Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole

doi:10.3724/SP.J.1095.2014.30488

Chinese Journal of Applied Chemistry

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Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole

YANG Qingcui^1,2, SUN Xiaohong^1,3*, LIU Yuanfa⁴, CHEN Bang⁴, SHEN Shengqiang³

(1.College of Chemical Engineering,Northwest University,Xi′an 710069,China;
2.School of Science,Xi′an University of Architecture and Technology,Xi′an 710055,China;
3.Chemical Research Institute,College of Chemical Engineering,Northwest University,Xi′an 710069,China;
4.College of Chemistry and Materials Science,Northwest University,Xi′an 710069,China)

Received:2013-09-26 Revised:2013-12-31 Published:2014-07-10 Online:2014-07-10
Contact: SUN Xiao-hong

Abstract

Abstract: Nine Shiff bases 3-methyl-4-(X-substituted-benzylideneamino)-5-ethoxycarbonyl methylsulfanyl-1,2,4-triazole a～i were synthesized from 3-methyl-4-amino-5-ethoxycarbonylmethyl sulfanyl-1,2,4-triazole and substituted aromatic aldehydes. The structures of synthetic compounds were confirmed by 1H NMR, IR, MS analyses. The crystal structure of 3-methyl-4-(4-hydroxybenzylideneamino)-5-ethoxycarbonylmethylsulfanyl-1,2,4-triazole h （CCDC：910927） was determined by X-ray diffraction as:C14H16N4O3S, Mr=320.37, Orthorhombic, P2(1)2(1)2(1)/n, a=0.9220(10) nm, b=1.5823(17) nm, c=2.1667(2) nm, V=3.161(6) nm3, Z=8, F(000)=1344. The antifungal activities of the new Schiff bases against four vegetable pathogens have been tested. The EC95 values of compounds d, e and f against Gibberlla saubinetii and Fusarium oxysporium f.s.p. niveum indicate that their antifungal activities are better than that of triadimefon.

Key words: Schiff base, methyl-amino-ethoxycarbonylmethylsulfanyl-triazole, synthesis, antifungal activity

CLC Number:

O622.6

YANG Qingcui1,2, SUN Xiaohong1,3*, LIU Yuanfa4, CHEN Bang4, SHEN Shengqiang3. Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30488.

References

[1] LI Xingwei,ZHAO Bin,CAO Zhencai,et al. Synthesis and Photovoltaic Properties of Conjugated Polymers Based on 1,2,4-Triazole Derivatives[J]. Acta Chim Sin,2012,70(23):2433-2439(in Chinese).

李新炜,赵斌,曹镇财,等. 基于1,2,4-三氮唑衍生物的共轭聚合物的合成及其光伏性能[J]. 化学学报,2012,70(23):2433-2439.

[2] Kumar M S,Tamilarasan R，Sreekanth A. 4-Salicylideneamino-3-methyl-1,2,4-triazole-5-thione as a Sensor for Aniline Recognition[J]. Spectrochim Acta Part A,2011,79(2):370-375.

[3] Aslan A，Bozkurt A. Development and Characterization of Polymer Electrolyte Membranes Based on Ionical Cross-linked Poly(1-vinyl-1,2,4 triazole) and Poly(vinylphosphonic acid)[J]. J Power Sources,2009,191(2):442-447.

[4] Naik A D,Beck J，Dirtu M M,et al. Zinc Complexes with 1,2,4-Triazole Functionalized Amino Acid Derivatives:Synthesis, Structure and β-lactamase Assay[J]. Inorg Chim Acta,2011,368(1):21-28.

[5] Uzgoren-Baran A,Tel B C，Sarigol D,et al. Thiazolo[3,2-b]-1,2,4-triazole-5(6H)-one Substituted with Ibuprofen:Novel Non-steroidal Anti-inflammatory aAgents with Favorable Gastrointestinal Tolerance[J]. Eur J Med Chem,2012,57(11):398-406.

