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

doi:10.6023/cjoc201310045

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (4): 722-728.DOI: 10.6023/cjoc201310045 Previous Articles Next Articles

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2-取代-6-甲基-4-苯基-3(2H)-哒嗪酮类化合物的合成及除草活性研究

许寒^a,d, 战明哲^b, 刘斌^c, 杨华铮^c

a 南开大学农药国家工程研究中心天津 300071;
b 郑州大学化学与分子工程学院郑州 450001;
c 南开大学元素有机化学研究所元素有机化学国家重点实验室天津 300071;
d 天津化学化工协同创新中心天津 300071

收稿日期:2013-10-28 修回日期:2013-12-16 发布日期:2014-01-02
通讯作者: 许寒 E-mail:xuhan@nankai.eu.cn
基金资助:
国家自然科学基金（No. 21002054）、高等学校博士学科点专项科研基金（No. 20100031120016）和中央高校基本科研业务费资助项目.

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

Xu Han^a,d, Zhan Mingzhe^b, Liu Bin^c, Yang Huazheng^c

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:2013-10-28 Revised:2013-12-16 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.

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.

Key words: phenylpyridazinone, herbicidal activity, quantitative structure-activity relationship

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]. Chin. J. Org. Chem., 2014, 34(4): 722-728.

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2-取代-6-甲基-4-苯基-3(2H)-哒嗪酮类化合物的合成及除草活性研究

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

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