Korean Journal of Environmental Agriculture (한국환경농학회지)

The Korean Society of Environmental Agriculture (한국환경농학회)
권호 표지
DOI QR코드

DOI QR Code

Adsorption Pattern of the Herbicide, Bentazon and Its Metabolites on Soil

제초제 Bentazon과 그 대사산물들의 토양 중 흡착양상

  • Kim, Jong-Soo (School of Applied Bioscience, Kyungpook National University) ;
  • Kim, Jang-Eok (School of Applied Bioscience, Kyungpook National University)
  • 김종수 (경북대학교 농업생명과학대학 응용생명과학부) ;
  • 김장억 (경북대학교 농업생명과학대학 응용생명과학부)
  • Published : 2009.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

In order to elucidate the adsorption mechanism of the herbicide, bentazon and its metabolites on soil, their adsorption patterns on soil and six adsorbents were investigated with Freundlich, Langmuir and linear isotherm. Freundlich constants ($K_f$) and maximum adsorption amount($Q^0$) of bentazon on soil was 0.55 and 3.97. Kd and Koc values of it were 0.18 and 18. The all of metabolites used except deisopropylbentazon amounts sorbed on the soil were much higher than bentazon. The most of 8-hydroxybentazon was adsorbed on soil showing $K_f$ = 316.6, $Q^0$ = 3,488, Kd = 29.7 and Koc = 2,970. Bentazon, deisopropylbentazon and 8-hydroxybentazon were shown high affinity to anion exchange regardless of pH and $NH_2$ in low pH range. Reversed phase $C_{18}$ resulted in 100% retention of N-methylbentazon regardless of pH and other metabolites were retained below 40%. The AIBA was strongly adsorbed in silica gel, COOH and cation exchange phase but poor retention was on anion exchange sorbent. 2-Aminobenzoic acid showed an amphipathic nature which had high affinity for COOH and cation exchange phase at pH 7.0 as well as $NH_2$ and anion exchange sorbent at pH 3.0.

제초제 bentazon과 그 대사산물들의 토양흡착 양상을 Freundlich, Langmuir 그리고 linear isotherm을 이용하여 파악하고 기능이 다른 흡착제들과의 흡착특성을 조사하였다. 토양에 대한 bentazon의 $K_f$ = 0.55 L/kg, $Q^0$ = 3.97mg/kg, Kd = 0.18 L/kg 그리고 $K_{oc}$ = 18 L/kg로 나타났다. Deisopropylbentazon을 제외한 다른 대사산물들의 토양 흡착량은 bentazon보다 많았으며 특히 8-hydroxybentazon의 경우 $K_f$ = 316.5 L/kg, $Q^0$ = 3,448 mg/kg, $K_d$ = 29.7 L/kg 그리고 $K_{oc}$ = 2,970 L/kg으로 토양 중에서 대부분이 흡착되는 것으로 나타났다. 여러 기능을 가진 SPE 충진제를 이용하여 bentazon과 그 대사산물들의 흡착양상을 확인한 결과 bentazon, deisopropylbentazon 및 8-hydroxybentazon은 $NH_2$와 anion exchange phase에 친화성이 큰 것으로 나타났다. N-methylbentazon의 경우 $C_{18}$에 큰 친화력을 보였으나 normal phase인 silica gel에는 상대적으로 다른 화합물보다 친화력이 낮았다. IBA는 silica gel, COOH 그리고 cation exchange phase에 강한 흡착을 보였으며 상대적으로 $NH_2$ 그리고 anion exchange phase에는 친화력이 낮았다. 2-Aminobenzoic acid의 경우 pH 3.0에서는 COOH, cation exchange phase에 많은 retention을 보였으며 pH 7.0에서는 $NH_2$, anion exchange phase에 큰 흡착량을 보였다.

