Articles

Synthesis and Herbicidal Activity of 2-Substituted-6-methyl-4-phenyl-3(2H)-pyridazinone

  • Xu Han ,
  • Zhan Mingzhe ,
  • Liu Bin ,
  • Yang Huazheng
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  • a National Pesticidal Engineering Centre (Tianjin), Nankai University, Tianjin 300071;
    b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
    c State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071;
    d Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071

Received date: 2013-10-28

  Revised date: 2013-12-16

  Online published: 2014-01-02

Supported by

Project supported by the National Natural Science Foundation of China (No. 21002054), the Research Fund for the Doctoral Programme of Higher Education (No. 20100031120016) and the Fundamental Research Funds for the Central Universities.

Abstract

A series of novel 2-substituted-6-methyl-4-phenyl-3(2H)-pyridazinone derivatives were synthesized. All target compounds were structurally confirmed by 1H NMR and elemental analysis. An X-ray crystallographic structure determination was carried out in compound 4e. Herbicidal activities were evaluated through Brassica napus and Echinochloa crusgalli (L.) Beauv tests. Bioassay results showed that most of compounds exhibited better herbicidal activities. Quantitative structure-activity relationship studies showed that when the test grass was rape, their herbicidal activity was mainly related with substituent's sterimol parameter B4 and hydrophobic parameter π; when the test grass was barnyard grass, their herbicidal activity was mainly related with the hydrophobic parameter π of the substituents at the 2-position of pyridazinone ring. Some compounds 4 showed inhibitive activity equal to 5b and 5k, but showed no bleaching activity. The action mode in plants may be different in compounds 4 and 5.

Cite this article

Xu Han , Zhan Mingzhe , Liu Bin , Yang Huazheng . Synthesis and Herbicidal Activity of 2-Substituted-6-methyl-4-phenyl-3(2H)-pyridazinone[J]. Chinese Journal of Organic Chemistry, 2014 , 34(4) : 722 -728 . DOI: 10.6023/cjoc201310045

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