Rapid incorporation and short-term distribution of a nonylphenol isomer and the herbicide MCPA in soil-derived organo-clay complexes

Riefer, Patrick; Klausmeyer, Timm; Schwarzbauer, Jan; Schäffer, Andreas; Schmidt, Burkhard; Corvini, Phillipe F. X.

doi:10.1007/s10311-010-0294-y

Cited by 13 publications

(3 citation statements)

References 15 publications

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“…The clay fraction, consisting dominantly of organo-clay complexes, was subjected to a Soxhlet-extraction procedure using methanol and dichloromethane in order to obtain the extractable or free fraction of organo-clay-related 353-NP. More detailed information on the sample procedure has been published recently (Riefer et al 2010). …”

Section: Particle Size Fractionation and Extraction Of Organo-clay Comentioning

confidence: 99%

First evidence for a stereoselective incorporation of nonylphenol diastereomers in soil-derived organo-clay complexes

et al. 2011

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Environmental processes can affect the stereochemical properties of organic pollutants. In particular, biotic processes like microbial transformations or membrane penetration alter the ratios of enantiomers as well as diastereomers. These effects have been intensively used not only in environmental studies but also in medicine, toxicology, pharmacy, and agricultural sciences. However, in order to identify unambiguously biotic-initiated alteration of organic compounds, the knowledge on the stereoselective effect of all relevant processes is mandatory. Therefore, here we report the first evidence for a stereospecific formation of non-extractable residues of a xeniobiotic in a highly relevant soil subfraction, the organo-clay complexes. In this study, soils were spiked with labeled and unlabeled nonylphenol isomer, and incubation experiments were performed to study its long-term incorporation behavior into soil-derived organo-clay complexes under abiotic and biotic conditions. Besides the extractable particle-associated proportion especially the humic fractions comprising the bound residues have been analyzed by GC/ MS. Our results from biotic experiments revealed alterations of the diastereomeric composition of the contaminant in the different soil humic subfractions. A depletion of the first eluting diastereomer as expressed by diastereomeric ratios around 0.6 has been observed for the extractable fraction, whereas the non-extractable proportion was enriched in the first diastereomer (diasteremoric ratio around 1.0). On the contrary, the diastereomeric ratios remained unaffected during the abiotic experiments (diasteremoric ratio around 0.8). These systematic observations give clear evidence that the process of microbial-assisted incorporation of nonylphenol into soil organo-clay complexes is a stereoselective process. To our knowledge, this is the first report on a stereoselective incorporation process of organic substances forming non-extractable residues. Consequently, the formation of non-extractable residues has to be considered in environmental studies dealing with stereoselective analysis of organic pollutants in soils to study their microbial transformation.

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Section: Particle Size Fractionation and Extraction Of Organo-clay Comentioning

confidence: 99%

First evidence for a stereoselective incorporation of nonylphenol diastereomers in soil-derived organo-clay complexes

et al. 2011

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“…In both their neutral and anionic form, they can adsorb onto endo-and exogenous soil organic matter fractions, which are believed to be an important sink for these herbicides in soils [12,74]. According to the literature, 2,4-D and MCPA sorption in soil is significantly correlated with humic acid carbon (HA) [12,41,75], and is even better with the more polar fulvic acid (FA) carbon fraction in the case of MCPA [76]. However, it is also known that the affinity of the anionic MCPA form to SOM is ten times lower than that of neutral MCPA molecules [74].…”

Section: Influence Of L and C Soil Components On The Sorption-desorpt...mentioning

confidence: 99%

Influence of SOM Composition, Clay Minerals, and pH on 2,4-D and MCPA Retention in Peri-Urban Soils

Ćwieląg-Piasecka,

Debicka,

Fleszar

2023

Sustainability

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The use of ionic herbicides in urban and peri-urban areas has serious environmental and health consequences due to their common overapplication and mobility in the soil profile. The specific objective of this study was to evaluate the influence of soil organic matter (SOM) fractions and clay minerals on the retention of 2,4-D and MCPA on loamy sand and loam topsoil materials under the pH range of 3–7. The results obtained indicate their weak, unfavorable, and physical sorption, presumably governed by partitioning. 2,4-D exhibited high affinity for polar SOM fractions as well as to kaolinite and montmorillonite, both present in the studied peri-urban soils. MCPA sorption was mainly related to soil fulvic (FA) and humic acid (HA) content; however, the pesticide was sorbed to a lesser extent than 2,4-D due to its great water solubility. This was reflected in MCPA’s low Koc values (41.33 and 84.21), indicating its very high mobility and leachability in the studied soils. Meanwhile, 2,4-D was moderately mobile in sandy soil while classified as a non-leacher in the loam topsoil material. Both herbicides were preferably retained at a low soil pH (3–4), which, together with soil amendment with exogenous, well-humified organic matter, could minimize the potential health and environmental risks of their application.

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“…16 Recently, we demonstrated that nonextractable residues of a specific nonylphenol isomer were preferentially located in soilderived organo−clay complexes and, in particular, the corresponding humic acid fraction acted as the major sink for this isomer. 17 Furthermore, complementary studies revealed not only a rapid incorporation of the nonylphenol isomer 18 but also an influence of the incorporation process on the stereochemical properties of the contaminant indicating microbial assistance. 19 Following this course of investigations the present study focused on the incorporation processes of the labeled NP isomer in soil-derived organo−clay complexes.…”

Section: ■ Introductionmentioning

confidence: 99%

Incorporation Mechanisms of a Branched Nonylphenol Isomer in Soil-Derived Organo–Clay Complexes during a 180-Day Experiment

Riefer

Klausmeyer

Adams

et al. 2013

Environ. Sci. Technol.

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The incorporation process of a defined (13)C- and (14)C-labeled nonylphenol isomer (4-(3,5-dimethylhept-3-yl)phenol) into soil-derived organo-clay complexes was investigated. Isolated organo-clay complexes were separated into humic subfractions. Noninvasive ((13)C-CP/MAS NMR) and invasive methods (sequential chemical degradation, pyrolysis) were applied to obtain detailed information about the mode of incorporation, chemical structure, and change of the incorporation character of nonextractable residues in course of incubation. (13)C-CP/MAS NMR measurements of humic acids revealed an increasing incorporation of phenolic compounds during the experimental time which was referred to residues of the introduced (13)C-labeled NP isomer. Detailed investigations by means of sequential chemical degradation indicated a predominant incorporation of nonextractable NP isomer residues via reversible ester (amide) bonds. In course of time, the amount of releasable compounds decreased, pointing to altering processes which affected the mode of incorporation. BBr3-treatment, RuO4 oxidation, and thermochemolysis released only low portions of nonextractable radioactivity giving evidence of strongly incorporated residues. With the comprehensive application of complementary methods (e.g., humic matter fractionation, (13)C-CP/MAS NMR, sequential chemical degradation) it was possible to provide a comparatively detailed insight into the incorporation behavior of the applied NP isomer.

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Rapid incorporation and short-term distribution of a nonylphenol isomer and the herbicide MCPA in soil-derived organo-clay complexes

Cited by 13 publications

References 15 publications

First evidence for a stereoselective incorporation of nonylphenol diastereomers in soil-derived organo-clay complexes

First evidence for a stereoselective incorporation of nonylphenol diastereomers in soil-derived organo-clay complexes

Influence of SOM Composition, Clay Minerals, and pH on 2,4-D and MCPA Retention in Peri-Urban Soils

Incorporation Mechanisms of a Branched Nonylphenol Isomer in Soil-Derived Organo–Clay Complexes during a 180-Day Experiment

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