ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Design, synthesis and fungicidal activities evaluation of N-(thiazol-4-ylmethyl) benzenesulfonamide derivatives

Shumin Zheng and Danling Huang

College of Pharmaceutical Sciences, Yunnan University of Chinese Medicine, Kunming, People’s Republic of China

E-mail: leonchemistry@szu.edu.cn

Received: 18 August 2022  Accepted: 9 October 2022

Abstract:

A series of N-(thiazol-4-ylmethyl) benzenesulfonamide derivatives were designed, synthesized, and characterized by ¹H NMR, ¹³C NMR, and HRMS. The evaluation of fungicidal activities against Fusarium oxysporum (F. oxysporum), Sclerotinia sclerotiorum (S. sclerotiorum), Botrytis cinerea (B. cinerea), Colletotrichum fragariae (C. fragariae), Alternaria alternata (A. alternata), Penicillium digitatum (P. digitatum), Curvularia lunata (C. lunata), and Curvularia mebaldsii (C. mebaldsii) for the target compounds was carried out. The results indicated that this series of compounds were sensitive to C. lunata, B. cinerea, and S. sclerotiorum. Especially, 2,4-dichloro-N-((2-phenylthiazol-4-yl)methyl)benzenesulfonamide (5c) exhibited the best bioactivities against C. lunata, B. cinerea, and S. sclerotiorum with EC₅₀ value of 20.8 mg/L (52.3 μM), 24.6 mg/L (61.8 μM), and 9.5 mg/L (23.9 μM), respectively, which has equivalent or superior fungicidal activity to commercial products hymexazol. Furthermore, the structure–activity relationship was given, which might be contribution to the design and discovery of N-(thiazol-4-ylmethyl)benzenesulfonamide derivatives as novel fungicide.

Keywords: Thiazole; Sulfonamide; Fungicidal activity; Structure–activity relationship

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02540-2

Chemical Papers 77 (2) 1059–1066 (2023)