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PubMed2001

Photochemical transformation of acifluorfen under laboratory and natural conditions.

Acifluorfen was irradiated in pure water at various excitation wavelengths and pH values. Numerous photoproducts were obtained which were identified by [1H]NMR and/or HPLC-MS/MS. The main reaction pathways were photo-decarboxylation, photo-cleavage of the ether bonding with formation of phenolic compounds, photo-dechlorination and photo-Claisen type rearrangement. Decarboxylation was observed in acidic and neutral media whereas cleavage of the ether bonding dominated in basic media. The photo-Claisen type rearrangement only occurred on excitation at short wavelengths. The quantum yield of photolysis was significantly lower at 313 nm (6.1 x 10(-5)) than at 254 nm (2.0 x 10(-3)). The photoreactivity of acifluorfen was then studied in conditions approaching environmental conditions. Acifluorfen was dissolved in pure water, in water containing humic substances or in a natural water, and exposed to solar light in June at Clermont-Ferrand (latitude 46 degrees N). In pure water, the half-life was estimated at 10 days and photo-decarboxylation accounted for 30% of the conversion. The presence of humic substances (10 mg litre-1) did not affect the rate of photo-transformation. However, the half-life of acifluorfen dissolved in the natural water was only 6.8 days.

Biodegradation, Environmental↗

PubMed1998

Association of Chernobyl-derived 239+240Pu, 241Am, 90Sr and 137Cs with different molecular size fractions of organic matter in the soil solution of two grassland soils.

Radiocesium is normally bound only rather weakly and unspecifically by humic substances, in contrast to the actinides Pu and Am. Recently, however, it was observed that fallout 137Cs in the soil solution from an Of-horizon of a podzol forest soil (slightly decomposed plant material) was associated essentially only with one single size fraction of the humic substances. In deeper soil layers with well humified material (AOh-horizon), radiocesium was associated with all size fractions of the dissolved organic matter (DOM). To examine whether this unexpected behaviour is also observable for DOM isolated from other soils, we determined the association of fallout 137Cs, 90Sr, 238Pu, 239+240Pu and 241Am with various size fractions of DOM from in situ soil solutions isolated from two layers (0-2 cm and 2-5 cm) of two grassland soils (a soddy podzolic soil and a peat soil) within the 10 km zone of the nuclear reactor at Chernobyl (Ukraine). The four size fractions of DOM as obtained by gel filtration of the soil solution were (mean nominal molecular weight in daltons): fraction I: > or = 2000, fraction II: 1300; fraction III: 560, fraction IV: inorganic compounds. The results for the well humified DOM (humus accumulation horizon of podzol, deeper layer of peat soil) showed that Pu and Am are essentially associated with the high molecular weight fractions, while Sr is present only in the 'inorganic' fraction. Radiocesium is found in all the size fractions separated. A quite similar pattern was also found for Pu, Am, and Sr in the soil solution from only slightly decomposed plant material (0-2 cm of peat soil), but not for radiocesium. This radionuclide was again essentially only observable in one single low molecular weight fraction of DOM. The above results thus support our recent observations in the different horizons of a forest podzol mentioned above, even though no reason for the different binding of radiocesium by well humified soil organic matter and by only slightly decomposed plant material can be given at present. The data demonstrate, however, that information on only the total amount of a radionuclide in the soil solution will not be sufficient to interpret or predict its fate adequately in the soil.

Americium↗

PubMed1984

Irradiation conditions required in combined radiation-microbial process for landfill leachate.

A landfill leachate, which contains large amounts of microbially refractory humic substances, was irradiated with 60Co gamma-rays under several conditions and the modification of its biodegradability was examined. The effects of initial pH and dose rate on the modification were found to be insignificant. The apparent effect was observed for the initial concentration of the humic substances. High biochemical oxygen demand (BOD) value was obtained as the initial concentration was higher. As the initial concentration was lower, in contrast, the decreasing rates of total organic carbon (TOC) and chemical oxygen demand (COD) were high. Therefore two possible designs of the combined radiation-microbial processes with and without dilution are proposed. Both processes require only about 30% of the irradiation dose, compared with a simple radiation process.

