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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
Reference:
Composition 0
Qualifier:
according to
Guideline:
OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))
Principles of method if other than guideline:
The data is predicted using the OECD QSAR toolbox version 3.4 with logKow as the primary descriptor.
GLP compliance:
not specified
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material : hexasodium 4,4'-{ethene-1,2-diylbis[(3-sulfonato-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]}bis{6-[(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazenyl]benzene-1,3-disulfonate}
- Molecular formula : C50H44Cl2N18O24S6.6Na
- Molecular weight : 1544.3016 g/mol
- Smiles notation : CCN1C(=C(C(=C(C1=O)N=NC2=CC(=C(C=C2S(=O)(=O)O)S(=O)(=O)O)NC3=NC(=NC(=N3)NC4=CC(=C(C=C4)C=CC5=C(C=C(C=C5)NC6=NC(=NC(=N6)Cl)NC7=C(C=C(C(=C7)N=NC8=C(C(=C(N(C8=O)CC)[O-])C(=N)[O-])C)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)[O-])S(=O)(=O)[O-])Cl)C)C(=N)[O-])[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
- InChl : 1S/C50H44Cl2N18O24S6/c1-5-69-41(73)35(39(53)71)19(3)37(43(69)75)67-65-27-15-25(31(97(83,84)85)17-33(27)99(89,90)91)57-49-61-45(51)59-47(63-49)55-23-11-9-21(29(13-23)95(77,78)79)7-8-22-10-12-24(14-30(22)96(80,81)82)56-48-60-46(52)62-50(64-48)58-26-16-28(34(100(92,93)94)18-32(26)98(86,87)88)66-68-38-20(4)36(40(54)72)42(74)70(6-2)44(38)76/h7-18,75-76H,5-6H2,1-4H3,(H2,53,71)(H2,54,72)(H,77,78,79)(H,80,81,82)(H,83,84,85)(H,86,87,88)(H,89,90,91)(H,92,93,94)(H2,55,57,59,61,63)(H2,56,58,60,62,64)/b8-7?,67-65+,68-66+
- Substance type : Organic
- Physical state : Solid
Oxygen conditions:
aerobic
Inoculum or test system:
other: Micro-organisms
Duration of test (contact time):
28 d
Based on:
not specified
Parameter followed for biodegradation estimation:
other: BOD
Key result
Parameter:
other: BOD
Value:
1.6
Sampling time:
28 d
Remarks on result:
other: Other details not known
Details on results:
Test substance undergoes 1.6% degradation by BOD in 28 days.

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" )  and "e" )  and "f" )  and "g" )  and "h" )  and ("i" and ( not "j") )  )  and ("k" and ( not "l") )  )  and ("m" and ( not "n") )  )  and ("o" and "p" )  )

Domain logical expression index: "a"

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: "b"

Referential boundary: The target chemical should be classified as Nucleophilic addition AND Nucleophilic addition >> Addition to carbon-hetero double bonds AND Nucleophilic addition >> Addition to carbon-hetero double bonds >> Ketones AND SNAr AND SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds AND SNAr >> Nucleophilic aromatic substitution on activated aryl and heteroaryl compounds >> Activated aryl and heteroaryl compounds by Protein binding by OASIS v1.4

Domain logical expression index: "c"

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

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acid moiety AND Acrylamides AND Triazines, Aromatic AND Vinyl/Allyl Alcohols by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 2) ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 5) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 6) ONLY

Domain logical expression index: "h"

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

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.4

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinones and Trihydroxybenzenes OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes OR Radical OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Amino Anthraquinones OR Radical >> Radical mechanism via ROS formation (indirect) >> N,N-Dialkyldithiocarbamate Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones and Trihydroxybenzenes OR SN1 OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Amino Anthraquinones OR SN2 OR SN2 >> Alkylation OR SN2 >> Alkylation >> Alkylphosphates, Alkylthiophosphates and Alkylphosphonates OR SN2 >> Alkylation, direct acting epoxides and related OR SN2 >> Alkylation, direct acting epoxides and related >> Epoxides and Aziridines by DNA binding by OASIS v.1.4

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Acidic [90,100] AND No pKb value by Ionization at pH = 1

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Acidic [0,10) by Ionization at pH = 1

