含嘧啶取代1,3,4-噁二唑(噻二唑)硫醚化合物的合成及抗菌活性研究
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摘要
以2-甲基-4-氨基-5-氰基嘧啶为原料,通过水解、酯化、肼解、环化和醚化等步骤,合成了12个含1,3,4-噁二唑(噻二唑)取代嘧啶化合物。通过1H NMR、13C NMR、MS和元素分析进行结构确证。初步抑菌活性测试标明,化合物6f和6f'在50μg/m L时对油菜菌核病菌(S. sclerotiorum)、马铃薯晚疫病菌(P.infestans)、水稻纹枯病(T. cucumeris)、小麦赤霉病菌(G. zeae)具有中等抑制率,其活性与对照药剂醚菌酯相当。
Based on 4-amino-2-methylpyrimidine-5-carbonitrile as raw material, twelve 2-methyl-5-( 5-substitutional-1,3,4-oxadiazol/thiadiazole-3-yl) pyrimidin-4-amine compounds were synthesized through five step reactions including hydrolysis,esterification,hydrazidation,cyclization and thioetherification. The structures of titled compounds were characterized by1 H NMR,13 C NMR,MS and elemental analysis. Preliminary bioassay results showed that compounds 6 f and 6 f' have moderate inhibitory activities against S. sclerotiorum,P. infestans,T.cucumeris and G. zeae at the concerntration of 50 μg/m L,which are comparable to that of Azoxystrobin.
Based on 4-amino-2-methylpyrimidine-5-carbonitrile as raw material, twelve 2-methyl-5-( 5-substitutional-1,3,4-oxadiazol/thiadiazole-3-yl) pyrimidin-4-amine compounds were synthesized through five step reactions including hydrolysis,esterification,hydrazidation,cyclization and thioetherification. The structures of titled compounds were characterized by1 H NMR,13 C NMR,MS and elemental analysis. Preliminary bioassay results showed that compounds 6 f and 6 f' have moderate inhibitory activities against S. sclerotiorum,P. infestans,T.cucumeris and G. zeae at the concerntration of 50 μg/m L,which are comparable to that of Azoxystrobin.
引文
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[6]陈学文,甘秀海,陈吉祥.有机化学,2017,9:2343~2351.
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[8] W M Xu,S Yang,P Bhadury et al. Pestic. Biochem. Phys.,2011,101:6~15.
[9] Z B Yang,D Y Hu,S Zeng et al. Bioorg. Med. Chem. Lett.,2016,26:1161~1164.
[10] X H Liu,Q Wang,Z H Sun et al. Pest Manag. Sci.,2017,73:953~959.
[11] Q Chen,X L Zhu,L L Jiang et al. Eur. J. Med. Chem.,2008,43:595~603.
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[15] S Tang,Z G Peng,X Zhang et al. Chin. Chem. Lett.,2016,27:1052~1057.
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[18] S C Karad,B B Purohit,R P Thummar et al. Bioorg. Med.Chem. Lett.,2017,126:894~909.
[19]吴文能,王瑞,杜斌等.化学应用与研究,2017,29:810~815.
[20] W N Wu,Q Chen,A Tai et al. Bioorg. Med. Chem. Lett.,2015,25:2243~2246.
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[23] K C Tarun,D Prem. J. Agric. Food Chem.,2006,54(6):2129~2133.