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Barcelos, Fernando Fontes; Scherer, Rodrigo; Silva, Lucas Fagundes da; Gazolla, Poliana Aparecida Rodrigues; Teixeira, Róbson Ricardo; Queiroz, Vagner Tebaldi de; Morais, Pedro Alves Bezerra; Fonseca, Victor da Rocha; Romão, Wanderson; Lacerda Júnior, Valdemar; Praça-Fontes, Milene Miranda; Costa, Adilson Vidal; Oliveira, Fabrício Marques de, E-mail: avcosta@hotmail.com2022
AbstractAbstract
[en] The control of fungal species in agriculture is mainly conducted with the use of contact or systemic fungicides. However, environmental and human health concerns and increased resistance of fungal species to existing fungicides have increased the pressure on researchers to find new active ingredients for fungal control which present low toxicity to non-target organisms, are environmentally safe, and can be applied at very low concentrations. It is herein described the synthesis of eleven glycerol triazole containing compounds (ten of them fluorinated derivatives) and evaluation of their fungicidal activity. Eight out of eleven synthesized compounds are novel and all of the glycerol derivatives were characterized using infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) techniques. Theoretical calculations were also carried out and the results are discussed. Starting from glycerol, the triazole derivatives were prepared in four steps. Evaluation of them against Colletrotricum gloesporioides showed that compound 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-(2-fluorophenyl)-1H-1,2,3-triazole (4d) (ED50 = 59.14 μg mL-1) was slightly more active than commercial fungicide tebuconazole (61.35μg mL-1). Compound 4d presented attractive physicochemical features for agrochemical purposes as revealed by the calculated physicochemical parameters. It is believed that glycerol-fluorinated triazole derivatives can be explored towards the development of new chemicals for the control of fungal species. (author)
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Source
Available from: https://www.scielo.br/j/qn/a/PMr7qmjTSpJ9TQpmrp7LKjr/?format=pdf& lang=en
Record Type
Journal Article
Journal
Quimica Nova (Online); ISSN 1678-7064; ; v. 45(7); p. 788-796
Country of publication
ALCOHOLS, AROMATICS, AZOLES, CARBON ISOTOPES, EVEN-ODD NUCLEI, HALOGENATED AROMATIC HYDROCARBONS, HETEROCYCLIC COMPOUNDS, HYDROCARBONS, HYDROGEN ISOTOPES, HYDROXY COMPOUNDS, ISOTOPES, LIGHT NUCLEI, MAGNETIC RESONANCE, NUCLEI, ODD-EVEN NUCLEI, ORGANIC COMPOUNDS, ORGANIC FLUORINE COMPOUNDS, ORGANIC HALOGEN COMPOUNDS, ORGANIC NITROGEN COMPOUNDS, PESTICIDES, PLANTS, RESONANCE, SPECTRA, SPECTROSCOPY, STABLE ISOTOPES
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