Journal of Pesticide Science
Online ISSN : 1349-0923
Print ISSN : 1348-589X
ISSN-L : 0385-1559
Facile Synthesis of Nitrification Inhibitory Arylamino-1, 3, 5-triazines
Nucleophilic Substitution Reaction of Trichloromethyl-1, 3, 5-triazines with Arylamines
Kazuya KOIZUMIYoshiko MIYAMOTONatsuko OKANOManabu MURAKAMIKo WAKABAYASHI
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JOURNAL FREE ACCESS

1994 Volume 19 Issue 2 Pages 85-92

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Abstract
A series of 2-substituted-4-arylamino-6-trichloromethyl-1, 3, 5-triazines is one of the most interesting chemical species for nitrification-inhibitory activity. This type of compounds has conventionally been obtained by the rather laborious processes via following reactions, i. e., hydroxylation of 2-substituted-4, 6-bis(trichloromethyl)-1, 3, 5-triazines to 2-substituted-4-hydroxy-6-trichloromethyl-1, 3, 5-triazines, chlorination of the hydroxy-1, 3, 5-triazines to 2-substituted-4-chloro-6-trichloromethyl-1, 3, 5-triazines, followed by substitution reaction of the chloro-1, 3, 5-triazines with arylamines. A new method has recently been found which permits the direct nucleophilic replacement of one trichloromethyl group attached to a 1, 3, 5-triazine ring with an arylamino group. The desired replacement reaction of the trichloromethyl by an arylamino group is accomplished in the present of tertiary amines such as triethylamine. By this method, a lot of biologically active 2-substituted-4-arylamino-6-trichloromethyl-1, 3, 5-triazines can be synthesized from 2-substituted-4, 6-bis(trichloromethyl)-1, 3, 5-triazines.
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© Pesticide Science Society of Japan
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