Skip to main content

Advertisement

Log in

Preparation and utilization of molecularly imprinted polymer for chlorsulfuron extraction from water, soil, and wheat plant

  • Published:
Environmental Monitoring and Assessment Aims and scope Submit manuscript

Abstract

A molecularly imprinted polymer (MIP) was prepared using chlorsulfuron (CS), a herbicide as a template molecule, methacrylic acid as a functional monomer, ethylene glycol dimethacrylate (EDMA) as a cross-linker, methanol and toluene as a porogen, and 2,2-azobisisobutyronitrile as an initiator. The binding behaviors of the template chlorsulfuron and its analog on MIP were evaluated by equilibrium adsorption experiments, which showed that the MIP particles had specific affinity for the template CS. Solid-phase extraction (SPE) with the chlorsulfuron molecularly imprinted polymer as an adsorbent was investigated. The optimum loading, washing, and eluting conditions for chlorsulfuron molecularly imprinted polymer solid-phase extraction (CS-MISPE) were established. The optimized CS-MISPE procedure was developed to enrich and clean up the chlorsulfuron residue in water, soils, and wheat plants. Concentrations of chlorsulfuron in the samples were analyzed by HPLC-UVD. The average recoveries of CS spiked standard at 0.05~0.2 mg L−1 in water were 90.2~93.3%, with the relative standard deviation (RSD) being 2.0~3.9% (n = 3). The average recoveries of 1.0 mL CS spiked standard at 0.1~0.5 mg L−1 in 10 g soil were 91.1~94.7%, with the RSD being 3.1~5.6% (n = 3). The average recoveries of 1.0 mL CS spiked standard at 0.1~0.5 mg L−1 in 5 g wheat plant were 82.3~94.3%, with the RSD being 2.9~6.8% (n = 3). Overall, our study provides a sensitive and cost-effective method for accurate determination of CS residues in water, soils, and plants.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  • Ayano, E., Kanazawa, H., Ando, M., & Nishimura, T. (2004). Determination and quantitation of sulfonylurea and urea herbicides in water samples using liquid chromatography with electrospray ionization mass spectrometric detection. Analytica Chimica Acta, 507, 211–218.

    Article  CAS  Google Scholar 

  • Baggiani, C., Anfossi, L., & Giovannoli, C. (2007). Solid phase extraction of food contaminants using molecular imprinted polymers. Analytica Chimica Acta, 591, 29–39.

    Article  CAS  Google Scholar 

  • Baggiani, C., Baravalle, P., Giraudi, G., & Tozzi, C. (2007). Molecularly imprinted solid-phase extraction method for the high-performance liquid chromatographic analysis of fungicide pyrimethanil in wine. Journal of Chromatography. A, 1141, 158–164.

    Article  CAS  Google Scholar 

  • Bastide, J., Cambon, J. P., Breton, F., Piletsky, S. A., & Rouillon, R. (2005). The use of molecularly imprinted polymers for extraction of sulfonylurea herbicides. Analytica Chimica Acta, 542, 97–103.

    Article  CAS  Google Scholar 

  • Bhardwaj, G. (2007). From pioneering invention to sustained innovation: Herbicides at DuPont. Chemical Heritage, 25(1), 34–36.

    CAS  Google Scholar 

  • Claude, B., Morin, P., Lafosse, M., Belmont, A. S., & Haupt, K. (2008). Selective solid-phase extraction of a triterpene acid from a plant extract by molecularly imprinted polymer. Talanta, 75, 344–350.

    Article  CAS  Google Scholar 

  • Djozan, D., & Ebrahimi, B. (2008). Preparation of new solid phase micro extraction fiber on the basis of atrazine-molecular imprinted polymer: Application for GC and GC/MS screening of triazine herbicides in water, rice and onion. Analytica Chimica Acta, 616, 152–159.

    Article  CAS  Google Scholar 

  • Dong, X. Z., Wang, N., Wang, S. L., Zhang, X. W., & Fan, Z. J. (2004). Synthesis and application of molecularly imprinted polymer on selective solid-phase extraction for the determination of monosulfuron residue in soil. Journal of Chromatography. A, 1057, 13–19.

    Article  CAS  Google Scholar 

  • Fan, Z. J., Liu, F. M., & Qian, C. F. (1999). The present situation and development of sulfonylurea herbicides. Pesticides, 38, 6–9.

