Liu Yibo, Tian Yuee, Peng Hong, Zhang Fulong, Huang Xiaobo, Chen Genqiang, Zhou Lin, Che Zhiping
Laboratory of Pesticidal Design & Synthesis, Department of Plant Protection, College of Horticultrue and Plant Protection, Henan University of Science and Technology, Luoyang 471023, China.
Henan Provincial Plant Protection and Quarantine Station, Zhengzhou 450002, China.
J Agric Food Chem. 2025 Apr 23;73(16):9533-9540. doi: 10.1021/acs.jafc.4c11375. Epub 2025 Apr 10.
Paeonol is the main active ingredient in the Chinese medicinal herb peony root bark. To discover biorational natural product-based fungicides, 25 paeonol derivatives (-) containing a pyrazole ring were designed and synthesized by ingeniously introducing a pyrazole five-membered heterocyclic ring, and their structures were well characterized by H NMR, C NMR, high-resolution mass spectrometer (HRMS), and m.p. The stereochemical configurations of six target compounds, , , , , , and , were unambiguously subjected to single-crystal X-ray diffraction. Furthermore, we evaluated the bioactivities of these target compounds as anti-oomycete and antifungal agents against two serious agricultural diseases, and . Among all tested compounds, (1) nine compounds -, , , , , , displayed promising anti-oomycete against , with EC values ranging from 22.1 to 34.5 mg/L, and the protective effect of the target compounds against further confirmed the above results. (2) Six compounds , , , , , displayed promising antifungal against , with EC values ranging from 38.2 to 86.0 mg/L. Moreover, some interesting results of structure-activity relationships were also observed. The results of this study pave the way for further design, synthesis, and development of paeonol derivatives as potential botanical anti-oomycete and antifungal agents in crop protection.
丹皮酚是中药牡丹皮的主要活性成分。为了发现基于生物合理天然产物的杀菌剂，通过巧妙引入吡唑五元杂环设计并合成了25种含吡唑环的丹皮酚衍生物（-），其结构通过1H NMR、13C NMR、高分辨率质谱仪（HRMS）和熔点进行了充分表征。六种目标化合物，即，，，，，和，的立体化学构型通过单晶X射线衍射得到明确确定。此外，我们评估了这些目标化合物作为抗卵菌剂和抗真菌剂对两种严重农业病害，即和的生物活性。在所有测试化合物中，（1）九种化合物 - ，，，，，，对表现出有前景的抗卵菌活性，EC值范围为22.1至34.5 mg/L，目标化合物对的保护作用进一步证实了上述结果。（2）六种化合物，，，，，对表现出有前景的抗真菌活性，EC值范围为38.2至86.0 mg/L。此外，还观察到了一些有趣的构效关系结果。本研究结果为进一步设计、合成和开发丹皮酚衍生物作为作物保护中潜在的植物源抗卵菌和抗真菌剂铺平了道路。
