Green Synthesis and Antifungal Activities of Novel N -Aryl Carbamate Derivatives

• Published in: Molecules (Basel, Switzerland) Switzerland), 2024-08, Vol.29 (15), p.3479
• Main Authors: Liu, Xiyao, Sun, Yuyao, Liu, Lifang, Duan, Xufei, You, Shujun, Yu, Baojia, Pan, Xiaohong, Guan, Xiong, Lin, Ran, Song, Liyan
• Format: Article
• Language: English
• Subjects: antifungal activity; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; carbamate derivatives; Carbamates; Carbamates - chemical synthesis; Carbamates - chemistry; Carbamates - pharmacology; Chloride; Crop diseases; Fungi; Fungi - drug effects; Fungicides; Fungicides, Industrial - chemical synthesis; Fungicides, Industrial - chemistry; Fungicides, Industrial - pharmacology; Fusarium - drug effects; Green Chemistry Technology; green synthesis; Lead compounds; Microbial Sensitivity Tests; Molecular Structure; Pesticides; phytopathogenic fungi; Plant diseases; Structure-Activity Relationship
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules29153479

Carbamate is a key structural motif in the development of fungicidal compounds, which is still promising and robust in the discovery of green pesticides. Herein, we report the synthesis and evaluation of the fungicidal activity of 35 carbamate derivatives, among which 19 compounds were synthesized in our previous report. These derivatives were synthesized from aromatic amides in a single step, which was a green oxidation process for Hofmann rearrangement using oxone, KCl and NaOH. Their chemical structures were characterized by H NMR, C NMR and high-resolution mass spectrometry. Their antifungal activity was tested against seven plant fungal pathogens. Many of the compounds exhibited good antifungal activity in vitro (inhibitory rate > 60% at 50 μg/mL). Compound exhibited excellent broad-spectrum antifungal activities with inhibition rates close to or higher than 70% at 50 μg/mL. Notably, compound demonstrated the most potent inhibition against , with an EC value of 12.50 μg/mL, while compound was the most promising candidate fungicide against (EC = 16.65 μg/mL). The structure-activity relationships are also discussed in this paper. These results suggest that the -aryl carbamate derivatives secured by our green protocol warrant further investigation as potential lead compounds for novel antifungal agents.