Protoporphyrinogen-IX oxidase inhibition by N-(2, 4, 5-trisubstituted phenyl)-3, 4, 5, 6-tetrahydrophthalimides
1997
Ishida, S. (Tamagawa Univ., Machida, Tokyo (Japan)) | Hirai, K. | Kohno, H. | Sato, Y. | Kubo, H. | Boeger, P. | Wakabayashi, K.
A quantitative correlation between protoporphyrinogen-IX oxidase (Protox) inhibition and peroxidizing activity of N-(2,4,5-trisubstituted phenyul)-3,4,5,6-tetrahydrophthalimides was examined. Analogues with five types of N-aryl moieties were synthesized. Type I: N-phenyl-3,4,5,6-tetrahydrophthalimide and N-(2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide; Type II: N-(4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide and N-(4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide; Type III: N-(4-chloro-3-propargyloxyphenyl)-3,4,5,6-tetrahydrophthalimide and N-)4-chloro-2-fluoro-5-propargyloxyphenyl)-3,4,5,6-tetrahydrophthalimide; and Type IV: isopropyl 2-chloro-5-(3,4,5,6-tetrahydrophthalimide)benzoate and isopropyl 2-chloro-4-fluoro-5-(3,4,5,6-tetrahydrophthalimido)benzoate; as well as Type V: N-(3,4-dihydro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-yl)-3,4,5,6-tetrahydrophthalimide and N-(3,4-dihydro-7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-yl)-3,4,5,6-tetrahydrophthalimide. Inhibition of Protox isolated from etioplasts of corn (Zea mays cv. Anjou) and Echinochloa utilis, and light-induced ethane formation by Scenedesmus acutus were assayed. The 2-fluorine substituted compound to Type II showed a stronger activity both by Protox inhibition and by ethane formation than the 2 non-substituted compound. Our findings indicate that a 2-fluoro substitution of the phenyl ring enhances the phytotoxic activity to the intact cells but not necessarily Protox inhibition
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