Changes in enantiomeric fraction as evidence of natural attenuation of mecoprop in a limestone aquifer

Natural attenuation of the chiral pesticide mecoprop [2-(2-methyl-4-chlorophenoxy)propionic acid] has been studied by determining changes in its enantiomeric fraction in different redox environments down gradient of a landfill in the Lincolnshire Limestone. Previous studies have shown that mecoprop degrades predominantly aerobically and that differences in the biological behaviour of the two enantiomers will change their relative proportions during biodegradation. Originally deposited as a racemic mixture, there has been no change in the enantiomeric fraction in the most polluted part of the landfill plume where conditions are sulphate reducing/methanogenic. In the nitrate-reducing zone, the proportion of (S)-mecoprop increases, suggesting preferential degradation of (R)-mecoprop; while in the aerobic zone, the proportion of (R)-mecoprop increases, suggesting faster degradation of (S)-mecoprop. Mecoprop persistence in the confined Lincolnshire Limestone further downdip is explained by inhibition of degradation in sulphate-reducing conditions, which develop naturally. Laboratory microcosm experiments using up to 10 mg l(-1) of mecoprop confirm these inferences and show that under aerobic conditions, (S)-mecoprop and (R)-mecoprop degrade with zero-order kinetics at rates of 1.90 and 1.32 mg l(-1) day(-1), respectively. Under nitrate-reducing conditions (S)-mecoprop does not degrade, but (R)-mecoprop degrades with zero-order kinetics at 0.65 mg l(-1) day(-1) to produce a stoichiometric equivalent amount of 4-chloro-2-methylphenol. This metabolite only degrades when the (R)-mecoprop has disappeared. The addition of nitrate to a dormant iron-reducing microcosm devoid of nitrate stimulated anaerobic degradation of (R)-mecoprop after a lag period of 21 days. There was no evidence for enantiomeric inversion. The study demonstrates the sensitivity of changes in enantiomeric fraction for detecting natural attenuation, and reveals subtle differences in mecoprop degradation in different redox environments within the Lincolnshire Limestone aquifer.     

Comparative toxic and genotoxic effects of chloroacetanilides,formamidines and their degradation products on Vibrio fischeri and Chironomus riparius

Toxic and genotoxic effects of alachlor, metolachlor, amitraz, chlordimeform, their respective environmentally stable degradation products 2,6-diethylaniline, 2-ethyl-4-methylaniline, 2,4-dimethylaniline, and two other related compounds, 3,4-dichloroaniline and aniline were compared. Acute toxicity tests with Chironomus riparius (96 h) and Vibrio fischeri (Microtox) and genotoxicity tests with a dark mutant of V. fischeri (Mutato) were carried out. Our results demonstrate that toxicity and genotoxicity of the pesticides are retained upon degradation to their alkyl-aniline metabolites. In the case of the herbicides alachlor and metolachlor, the toxicity to V. fischeri was enhanced upon degradation. Narcosis alone explains toxicity of the compounds to the midge, but not so for the bacteria suggesting a disparity in the selectivity of the test systems. All compounds showed direct genotoxicity in the Vibrio test. but amitraz and its metabolite were genotoxic at concentrations 10(3)-10(5) lower than all the other compounds. The observations indicate that stable aniline degradation products of the pesticides may contribute considerably to environmental risks of pesticides application and that genotoxic effects may arise upon degradation of pesticides.     

Degradation and leaching of the herbicides metolachlor and diuron: a case study in an area of Northern Italy

In this work the degradation of the herbicides metolachlor, diuron, monuron and of the metabolites 2-ethyl-6-methylaniline (EMA), and 3,4-dichloroaniline (DCA) was assessed in laboratory experiments on microbiologically active and sterilized soils. Their leaching potentials were calculated, using Gustafson's equation, by determining their mobility (as Koc) and persistence (expressed as DT50). Lysimeter experiments were also conducted to assess the actual leaching of the studied herbicides in a cereal crop tillage area vulnerable to groundwater contamination. The data obtained from the field were compared to the laboratory results. Moreover, some compounds of particular concern were searched for in the groundwater located near the experimental area in order to evaluate actual contamination and to test the reliability of the leaching potential. The GUS index, computed on data from microbiologically active soil, shows monuron as a leacher compound, EMA and DCA as non-leachers, metolachlor and diuron as transient ones. The presence of metolachlor in the groundwater monitored, even at concentrations up to 0.1 mug/l, confirms the possibility that transient compounds can be leached if microbial activity has not completely occurred in active surface soil.     

