新型含吡唑环的N-甲氧基氨基甲酸甲酯类化合物的设计、合成及生物活性

高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (7): 1348.

新型含吡唑环的N-甲氧基氨基甲酸甲酯类化合物的设计、合成及生物活性

李淼^1,2, 张金波^2,3, 杨吉春², 李志念², 刘长令², 李正名¹

1. 南开大学元素有机化学国家重点实验室, 元素有机化学研究所, 天津 300071;
2. 沈阳化工研究院新药合成室, 沈阳 110021;
3. 沈阳化工学院化学系, 沈阳 110142

收稿日期:2008-11-13 出版日期:2009-07-10 发布日期:2009-07-10
通讯作者: 李正名, 男, 教授, 博士生导师, 中国工程院院士, 主要从事有机化学和农药化学领域的研究. E-mail: nkzml@finechembio.cn
基金资助:
国家“十一五”科技支撑项目(批准号： 2006BAE01A01-2)资助.

Design, Synthesis and Bioactivity of New N-Methoxycarbamate Containing Pyrazole

LI Miao^1,2, ZHANG Jin-Bo^2,3, YANG Ji-Chun², LI Zhi-Nian², LIU Chang-Ling², LI Zheng-Ming^1*

1. State Key Laboratory of Elemento-organic Chemistry, Research Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China;
2. Agrochemical Discovery Department, Shenyang Research Institute of Chemical Industry, Shenyang 110021, China;
3. College of Applied Chemistry, Shenyang Institute of Chemical Technology, Shenyang 110142, China

Received:2008-11-13 Online:2009-07-10 Published:2009-07-10
Contact: LI Zheng-Ming. E-mail: nkzml@finechembio.cn
Supported by:
国家“十一五”科技支撑项目(批准号： 2006BAE01A01-2)资助.

摘要/Abstract

摘要：

以苯(吡啶)乙/丙酮类化合物为原料, 经酯化、环化和缩合三步制得新型含吡唑环的N-甲氧基氨基甲酸甲酯类化合物3a~3r, 化合物及其中间体的化学结构经红外光谱、核磁共振谱及元素分析确认. 生物活性结果表明, 化合物3在400 mg/L下分别对水稻稻瘟病、黄瓜霜霉病和小麦白粉病具有很好的防治效果. 对水稻稻瘟病, R₁为甲基或甲氧基取代的苯基时活性最好; 对于黄瓜霜霉病和小麦白粉病, R₁为苯基或甲基取代苯基的化合物杀菌活性优于其它化合物, R₂为甲基的化合物杀菌活性优于R₂为氢的化合物.

关键词: 吡唑; N-甲氧基氨基甲酸甲酯类化合物; 生物活性; 杀菌活性

Abstract:

Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with high pesticidal activity, a series of new N-methoxycarbamate derivatives containing substituted pyrazoles 3a—3r were synthesized from substituted aryl alkyl ketones as starting material by esterification, cyclization and condensation. The structures of substituted pyrazole derivatives were confirmed by ¹H NMR, IR and elemental analysis. Preliminary biological evaluation show that compounds 3 have good fungicidal activity against P. oryzae, P. cubensis and E. graminis at 400 mg/L. The compounds with R₁=methyl or methoxy substituted phenyl have best activities against P. oryzae. The compounds with R₁=phenyl or methyl substituted phenyl have higher activities against P. cubensis and E. graminis than the others and the compounds with R₂=methyl have higher activities against fungi than that with hydrogen.

Key words: Pyrazole; N-Methoxycarbamate containing pyrazole; Biological evaluation; Fungicidal activity

TrendMD:

李淼, 张金波, 杨吉春, 李志念, 刘长令, 李正名. 新型含吡唑环的N-甲氧基氨基甲酸甲酯类化合物的设计、合成及生物活性. 高等学校化学学报, 2009, 30(7): 1348.

LI Miao, ZHANG Jin-Bo, YANG Ji-Chun, LI Zhi-Nian, LIU Chang-Ling, LI Zheng-Ming. Design, Synthesis and Bioactivity of New N-Methoxycarbamate Containing Pyrazole. Chem. J. Chinese Universities, 2009, 30(7): 1348.

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