Synthesis, Crystal Structure, Spectral Characterization and Antifungal Activity of Novel Phenolic Acid Triazole Derivatives

Abstract

At present, phenolic acid derivatives and triazole derivatives have a good antifungal effect, which has attracted widespread attention. A series of novel phenolic acid triazole derivatives were synthesized, and their structures were characterized by IR, MS, NMR, and X-ray crystal diffraction. Compound methyl 4-(2-bromoethoxy)benzoate, methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate, 4-(2-(1H-1,2,4-triazol-1-yl)ethoxy)benzoic acid and 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)-3-methoxybenzoic acid crystallize in the monoclinic system with space group P21/n, the monoclinic system with space group P21, the monoclinic system with space group P21 and the orthorhombic system with space group Pca21, respectively. At a concentration of 100 μg/mL and 200 μg/mL, the antifungal activity against seven plant pathogen fungi was determined. Compound methyl 4-(2-bromoethoxy)benzoate has the best inhibitory effect on Rhizoctonia solani AG1, and the inhibitory rate reached 88.6% at 200 μg/mL. The inhibitory rates of compound methyl 4-(2-(1H-1,2,4-triazol-1-yl) ethoxy)benzoate against Fusarium moniliforme and Sphaeropsis sapinea at a concentration of 200 μg/mL were 76.1% and 75.4%, respectively, which were better than that of carbendazim.

Synthesis of the First Representatives of new 3,3a‐Dihydro‐1H‐Imidazo[4′,5′:4,5]Imidazo[2,1‐b]thia(selena)zole Heterocyclic Systems with Fungicidal Activity

“…The interaction between 1,3-dimethylsemithioglycoluril 4 a and DEAD (1.2 equiv.) was chosen for studying as a model reaction (EtOH, reflux, 2 h, similar to the preparation of imidazo [4,5e]thiazolo [2,3-c] [1,2,4]triazines, [17,18] Scheme 1. There are two potential pathways for annulation to heterocycles with thiourea moiety using DEAD: thiazole or thiazine rings formation.…”

“…Plant infectious diseases severely decrease the yield of crops as well as their quality, leading to more than $220 billion losses annually in the global economy. [1][2][3][4][5][6] Worldwide analysis has shown that pathogenic fungi are one of the most common causes of these diseases, accounting for approximately 30 % of all cases. [6,7] The use of fungicides is an effective method for combating fungal diseases, but the widespread use of known chemical fungicides can lead to drug resistance in fungi, highlighting the need for the development of new scaffolds.…”