Enantioselective separation and determination of single nonylphenol isomers

It has recently become clear that an isomer specific view of technical 4-nonylphenol (NP) is absolutely necessary for the evaluation of the biological behavior of NP, raising additional questions concerning enantiomer specific effects. For the first time, in this study enantioselective HPLC was applied to enantiomeric separation of chiral NP isomers. A semipreparative separation of two NP isomers could be achieved. A GC-MS method has been developed for the simultaneous detection of three chiral NP isomers in water samples. Investigation of influent and effluent samples from a wastewater treatment plant in Germany indicated that enantioselective degradation could occur in the environment. In one examined influent, an enantiomer ratio of 1.7 for two different isomers was determined.     

Enantioselective toxicokinetics study of the bioaccumulation and elimination of α-hexachlorocyclohexane in loaches (Misgurnus anguillicaudatus) and its environmental implications

The enantioselective bioaccumulation and elimination of α-hexachlorocyclohexane (α-HCH) in loaches (Misgurnus anguillicaudatus) were studied for the first time. Valid chiral residue analysis methods for α-HCH enantiomers in water and loach samples were established using gas chromatography coupled with electron capture detector and a BGB-172 chiral column. A rapid accumulation process was found during the 39-d bioaccumulation experiment. The α-HCH in loaches reached its maximum on the fourth day, after which it fluctuated slightly, reflecting a balance between elimination and reuptake. The maximum bioaccumulation factor was 728 at the 10 μg L^?1 exposure level. The enantiomeric fraction (EF) values showed that the bioaccumulation was enantioselective with enantioenrichment of (+)-α-HCH in the loaches. The elimination experiment indicated that the degradation kinetics of α-HCH fitted a typical first-order kinetics model, and the half-life was about 5 d. Significant enantioselectivity was observed during the elimination process, with the EFs declining from higher than 0.5–0.39, suggesting (+)-α-HCH is preferentially biotransformed than (?)-α-HCH in loaches. The results reveal a high capacity for α-HCH bioconcentration by loaches and that biotransformation is the main route of decontamination.     

Enantioselective biodegradation of mecoprop in aerobic and anaerobic microcosms

Natural attenuation of mecoprop has been studied by determining changes in enantiomeric fraction in different redox environments down gradient from a landfill in the Lincolnshire limestone. Such changes could be due to differential metabolism of the enantiomers, or enantiomeric inversion. In order to confirm the processes occurring in the field, microcosm experiments were undertaken using limestone acclimatised in different redox zones. No biodegradation was observed in the methanogenic, sulphate-reducing or iron-reducing microcosms. In the nitrate-reducing microcosm (S)-mecoprop did not degrade but (R)-mecoprop degraded with zero order kinetics at 0.65 mg l(-1)day(-1) to produce a stoichiometric equivalent amount of 4-chloro-2-methylphenol. This metabolite only degraded when the (R)-mecoprop disappeared. In aerobic conditions (S)- and (R)-mecoprop degraded with zero order kinetics at rates of 1.90 and 1.32 mg l(-1)day(-1) respectively. The addition of nitrate to dormant iron-reducing microcosms devoid of nitrate stimulated anaerobic degradation of (R)-mecoprop after a lag period of about 20 days and was associated with the production of 4-chloro-2-methylphenol. Nitrate addition to sulphate-reducing/methanogenic microcosms did not stimulate mecoprop degradation. However, the added nitrate was completely utilised in oxidising sulphide to sulphate. There was no evidence for enantiomeric inversion. The study reveals new evidence for fast enantioselective degradation of (R)-mecoprop under nitrate-reducing conditions.     

