In this paper 25 novel 5‐trifluoromethyl‐1H‐pyrazole‐4‐carboxamide derivatives were designed, synthesized, and evaluated for their in vitro anticancer and antifungal activities; some exhibited good anticancer activity against cancer cells and antifungal activity against fungi. The IC50 values of T1, T4, T6, and T7 against A549 cells were 24.9, 21.9, 14.0, and 10.2 μM, respectively, and those of T15 against Thanatephorus cucumeris and Botryosphaeria dothidea were 22.0 and 27.7 μg/ml, respectively. A morphological study using FM and SEM demonstrated that T15 destroys the integrity and permeability of the T. cucumeris cell membrane. The results of molecular docking between T15 and SDH (PDB code: 2FBW) indicated that amide and trifluoromethyl might be the key functional groups for target compounds with high fungicidal activities. [ABSTRACT FROM AUTHOR]