Biodegradation, Environmental↗

PubMed2004

Photocatalytic remediation of gamma-HCH contaminated soil induced by alpha-Fe2O3 and TiO2.

Heterogeneous photocatalytic degradation of gamma-HCH on soil surfaces was carried out to evaluate the photocatalytic effectiveness of alpha-Fe2O3 and TiO2 toward degrading gamma-HCH on soil surfaces. After being spiked with gamma-HCH, soil samples were loaded with alpha-Fe2O3 or TiO2 and exposed to UV-light irradiation. Different catalyst loads, 0%, 2%, 5%, 7%, and 10% (wt.) alpha-Fe2O3; 0%, 0.5%, 1%, 2: (wt.)TiO2, were tested for up to 7 d irradiation. The effects of soil thickness, acidity, and humic substances were also investigated. The obtained results indicated that the gamma-HCH photodegradation follows the pseudo-first-order kinetics. The addition of alpha-Fe2O3 or TiO2 accelerates the photodegradation of gamma-HCH, while the photodegradation rate decreases when the content of alpha-Fe2O3 exceeds 7% (wt.). The degradation rate increases with the soil pH value. Humic substances inhibit the photocatalytic degradation of gamma-HCH. Pentachlorocyclohexene, tetrachlorocyclohexene, and trichlorobenzene are detected as photodegradation intermediates, which are gradually degraded with the photodegradation evolution.

Catalysis↗

PubMed1999

Degradation of lignite (low-rank coal) by ligninolytic basidiomycetes and their manganese peroxidase system

Ligninolytic basidiomycetes (wood and leaf-litter-decaying fungi) have the ability to degrade low-rank coal (lignite). Extracellular manganese peroxidase is the crucial enzyme in the depolymerization process of both coal-derived humic substances and native coal. The depolymerization of coal by Mn peroxidase is catalysed via chelated Mn(III) acting as a diffusible mediator with a high redox potential and can be enhanced in the presence of additional mediating agents (e.g. glutathione). The depolymerization process results in the formation of a complex mixture of lower-molecular-mass fulvic-acid-like compounds. Experiments using a synthetic 14C-labeled humic acid demonstrated that the Mn peroxidase-catalyzed depolymerization of humic substances was accompanied by a substantial release of carbon dioxide (17%-50% of the initially added radio-activity was released as 14CO2). Mn peroxidase was found to be a highly stable enzyme that remained active for several weeks under reaction conditions in a liquid reaction mixture and even persisted in sterile and native soil from an opencast mining area for some days.

Journal Article↗

PubMed2002

Identification of compound classes in soil and peat fulvic acids as observed by electrospray ionization tandem mass spectrometry.

Soil and peat fulvic acids obtained from the International Humic Substances Society were fractionated by their solubility in methanol and analyzed by electrospray ionization tandem mass spectrometry. Precursor and product ion experiments produced mass spectra that indicated the presence of benzene, phenol, dihydroxy benzene, furan and thiophene carboxylic acids. Standards were used to substantiate the fragmentation patterns observed in the product ion spectra of the fulvic acid samples. This study makes significant progress into the direct identification of individual compounds in humic substances using a non-degradation technique.

Benzopyrans↗

PubMed1991

Chemical reactions of metals with humic material.

Humic substances are chemically very complex materials whose structure and reactions are not fully understood. They are believed to be macromolecules, spanning a wide range of molecular weights, which are formed from quinones and phenolic compounds. They contain a wide variety of functional groups, which may react with metals. Many different physical and chemical procedures have been used to study these interactions, and numerous different reaction mechanisms and products have been postulated. The colloidal properties of humic materials also affects their interactions with metals. Reaction with humic substances profoundly affects the environmental behaviour of metals. Solubility, plant availability and even volatility are all greatly influenced and can be either enhanced or reduced by these reactions.

Journal Article↗

PubMed2001

Phototransformation of propiconazole in aqueous media.

