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Adsorption of Two Quinolinecarboxylic Acid Herbicides on Homoionic Montmorillonites

Published online by Cambridge University Press:  01 January 2024

Alba Pusino ,
Antonio Gelsomino ,
Maria G. Fiori  and
Carlo Gessa
Alba Pusino*
Affiliation:
Dipartimento di Scienze Ambientali Agrarie e Biotecnologie Agro-Alimentari, Università di Sassari, Viale Italia 39, 07100 Sassari, Italy
Antonio Gelsomino
Affiliation:
Dipartimento di Biotecnologie per il Monitoraggio Agroalimentare ed Ambientale, Università degli Studi Mediterranea di Reggio Calabria, Feo di Vito, 89124 Reggio Calabria, Italy
Maria G. Fiori
Affiliation:
Dipartimento di Scienze Ambientali Agrarie e Biotecnologie Agro-Alimentari, Università di Sassari, Viale Italia 39, 07100 Sassari, Italy
Carlo Gessa
Affiliation:
Dipartimento di Scienze et Tecnologie Agro-Ambientali, Università di Bologna, Via Fanin 40, 40127 Bologna, Italy
*
*E-mail address of corresponding author: [email protected]
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Abstract

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The adsorption of the herbicides quinmerac 7-chloro-3-methylquinoline-8-carboxylic acid (QMe) and quinclorac 3,7-dichloroquinoline-8-carboxylic acid (QCl) on homoionic Fe3+-, Al3+-, Cu2+-, Ca2+-, K+- and Na+-exchanged montmorillonite was studied in aqueous solution. Adsorption data were fitted to the logarithmic form of the Freundlich equation. Ca- and Na-exchanged montmorillonites were ineffective in the adsorption of QMe. On the other hand, the QMe adsorption on Fe-exchanged montmorillonite was rapid and the equilibrium was attained after 15 min. An H-type isotherm was observed for the QMe adsorption on Fe-clay, indicating a high affinity of the solute for the sorption sites and almost complete adsorption from dilute solution. On the other hand, the adsorption isotherm of QMe on Al- and K-clay was of the S-type. This shape suggests that the solvent molecules may compete for the sorption sites. A Fourier transform infrared (FTIR) study suggested that the adsorption mechanism of QMe on Fe-, Al- and K-clay involves the protonation of QMe molecule due to the acidic water surrounding the saturating cations. The greater acidity of Fe-clay compared with Al- and K-clay explains both the lower QMe adsorption observed on Al and K systems and the lack of adsorption on Na and Ca systems. In contrast, the formation of a Cu complex permitted QMe to be adsorbed to a large extent to Cu-clay as shown by FTIR analysis. The QCl was adsorbed only by Fe-clay and the adsorption isotherm of QCl on Fe clay was of the S-type. This finding is consistent with the lower basic character of the QCl molecule nitrogen. In fact, the replacement of the electron-releasing methyl group in QMe with an electron-withdrawing Cl atom to form QCl makes the nitrogen lone-pair electrons of the quinoline ring unavailable for either protonation or complexation.

Keywords

AdsorptionHerbicidesInfrared SpectroscopyMontmorilloniteQuincloracQuinmerac
Type
Research Article
Information
Clays and Clay Minerals , Volume 51 , Issue 2 , April 2003 , pp. 143 - 149
Copyright
Copyright © 2003, The Clay Minerals Society

