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

Abstract

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.

Citogenotoxicidade Induzida De Derivados Mono E Difluorados Do Eugenol Contendo Núcleos 1,2,3-Triazólicos

“…Os 1,2,3-triazois 3d e 3e foram obtidos com rendimentos de 72,5 e 65 % respectivamente, conforme descrito na literatura (LIMA et. al.…”

“…Os compostos 3d e 3e derivados do eugenol contendo o núcleo 1,2,3-triazólico foram obtidos pela reação de cicloadição entre uma ázida orgânica e um alquino aromático terminal, utilizando metodologia descrita na literatura (LIMA, et al, 2022). O 1,2,3-triazol derivado do eugenol foi diluído em quatro concentrações (50; 100; 250; 500 μg mL -1 ) para tratamento das raízes para análises citogenéticas.…”

Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

“…Its derivatives exhibit leishmanicidal, insecticidal, anti-inflammatory, antibacterial, antioxidant properties. Notably, extensive chemical modification of eugenol has resulted in substances with antifungal activity. − …”

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

“…Moreover, the 1,2,3-triazole nucleus can act as a pharmacophoric group, that is, the portion of the substance responsible for its biological activity. Thus, 1,2,3-triazole fragments have been introduced into the skeleton of numerous molecules, resulting in the discovery of compounds with important biological activities. − For example, the connection of 1,2,3-triazole and glycerol fragments resulted in triazole derivatives with significant fungicidal activity against Colletotrichum gloeosporioides. These derivatives showed efficacy compared to the commercial fungicide tebuconazole. , …”