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Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

Caixia Wang, Liangxin Fan, Zhenliang Pan, Sufang Fan, Lijun Shi, Xu Li, Jinfang Zhao, Lulu Wu, Guoyu Yang, Cuilian Xu

2022Molecules31 citationsDOIOpen Access PDF

Abstract

A series of novel indole Schiff base derivatives (2a–2t) containing a 1,3,4-thiadiazole scaffold modified with a thioether group were synthesized, and their structures were confirmed using FT-IR, 1H NMR, 13C NMR, and HR-MS. In addition, the antifungal activity of synthesized indole derivatives was investigated against Fusarium graminearum (F. graminearum), Fusarium oxysporum (F. oxysporum), Fusariummoniliforme (F.moniliforme), Curvularia lunata (C. lunata), and Phytophthora parasitica var. nicotiana (P. p. var. nicotianae) using the mycelium growth rate method. Among the synthesized indole derivatives, compound 2j showed the highest inhibition rates of 100%, 95.7%, 89%, and 76.5% at a concentration of 500 μg/mL against F. graminearum, F. oxysporum, F.moniliforme, and P. p. var. nicotianae, respectively. Similarly, compounds 2j and 2q exhibited higher inhibition rates of 81.9% and 83.7% at a concentration of 500 μg/mL against C. lunata. In addition, compound 2j has been recognized as a potential compound for further investigation in the field of fungicides.

Topics & Concepts

Fusarium oxysporumIndole testSchiff baseMyceliumFungicideStereochemistryFusariumAntifungalProton NMRTwo-dimensional nuclear magnetic resonance spectroscopyCarbon-13 NMRChemistryBiologyBotanyMicrobiologyPlant Pathogens and Fungal DiseasesFungal Plant Pathogen ControlEssential Oils and Antimicrobial Activity