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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
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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.

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

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