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Interactions of two sulfonylurea herbicides with organoclays

Published online by Cambridge University Press:  01 January 2024

Maria Jose Carrizosa ,
Maria del Carmen Hermosin ,
William C. Koskinen  and
Juan Cornejo
Maria Jose Carrizosa
Affiliation:
USDA-ARS, Soil and Water Management Research Unit, 1991 Upper Buford Cir. Rm 439, St. Paul, MN 55108, USA
Maria del Carmen Hermosin
Affiliation:
Instituto de Recursos Naturales y Agrobiologia de Sevilla, CSIC, P.O. Box 1052, 41080 Sevilla, Spain
William C. Koskinen*
Affiliation:
USDA-ARS, Soil and Water Management Research Unit, 1991 Upper Buford Cir. Rm 439, St. Paul, MN 55108, USA
Juan Cornejo
Affiliation:
Instituto de Recursos Naturales y Agrobiologia de Sevilla, CSIC, P.O. Box 1052, 41080 Sevilla, Spain
*
*E-mail address of corresponding author: koskinen@umn.edu
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Abstract

The sorption of two sulfonylurea herbicides (SU), metsulfuron methyl and nicosulfuron, on pure clays and organoclays was investigated. Three clays (Arizona smectite, SAz-1, Wyoming smectite, SWy-2, and hectorite, SHCa-1), were treated with amounts of octadecylammonium (ODA) or dioctadecyldimethylammonium (DODMA) cations equal to ∼50 and 100% of the clays’ cation exchange capacity (CEC). Sorption isotherms were fitted to the Freundlich equation. While no measurable sorption was found on the pure clays (Kf = 0), organoclays prepared using both primary and quaternary amines were effective as SU sorbents. The metsulfuron methyl Kf values ranged between 196 and 1498 µmol1−1/n kg−1 L1/n, and Kf values for nicosulfuron, which were lower than those of metsulfuron methyl, ranged from 35 to 198 umol1−1/n kg−1 L1/n. As shown by sorption coefficients, Kd and KOC, SWy-2 treated with DODMA at ∼100% of the CEC was the most effective sorbent for metsulfuron, Kd = 684 L kg−1 and KOC = 2138 L kg−1. For nicosulfuron the most effective sorbent was SAz-1 with ODA at ∼ 50% of the CEC (Kd = 147 L kg−1 and KOC = 1233 L kg−1). In contrast to other weak-acid herbicides, such as phenoxy and picolinic acids, no clear relationships were found between sorption and layer charge, organic carbon content, and basal spacing of the organoclays for both sulfonylurea herbicides. Sorption of both herbicides on organoclays was assumed to involve hydrophobic and polar interactions for which the availability of interlayer room between organocations was a very important factor.

Keywords

MetsulfuronNicosulfuronOrganoclaysSorptionSulfonylureas
Type
Research Article
Information
Clays and Clay Minerals , Volume 52 , Issue 5 , October 2004 , pp. 643 - 649
Copyright
Copyright © 2004, The Clay Minerals Society

