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The antifungal and antiaflatoxigenic effects of two series of coumarinyl thiosemicarbazides on Aspergillus flavus NRRL 3251 were studied. Fungi were grown in YES medium for 72 h at 29 °C in the presence of 0, 0.1, 1, and 10 µg mL-1 of coumarinyl thiosemicarbazides: one series with substitution in position 7 and another with substitution in position 4 of the coumarin core. Dry mycelia weight determination was used for antifungal activity estimation, while the aflatoxin B1 content in YES media, determined by the dilute and shoot LC-MS/MS technique, was used for the antiaflatoxigenic effect estimation. Standard biochemical assays were used for oxidative status marker (TBARS, SOD, CAT, and GPX) determination in A. flavus NRRL 3251 mycelia. Results show that 7-substituted-coumarinyl thiosemicarbazides possess a better antifungal and antiaflatoxigenic activity than 4-substituted ones. The most prominent substituted compound was the compound 3, N-(4-chlorophenyl)-2-(2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)hydrazine-1-carbothioamide, which completely inhibited aflatoxin production at the concentration of 10 µg mL-1. Oxidative stress response of A. flavus exposed to the selected compounds points to the modulation of oxidative stress as a possible reason of aflatoxin production inhibition.