Abstract
Botrytis cinerea is a ubiquitous necrotrophic filamentous fungal phytopathogen that lacks host specificity and can affect more than 1000 different plant species. In this work, we explored L1 [(E)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol], a pyridine Schiff base harboring an intramolecular bond (IHB), regarding their antifungal activity against Botrytis cinerea. Moreover, we present a full characterization of the L1 by NMR and powder diffraction, as well as UV–vis, in the presence of previously untested different organic solvents. Complementary time-dependent density functional theory (TD-DFT) calculations were performed, and the noncovalent interaction (NCI) index was determined. Moreover, we obtained a scan-rate study on cyclic voltammetry of L1. Finally, we tested the antifungal activity of L1 against two strains of Botrytis cinerea (B05.10, a standard laboratory strain; and A1, a wild type strains isolated from Chilean blueberries). We found that L1 acts as an efficient antifungal agent against Botrytis cinerea at 26 °C, even better than the commercial antifungal agent fenhexamid. Although the antifungal activity was also observed at 4 °C, the effect was less pronounced. These results show the high versatility of this kind of pyridine Schiff bases in biological applications.
Highlights
IntroductionPyridine Schiff bases present a full versatility, generally due to the substituents around the azomethine group, allowing their application in diverse areas, including the generation of antimicrobial and antifungal compounds [5,6]
Schiff base compounds are organic compounds containing an azomethine C=N group [1,2,3,4].Pyridine Schiff bases present a full versatility, generally due to the substituents around the azomethine group, allowing their application in diverse areas, including the generation of antimicrobial and antifungal compounds [5,6]
We tested the antifungal activity of L1 against two strains of Botrytis cinerea (B05.10, a standard laboratory strain; and A1, a wild type strains isolated from Chilean blueberries) [22], and other cell models including
Summary
Pyridine Schiff bases present a full versatility, generally due to the substituents around the azomethine group, allowing their application in diverse areas, including the generation of antimicrobial and antifungal compounds [5,6]. CYP51 inhibition, in turn, leads to inhibition of ergosterol biosynthesis in fungi with the concomitant accumulation of toxic metabolites and cell death [14,15,16]. In this sense, pyridine Schiff bases have great potential as antifungal agents, as previously described [7,8,9]
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