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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 has been attached.
Reference:
Composition 1
Qualifier:
according to
Guideline:
OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))
Principles of method if other than guideline:
Prediction was done using OECD QSAR toll box v3.3
GLP compliance:
not specified
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material: 1,3-Benzenedisulfonic acid, 4-[[5-(aminocarbonyl)-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridinyl]azo]-6-[[4-[[3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl]amino]-6-chloro-1,3,5-triazin-2-yl]amino]-
- IUPAC name: 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazen-1-yl]benzene-1,3-disulfonic acid
- Molecular formula: C27H24Cl2N14O12S3
- Molecular weight: 903.6766 g/mole
- Smiles : CCN1C(=O)C(=C(C(=NNC2=C(C=C(C(=C2)NC3=NC(=NC(=N3)NC4=CC(=C(C=C4)S(=O)
(=O)O)NC5=NC(=NC(=N5)N)Cl)Cl)S(=O)(=O)O)S(=O)(=O)O)C1=O)C)C(=O)N
- Inchl: 1S/C27H24Cl2N14O12S3/c1-3-43-20(45)17(19(30)44)9(2)18(21(43)46)42-41-13-7-12(15(57(50,51)52)8-16(13)58(53,54)55)34-27-38-23(29)37-25(40-27)32-10-4-5-14(56(47,48)49)11(6-10)33-26-36-22(28)35-24(31)39-26/h4-8,46H,3H2,1-2H3,(H2,30,44)(H,47,48,49)(H,50,51,52)(H,53,54,55)(H3,31,33,35,36,39)(H2,32,34,37,38,40)/b42-41+
- Substance type: Organic
- Physical state: Solid powder (red)
Parameter followed for biodegradation estimation:
other: BOD
Key result
Parameter:
other: % biodegradation ( BOD)
Value:
2.38
Sampling time:
28 d
Remarks on result:
other: other details not available
Details on results:
The test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazen-1-yl]benzene-1,3-disulfonic acid showed 2.38 % biodegradation in 28 days by taking BOD as parameter.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 5 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" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Imides (Acute toxicity) OR Substituted Triazines (Acute toxicity) by US-EPA New Chemical Categories ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Non-specific AND Non-specific >> Incorporation into DNA/RNA, due to structural analogy with  nucleoside bases    AND Non-specific >> Incorporation into DNA/RNA, due to structural analogy with  nucleoside bases    >> Specific Imine and Thione Derivatives AND Radical AND Radical >> Radical mechanism via ROS formation (indirect) AND Radical >> Radical mechanism via ROS formation (indirect) >> Specific Imine and Thione Derivatives AND SN1 AND SN1 >> Nucleophilic substitution on diazonium ions AND SN1 >> Nucleophilic substitution on diazonium ions >> Specific Imine and Thione Derivatives by DNA binding by OASIS v.1.3

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Iminium Ion Formation AND SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines by DNA binding by OECD

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Direct Acylation Involving a Leaving group OR Acylation >> Direct Acylation Involving a Leaving group >> Acetates OR SNAr OR SNAr >> Nucleophilic aromatic substitution OR SNAr >> Nucleophilic aromatic substitution >> Halo-triazines by Protein binding by OECD ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Nucleophilic addition OR Nucleophilic addition >> Addition to carbon-hetero double bonds OR Nucleophilic addition >> Addition to carbon-hetero double bonds >> Ketones OR SNAr OR SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds OR SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds >> Activated aryl and heteroaryl compounds by Protein binding by OASIS v1.3 ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Acid moiety OR Acrylamides OR Anilines (Unhindered) OR Hydrazines OR Imides OR Triazines, Aromatic by Aquatic toxicity classification by ECOSAR ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as longer than months by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "h"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 498 Da

