Synthesis and phytotoxicity of new ionic liquids incorporating chiral cations and/or chiral anions.
The aim of this work was to synthesize chiral ionic liquids as chiral solvents for organic synthesis and to evaluate the phyto(eco)toxicity of the new products and starting N-alkylimidazoles and their potential environmental influence on soil and plants. Chiral ionic liquids containing anions such as Cl-, 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 tosylate in 62-100% yields. The chloride 7 and the nitrate 13 ionic liquids possessed a toxicity dependent on the 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 common radish (100 mg/kg). The nitrate liquid did not exhibit an inhibiting effect on the germination ability of seeds. 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).
Bałczewski
Piotr
P
Department of Heteroorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland. pbalczew@bilbo.cbmm.lodz.pl
Bachowska
Barbara
B
Białas
Tomasz
T
Biczak
Robert
R
Wieczorek
Wanda M
WM
Balińska
Agnieszka
A
D000838:Anions; D002412:Cations; D002712:Chlorides / Q000633:toxicity; D003247:Conservation of Natural Resources; D018525:Germination / Q000187:drug effects; D001467:Hordeum / Q000187:drug effects; D009566:Nitrates / Q000633:toxicity; D010944:Plants / Q000187:drug effects*; D012639:Seeds / Q000187:drug effects / Q000254:growth & development; D012996:Solutions; D012997:Solvents / Q000138:chemical synthesis* / Q000633:toxicity*
D000838:Anions; D002412:Cations; D002712:Chlorides; D009566:Nitrates; D012996:Solutions; D012997:Solvents