2-取代-4-芳基-2H-1,2,3-三唑类化合物的合成及杀菌活性

doi:10.11944/j.issn.1000-0518.2018.11.170421

摘要/Abstract

摘要：

1,2,3-三唑化合物具有广泛的生物活性,为了发现具有杀菌活性的新型化合物分子结构,以芳醛、硝基甲烷及叠氮化钠为起始原料,合成了11个2-取代-4-芳基-2H-1,2,3-三唑类系列化合物,目标物的收率为51%~91%。核磁共振谱、质谱和元素分析等技术手段对目标化合物的结构经进行了表征。结果表明,在25 mg/L的测试质量浓度下,大部分化合物对小麦赤霉病菌及辣椒疫霉病菌显示出初步的抑菌活性,其中,化合物3a对小麦赤霉病菌的抑制率为80.4%,化合物3b对黄瓜灰霉病菌为78.2%,化合物3b及3h对油菜菌核病菌的抑制率分别70.3%和75.9%。

关键词: 三唑, 结构表征, 杀菌活性

Abstract:

1,2,3-Triazole compounds show a wide range of biological activities. In order to find new compounds with bactericidal activity, a series of 2-substituted-4-aryl-2H-1,2,3-triazoles was synthesized from benzaldehyde or substituted benzaldehyde, nitromethane and sodium azide in 51% to 91% yields. The structures of these compounds were characterized by nuclear magnetic resonance spectroscopy(NMR), mass spectra and elemental analyses. Most of these compounds show the preliminary antibacterial activity against Gibberella zeae and Phytophythora capsici in vitro, in 25 mg/L concentration. Among them, compound 3a shows 80.4% activity of against Gibberella zeae, compound 3b shows 78.2% activity of against Botrytis cinerea, compounds 3a and 3h show 70.3%, 75.9% activities of against Sclerotonia sclerotiorum, respectively.

Key words: triazole, structure characterization, fungicidal activity

李元祥,刘益林,雷素芳,陈迪钊,薄瑞,李孙勇. 2-取代-4-芳基-2H-1,2,3-三唑类化合物的合成及杀菌活性[J]. 应用化学, 2018, 35(11): 1325-1330.

LI Yuanxiang,LIU Yilin,LEI Sufang,CHEN Dizhao,BO Rui,LI Sunyong. Synthesis and Fungicidal Activity of 2-Substituted-4-aryl-2H-1,2,3-triazole Derivatives[J]. Chinese Journal of Applied Chemistry, 2018, 35(11): 1325-1330.