Detection of methylquinoline transformation products in microcosm experiments and in tar oil contaminated groundwater using LC-NMR

N-heterocyclic compounds are known pollutants at tar oil contaminated sites. Here we report the degradation of methyl-, and hydroxy-methyl-substituted quinolines under nitrate-, sulfate- and iron-reducing conditions in microcosms with aquifer material of a former coke manufacturing site. Comparison of degradation potential and rate under different redox conditions revealed highest degradation activities under sulfate-reducing conditions, the prevailing conditions in the field. Metabolites of methylquinolines, with the exception of 2-methylquinolines, were formed in high amounts in the microcosms and could be identified by ¹H NMR spectroscopy as 2(1H)-quinolinone analogues. 4-Methyl-, 6-methyl-, and 7-methyl-3,4-dihydro-2(1H)-quinolinone, the hydrogenated metabolites in the degradation of quinoline compounds, were identified by high resolution LC-MS. Metabolites of methylquinolines showed persistence, although for the first time a transformation of 4-methylquinoline and its metabolite 4-methyl-2(1H)-quinolinone is described. The relevance of the identified metabolites is supported by the detection of a broad spectrum of them in groundwater of the field site using LC-NMR technique. LC-NMR allowed the differentiation of isomers and identification without reference compounds. A variety of methylated 2(1H)-quinolinones, as well as methyl-3,4-dihydro-2(1H)-quinolinone isomers were not identified before in groundwater.     

Degradation dynamics,residues and risk assessment of Dufulin enantiomers in corn plants and corn by LC/MS/MS

ABSTRACT

The degradation dynamics and terminal residues of dufulin enantiomers were investigated in two typical corn plants. A convenient and precise chiral method by high-performance liquid chromatography coupled with tandem triple quadrupole mass spectrometry (HPLC/MS/MS) using a Chiralpak IC column was developed and validated for measuring dufulin enantiomers in corn plants and corn. The two enantiomers of dufulin quickly dissipated in the corn plant, and no noticeable stereoselectivity was observed during degradation or in the final residues. After 30% rac-dufulin wettable powder with a 1- to 1.5-fold dose of the recommended value was sprayed two to three times on corn plants, the residue levels of S-(+)-dufulin and R-(-)-dufulin in corn from both sites were lower than or equal to 0.0520 mg kg^–1 on days 7, 14 and 21 after the last application. The dietary risk assessment indicated that dufulin did not exhibit obvious dietary health risks in corn samples when good agricultural practices were implemented. The findings from this study may be used to better understand the chiral profiles of dufulin in the environment and the effect of dufulin residues in corn on health.     

Chiral profiling of azole antifungals in municipal wastewater and recipient rivers of the Pearl River Delta, China

Enantiomeric compositions and fractions (EFs) of three chiral imidazole (econazole, ketoconazole, and miconazole) and one chiral triazole (tebuconazole) antifungals were investigated in wastewater, river water, and bed sediment of the Pearl River Delta, South China. The imidazole pharmaceuticals in the untreated wastewater were racemic to weakly nonracemic (EFs of 0.450–0.530) and showed weak enantioselectivity during treatment in the sewage treatment plant. The EFs of the dissolved azole antifungals were usually different from those of the sorbed azoles in the suspended particulate matter, suggesting different behaviors for the enantiomers of the chiral azole antifungals in the dissolved and particulate phases of the wastewater. The azole antifungals were widely present in the rivers. The bed sediment was a sink for the imidazole antifungals. The imidazoles were prevalently racemic, whereas tebuconazole was widely nonracemic in the rivers. Seasonal effects were observed on distribution and chirality of the azole antifungals. Concentrations of the azole antifungals in the river water were relatively higher in winter than in spring and summer while the EF of miconazole in the river water was higher in summer. The mechanism of enantiomeric behavior of the chiral azole antifungals in the environment warrants further research.     

Acetochlor mineralization and fate of its two major metabolites in two soils under laboratory conditions

The degradation of the herbicide acetochlor, in a neoluvisol and in a calcosol were studied as a function of depth (0-25cm and 25-50cm) and temperature (25 degrees C and 15 degrees C) under controlled laboratory conditions during 58 and 90 days, respectively. The surface and sub-surface soil samples were respectively spiked with 1 and 0.01mgkg(-1) of 14C-acetochlor, the concentrations observed in previous field monitoring. The half-lives (DT50) varied from 1.4 to 14.9 days depending on the soil, temperature and applied concentration. The maximal mineralization (24%) was observed for the surface calcosol at 25 degrees C. The comparison of results obtained for sterilized and non-sterilized soils, the decrease of DT50 with the increase of temperature, the shape of CO2 emissions and the increase of number of aerobic endogenous microflora through the experiment suggested that biological process are dominant in degradation. A particular attention was paid to the formation and dissipation of metabolites ESA (ethanesulphonic acid) and OA (oxanilic acid) during the whole experiment. At 25 degrees C, ESA and OA were observed after three days, but as ESA concentration decreased over time in surface calcosol, it remained constant in surface neoluvisol. A difference in ESA/OA ratio depends on the soil with a predominance of OA in surface neoluvisol and a disappearance of OA in surface calcosol.     

