Synthesis and fungicidal activity of camphoric acid-based benzenesulfonamide compounds

被引：0

作者：

Ma, Xian-Li ^{[1
,2
]}

Min, Fang-Qian ^{[1
]}

Duan, Wen-Gui ^{[1
]}

Li, Fang-Yao ^{[1
,2
]}

Liu, Lu-Zhi ^{[1
]}

Cen, Bo ^{[1
]}

Lei, Fu-Hou ^{[3
]}

机构：

[1] College of Chemistry and Chemical Engineering, Guangxi University, Nanning

[2] College of Pharmacy, Guilin Medical University, Guilin

[3] Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning

来源：

Chemistry and Industry of Forest Products | 2015年 / 35卷 / 01期

关键词：

Camphoric acid; Fungicidal activity; Sulfonamide; Synthesis;

D O I：

10.3969/j.issn.0253-2417.2015.01.005

中图分类号：

学科分类号：

摘要：

Camphoric anhydride was prepared via dehydration reaction using camphoric acid as starting material. Then, N-aryl sulfonyl ethyenediamines were synthesized by the reaction of ethylenediamine with substituted benzenesulfonyl chlorides, followed by the reaction of camphoric anhydride with N-aryl sulfonyl ethyenediamines to obtain eleven novel camphoric acid-based benzenesulfonamide compounds: camphoric acid-based benzenesulfonamide(4a), camphoric acid-based p-methyl-benzenesulfonamide(4b), camphoric acid-based m-methyl-benzenesulfonamide(4c), camphoric acid-based p-methoxy-benzenesulfonamide(4d), camphoric acid-based m-methoxy-benzenesulfonamide(4e), camphoric acid-based p-fluoro-benzenesulfonamide(4f), camphoric acid-based o-fluoro-benzenesulfonamide(4g), camphoric acid-based p-chloro-benzenesulfonamide(4h), camphoric acid-based m-chloro-benzenesulfonamide(4i), camphoric acid-based p-bromo-benzenesulfonamide(4j), and camphoric acid-based m-bromo-benzenesulfonamide(4k). The synthetic conditions were investigated preliminarily. The suitable synthetic conditions for the target compounds were as follows: anhydrous ethanol as solvent, reaction temperature 80℃, n(camphoric anhydride) ∶n(N-aryl sulfonyl ethyenediamine) 1 ∶1.2. The target compounds were characterized by FT-IR, 1H NMR, 13C NMR and ESI-MS, respectively. The preliminary bioassay showed that most of the title compounds exhibited certain fungicidal activity at the concentration of 50 mg/L, in which compounds 4a and 4e had inhibition rate of 94.8% against Physalospora piricola, and compound 4h had inhibition rate of 86.9% against Alternaria solani. ©, 2015, Editorial Board of Chemistry and Industry of Forest Products. All right reserved.

引用

页码：30 / 38

页数：8

共 21 条

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