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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)
Remarks:
Migrated phrase: estimated by calculation
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
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:
no
Oxygen conditions:
other: aerobic (Biowin 1-6) and anaerobic (Biowin 7)
Inoculum or test system:
other: mixed populations of environmental microorganisms
Details on inoculum:
no data
Duration of test (contact time):
2.208 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:
not specified
Value:
50
Sampling time:
2.208 mo
Remarks on result:
other: Other details not available.
Details on results:
Biowin1 (Linear Model Prediction) : -1.2060: Does Not Biodegrade Fast
Biowin2 (Non-Linear Model Prediction): 0.0000: Does Not Biodegrade Fast
Biowin3 (Ultimate Biodegradation Timeframe): 0.7463: Recalcitrant
Biowin4 (Primary Biodegradation Timeframe): 2.2079: Months
Biowin5 (MITI Linear Model Prediction) : -1.8505: Does Not Biodegrade Fast
Biowin6 (MITI Non-Linear Model Prediction): 0.0000: Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): -2.6009: Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO

BIOWIN (v4.10) Program Results:

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

SMILES : C=CS(=O)(=O)c1ccc(cc1)Nc2nc(CL)nc(n2)Nc3cc(NC(=O)N)c(cc3)N=Nc4cc5c(S(

=O)(=O)O)cc(S(=O)(=O)O)cc5cc4S(=O)(=O)O([Na])

CHEM  : 1,3,6-Naphthalenetrisulfonic acid, 7-[[2-[(aminocarbonyl)amino]-4-[[4

-chloro-6-[[4-(ethenylsulfonyl)phenyl]amino]-1,3,5

MOL FOR: C28 H21 CL1 N9 O12 S4 Na1

MOL WT : 862.21

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

 

************************************************************************

* WARNING - The entered structure contains Na, K or Li               *

*   ---- The metal WAS NOT REMOVED for these calculations ----     *

* Option of Removal/Non-Removal available from entry screen menu-bar. *

* For additional information, see the BIOWIN Help file.              *

************************************************************************

 

Biowin1 (Linear Model Prediction)   : Does Not Biodegrade Fast

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

Biowin3 (Ultimate Biodegradation Timeframe): Recalcitrant

Biowin4 (Primary Biodegradation Timeframe): Months

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

 

***********************************************************************

* Sulfonic acid salt (Na, K, or Li) detected...Mol Wt for prediction *

*  modified to use the acid Mol Wt (840.23)

***********************************************************************

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

TYPE | NUM |      Biowin1 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 1 | Triazine ring (symmetric)                | 0.0095 | 0.0095

Frag | 1 | Aromatic chloride  [-CL]                | -0.1824 | -0.1824

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

Frag | 3 | Sulfonic acid / salt -> aromatic attach  | -0.2238 | -0.6713

Frag | 1 | Azo group  [-N=N-]                      | -0.2418 | -0.2418

MolWt| * | Molecular Weight Parameter               |        | -0.4000

Const| * | Equation Constant                        |        | 0.7475

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

RESULT  |   Biowin1 (Linear Biodeg Probability)    |        | -1.2060

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

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

TYPE | NUM |      Biowin2 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 1 | Triazine ring (symmetric)                | -5.7252 | -5.7252

Frag | 1 | Aromatic chloride  [-CL]                | -2.0155 | -2.0155

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

Frag | 3 | Sulfonic acid / salt -> aromatic attach  | -1.0283 | -3.0849

Frag | 1 | Azo group  [-N=N-]                      | -8.2194 | -8.2194

MolWt| * | Molecular Weight Parameter               |        |-11.9313

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

RESULT  | Biowin2 (Non-Linear Biodeg Probability)  |        | 0.0000

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

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 | 1 | Triazine ring (symmetric)                | -0.2459 | -0.2459

Frag | 1 | Aromatic chloride  [-CL]                | -0.2066 | -0.2066

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

Frag | 3 | Sulfonic acid / salt -> aromatic attach  | 0.1422 | 0.4266

Frag | 1 | Azo group  [-N=N-]                      | -0.3004 | -0.3004

MolWt| * | Molecular Weight Parameter               |        | -1.8568

Const| * | Equation Constant                        |        | 3.1992

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

RESULT  | Biowin3 (Survey Model - Ultimate Biodeg) |        | 0.7463

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

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

TYPE | NUM |      Biowin4 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 1 | Triazine ring (symmetric)                | -0.0575 | -0.0575

Frag | 1 | Aromatic chloride  [-CL]                | -0.1653 | -0.1653

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

Frag | 3 | Sulfonic acid / salt -> aromatic attach  | 0.0216 | 0.0649

Frag | 1 | Azo group  [-N=N-]                      | -0.0528 | -0.0528

MolWt| * | Molecular Weight Parameter               |        | -1.2123

Const| * | Equation Constant                        |        | 3.8477

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

RESULT  |  Biowin4 (Survey Model - Primary Biodeg) |        | 2.2079

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

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 | 1 | Triazine ring (symmetric)                | 0.1168 | 0.1168