    CAS  Google Scholar 

  • Feng, Q. Z., Zhao, L. X., Yan, W., Lin, J. M., Zheng, Z. X., & Hazard, J. (2009). Molecularly imprinted solid-phase extraction combined with high performance liquid chromatography for analysis of phenolic compounds from environmental water samples. Materials, 167, 282–288.

    CAS  Google Scholar 

  • Knopp, A., Knopp, D., & Niessner, R. (1999). Metsulfuron-methyl in different water types. Environmental Science and Technology, 33, 358–361.

    Article  CAS  Google Scholar 

  • Krynitsky, A. J. (1997). Determination of sulfonylurea herbicides in water by capillary electrophoresis and by liquid chromatography/mass spectrometry. Journal of AOAC International, 80, 392–400.

    CAS  Google Scholar 

  • Li, X. Y., Wang, G. J., Sun, J. G., Zheng, Y. T., Yan, B., Xie, H. T., et al. (2007). Determination and pharmacokinetic study of a novel sulfonylurea: Potential hypoglycemic agent in rat plasma. Chromatographia, 65, 13–18.

    Article  CAS  Google Scholar 

  • Liu, X. J., Chen, Z. Y., Zhao, R., Shangguan, D. H., Liu, G. Q., & Chen, Y. (2007). Uniform-sized molecularly imprinted polymer for metsulfuron-methyl by one-step swelling and polymerization method. Talanta, 71, 1205–1210.

    Article  CAS  Google Scholar 

  • Liu, Y. Q., Hoshina, K., & Haginaka, J. (2010). Monodispersed, molecularly imprinted polymers for inchonidine by precipitation polymerization. Talanta, 80, 1713–1718.

    Article  CAS  Google Scholar 

  • Martin, P. D., Jones, G. R., Stringer, F., & Wilson, I. D. (2004). Comparison of extraction of a blocker from plasma onto a molecularly imprinted polymer with liquid–liquid extraction and solid phase extraction methods. Journal of Pharmaceutical and Biomedical Analysis, 35, 1231–1239.

    Article  CAS  Google Scholar 

  • Martínez, R. C., Gonzalo, E. R., & Hernández, E. H. (2006). Behaviour of triazine herbicides and their hydroxylated and dealkylated metabolites on a propazine-imprinted polymer comparative study in organic and aqueous media. Analytica Chimica Acta, 559, 186–194.

    Article  Google Scholar 

  • Molinelli, A., Weiss, R., & Mizaikoff, B. (2002). Advanced solid phase extraction using molecularly imprinted polymers for the determination of quercetin in red wine. Journal of Agricultural and Food Chemistry, 50, 1804–1808.

    Article  CAS  Google Scholar 

  • Penmetsa, K. V., Leidy, R. S., & Shea, D. (1997). Enantiomeric and isomeric separation of herbicides using cyclodextrin-modified capillary zone electrophoresis. Journal of Chromatography. A, 790, 225–234.

    Article  CAS  Google Scholar 

  • Pimentel, D., & Levitan, L. (1986). Pesticides: Amounts applied and amounts reaching pests. Bioscience, 36, 86–91.

    Article  CAS  Google Scholar 

  • Polati, S., Bottaro, M., Frascarolo, P., Gosetti, F., Gianotti, V., & Gennaro, M. C. (2006). HPLC-UV and HPLC-MSn multiresidue determination of amidosulfuron, azimsulfuron, nicosulfuron, rimsulfuron, thifensulfuron methyl, tribenuron methyl and azoxistrobine in surface waters. Analytica Chimica Acta, 579, 146–151.

    Article  CAS  Google Scholar 

  • She, Y. X., Cao, W. Q., Shi, X. M., Lv, X. L., Liu, J. J., Wang, R. Y., et al. (2010). Class-specific molecularly imprinted polymers for the selective extraction and determination of sulfonylurea herbicides in maize samples by high-performance liquid chromatography–tandem mass spectrometry. Journal of Chromatography B, 878, 2047–2053.

    Article  CAS  Google Scholar 

  • Sondhia, S. (2008). Determination of imazosulfuron persistence in rice crop and soil. Environmental Monitoring and Assessment, 137, 205–211.

