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Environmental fate & pathways

Biodegradation in water: screening tests

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Reference
Endpoint:
biodegradation in water: ready biodegradability
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Data is from computational model developed by USEPA
Qualifier:
according to guideline
Guideline:
other: Modeling database
Principles of method if other than guideline:
The Biodegradation Probability Program (BIOWIN) estimates the probability for the rapid aerobic biodegradation of an organic chemical in the presence of mixed populations of environmental microorganisms .The model is part of the EpiSuite program of the US-EPA. Estimations are made with BIOWIN version 4.10. Estimates are based upon fragment constants that were developed using multiple linear and non-linear regression analyses. Experimental biodegradation data for the multiple linear and non-linear regressions were obtained from Syracuse Research Corporation's (SRC) data base of evaluated biodegradation data (Howard et. al., 1987). This version (v4.10) designates the models as follows (see also Boethling et al. 2003):
Biowin1 = linear probability model
Biowin2 = nonlinear probability model
Biowin3 = expert survey ultimate biodegradation model
Biowin4 = expert survey primary biodegradation model
Biowin5 = MITI linear model
Biowin6 = MITI nonlinear model
Biowin7 = anaerobic biodegradation model
GLP compliance:
not specified
Specific details on test material used for the study:
- Name of test material : chromium(3+) ion hydrogen bis(1-(3-chlorophenyl)-4-[(E)-2-(5-methanesulfonyl-2-oxidophenyl)diazen -1-yl]-3-methyl-1H-pyrazol-5-olate)
- Common name : Hydrogen bis[2-(3-chlorophenyl)-2,4-dihydro-4-[[2-hydroxy-5-mesylphenyl]azo]-5-methyl-3H-pyrazol-3-onato(2-)]chromate(1-)
- Molecular formula : C34H27Cl2CrN8O8S2
- Molecular weight : 862.669 g/mol
- Smiles notation : c1(cccc(c1)Cl)N1N=C([C@@-](C1=O)\N=N\c1c(ccc(S(C)(=O)=O)c1)[O-])C.[Cr+3].O=S(c1cc(c(cc1)[O-])\N=N\[C@@-]1C(=NN(C1=O)c1cc(ccc1)Cl)C)(C)=O
- InChl : 1S/2C17H14ClN4O4S.Cr/c2*1-10-16(17(24)22(21-10)12-5-3-4-11(18)8-12)20-19-14-9-13(27(2,25)26)6-7-15(14)23;/h2*3-9,23H,1-2H3;/q2*-1;+3/p-1/b2*20-19+;
- Substance type : Organic
- Physical state : Solid
Oxygen conditions:
other: aerobic (Biowin 1-6) and anaerobic (Biowin 7)
Inoculum or test system:
other: mixed populations of environmental microorganisms
Details on study design:
Using the computer tool BIOWIN v4.10 by US-EPA (EPIWIN) the aerobic as well as the anaerobic biodegradability of the test material can be estimated. The follwoing seven different models are used by the tool: Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI LInear Model, MITI Non-Linear Model and Anaerobic Model (calles Biowin 1-7, respectively). Due to this results the overall prediction of readily biodegradability is done for the desired chemical.

Biowin 1 and 2, are intended to convey a general indication of biodegradability under aerobic conditions, and not for any particular medium.
Biowin 1 (Linear model)
The fast biodegradation probability for any compound is calculated by summing, for all the fragments present in that compound, the fragment coefficient multiplied by the number of instances of the fragment in the compound (for MW, the value of that parameter is multiplied by its coefficient), and then adding this summation to the equation constant which is 0.7475. The summed values for each fragment coefficient multiplied by the number of instances appear in the "VALUE" column of the linear results screen.

Biowin 2 (Non-linear model)
Calculation of the fast biodegradation probability for any compound begins by summing, for all the fragments present in that compound, the fragment coefficient multiplied by the number of instances of the fragment in the compound (for MW, the value of that parameter is multiplied by its coefficient), then adding this summation to the equation constant which is 3.0087. The summed values for each fragment coefficient multiplied by the number of instances appear in the "VALUE" column of the non-linear results screen. The non-linear fast biodegradation probability is then calculated from the logistic equation as follows, where total = 3.0087 + the summation as described above:

Biowin 3 and 4 yield estimates for the time required to achieve complete ultimate and primary biodegradation in a typical or "evaluative" aquatic environment.

Biowin 5 and 6 are predictive models for assessing a compound’s biodegradability in the Japanese MITI (Ministry of International Trade and Industry) ready biodegradation test; i.e. OECD 301C. These models use an approach similar to that used to develop Biowin1 and 2. This protocol for determining ready biodegradability is among six officially approved as ready biodegradability test guidelines of the OECD (Organization for Economic Cooperation and Development). A total dataset of 884 chemicals was compiled to derive the fragment probability values that are applied in this MITI Biodegradability method. The dataset consists of 385 chemical that were critically evaluated as "readily degradable" and 499 chemicals that were critically evaluated as "not readily biodegradable".

