Aminotriazole resistance

While the high solubility of aminotriazole in water (28g per 100ml at 23°C) suggests ready leaching from whole soil, Russell et al. [106] showed if the soil contains a montmorillonite-type mineral, the aminotriazole might be resistant to leaching as a result of adsorption by the montmorillonite. 

Because a 3-benzyl group is often used for protection during synthesis or transformation of the 4-aminotriazoles, the need for debenzylation often arises. This operation can be vigorously reductive because the 1,2,3-triazole nucleus resists reduction. The most used debenzylation method is that of... 

Although the 4-aminotriazole-5-carbaldehydes resist N-acylation, they readily undergo condensations of this kind [73JCS(P1)2037]. 4-Amino-l-methyltriazole-5-carbaldehyde, heated with triethyl orthoformate, gave 4-ethoxymethylenamino-l-methyltriazole-5-carbaldehyde (29a) (120°C, 3 hr, 72%), and the 3-benzyl analog was obtained similarly (82%). With triethyl orthoacetate, the product was 4-(a-ethoxyethylidenamino)-l-methyltriazole-... 

The preparation and reactions of the azine, phenylhydrazone, and phenyl-semicarbazone of 4-amino-5-formyl-2-methyltriazole proceeded normally. One acetal has been prepared as follows. 4-Amino-3-benzyl-5-formyltriazole and boron trifluoride (as diethyl ether complex), stirred in methanol, gave 4-amino-3-benzyl-5-dimethoxymethyltriazole (20°C, 6 hr, 53%) and a dimeric by-product, 4-amino-3-benzyl-5-(3-benzyl-5-dimethoxytriazol-4-ylimino-methyl)triazole [73JCS(P1)2037]. The amino group in 4-aminotriazole-5-carbaldehydes lends itself readily to the formation of amidines and imidates (Section III,B,1), but it resists acylation. 

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