Design, Synthesis, and Nematocidal Evaluation of Waltherione A Derivatives: Leveraging a Structural Simplification Strategy

• Published in: International journal of molecular sciences Vol. 25; no. 17; p. 9209
• Main Authors: Hu, Zhan, Yang, Bin, Zheng, Shuai, Zhao, Ke, Wang, Kaifeng, Sun, Ranfeng
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 25.08.2024
• Subjects: Agricultural production; Animals; Antinematodal Agents - chemical synthesis; Antinematodal Agents - chemistry; Antinematodal Agents - pharmacology; Botrytis - drug effects; Cucumis sativus - microbiology; Cucumis sativus - parasitology; designed and synthesized; Drug Design; fungicide; Fungicides, Industrial - chemical synthesis; Fungicides, Industrial - chemistry; Fungicides, Industrial - pharmacology; Insecticides; Molecular Structure; Natural products; nematicides; Nematoda - drug effects; Nematodes; Pathogens; Pesticides; Plant Diseases - microbiology; Plant Diseases - parasitology; Plant Diseases - prevention & control; Plant resistance; quinoline and quinolone derivatives; Quinolines - chemical synthesis; Quinolines - chemistry; Quinolines - pharmacology; Quinolones - chemical synthesis; Quinolones - chemistry; Quinolones - pharmacology; Structure-Activity Relationship; Tylenchoidea - drug effects; Waltherione A; Waltherione A; quinoline and quinolone derivatives; nematicides; designed and synthesized; fungicide
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms25179209

Southern root-knot nematodes are among the most pernicious phytoparasites; they are responsible for substantial yield losses in agricultural crops worldwide. The limited availability of nematicides for the prevention and control of plant-parasitic nematodes necessitates the urgent development of novel nematicides. Natural products have always been a key source for the discovery of pesticides. Waltherione A, an alkaloid, exhibits potent nematocidal activity. In this study, we designed and synthesized a series of quinoline and quinolone derivatives from Waltherione A, leveraging a strategy of structural simplification. Bioassays have revealed that the quinoline derivatives exhibit better activity than quinolone derivatives in terms of both nematocidal and fungicidal activities. Notably, compound D1 demonstrated strong nematocidal activity, with a 72 h LC of 23.06 μg/mL, and it effectively controlled the infection of root-knot nematodes on cucumbers. The structure-activity relationship suggests that the quinoline moiety is essential for the nematocidal efficacy of Waltherione A. Additionally, compound D1 exhibited broad-spectrum fungicidal activity, with an EC of 2.98 μg/mL against . At a concentration of 200 μg/mL, it significantly inhibited the occurrence of on tomato fruits, with an inhibitory effect of 96.65%, which is slightly better than the positive control (90.30%).