Effects of the antimicrobial agent sulfamethazine on metolachlor persistence and sorption in soil

Recent monitoring investigations have shown that antimicrobial agents used in veterinary medicine can cause non-point source contamination of soils through manure spreading. In the present study, the effect of the antimicrobial agent sulfamethazine (sulfadimidine) on degradation and sorption of the herbicide metolachlor in a sandy loam soil was studied. In soil samples treated with sulfamethazine at two concentrations (15 and 150 microg kg(-1) soil), metolachlor persistence was not different than of that observed in untreated samples. These results were supported by the absence of effects of both sulfamethazine concentration levels on the size of the culturable soil bacteria population. Equilibrating soil samples with metolachlor solutions containing equivalent sulfamethazine concentrations did not lead to any significant effects on metolachlor sorption, suggesting that, under the conditions of the present experiment, sulfamethazine did not affect metolachlor bioavailability in soil. This laboratory investigation showed that concentrations of sulfamethazine in the microg kg(-1) range did not cause significant effects on metolachlor degradation and sorption thus not affecting the main processes ruling its environmental fate in soil.     

Di-n-butyl phthalate degrading endophytic bacterium Bacillus amyloliquefaciens subsp. strain JR20 isolated from garlic chive and its colonization in a leafy vegetable

The bioconcentration and elimination of racemic benalaxyl (BX) in trout liver microsomes and in juvenile rainbow trout (Oncorhynchus mykiss) were investigated to determine whether the fish can bioconcentrate and degrade this fungicide enantioselectively. Both enantiomers of BX were extracted with organic solvents and evaluated using high-performance liquid chromatography. In the microsomes, BX degradation followed first-order kinetics, and the S?(+) enantiomer of BX was eliminated twice as rapidly as the R?(?) enantiomer, resulting in residues enriched for R?(?)?BX. In vivo experiment, chiral analysis showed an obvious selective bioconcentration of BX based on statistically altered enantiomer fractions (EFs) in the fish compared with the values in the water. The R?(?)?BX was initially preferentially bioconcentrated by rainbow trout and then dissipated more slowly than its antipode. The mean half-lives for individual enantiomers were calculated as 31.6 h for R?(?)?BX and 20.3 h for the S?(+)?form. The results of the study showed that the degradation of BX enantiomers was stereoselective in rainbow trout.     

Identification of degradation products of thiram in water, soil and plants using LC-MS technique

In order to evaluate the deleterious effects of exposure to pesticides on a target population, a comprehensive study on their degradation in the various segments of ecosystem under varying environmental conditions is needed. In view of this, a study has been carried out on the metabolic pathways of thiram, a dithiocarbamate fungicide, in a variety of matrices namely water and soil under controlled conditions and plants in field conditions. The identification of degradation products was carried out in samples collected at various time points using LC-MS. The degradation products identified can be rationalized as originating by a variety of processes like hydrolysis, oxidation, N-dealkylation and cyclization. As a result of these processes the presence of some metabolites like dimethyl dithiocarbamate, bis(dimethyl carbamoyl) disulphide, bis(dimethyl dithiocarbamoyl) trisulphide and N-methyl-amino-dithiocarbamoyl sulphide was observed in all the cases. However, some different metabolites were observed with the change in the matrix or its characteristics such as cyclised products 2(N, N-dimethyl amino)thiazoline carboxylic acid and 2-thioxo-4-thiazolidine were observed only in plants. The investigations reflect that degradation initiates with hydrolysis, subsequently oxidation/dealkylation, followed by different types of reactions. The pathways seem to be complex and dependent on the matrices. Dimethyl dithiocarbamate and oxon metabolites, which are more toxic than parent compound, seem to persist for a longer time. Results indicate persistence vis-a-vis toxicity of pesticide and its metabolites and also provide a data bank of metabolites for forensic and epidemiological investigations.     

