Synthesis and biological evaluation of 2-(4-substituted benzene-1-sulfonyl)- N' -(substituted-1-sulfonyl)acetohydrazide
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ORIGINAL PAPER
Synthesis and biological evaluation of 2‑(4‑substituted benzene‑1‑sulfonyl)‑N’‑(substituted‑1‑sulfonyl)acetohydrazide as antibacterial agents Pei Li1 · Junliang Zhou2 · Yan Liu3 · Xiang Wang1 Received: 20 January 2020 / Accepted: 27 June 2020 © Institute of Chemistry, Slovak Academy of Sciences 2020
Abstract In this study, a series of new sulfone derivatives containing a sulfonohydrazide moiety were synthesized and their structures were determined using 1H NMR, 13C NMR, and HRMS. Then, the in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) were evaluated by performing turbidimeter test. Bioactivity results showed that compound 2-(4-fluorobenzene-1-sulfonyl)-N′-(4-fluorobenzene-1-sulfonyl)acetohydrazide (5g) revealed the best antibacterial activities against Xoo and Xac, with the 50% effective concentration ( EC50) values of 25 and 36 µg/ mL, respectively, which were superior to those of thiodiazole copper (110 and 230 µg/mL, respectively) and bismerthiazol (84 and 146 µg/mL, respectively). Keywords Sulfone · Sulfonohydrazide · Synthesis · Antibacterial activity
Introduction Rice bacterial leaf blight, caused by Xanthomonas oryzae pv. oryzae (Xoo), can result in leaf blight at the tillering stage and up to 80% yield loss (Ou 1985; Huang et al. 1997). Also, citrus canker, caused by Xanthomonas axonopodis pv. citri (Xac), can significantly affect citrus production (Das 2003; Gottwald et al. 2001). However, long-term use of available
Pei Li and Junliang Zhou contributed equally to this work. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01271-6) contains supplementary material, which is available to authorized users. * Pei Li [email protected] * Xiang Wang [email protected] 1
Qiandongnan Engineering and Technology Research Center for Comprehensive Utilization of National Medicine, Kaili University, Kaili 556011, People’s Republic of China
2
Guizhou Fruit Institute, Guizhou Academy of Agricultural Sciences, Guiyang 550025, People’s Republic of China
3
National Chemical Low Carbon Technology and Engineering Center, Kunshan 215300, People’s Republic of China
traditional bactericides not only leads to drug resistance, but also results in a harmful influence on the safety of the environment and plants (Lin et al. 2010). Therefore, new active antibacterial agents that possess a novel mechanism of action must be discovered and developed. It has been reported in the literatures that compounds containing the sulfone group exhibited various biological activities including antibacterial (Li et al. 2013; Li et al. 2014; Xu et al. 2012; Wu et al. 2016; Zheng et al. 2017; Su et al. 2014, 2017; Gao et al. 2017; Wang et al. 2016; Shi et al. 2015), antifungal (Liu et al. 2008; Chen et al. 2007; Xu et al. 2011a, b; Zhang et al. 2013), antiviral (Xu et al. 2013; Garuti et al. 2002), insecticidal (Fitzjohn and Robinson 1994), and herbicidal (Andrew et al. 2006) activiti
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