The photolysis of propiconazole in pure water, in water containing humic substances, and in natural water was investigated. The reaction rates were determined, and the main photoproducts were identified with the help of HPLC-mass spectrometry and by NMR. The quantum yield for direct photolysis was 0.11 +/- 0.01 at the maximum of absorption (269 nm). Photocyclization after HCl elimination and photohydrolysis of the cyclized intermediate were the main reaction pathways at 254 nm. By contrast, oxidation prevailed over dechlorination in simulated or natural solar light. Humic substances (10 mg x L(-)(1)) and naturally occurring chromophores contained in natural water enhanced the rate of propiconazole photodegradation in solar light. Half-life in June in Clermont-Ferrand (latitude 46 degrees N) was found to be 85 +/- 10 h in pure water and 60 +/- 10 h in natural water; showing that photodegradation of propiconazole in natural waters involves both direct photolysis and photoinduced reactions.

Fungicides, Industrial↗

PubMed2000

Anaerobic benzene degradation.

Although many studies have indicated that benzene persists under anaerobic conditions in petroleum-contaminated environments, it has recently been documented that benzene can be anaerobically oxidized with most commonly considered electron acceptors for anaerobic respiration. These include: Fe(III), sulfate, nitrate, and possibly humic substances. Benzene can also be converted to methane and carbon dioxide under methanogenic conditions. There is evidence that benzene can be degraded under in situ conditions in petroleum-contaminated aquifers in which either Fe(III) reduction or methane production is the predominant terminal electron-accepting process. Furthermore, evidence from laboratory studies suggests that benzene may be anaerobically degraded in petroleum-contaminated marine sediments under sulfate-reducing conditions. Laboratory studies have suggested that within the Fe(III) reduction zone of petroleum-contaminated aquifers, benzene degradation can be stimulated with the addition of synthetic chelators which make Fe(III) more available for microbial reduction. The addition of humic substances and other compounds that contain quinone moieties can also stimulate anaerobic benzene degradation in laboratory incubations of Fe(III)-reducing aquifer sediments by providing an electron shuttle between Fe(III)-reducing microorganisms and insoluble Fe(III) oxides. Anaerobic benzene degradation in aquifer sediments can be stimulated with the addition of sulfate, but in some instances an inoculum of benzene-oxidizing, sulfate-reducing microorganisms must also be added. In a field trial, sulfate addition to the methanogenic zone of a petroleum-contaminated aquifer stimulated the growth and activity of sulfate-reducing microorganisms and enhanced benzene removal. Molecular phylogenetic studies have provided indications of what microorganisms might be involved in anaerobic benzene degradation in aquifers. The major factor limiting further understanding of anaerobic benzene degradation is the lack of a pure culture of an organism capable of anaerobic benzene degradation.

Bacteria, Anaerobic↗

PubMed2003

In situ trace metal speciation in lake surface waters using DGT, dialysis, and filtration.

In situ measurements of Fe and Mn by dialysis and diffusive gradients in thin-films (DGT) in 5 lakes (pH 4.7-7.5, ionic strength 0.3-5 mmol l(-1)) and Cu and Zn in an acidic and circumneutral lake were compared to results from on site filtration. For the most acidic lake (pH 4.7) all measurements agreed, indicating an absence of colloids and negligible complexation by organic matter. There was little difference in the Mn concentrations measured by the three techniques for any lake, consistent with it being free from complexation. Zn measured by dialysis in circumneutral water was only slightly higher than DGT measurements, appropriate to only partial complexation. Substantial differences between dialysis and DGT for Cu were consistent with complexation by fulvic and humic substances, though not to the extent predicted by the speciation code WHAM. To achieve a good fit it was necessary to adjust the pK for Cu-fulvic binding from 0.8 to 1.3 and to assume that fulvic substances dominated. The presence of low molecular weight strong binding ligands would also be consistent with the data. Differences between the three measurement methods were greatest for Fe, attributable to the presence of large oxyhydroxide colloids, organic complexation and low molecular weight, reactive hydrolysis products. Fe and Mn concentrations measured by DGT on samples returned to the laboratory were much lower than in situ concentrations, illustrating the need for in situ measurements. While use of two in situ techniques provided useful information on the speciation of these natural waters, further refinements are required for unambiguous characterization of the solution. The use of DGT with a more restricted gel that excludes complexes with humic substances should provide complementary information to in situ dialysis.

Dialysis↗

PubMed2004

Photodegradation of pesticides on plant and soil surfaces.

