Triazines containing an azido group

Bis(alkylamino)-i-triazines containing and azido group have been developed by the Shell Co., and azido-alkylamino-alkylmercapto-.r-triazines by the Ciba-Geigy AG (Gentner, 1967 Barnsley and Gabbot, 1966 Smith and Marks, 1968), 

2-Azido-4-ethylamino-6-t-butylamino-s-triazine (WL 9385,35) is efficient for the selective control of dicotyledonous weeds in grain, maize and potato. 2-Azido-4-isopropylamino-6-methylthio-i-triazine (aziprotryne, 36) is a selective herbicide efficient in the control of certain dicotyledonous weeds in cabbage, bean, sunflower, onion and maize, as is 2-azido-4-jec-butylamino 6-methylthio-j-triazine (C 8250, 37) in soybean and cotton. 

Azido-s-triazines break down quickly in the soil. 

Relationships between the chemical structure and the effect of herbicides of the. s-triazine type have been studied by several workers in addition to Gysin and Knusli, whose work has already been cited (1960). McWhorter and Holstun 

2-methylthio-4,6-bis(alkylamino)-.s-triazines, that the 2-chloro derivatives have the highest selectivity, that the alkylmercapto derivatives are less selective, and that the alkoxy derivatives have the lowest selectivity. In the last group selective compounds occur but rarely, and this selectivity holds only within narrow dose limits. 

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