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. 2022 Aug;78(8):3442-3455. doi: 10.1002/ps.6985. Epub 2022 Jun 3.
Paeonol is extracted and isolated as a rich and sustainable natural bioresource from the root bark of Paeonia suffruticosa, the derivatives of which exhibit numerous biological activities. It is well known that ester compounds play a very important role in pest control, such as organophosphorus, carbamate and pyrethroid pesticides.
To discover biorational natural product-based pesticides, three series of (60) paeonol ester derivatives (7a-t, 8g,p, 9g,p, 10g-j,n-u, 11g,u, 12g,u, 13a-p, 14b,c, and 15b,c) were prepared by structural modification of paeonol, and their structures were well characterized by proton nuclear magnetic resonance ( H-NMR), carbon-13 nuclear magnetic resonance ( C-NMR), high-resolution mass spectrometry (HRMS), and melting point. Furthermore, we assessed the compounds as insecticidal, nematicidal, and anti-oomycete agents against three serious agricultural pests, Mythimna separata, Heterodera glycines, and Phytophthora capsici. Among all tested compounds: (i) compound 8p showed more significant insecticidal activity than toosendanin, and the final mortality rates of 8p and toosendanin against M. separata (1 mg mL ) were 70.4%, and 51.9%, respectively; (ii) compound 7a exhibited more promising nematicidal activity than paeonol, and the median lethal concentration (LC ) values of 7a and 1 against H. glycines were 15.47 and 50.80 mg L , respectively; (iii) compounds 7n and 13m displayed more significant anti-oomycete activity compared to zoxamide against Phytophthora capsici, and the median effective concentration (EC ) values of 7n, 13m, and zoxamide were 23.72, 24.51, and 26.87 mg L , respectively; and the protective effect of the compounds against Phytophthora capsici in vivo further confirmed the effectiveness of the agents.
This study suggested that the introduction of a nitro at the C5 or C3 position of paeonol could improve its bioactivity against M. separata, H. glycines, and Phytophthora capsici. © 2022 Society of Chemical Industry.
丹皮酚是从牡丹皮中提取和分离出来的一种丰富且可持续的天然生物资源，其衍生物表现出许多生物活性。众所周知，酯类化合物在害虫防治中起着非常重要的作用，如有机磷、氨基甲酸酯和拟除虫菊酯类杀虫剂。
为了发现基于生物合理的天然产物的杀虫剂，我们通过丹皮酚的结构修饰，制备了三个系列（60）丹皮酚酯衍生物（7a-t、8g,p、9g,p、10g-j,n-u、11g,u、12g,u、13a-p、14b,c 和 15b,c），其结构通过质子核磁共振（H-NMR）、碳-13 核磁共振（C-NMR）、高分辨率质谱（HRMS）和熔点进行了很好的表征。此外，我们评估了这些化合物作为杀虫剂、杀线虫剂和抗卵菌剂对三种严重农业害虫斜纹夜蛾、大豆胞囊线虫和辣椒疫霉的活性。在所测试的化合物中：（i）化合物 8p 表现出比川楝素更强的杀虫活性，8p 和川楝素对斜纹夜蛾（1mg/mL）的最终死亡率分别为 70.4%和 51.9%；（ii）化合物 7a 表现出比丹皮酚更强的杀线虫活性，7a 和 1 对大豆胞囊线虫的半数致死浓度（LC）值分别为 15.47 和 50.80mg/L；（iii）与唑酰胺相比，化合物 7n 和 13m 对辣椒疫霉表现出更强的抗卵菌活性，7n、13m 和唑酰胺的有效中浓度（EC）值分别为 23.72、24.51 和 26.87mg/L；化合物在体内对辣椒疫霉的保护作用进一步证实了这些药剂的有效性。
本研究表明，丹皮酚 C5 或 C3 位引入硝基可以提高其对斜纹夜蛾、大豆胞囊线虫和辣椒疫霉的生物活性。© 2022 化学学会。
