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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 06: 1077 - 1083

DOI: https://doi.org/10.6023/cjoc1111171

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

  • Ma Xianli ,
  • Huang Jianxin ,
  • Duan Wengui ,
  • Mo Qijin ,
  • Lin Guishan ,
  • Huang Yi
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  • a College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004
    b College of Pharmacy, Guilin Medical University, Guilin 541004

Received date: 2011-11-17

  Revised date: 2012-03-08

  Online 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).

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Abstract

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]. Chinese Journal of Organic Chemistry, 2012 , 32(06) : 1077 -1083 . DOI: 10.6023/cjoc1111171

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