参考文献

[1]	Phillips O A,Udo E E,Ali A A M,et al.Synthesis and Antibacterial Activity of 5-Substituted Oxazolidinones[J]. Bioorg Med Chem,2003,11(1):35-41.
[2]	Kim J Y,Boyer F E,Choy A L,et al. Synthesis and Structure-activity Studies of Novel Homomorpholine Oxazolidinone Antibacterial Agents[J]. Bioorg Med Chem Lett,2009,19(2):550-553.
[3]	Vatmurge N S,Hazra B G,Pore V S,et al. Synthesis and Biological Evaluation of Bile Acid Dimers Linked with 1,2,3-Triazole and Bis-β-lactam[J]. Org Biomol Chem,2008,6(20):3823-3830.
[4]	SONG Baoan,HU Deyu,ZENG Song,et al. Synthesis and Bioactivity of Phosphorodithioate Comounds Containing 1,2,4-Triazole[J]. Chinese J Org Chem,2001,21(7):524-529(in Chinese). 宋宝安,胡德禹,曾松,等. 含1,2,4-三唑基二硫代磷酸酯新化合物合成与生物活性研究[J]. 有机化学,2001,21(7):524-529.
[5]	Oreste L,Guiliana B,Maria F,et al. Synthesis and in vitro Antiinflammatory Activity of 4-Phenyl-1,2,3-triazole Derivatives[J]. Euro J Med Chem,1983,18(5):471-475.
[6]	Rohrig U F,Majjigapu S R,Grosdidier A,et al. Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition[J]. J Med Chem,2012,55(11):5270-5290.
[7]	Lee S M,Yoon K B,Lee H J,et al. The Discovery of 2,5-Isomers of Triazole-pyrrolopyrimidine as Selective Janus Kinase 2(JAK2) Inhibitors Versus JAK1 and JAK3[J]. Bioorg Med Chem,2016,24:5036-5046.
[8]	Deng H,Kooijman S,Nieuwendijk A M H,et al. Triazole Ureas Act as Diacylglycerol Lipase Inhibitors and Prevent Fasting-Induced Refeeding[J]. J Med Chem,2017,60:428-440.
[9]	Fan Z J,Yang Z K,Zhang H K,et al. Synthesis, Crystal Structure, and Biological Activity of 4-Methyl-1,2,3-thiadiazole-Containing 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles[J]. J Agric Food Chem,2010,58(5):2630-2636.
[10]	Liu N,Dong F S,Xu J,et al. Stereoselective Determination of Tebuconazole in Water and Zebrafish by Supercritical Fluid Chromatography Tandem Mass Spectrometry[J]. J Agric Food Chem,2015,63(28):6297-6303.
[11]	Gestel J V,Heeres J,Janssen M,et al. Synthesis and Screening of a New Group of Fungicides:1-(2-Phenyl-1,3-dioxolan-2-ylmethyl)-1,2,4-Triazoles[J]. Pestic Sci,1980,11(1):95-99.
[12]	LI Zhengming,DONG Liwen,LI Guowei,et al. Stereochemistry of New Systemic Fungicides Triadimenol and TriadimefonⅡ[J]. Chinese J Org Chem,1985,5(2):188-192(in Chinese). 李正名,董丽雯,李国炜,等. 内吸性杀菌剂三唑醇(酮)立体异构体的研究Ⅱ[J]. 有机化学,1985,5(2):188-192.
[13]	Hu Q Q,Liu Y,Deng X C,et al. Aluminium(III) Chloride-Catalyzed Three-Component Condensation of Aromatic Aldehydes, Nitroalkanes and Sodium Azide for the Synthesis of 4-Aryl-NH-1,2,3-Triazoles[J]. Adv Synth Catal,2016,358:1689-1693.
[14]	Zefirov N S,Chapovskaya N K.New Method for Synthesizing 1,2,3-Triazoles[J]. Vestn Mosk Univ,Ser 2:Khim,1969,24(5):113-114.
[15]	Zhang W S,Kuang C X,Yang Q.Palladium-Catalyzed One-Pot Synthesis of 4-Aryl-1H-1,2,3-triazoles from Anti-3-aryl-2,3-dibromopropanoic Acids and Sodium Azide[J]. Synthesis,2010,2:283-287.
[16]	Nobutaka K,Takayuki S. Diphenyl Phosphorazidate(DPPA) as a 1,3-Dipole. A Simple, Efficient Conversion of Alkyl Phenyl Ketones to 2-Phenylalkanoic Acids[J]. Chem Pharm Bull,1983,31(8):2564-2573.
[17]	Mistry S N,Jörg M,Lim H,et al. 4-Phenylpyridin-2-one Derivatives:A Novel Class of Positive Allosteric Modulator of the M1 Muscarinic Acetylcholine Receptor[J]. J Med Chem,2016,59(1):388-409.
[18]	Wang Z J,Gao Y,Hou Y L,et al. Design, Synthesis, and Fungicidal Evaluation of a Series of Novel 5-Methyl-1H-1,2,3-trizole-4-carboxyl Amide and Ester Analogues[J]. Euro J Med Chem,2014,86:87-94.
[19]	LI Yuanxiang,LEI Sufang,CHEN Dizhao,et al. Preparation of Benzene Ring Containing Halogenated Triazole Compounds as Fungicides Preparation of Benzene Ring Containing Halogenated Triazole Compounds as Fungicides:CN. Preparation of Benzene Ring Containing Halogenated Triazole Compounds as Fungicides Preparation of Benzene Ring Containing Halogenated Triazole Compounds as Fungicides:CN,201610298825.5[P].2016-05-06(in Chinese). 李元祥,雷素芳,陈迪钊,等. 一类含苯环及卤取代的三唑化合物及其制备方法和用途:中国,201610298825.5[P].2016-05-06.