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References

Aguer, J.P. Calderon, M.J. Hermosin, M.C. and Cornejo, J., (2000) Fenuron sorption by homoionic natural and modified smectites Journal of Environmental Science and Health B35 279–296 10.1080/03601230009373270.Google Scholar
Anderson, J.J. and Dulka, J.J., (1985) Environmental fate of sulfometuron methyl in aerobic soils Journal of Agricultural and Food Chemistry 33 596–602 10.1021/jf00064a010.Google Scholar
Beyer, E.M. Duffy, M.F. Hay, J.V. Schlueter, D.D., Kearney, P.C. and Kaufman, D.D., (1988) Sulfonylureas Herbicides: Chemistry, Degradation, Mode of Action, Volume 3 New York Marcel Dekker Inc 117–189.Google Scholar
Blair, A.H. and Martin, T.D., (1988) A review of the activity, fate and mode of action of sulfonylurea herbicides Pesticide Science 22 195–219 10.1002/ps.2780220303.Google Scholar
Boyd, S.A. Lee, J.F. and Mortland, M.M., (1988) Attenuating organic contaminant mobility by soil modification Nature 333 345–347 10.1038/333345a0.Google Scholar
Boyd, S.A. Lee, J.F. Mortland, M.M. and Chiou, C.T., (1988) Sorption characteristics of organic compounds on hexadecyltrimethylammonium-smectite Soil Science Society of America Journal 52 652–657 10.2136/sssaj1988.03615995005200030010x.Google Scholar
Brown, H.R., (1990) Mode of action, crop selectivity, and soil relations of the sulfonylurea herbicides Pesticide Science 29 263–281 10.1002/ps.2780290304.Google Scholar
Burris, D.R. and Antworth, C.P., (1992) In-situ modification of aquifer material by a cationic surfactant to enhance retardation of organic contaminants Journal of Contaminant Hydrology 10 325–337 10.1016/0169-7722(92)90014-6.Google Scholar
Carrizosa, M.J. Calderon, M.J. Hermosin, M.C. and Cornejo, J., (2000) Organoclay as sorbent and carrier of the herbicide bentazone The Science of the Total Environment 247 285–293 10.1016/S0048-9697(99)00498-2.Google Scholar
Carrizosa, M.J. Koskinen, W.C. Hermosin, M.C. and Cornejo, J., (2001) Dicamba adsorption-desorption on organoclays Applied Clay Science 18 223–231 10.1016/S0169-1317(01)00037-0.Google Scholar
Carrizosa, M.J. Koskinen, W.C. Hermosin, M.C. and Cornejo, J., (2003) Organosmectites to reduce leaching of acidic herbicides Soil Science Society of America Journal 67 511–517 10.2136/sssaj2003.5110.Google Scholar
Celis, R. Koskinen, W.C. Carrizosa, M.J. Cecchi, A. Ulibarri, M.A. Pavlovic, I. and Hermosin, M.C., (1999) Sorption of ionizable pesticide imazamox by organic clay and organohydrotalcites Journal of Environmental Science and Health B34 929–941 10.1080/03601239909373237.Google Scholar
Celis, R. Koskinen, W.C. Hermosin, M.C. Ulibarri, M.J. and Cornejo, J., (2000) Triadimefon interactions with organoclays and organohydrotalcites Soil Science Society of America Journal 64 36–43 10.2136/sssaj2000.64136x.Google Scholar
Celis, R. Hermosin, M.C. Carrizosa, M.J. and Cornejo, J., (2002) Inorganic and organic clays as carriers for controlled release of the herbicide hexazinone Journal of Agricultural and Food Chemistry 50 2324–2330 10.1021/jf011360o.Google Scholar
Celis, R. Hermosin, M.C. Hermosin, L. Carrizosa, M.J. and Cornejo, J., (2002) Clay-herbicide complexes to retard picloram leaching in soil International Journal of Environmental Analytical Chemistry 82 503–517 10.1080/03067310290018785.Google Scholar
Cox, L. Celis, R. Hermosin, M.C. Koskinen, W.C. and Cornejo, J., (2000) Use of natural soil colloids to retard simazine and 2, 4-D leaching in soil Journal of Agricultural and Food Chemistry 48 93–99 10.1021/jf990585k.Google Scholar
Cox, L. Hermosin, M.C. Koskinen, W.C. and Cornejo, J., (2001) Interactions of imidacloprid with organic- and inorganic-exchanged smectites Clay Minerals 36 267–274 10.1180/000985501750177997.Google Scholar
El-Nahhal, Y. Nir, S. Polubesova, T. Margulies, L. and Rubin, B., (1998) Leaching, phytotoxicity, and weed control of new formulations of alachlor Journal of Agricultural and Food Chemistry 46 3305–3313 10.1021/jf971062k.Google Scholar
El-Nahhal, Y. Nir, S. Polubesova, T. Margulies, L. and Rubin, B., (1999) Movement of metholachlor in soil: effect of new organoclay formulations Pesticide Science 55 857–864 10.1002/(SICI)1096-9063(199908)55:8<857::AID-PS24>3.0.CO;2-P.Google Scholar
El-Nahhal, Y. Nir, S. Servan, C. Rabinovitch, O. and Rubin, B., (2000) Montmorillonite-phenyltrimethylammonium yields environmentally improved formulations of hydrophobic herbicides Journal of Agricultural and Food Chemistry 48 4797–4801 10.1021/jf000327j.Google Scholar
Giles, C.H., MacEwan, S.N., Nakhwa, S.N. and Smith, D. (1960) Studies in adsorption. Part XI. A system of classification of solution adsorption isotherm, and its use in diagnosis of adsorption mechanisms and in measurement of specific surface area in solids. Journal of the Chemical Society, 3973–3993.Google Scholar
Gullick, R.W. and Weber, W.J., (2001) Evaluation of shale and organoclays as sorbent additives for low-permeability soil containment barriers Environmental Science and Technology 35 1523–1530 10.1021/es0015601.Google Scholar
