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REACH

9,10-Anthracenedione, 1,4-diamino-, N,N'-bis(4-C7-17-branched alkylphenyl) derivs.

EC number: 308-067-0 | CAS number: 97862-23-2

Life Cycle description
Uses advised against

Environmental fate & pathways

Biodegradation in water: screening tests

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Administrative data

Link to relevant study record(s)

Reference

Endpoint:: biodegradation in water: ready biodegradability
Type of information:: calculation (if not (Q)SAR)
Adequacy of study:: weight of evidence
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
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.
Parameter:: probability of ready biodegradability (QSAR/QSPR)
Remarks on result:: other: not readily biodegradable as estimated by BIOWIN model
Details on results:: Biowin1 (Linear Model Prediction) : 0.3264: Does Not Biodegrade Fast
Biowin2 (Non-Linear Model Prediction): 0.0010: Does Not Biodegrade Fast
Biowin3 (Ultimate Biodegradation Timeframe): 1.2338: Recalcitrant
Biowin4 (Primary Biodegradation Timeframe): 2.4507: Weeks-Months
Biowin5 (MITI Linear Model Prediction) : -0.7433: Does Not Biodegrade Fast
Biowin6 (MITI Non-Linear Model Prediction): 0.0000: Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): -2.0427: Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO
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 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 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 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 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 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 test chemical and supporting weight of evidence studies for its structurally 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 chemical 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 test chemical is expected to be not readily biodegradable.

In a supporting weight of evidence study from peer reviewed journal (J. A. Buswell and Peter Jurtshuk, 1969) for test chemical biodegradation experiment was conducted for evaluating the percentage biodegradability of test chemical using resting cell suspension of Corynebacterium sp. as the test inoculum. Corynebacterium sp.(7EIC),was isolated from soil by conventional enrichment technique with propane as sole carbon. Medium L with n-octane as the sole carbon source (supplied in the vapour phase), was used for growth of the organism. For solid medium 2% (w/v) Difco Bacto-agar was added. Resting cell suspensions for polarographic investigations were obtained by growing cell batches, prepared by transferring a five-day slope culture to one-litre amounts of Medium L contained in 4-litre filtering flasks. The flasks were agitated on a reciprocal shaker at 30 ~ for four days. The cell mass was harvested after four days, washed, and resuspended in phosphate buffer. Exact test chemical conc. used for the study was not known, but a variable substrate concentration (saturating concentration that gave the maximal oxidation rate) was taken for the study. The final reaction mixture contained 0.02 M phosphate buffer (pH 7.0), 0.2 ml of resting cell suspension (0.78--2.60 mg dry wt), and a variable substrate concentration (saturating concentration that gave the maximal oxidation rate). The final reaction volume was 1.7 ml and the experiments were conducted at 30°C. All reactions were initiated by the addition of the hydrocarbon substrate. Substrate was added to the reaction vessel as an emulsion prepared by sonic oscillation (10 sec at full power with a Bronwill Sonifier) of 0.5 ml hydrocarbon with 10 ml of deionized H2O. Specific activities are reported as µl O2 consumed per hr per mg dry cell wt at 30°C. All specific activities were corrected by subtracting the endogenous respiratory rate, which ranged from 1.6 to 16.7 µl 02 per hr per mg dry wt of cells. Hydrocarbon oxidation was measured by oxygraphy using a YSI Clark oxygen electrode in conjunction with a Gilson Model KM Oxygraph. Specific activity for test chemical oxidation decreases because of a longer chain length. No activity was observed when test substance was supplied at low concentrations. The percentage degradation of test substance was determined to be 11%.Thus, based on percentage degradation, is considered to be not readily biodegradable in water.

Another biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of the same test chemical HSDB, 2017). Bacteria were used as a test inoculum isolated from Colgate Creek sediment. These bacteria were cultured in water obtained from both Colgate Creek and Eastern Bay in Chesapeake Bay, MD, respectively for 28 days at 20°C. The percentage degradation of test substance was determined to be 17-29% and 7-24% after 28 days. Thus, based on percentage degradation, test chemical is considered to be not readily biodegradable in nature.

Last study was reviewed from authoritative database (J-CHECK, 2017), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of test chemical. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of test substance was determined to be 1 and 0% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, test chemical is considered to be not readily biodegradable in nature.

On the basis of above results test chemical it is concluded that the test chemical is expected to be not readily biodegradable in nature.

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