Synthesis and antifungal activity of camphor derived imidazolium salts
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    Abstract:

    1-Iodomethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one was synthesized with recyclable camphorsulfonic acid as raw material and used to design and synthesize sixteen camphor derived imidazolium salts by quaternization and metathesis reaction. These target compounds were characterized by HRMS, 1HNMR, 13CNMR and 19FNMR. Their inhibition rates against Rhizoctonia solani, Fusarium proliferatum and Botrytis cinerea were tested by mycelial growth method. The results indicated that these compounds had certain inhibitory effects on three fungi. Some of the target compounds showed significant inhibitory effects on Botrytis cinerea, among them, 3-(7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methyl-1-(2,4,6-trimethyl)phenyl-1H-imidazol-3-ium bis(trifluoromethylsulfonyl) imide (Ⅲd) and 1-(4-bromophenyl)-3-(7,7-dimethyl-2-oxobicyclo [2.2.1]heptan-1-yl)methyl)-1H-imidazol-3-ium iodide (Ⅴa) had inhibition rates of 100%, better than chlorothalonil. Compounds Ⅲd and Ⅳa 1-(2,6-diiso-propylphenyl)-3-(7,7-dimethyl-2-oxobicyclo [2.2.1]heptan-1-yl)methyl)-1H-imidazol-3-ium iodide had good inhibitory activities against Fusarium proformi, with inhibition rates of 66.2% and 70.4%, respectively, which were samilar to that of chlorothalonil. The inhibition effects of the target compounds against Rhizoctonia solani were not as good as that of chlorothalonil.

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History
  • Received:March 27,2020
  • Revised:May 20,2020
  • Adopted:May 21,2020
  • Online: August 05,2020
  • Published:
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