Page 163 - 《精细化工》2020年第9期

第 37 卷第 9 期 精 细 化 工 Vol.37, No.9
202 0 年 9 月 FINE CHEMICALS Sept. 2020

医药与日化原料
樟脑基咪唑盐类化合物合成及其抑菌活性

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赵雨珣 ，卞天岑 ，王芸芸 ，徐 徐 1,2 ，谷 文 1,2 ，王石发 1,2*
（1. 南京林业大学 化学工程学院，江苏 南京 210037；2. 南京林业大学 林业资源高效加工利用协同创
新中心，江苏 南京 210037）

摘要：以天然可再生资源樟脑磺酸为原料制备了 10-碘代樟脑，10-碘代樟脑再经季铵化反应、离子交换后得到
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16 个樟脑基咪唑盐。通过 HRMS、 HNMR、 CNMR 和 FNMR 对目标化合物结构进行了表征，采用菌丝生长
速率法测定了它们对立枯丝核菌、层出镰刀菌和灰葡萄球菌的抑制率。结果表明，目标化合物对 3 种真菌均具
有一定的抑制作用，部分目标化合物对灰葡萄球菌的抑制效果显著，3-(7,7-二甲基-2-氧代双环[2.2.1]庚-1-基)甲
基-1-(2,4,6-三甲基)苯基-咪唑-3-鎓双三氟甲磺酰亚胺盐（Ⅲd）、1-(4-氯苯基)-3-(7,7-二甲基-2-氧代双环[2.2.1]
庚-1-基)甲基-咪唑-3-鎓碘盐（Ⅴa）抑制率可达 100%，效果优于阳性药百菌清；化合物Ⅲd、Ⅳa〔1-(2,6-二异
丙基)苯基-3-(7,7-二甲基-2-氧代双环[2.2.1]庚-1-基)甲基-咪唑-3-鎓碘盐〕对层出镰刀菌有较好的抑制活性，抑制
率分别可达为 66.2%、70.4%，效果与阳性药百菌清相近；目标化合物对立枯丝核菌的抑制效果整体不及百菌清。
关键词：樟脑磺酸；咪唑盐；合成；抑菌活性
中图分类号：TQ630 文献标识码：A 文章编号：1003-5214 (2020) 09-1877-06

Synthesis and antifungal activity of camphor derived imidazolium salts

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ZHAO Yuxun , BIAN Tiancen , WANG Yunyun , XU Xu , GU Wen , WANG Shifa 1,2*
（1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China; 2. Co-Innovation
Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037,
Jiangsu, China）
Abstract: 1-Iodomethyl-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one was synthesized with recyclable
camphorsulfonic acid as raw materials and used to design and synthesize sixteen camphor derived
imidazolium salts by quaternization and metathesis reaction. These target compounds were characterized by
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HRMS, HNMR, CNMR and FNMR. 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-trimethylphenyl)-1H-imidazol-3-ium bis(trifluoromethylsulfonyl)imide (Ⅲd) and 1-(4-chlorophenyl)-
3-(7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methyl-1H-imidazol-3-ium iodide ( Ⅴ a) had inhibition
rates of 100%, better than chlorothalonil. Compounds Ⅲd and Ⅳa [1-(2,6-diisopropylphenyl)-3-(7,7-
dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methyl-1H-imidazol-3-ium iodide] had good inhibitory activities
against Fusarium proliferatum, with inhibition rates of 66.2% and 70.4%, respectively, which were similar
to that of chlorothalonil. However, the inhibition effects of the target compounds against Rhizoctonia solani
were not as good as that of chlorothalonil.
Key words: camphorsulfonic acid; imidazolium salts; synthesis; antifungal activity

[1]
近十几年内，气候变化、环境污染等问题加速 现象 。尽管市售杀菌剂在过去取得了良好的杀菌
了病原菌对农作物的破坏，造成了严重的食品短缺 效果，但其长期及过度使用已导致明显的耐药性、

收稿日期：2020-03-27; 定用日期：2020-05-21; DOI: 10.13550/j.jxhg.20200249
基金项目：国家自然科学基金（31470592）
作者简介： 赵雨珣（1996—），女，硕士生，E-mail：805225591@qq.com。联系人：王石发（1965—），男，教授，E-mail：wangshifa65@163.com。