5-amino-2-anilinobenzenesulphonic acid

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

calculation (if not (Q)SAR)

Remarks:

Migrated phrase: estimated by calculation

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: 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 4.10Estimates 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

Duration of test (contact time):

2.509 mo

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.

Parameter:

other: Half-life

Value:

50

Sampling time:

2.509 mo

Remarks on result:

other: Other details not known

Details on results:

Biowin1 (Linear Model Prediction) : 0.0585: Does Not Biodegrade Fast
Biowin2 (Non-Linear Model Prediction): 0.0221: Does Not Biodegrade Fast
Biowin3 (Ultimate Biodegradation Timeframe): 2.5094: Weeks-Months
Biowin4 (Primary Biodegradation Timeframe): 3.2762: Days-Weeks
Biowin5 (MITI Linear Model Prediction) : -0.3017: Does Not Biodegrade Fast
Biowin6 (MITI Non-Linear Model Prediction): 0.0027: Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): -0.6416: Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO

BIOWIN (v4.10) Program Results:

==============================

SMILES : O=S(=O)(O)c(c(Nc(cccc1)c1)ccc2N)c2

CHEM : Benzenesulfonic acid, 5-amino-2-(phenylamino)-

MOL FOR: C12 H12 N2 O3 S1

MOL WT : 264.30

--------------------------- BIOWIN v4.10 Results ----------------------------

Biowin1 (Linear Model Prediction) : Does Not Biodegrade Fast

Biowin2 (Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months

Biowin4 (Primary Biodegradation Timeframe): Days-Weeks

Biowin5 (MITI Linear Model Prediction) : Does Not Biodegrade Fast

Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: NO

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin1 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.2338 | -0.4675

Frag | 1 | Sulfonic acid / salt -> aromatic attach | -0.2238 | -0.2238

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.1281 | 0.1281

MolWt| * | Molecular Weight Parameter | | -0.1258

Const| * | Equation Constant | | 0.7475

============+============================================+=========+=========

RESULT | Biowin1 (Linear Biodeg Probability) | | 0.0585

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Aromatic amine [-NH2 or -NH-] | -1.9070 | -3.8140

Frag | 1 | Sulfonic acid / salt -> aromatic attach | -1.0283 | -1.0283

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 1.7991 | 1.7991

MolWt| * | Molecular Weight Parameter | | -3.7531

============+============================================+=========+=========

RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 0.0221

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin3 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.1349 | -0.2699

Frag | 1 | Sulfonic acid / salt -> aromatic attach | 0.1422 | 0.1422

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.0220 | 0.0220

MolWt| * | Molecular Weight Parameter | | -0.5841

Const| * | Equation Constant | | 3.1992

============+============================================+=========+=========

RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 2.5094

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.1084 | -0.2168

Frag | 1 | Sulfonic acid / salt -> aromatic attach | 0.0216 | 0.0216

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.0049 | 0.0049

MolWt| * | Molecular Weight Parameter | | -0.3813

Const| * | Equation Constant | | 3.8477

============+============================================+=========+=========

RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 3.2762

============+============================================+=========+=========

Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks

(Primary & Ultimate) 2.00 -> months 1.00 -> longer

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin5 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.1577 | -0.3154

Frag | 1 | Sulfonic acid / salt -> aromatic attach | 0.0221 | 0.0221

Frag | 8 | Aromatic-H | 0.0082 | 0.0657

MolWt| * | Molecular Weight Parameter | | -0.7863

Const| * | Equation Constant | | 0.7121

============+============================================+=========+=========

RESULT | Biowin5 (MITI Linear Biodeg Probability) | | -0.3017

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Aromatic amine [-NH2 or -NH-] | -1.2264 | -2.4527

Frag | 1 | Sulfonic acid / salt -> aromatic attach | 0.6780 | 0.6780

Frag | 8 | Aromatic-H | 0.1201 | 0.9611

MolWt| * | Molecular Weight Parameter | | -7.6300

============+============================================+=========+=========

RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.0027

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin7 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.2778 | -0.5556

Frag | 1 | Sulfonic acid / salt -> aromatic attach | -0.3768 | -0.3768

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.2182 | 0.2182

Frag | 8 | Aromatic-H | -0.0954 | -0.7634

Const| * | Equation Constant | | 0.8361

============+============================================+=========+=========

RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | -0.6416

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

Ready Biodegradability Prediction: (YES or NO)

----------------------------------------------

Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey

model) result is "weeks" or faster (i.e. "days", "days to weeks", or

"weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then

the prediction is YES (readily biodegradable). If this condition is not

satisfied, the prediction is NO (not readily biodegradable). This method

is based on application of Bayesian analysis to ready biodegradation data

(see Help). Biowin5 and 6 also predict ready biodegradability, but for

degradation in the OECD301C test only; using data from the Chemicals

Evaluation and Research Institute Japan (CERIJ) database.

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

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 Benzenesulfonic acid, 5-amino-2-(phenylamino)- is not expected to be readily biodegradable.

Executive summary:

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound Benzenesulfonic acid, 5-amino-2-(phenylamino)- (CAS no. 91 -30 -5) 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 Benzenesulfonic acid, 5-amino-2-(phenylamino)- is not expected to be readily biodegradable.

