Synthesis and Antibacterial Activity of 1-Aryl-3-(3-((2-oxo-2H-Chromen-4-yl)oxy)phenyl)thiourea Derivatives

doi:10.11944/j.issn.1000-0518.2017.07.160427

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (7): 774-782.DOI: 10.11944/j.issn.1000-0518.2017.07.160427

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Synthesis and Antibacterial Activity of 1-Aryl-3-(3-((2-oxo-2H-Chromen-4-yl)oxy)phenyl)thiourea Derivatives

CHEN Meihang^a^*(),ZHANG Xun^a,WANG Xiaobin^b,CHEN Shixue^a,SHU Hua^a^*

^aSchool of Material and Chemistry Engineering,Tongren University,Tongren,Guizhou 554300,China
^bState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering; Key Laboratory of Green Pesticide and Agricultural Bioengineering,Ministry of Education; Certer for Rearch and Development of Fine Chemicals,Guizhou University,Guiyang 550025,China

Received:2016-10-25 Accepted:2017-01-19 Published:2017-07-04 Online:2017-07-04
Contact: CHEN Meihang,SHU Hua
Supported by:
Supported by Natural Science Fund of Guizhou Province Education(No.[2011]2080), Dr Fund of Tongren University(No.trxyDH1618)

Abstract

Abstract:

In order to develop thiourea derivatives with antibacterial activities, a series of novel 1-aryl-3-(3-((2-oxo-2H-chromen-4-yl)oxy)phenyl)thiourea derivative was synthesized from 4-hydroxycoumarin via chlorination, etherification, isothiocyanate formation and addition reactions. The structures of the title compounds were characterized by infrared spectroscopy(IR), nuclear magnetic resonance spectrocopy(NMR) and mass spectrometry(MS). The results show that title compounds exhibit excellent antibacterial activities against Xanthomonas oryzae pv. oryzae(Xoo) and Xanthomonas citri subsp. Citri(Xcc). Among of them, compounds 4k, 4l, 4m and 4n show excellent antibacterial activities against Xoo, with the EC₅₀ values 137.42, 131.05, 129.23 and 117.43 mg/L, respectively, which were better than that of the control agent thiodiazole-copper(195.24 mg/L). Compounds 4k, 4l, 4m and 4n display considerable antibacterial activities against Xcc, with the EC₅₀ values of 97.02, 94.31, 102.28 and 90.52 mg/L, respectively, which are better than that of thiodiazole-copper(120.25 mg/L).

Key words: coumarin, thiourea derivatives, synthesis, antibacterial activities

CHEN Meihang, ZHANG Xun, WANG Xiaobin, CHEN Shixue, SHU Hua. Synthesis and Antibacterial Activity of 1-Aryl-3-(3-((2-oxo-2H-Chromen-4-yl)oxy)phenyl)thiourea Derivatives[J]. Chinese Journal of Applied Chemistry, 2017, 34(7): 774-782.

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Synthesis and Antibacterial Activity of 1-Aryl-3-(3-((2-oxo-2H-Chromen-4-yl)oxy)phenyl)thiourea Derivatives

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