Hostname: page-component-78c5997874-xbtfd Total loading time: 0 Render date: 2024-11-11T03:12:40.526Z Has data issue: false hasContentIssue false
  • English
  • Français

Adsorption Mechanisms of Imazamethabenz-Methyl on Homoionic Montmorillonite

Published online by Cambridge University Press:  28 February 2024

A. Pusino ,
A. Gelsomino  and
C. Gessa
A. Pusino
Affiliation:
Dipartimento di Agrochimica e Agrobiologia, Università di Reggio Calabria, Piazza San Francesco di Sales 4, 89061, Gallina (RC), Italy
A. Gelsomino
Affiliation:
Dipartimento di Agrochimica e Agrobiologia, Università di Reggio Calabria, Piazza San Francesco di Sales 4, 89061, Gallina (RC), Italy
C. Gessa
Affiliation:
Istituto di Chimica Agraria, Università di Bologna, Via Berti Pichat 11, 40127 Bologna, Italy
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

The adsorption of the herbicide imazamethabenz-methyl, a mixture of the two isomers methyl (±)-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1 H-imidazol-2-yl]-4-methylbenzoate para isomer) and methyl (±)-2-[4,5-dihydro-4-methyl-4-(l-methylethyl)-5-oxo-1 H-imidazol-2-yl]-5-methyl-benzoate (meta isomer), from water onto Al3+, Fe3+-, Ca2+-, K+- and Na+-montmorillonite was studied by analytical (HPLQ methods. The adsorption from an organic solvent was also investigated by spectroscopic (IR) and X-ray diffraction measurements. It was observed that, depending on the acidic properties of the exchangeable cations, two different mechanisms may take place. The first one, acting on Fe3+- and Al3+-clays, involves the protonation of the more basic nitrogen atom of imidazolinone ring of the herbicide because of a proton transfer from the acidic metal-bound water, followed by adsorption on the clay surfaces. In this case, the clay surfaces have greater affinity for the meta than the para isomer, due to the extra-stabilization of the meta protonated form by resonance. The second mechanism, taking place on Ca2+-, K+- and Na+-clays, is hydrogen-bond formation between the ester carbonyl group of the herbicide and hydration water metal ions and is not affected by the structure of the isomers.

Keywords

AdsorptionHydrolysisImazamethabenz-methylInfrared spectroscopyInterlayer cationsMontmorillonitePesticides
Type
Research Article
Information
Clays and Clay Minerals , Volume 43 , Issue 3 , June 1995 , pp. 346 - 352
Copyright
Copyright © 1995, The Clay Minerals Society