References

Calamai, L. Pantani, O. Pusino, A. Gessa, C. and Fusi, P., (1997) Interaction of rimsulfuron with smectites Clays and Clay Minerals 45 1–5 10.1346/CCMN.1997.0450103.Google Scholar
Chism, W.J. Bingham, S.W. and Shaver, R.L., (1991) Uptake, translocation, and metabolism of quinclorac in two grass species Weed Technology 5 771–775 10.1017/S0890037X00033832.Google Scholar
Cook, D., (1961) Vibrational spectra of pyridinium salts Canadian Journal of Chemistry 39 2004 2024.Google Scholar
Cox, L. Hermosín, M.C. and Cornejo, J., (1995) Adsorption and desorption of the herbicide thiazafluron as a function of soil properties International Journal of Environment Analytical Chemistry 58 305–314 10.1080/03067319508033132.Google Scholar
Deschauer, H. and Kögel-Knabner, I., (1990) Sorption behavior of a new acidic herbicide in soils Chemosphere 21 1397–1410 10.1016/0045-6535(90)90044-T.Google Scholar
Duda, A.M. Dyba, M. Kozlowski, H. Micera, G. and Pusino, A., (1996) Copper(II) complexes of the imidazolinone herbicide imazapyr Journal of Agricultural and Food Chemistry 44 3698–3702 10.1021/jf9507856.Google Scholar
Giles, C.H. MacEwan, T.H. Nakhwa, S.N. and Smith, D., (1960) Studies in adsorption: Part XI. A system of classification of solution adsorption isotherms, and its use in diagnosis of adsorption mechanisms and in measurement of specific surface areas of solids Journal of the Chemical Society 111 3973–3993 10.1039/jr9600003973.Google Scholar
Grossmann, K., (1998) Quinclorac belongs to a new class of highly selective auxin herbicides Weed Science 46 707 716.Google Scholar
Grossmann, K. and Scheltrup, F., (1995) On the mode of action of new, selective herbicide quinmerac Proceedings Brighton Crop Protection Conference — Weed 393 398.Google Scholar
Grossmann, K. and Scheltrup, F., (1997) Selective induction of 1-aminocyclopropane-1 carboxylic acid (ACC) synthase activity is involved in the selective of the auxin herbicide quinclorac between barnyard grass and rice Pesticide Biochemistry and Physiology 58 148–153 10.1006/pest.1997.2290.CrossRefGoogle Scholar
Haderlein, S.B. and Schwarzenbach, R.P., (1993) Adsorption of substituted nitrobenzene and nitrophenols to mineral surfaces Environmental Science and Technology 27 316–326 10.1021/es00039a012.Google Scholar
Haderlein, S.B. Weissmahr, K.W. and Schwarzenbach, R.P., (1996) Specific adsorption of nitroaromatic explosives and pesticides to clay minerals Environmental Science and Technology 30 612–622 10.1021/es9503701.Google Scholar
Hendershot, W.H. and Duquette, M., (1986) A simple barium chloride method for determining cation exchange capacity and exchangeable cations Soil Science Society of America Journal 50 605–608 10.2136/sssaj1986.03615995005000030013x.Google Scholar
Hermens, J.L.M., (1989) Quantitative structure-activity relationships of environmental pollutants The Handbook of Environmental Chemistry 3D 111–162 10.1007/978-3-540-46161-6_3.Google Scholar
Hill, B.D. Moyer, J.R. Inaba, D.J. and Doram, R., (1998) Effect of moisture on quinclorac dissipation in Lethbridge soil Canadian Journal of Plant Science 78 697–702 10.4141/P97-119.Google Scholar
Kowalska, M. Güler, H. and Cocke, D.L., (1994) Interactions of clay minerals with organic pollutants Science of the Total Environment 141 223–240 10.1016/0048-9697(94)90030-2.Google Scholar
Lide, D.R., (1992) CRC Handbook of Chemistry and Physics 73rd Boca Raton, Florida CRC Press 8 38.Google Scholar
Mabury, S.A. and Crosby, D.G., (1996) Pesticide reactivity toward hydroxyl and its relationship to field persistence Journal of Agricultural and Food Chemistry 44 1920–1924 10.1021/jf950423y.Google Scholar
Mortland, M.M., Huang, P.M. and Schnitzer, M., (1986) Mechanisms of adsorption of non-humic organic species by clays Interactions of Soil Minerals with Natural Organics and Microbes Madison, Wisconsin Soil Science Society of America 59 76.Google Scholar
Ortego, J.D.L. Kowalska, M. and Cocke, D.L., (1991) Interactions of montmorillonite with organic compounds — adsorptive and catalytic properties Chemosphere 22 769–798 10.1016/0045-6535(91)90052-F.Google Scholar
Pouchert, C.J., (1975) The Aldrich Library of Infrared Spectra 2nd Milwaukee, Wisconsin Aldrich Chemical Company 1178 No. H5740-8.Google Scholar
Pusino, A. Gessa, C. and Kozlowski, H., (1988) Catalytic hydrolysis of Quinalphos on homoionic clays Pesticide Science 24 1–8 10.1002/ps.2780240102.CrossRefGoogle Scholar
Pusino, A. Micera, G. Gessa, C. and Petretto, S., (1989) Interaction of diclofop and diclofop-methyl with Al3+-, Fe3+-, and Cu2+-saturated montmorillonite Clays and Clay Minerals 37 558–562 10.1346/CCMN.1989.0370609.Google Scholar
Schwandt, H. Kögel-Knabner, I. Stanjek, H. and Totsche, K., (1992) Sorption of an acidic herbicide on synthetic iron oxides and soils: sorption isotherms The Science of the Total Environment 123/124 121–131 10.1016/0048-9697(92)90139-J.Google Scholar
Strinna Erre, L. Garribba, E. Micera, G. Pusino, A. and Sanna, D., (1997) Copper(II) complexes of imidazolinone herbicides Inorganica Chimica Acta 255 215–220 10.1016/S0020-1693(96)05355-8.Google Scholar
Sunohara, Y. and Masumoto, H., (1977) Comparative physiological effects of quinclorac and auxin, and light involvement in quinclorac-induced chlorosis in corn leaves Pesticide Biochemistry and Physiology 58 125–132 10.1006/pest.1997.2289.Google Scholar
Vasudevan, D. Cooper, E.L. and Van, E.O., (2002) Sorption-desorption of ionogenic compounds at the mineral-water interface: study of metal oxide-rich soils and pure-phase minerals Environmental Science and Technology 36 501–511 10.1021/es0109390.Google Scholar
Worthing, C.R. and Hance, R.J., (1991) The Pesticide Manual 9th UK The British Crop Council 749 750.Google Scholar