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Biodegradation in water: screening tests

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Reference
Endpoint:
biodegradation in water: screening tests
Type of information:
(Q)SAR
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
results derived from a valid (Q)SAR model and falling into its applicability domain, with limited documentation / justification
Justification for type of information:
The supporting QMRF report has been attached
Qualifier:
according to guideline
Guideline:
OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))
Principles of method if other than guideline:
The prediction was done by using OECD QSAR tool box v3.3
GLP compliance:
not specified
Specific details on test material used for the study:
- Name of test material: Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate
- IUPAC name: trisodium 4-[(E)-2-{1-hydroxy-6-[({5-hydroxy-6-[(E)-2-phenyldiazen-1-yl]-7-sulfonatonaphthalen-2-yl}carbamoyl)amino]-3-sulfonatonaphthalen-2-yl}diazen-1-yl]benzoate
- Molecular formula: C34H21N6Na3O11S2
- Molecular weight: 822.673 g/mole
- Smiles : c12c(cc(c(c2S(=O)(=O)[O-])\N=N\c2ccc(cc2)C(=O)[O-])O)cc(NC(=O)Nc2cc3cc(S(=O)(=O)[O-])c(\N=N\c4ccccc4)c(c3cc2)O)cc1.[Na+].[Na+].[Na+]
- Inchl: 1S/C34H24N6O11S2.3Na/c41-27-16-19-14-24(11-13-26(19)32(53(49,50)51)29(27)39-38-22-8-6-18(7-9-22)33(43)44)36-34(45)35-23-10-12-25-20(15-23)17-28(52(46,47)48)30(31(25)42)40-37-21-4-2-1-3-5-21;;;/h1-17,41-42H,(H,43,44)(H2,35,36,45)(H,46,47,48)(H,49,50,51);;;/q;3*+1/p-3/b39-38+,40-37+;;;
- Substance type: Organic
- Physical state: Solid
Oxygen conditions:
aerobic
Inoculum or test system:
other: Microrganisms
Duration of test (contact time):
28 d
Parameter followed for biodegradation estimation:
other: BOD
Key result
Parameter:
other: % degradability BOD
Value:
0.143
Sampling time:
28 d
Remarks on result:
other: other details not available
Details on results:
The test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate showed 0.14 % biodegradation by considering BOD as parameter in 28 days.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 7 nearest neighbours
Domain  logical expression:Result: In Domain

(((("a" or "b" or "c" or "d" or "e" or "f" )  and "g" )  and "h" )  and ("i" and "j" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as SN1 OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic phenylureas by DNA binding by OECD ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Aryl OR Azo OR Carboxylic acid OR Fused carbocyclic aromatic OR Naphtalene OR Phenol OR Sulfonic acid OR Urea derivatives by Organic Functional groups ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Aryl OR Azo OR Carboxylic acid OR Fused carbocyclic aromatic OR Overlapping groups OR Phenol OR Sulfonic acid OR Urea derivatives by Organic Functional groups (nested) ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] OR Aliphatic Nitrogen, one aromatic attach [-N] OR Aromatic Carbon [C] OR Azo [-N=N-] OR Carbonyl, olefinic attach [-C(=O)-] OR Carbonyl, one aromatic attach [-C(=O)-] OR Hydroxy, aromatic attach [-OH] OR Miscellaneous sulfide (=S) or oxide (=O) OR Nitrogen, two or tree olefinic attach [>N-] OR Olefinic carbon [=CH- or =C<] OR Oxygen, one aromatic attach [-O-] OR Suflur {v+4} or {v+6} OR Sulfonate, aromatic attach [-SO2-O] OR Urea [-OC(=O)N-] OR Urea, N and N'-diaryl subsrituted  by Organic functional groups (US EPA) ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] OR Aliphatic Nitrogen, one aromatic attach [-N] OR Aromatic Carbon [C] OR Azo [-N=N-] OR Carbonyl, olefinic attach [-C(=O)-] OR Carbonyl, one aromatic attach [-C(=O)-] OR Hydroxy, aromatic attach [-OH] OR Miscellaneous sulfide (=S) or oxide (=O) OR Nitrogen, two or tree olefinic attach [>N-] OR Olefinic carbon [=CH- or =C<] OR Oxygen, one aromatic attach [-O-] OR Suflur {v+4} or {v+6} OR Sulfonate, aromatic attach [-SO2-O] OR Urea [-OC(=O)N-] OR Urea, N and N'-diaryl subsrituted  by Organic functional groups (US EPA) ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Anion OR Aromatic compound OR Azo compound OR Carbonic acid derivative OR Carboxylic acid derivative OR Carboxylic acid salt OR Cation OR CO2 derivative (general) OR Hydroxy compound OR Phenol OR Sulfonic acid derivative by Organic functional groups, Norbert Haider (checkmol) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Not calculated by Biodeg BioHC half-life (Biowin) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as weeks - months by Biodeg primary (Biowin 4) ONLY

