Open AccessSYNTHESIS OF GLYCEROL-FLUORINATED TRIAZOLE DERIVATIVES AND EVALUATION OF THEIR FUNGICIDAL ACTIVITY
Author(s) -
Fernando Barcelos,
Lucas F. M. da Silva,
Poliana Gazolla,
Róbson Ricardo Teixeira,
Vagner Tebaldi de Queiroz,
Pedro Morais,
Victor R. Fonseca,
Wanderson Romão,
Valdemar Lacerda Júnior,
Rodrigo Scherer,
Fabrício Singaretti de Oliveira,
Milene Praça-Fontes,
Adílson Vidal Costa
Publication year - 2022
Publication title -
química nova
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.214
H-Index - 73
eISSN - 1678-7064
pISSN - 0100-4042
DOI - 10.21577/0100-4042.20170880
Subject(s) - fungicide , tebuconazole , glycerol , agrochemical , triazole , chemistry , pesticide , proton nmr , organic chemistry , agriculture , biology , botany , agronomy , ecology
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 ressonance (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 (61.35 µg 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.