Procymidone (Similex®) is a fungicide with a weak anti-androgenic activity. The anti-androgenic activity and androgen receptor (AR)-binding activity of procymidone and its six metabolites were evaluated. Anti-androgenic activity was determined in HeLa cells transiently transfected with an AREx3-luciferase reporter and full-length human or rat AR expression vectors (anti-androgen assay). AR-binding activity was determined by a competitive ligand-binding assay based on a fluorescence polarization method (AR-binding assay). It was clear that procymidone, its hydroxylated metabolite (PCM–CH₂OH), and their imide linkage-cleaved compounds (PCM–NH–COOH and PA–CH₂OH) have anti-androgenic activity and AR-binding activity, and procymidone has the highest activity among these compounds. There were no differences between rats and humans regarding the activities of procymidone and the metabolites. The activity of procymidone was 20–70 times lower than that of hydroxyflutamide, which is a potent anti-androgen. The results indicate that the anti-androgenic activities of procymidone and its metabolites are very weak.

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A series of novel benzamide derivatives with a diphenyl ether moiety were synthesized and evaluated for antifungal and insecticidal activities on the basis of the principle of splicing-up bioactive substructures. Most of the novel benzamide derivatives exhibited moderate to good antifungal activities against five plant pathogen fungi, and compound 17 has shown good antifungal activity against S. ampelimum with EC₅₀ values of 0.95 mg/L and is hoped to be a potential lead compound.

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