Synthesis of 1, 2, 4-triazolo(1, 5-a)-1, 3, 5-triazine derivatives for phytotoxic activity

Miyamoto, Y. . Coll. of Veterinary and Animal Sciences; Kohno, H.; Pfleiderer, W.; Boeger, P.; Wakabayashi, K.

Synthesis of 1, 2, 4-triazolo(1, 5-a)-1, 3, 5-triazine derivatives for phytotoxic activity

1995

Miyamoto, Y. (Kitasato Univ., Towada, Aomori (Japan). Coll. of Veterinary and Animal Sciences) | Kohno, H. | Pfleiderer, W. | Boeger, P. | Wakabayashi, K.

Reaction of benzylideneaminoguanidines with ethyl N-cyanoformimidate in acetonitrile at room temperature gave 1-benzylideneamino-2-cyanoiminomethyl guanidines. 1-Halogenobenzylideneamino-3-methylguanidines reacted with thylk N-cyanoformimidate directly to give 7-methylamino-2-halogenophenyl-1,2,4-triazolo[1,5-a]-1,3,5-t riazines under similar conditions. The 1-benzylideneamino-2-cyanoiminomethyl guanidines were readily cyclized to the corresponding 1,2-dihydro-1,2,4-triazolo[1,5-a]/1,3,5-triazines by brief heating in methanol. The dihydrotriazolotriazines were oxidized with iodine in ethanol to give the corresponding 1,2,4-triazolo[1,5-a]-1,3,5-triazines. Phytotoxic activities of the newly synthesized compounds were assayed using green microalgae, Scenedesmus acutus. 7-Amino-2-(4-chloro-2-fluorophenyl)-1,2,4-triazolo[1,5-a]-1, 3,5-triazine and some other compounds were found to suppress the cell growth and chlorophyll formation of Scenedesmus, but those activities were still not good enough to be utilized as a herbicide or plant growth regulator

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