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含酯基新型氧化偶氮化合物杀线虫和抗真菌活性的设计、合成与评价

Design, Synthesis, and Evaluation of Nematicidal and Antifungal Activities of Novel Azoxy Compounds Incorporating an Ester Moiety.

作者信息

Zhang Yu-Qi, Wang Bo-Ning, Dong Xiao-Xuan, Wu Zhe-Xuan, Liu Ya-Qi, Wang Jun-Kun, Liu Ming, Chen An-Liang, Chen Jie, Zhou Sha

机构信息

Collaborative Innovation Center of Green Pesticide, National Joint Engineering Laboratory of Biopesticide Preparation, National Key Laboratory for Development and Utilization of Forest Food Resources, School of Forestry and Biotechnology, Zhejiang A & F University, Hangzhou, Zhejiang 311300, China.

School of Pharmacy, Binzhou Medical University, Yantai, Shandong 264003, China.

出版信息

J Agric Food Chem. 2025 Jul 23;73(29):18165-18175. doi: 10.1021/acs.jafc.5c02414. Epub 2025 Jul 11.

Abstract

is a parasitic nematode that causes serious ecological and economic harm to pine trees. Taking (LC = 0.889 μg·mL) as the lead compound, 26 azoxy compounds were designed and synthesized. Most of the azoxy compounds showed excellent nematicidal activity, especially , , and , with LC values of 0.424, 0.267, and 0.803 μg·mL, respectively, significantly better than avermectin (LC = 16.4 μg·mL) and emamectin benzoate (LC = 13.3 μg·mL). Scanning electron microscopy (SEM) showed that the nematodes treated with compounds and were severely shrivelled, and there were obvious local depressions and ruptures. Furthermore, the azoxy compounds that had good nematicidal activity against also showed good inhibition against , and compounds , , and showed good root knot inhibition activity. In addition, compound showed good fungicidal activity against and , with EC values of 2.00 and 1.80 μg·mL, respectively. SEM showed that the mycelium of and treated by compound was dry and varied in thickness, and the mycelium of even appeared fracture. A 3D-QASR model was established according to the bioactivity against , and it was advantageous to the promotion of activity when the 4-substituted group is more electronegative and smaller. In conclusion, the novel azoxy compounds, especially , , and , have great potential in the prevention and treatment of .

摘要

是一种寄生线虫,对松树造成严重的生态和经济危害。以(LC = 0.889 μg·mL)为先导化合物,设计并合成了26种氧化偶氮化合物。大多数氧化偶氮化合物表现出优异的杀线虫活性,尤其是,,和,LC值分别为0.424、0.267和0.803 μg·mL,明显优于阿维菌素(LC = 16.4 μg·mL)和甲氨基阿维菌素苯甲酸盐(LC = 13.3 μg·mL)。扫描电子显微镜(SEM)显示,用化合物和处理的线虫严重皱缩,有明显的局部凹陷和破裂。此外,对具有良好杀线虫活性的氧化偶氮化合物对也表现出良好的抑制作用,化合物,,和表现出良好的根结抑制活性。此外,化合物对和表现出良好的杀菌活性,EC值分别为2.00和1.80 μg·mL。SEM显示,用化合物处理的和的菌丝体干燥且厚度不一,的菌丝体甚至出现断裂。根据对的生物活性建立了3D-QASR模型,当4-取代基的电负性更强且更小时,有利于活性的提高。总之,新型氧化偶氮化合物,尤其是,,和,在的防治方面具有巨大潜力。

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