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1,2,3-噻二唑联-1,2,4-三唑衍生物的合成及抑菌活性 被引量:7

Synthesis and Fungicidal Activity of 1,2,3-Thiadiazole Containing 1,2,4-Triazoles
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摘要 以4-氨基-3-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-5-硫酮为原料,与醛在冰乙酸中回流制得15个新型4-取代亚氨基-3-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-5-硫酮化合物,其结构经IR、1H NMR及元素分析表征,其中,化合物5c的结构经单晶测试确证,该晶体属单斜晶系,P2(1)/c空间群,晶胞参数a=1.403 7(3)nm,b=1.570 5(3)nm,c=0.6864(14)nm,β=102.06(3)°,V=1.4798(5)nm3,Z=4,F(000)=656。初步的抑菌活性测试结果表明;所有化合物对黄瓜灰霉病菌Botrytis cinerea都有较好的抑制作用,化合物5l的抑制率达87%,5c、5d和5f的抑制率在78%左右;5a对小麦赤霉病菌Gibberella zeae的抑制率为78.7%;5m对西瓜炭疽病菌Colletotrichum lagenarium的抑制率为65.6%。 Fifteen novel title compounds were synthesized from 3-(4-methyl-1,2,3-thiadiazolyl)-4-amino-1,2,4-triazolo-5-thione with substituted benzaldehyde in acetic acid under refluxing.The structures of the compounds were confirmed by elemental analysis,IR and ^1H NMR.The single crystal of compound 5c was cultured and determined by X-ray single-crystal diffraction as of a monoclinic system,space group P2(1)/c with cell parameters a=1.403 7(3) nm,b=1.570 5(3) nm,c=0.686 4(4) nm,β= 102.06(3)°,V=1.479 8(9) nm^3,Z=4,F(000)=656.Bioassaywas conducted by fungi growth inhibition method using 10 commonly used fungi which represented most disease occurring in China,the results showed that,all the title compounds had satisfactory fungicidal activity against Botrytis cinerea,the growth inhibition rate of compound 5l against Botrytis cinerea was up to 87%,for compound 5c,5d and 5f were more than 78%,compound 5a exhibited fungicidal activity against Gibberella zeae with growth inhibition of 78.7%,the growth inhibition rate of compound 5m against Colletotrichum lagenarium was 65.6%.
出处 《农药学学报》 CAS CSCD 北大核心 2009年第1期19-24,共6页 Chinese Journal of Pesticide Science
基金 国家自然科学基金(20672062,20872071) 国家自然科学基金国际合作项目(No.29) 天津市自然科学基金(07JCYBJC01200) 天津市科技支撑计划国际科技合作项目(07ZCGHHZ01400)资助
关键词 1 2 3-噻二唑 1 2 4-三唑 合成 杀菌活性 单晶结构 1 2 3-thiadiazole 1 2 3-triazole synthesis fungicide activity single crystal structure
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参考文献12

  • 1JUNG P, GODFREY C R A, LUTZ W, et al. Bisamides as Pesticides: WO 2008074427 [ P]. 2008-06-26.
  • 2TENG X, KEYS H, JEEVANANDAM A, et al. Structureactivity Relationship Study of [ 1,2,3 ] thiadiazolyl Necroptosis Inhibitors [J]. Bioorg Med Chem Lett,2007,17 (24) : 6836-6840.
  • 3MATHEW V, KESHAVAYYA J, VAIDYA V P. Heterocyclic System Containing Bridgehead Nitrogen Atom: Synthesis and Pharmacological Activities of Some Substituted 1,2,4-Triazolo [ 3,4-b ] -1,3,4-thiadiazoles [ J ]. Eur J Med Chem, 2006,41 : 1048-1058.
  • 4YASUDA M, NAKASHITA H, YOSHIDA S. Tiadinil : a Novel Class of Activator of Systemic Acquired Resistance Induces Defense Gene Expression and Disease Resistance in Tobacco [ J]. J Pestic Sci,2004,29 : 46-49.
  • 5TSUBATA K, SANPEI O, TAJIMA S, et al. Preparation of N- ( 3-Chloro-4-methylphenyl )-4-methyl-1, 2, 3-thiadiazolyl-5- carboxamide as Plant Disease Controlling Agent:WO 9923084 [ a]. 1999-05-14.
  • 6MOSTAFA Y A H, HUSSEIN M A, RADWAN A A, et al. Synthesis and Anfimicrobial Activity of Certain New 1,2,4- Triazolo [ 1 ,5-a] pyrimidine Derivatives [ J]. Arch Pharmacal Res,2008,31 (3) : 279-293.
  • 7YE X X, CHEN Z F, ZHANG A J, et al. Synthesis and Biological Evaluation of Some Novel Schiff's Bases from 1,2,4-Triazole[J]. Molecules,2007,12(6) : 1202-1209.
  • 8DUBEY P K, BABU B. Synthesis of Some 2-Heteryl-substituted Indoles [J]. Indian J Heterocycl Chem,2007,16(4) : 357-360.
  • 9JALILIAN A R, SATTARI S, BINESHMARVASTI M, et al. Synthesis and in vitro Antifungal and Cytotoxicity Evaluation of Thiazolo-4H-1,2,4-triazoles and 1,2,3-Thiadiazolo-4H-1,2,4- triazoles[J]. Arch Pharm Pharm Med Chem,2000 , 333 : 347-354.
  • 10吴太兴,李仲杰.4-氨基-5-烃基-2,4-二氢-3H-1,2,4-三唑-3-硫酮席夫碱的简便合成[J].高等学校化学学报,1998,19(10):1617-1619. 被引量:20

二级参考文献12

  • 1徐东成,杨骏,周健民,张玉霞,花文廷.2,5-二取代1,3,4-噁二唑的合成及其电子轰击质谱[J].化学通报,1996(10):61-64. 被引量:6
  • 2吴太兴,硕士学位论文,1996年
  • 3刘瑞蓝,陕西化工,1988年,1期,1页
  • 4李仲杰,化学通报,1983年,7期,13页
  • 5刘方明,有机化学,1998年,18卷,328页
  • 6Zhang Z Y,药学学报,1991年,26卷,11期,809页
  • 7Feng X M,有机化学,1990年,20卷,62页
  • 8Zhang Z Y,有机化学,1989年,9卷,150页
  • 9刘方明,化学学报,1988年,56卷,618页
  • 10Gao Z H,有机化学,1988年,8卷,180页

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