Photodegradation is an abiotic process in the dissipation of pesticides where molecular excitation by absorption of light energy results in various organic reactions, or reactive oxygen species such as OH*, O3, and 1O2 specifically or nonspecifically oxidize the functional groups in a pesticide molecule. In the case of soil photolysis, the heterogeneity of soil together with soil properties varying with meteorological conditions makes photolytic processes difficult to understand. In contrast to solution photolysis, where light is attenuated by solid particles, both absorption and emission profiles of a pesticide are modified through interaction with soil components such as adsorption to clay minerals or solubilization to humic substances. Diffusion of a pesticide molecule results in heterogeneous concentration in soil, and either steric constraint or photoinduced generation of reactive species under the limited mobility sometimes modifies degradation mechanisms. Extensive investigations of meteorological effects on soil moisture and temperature as well as development of an elaborate testing chamber controlling these factors seems to provide better conditions for researchers to examine the photodegradation of pesticides on soil under conditions similar to the real environment. However, the mechanistic analysis of photodegradation has just begun, and there still remain many issues to be clarified. For example, how photoprocesses affect the electronic states of pesticide molecules on soil or how the reactive oxygen species are generated on soil via interaction with clay minerals and humic substances should be investigated in greater detail. From this standpoint, the application of diffuse reflectance spectroscopy and usage or development of various probes to trap intermediate species is highly desired. Furthermore, only limited information is yet available on the reactions of pesticides on soil with atmospheric chemical species. For photodegradation on plants, the importance of an emission spectrum of the light source near its surface was clarified. Most photochemical information comes from photolysis in organic solvents or on glass surfaces and/or plant metabolism studies. Epicuticular waxes may be approximated by long-chain hydrocarbons as a very viscous liquid or solid, but the existing form of pesticide molecules in waxes is still obscure. Either coexistence of formulation agents or steric constraint in the rigid medium would cause a change of molecular excitation, deactivation, and photodegradation mechanisms, which should be further investigated to understand the dissipation profiles of a pesticide in or on crops in the field. A thin-layer system with a coat of epicuticular waxes extracted from leaves or isolated cuticles has been utilized as a model, but its application has been very limited. There appear to be gaps in our knowledge about the surface chemistry and photochemistry of pesticides in both rigid media and plant metabolism. Photodegradation studies, for example, by using these models to eliminate contribution from metabolic conversion as much as possible, should be extensively conducted in conjunction with wax chemistry, with the controlling factors being clarified. As with soil surfaces, the effects of atmospheric oxidants should also be investigated. Based on this knowledge, new methods of kinetic analysis or a device simulating the fate of pesticides on these surfaces could be more rationally developed. Concerning soil photolysis, detailed mechanistic analysis of the mobility and fate of pesticides together with volatilization from soil surfaces has been initiated and its spatial distribution with time has been simulated with reasonable precision on a laboratory scale. Although mechanistic analyses have been conducted on penetration of pesticides through cuticular waxes, its combination with photodegradation to simulate the real environment is awaiting further investigation.

Humans↗

PubMed2006

Aged raw landfill leachate: membrane fractionation, O3 only and O3/H2O2 oxidation, and molecular size distribution analysis.

Large molecular refractory organic compounds (i.e., humic substances) were the major chemical oxygen demand (COD) components of aged raw landfill leachate. To investigate the behaviours of the large molecular refractory organic compounds when they were subjected to oxidation with ozone only (O3 only) and ozone combined with hydrogen peroxide (O3/H2O2), the aged raw landfill leachate first was filtered with 0.8 and 0.45 microm pore size filters in series, then was sequentially fractionated with 10,000 MWCO; 5000 MWCO; and 1000 MWCO membranes, and four samples were formed: 0.45 microm-10,000 Da; 10,000-5000 Da; 5000-1000 Da; and < 1000 Da. Mass distribution profiles of COD, 5-day biochemical oxygen demand (BOD5), colour and metals in the aged raw leachate were developed through mass balance. After membrane fractionation of the aged raw leachate, the metals were fractionated with the humic substances. Each fractionated sample as well as the aged raw leachate was oxidised with O3 only and O3/H2O2. The H2O2 enhanced the reduction of COD and colour; while, the BOD5 after O3 only was always higher than that of O3/H2O2. The addition of H2O2 improved the peak reduction of large molecules, but the effects of H2O2 on the fractions of 10,000-5000 Da and 5000-1000 Da were likely insignificant, which is in accordance with the COD results. No correlation was found between the BOD5 increase and the area of new peak formed after oxidation. However, the BOD5 of each sample after oxidation with O3 only was the logarithmic function of its total peak area.

