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The frequency of opportunistic fungal infections has been increasing, impacting agriculture, food, and health sectors. In this work, four thiosemicarbazone-chalcones (TC) were synthesized and evaluated by the radial diffusion method against filamentous fungi. All TCs were effective against Aspergillus parasiticus, especially the fluor-substituted one, with radial growth inhibition of 62,9% and 74,4% at the lower (0.209 µmol/ml) and highest (1.670 µmol/ml) concentrations tested, respectively. On the other hand, the non-substituted derivative was the most active against A. carbonarius, inhibiting radial growth by 47,9% and 74,1% at 0.222 µmol/ml and 1.777 µmol/ml, respectively. Additionally, the compounds were evaluated against the dimorphic fungi Sporothrix brasiliensis, S. schenckii, and a clinical strain of Sporothrix spp, exhibiting minimum inhibitory concentrations (MICs) in the range of 0.396-1.777 µmol/ml. When tested against four yeasts of the Candida genus, the thiosemicarbazone-chalcones demonstrated greater activity against C. krusei (MICs 0.011-0.026 µmol/ml)., Competing Interests: Declarations. Competing interests: The authors declare no competing interests., (© 2024. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)