Síntese e caracterização de novos híbridos derivados do timol e 1,2,3-triazóis com potencial aplicação no controle da antracnose do mamoeiro
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Data
2024-02-20
Autores
Oliveira, Mariana Belizario de
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Universidade Federal do Espírito Santo
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The agricultural environment is frequently affected by phytopathogens which threaten global food security and the economic sector. In Espírito Santo, the papaya crop, responsible for a large part of the state's income, is severely damaged by anthracnose, a post-harvest fungal disease, caused by Colletotrichum gloeosporioides. 1,2,3- triazoles, aromatic nitrogen heterocycles, are already a widely used class of antifungals, showing promise against resistant strains of fungi, due to their different bioactivities and various applications. The aim of the present work is to synthesize and evaluate the antifungal activity against C. gloeosporioides of twenty new compounds containing 1,2,3-triazole moiety (10a-10t), obtained through the click chemistry type reaction and using thymol, as starting material. The synthetic route employed was simple and easy to execute, developed in just three steps. The first step involved the reaction between thymol and (±)-epichlorohydrin, leading to the formation of (±)-2-((2- isopropyl-5-methylphenoxy)methyl)oxirane (1) with a 65% yield. The subsequent step resulted in the formation of (±)-2-(2-isopropyl-5-methylphenoxy)-1-azido-3-propan-2-ol (2), with a 94% yield, from the reaction between (1) and sodium azide in the presence of ammonium chloride. In the third and final step, the click reaction between different terminal alkynes and (2) led to the formation of twenty new 1,2,3-triazole-1,4- disubstituted compounds (10a-10t), with yields ranging from 50% to 80%, using CuSO4.5H2O as a pre-catalyst. The chemical structures of the compounds were elucidated using Infrared, Mass, and Nuclear Magnetic Resonance spectroscopy techniques. In the future, all synthesized compounds will be subjected to biological assays to evaluate their fungicidal activity against C. gloeosporioides, responsible for causing significant damage to papaya, an important crop in Espírito Santo
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