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Consequently, a novel series of vanillin derivatives containing thiazole and hydrazone fragments were strategically designed, synthesized, and evaluated for their antifungal activity against six representative plant phytopathogenic fungi.<\/jats:p><\/jats:sec><jats:sec><jats:title>RESULTS<\/jats:title><jats:p>In the <jats:italic>in vitro<\/jats:italic> antifungal assay, some title vanillin derivatives showed good antifungal activity against <jats:italic>Botrytis cinerea<\/jats:italic>, <jats:italic>Fusarium solani<\/jats:italic>, and <jats:italic>Magnaporthe grisea<\/jats:italic>. Significantly, compound <jats:bold>4a<\/jats:bold> exhibited remarkable broad\u2010spectrum fungistatic potency and displayed the most potent antifungal activity against <jats:italic>B. cinerea<\/jats:italic> and <jats:italic>F. solani<\/jats:italic>, with half maximal effective concentration (EC<jats:sub>50<\/jats:sub>) values of 1.07 and 0.78\u2009\u03bcg\/mL, respectively, substantially surpassing the efficacy of the commercial fungicide hymexazol and comparable to carbendazim. In addition, compound <jats:bold>4k<\/jats:bold> selectively inhibited <jats:italic>M. grisea<\/jats:italic> with the lowest EC<jats:sub>50<\/jats:sub> value of 7.77\u2009\u03bcg\/mL. The <jats:italic>in vivo<\/jats:italic> antifungal assay revealed that compound <jats:bold>4a<\/jats:bold> exhibited superior protective efficacy against <jats:italic>B. cinerea<\/jats:italic> compared to carbendazim. At the same time, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and fluorescent dye staining showed compound <jats:bold>4a<\/jats:bold> exerted its fungicidal activity by damaging the cell wall, cell membrane and mitochondria of <jats:italic>B. cinerea.<\/jats:italic><\/jats:p><\/jats:sec><jats:sec><jats:title>CONCLUSION<\/jats:title><jats:p>Modification of vanillin through electron\u2010withdrawing group substitution and hydrophobic substitution, followed by condensation with thiazole\u20104\u2010carbohydrazide, could result in highly active antifungal derivatives. Among them, compound <jats:bold>4a<\/jats:bold>, which exhibited excellent inhibitory activities <jats:italic>in vitro<\/jats:italic> and <jats:italic>in vivo<\/jats:italic>, could potentially serve as a lead compound. \u00a9 2024 Society of Chemical Industry.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ps.8591","type":"journal-article","created":{"date-parts":[[2024,12,4]],"date-time":"2024-12-04T04:16:29Z","timestamp":1733285789000},"page":"1909-1922","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Design, synthesis and antifungal activity of novel vanillin derivatives containing thiazole and acylhydrazone moieties"],"prefix":"10.1002","volume":"81","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3130-6099","authenticated-orcid":false,"given":"Ding","family":"Li","sequence":"first","affiliation":[{"name":"Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy Northwest A&amp;F University  Yangling P. 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