| Summary: | <i>Botrytis cinerea</i> 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 <b>L1</b> [(<i>E</i>)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-<i>tert</i>-butylphenol], a pyridine Schiff base harboring an intramolecular bond (IHB), regarding their antifungal activity against <i>Botrytis cinerea</i>. Moreover, we present a full characterization of the <b>L1</b> 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 <b>L1</b>. Finally, we tested the antifungal activity of <b>L1</b> against two strains of <i>Botrytis cinerea</i> (B05.10, a standard laboratory strain; and A1, a wild type strains isolated from Chilean blueberries). We found that <b>L1</b> acts as an efficient antifungal agent against <i>Botrytis cinerea</i> 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.
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