2-(4-甲氧基苯基)咪唑并[4,5-f]1,10-菲罗啉的合成、晶体及分子结构的测定及除草活性

doi:10.3724/SP.J.1095.2014.30177

摘要/Abstract

摘要： 合成了2-(4-甲氧基苯基)咪唑并[4,5-f]1,10-菲罗啉，采用傅里叶红外光谱、元素分析和X射线单晶衍射表征了化合物的晶体和分子结构。结果表明，目标化合物与相邻2个分子沿晶体c-轴形成2个N—H…N氢键，化合物沿晶体a-轴存在2种π-π堆积作用，这2种作用使目标化合物形成二维的超分子结构。采用琼脂混药法测定了2-(4-甲氧基苯基)咪唑并[4,5-f]1,10-菲罗啉的除草活性，结果证明目标化合物可以选择性的抑制稗草和夏至草的生长，同时促进生菜的生长。

关键词: 合成, 晶体结构, 除草活性, 选择性, 植物生长调节

Abstract: 2-(4-Methoxyphenyl)imidazole[4,5-f]1,10-phenanthroline was synthesized and characterized by FT-IR, elemental analysis and single crystal X-ray diffraction. The structure analysis revealed that each molecule formed two N—H…N hydrogen bonds with two adjacent molecules. Two types of π-π stacking modes were also observed in the title compound. N—H…N hydrogen bonds and π-π stacking interactions extend along the crystallographic c-axis and a-axis, respectively, which allows the title compound to assemble into a novel two-dimensional supramolecular architecture. The herbicidal activity of the title compound on Echinochloa crusgalli(L.) Beauv., Lagopsis supine and Lactuca sativa were carried out by the method of grinded plant tissue powder mixed with agar(PPA). The results show that the growth of Echinochloa crusgalli(L.) Beauv. and Lagopsis supine is inhibited while the growth of Lactuca sativa is promoted by the title compound.

Key words: synthesis, crystal structure, herbicidal activity, selectivity, plant growth regulator

中图分类号:

O626.3

苏范胜, 孙云明, 罗小勇, 董风英, 杨青. 2-(4-甲氧基苯基)咪唑并[4,5-f]1,10-菲罗啉的合成、晶体及分子结构的测定及除草活性[J]. 应用化学, DOI: 10.3724/SP.J.1095.2014.30177.

SU Fansheng1, SUN Yunming1, LUO Xiaoyong2, DONG Fengying1*, YANG Qing1. Synthesis, Crystal and Molecular Structures and Herbicidal Activity of 2-(4-Methoxyphenyl)imidazole [4,5-f] 1,10-phenanthroline[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30177.

参考文献

[1] Natsume B,Hikido M,Kawaguchi S. Phthalimides and Herbicide Containing the Same as Active Component:EP,1097923[P],2001-09-05.

[2] Khabnadideh S,Rezaei Z,Khalafi-Nezhad A,et al. Synthesis of N-Alkylated Derivatives of Imidazole as Antibacterial Agents[J]. Bioorg Med Chem Lett,2003,13(17):2863-2865.

[3] Khalafi-Nezhad A,Soltani Rad M N,Mohabatkar H,et al. Design, Synthesis, Antibacterial and QSAR Studies of Benzimidazole and Imidazole Chloroaryloxyalkyl Derivatives[J]. Bioorg Med Chem,2005,13(6):1931-1938.

[4] Mizerska U,Fortuniak W,Chojnowski J,et al. Polysiloxane Cationic Biocides with Imidazolium Salt(ImS) Groups, Synthesis and Antibacterial Properties[J]. Eur Polym J,2009,45(3):779-787.

[5] Lange J H M,van Stuivenberg H H,Coolen H K A C,et al. Bioisosteric Replacements of the Pyrazole Moiety of Rimonabant:Synthesis, Biological Properties, and Molecular Modeling Investigations of Thiazoles, Triazoles, and Imidazoles as Potent and Selective CB1 Cannabinoid Receptor Antagonists[J]. J Med Chem,2004,48(6):1823-1838.

[6] Seo H J,Park E J,Kim M J,et al. Design and Synthesis of Novel Arylpiperazine Derivatives Containing the Imidazole Core Targeting 5-HT2A Receptor and 5-HT Transporter[J]. J Med Chem,2011,54(18):6305-6318.

[7] Tseng S L,Hung M S,Chang C P,et al. Bioisosteric Replacement of the Pyrazole 5-Aryl Moiety of N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide(SR141716A). A Novel Series of Alkynylthiophenes as Potent and Selective Cannabinoid-1 Receptor Antagonists[J]. J Med Chem,2008,51(17):5397-5412.

