Synthesis and Phytotoxicity of New Ionic Liquids Incorporating Chiral Cations and/or Chiral Anions

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• 作者：Piotr Ba//pubs.acs.org/images/entities/lstrok.gif" border="0">czewski ; Barbara Bachowska ; Tomasz Bia//pubs.acs.org/images/entities/lstrok.gif" border="0">as ; Robert Bicza
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2007
• 出版时间：March 7, 2007
• 年：2007
• 卷：55
• 期：5
• 页码：1881 - 1892
• 全文大小：888K
• 年卷期：v.55,no.5(March 7, 2007)
• ISSN：1520-5118

文摘

The aim of this work was to synthesize chiral ionic liquids as chiral solvents for organic synthesisand to evaluate the phyto(eco)toxicity of the new products and starting N-alkylimidazoles and theirpotential environmental influence on soil and plants. Chiral ionic liquids containing anions such asCl^-, Br^-, TsO^-, PF₆^-, NO₃^-, CF₃SO₃^-, and (+)- and (-)-C₆H₅CH(OH)C(O)O^- were synthesized using(-)-(1R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethyl [(-)-(1R)-nopyl] halides (X = Cl, Br) and tosylatein 62-100% yields. The chloride 7 and the nitrate 13 ionic liquids possessed a toxicity dependent onthe applied concentration. The lowest concentration causing a distinct reduction in plant germination/growth was 100 mg/kg. Spring barley better tolerated the ionic liquids (200 mg/kg) than commonradish (100 mg/kg). The nitrate liquid did not exhibit an inhibiting effect on the germination ability ofseeds. The starting N-methylimidazole used in lower concentrations (1 and 10 mg/kg of soil dry weight)was not phytotoxic, in contrast to higher doses (>1000 mg/kg).