Abstract: In order to develop potential glucosamine-6-phosphate synthase (GlmS) inhibitors and anti-fungal agents, 30 oleanolic acid oxime ethers were synthesized in an efficient way, and 29 of them were new compounds. The structures of all the synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS. Preliminary studies based on the Elson-Morgan method and mycelial growth rate method indicated that, many compounds exhibited inhibitory activities against GlmS at the concentration of 0.35 mmol/L. And the inhibition rate of compounds A-01, A-02, A-04, C-04 and C-05 were about 30%. The original fungicidal activities results showed that some of the compounds exhibited good fungicidal activities to Sclerotinia sclerotiorum (Lib.) de Bary, Botrytis cinerea Pers. and Pyricularia oryzae Cav. at the concentration of 50 μg/mL. And the inhibition rate of compounds A-01, A-02, A-04, A-05 and B-02 against S. sclerotiorum were about 88%. These compounds will be further studied as potential antifungal lead compounds.