References

Allen, R., and Caseley, J. C. 1987. The persistence and mobility of AC 222,293 in cropped and fallow soils. Proc. Br. Crop Prot. Conf. Weeds 2: 569–576.Google Scholar
Bellamy, L. J., 1975. The Infrared Spectra of Complex Molecules. London: Chapman and Hall, 72–96.Google Scholar
Bosetto, M., Arfaioli, P., and Fusi, P. 1993. Interactions of alachlor with homoionic montmorillonites. Soil Sci. 155: 105–113.CrossRefGoogle Scholar
Brown, M. A., Chiu, T. Y., and Miller, P. 1987. Hydrolytic activation versus oxidative degradation of assert herbicide, an imidazolinone aryl-carboxylate, in susceptible wild oat versus tolerant corn and wheat. Pestic. Biochem. Physiol. 27: 24–29.Google Scholar
Curran, W. S., Loux, M. M., Liebl, R. A., and Simmons, F. W. 1992. Photolysis of imidazolinone herbicides in aqueous solutions and on soil. Weed Sci. 40: 143–148.Google Scholar
Gilchrist, F. R., Gamble, D. S., Kodama, H., and Khan, U. S. 1993. Atrazine interactions with clay minerals: Kinetics and equilibria of sorption. J. Agric. Food Chem. 41: 1748–1755.CrossRefGoogle Scholar
Giles, C. H., McEwan, J. H., Nakhwa, S. N., and Smith, D. 1960. Studies in adsorption. XI. A system of classification of solution adsorption isotherms and its use in diagnosis of adsorption mechanisms and in measurements of specific areas of soils. J. Chem. Soc.: 3973–3993.CrossRefGoogle Scholar
Hedlund, K., and Andersson, L. 1987. Assert: a new herbicide for wild oat control. Weeds Weed Control 28: 1–9.Google Scholar
Hendershot, W. H., and Duquette, M. 1986. A simple barium chloride method for determining cation exchange capacity and exchangeable cations. Soil Sci. Soc. J. Amer. 50: 605–608.Google Scholar
Hermosin, M. C., Martin, P., and Cornejo, J. 1993. Adsorption mechanisms of monobutyltin in clay minerals. Environ. Sci. Technol. 27: 2606–2611.Google Scholar
Laird, D. A., Barriuso, E., Dowdy, R. H., and Koskinen, W. C. 1992. Adsorption of atrazine on smectites. Soil Sci. Soc. J. Amer. 56: 62–67.Google Scholar
Micera, G., Pusino, A., Gessa, C., and Petretto, S. 1988. Interaction of fluazifop with Al-, Fe3+-, and Cu2+-saturated montmorillonite. Clays & Clay Miner. 36: 354–358.Google Scholar
Mortland, M. M., 1970. Clay organic-complex and interactions. Adv. Agron. 22: 75–115.Google Scholar
Mortland, M. M., 1976. Interactions between clays and organic pollutants. In Proc. Inter. Conf. Mexico City, 1975. Bailey, S. W., ed. Wilmette, Illinois: Applied Publishing, 469–175.Google Scholar
Nilsson, H., and Arvidsson, T. 1989. Persistence and mobility of herbicides in arable soil. Investigations in 1986–1987. Swed. Crop Prot. Conf. 30: 270–277.Google Scholar
Pusino, A., and Gessa, C. 1990. Catalytic hydrolysis of diclofop-methyl on Ca-, Na-, and K-montmorillonite. Pestic. Sci. 30: 211–216.CrossRefGoogle Scholar
Pusino, A., Liu, W., and Gessa, C. 1993. Dimepiperate adsorption and hydrolysis on Al3+-, Fe3+-, Ca2+-, and Na+-montmorillonite. Clays & Clay Miner. 41: 335–340.Google Scholar
Pusino, A., Micera, G., and Gessa, C. 1991. Interaction of the herbicide acifluorfen with montmorillonite. Formation of insoluble Fe3+, Al3+, Cu2+, and Ca2+ complexes. Clays & Clay Miner. 39: 50–53.Google 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 & Clay Miner. 37: 558–562.Google Scholar
Sposito, G., 1984. The Surface Chemistry of Soils. New York: Oxford University Press, 136 pp.Google Scholar
Rouchaud, J., Gustin, F., and Moulard, C. 1992. Stability of the imidazolin-4-one ring towards hydrolyses and oxidations reactions. Bull. Soc. Chim. Belg. 101: 959–968.Google Scholar
Sánchez-Camazano, M., and Sánchez-Martin, M. J. 1991. Hydrolysis of azinphosmethyl induced by the surface of smectites. Clays & Clay Miner. 39: 609–613.Google Scholar
Solntsev, M. K., Gribova, Z. P., Tashish, V., Kartsev, V. G., and Antonovskil, V. G. 1990. Effect of pyridylimidazolinone herbicides on the photosynthetic apparatus of crop plants and weeds. Izv. Akad. Nauk Kaz. SSR, Ser. Biol. 6: 862–870.Google Scholar
Wauchope, R. D., Buttler, T. M., Hornsby, A. G., Augustijn-Beckers, P. W. M., and Burt, J. P. 1992. The SCS/ARS/CES/pesticides properties database for environmental decision-making. Rev. Environ. Contam. Toxicol. 123: 1–155.Google Scholar
Weber, J. B., 1993. Ionization and sorption of fomesafen and atrazine by soil and soil constituents. Pestic. Sci. 39: 31–38.Google Scholar