[8] Lindell S D,Earnshaw C G,Wright B J,et al. Synthesis of Inhibitors of Imidazole Glycerol Phosphate Dehydratase[J]. Bioorg Med Chem Lett,1996,6(5):547-552.

[9] Taylor E C,Zhou P,Tice C M,et al. Synthesis of 2-(2,6-Dichloro-4-pyridyl)-3-propargyl-5-ethyl-6-methyl-4(3H)-pyrimidinone, a Promising New Herbicide[J]. Tetrahedron Lett,1997,38(25):4339-4342.

[10] YANG Qing,YIN Wenhua,SUN Yunming,et al. Synthesis and Herbicidal Activity of 1,10-Phenanthroline-5,6-dione[J]. Shandong Agric Sci,2012,44(8):89-91(in Chinese).

杨青,尹文华,孙云明,等. 1,10-菲咯啉-5,6-二酮的制备与除草活性研究[J]. 山东农业科学,2012,44(8):89-91.

[11] XIONG Xianwen,LIU Xianghong,HAN Lubin,et al. The Synthesis of 2-Substituted-1H-imidazo[4,5-f][1,10]phenanthroline[J]. Guangzhou Chem Ind,2013,41(9):73-75(in Chinese).

熊贤文,刘祥洪,韩璐斌,等. 2-取代-1H-咪唑并[4,5-f][1,1 0]菲咯啉[J]. 广州化工,2013,41(9):73-75.

[12] Luo X Y,Matsumoto H. Susceptibility of a Broad-leaved Weed, Acanthospermum Hispidum,to the Grass Herbicide Fluazifop-butyl[J]. Weed Biol Manage,2002,2(2):98-103.

[13] Yamada M,Tanaka Y,Yoshimoto Y,et al. Synthesis and Properties of Diamino-substituted Dipyrido [3,2-a:2′,3′-c]phenazine[J]. Bull Chem Soc Jpn,1992,65(4):1006-1011.

[14] ZHANG Zhibin,YAN Wenpeng,FAN Meigong. An Efficient Synthesis Method for 1,10-Phenanthroline-5,6-dione and Its Monooxime[J]. Chinese J Appl Chem,2008,22(1):103-104(in Chinese).

张智斌,闫文鹏,樊美公. 一种1,10-菲啰啉-5,6-二酮及其单肟的高效合成方法[J]. 应用化学,2008,22(1):103-104.

[15] Liu D M,Li X Y,Wang X C,et al. 2-Phenyl-1H-1,3,7,8-tetraazacyclopenta Phenanthrene[J]. Acta Crystallogr E,2009,65(6):o1308.

[16] Lin H W,Zhu W X. Crystal Structure of Adduct 2-Phenyl-imidazo[4,5-/]1,10-phenanthroline methanol[J]. Chinese J Chem,2003,21(8):1054-1058.

[17] Liu B,Zhou S,Li X M,et al. A New Chain-like Copper(Ⅱ) Polymer:[Cu(MOPIP)(BDC)]n·0.5n(H2O)[J]. Chinese J Struct Chem,2008,27(10):1195-1198.

[18] Dong F Y,Li Y T,Wu Z Y,et al. Solvothermal Synthesis, Crystal Structure and DNA Binding Studies of a 3D Supramolecular Complex {[Cu(phen)CN][Cu(phen)][Cu(CN)2]}n Assembled by Double Curvy Chains[J]. J Inorg Organomet Polym,2008,18(3):398-406.

[19] Sun Y M,Dong F Y,Wang D Q,et al. Synthesis, Supramolecular Architecture and DNA Binding Studies of a Novel Heterotrinuclear FeⅢ/CoⅡ/FeⅢ Complex:[Co(phen)2][Fe(phen)(CN)4]2·4H2O (phen=1,10-phenanthroline)[J]. J Inorg Organomet Polym,2010,20(1):168-176.

[20] Dou J M,Gao X K,Dong F Y,et al. One- or Two-dimensional 2,3-Naphtho Crown Ether Complexes [Na(N15C5)]2[M(SCN)4] and [K(N18C6)]2[M(SCN)4] (M=Pd,Pt) Constructed by π-π Stacking Interactions[J]. Dalton Trans,2004,33(18):2918-2922.

[21] Sun Y M,Dong F Y,Wang D Q,et al. Crystal Structure, Supramolecular Self-assembly and Interaction with DNA of a Mixed Ligand Manganese(Ⅱ) Complex[J]. J Brazil Chem Soc,2011,22(6):1089-1095.