Synthesis and Fungicidal Activity of α-Terpinene-maleimide-based acylhydrazone Derivatives

doi:10.6023/cjoc1111171

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (06): 1077-1083.DOI: 10.6023/cjoc1111171 Previous Articles Next Articles

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α-萜品烯马来酰亚胺基酰腙衍生物的合成及杀菌活性研究

马献力^a,b, 黄建新^a, 段文贵^a, 莫启进^a, 林桂汕^a, 黄翊^a

a 广西大学化学化工学院南宁 530004
b 桂林医学院药学院桂林 541004

收稿日期:2011-11-17 修回日期:2012-03-08 发布日期:2012-03-09
通讯作者: 段文贵 E-mail:dwg118@gxu.edu.cn
基金资助:
广西自然科学基金(No. 2010GXNSFB013016)、广西大学科研基金(No. XJZ100245)和广西大学国家大学生创新性实验计划(No. 200924)资助项目.

Synthesis and Fungicidal Activity of α-Terpinene-maleimide-based acylhydrazone Derivatives

Ma Xianli^a,b, Huang Jianxin^a, Duan Wengui^a, Mo Qijin^a, Lin Guishan^a, Huang Yi^a

a College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
b College of Pharmacy, Guilin Medical University, Guilin 541004

Received:2011-11-17 Revised:2012-03-08 Published:2012-03-09
Supported by:
Project supported by the Natural Science Foundation of Guangxi Province (No. 2010GXNSFB013016), the Scientific Research Foundation of Guangxi University (No. XJZ100245) and the National Innovation Plan for Undergraduates in Guangxi University (No. 200924).

In this paper, α-pinene was converted into α-terpinene by Wagner-Meerwein rearrangement under catalysis of protonic acid, followed by Diels-Alder cycloaddtion reaction of α-terpinene with maleic anhydride to obtain α-terpinene-maleic anhydride adduct 3. Then, N-amino-α-terpinene -maleimide 4 was prepared by the reaction of compound 3 with hydrazine hydrate. Seventeen novel α-terpinene-maleimidebased acylhydrazones 5a～5q were synthesized by the reaction of compound 4 with substituted phenyl aldehydes under catalysis of glacial acetic acid. The synthetic conditions were investigated preliminarily. The target compounds were analyzed and characterized by means of elemental analysis, ¹H NMR, ¹³C NMR, LC-MS, and FT-IR. The preliminary bioassay showed that most of the title compounds exhibited a certain fungicidal activity, in which compound 5n had inhibition rates of 91%, 83.3%, and 76.7% against Physalospora piricola, Cercospora rachidicola, and Alternaria solani, respectively, at the concentration of 50 mg/L.

Key words: α-pinene, N-amino-α-terpinene-maleimide, α-terpinene-maleimide-based acylhydrazone, synthesis, fungicidal activity

Cite this article

Ma Xianli, Huang Jianxin, Duan Wengui, Mo Qijin, Lin Guishan, Huang Yi. Synthesis and Fungicidal Activity of α-Terpinene-maleimide-based acylhydrazone Derivatives[J]. Chin. J. Org. Chem., 2012, 32(06): 1077-1083.

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α-萜品烯马来酰亚胺基酰腙衍生物的合成及杀菌活性研究

Synthesis and Fungicidal Activity of α-Terpinene-maleimide-based acylhydrazone Derivatives

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