A series of novel pyrazole and triazole derivatives containing 5-phenyl-2-furan functionality were designed and synthesized. Their toxicities were predicted using in silico assays and proven to be less toxic. The antitumor results showed that the activity of compounds containing 1,3,4-triazole (series II) was higher than that of pyrazole-attached derivatives (series I). Among them, IIa and IIg showed much higher activity against Bel-7402 than doxorubicin. The fungicidal tests showed that most title compounds II exhibited great selectivity against Phytophthora capsici in vivo.