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Acidic [90,100] AND No pKb value by Ionization at pH = 7.4

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Basic [90,100] by Ionization at pH = 7.4

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of log Kow which is >= 0.135

Domain logical expression index: "p"

Parametric boundary:The target chemical should have a value of log Kow which is <= 5.12

Validity criteria fulfilled:
not specified
Interpretation of results:
under test conditions no biodegradation observed
Conclusions:
The test chemical hexasodium 4,4'-{ethene-1,2-diylbis[(3-sulfonato-4,1-phenylene)imino(6-chloro-1,3,5-triazine-4,2-diyl)imino]}bis{6-[(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydro pyridin-3-yl)diazenyl]benzene-1,3-disulfonate} was estimated to be not readily biodegradable in water.
Executive summary:

Biodegradability of hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate}(CAS no. 68991 -98 -0) is predicted using QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 1.6% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate} was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate}(CAS no. 68991 -98 -0) is predicted using QSAR toolbox version 3.4 (2018) with logKow as the primary descriptor. Test substance undergoes 1.6% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate} was estimated to be not readily biodegradable in water.

Key value for chemical safety assessment

Biodegradation in water:
under test conditions no biodegradation observed

Additional information

Predicted data for the target compound hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate} (CAS No. 68991 -98 -0) and various supporting weight of evidence studies for its structurally and functionally similar read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2018) using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemical hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate} (CAS No. 68991 -98 -0) was estimated.Test substance undergoes 1.6% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate} was estimated to be not readily biodegradable in water.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical disodium 2,2'-ethene-1,2-diylbis{5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]benzenesulfonate} (CAS no. 16090-02-1), biodegradation experiment was carried out using river die away test for 35 days for evaluating the percentage biodegradability of read across substance disodium 2,2'-ethene-1,2 -diylbis{5 -[(4 -anilino-6 -morpholin-4 -yl-1,3,5 -triazin-2 -yl)amino]benzenesulfonate}. Initial test substance conc. used was 1 mg/l (1000 ppb). The percentage degradation of substance disodium 2,2'-ethene-1,2 -diylbis{5 -[(4 -anilino-6 -morpholin-4 -yl-1,3,5 -triazin-2 -yl)amino]benzenesulfonate} was determined to be 0% after 35 days by using CO2 evolution parameter. Thus, based on percentage degradation, disodium 2,2'-ethene-1,2 -diylbis{5 -[(4 -anilino-6 -morpholin-4 -yl-1,3,5 -triazin-2 -yl)amino]benzenesulfonate} is considered to be not readily biodegradable in nature.

 

For the same read across chemical disodium 2,2'-ethene-1,2 -diylbis{5 -[(4 -anilino-6 -morpholin-4 -yl-1,3,5 -triazin-2 -yl)amino]benzenesulfonate} (CAS no. 16090 -02 -1), biodegradation study was conducted for 5 days for evaluating the percentage biodegradability of read across substance disodium 2,2'-ethene-1,2 -diylbis{5 -[(4 -anilino-6 -morpholin-4 -yl-1,3,5 -triazin-2 -yl)amino]benzenesulfonate} (HSDB, 2017). Bacteria was used as a test inoculum for the study. The 5 day BOD value of chemical disodium 2,2'-ethene-1,2 -diylbis{5 -[(4 -anilino-6 -morpholin-4 -yl-1,3,5 -triazin-2 -yl)amino]benzenesulfonate} was determined to be 0 g O2/g test material. Thus, based on this BOD5 value, substance disodium 2,2'-ethene-1,2 -diylbis{5 -[(4 -anilino-6 -morpholin-4 -yl-1,3,5 -triazin-2 -yl)amino]benzenesulfonate} is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate} (from OECD QSAR toolbox version 3.4, 2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the test substance hexasodium 4,4'-{ethene-1,2 -diylbis[(3 -sulfonato-4,1 -phenylene)imino(6 -chloro-1,3,5 -triazine-4,2 -diyl)imino]}bis{6 -[(5 -carbamoyl-1 -ethyl-2 -hydroxy-4 -methyl-6 -oxo-1,6 -dihydropyridin-3 -yl)diazenyl]benzene-1,3 -disulfonate}can be expected to be not readily biodegradable in nature.