SÍNTESE E AVALIAÇÃO DA ATIVIDADE ANTIFÚNGICA DE NOVOS DERIVADOS 1,2,3-TRIAZÓLICOS DO GLICEROL CONTRA Asperisporium Caricae, CAUSADOR DA PINTA PRETA DO MAMOEIRO

• Ano de defesa: 2022
• Autor(a) principal: Carvalho, Arlan Figueiredo de
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal do Espírito Santo; BR; Mestrado em Agroquímica; Centro de Ciências Exatas, Naturais e da Saúde; UFES; Programa de Pós-Graduação em Agroquímica
• Palavras-chave em Português: Asperisporium Caricae; Varíola; Mamão; Glicerol; Fungicida; Triazol; Reação CuAAC; subject.br-rjbn; Agronomia
• Link de acesso: http://repositorio.ufes.br/handle/10/16044

The use of antifungal agents has great relevance both in the pharmaceutical and agricultural areas, in the latter, it is used to combat diseases such as papaya smallpox (caused by Asperisporium Caricae) that have been difficult to control. Thus, it is necessary to develop new agrochemicals that will help fight the disease, control, and conserve the fruit after harvest, in addition to targeting compounds with low toxicity and low resistance of the pathogen. The present work aimed to obtain thirteen new 1,2,3-triazole derivatives in a route that starts with glycerol, using nucleophilic substitution reactions and the CuAAC reaction (Cyclocation between Alkyne and Azide catalyzed by Copper(I)). The synthesized compounds were fully characterized using 1H and 13C nuclear magnetic resonance spectroscopy, infrared spectrometry, and mass spectrometry. Considering the antifungal potential of triazoles described in the literature, in vitro and in vivo inhibition tests (papaya) of the synthesized compounds against the fungus Asperisporium Caricae were performed. The results obtained showed that the reactions had satisfactory yields (between 57 % and 91 %), where the reactivity of the alkynes was related to the nature and position of the substituent groups of the benzene ring. Regarding position, the para-substituted ones had higher yield values, while for the different types of substituents the methoxyl group showed the lowest conversions for the different types of substituents. Four triazoles had inhibition of germination the species A. Caricae greater than 75 % (statistically equivalent by the Scott-Knott test), they are: 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-(2-chlorophenyl)-1H-1,2,3-triazole (4b), 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-(4-chlorophenyl)-1H-1,2,3-triazole (4c), 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-(3-chlorophenyl)-1H-1,2 ,3-triazole (4d) and 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-(2-methoxyphenyl)-1H-1,2,3-triazole (4l). The result demonstrates that four triazoles, only 4l does not present the chlorine group in its composition, evidencing that the presence of the chlorine group may have intensified the observed activity of the compounds against A. Caricae. In the in vivo antifungal activity evaluation test, it was observed that for the concentrations 750 mg•L-1, 1000 mg•L-1, 1500 mg•L-1 e 2000 mg•L-1 using triazole (4d) the severity is reduced to values ​​0.45 %; 0.275 %; 0.325 % e 0.675 %. Both the severity and the Area Under the Progression Curve of Disease (AACPD, in Portuguese) had a quadratic behavior in relation to the test concentration, allowing to obtain the optimal theoretical inhibition concentration: 1334.197 mg·L-1 for the severity and 1326.48 mg·L-1 for the AACPD. Therefore, the results of this work are promising regarding the antifungal action potential of the triazoles tested in combating papaya black spot.