Formation of conversion products and of bound residues of chlorinated anilines in soil

Scheunert, I.; Mansour, M.; Adrian, P.

doi:10.1080/02772249109357679

Cited by 7 publications

(2 citation statements)

References 9 publications

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“…Conversely, the resulting products can be diffused and thus not available for mineralisation or leaching, in particular when degradation is slow (fortuitous degradation or cometabolic degradation) (Soulas, 1993). Lastly, the sequestration or formation of non-extractable residues can contribute in a very significant and quasi-final way to the exclusion of the pollutant from any other process which defines its behaviour in the soil (Scheunert et al, 1991). In this context, the aims of our work were to study the effects of ageing phenanthrene in an agricultural soil.…”

Section: Introductionmentioning

confidence: 99%

Effect of ageing on mobility and sequestration of phenanthrene in an agricultural soil

Amellal

Boivin

Ganier

et al. 2006

Agron. Sustain. Dev.

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-We studied the effect of ageing on the mobility and sequestration of 14 C-phenanthrene in an agricultural soil. We used autovial microcolumns incubated for a period ranging between 0 and 156 days. Our results showed that a large proportion of radioactivity remained extractable by methanol up to 64 days of incubation, amounting from 44.5 to 80.2% of initial radioactivity. Mineralisation of 14 C-phenanthrene began tardily, after the decrease of mineralisation of the soil organic matter. Throughout incubation, mineralisation remained slow and weak, of co-metabolic type, and only 2% of the quantity applied was mineralised over a period of 156 days. The amount of radioactivity leached varied considerably during incubation. Under the effect of water percolation of 64 mm, the quantities exported in equivalent 14 C-phenanthrene went from 0.90 to 0.48 ng/g of soil between 0 and 35 days, then increased up to 1.5 ng/g at 100 days. The radioactivity present in pore water displayed the same dynamic and the same variations. For pore water, this radioactivity represented, in equivalent phenanthrene, 0.09 ng/g of soil up to 46 days, then increased rapidly to reach 0.5 ng/g at 65 days. In both cases (leachates and pore water), enrichment in radioactivity due to the presence of a high proportion of polar compounds reached 89%. Lastly, the formation of non-extractable residues progressed very slowly up to 45 days (5.9 to 13% of the amount applied), after which there was a marked increase, i.e. to 20.7, 32.2 and 35.8% at 52, 64 and 156 days, respectively. These increases in radioactivity in different compartments of soil are correlated with mineralisation of phenanthrene due to preliminary production of degradation products. Thus, the capacity of a soil to degrade and mineralise phenanthrene plays a determining role in the distribution of its residues between the soil solution and the solid matrix. Overall, our results suggest that in agricultural soils contaminated by strongly adsorbed organic compounds, water pollution and sequestration are primarily controlled by degradation.PAH / leaching / diffusion / sequestration / mineralisation / agricultural soil / water quality

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Section: Introductionmentioning

confidence: 99%

Effect of ageing on mobility and sequestration of phenanthrene in an agricultural soil

Amellal

Boivin

Ganier

et al. 2006

Agron. Sustain. Dev.

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“…In contrast to H 2 O 2 -dependent peroxidases, these enzymes simply use oxygen and are widely distributed in fungi. Therefore, laccases have been used several times to characterize binding mechanisms involved in the humification of pesticides derived from aniline compounds (21,32,38).…”

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Structure of a laccase-mediated product of coupling of 2,4-diamino-6-nitrotoluene to guaiacol, a model for coupling of 2,4,6-trinitrotoluene metabolites to a humic organic soil matrix

Dawel¹,

Kästner²,

Michels³

et al. 1997

Appl Environ Microbiol

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This work presents laccase-mediated model reactions for coupling of reduced 2,4,6-trinitrotoluene (TNT) metabolites to an organic soil matrix. The structure of an isolated coupling product of 2,4-diamino-6-nitrotoluene (2,4-DANT) to guaiacol as humic constituent was determined. Among several structures, the compound was identified conclusively to be the trinuclear coupling product 5-(2-amino-3-methyl-4-nitroanilino)-3,3dimethoxy-4,4-diphenoquinone. The compound has a weight of 409 g mol ؊1 and may serve as a model reaction for the biogenic formation of bound residues in soil from TNT by coupling aminotoluenes (reduced TNT metabolites) to humic constituents. A linear correlation of the substrate consumption to the enzyme activity was detected. Based on this observation, the described reaction of 2,4-DANT coupling to guaiacol may be used for determination of laccase activity since the reaction was not inhibited by other compounds of culture supernatants. We propose a two-step mechanism for the coupling reaction because 2,4-DANT was not transformed by laccases in the absence of guaiacol and guaiacol oxidation was independent of the presence of 2,4-DANT. The first reaction step is a laccase-mediated dimerization of two guaiacol monomers with subsequent oxidation to a diphenoquinone. The second step is the nucleophilic addition of 2,4-DANT to the ortho position of the carbonyl group of the diphenoquinone structure.

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Transformation of chemical contaminants by biotic and abiotic processes in water and soil

Mansour

Feicht

1994

Chemosphere

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Formation of conversion products and of bound residues of chlorinated anilines in soil

Cited by 7 publications

References 9 publications

Effect of ageing on mobility and sequestration of phenanthrene in an agricultural soil

Effect of ageing on mobility and sequestration of phenanthrene in an agricultural soil

Structure of a laccase-mediated product of coupling of 2,4-diamino-6-nitrotoluene to guaiacol, a model for coupling of 2,4,6-trinitrotoluene metabolites to a humic organic soil matrix

Transformation of chemical contaminants by biotic and abiotic processes in water and soil

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