Frag | 1 | Aromatic chloride  [-CL]                | 0.0062 | 0.0062

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

Frag | 3 | Sulfonic acid / salt -> aromatic attach  | 0.0221 | 0.0664

Frag | 1 | Azo group  [-N=N-]                      | -0.0459 | -0.0459

Frag | 11 | Aromatic-H                               | 0.0082 | 0.0904

Frag | 3 | -C=CH [alkenyl hydrogen]                | 0.0062 | 0.0186

MolWt| * | Molecular Weight Parameter               |        | -2.4997

Const| * | Equation Constant                        |        | 0.7121

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

RESULT  | Biowin5 (MITI Linear Biodeg Probability) |        | -1.8505

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

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

TYPE | NUM |      Biowin6 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 1 | Triazine ring (symmetric)                | -9.3006 | -9.3006

Frag | 1 | Aromatic chloride  [-CL]                | -0.2191 | -0.2191

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

Frag | 3 | Sulfonic acid / salt -> aromatic attach  | 0.6780 | 2.0341

Frag | 1 | Azo group  [-N=N-]                      |-10.6129 |-10.6129

Frag | 11 | Aromatic-H                               | 0.1201 | 1.3216

Frag | 3 | -C=CH [alkenyl hydrogen]                | 0.0285 | 0.0855

MolWt| * | Molecular Weight Parameter               |        |-24.2565

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

RESULT  |Biowin6 (MITI Non-Linear Biodeg Probability)|        | 0.0000

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

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 | 1 | Triazine ring (symmetric)                | -0.0783 | -0.0783

Frag | 1 | Aromatic chloride  [-CL]                | -0.4023 | -0.4023

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

Frag | 3 | Sulfonic acid / salt -> aromatic attach  | -0.3768 | -1.1305

Frag | 1 | Azo group  [-N=N-]                      | 0.0000 | 0.0000

Frag | 11 | Aromatic-H                               | -0.0954 | -1.0497

Frag | 3 | -C=CH [alkenyl hydrogen]                | -0.0735 | -0.2206

Const| * | Equation Constant                        |        | 0.8361

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

RESULT  |  Biowin7 (Anaerobic Linear Biodeg Prob)  |        | -2.6009

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

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): NO

Validity criteria fulfilled:
not specified
Interpretation of results:
under test conditions no biodegradation observed
Conclusions:
The results indicate that 7-[[2-[(aminocarbonyl)amino]-4-[[4-chloro-6-[[4-[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt was expected to be not readily biodegradable.
Executive summary:

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound 7-[[2-[(aminocarbonyl)amino]-4-[[4-chloro-6-[[4-[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt (CAS No. 94158 -80 -2). The screening test ready biodegradability of the substance was calculated using the software BIOWIN

v4.10. The results indicate that the test chemical is expected to be not readily biodegradable in nature.

Description of key information

Estimation Programs Interface Suite (EPI suite, 2016) was run to predict the biodegradation potential of the test compound 7-[[2-[(aminocarbonyl)amino]-4-[[4-chloro-6-[[4-[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt (CAS No. 94158 -80 -2). The screening test ready biodegradability of the substance was calculated using the software BIOWIN v4.10. The results indicate that the test chemical is expected to be not readily biodegradable in nature.

Key value for chemical safety assessment

Biodegradation in water:
under test conditions no biodegradation observed

Additional information

The predicted data for the test compound substance7-[[2-[(aminocarbonyl)amino]-4-[[4-chloro-6-[[4-

[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt (CAS No. 94158 -80 -2) and the study of 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 7-[[2-[(aminocarbonyl)amino]-4-[[4-chloro-6-[[4-[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt (CAS No. 94158 -80 -2). The screening test ready biodegradability of the substance was calculated using the software BIOWINv4.10. The results indicate that the test chemical is expected to be not readily biodegradable in nature.

Biodegradation in water ability was predicted (SSS QSAR prediction model, 2016) for the test 7-[[2-[(aminocarbonyl)amino]-4-[[4-

chloro-6-[[4-[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt (CAS No. 94158 -80 -2) using the SSS QSAR prediction model. The ready biodegradability of the test substance 7-[[2-[(aminocarbonyl)amino]-4-[[4- chloro-6-[[4-[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt was estimated as 11.68% in 28 days. This result indicates that 7-[[2-[(aminocarbonyl)amino]-4-[[4-chloro-6-[[4-[vinylsulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt was estimated to be not readily biodegradable in water.

Biodegradation study (J-CHECK, 2016) was conducted for 28 days for evaluating the percentage biodegradability of test substance Direct Yellow 50. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l. The percentage degradation of test substance was found to be 0% by BOD and HPLC and 13% by TOC. Thus, the substance Direct Yellow 50 is expected to be not readily biodegradable in water.

Biodegradation study (EnviChem, 2014) was conducted for 14 days for evaluating the percentage biodegradability of test substance Urea J Acid. Concentrationof inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l. The percentage degradation of test substance was found to be 0% by BOD. Thus, the substance Urea J Acid is expected to be not readily biodegradable in water.

 

On the basis of above results of target and its read across substance, it can be concluded that the test substance 7-[[2-[(aminocarbonyl)amino]-4-[[4-chloro-

6-[[4-[vinylsulphonyl]phenyl]amino]- 1,3,5-triazin-2-yl]amino]phenyl]azo]naphthalene-1,3,6-trisulphonic acid, sodium salt can be expected to be not readily biodegradable in nature.

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