Synthesis of Eugenol-Fluorinated Triazole Derivatives and Evaluation of Their Fungicidal Activity

Autor: Lima, Ângela M. A., Paula, Wenderson T. de, Leite, Iris C. H. L., Gazolla, Poliana A. R., Abreu, Lucas M. de, Fonseca, Victor R., Romão, Wanderson, Lacerda Jr., Valdemar, Queiroz, Vagner T. de, Teixeira, Róbson R., Costa, Adilson V.
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Journal of the Brazilian Chemical Society v.33 n.10 2022
Journal of the Brazilian Chemical Society
Sociedade Brasileira de Química (SBQ)
instacron:SBQ
Journal of the Brazilian Chemical Society, Volume: 33, Issue: 10, Pages: 1200-1210, Published: 26 SEP 2022
Popis: Eugenol (C10H12O2, 4-allyl-2-methoxyphenol) is a phenolic natural product that has several biological activities and possibilities of applications. It is herein described the synthesis of eugenol-fluorinated triazole derivatives and evaluation of their fungicidal activity. The reaction of eugenol with epichlorohydrin resulted in the preparation of (±)-2-((4-allyl-2-methoxyphenoxy)methyl)oxirane (1) in 88% yield. The azidolysis of 1 with sodium azide gave the azido-alcohol (±)-1-(4-allyl-2-methoxyphenoxy)-3-azidopropan-2-ol (2) in 94% yield. The CuAAc reaction between compound 2 and different terminal alkynes afforded a series of eleven derivatives (3a 3k) within 48-80% yield. All the synthesized compounds were characterized by infrared (IR) and nuclear magnetic resonance (1H and 13C) spectroscopies and high-resolution mass spectrometry. The in vitro inhibitory activity of the compounds on the mycelial growth of a strain of Colletotrichum sp., that causes anthracnose disease on papaya fruits, was evaluated. The best result was observed for compound 1-(4-allyl-2-methoxyphenoxy)-3-(4-(2-fluorophenyl)-1H-1,2,3-triazol-1-yl)propan-2-ol (3d) that showed a mean growth-inhibition zone of 5.10 mm in a well-diffusion assay, and may serve as a template for additional structural modifications, aiming for more potent fungicidal activity.
Databáze: OpenAIRE
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