Description of key information

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound Benzenesulfonic acid, 5-amino-2-(phenylamino)- (CAS no. 91 -30 -5) 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 Benzenesulfonic acid, 5-amino-2-(phenylamino)- is not expected to be readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Various predicted data for the test compound Benzenesulfonic acid, 5 -amino-2 -(phenylamino)- (CAS No. 91-30-5) and for its read across substance were reviewed for the biodegradation end point which are summarized as below:

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound Benzenesulfonic acid, 5-amino-2-(phenylamino)- (CAS no. 91 -30 -5) 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 Benzenesulfonic acid, 5-amino-2-(phenylamino)- is not expected to be readily biodegradable.

Biodegradation study of read across substance 4-Amino-1,1’-azobenzene-3,4'-disulfonic acid (acid yellow 9) (CAS no. 101-50-8) was performed using 15 different Streptomyces spp. for 14 days (A. Paszcyzynski, et. al; 1991) . The test was performed using 15 different Streptomyces spp. as an inoculum. The read across substance conc. used is 50 mg/l. Each Streptomyces spp. was grown in a cotton-plugged 250 ml flask containing 25 ml of the following medium: 0.2 M Tris buffer (pH 7.6) 100 ml, 1.0g vitamin-free Casamino acids, 100 µg thiamine, 100 µg biotin, 2 g D-glucose, 900 ml deionized wate. Thiamine, biotin, and D-glucose were filter sterilized and added to the autoclaved medium. The dye was filter sterilized and added at 0.005% (w/v) to the autoclaved basal medium. Cultures were incubated at 37ᵒC for 14 days with shaking (200 rev min¹). Three replicates for each strain grown in only the basal medium were incubated as well.Degradation of read across substance was determined by spectrophotometrically and by using HPLC.

The percentage biodegradation of read across substance was found to be 0% i.e; no degradation of test substance was observed by the 15 different Streptomyces spp. Thus, the substance 4-Amino-1,1’-azobenzene-3,4'-disulfonic acid was determined to be non-biodegradable.

 

Biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance 2-Amino-8-naphthol-6-sulfonic acid (CAS no. 90-51-7) (J-CHECK, 2016). Concentration of inoculum i.e, sludge used was 30 mg/l and initial substance conc. used in the study was 100 mg/l. The read across substance is determined to be 5.3 % biodegraded in water after 2 wk (14 days) on the basis of O2 consumption, BOD. 0.4% by TOC removal and <0 % by (UVVIS) parameters. Hence, the substance 2-Amino-8-naphthol-6-sulfonic acid is considered to be not readily biodegradable in water.

A closed bottle test according to OECD 301D guidelines was performed to determine the ready biodegradability of 7-Amino-4 hydroxy- 2 – naphthalenesulphonic acid (CAS no. 87-02-5) (GREIM H.; et. al, 1994). No degradation of read across chemical 7-Amino-4 hydroxy- 2 – naphthalenesulphonic acid was observed in 28 days. Therefore, the chemical was considered to be not readily biodegradable.

 

Biodegradation screening test was conducted for 14 days (2 weeks) for evaluating the percentage biodegradability of the read across substance 7-Amino-4 hydroxy- 2 - naphthalenesulphonic acid (CAS no. 87-20 -5) (J-CHECK, 2016). Concentration of inoculum i.e, sludge is 30 mg/l and initial substance conc. used in the study is 100 mg/l. The percentage degradation of read across substance is determined to be 6.3% by BOD, 8.4% by TOC and 0% by UV-VIS Thus, the substance 7-Amino-4 hydroxy- 2 - naphthalenesulphonic acid was considered to be not readily biodegradable in water.

 

A batch test in an open system was conducted for evaluating the biodegradability of 1-Naphthylamine-6-sulphonic acid (CAS no. 119-79-9) (P. Pitter, 1976). The compound was the sole source of organic carbon for the microbes of the inoculum. Degradation was studied by determining COD (organic carbon). The pH of the biological medium was 7.2. Initial concentration; 125 - 200mg/l COD. Inoculum; Activated sludge, adapted for 20 days, fed by glucose and peptone with simultaneous addition of the substance tested in the concentration up to 125 mg/l. The sludge age was 5 days. Concentration of the inoculum; 100mg/l. Average temperature during the experiment; 20°C. Under the test conditions the compound was evaluated to be biologically hard to decompose(non-biodegradable).

Biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2-Amino-1,5-naphthalenedisulfonic acid (CAS no. 117-62-4) (J-CHECK, 2016). Concentration of inoculum i.e, sludge used was 30 mg/l and initial substance conc. used in the study was 100 mg/l. The percentage degradation of read across substance was determined to be 1% by BOD, 0% by HPLC and 5% by TOC removal in 28 days. Thus, the substance 2-Amino-1,5-naphthalenedisulfonic acid is not expected to be readily biodegradable in water.

 

Biodegradation study was conducted for 30 days for evaluating the percentage biodegradability of read across substance1,3-Naphthalenedisulfonic acid, 6-amino- (CAS no. 118-33-2) (GREIM H.; et. al, 1994). No degradation of read across substance was determined by BOD in 30 days. Thus, the substance1,3-Naphthalenedisulfonic acid, 6-amino- is not expected to be readily biodegradable in water.

On the basis of above results for target and read across substance, it can be concluded that the test substance Benzenesulfonic acid, 5-amino-2-(phenylamino)- is likely to be not readily biodegradable in nature.