The stereochemistry of 1,2,5,6,9,10-hexabromocyclododecane and its graphic representation

1,2,5,6,9,10-Hexabromocyclododecane, a widely used additive flame retardant, is produced by bromination of cis,trans,trans-cyclododeca-1,5,9-triene, resulting in a mixture of three enantiomeric pairs of diastereomers. We present here the correct configuration and graphic representation of the six isomers. Recently, the complete separation of all six isomers has been achieved using chiral liquid chromatography.     

Enantioselectivity of racemic metolachlor and S-metolachlor in maize seedlings

Chiral herbicides may have enantioselective effects on plants. In this study, we assessed and compared the enantioselectivity of the chiral herbicides rac-metolachlor and S-metolachlor to maize seedlings. The superoxide dismutase activity (SOD) activity of roots and stem leaves treated by rac-metolachlor was 1.38 and 1.99 times that of roots and stem leaves treated by S-metolachlor. The peroxidase activity (POD) activity of roots and stem leaves was 1.48 and 2.79 times that of roots and stem leaves treated by S-metolachlor, respectively, while the catalase activity (CAT) activity was 4.77 and 8.37 times greater, respectively. The Hill reaction activity of leaves treated by rac-metolachlor were 1.45, 1.33, and 1.14 times those treated by S-metolachlor with treatments of 18.6, 37.2, and 74.4 μM. The differences observed between treatments of rac- and S-metolachlor were significant. Significant differences in maize seedling morphology were also observed between rac- and S-metolachlor treatments. The degradation rate of S-metolachlor in roots was greater than that of rac-metolachlor. The half-lives of rac- and S-metolachlor were 80.6 and 60.3 h at 18.6 μM; 119.5 and 90 h at 37.2 μM; and 169 and 164.8 h at 74.4 μM, respectively. Using the liquid chromatography-mass spectrometry method, hydroxymetolachlor, deschlorometolachlor and deschlorometolachlor propanol were considered to be possible metabolites. We determined the enantioselective toxicity of rac- and S-metolachlor to maize and speculated on the proposed metabolic pathway of metolachlor in maize roots. These results will help to develop an understanding of the proper application of rac- and S-metolachlor in crops, and give some information for environmental safety evaluation of rac- and S-metolachlor.     

Enantioselective determination of persistent and partly degradable toxaphene congeners in high trophic level biota

Enantiomer separation of chiral toxaphene components in biological samples was studied by application of different chiral stationary phases based on modified cyclodextrins. Several pairs of enantiomers were resolved on permethylated beta-cyclodextrin (beta-PMCD), among them 2-endo,3-exo,5-endo,6-exo,8,8,9,10-octachlorobornane (B8-1412), which was not enantiomerically resolved on tert-butyldimethylsilylated beta-cyclodextrin (beta-BSCD). The latter column was applied to determine the enantiomer ratios (ERs) of 2-endo,3-exo,5-endo,6-exo,8,8,10,10-octachlorobornane (B8-1413 or P-26) in brain tissue of three seal species. The ER of B8-1413 (P-26) in brain was virtually racemic as well as those of the two persistent and chiral components of technical chlordane, 1-exo,2,2,4,5,6,7,8,8-octachloro-3a,4,7,7a-tetrahydro-4,7-metha noindane (trans-nonachlor III or MC 6) and 1-exo,2-endo,3-exo,4,5,6,8,8-octachloro-3a,7,7a-tetrahydro-4,7- methanoindane (U82). In contrast, B8-1412 and 2-exo,5,5,8,9,9,10,10-octachlorobornane (B8-2229 or P-44) were significantly enantiomerically enriched in several samples of high trophic level biota. 2,2,5,5,8,9,9,10,10-Nonachlorobornane (B9-1025 or P-62), a chlorobornane metabolisable by seals and the presumable precursor of B8-2229 (P-44), was also enantiomerically enriched in seal blubber. These results confirm the assumption that some less persistent toxaphene components may be significantly degraded in biological samples. Enantioselective gas chromatography provides the information that such a degradation is happening by the characteristic change of the ratio of the two enantiomers in the respective tissues.     

