Abstract
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.
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References
Allen, R., and J. C. Caseley. 1987. The persistence and mobility of AC 222, 293 in cropped and fallow soils. Proc. Br. Crop Prot. Conf. Weeds 2: 569–576.
Bellamy, L. J. 1975. The Infrared Spectra of Complex Molecules. London: Chapman and Hall, 72–96.
Bosetto, M., P. Arfaioli, and P. Fusi. 1993. Interactions of alachlor with homoionic montmorillonites. Soil Sci. 155: 105–113.
Brown, M. A., T. Y. Chiu, and P. Miller. 1987. Hydrolytic activation versus oxidative degradation of assert herbicide, an imidazolinone aryl-carboxylate, in susceptible wild oat versus tolerant com and wheat. Pestic. Biochem. Physiol. 27: 24–29.
Curran, W. S., M. M. Loux, R. A. Liebl, and F. W. Simmons. 1992. Photolysis of imidazolinone herbicides in aqueous solutions and on soil. Weed Sci. 40: 143–148.
Gilchrist, F. R., D. S. Gamble, H. Kodama, and U. S. Khan. 1993. Atrazine interactions with clay minerals: Kinetics and equilibria of sorption. J. Agric. Food Chem. 41: 1748–1755.
Giles, C. H., J. H. McEwan, S. N. Nakhwa, and D. Smith. 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.
Hedlund, K., and L. Andersson. 1987. Assert: a new herbicide for wild oat control. Weeds Weed Control 28: 1–9.
Hendershot, W. H., and M. Duquette. 1986. A simple barium chloride method for determining cation exchange capacity and exchangeable cations. Soil Sci. Soc. J. Amer. 50: 605–608.
Hermosin, M. C., P. Martin, and J. Cornejo. 1993. Adsorption mechanisms of monobutyltin in clay minerals. Environ. Sci. Technol. 27: 2606–2611.
Laird, D. A., E. Barriuso, R. H. Dowdy, and W. C. Koskinen. 1992. Adsorption of atrazine on smectites. Soil Sci. Soc. J. Amer. 56: 62–67.
Micera, G., A. Pusino, C. Gessa, and S. Petretto. 1988. Interaction of fluazifop with Al-, Fe3+-, and Cu2+-saturated montmorillonite. Clays & Clay Miner. 36: 354–358.
Mortland, M. M. 1970. Clay organic-complex and interactions. Adv. Agron. 22: 75–115.
Mortland, M. M. 1976. Interactions between clays and organic pollutants. In Proc. Inter. Conf. Mexico City, 1975. S. W. Bailey, ed. Wilmette, Illinois: Applied Publishing, 469–475.
Nilsson, H., and T. Arvidsson. 1989. Persistence and mobility of herbicides in arable soil. Investigations in 1986–1987. Swed. Crop Prot. Conf. 30: 270–277.
Pusino, A., and C. Gessa. 1990. Catalytic hydrolysis of diclofop-methyl on Ca-, Na-, and K-montmorillonite. Pestic. Sci. 30: 211–216.
Pusino, A., W. Liu, and C. Gessa. 1993. Dimepiperate adsorption and hydrolysis on Al3+-, Fe3+-, Ca2+-, and Na+- montmorillonite. Clays & Clay Miner. 41: 335–340.
Pusino, A., G. Micera, and C. Gessa. 1991. Interaction of the herbicide acifluorfen with montmorillonite. Formation of insoluble Fe3+, Al3+, Cu2+, and Ca2+ complexes. Clays & Clay Miner. 39: 50–53.
Pusino, A., G. Micera, C. Gessa, and S. Petretto. 1989. Interaction of diclofopand diclofop-methyl with Al3+-, Fe3+-, and Cu2+-saturated montmorillonite. Clays & Clay Miner. 37: 558–562.
Sposito, G. 1984. The Surface Chemistry of Soils. New York: Oxford University Press, 136 pp.
Rouchaud, J., F. Gustin, and C. Moulard. 1992. Stability of the imidazolin-4-one ring towards hydrolyses and oxidations reactions. Bull. Soc. Chim. Belg. 101: 959–968.
Sânchez-Camazano, M., and M. J. Sanchez-Martin. 1991. Hydrolysis of azinphosmethyl induced by the surface of smectites. Clays & Clay Miner. 39: 609–613.
Solntsev, M. K., Z. P., Gribova, V. Tashish, V. G. Kartsev, and V. G. Antonovskil. 1990. Effect of pyridylimidazolinone herbicides on the photosynthetic apparatus of crop plants and weeds. Izv. Akad. Nauk Kaz. SSR, Ser. Biol. 6: 862–870.
Wauchope, R. D., T. M. Buttler, A. G. Hornsby, P. W. M. Augustijn-Beckers, and J. P. Burt. 1992. The SCS/ARS/CES/pesticides properties database for environmental decision-making. Rev. Environ. Contam. Toxicol. 123: 1–155.
Weber, J. B. 1993. Ionization and sorption of fomesafen and atrazine by soil and soil constituents. Pestic. Sci. 39: 31–38.
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Pusino, A., Gelsomino, A. & Gessa, C. Adsorption Mechanisms of Imazamethabenz-Methyl on Homoionic Montmorillonite. Clays Clay Miner. 43, 346–352 (1995). https://doi.org/10.1346/CCMN.1995.0430309
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DOI: https://doi.org/10.1346/CCMN.1995.0430309