Using piperitone as the raw material, 42 novel(Z)-/(E)-piperitone-based pyrazole-oxime ester(compounds 6a-6u, including 21 pairs of Z/E isomers) were synthesized through O-acylation reactions with substituted pyrazoles after carbonyl oximation. The structures of the target products were characterized using proton-1 nuclear magnetic resonance spectrum(1H NMR), carbon-13 nuclear magnetic resonance spectrum(13C NMR), Fourier-transform infrared spectroscopy(FT-IR), and high-resolution mass spectrometry(HRMS). The Z/E configurations of the compounds were determined by single-crystal X-ray diffraction analysis(SC-XRD). In vitro bioactivity tests showed that the(Z)-/(E)-piperitone-based pyrazole-oxime ester compounds exhibited certain antifungal activities against eight plant pathogenic bacteria, including Fusarium oxysporum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoctonia solani, Bipolaris maydis, and Colleterichum orbiculare, at a mass concentration of 50 mg/L. The antibacterial activity was significantly influenced by the Z/E configurations of the compounds, and their activities against A. solani were found to be the most efficient. Wherein, (Z)-piperitone-based(3′, 5′-difluoromethyl)phenyl pyrazole-oxime ester((Z)-6o), (Z)-piperitone-based(p-trifluoromethyl)phenyl pyrazole-oxime ester((Z)-6u), (Z)-piperitone-based(p-nitro)phenyl pyrazole-oxime ester((Z)-6p), (E)-piperitone-based(p-nitro)phenyl pyrazole-oxime ester((E)-6p), (Z)-piperitone-based(p-trifluoromethoxy)phenyl pyrazole-oxime ester((Z)-6g), and(E)-piperitone-based(o-fluoro)phenyl pyrazole-oxime ester((E)-6i) exhibited the inhibition rates of 83.8%, 78.7%, 76.3%, 76.3%, 74.8%, and 74.3%, respectively, against A. solani. And compound(Z)-6u showed the inhibition rate of 82.5% against P. piricola, which was better than that of the positive control chlorothalonil. The three-dimensional quantitative structure-activity relationship(3D-QSAR) model(r2=0.928, q2=0.732) for the inhibitory activity of(Z)-piperitone-based pyrazole-oxime ester compounds against A. solani was established using comparative molecular field analysis(CoMFA) method.