 3; pp. 293 - 300
• Main Authors: MIYAMOTO, Yoshiko, IKEDA, Yumi, WAKABAYASHI, Ko
• Format: Journal Article
• Language: English; Japanese
• Published: Tokyo Pesticide Science Society of Japan 01.01.2003; Japan Science and Technology Agency
• Subjects: 3(2H)-oxo-N-(substituted phenyl)-4,5,6,7-tetrahydro-1,2-benzisothiazoles; 3-oxo-4,5,6,7-tetrahydro-1,2-benzisothiazole-1,1-dioxides; 3-oxo-4,5,6,7-tetrahydro-1,2-benzisothiazole-1-oxides; Biological and medical sciences; Fundamental and applied biological sciences. Psychology; peroxidizing activity; Phytopathology. Animal pests. Plant and forest protection; protoporphyrinogen-IX oxidase; Scenedesmus acutus; Zea mays; 3-oxo-4,5,6,7-tetrahydro-1,2-benzisothiazole-1,1-dioxides; peroxidizing activity; Enzyme; 3-oxo-4,5,6,7-tetrahydro-1,2-benzisothiazole-1-oxides; Oxidase; Pesticides; protoporphyrinogen-IX oxidase; Oxidoreductases; 3(2H)-oxo-N-(substituted phenyl)-4,5,6,7-tetrathydro-1,2-benzisothiazoles
• ISSN: 1348-589X; 0385-1559; 1349-0923
• DOI: 10.1584/jpestics.28.293

A series of 3(2H)-oxo-N-(substituted phenyl)-4,5,6,7-tetrahydro-1,2-benzisothiazoles (2) were obtained via four reaction steps starting from 2-chlorocyclohexene-1-carboxylic acid. The sulfur atom of 3-oxo-4,5,6,7-tetrahydro-1,2-benzisothiazoles (2) was oxidized with an equimolecular amount of 3-chloroperbenzoic acid (3-CPBA) in chloroform to give the corresponding 3-oxo-4,5,6,7-tetrahydro-1,2-benzisothiazole-1-oxides (3). Oxidation of 2 with two moles of 3-CPBA afforded 3-oxo-4,5,6,7-tetrahydro-1,2-benzisothiazole-1,1-dioxides (4). Phytotoxic activities of the compounds (2-4) synthesized were assayed by inhibition of protoporphyrinogen-IX oxidase isolated from corn as well as by growth inhibition, chlorophyll decrease and peroxidative destruction of cell membranes of the green microalga Scenedesmus acutus. Among the compounds (2-4), 4 showed the strongest activities according to all phytotoxic parameters, exhibiting phytotoxicities characteristic of peroxidizing herbicides. 3(2H)-oxo-2-[4-chloro-3-(isopropoxycarbonyl)phenyl]-4,5,6,7-tetrahydro-1,2-benzisothiazole-1,1-dioxide (4h) was the strongest of the compounds 4 tested.