    Article  CAS  Google Scholar 

  • Song, N. H., Zhang, S., Hong, M., & Yang, H. (2010). Impact of dissolved organic matter on bioavailability of chlorotoluronn to wheat. Environmental Pollution, 158, 906–912.

    Article  CAS  Google Scholar 

  • Sun, Z., Schussler, W., Sengl, M., Niessner, R., & Knoppa, D. (2008). Selective trace analysis of diclofenac in surface andwastewater samples using solid-phase extractionwith a new molecularly imprinted polymer. Analytica Chimica Acta, 620, 73–81.

    Article  CAS  Google Scholar 

  • Tang, K. J., Chen, S. W., Gu, X. H., Wang, H. J., Dai, J., & Tang, J. (2008). Preparation of molecularly imprinted solid phase extraction using bensulfuron-methyl imprinted polymer and clean-up for the sulfonylurea-herbicides in soybean. Analytica Chimica Acta, 614, 112–118.

    Article  CAS  Google Scholar 

  • Tang, K. J., Gu, X. H., Zhu, S., Tang, J., & Wang, H. J. (2009). Spectrum analysis and adsorption characteristics of bensulfuronmethyl molecularly imprinted polymers. China Acta Chimica Sinica, 67, 687–692.

    CAS  Google Scholar 

  • Tran, A. T. K., Hyne, R. V., & Doble, P. (2007). Determination of commonly used polar herbicides in agricultural drainage waters in Australia by HPLC. Chemosphere, 67, 944–953.

    Article  CAS  Google Scholar 

  • Wang, N., Dong, X. Z., Zhang, X. W., Lv, X. Y., Hou, J. F., & Fan, Z. J. (2004). Synthesis and the recognition properties of the monosulfuron imprinted polymer. J Instrum Anal, 23, 13–17.

    Google Scholar 

  • Wu, W. X., Li, L., Yang, G. L., Li, Z. W., & Zhang, G. Q. (2006). Characteristics of molecular recognition of triadimefon imprinting polymer. Chin, Journal of Hebei Univerersity (Natural Science Edition), 26, 396–400.

    CAS  Google Scholar 

  • Wu, Y., Yang, C. Z., & Liu, Y. (2008). Determination of chlorimuron-ethyl in soybeans by GC-MS. Chin J Anal Lab, 27, 80–83.

    Google Scholar 

  • Wu, Y. J., Fu, X. W., & Yang, H. (2011). Cloud point extraction with Triton X-114 for separation of metsulfuron-methyl, chlorsulfuron, and bensulfuron-methyl from water, soil, and rice and analysis by high-performance liquid chromatography. Archives of Environmental Contamination and Toxicology. doi:10.1007/s00244-010-9626-y.

  • Xia, X. R., & Leidy, R. B. (2002). A simplified liquid-solid extraction technique for the analyses of pesticide residues in soil samples. Environmental Monitoring and Assessment, 73, 179–190.

    Article  CAS  Google Scholar 

  • Ye, G. B., Zhang, W., Cui, X., Pan, C. P., & Jiang, S. R. (2006). Determination and quantitation of ten sulfonylureaherbicides in soil samples using liquid chromatography with electrospray ionization mass spectrometric detection. Chinese Journal of Analytical Chemistry, 34, 1207–1212.

    Article  CAS  Google Scholar 

  • Zhu, X. F., Cao, Q., Hou, N. B., Wang, G. S., & Ding, Z. T. (2006a). The preparation and the recognition property of molecularly imprinted polymer of podophyllotoxin. Analytica Chimica Acta, 561, 171–177.

    Article  CAS  Google Scholar 

  • Zhu, X. L., Yang, J., Su, Q. D., Cai, J. B., & Gao, Y. (2006b). Monocrotophos—Specific molecularly imprinted polymers and its spectroscopic study. Spectroscopy and Spectral Analysis, 26, 1817–1820.

    CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge the financial support of the Fundamental Research Funds for the Central Universities of China (no. KYZ200918) for this study.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hong Yang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fu, X.W., Wu, Y.J., Qu, J.R. et al. Preparation and utilization of molecularly imprinted polymer for chlorsulfuron extraction from water, soil, and wheat plant. Environ Monit Assess 184, 4161–4170 (2012). https://doi.org/10.1007/s10661-011-2252-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10661-011-2252-y

Keywords

Navigation