Hermosin, M.C. and Cornejo, J., (1992) Removing 2, 4-D from water by organo-clays Chemosphere 24 1493–1503 10.1016/0045-6535(92)90270-2.Google Scholar
Hermosin, M.C. and Cornejo, J., (1993) Binding mechanism of 2, 4-dichlorophenoxy-acetic acid by organoclays Journal of Environmental Quality 22 325–331 10.2134/jeq1993.00472425002200020013x.Google Scholar
Hultgren, R.P. Hudson, R.J.M. and Sims, G.K., (2002) Effects of soils pH and soil water content on prosulfuron dissipation Journal of Agricultural and Food Chemistry 50 3236–3243 10.1021/jf011477c.Google Scholar
Jaynes, W.F. and Boyd, S.A., (1991) Clay mineral type and organic compound sorption by hexadecyltrimethylammonium exchanged clays Soil Science Society of America Journal 55 43–48 10.2136/sssaj1991.03615995005500010007x.Google Scholar
Jaynes, W.F. and Vance, G.F., (1996) BTEX sorption by organoclays: Cosorptive enhancement and equivalence of interlayer complexes Soil Science Society of America Journal 60 1742–1749 10.2136/sssaj1996.03615995006000060019x.Google Scholar
Koterba, M.T. Banks, W.S.L. and Shedlock, R.J., (1993) Pesticides in shallow groundwater in the Delmarva Peninsula Journal of Environmental Quality 22 500–518 10.2134/jeq1993.00472425002200030015x.Google Scholar
Lagaly, G., (1982) Layer charge heterogeneity in vermiculites Clays and Clay Minerals 30 215–222 10.1346/CCMN.1982.0300308.Google Scholar
Lagaly, G. and Weiss, A. (1969) Determination of the layer charge in mica-type layer silicates. Proceedings of the International Clay Conference, 1968, Tokyo, pp. 61–80.Google Scholar
Lee, J.F. Crum, J.R. and Boyd, S.A., (1989) Enhanced retention of organic contaminants by soils exchanged with organic cations Environmental Science and Technology 23 1365–1372 10.1021/es00069a006.Google Scholar
Lo, I.M.C., (2001) Organoclay with soil-bentonite admixture as waste containment barriers Journal of Environmental Engineering 127 759–759.Google Scholar
Martins, J.M.F. and Mermoud, A., (1999) Transport of rimsulfuron and its metabolites in soil colums Chemosphere 38 601–619 10.1016/S0045-6535(98)00197-0.Google Scholar
Mersie, W. and Foy, C.L., (1986) Adsorption, desorption, and mobility of chlorsulfuron in soils Journal of Agricultural and Food Chemistry 34 89–92 10.1021/jf00067a024.Google Scholar
Mortland, M.M., (1970) Clay-organic interactions Advances in Agronomy 23 75–117 10.1016/S0065-2113(08)60266-7.Google Scholar
Mortland, M.M. Shaobai, S. and Boyd, S.A., (1986) Clay organic complexes as adsorbents for phenol and chlorophenols Clays and Clay Minerals 34 581–585 10.1346/CCMN.1986.0340512.Google Scholar
Nennemann, A. Mishael, Y. Nir, S. Rubin, B. Polubesova, T. Bergaya, F. van Damme, H. and Lagaly, G., (2001) Claybased formulations of metolachlor with reduced leaching Applied Clay Science 18 265–275 10.1016/S0169-1317(01)00032-1.Google Scholar
Pal, O.R. and Vanjara, A.K., (2001) Removal of malathion and butachlor from aqueous solution by clays and organoclays Separation and Purification Technology 24 167–172 10.1016/S1383-5866(00)00226-4.Google Scholar
Park, D.J. Jackson, W.R. McKinnon, I.R. Marzhall, M. and Scher, H.B., (1999) Controlled release of pesticides from microparticles Controlled-Release Delivery Systems for Pesticides New York Marcel Dekker Inc. 89–136.Google Scholar
Ritter, W.F. Chirnside, A.E.M. and Scarborough, R.W., (1996) Movement and degradation of triazines, alachlor, and metolachlor in sandy soils Journal of Environmental Science and Health B31 2699–2721.Google Scholar
Serratosa, J.M. Johns, R.D. and Shimoyama, A., (1970) IR study of alkylammonium vermiculite complexes Clays and Clay Minerals 18 107–113 10.1346/CCMN.1970.0180206.Google Scholar
Smith, J.A. and Jaffe, P.R., (1994) Benzene transport through landfill liners containing organophilic bentonite Journal of Environmental Engineering 120 1559–1577 10.1061/(ASCE)0733-9372(1994)120:6(1559).Google Scholar
van Olphen, H. and Fripiat, J.J., (1979) Data Handbook for Clay Minerals and other Non-metallic Minerals Oxford, UK Pergamon.Google Scholar
Wagner, J. Chen, H. Brownawell, B.J. and Westall, J.C., (1994) Use of cationic surfactants to modify soil surfaces to promote sorption and retard migration of hydrophobic organic compounds Environmental Science and Technology 28 231–237 10.1021/es00051a008.Google Scholar
Xu, S.G. Sheng, G. and Boyd, S.A., (1997) Use of organoclays in pollution abatement Advances in Agronomy 59 25–62 10.1016/S0065-2113(08)60052-8.Google Scholar
Yelverton, F.H. Weber, J.B. Peedin, G. and Smith, W.D., (1990) Using activated charcoal to inactivate agricultural chemical spills Raleigh, NC, USA AG-442, Agricultural Extension Service North Carolina State University.Google Scholar
Zhao, H. Jaynes, W.F. and Vance, G.F., (1996) Sorption of the ionizable organic compound, dicamba (3, 6-dichloro-2-methoxy benzoic acid), by organo-clays Chemosphere 33 2089–2100 10.1016/0045-6535(96)00296-2.Google Scholar