Biodegradation of nicosulfuron by the bacterium Serratia marcescens N80

By enrichment culturing of the sludge collected from the industrial wastewater treatment pond, we isolated a highly efficient nicosulfuron degrading bacterium Serratia marcescens N80. In liquid medium, Serratia marcescens N80 grows using nicosulfuron as the sole nitrogen source, and the optimal temperature, pH values, and inoculation for degradation are 30-35°C, 6.0-7.0, and 3.0% (v/v), respectively. With the initial concentration of 10 mg L?1, the degradation rate is 93.6% in 96 hours; as the initial concentrations are higher than 10 mg L?1, the biodegradation rates decrease as the nicosulfuron concentrations increase; when the concentration is 400 mg L?1, the degradation rate is only 53.1%. Degradation follows the pesticide degradation kinetic equation at concentrations between 5 mg L?1 and 50 mg L?1. Identification of the metabolites by the liquid chromatography/mass spectrometry (LC/MS) indicates that the degradation of nicosulfuron is achieved by breaking the sulfonylurea bridge. The strain N80 also degraded some other sulfonylurea herbicides, including ethametsulfuron, tribenuron-methyl, metsulfuron-methyl, chlorimuron-ethyl,and rimsulfuron.     

Spatial and seasonal variations in atrazine and metolachlor surface water concentrations in Ontario (Canada) using ELISA

Concerns regarding the impacts of pesticides on aquatic species and drinking water sources have increased demands on water quality monitoring programs; however the costs of sample analysis can be prohibitive. In this study we investigated enzyme-linked immunosorbent assay (ELISA) as a cost-effective, high through-put method for measuring pesticide concentrations in surface waters. Seven hundred and thirty-nine samples from 158 locations throughout Ontario were analysed for atrazine and metolachlor from April to October 2007. Concentrations ranged from <0.1 to 3.91 μg L⁻¹ (median = 0.12 μg L⁻¹) for atrazine and from <0.1 to 1.83 μg L⁻¹ (median = 0.09 μg L⁻¹) for metolachlor. Peak concentrations occurred in late spring/early summer, in rural agricultural locations, and decreased over the remainder of the growing season for both herbicides. About 3% of the samples that had ELISA results occurring above the limit of quantification (0.10 μg L⁻¹) were evaluated against gas chromatography-mass spectrometry (GC-MS). Linear regression analysis revealed a R² value of 0.88 and 0.39, for atrazine and metolachlor, respectively. ELISA tended to overestimate concentrations for atrazine and metolachlor, most likely because the ELISA kits also detect their metabolites. Atrazine data suggest that ELISA may be used complementary with GC-MS analysis to enhance the spatial and temporal resolution of a water quality monitoring study. The commercially available metolachlor ELISA kit requires further investigation. ELISA may be used to detect atrazine and metolachlor in surface water samples, but it is not recommended as a quantitative replacement for traditional analytical methods.     

Isolation,identification, and acetochlor-degrading potential of a novel Rhodococcus sp. MZ-3

A new species of Rhodococcus, designated strain MZ-3, which could degrade acetochlor efficiently were isolated and identified. The isolate could degrade and utilize acetochlor as the sole source of carbon, nitrogen, and energy for growth. The optimal conditions for the degradation and growth of MZ-3 were pH 7.0 and 30°C. Under these conditions, this strain could completely degrade 200 mg/L of acetochlor within 12 h of incubation. During the biodegradation process, the enantioselectivity of the strain was investigated using a chiral high-performance liquid chromatography (HPLC) system. However, no obvious enantioselectivities were found. 2-chloro-N-(2-methyl-6-ethylphenyl) acetamide (CMEPA) was detected as the intermediate using liquid chromatography-mass spectrometry (LC-MS) analyses. Our results suggest that strain MZ-3 might be a promising microorganism for the bioremediation of acetochlor-contaminated environments because of its acetochlor-degrading performance.     

Leaching properties of some degradation products of alachlor and metolachlor

Once in soil, pesticides undergo degradation processes that give rise to a complex pattern of metabolites. Those presenting a significant percentage of formation, genotoxic and leaching properties may pose a threat to human health associated with the consumption of drinking water. The aim of this study is to assess the hazard potential of some metabolites that may occur in ground water. 2,6-diethylaniline, 2-chloro-2',6'-diethylacetanilide, 2-hydroxy-2',6'-diethylacetanilide, metabolites of alachlor and 2-ethyl-6-methylaniline, metabolite of metolachlor, were chosen for their genotoxic properties. Under laboratory conditions, these metabolites showed DT50 = 1-5 days and Koc = 45-357. Their leaching potential, calculated according to Gustafson, is very low and, therefore, they should not be regarded as contaminants of ground waters. Aged residue leaching studies as well as preliminary studies on well waters seem to confirm these findings.