| 4-甲基-1,2,3-噻二唑-5-甲酸芳酯的合成及生物活性 |
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| 引用本文： | 王守信,米娜,范志金,付一峰,黄云,王唤,张正财,张聚方,宋海斌,BELSKAYAN.P.,BAKULEVV.A..4-甲基-1,2,3-噻二唑-5-甲酸芳酯的合成及生物活性[J].农药学学报,2010,12(3):255-263. |
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| 作者姓名： | 王守信 米娜 范志金 付一峰 黄云 王唤 张正财 张聚方 宋海斌 BELSKAYAN.P. BAKULEVV.A. |
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| 作者单位： | 1.农业部农药化学与应用重点开放实验室,北京 100193 |
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| 基金项目： | 农业部农药化学与应用重点开放实验室基金，国家自然科学基金，国家重点基础研究发展计划("973"计划)项目，天津市自然科学基金重点项目，农业部公益性行业专项 |
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| 摘 要： | 为了寻找高效广谱的植物激活剂候选化合物,以三乙胺为缚酸剂,通过4-甲基-1,2,3-噻二唑-5-甲酰氯与酚类化合物在二氯甲烷中于室温下反应,制得一系列共20个4-甲基-1,2,3-噻二唑-5-甲酸芳酯化合物,其中9个化合物未见文献报道,所有化合物的结构均得到了核磁共振氢谱、红外光谱、高分辨质谱的表征和确认。选择化合物 2g 培养了单晶,利用X-射线单晶衍射确证了该类化合物的空间结构。杀菌活性测定结果表明:部分化合物在50 μ g/mL下具有显著的离体杀菌活性,其中化合物 2c,2n和2o 具有广谱的杀菌活性,其EC50值在3.46~23.30 μ g/mL之间。生物活性测定结果表明,部分化合物显示了较好的抗病毒活性,大部分化合物对烟草花叶病毒(TMV)具有较好的钝化效果, 2a,2c,2d,2e,2f,2g,2l,2o 具有较好的诱导烟草抗TMV的活性。
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| 关 键 词： | 1 2 3-噻二唑 合成 生物活性 植物激活剂 |
| 收稿时间： | 2010/6/30 0:00:00 |
| 修稿时间： | 2010/8/19 0:00:00 |
Synthesis and biological activity of 4-methyl-1,2,3-thiadiazole-5-carboxylates |
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| WANG Shou-xin,MI N,FAN Zhi-jin,FU Yi-feng,HUANG Yun,WANG Huan,ZHANG Zheng-cai,ZHANG Ju-fang,SONG Hai-bin,BELSKAYA N.P. and BAKULEV V.A..Synthesis and biological activity of 4-methyl-1,2,3-thiadiazole-5-carboxylates[J].Chinese Journal of Pesticide Science,2010,12(3):255-263. |
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| Authors: | WANG Shou-xin MI N FAN Zhi-jin FU Yi-feng HUANG Yun WANG Huan ZHANG Zheng-cai ZHANG Ju-fang SONG Hai-bin BELSKAYA NP and BAKULEV VA |
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| Institution: | 1.The Key Laboratory of Pesticide Chemistry and Application,Ministry of Agriculture (MOA),Beijing 100193,China2.State Key Laboratory of Elemento Organic Chemistry,Nankai University,Tianjin 300071,China3.Department of Plant Protection,Sichuan Agricultural University,Yaan 625014,Sichuan Province,China4.The Ural Federal University Named After the First President of Russia B.N.Yeltsin, Yeltsin UrFU,620002,Ekaterinburg,Russia |
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| Abstract: | Heterocyclic compounds had various biological activities,in order to explore novel elicitors with a broad spectrum and highly systemic acquired resistance,a series of 4-methyl-1,2,3-thiadiazole-5-carboxylates were synthesized by using 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride and substituted hydroxyl aromatic compounds as reactants.These reactions were conducted in dichloromethane at room temperature and using triethylamine as acid binding agent.All synthesized compounds including 9 new structures were confirmed by 1H NMR,IR and HRMS.Crystal structure of 2g was cultured and characterized by X-ray crystal diffraction method to validate the detailed chemical structure for this kind of compounds.Bioassay indicated that some compounds possessed obvious fungicidal activity at a concentration of 50 μ g/mL.Among these compounds, 2c,2n and 2o possessed a broad spectrum of fungicidal activity and EC50 value of these compounds ranged from 3.46 to 23.30 μ g/mL.Antivirus activity screening indicated that some compounds possessed good anti-TMV activity and most compounds displayed good inactivation activity against TMV.Moreover,compounds including 2a,2c,2d,2e,2f,2g,2l and 2o exhibited good systemic acquired resistance for tobacco against TMV as compared with positive control agents. |
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| Keywords: | 1 2 3-thiadiazole synthesis bioactivity plant elicitor |
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