Abstract

A series of novel thiochromanone derivatives containing a sulfonyl hydrazone moiety were designed and synthesized. Their structures were determined by 1H-NMR, 13C-NMR, and HRMS. Bioassay results showed that most of the target compounds revealed moderate to good antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri. Compound 4i had the best inhibitory activity against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri, with the EC50 values of 8.67, 12.65, and 10.62 μg/mL, which were superior to those of Bismerthiazol and Thiodiazole-copper. Meanwhile, bioassay results showed that all of the target compounds proved to have lower antifungal activities against Sclerotinia sclerotiorum, Fusarium oxysporum, Gibberella zeae, Rhizoctonia solani, Verticillium dahlia, and Botrytis cinerea than those of Carbendazim.

Highlights

  • IntroductionPublisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations

  • Thiochromanone, a kind of chromone compound, is an important substance in the synthesis of various active molecules that are extensively used in the intermediate skeleton of drugs and has attracted more and more attention due to their extensive biological activities, including antiviral [10], antibacterial [11,12], antifungal [11,13,14,15], herbicidal [16,17], and insecticidal [18]

  • Asterisk (*) indicated the inhibition rates of the target compounds with significant difference at p < 0.05 compared with those of positive controls Bismerthiazol and Thiodiazole-copper

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Summary

Introduction

Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. Thiochromanone, a kind of chromone compound, is an important substance in the synthesis of various active molecules that are extensively used in the intermediate skeleton of drugs and has attracted more and more attention due to their extensive biological activities, including antiviral [10], antibacterial [11,12], antifungal [11,13,14,15], herbicidal [16,17], and insecticidal [18]. Molecules 2021, 26, 2925 substance in the synthesis of various active molecules that are extensively used in the in of 8 termediate skeleton of drugs and has attracted more and more attention due to their extensive biological activities, including antiviral [10], antibacterial [11,12], antifungal [11,13,14,15], herbicidal [16,17], and insecticidal [18] activity.

Discussion
Biological Evaluations
General Information
Preparation Procedure of Intermediates 2 and 3
Preparation Procedure of the Target Compound 4a–4r
In Vitro Antibacterial Activity Test
In Vitro Antifungal Activity Test
Statistical Analysis
Conclusions
Full Text
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