| 1-芳基-3，5-二甲基吡唑-4-羧酸有机锡酯的合成、结构及杀菌活性研究 |
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| 引用本文： | 王志宏,王 贺,郭彦召,韦张文,马 琳,范志金. 1-芳基-3，5-二甲基吡唑-4-羧酸有机锡酯的合成、结构及杀菌活性研究[J]. 无机化学学报, 2012, 28(9): 1926-1934 |
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| 作者姓名： | 王志宏 王 贺 郭彦召 韦张文 马 琳 范志金 |
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| 作者单位： | 南开大学元素所,南开大学元素有机国家重点实验室,天津300071 |
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| 基金项目： | 高等学校博士点新教师基金(No.20070055043);教育部留学回国人员基金;国家自然科学基金(No.20872071)资助项目 |
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| 摘 要： | 由1-芳基-3,5-二甲基吡唑-4-羧酸与适当的有机锡反应,合成表征了一系列的1-芳基-3,5-二甲基吡唑-4-羧酸有机锡酯(1～14),并通过单晶衍射确定了1-苯基-3,5-二甲基吡唑-4-羧酸三乙基锡酯(7)的结构。该化合物与一分子水共同结晶,通过分子间O-H…O及O-H…N氢键形成二维网状结构。杀菌活性筛选表明新合成的化合物对于番茄早疫菌、花生褐斑菌、小麦赤霉菌、苹果轮纹菌及灰霉菌全部具有良好的生长抑制作用。1-苯基-3,5-二甲基吡唑-4-羧酸三乙基锡酯及1-(2-吡啶基)-3,5-二甲基吡唑-4-羧酸三乙基锡酯在50μg.mL-1浓度下的体外实验中表现出很高的生长抑制率。对于高活性的三取代锡羧酸酯进行了EC50值的测定,结果表明1-(2-吡啶基)-3,5-二甲基吡唑-4-羧酸三乙基锡酯对苹果轮纹菌的EC50值为0.06μg.mL-1,对小麦赤霉菌的EC50值为0.14μg.mL-1。
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| 关 键 词： | 有机锡羧酸酯 1-芳基-3,5-二甲基吡唑-4-羧酸 晶体结构 杀菌活性 |
Synthesis, Structure and Fungicidal Activity of Organotin 1-Aryl-3,5-dimethylpyrazole-4-carboxylates |
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| WANG Zhi-Hong,WANG He,GUO Yan-Zhao,WEI Zhang-Wen,MA Lin and FAN Zhi-Jin. Synthesis, Structure and Fungicidal Activity of Organotin 1-Aryl-3,5-dimethylpyrazole-4-carboxylates[J]. Chinese Journal of Inorganic Chemistry, 2012, 28(9): 1926-1934 |
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| Authors: | WANG Zhi-Hong WANG He GUO Yan-Zhao WEI Zhang-Wen MA Lin FAN Zhi-Jin |
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| Affiliation: | State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China,State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China,State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China,State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China,State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China and State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China |
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| Abstract: | A series of organotin 1-phenyl-3,5-dimethylpyrazole-4-carboxylates and 1-(2-pyridyl)-3,5-dimethyl-pyrazole-4-carboxylates(1 ～14) have been obtained and characterized by IR,NMR(1H,13C and 119Sn) and elemental analysis.The structure of triethyltin 1-phenyl-3,5-dimethylpyrazole-4-carboxylate 7 has been further confirmed by X-ray diffraction crystallography.This complex crystallizes with a molecule of water and forms an infinite 2D network through intermolecular O-H…O and O-H…N hydrogen bonds.Fungicide screening indicates that all complexes display good growth inhibition against Alternaria solani,Cercospora arachidicola,Gibberella zeae,Physalospora piricola and Botrytis cinerea.Moreover,high growth inhibition percentage at 50 μg.mL-1 was observed in vitro in case of triorganotin 1-phenyl-3,5-dimethylpyrazole-4-carboxylates and 1-(2-pyridyl)-3,5-dimethylpyrazole-4-carboxylates.The corresponding EC50 of these highly active triorganotin carboxylates have been detected.The value of EC50 of triethyltin 1-(2-pyridyl)-3,5-dimethylpyrazole-4-carboxylate is only 0.06 μg.mL-1 against Physalospora piricola and 0.14 μg.mL-1 against Gibberella zeae,respectively. |
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| Keywords: | organotin carboxylate 1-aryl-3,5-dimethylpyrazole-4-carboxylic acid crystal structure fungicidal activity |
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