Biowin 7, the anaerobic biodegradation model, is the most recent. As for the other Biowin models, multiple (linear) regression against molecular fragments was used to develop the model, which predicts probability of rapid degradation in the "serum bottle" anaerobic biodegradation screening test. This endpoint is assumed to be predictive of degradation in a typical anaerobic digester. Biowin7 estimates the probability of fast biodegradation under methanogenic anaerobic conditions; specifically, under the conditions of the "serum bottle" anaerobic biodegradation screening test (Meylan et al. 2007). A total of 169 compounds with serum bottle test data were identified for use in model development.

Out of seven different Biowin models, Biowin model 3 and 4 will help in estimating biodgeradability of the test chemical which was described as below-

Ultimate Biodegradation Timeframe and Primary Biodegradation Timeframe (Biowin 3 and 4)
These two models estimate the time required for "complete" ultimate and primary biodegradation.  Primary biodegradation is the transformation of a parent compound to an initial metabolite.  Ultimate biodegradation is the transformation of a parent compound to carbon dioxide and water, mineral oxides of any other elements present in the test compound, and new cell material. Then the rating was given to each model, which indicates the time required to achieve ultimate and primary biodegradation in a typical or "evaluative" aquatic environment. The ratings for each compound were averaged to obtain a single value for modeling.  The ultimate or primary rating of a compound is calculated by summing, for all the fragments present in that compound.
Key result
Remarks on result:
other: not readily biodegradable as estimated by BIOWIN model
Validity criteria fulfilled:
not specified
Interpretation of results:
not readily biodegradable
Conclusions:
The biodegradability of the substance was calculated using seven different Biowin 1-7 models of the BIOWIN v4.10 software. The results indicate that the test chemical chromium(3+) ion hydrogen bis(1-(3-chlorophenyl)-4-[(E)-2-(5-methanesulfonyl-2-oxidophenyl)diazen -1-yl]-3-methyl-1H-pyrazol-5-olate) is expected to be not readily biodegradable.
Executive summary:

Estimation Programs Interface Suite (EPI suite, 2018) was run to predict the biodegradation potential of the test compound  chromium(3+) ion hydrogen bis(1 -(3 -chlorophenyl)-4 -[(E)-2 -(5 -methanesulfonyl-2 -oxidophenyl)diazen -1 -yl]-3 -methyl-1H-pyrazol-5 -olate) (CAS no. 71598 -35 -1) in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical chromium(3+) ion hydrogen bis(1-(3-chlorophenyl)-4-[(E)-2-(5-methanesulfonyl-2-oxidophenyl)diazen -1-yl]-3-methyl-1H-pyrazol-5-olate) is expected to be not readily biodegradable.

Description of key information

Estimation Programs Interface Suite (EPI suite, 2018) was run to predict the biodegradation potential of the test compound  chromium(3+) ion hydrogen bis(1 -(3 -chlorophenyl)-4 -[(E)-2 -(5 -methanesulfonyl-2 -oxidophenyl)diazen -1 -yl]-3 -methyl-1H-pyrazol-5 -olate) (CAS no. 71598 -35 -1) in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical chromium(3+) ion hydrogen bis(1-(3-chlorophenyl)-4-[(E)-2-(5-methanesulfonyl-2-oxidophenyl)diazen -1-yl]-3-methyl-1H-pyrazol-5-olate) is expected to be not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:
under test conditions no biodegradation observed

Additional information

Predicted data for the target compound chromium(3 +) ion hydrogen bis(1 -(3 -chlorophenyl)-4 -[(E)-2 -(5 -methanesulfonyl-2 -oxidophenyl)diazen -1 -yl]-3 -methyl-1H-pyrazol-5 -olate) (CAS No. 71598 -35 -1) and various supporting weight of evidence studies for its structurally and functionally similar read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction using the Estimation Programs Interface Suite (EPI suite, 2018), the biodegradation potential of the test compoundchromium(3+) ion hydrogen bis(1-(3-chlorophenyl)-4-[(E)-2-(5-methanesulfonyl-2-oxidophenyl)diazen -1-yl]-3-methyl-1H-pyrazol-5-olate)(CAS No. 71598-35-1) in the presence of mixed populations of environmental microorganisms was estimated.The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemicalchromium(3+) ion hydrogen bis(1-(3-chlorophenyl)-4-[(E)-2-(5-methanesulfonyl-2-oxidophenyl)diazen -1-yl]-3-methyl-1H-pyrazol-5-olate)is expected to be not readily biodegradable.

