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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1836-1840. 上一篇    下一篇

研究简报

1-芳基-4-吡唑-5-酰基氨基脲类化合物的合成及杀菌活性

谭成侠*,a ; 潘丽艳a ; 丁成荣a ; 来虎钦a ;
翁建全a; 周 瑛a ; 欧晓明b
  

  1. (a浙江工业大学化学工程与材料学院 杭州 310032)
    (b国家南方农药创制中心湖南基地生测部 长沙 410007)
  • 收稿日期:2007-12-31 修回日期:2008-04-03 发布日期:2008-10-20
  • 通讯作者: 谭成侠*,

Synthesis and Fungicidal Activities of 1-[(Un)substituted phenyl]-4-(pyrazol-5-ylcarbony)semicarbazide

TAN, Cheng-Xia*,a ; PAN, Li-Yana; DING, Cheng-Rong a; LAI, Hu-Qin a;
WENG, Jian-Quana ; ZHOU, Yinga ; OU, Xiao-Mingb
  

  1. (a College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014)
    (b Bioassay Department, Hunan Branch of National Southern Pesticide Research Centre, Changsha 410007)
  • Received:2007-12-31 Revised:2008-04-03 Published:2008-10-20
  • Contact: TAN, Cheng-Xia

PDF

1043

被引次数

11

为了寻求新的吡唑先导化合物, 用4-氯-1-甲基-3-乙基-5-吡唑甲酰肼与取代苯基异氰酸酯反应得到了14个新的1-吡唑酰基-4-芳基氨基脲类化合物. 经IR, 1H NMR, MS和元素分析对化合物的结构进行了表征. 初步生物活性实验结果表明, 在500 mg/mL浓度下, 化合物1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-(2-甲基苯基)氨基脲(4g), 1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-(2,4-二甲基苯基)氨基脲(4k)对小麦白粉病菌(Blumeria graminis)的抑制率分别达到90%和80%; 在25 mg/mL浓度下, 化合物1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-苯基氨基脲(4c)对黄瓜灰霉病菌(Botrytis cinerea)的抑制率达到70.1%; 化合物1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-苯基氨基脲(4c)和1-(4-氯-3-乙基-1-甲基-1H-吡唑-5-甲酰基)-4-(2-硝基苯基)氨基脲(4d)对稻瘟病菌(Pyricularia oryzae)的抑制率均达到51.3%.

关键词: 吡唑, 氨基脲, 杀菌活性

In order to find new pyrazole leading compounds, 14 1-[(un)substituted phenyl]-4-(pyrazol- 5-ylcarbony)semicarbazide devivatives were synthesized from 4-chloro-3-ethyl-1-methyl-5-pyrazole car-bonydrazide and substituted phenylisocyanate. The structures of all the new compounds were confirmed by 1H NMR, IR, MS and elemental analysis. The preliminary bioassays indicated that, at 500 (g/mL, 1-(o-tolyl)-4-(4-chloro-3-ethyl-1-methylpyrazol-5-ylcarbonyl)semicarbazide (4g) and 1-(2,4-dimethyl- phenyl)-4-(4-chloro-3-ethyl-1-methylpyrazol-5-ylcarbonyl)semicarbazide (4k) showed inhibitory activities 90% and 80% against Blumeria graminis, respectively; and at 25 (g/mL, 4-phenyl-4-(4-chloro-3-ethyl-1- methylpyrazol-5-ylcarbonyl)semicarbazide (4c) showed inhibitory activity 70.1% against Botrytis cinerea and 1-(2-nitro-phenyl-4-(4-chloro-3-ethyl-1-methylpyrazol-5-ylcarbonyl)semicarbazide (4d) showed inhibi-tory activitiy 51.3% against Pyricularia oryzae.

Key words: semicarbazide, pyrazole, fungicidal activity