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

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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.
Funding Information
  • the “13th Five-Year” National Key Research Program of China (2017YFD0301604, 32160660, 21562022, 20181BAB203015, GJJ200404, GJJ160382, 2022JS34)
  • The National Natural Science Foundation of China (2017YFD0301604, 32160660, 21562022, 20181BAB203015, GJJ200404, GJJ160382, 2022JS34)
  • the Natural Science Foundation of Jiangxi Province (2017YFD0301604, 32160660, 21562022, 20181BAB203015, GJJ200404, GJJ160382, 2022JS34)
  • The Key Research Foundation of Educational Department of Jiangxi Province of China (2017YFD0301604, 32160660, 21562022, 20181BAB203015, GJJ200404, GJJ160382, 2022JS34)
  • the Research Foundation of Jiangxi Medical Products Administration (2017YFD0301604, 32160660, 21562022, 20181BAB203015, GJJ200404, GJJ160382, 2022JS34)

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