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合成阿朴松脂酸三唑衍生物及其对. 的抗真菌活性

Synthesis of Acrylopimaric Acid Triazole Derivatives and Their Antioomycete Activity against .

机构信息

Jiangsu Province Key Laboratory of Biomass Energy and Materials, College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.

College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.

出版信息

J Agric Food Chem. 2024 Jan 17;72(2):973-982. doi: 10.1021/acs.jafc.3c04148. Epub 2024 Jan 3.

Abstract

To develop new antioomycete agents against plant pathogens, two series of acrylopimaric acid triazole derivatives from rosin were synthesized. The antioomycete activity of these derivatives was evaluated and screened against , , , , and . Compound showed the highest antioomycete activity against , with a half-maximal effective concentration (EC) value that was lower than that of the positive control metalaxyl (1.391 and 1.815 mg/L, respectively). Compound demonstrated satisfactory protective and curative efficacy against in pepper in antioomycete activity studies. Physiological and biochemical testing showed that the action mechanism of compound on involved altering the morphology and ultrastructure of the mycelium, increasing cell membrane permeability, inducing dysfunction of the nucleus and mitochondria, and ultimately causing cell necrosis. In addition, the analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) revealed the significance of the molecular structure and charge distribution in the interaction between compound and its target. Collectively, these findings indicate that compound has the potential as an antioomycete candidate.

摘要

为了开发针对植物病原菌的新型杀真菌剂,我们从松香中合成了两类丙烯海松酸三唑衍生物。评估了这些衍生物对、、、、和的杀真菌活性,并进行了筛选。化合物对表现出最高的杀真菌活性,其对的半数有效浓度 (EC) 值低于阳性对照金属砜(分别为 1.391 和 1.815 mg/L)。化合物在辣椒中对的防治效果良好,在防治真菌病害的活性研究中表现出令人满意的防治效果。生理生化测试表明,化合物对的作用机制涉及改变菌丝的形态和超微结构、增加细胞膜通透性、诱导细胞核和线粒体功能障碍,最终导致细胞坏死。此外,三维定量构效关系 (3D-QSAR) 分析揭示了化合物与靶标相互作用中分子结构和电荷分布的重要性。综上所述,这些发现表明化合物具有作为杀真菌候选物的潜力。

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