Environmental Pollution↗

PubMed2002

Organic nitrogen in geomacromolecules: insights on speciation and transformation with K-edge XANES spectroscopy.

Organic nitrogen incorporated into geomacromolecules (e.g., humic substances, kerogen) represents a major reservoir of nitrogen on the earth's surface, accounting for more than 90% of the total nitrogen in soils, sediments, and aquatic environments. Its primary source is biochemical nitrogen from dead plant and animal residues (predominantly proteinaceous substances), which undergo a complex series of transformations, mediated by microbes and abiotic processes, ultimately resulting in the incorporation of the nonmineralized fraction into geomacromolecules. Simultaneously,the biochemical N is thought to be extensively altered structurally, forming more stable structures (such as heterocyclic forms), although the type of changes in chemical speciation, their timing, and mechanisms are not clear. It is important to have this knowledge because the type of N formed influences not only its reactivity and fate (e.g., the release of bioavailable N in soils) but also the physical and chemical characteristics of the associated macromolecular organic matter. We used nitrogen K-edge XANES spectroscopy (a selective, sensitive, and nondestructive method) to gain new insights into the speciation of this macromolecular nitrogen. Our results verified amide N as being the dominant type in humic substances and sediments but revealed that pyridinic N also is a significant component of the total N (approximately 20-30%), with a subfraction consisting of its oxidized derivatives. An unidentified form of highly oxidized N was present mainly in sediments. While amide N represents residues of original biochemical molecules, pyridinic N probably is generated abiotically. Our results imply that the abiotic formation of pyridinic N sets in during the early stages of organic matter transformations thereby stabilizing organic N, although such processes generating heterocyclic structures may continue much longer.

Biotransformation↗

PubMed1995

Prevalence of goiters in children residing in Tung-Lo Township, Taiwan.

This study investigated school children in the Tung-Lo Township in central Taiwan to determine the prevalence of goiters compared to other areas of Taiwan and to elucidate the possible etiology. All children attending elementary schools in Tung-Lo were examined for thyroid enlargement by neck palpation, as recommended by the World Health Organization. Thyroid antibodies and thyroid hormones were determined in children with goiters, and in normal age- and sex-matched controls. Additionally, analysis of drinking water for humic substances was done by fluorospectrophotometry. In total, 1,823 school children were examined (965 boys and 858 girls). Of these, 174 (9.5%) were found to have a goiter of grade I or above. The prevalence was higher than our recent surveys in other areas of Taiwan (2.6%-8.8%). Goiter prevalence in school children residing in hill regions (12.9%), mainly dependent on underground water for drinking, was higher than that of school children residing in plain regions (8.2%), who depend on tap water for drinking. The quality of drinking water bore a close relationship to the prevalence of goiter. From the ratio of T3/T4 in this study, and a study of urinary iodine excretion done by others, it is concluded that goiters in Tung-Lo are not related to iodine deficiency. There was no statistically significant correlation between the relative fluorescence intensity of humic substances and the prevalence of goiter. The results of this study suggest that the higher prevalence of goiter in children living in Tung-Lo, an oil-bearing area, may be related to the quality of drinking water.

Child↗

PubMed1988

Comparative analysis of the chemical composition of mixed and pure cultures of green algae and their decomposed residues by C nuclear magnetic resonance spectroscopy.

