Synthesis and antifungal activity of a series of N-substituted [2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-1-yl)]propylamines

A series of N-mono- or N, N-disubstituted 2-(2,4-dichlorophenyl-3-(1,2,4-triazol-1-yl)]propylamines and N-2-(2,4-dichlorophenyl-3-(1,2,4-triazol-1-yl)propyl]amides were synthesized and tested for their fungicidal activity in vitro and in vivo against a group of plant pathogenic fungi. Some compounds exhibited a fairly good in vitro activity. The replacement of the ether group of tetraconazole with a secondary or tertiary amino group leads to compounds that maintain the antifungal activity on several phytopathogenic fungi, provided that the substituents are not too bulky or lipophilic. The allyl, propargyl, and cyclopropyl groups appear particularly suitable. Although these compounds have some structural similarities with terbinafine and naftifine, which act as squalene epoxidase inhibitors, they maintain the usual mechanism of action of the other triazoles.