, Volume 75, Issue 15–16, pp 847–855 | Cite as

Separation of para- and meta-Imazamethabenz-methyl Enantiomers by Direct Chiral HPLC Using a Protein Chiral Selector

  • Javier Zurita-Pérez
  • María Jesús Santos-DelgadoEmail author
  • Esther Crespo-Corral
  • Luis María Polo-Díez
  • Alfonso Aguilar-Gallardo


A high performance liquid chromatography direct chiral method for the determination of p- and m-imazamethabenz-methyl (IMBM) enantiomers is described. The four isomers were separated using a protein chiral AGP™ column. Elution order was established by circular dichroism. Factorial design was employed for mobile phase optimization using a small number of experiments. The best experimental conditions were ACN/NH4Ac-HAc 60 mM (3/97) at a flow rate of 0.9 mL min−1 in isocratic mode, detection at 247 nm wavelength and 24 °C temperature. Resolution up to 1.3 was obtained for the separation of the 4 IMBM enantiomers. The proposed method is useful to determine the p/m IMBM ratios and their respective enantiomers in samples containing the aforementioned herbicide. The p/m IMBM ratio was higher in the standard than in the sample. LOD values were between 0.15 and 0.43 mg L−1 and recoveries were higher than 93 %.


Column liquid chromatography IMBM enantiomers Protein chiral selector Formulation analysis p/m Imazamethabenz-methyl ratio 



The authors thank Dirección General de Universidades e Investigación, Ministerio de Educación y Ciencia de Madrid for supporting Project CTQ2007-66971/BQU.


  1. 1.
    Jarman JL, Jones WJ, Howell LA, Garrison AW (2005) J Agric Food Chem 53:6175–6182CrossRefGoogle Scholar
  2. 2.
    Ye J, Wu J, Liu W (2009) Trends Anal Chem 28:1148–1163CrossRefGoogle Scholar
  3. 3.
    Ye J, Zhao M, Liu J, Liu W (2010) Environ Pollut 158:2371–2383CrossRefGoogle Scholar
  4. 4.
    Zhou Q, Liu W, Zhang Y, Liu kk (2007) Pestic Biochem Physiol 89:89–96CrossRefGoogle Scholar
  5. 5.
    Ladner DW (2006) Pestic Sci 29:317–333CrossRefGoogle Scholar
  6. 6.
    Lao W, Gan J (2006) J Chromatogr A 1117:184–193CrossRefGoogle Scholar
  7. 7.
    Kumar VP, Ross BL, Damian S (1997) J Chromatogr A 790:225–234CrossRefGoogle Scholar
  8. 8.
    Atienza J, Jiménez JJ, Herguedas A, Bernal JL (1996) J Chromatogr A 721:113–121CrossRefGoogle Scholar
  9. 9.
    Chin TE, Wong RB, Pont JL, Karu AE (2002) J Agric Food Chem 50:3380–3389CrossRefGoogle Scholar
  10. 10.
    Brigante M, Emmelin C, Ferronato C, Greca M, Previtera L, Paisse JO, Chovelon JM (2007) Chemosphere 68:464–471CrossRefGoogle Scholar
  11. 11.
    Nandula VK, Messersmith CG (2000) Pestic Biochem Physiol 68:148–155CrossRefGoogle Scholar
  12. 12.
    Lämmerhofer M (2010) J Chromatogr A 1217:814–856CrossRefGoogle Scholar
  13. 13.
    Hühnerfuss H, Raza Shah M (2009) J Chromatogr A 1216:481–502CrossRefGoogle Scholar
  14. 14.
    Ilisz I, Berkecz R, Péter A (2009) J Chromatogr A 1216:1845–1860CrossRefGoogle Scholar
  15. 15.
    Ward TJ, Hamburg DM (2004) Anal Chem 76:4635–4644CrossRefGoogle Scholar
  16. 16.
    Millot MC (2003) J Chromatogr B 797:131–159CrossRefGoogle Scholar
  17. 17.
    Haginaka J (2008) J Chromatogr B 875:12–19CrossRefGoogle Scholar
  18. 18.
    Guillén-Casla V, Pérez-Arribas LV, León-González ME, Polo-Díez LM (2008) J Agr Food Chem 56:2303–2309CrossRefGoogle Scholar
  19. 19.
    Lao W, Gan J (2006) J Chromatogr A 1131:74–84CrossRefGoogle Scholar
  20. 20.
    Lin KD, Xu C, Zhou SS, Liu WP, Gan J (2007) Chirality 19:171–178CrossRefGoogle Scholar
  21. 21.
    Haginaka J (2001) J Chromatogr A 906:253–273CrossRefGoogle Scholar
  22. 22.
    Rosés M (2004) J Chromatogr A 1037:283–298CrossRefGoogle Scholar
  23. 23.
    Carlson R (2005) Design and optimization in organic synthesis. Elsevier, The NetherlandGoogle Scholar
  24. 24.
    Hofstetter H, Hofstetter O, Schurig V (1997) J Chromatogr A 764:35–41CrossRefGoogle Scholar
  25. 25.
    Jin L, Gao W, Li L, Ye J, Lin C, Liu W (2011) Enantioseparation and enantioselective analysis of chiral herbicides. In: Herbicides, Theory and Applications. InTech.

Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Javier Zurita-Pérez
    • 1
  • María Jesús Santos-Delgado
    • 1
    Email author
  • Esther Crespo-Corral
    • 1
  • Luis María Polo-Díez
    • 1
  • Alfonso Aguilar-Gallardo
    • 2
  1. 1.Department of Analytical Chemistry, Faculty of ChemistryComplutense University of MadridMadridSpain
  2. 2.Department of Analytical Chemistry, Faculty of SciencesUniversity of MalagaMalagaSpain

Personalised recommendations