Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1,3,5-Substitued Triazole

Sixteen bridging ligand compounds of azo with 1,3,5-substitued triazole had been synthesized from 1,3,5-trisubstituted-l,2,4-triazoles by the oxidative coupling reaction using potassium permanganate or sodium dichloroisocyamirate as the oxidant. The structures of the target compounds were determined by H-1 NMR, C-13 NMR, IR, MS, HRMS and X-ray diffraction. They were tested for in vitro fungicidal activities by the mycelium growth rate method. The results indicated that most of the title compounds had a certain inhibitory activity at the concentration of 50 mu g/mL. Especially, the inhibition rate of 1,2-bis(1-butyl-3-(2-chlorophenyl)-1H-1,2,4-triazol-5-yl)diazene (3h) and 1,2-bis(3-(4-chlorophenyl)-1-propy1-1H-l,2,4-triazol-5-yl)diazene (3k) were close to that of triadimefon when against Pythium aphanidermatum, while the inhibition rate of l,2-bis(3-(2-chlorophenyl)-1-propyl-lH-l,2,4-triazol-5-yl)diazene (3g) was higher than that of riadimefon. The reactions of these compounds were simple and mild, which was of reference significance to the creation and synthesis of new pesticides.