Laboratory of Pesticidal Design and Synthesis, Department of Plant Protection, College of Horticulture and Plant Protection, Henan University of Science and Technology, Luoyang, China.
Pest Manag Sci. 2024 Nov;80(11):5746-5758. doi: 10.1002/ps.8306. Epub 2024 Jul 14.
The natural product paeonol is a rich and sustainable natural bioresource, and its derivatives have various unique biological efficacy. As is well known, Schiff bases are a class of organic compounds with a wide range of biological activities, including anti-fungal, insecticidal, anti-viral, and nematicidal.
To discover biorational natural product-based pesticides, nine intermediates (2-10), 12 sulfonylhydrazones (11a-11c, 12a-12c, 13a-13c, and 14a-14c) and 20 benzylidene hydrazones (18a-18r, 19a, and 20a) were synthesized by structural modification of paeonol, and their structures were characterized by proton nuclear magnetic resonance (H NMR), carbon-13 (C) NMR, and high-resolution mass spectrometry (HRMS). The stereochemical configurations of compounds 14a, 18d, and 18r were unambiguously confirmed by single-crystal X-ray diffraction. Furthermore, bioactivities of these compounds as anti-oomycete, anti-fungal, and nematicidal agents against three serious agricultural pests, Phytophthora capsici, Fusarium graminearum, and Heterodera glycines were evaluated. Among all tested compounds: (i) compound 7 exhibited promising anti-oomycete against Phytophthora capsici, with a half maximal effective concentration (EC) value of 15.81 mg L; (ii) compounds 2, 7, 10, and 19a displayed promising anti-fungal against F. graminearum, with EC values of 12.22, 14.72, 23.39, and 33.10 mg L, respectively; (iii) ten compounds (12a-12c, 14c, 18g-18j, 18m, and 19a) showed significant nematicidal activity against H. glycines, with median lethal concentration (LC) values all less than 30.00 mg L. Especially for compound 18g, its LC value is the smallest, at 12.65 mg L.
The research results indicate that introducing nitro groups at the C5 position of paeonol, or introducing halogens at both C5 and C3 positions, can significantly enhance its biological activity against Phytophthora capsici, F. graminearum, and H. glycines. © 2024 Society of Chemical Industry.
天然产物丹皮酚是一种丰富且可持续的天然生物资源，其衍生物具有各种独特的生物功效。众所周知，席夫碱是一类具有广泛生物活性的有机化合物，包括抗真菌、杀虫、抗病毒和杀线虫活性。
为了发现基于天然产物的生物合理农药，通过对丹皮酚进行结构修饰，合成了 9 个中间体（2-10）、12 个磺酰腙（11a-11c、12a-12c、13a-13c 和 14a-14c）和 20 个苯亚甲基腙（18a-18r、19a 和 20a），并通过质子核磁共振（H NMR）、碳-13（C NMR）和高分辨率质谱（HRMS）对其结构进行了表征。化合物 14a、18d 和 18r 的立体化学构型通过单晶 X 射线衍射得到明确确认。此外，还评估了这些化合物作为抗卵菌、抗真菌和杀线虫剂对三种严重农业害虫辣椒疫霉、禾谷镰刀菌和大豆胞囊线虫的生物活性。在所测试的化合物中：（i）化合物 7 对辣椒疫霉表现出有希望的抗卵菌活性，半最大有效浓度（EC）值为 15.81mg/L；（ii）化合物 2、7、10 和 19a 对禾谷镰刀菌表现出有希望的抗真菌活性，EC 值分别为 12.22、14.72、23.39 和 33.10mg/L；（iii）10 个化合物（12a-12c、14c、18g-18j、18m 和 19a）对大豆胞囊线虫表现出显著的杀线虫活性，LC 值均小于 30.00mg/L。特别是化合物 18g 的 LC 值最小，为 12.65mg/L。
研究结果表明，在丹皮酚的 C5 位引入硝基，或在 C5 和 C3 位同时引入卤素，可显著提高其对辣椒疫霉、禾谷镰刀菌和大豆胞囊线虫的生物活性。© 2024 化学学会。