It is known that macromolecular organic matter in aquatic environments, i.e., humic substances, is highly aliphatic. These aliphatic macromolecules, predominantly paraffinic in structure, are prevalent in marine and lacustrine sediments and are believed to originate from algae or bacteria. A comparative study of mixed and pure cultures of green algae and their decomposed residues was performed by using solid-state C nuclear magnetic resonance spectroscopy as the primary analytical method. Results obtained in this study confirm the presence of components that are chemically refractory and that are defined as alghumin and hydrolyzed alghumin. These were detected in heterogeneous, homogeneous, and axenic biomasses composed of several genera of Chlorophyta. Although the chemical composition of algal biomass varied with culture conditions, the chemical structure of the alghumin and hydrolyzed alghumin, demonstrated by C nuclear magnetic resonance spectroscopy appeared to be constant for members of the Chlorophyta examined in this study. The alghumin was dominated by carbohydrate-carbon, with minor amounts of amide or carboxyl carbon and paraffinic carbon, the latter surviving strong hydrolysis by 6 N HCI (hydrolyzed alghumin). Bacterial decomposition of heterogeneous algal biomass labeled with C was conducted under both aerobic and anaerobic conditions to determine chemical structure and stability of the refractory material. The refractory fraction ranged from 33% in aerobic to 44% in anaerobic cultures. The refractory fraction recovered from either aerobic or anaerobic degradation comprised 40% alghumin, which represented an enrichment by 10% relative to the proportion of alghumin derived from whole cells of algae. The paraffinic component in the hydrolyzed alghumin of whole algal cells was found to be 1.8% and increased to 5.1 and 6.9% after aerobic and anaerobic bacterial degradation, respectively. It is concluded that members of the Chlorophyta contain a common insoluble structure composed of paraffinic carbon that is resistant to chemical and bacterial degradation under conditions used in this study. The paraffinic structure is identical to those constituting humin of aquatic origin. Thus, alga-derived macromolecular compounds deposited in aquatic environments (alghumin) probably contribute to sedimentary humic substances.

Journal Article↗

PubMed2003

Kinetic investigation of Eu(III)-humate interactions by ion exchange resins.

The kinetic stability of radionuclides bound to aqueous colloids is a determining factor in their migration from a radioactive waste repository. The cation exchangers Chelex-100, Dowex 50Wx4, and Cellphos (cellulose phosphate) have been shown a promising tool for kinetic investigations. This study assesses the applicability of different exchange resins for Eu humate dissociation kinetics investigations. All resins were found to produce satisfactory results. A systematic study of parameters affecting the dissociation rates of Eu(III) humate complexes was performed. A set of purified humic substances was found to behave in the same way. However, unpurified Aldrich humic acid showed significant differences.

Europium↗

PubMed2005

Characterization of natural organic matter (NOM) derived from sewage sludge compost. Part 2: multivariate techniques in the study of compost maturation.

This study presents the results of chemometric data analysis which describes the maturation of sewage sludge compost. The compost was characterized at different stages of maturation by various chemical and spectroscopic parameters including carbon and nitrogen content, humic substances content, UV-Vis and 13C NMR. The data set of compost characteristics was analyzed using multivariate methods: cluster analysis (CA) and principal component analysis (PCA). The results enabled the determination of three groups of compost samples at different stages of maturation that correspond to three stages of composting: (i) domination of rapid decomposition of non-humic, easily biodegradable organic matter, (ii) domination of organic matter humification and formation of polycondensed, humic-like substances (the next 2 weeks), (iii) stabilization of transformed organic material and weak microbial activity. The multivariate techniques also enabled the identification of main parameters that change during different stages of composting the most.

Algorithms↗

PubMed2005

Copper and other trace elements strongly bound to humic acids along sediment cores in the Ross Sea, Antarctica.

Marine sediment cores sampled in three different areas, during the 1997/98 Italian Antarctic Expedition, were studied. The cores (40 cm) were immediately subdivided into 13 or 14 layers (2-4 cm) in order to obtain a high-depth resolution in the metal content and humic substance analyses. The results obtained for the amount of metals strongly bound to humic acids showed the following order: Cu >> Zn >> Co > As >or= Mn. The fraction of Cu, Zn and As bound to humic acid (microg g(-1) of HA) increases in the first 10-12 cm of cores, then a decrease is observed. This observation could be related both to the presence of a mobile fraction of metals in sediments successively bound to humic acids and to different structural features showed by humic acids along the cores, due to transformation processes. For the other metals a variable pattern along the cores was found.

Antarctic Regions↗