[6] ZHENG Yuguo,WEI Xue,GUO Qingqing,et al. Synthesis and Biological Activitiesof NovelBistriazolyl-3(2)-pyridazinones[J]. Chinese J Appl Chem,2011,28(9):1028-1034(in Chinese).

郑玉国,魏学,郭晴晴,等. 双三唑席夫碱哒嗪酮衍生物的合成及其生物活性[J]. 应用化学,2011,28(9):1028-1034.

[7] LIU Xiaolan,LIU Yonghong,SHI Yaocheng,et al. Application of Schiff′s Bases in Organic Synthesis[J]. Chinese J Org Chem,2002,22(7):482-488(in Chinese).

刘晓岚,刘永红,石尧成,等. 希夫碱在有机合成中的应用研究[J]. 有机化学,2002,22(7):482-488.

[8] WANG Haiwei,ZHU Wenjuan,Yu Zhiran,et al. Synthesis and Structure Characterization of Sulfur Ethers Containing 1,2,4-Triazole and 1,3,4-Oxadiazole[J]. Chinese J Org Chem,2012,32(10):1888-1893(in Chinese).

王海卫,朱文娟,于知冉,等. 含1,2,4-三唑和1,3,4-噁二唑硫醚类化合物的合成及结构表征[J]. 有机化学,2012,32(10):1888-1893.

[9] Eswaran S,Adhikari A V，Shetty N S. Synthesis and Antimicrobial Activities of Novel Quinoline Derivatives Carrying 1,2,4-Triazole Moiety[J]. Eur J Med Chem,2009,44(11):4637-4647.

[10] SUN Xiaohong,BAI Yan,LIU Yuanfa,et al. Synthesis, Structure and Biological Activities of 3-Substituted Phenoxymethyl-4-amino-1,2,4-triazol-5-thione Schiff Bases[J]. Acta Chim Sin,2010,68(8):788-792(in Chinese).

孙晓红,白燕,刘源发,等. 3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮席夫碱的合成、结构表征和生物活性研究[J]. 化学学报,2010,68(8):788-792.

[11] Isloor A M,Kalluraya B,Shetty P. Regioselective reaction: Synthesis, Characterization and Pharmacological Studies of Some New Mannich Bases Derived from 1,2,4-Triazoles[J]. Eur J Med Chem,2009,44(9):3784-3787.

[12] SUN Xiaohong,TAO Yan,LIU Yuanfa,et al. Synthesis and Biological Activities of N-(5-Alkyl-2,4-dihydro-3-thioxo-1,2,4-triazol-4-yl) Schiff Bases[J]. Chinese J Org Chem,2008,28(1):155-159(in Chinese).

孙晓红,陶燕,刘源发,等. 烷基取代三唑硫酮席夫碱的合成和生物活性研究[J]. 有机化学,2008,28(1):155-159.

[13] Eweiss N F,Bahajaj A A,Elsherbini Shetty E A. Synthesis and Antimicrobial Activity of Some 4-Amino-5-aryl-l,2,4-triazole-3-thiones and Their Derivatives[J]. J Heterocycl Chem,1986,23(1):1451-3787.

[14] Ionut V L,Vasile N B,Ionut M T,et al. New Azomethine Derivatives of 3-Substituted-4H-4-amino-5-ethoxycarbonyl-methylsulfanyl-1,2,4-triazoles as Potential Anti-inflammatory Agents[J]. Rev Chem(Bucharest),2010,61(10):937-939.

[15] YANG Qingcui,SUN Xiaohong,LIU Yuanfa,et al. Synthesis and Biological Activity of Schiff Base Derivatives of 3-Methyl-4-amino-5-ethoxycarbonyl-methylsulfanyl-1,2,4-triazole[J]. Chemistry,2013,76(8):758-761(in Chinese).

杨清翠,孙晓红,刘源发,等. 3-甲基-4-氨基-5-乙氧羰基甲硫基三唑席夫碱的合成及生物活性[J]. 化学通报,2013,76(8):758-761.

Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole

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