Keywords

References

  1. McBride, M. B. (1994) Environmental Chemistry of Soils, Oxford University Press, New York, USA, p. 342-390
  2. Carroll, M. (2008) The Fate of Nutrients and Pesticides in the Urban Environment, ACS, USA, p.187-202
  3. Gevao, B., Semple, K. T. and Jone, K. C. (2000) Bound pesticide residues in soils: a review, Environmental Pollution 108, 3-14
  4. Ferreira, J. A., Martin-Neto, L., Vaz, C. M. P. and Regitano, J. B. (2002) Sorption interaction between imazaquin and a humic acid extracted from a typical Brazilian oxisol, J. Environ. Qual. 31, 1665-1670 https://doi.org/10.2134/jeq2002.1665
  5. Alessandro, D. S. (2001) Factor affecting sorption of organic compounds in natural sorbent/water system and sorption coefficients for selected pollutants. A review, J. Phys. Chem. 30, 252-438
  6. Tomlin, C. D. S. (2006) The Pesticide Manual(14th), British Crop Protection Council, UK, p.82-84
  7. Sanchez-Camazano, M., Sanchez-Martin, M. J. and Delgado-Pascual, R. (2000) Adsorption and mobility of linuron in soils as influenced by soilproperties, organic amendments, and surfactants. J. Agric. Food Chem. 48(7), 3018-3026 https://doi.org/10.1021/jf990812i
  8. Huber, R. and Otto, S. (1994) Environmental behavior of bentazon herbicide. Rev. Environ. Contam. Toxicol. 137, 111-134 https://doi.org/10.1007/978-1-4612-2662-8_3
  9. Wagner, S. C., Zablotowicz, R. M., Gaston, L. A., Locke, M. A. and Kinsella, J. (1996) Bentazon degradation in soil: Influence of tillage and history of bentazon application. J. Agric. Food Chem. 44, 1593-1598 https://doi.org/10.1021/jf950551m
  10. Lee, J. K., Führ, F. and Mittelstaed, W. (1988) Formation and bioavailability of bentazon residues in a German and Korean agricultural soil. Chemosphere 8, 17, 441-450 https://doi.org/10.1016/0045-6535(88)90233-0
  11. Kim, J.-E., Fernandes, E. and Bollag, J.-M. (1997) Enzymatic coupling of the herbicide bentazon with humus monomers and characterization of reaction products. Environ. Sci. Technol. 31, 2392-2398 https://doi.org/10.1021/es961016l
  12. Kim, J.-E., Wang, C. J. and Bollag, J.-M. (1998) Interacyion of reactive and inert chemicals in the presence of oxidoreductase: Reaction of the herbicide bentazon and its metabolites with humic monomers, Biodegradation 8, 387-392
  13. Kim, J.-S., Park, J.-W., Lee, S.-E. and Kim, J.-E. (2002) Formation of bound residues of 8-hydroxybentazon by oxidoreductive catalysts in soil, J. Agric. Food Chem. 50, 3507-3511 https://doi.org/10.1021/jf011504z
  14. Nemeth-Konda, L., Fuleky, G. and Csokan, P. (2002) Sorption behaviour of acetochlor, atrazine, carbendazim,diazinon, imidacloprid and isoproturonon Hungarian agricultural soil. Chemosphere 48, 545-552 https://doi.org/10.1016/S0045-6535(02)00106-6
  15. Tolls, J. (2001) Sorption of veterinary pharmaceuticals in soils: A Review. Environ. Sci. Technol. 35(17), 3397-3406 https://doi.org/10.1021/es0003021
  16. Cox, L., Celis, R., Hermosin, M. C., Cornejo, J., Zsolnay, A. and Zeller, K. (2000) Effect of organic amendments on herbicide sorption as related to the nature of the dissolved organic matter. Environ. Sci. Technol. 34(21), 4600-4605 https://doi.org/10.1021/es0000293
  17. Tunega, D., Haberhauer, G., Gerzabek, M. H. and Lischka, H. (2002) Theoretical study of adsorption sites on the surfaces of 1:1 clay minerals, Langmuir 18(1), 139-147 https://doi.org/10.1021/la010914e
  18. Hesketh, N., Jones, M. N. and Tipping, E. (1996) The interaction of some pesticides and herbicides with humic substances, Analytica Chimica Acta. 327(3), 191-201 https://doi.org/10.1016/0003-2670(96)00081-5
  19. Beck, A. J. and Jones, K. C. (1996) The effects of particle size, organic matter content, crop residues and dissolved organic matter on the sorption kinetics of atrazine and isoproturon by clay soil, Chemosphere 32(12), 2345-2358 https://doi.org/10.1016/0045-6535(96)00147-6
  20. Suzuki, M. N., Amano, K. I. and Yamads, S. (2001) Relation of sorption behavior of agricultural chemicals in solid-phase extraction with their n-octanol/water partition coefficients evaluated by high-performance liquid chromatography (HPLC), Analytica Chimica Acta.. 428(2), 219-226 https://doi.org/10.1016/S0003-2670(00)01250-2
  21. Thorstensen, C. W. and Christiansen, A. (2001) Determination of bentazone, dichlorprop, and MCPA in different soils by sodium hydroxide extraction in combination with solid-phase preconcentration, J. Agric. Food Chem. 49(9), 4199-4202 https://doi.org/10.1021/jf0014415
  22. Thorstensen, C. W., Lode, O. and Christiansen, A. L. (2000) Development of a solid-phase extraction method for phenoxy acids and bentazone in water and comparison to a liquid-liquid extraction method. J. Agric. Food Chem. 48(12), 5829-5833 https://doi.org/10.1021/jf0000124
  23. Henriksen, T., Svensmark, B., Lindhardt, B. and Juhler, R. (2001) Analysis of acidic pesticides using in situ derivatization with alkylchloroformate and solid-phase microextraction (SPME) for GC-MS. Chemosphere 44(7), 1531-1539 https://doi.org/10.1016/S0045-6535(00)00532-4
  24. Timothy, L.G., Glenn, R.W., Ben, F. H. and Robert, H. W. (1996) Sorption and mobility of bentazon in coastal plain soils. Weed Science 44, 166-170
  25. Lerch, R. N., Thurman, E. M. and Kruger, E. L. (1997) Mixed-mode sorption of hydroxylated atrazine degradation products to soil: A mechanism for bound residue. Environ. Sci. Technol. 31, 1539-1546 https://doi.org/10.1021/es960811w

Cited by

  1. Fate of Bentazon Metabolites in Soils vol.45, pp.6, 2012, https://doi.org/10.7745/KJSSF.2012.45.6.936