新型偶氮和偶氮化合物的设计、合成、杀线虫和杀菌活性。

Design, Synthesis, Nematicidal, and Fungicidal Activities of Novel Azo and Azoxy Compounds.

机构信息

Collaborative Innovation Center of Green Pesticide, National Joint Engineering Laboratory of Biopesticide Preparation, Zhejiang A&F University State Key Laboratory of Subtropical Silviculture, 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. 2024 Feb 7;72(5):2473-2481. doi: 10.1021/acs.jafc.3c04847. Epub 2024 Jan 29.

DOI:10.1021/acs.jafc.3c04847

PMID:38284538

Abstract

() and are parasitic nematodes that have caused severe ecological and economic damage in pinewood and crops, respectively. Jietacins (jietacin A and B) were found to have excellent biological activity against . Based on our tremendous demand for chemicals against , a novel scaffold based on the azo and azoxy groups was designed, and a series of compounds were synthesized. In the bioassay, , , , , and exhibited higher activity against than avermectin (LC = 2.43 μg·mL) with LC values of 1.37, 1.12, 0.889, 1.56, and 1.10 μg·mL, respectively. Meanwhile, , , , and showed good inhibition effects against at the concentrations of 80 and 40 μg·mL with inhibition rates of 89.0% and 81.6%, 95.6% and 75.7%, 96.3% and 41.2%, and 86.8% and 78.7%, respectively. In fungicidal activity , and exhibited excellent effect against with the inhibition of 82.59% and 85.32% at the concentration of 10 μg·mL, while the inhibition of was 83.16% against at the concentration of 12.5 μg·mL. Referring to the biological activity against , a 3D-QASR model was built in which the electron-donating group and small group at the 4-phenylhydrazine were favorable for the activity. In general, the novel azoxy compounds, especially possess great potential for application in the prevention of .

摘要

松材线虫和水稻干尖线虫分别是寄生在松科植物和水稻上的两种重要的植物寄生性线虫，它们给我国的林业和农业生产带来了严重的经济损失。研究发现，节支菌素（节支菌素 A 和 B）对水稻干尖线虫具有优异的生物活性。基于我们对防治线虫类化学农药的巨大需求，设计了一个基于偶氮和偶氮氧基的新型骨架，并合成了一系列化合物。在生物测定中，化合物、、、、和对水稻干尖线虫的活性明显高于阿维菌素（LC = 2.43 μg·mL ），LC 值分别为 1.37、1.12、0.889、1.56 和 1.10 μg·mL 。同时，化合物、、、和对 3 龄幼虫的抑制活性较好，在 80 和 40 μg·mL 时，抑制率分别为 89.0%和 81.6%、95.6%和 75.7%、96.3%和 41.2%、86.8%和 78.7%。在抑菌活性方面，化合物、对番茄早疫病菌的抑制活性较好，在 10 μg·mL 时，抑制率分别为 82.59%和 85.32%，而化合物对番茄灰霉病菌的抑制率为 83.16%，在 12.5 μg·mL 时。参考生物活性，构建了一个 3D-QASR 模型，结果表明，4-苯肼中电子供体和小基团有利于提高活性。总的来说，新型偶氮氧基化合物，尤其是，具有很大的潜力应用于防治线虫。