Suppr超能文献

含羧酰胺片段的新型1,2,4-三唑衍生物的设计、合成及抗真菌/抗卵菌活性

Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments.

作者信息

Wang Jiali, Shi Haoran, Lu Aidang

机构信息

School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300401, China.

出版信息

J Fungi (Basel). 2024 Feb 19;10(2):160. doi: 10.3390/jof10020160.

Abstract

Plant diseases caused by pathogenic fungi or oomycetes seriously affect crop growth and the quality and yield of products. A series of novel 1,2,4-triazole derivatives containing carboxamide fragments based on amide fragments widely used in fungicides and the commercialized mefentrifluconazole were designed and synthesized. Their antifungal activities were evaluated against seven kinds of phytopathogenic fungi/oomycete. Results showed that most compounds had similar or better antifungal activities compared to mefentrifluconazole's inhibitory activity against , especially compound (92%), which possessed outstanding activity. Compound (EC = 13.095 μg/mL) showed a better effect than that of mefentrifluconazole (EC = 39.516 μg/mL). Compound (90%) displayed outstanding anti-oomycete activity against , with an EC value of 17.362 μg/mL, far superior to that of mefentrifluconazole (EC = 75.433 μg/mL). The result of molecular docking showed that compounds and possessed a stronger affinity for 14α-demethylase (CYP51). This study provides a new approach to expanding the fungicidal spectrum of 1,2,4-triazole derivatives.

摘要

由致病真菌或卵菌引起的植物病害严重影响作物生长以及产品的质量和产量。基于广泛用于杀菌剂的酰胺片段和商业化的联苯三唑醇,设计并合成了一系列含有羧酰胺片段的新型1,2,4-三唑衍生物。评估了它们对七种植物病原真菌/卵菌的抗真菌活性。结果表明,与联苯三唑醇对……的抑制活性相比,大多数化合物具有相似或更好的抗真菌活性,尤其是化合物……(92%),其具有出色的活性。化合物……(EC = 13.095 μg/mL)显示出比联苯三唑醇(EC = 39.516 μg/mL)更好的效果。化合物……(90%)对……表现出出色的抗卵菌活性,EC值为17.362 μg/mL,远优于联苯三唑醇(EC = 75.433 μg/mL)。分子对接结果表明,化合物……和……对14α-脱甲基酶(CYP51)具有更强的亲和力。本研究为拓宽1,2,4-三唑衍生物的杀菌谱提供了一种新方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d08f/10890616/7dadf1265cee/jof-10-00160-g001.jpg

相似文献

2
Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide.
J Agric Food Chem. 2023 Apr 26;71(16):6249-6267. doi: 10.1021/acs.jafc.2c09144. Epub 2023 Apr 14.
3
Novel 4-pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity.
Pest Manag Sci. 2019 Nov;75(11):2892-2900. doi: 10.1002/ps.5463. Epub 2019 Jun 17.
4
Discovery of novel salicylaldehyde derivatives incorporating an α-methylene-γ-butyrolactone moiety as fungicidal agents.
Pest Manag Sci. 2023 Dec;79(12):5015-5028. doi: 10.1002/ps.7703. Epub 2023 Aug 24.
8
Design, Synthesis, and Biological Evaluation of Novel Derivatives of the Marine Natural Product Laurene.
J Agric Food Chem. 2023 Oct 11;71(40):14483-14492. doi: 10.1021/acs.jafc.3c03700. Epub 2023 Sep 26.
9
Combinatorial Synthesis of Novel 1-sulfonyloxy/acyloxyeugenol Derivatives as Fungicidal Agents.
Comb Chem High Throughput Screen. 2022;25(9):1545-1551. doi: 10.2174/1386207324666210813114829.
10
Design, synthesis, and biological evaluation of novel berberine derivatives against phytopathogenic fungi.
Pest Manag Sci. 2022 Oct;78(10):4361-4376. doi: 10.1002/ps.7055. Epub 2022 Jul 13.

引用本文的文献

1
Biosynthesis Strategies and Application Progress of Mandelic Acid Based on Biomechanical Properties.
Microorganisms. 2025 Jul 23;13(8):1722. doi: 10.3390/microorganisms13081722.

本文引用的文献

3
High-Resolution Low-Power Hyperspectral Line-Scan Imaging of Fast Cellular Dynamics Using Azo-Enhanced Raman Scattering Probes.
J Am Chem Soc. 2022 Aug 24;144(33):15314-15323. doi: 10.1021/jacs.2c06275. Epub 2022 Aug 15.
4
Repurposing and optimization of drugs for discovery of novel antifungals.
Drug Discov Today. 2022 Jul;27(7):2008-2014. doi: 10.1016/j.drudis.2022.04.021. Epub 2022 Apr 27.
5
Comprehensive Overview of Carboxamide Derivatives as Succinate Dehydrogenase Inhibitors.
J Agric Food Chem. 2022 Feb 2;70(4):957-975. doi: 10.1021/acs.jafc.1c06654. Epub 2022 Jan 18.
7
Novel Pyrazolo[3,4-]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation.
J Agric Food Chem. 2021 Sep 29;69(38):11395-11405. doi: 10.1021/acs.jafc.1c02454. Epub 2021 Sep 15.
8
Absolute Configuration, Enantioselective Bioactivity, and Degradation of the Novel Chiral Triazole Fungicide Mefentrifluconazole.
J Agric Food Chem. 2021 May 5;69(17):4960-4967. doi: 10.1021/acs.jafc.0c07947. Epub 2021 Apr 20.
9
Proteomic Analysis Reveals the Importance of Exudates on Sclerotial Development in .
J Agric Food Chem. 2021 Feb 3;69(4):1430-1440. doi: 10.1021/acs.jafc.0c06685. Epub 2021 Jan 22.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验