Domain logical expression index: "i"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 315 Da

Domain logical expression index: "j"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 957 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
not readily biodegradable
Conclusions:
The test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate showed 0.14 % biodegradation by considering BOD as parameter and microorganisms as inoculum in 28 days.
Executive summary:

Biodegradability of test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate ( CAS no. 6598 -63 -6) was predicted by using OECD QSAR tool box v3.3 using log Kow as primary descriptor. The test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate showed 0.14 % biodegradation by considering BOD as parameter and microorganisms as inoculum in 28 days. Based on Percent biodegradability it is concluded that this test chemical is not readily biodegradable.

Description of key information

Biodegradability of test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate ( CAS no. 6598 -63 -6) was predicted by using OECD QSAR tool box v3.3 using log Kow as primary descriptor. The test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate showed 0.14 % biodegradation by considering BOD as parameter and microorganisms as inoculum in 28 days. Based on Percent biodegradability it is concluded that this test chemical is not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:
under test conditions no biodegradation observed

Additional information

Predicted data for target compound Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl] azo]benzoate (CAS no. 6598 -63 -6) and supporting weight of evidence studies for its closest read across chemicals with log Kow as a primary descriptor were reviewed for the biodegradation endpoint which are summarized as below.

In first predicted data study the biodegradability of test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate was estimated by using OECD QSAR tool box v3.3 using log Kow as primary descriptor. The test chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate showed 0.14 % biodegradation by considering BOD as parameter and microorganisms as inoculum in 28 days. Based on Percent biodegradability it is concluded that this test chemical is not readily biodegradable.

 

Next weight of evidence study was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test chemicalTrisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoate 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 Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoateis not readily biodegradable.

 

The supporting weight of evidence study was done from authoritative database (J Check, 2017) for tread across chemical disodium 4-amino-3-[(E)-2-(4-{4-[(E)-2-(2,4-diaminophenyl)diazen-1-yl]phenyl}phenyl)diazen-1-yl]-5-hydroxy-6-[(E)-2-phenyldiazen-1-yl]naphthalene-2,7-disulfonate (CAS no. 1937-37-7). In this study the read across chemical was subjected to biodegradation test by taking activated sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD, TOC and HPLC parameters. The initial concentration of read across chemical was 100 mg/L. The study design used was of standard type. The read across chemical disodium 4-amino-3-[(E)-2-(4-{4-[(E)-2-(2,4-diaminophenyl)diazen-1-yl]phenyl}phenyl)diazen-1-yl]-5-hydroxy-6-[(E)-2-phenyldiazen-1-yl]naphthalene- 2,7-disulfonate showed 0 % biodegradation by all three parameters namely BOD, TOC and HPLC parameter in 28 days. Based on percent biodegradability it is concluded that read across chemical disodium 4-amino-3-[(E)-2-(4-{4-[(E)-2-(2,4-diaminophenyl)diazen-1-yl]phenyl}phenyl)diazen-1-yl]-5-hydroxy-6-[(E)-2-phenyldiazen-1-yl] naphthalene-2,7-disulfonate is not readily biodegradable.

 

Similarly another supporting weight of evidence study was also done from same source as mentione d above (J check, 2017) for another read across chemical tetrasodium 3,3'-[carbonylbis[imino(2-methyl-4,1-phenylene)azo]]bisnaphthalene-1,5-disulphonate (CAS no. 3214-47-9). In this study the read across chemical was subjected to biodegradation test by taking sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD, TOC and HPLC parameters. The initial concentration of read across chemical was 100 mg/L and study design was of standard type. The read across chemical tetrasodium 3,3'-[carbonylbis[imino(2-methyl-4,1-phenylene)azo]]bisnaphthalene-1,5-disulphonateshowed 13 % biodegradation by TOC parameter and 0 % biodegradation by other two parameters namely BOD and HPLC in 28 days. Based on percent biodegradability it is concluded that read across chemical tetrasodium 3,3'-[carbonylbis[imino(2-methyl-4,1-phenylene)azo]]bisnaphthalene-1,5-disulphonate is not readily biodegradable.

 

On the basis of above results for target chemical Trisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato -2-naphthyl]azo]benzoate ( CAS no. 6598 -63 -6) from ( EPI suite 2017 and OECD QSAR tool box v3.3 2017) and for its read across substances ( from authoritative database) the target chemicalTrisodium 4-[[1-hydroxy-6-[[[[5-hydroxy-6-(phenylazo)-7-sulphonato-2-naphthyl]amino]carbonyl]amino]-3-sulphonato-2-naphthyl]azo]benzoatecan be expected to be not readily biodegradable.