Abstract
Triadimefon (TDM) and cyproconazole (CPZ) are two triazoles widely used as fungicides. Several azoles were synthesised starting from commercial TDM and CPZ. The compounds were evaluated against phytopathogenic filamentous fungi, including Aspergillus fumigatus (AF), A. niger (AN), A. ustus (AU), A. japonicus (AJ), A. terreus (AT), Fusarium oxysporum and Botrytis cinerea isolated from grapevine in the province of San Juan, Argentina. Three of the synthesised compounds (1-(Biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one, 1; 2-(Biphenyl-4-yl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, 3; 3-Cyclopropyl-2-(4’-fluorobiphenyl-4-yl)-1-(1H-1,2,4-triazol1-yl)butan-2-ol, 4) presented remarkable in vitro fungicidal properties, with better effects than TDM and CPZ on some of the target fungi. Cytotoxicity was assessed using human lung fibroblasts MRC5. Derivative 1, with IC50 values of 389.4 µM, was less toxic towards MRC-5 human lung fibroblasts than commercial TDM (248.5 µM) and CPZ (267.4 µM). Docking analysis and molecular dynamics simulations suggest that the compounds present the same interaction in the binding pocket of the CYP51B enzyme and with the same amino acids as CPZ. The derivatives investigated could be considered broad-spectrum but with some selectivity towards imperfect fungi.Graphical abstract
Highlights
Table and wine grapes (Vitis vinifera L.) as well as other relevant crops, including tomatoes (Solanum lycopersicum), apples, pears and citrus fruits, are very susceptible to a large number of pathogenic microorganisms such as Botrytis cinerea, Aspergillus spp., and Fusarium spp., among others
Micrographs of B. cinerea mycelium treated with derivative 4 (12.5 μg/mL) showed morphological alterations, including irregular hyphae, variable diameter and the presence of internal vacuoles, which were not observed in untreated mycelia. These results showed that B. cinerea is affected by compound 4, which causes widespread damage, including cytosolic vacuoles, hyster disruption and hyphal wall lysis
Compounds 5, 6 (Additional file 1: Figure S1) and 7 (Fig. 7) show much weaker interactions than compounds 3 and 4. These results suggest that the azoles investigated have similar interactions to those of VOR and CPZ in the active site of BcCYP51
Summary
Table and wine grapes (Vitis vinifera L.) as well as other relevant crops, including tomatoes (Solanum lycopersicum), apples, pears and citrus fruits, are very susceptible to a large number of pathogenic microorganisms such as Botrytis cinerea, Aspergillus spp., and Fusarium spp., among others. Fungal diseases cause economic losses during pre- and/or post-harvest, affecting production, processing and export, together with the quality of fruit. The grapes infected with moulds suffer alterations in the chemical composition, negatively affecting the flavour and colour of the wine and producing economic losses in the wine industry. The imperfect fungus B. cinerea is the causal agent of grey mould [3, 4]. It poses a major problem for vegetables and fruits during cold storage because the fungus can grow at low temperatures [5]. It is genetically variable and has developed strains resistant to many of the chemicals frequently used for its control [6]
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