Synthesis of paeonol ester derivatives and their insecticidal, nematicidal, and anti‐oomycete activities. Issue 8 (3rd June 2022)

• Record Type: Journal Article
• Authors: Che, Zhiping; Guo, Xiaolong; Li, Yuanhao; Zhang, Song; Zhu, Lina; He, Jiaxuan; Sun, Di; Guo, Yihao; Liu, Yibo; Wei, Ruxue; Huang, Xiaobo; Liu, Shengming; Chen, Genqiang; Tian, Yuee
• Is Part Of: Pest management science. Volume 78:Issue 8(2022)
• Page Start: 3442
• Page End: 3455
• Publication Date: 2022-06-03
• Subjects: Paeonia suffruticosa -- paeonol -- structural modification -- pesticidal activity -- botanical pesticide; Pests -- Control -- Periodicals; Pesticides -- Periodicals; 632.9
• DOI: 10.1002/ps.6985
• Languages: English
• ISSNs: 1526-498X

Abstract

Abstract: Background: 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. Results: 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 ( 1 H‐NMR), carbon‐13 nuclear magnetic resonance ( 13 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 −1 ) were 70.4%, and 51.9%, respectively; (ii) compound 7a exhibited more promising nematicidal activity than paeonol, and the median lethal concentration (LC50 ) values of 7a and 1 against H. glycines were 15.47 and 50.80 mg L −1, respectively; (iii) compounds 7n and 13m displayed more significant anti‐oomycete activity compared to zoxamide against Phytophthora capsici, and the median effective concentration (EC50 ) values of 7n, 13m, and zoxamide were 23.72, 24.51, and 26.87 mg L −1, respectively; and the protective effect of the compounds against Phytophthora capsici in vivo further confirmed the effectiveness of the agents. Conclusion: 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. Abstract : Three series of (60) paeonol ester derivatives have been successfully prepared; the stereochemical configurations of 7p and 10t were unambiguously subjected to single‐crystal X‐ray diffraction; compound 8p showed significant insecticidal activity much higher than toosendanin; compound 7a exhibited more promising nematicidal activity than paeonol; compounds 7n and 13m displayed significant higher anti‐oomycete activity than zoxamide; some interesting results of structure–activity relationships were also observed.