Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation

Coumarin compounds have a variety of biological activities such as anti-tumor, anti-coagulation, anti-HIV, anti-fungal, and insecticidal. Amide and sulfonamide compounds have been used as fungicides for half a century, and dozens of varieties have been developed so far. This study focused on the int...

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Main Authors: Shu-Guang Zhang, Yu-Qiang Wan, Ya Wen, Wei-Hua Zhang
Format: Article
Language:English
Published: MDPI AG 2022-10-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/27/20/6904
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author Shu-Guang Zhang
Yu-Qiang Wan
Ya Wen
Wei-Hua Zhang
author_facet Shu-Guang Zhang
Yu-Qiang Wan
Ya Wen
Wei-Hua Zhang
author_sort Shu-Guang Zhang
collection DOAJ
description Coumarin compounds have a variety of biological activities such as anti-tumor, anti-coagulation, anti-HIV, anti-fungal, and insecticidal. Amide and sulfonamide compounds have been used as fungicides for half a century, and dozens of varieties have been developed so far. This study focused on the introduction of carboxamide and sulfonamide moieties in a coumarin core to discover novel derivatives. Based on this strategy, we synthesized two series of novel carboxamide and sulfonamide substituted coumarin derivatives, and their fungicidal activity was also investigated. Some designed compounds possessed potential activities against six phytopathogenic fungi in the primary assays, highlighted by compound <b>6r</b>. Compound <b>6r</b> exhibited stronger fungicidal activity against <i>Botrytis cinerea</i> (EC<sub>50</sub> = 20.52 µg/mL) and will be the lead structure for further study.
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spelling doaj.art-f2a4ee5a4be341449be1bf47e11a97472023-11-24T01:33:29ZengMDPI AGMolecules1420-30492022-10-012720690410.3390/molecules27206904Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological EvaluationShu-Guang Zhang0Yu-Qiang Wan1Ya Wen2Wei-Hua Zhang3Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaCoumarin compounds have a variety of biological activities such as anti-tumor, anti-coagulation, anti-HIV, anti-fungal, and insecticidal. Amide and sulfonamide compounds have been used as fungicides for half a century, and dozens of varieties have been developed so far. This study focused on the introduction of carboxamide and sulfonamide moieties in a coumarin core to discover novel derivatives. Based on this strategy, we synthesized two series of novel carboxamide and sulfonamide substituted coumarin derivatives, and their fungicidal activity was also investigated. Some designed compounds possessed potential activities against six phytopathogenic fungi in the primary assays, highlighted by compound <b>6r</b>. Compound <b>6r</b> exhibited stronger fungicidal activity against <i>Botrytis cinerea</i> (EC<sub>50</sub> = 20.52 µg/mL) and will be the lead structure for further study.https://www.mdpi.com/1420-3049/27/20/6904coumarincarboxamidesulfonamidefungicidal activity
spellingShingle Shu-Guang Zhang
Yu-Qiang Wan
Ya Wen
Wei-Hua Zhang
Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
Molecules
coumarin
carboxamide
sulfonamide
fungicidal activity
title Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
title_full Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
title_fullStr Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
title_full_unstemmed Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
title_short Novel Coumarin 7-Carboxamide/Sulfonamide Derivatives as Potential Fungicidal Agents: Design, Synthesis, and Biological Evaluation
title_sort novel coumarin 7 carboxamide sulfonamide derivatives as potential fungicidal agents design synthesis and biological evaluation
topic coumarin
carboxamide
sulfonamide
fungicidal activity
url https://www.mdpi.com/1420-3049/27/20/6904
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AT yuqiangwan novelcoumarin7carboxamidesulfonamidederivativesaspotentialfungicidalagentsdesignsynthesisandbiologicalevaluation
AT yawen novelcoumarin7carboxamidesulfonamidederivativesaspotentialfungicidalagentsdesignsynthesisandbiologicalevaluation
AT weihuazhang novelcoumarin7carboxamidesulfonamidederivativesaspotentialfungicidalagentsdesignsynthesisandbiologicalevaluation