 

In a supporting study from peer reviewed journal (D. Brown, et. al; 1987) for the read across chemical Acid yellow 25 (CAS no. 6359-85-9), biodegradation study was carried out to determine the biodegradability rate of the test substance Acid yellow 25 (CAS no. 6359-85-9). Activated sludge was used as an inoculum and the study was performed under anaerobic conditions at a temperature of 35°C for a period of 56 days. Samples of the aqueous phase were analyzed either qualitatively or quantitatively by an appropriate chromatographic method for the presence of certain of the expected aromatic amine metabolites. The percentage degradation of test substance Acid yellow 25 was determined to be 57% by appropriate chromatography method in 56 days. The metabolites identified by the appropriate chromatographic method were 3 -amino-6 -methylbenzene- N-phenylsulphonamid and 4 -amino-3 -methy1 -1 -[4'-sulphophenyl)pyrazolone, respectively. Thus, based on percentage degradation, chemical Acid yellow 25 is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for evaluating the percentage biodegradation of read across chemical Disodium 2,5 -dichloro-4 -(5 -hydroxy-3 -methyl-4 -(sulphophenylazo)pyrazol-1 -yl)benzenesulphonate (CAS no. 6359-98-4) (from peer reviewed journal Glenn M. Shaul, et. al; 1991 and secondary source Glenn M. Shaul, et. al; 1988). The study was carried out in pilot activated sludge process system using several wastewater and mixed liquor at a temperature of 21-25°C and pH range of 7.0-8.0, respectively. Mass balance calculations were made to determine the amount of the dye compound in the waste activated sludge (WAS) and in the activated sludge effluent (ASE). Activated sludge was used as test inoculum for the study. Test chemical conc. used for the study was 1 and 5 mg/l, respectively. Screened raw wastewater from the Greater Cincinnati Mill Creek Sewage Treatment Plant was used as the influent (INF) to three pilot-scale activated sludge biological treatment systems (two experimental and one control) operated in parallel. Each system consisted of a primary clarifier (33 L), complete-mix aeration basin (200 L), and a secondary clarifier (32 L). Each water soluble dye was dosed as commercial product to the screened raw wastewater for the two experimental systems operated in parallel at targeted active ingredient doses of 1 and 5 mg/L of influent flow (low and high spike systems, respectively).All systems were operated for at least three times.All samples were 24 hr composites made up of 6 grab samples collected every 4 hr and stored at 4°C. The possible removal mechanisms for a dye compound in the ASP system include adsorption, biodegradation, chemical transformation, photodegradation, and air stripping. Dye analytical recovery studies were conducted by dosing the purified dye compound into organic-free water, influent wastewater, and mixed liquor. These studies were run in duplicate and each recovery study was repeated at least once to ensure that the dye compound could be extracted. Purified dye standards were analytically prepared from the commercial dye product by repeated recrystallization. The INF, primary effluent (PE), and ASE were filtered, and the filtrate was passed through a column packed with resin. The filter paper and resin were soaked in an ammonia-acetonitrile solution and then Soxhlet extracted with ammonia-acetonitrile. The extract was concentrated and brought up to 50 mL volume with a methanol/dimethylformamide solution. The mixed liquor (ML) samples were separated into two components, the filtrate or soluble (SOL) fraction and the residue (RES) fraction. The SOL fraction was processed similar to the INF, PE, and ASE samples. The RES fraction and the filter paper were processed similar to these samples but the resin adsorption step was omitted. All extracted samples were analyzed by HPLC with an ultraviolet-visible detector. Total suspended solids (TSS) analyses were also performed on the INF, PE, ML, and ASE samples.Percentage recovery of test chemical Disodium 2,5 -dichloro-4 -(5 -hydroxy-3 -methyl-4 -(sulphophenylazo)pyrazol-1 -yl)benzenesulphonate was determined to be 98-101%,thus, it appeared that little or no chemical transformation occurred for test chemical because of contact with the variable wastewater and/or sludge matrix under these conditions. Also it was evaluated that the chemical Disodium 2,5 -dichloro-4 -(5 -hydroxy-3 -methyl-4 -(sulphophenylazo)pyrazol-1 -yl)benzenesulphonate was adsorbed at a level of1 -<1% on the ML solids, indicating that the compound was substantially untreated by the activated sludge process (ASP). Thus, based on %recovery of test chemical, chemical Disodium 2,5 -dichloro-4 -(5 -hydroxy-3 -methyl-4 -(sulphophenylazo)pyrazol-1 -yl)benzenesulphonate was can be considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical chromium(3+) ion hydrogen bis(1-(3-chlorophenyl)-4-[(E)-2-(5-methanesulfonyl-2-oxidophenyl)diazen -1 -yl]-3 -methyl-1H-pyrazol-5 -olate) (from EPI suite, 2018) and for its read across substance (from peer reviewed journals and secondary source), it can be concluded that the test substance chromium(3 +) ion hydrogen bis(1 -(3 -chlorophenyl)-4 -[(E)-2 -(5 -methanesulfonyl-2 -oxidophenyl)diazen -1 -yl]-3 -methyl-1H-pyrazol-5 -olate) can be expected to be not readily biodegradable in nature.