Domain logical expression index: "i"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 960 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
not readily biodegradable
Conclusions:
The test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazen-1-yl]benzene-1,3-disulfonic acid showed 2.38 % biodegradation in 28 days by taking BOD as parameter and microorganisms as inoculum. Therefore it is concluded that this test chemical is not readily biodegradable.
Executive summary:

Biodegradability of test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazen-1-yl]benzene-1,3-disulfonic acid (CAS no. 93941 -80 -1) was predicted using OECD QSAR tool box v3.3 using log kow as primary descriptor. The test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazen-1-yl]benzene-1,3-disulfonic acid  showed 2.38 % biodegradation in 28 days by taking BOD as parameter and microorganisms as inoculum. Therefore it is concluded that this test chemical is not readily biodegradable.

Description of key information

Biodegradability of test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)

diazen-1-yl]benzene-1,3-disulfonic acid (CAS no. 93941-80-1) was predicted using OECD QSAR tool box v3.3 using log kow as primary descriptor. The test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)

diazen-1-yl]benzene-1,3-disulfonic acid  showed 2.38 % biodegradation in 28 days by taking BOD as parameter and microorganisms as inoculum. Therefore 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 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)

diazen-1-yl]benzene-1,3-disulfonic acid (CAS no. 93941-80-1)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.

Biodegradability of test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)

diazen-1-yl]benzene-1,3-disulfonic acid (CAS no. 93941-80-1) was predicted using OECD QSAR tool box v3.3 using log kow as primary descriptor. The test chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)

diazen-1-yl]benzene-1,3-disulfonic acid  showed 2.38 % biodegradation in 28 days by taking BOD as parameter and microorganisms as inoculum. Therefore it is concluded that this test chemical is not readily biodegradable.

Another prediction done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)

diazen-1-yl]benzene-1,3-disulfonic acid (CAS no. 35642-64-9) 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  4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)

diazen-1-yl]benzene-1,3-disulfonic acid is expected to be not readily biodegradable.

In a supporting weight of evidence study done from authoritative database ( JCheck, 2017) the Biodegradation experiment was carried out of read across chemical 1,1'-oxybis(pentabromobenzene) (CAS no. 1163-19-5) by taking activated sludge as inoculums at 30 mg/L concentration. The initial concentration of read across chemical taken was 100 mg/L. Biodegradation was analyzed by using two parameters namely O2 consumption (BOD) and test material analysis (GC). The test equipment used was of standard type. Percent biodegradation of read across chemical1,1'-oxybis(pentabromobenzene) was observed to be 0.0 % by both O2 consumption (BOD) and test material analysis (GC) parameters in 14 days. Therefore it is concluded that read across chemical 1,1'-oxybis(pentabromobenzene) is not readily biodegradable.

Another supporting weight of evidence study done from same source as mentioned above ( J Check, 2017) the Biodegradation experiment was carried out for read across test chemical 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazinane-2,4,6-trione (CAS no. 27676-62-6) by taking activated sludge as inoculums at 30 mg/L concentration .The initial concentration of read across chemical taken was 100 mg/L. Biodegradation was analyzed by using three parameters namely BOD and HPLC. The study design was of standard type. Percent biodegradation of read across chemical 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazinane-2,4,6-trione was observed to be 0.0 % by BOD parameter, and 1.0% by HPLC parameters in 28 days.Therefore it is concluded that read across chemical1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazinane-2,4,6-trione is not readily biodegradable.

On the basis of above results for target chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl) diazen-1-yl]benzene-1,3-disulfonic acid (CAS no. 93941-80-1) from (EPI suite 2017 and OECD QSAR tool box v3.3 2017) and for its read across substances (from authoritative database) the target chemical 4-{[4-({3-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl}amino)-6-chloro-1,3,5-triazin-2-yl]amino}-6-[(E)-2-(5-carbamoyl-1-ethyl-2-hydroxy-4- methyl-6-oxo-1,6-dihydropyridin-3-yl)diazen-1-yl]benzene-1,3-disulfonic acid can be expected to be not /readily biodegradable.