Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate

Biodegradation in water: screening tests

Link to relevant study record(s)

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 data is predicted using the OECD QSAR toolbox version 3.3 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate
- Molecular formula: C40H44N12O10S2.2K
- Molecular weight: 993.174 g/mol
- Smiles notation: [K+].[K+].C(=C\c1c(cc(cc1)Nc1nc(nc(n1)N(CCO)CCO)Nc1ccccc1)S(=O)(=O)[O-])\c1c(cc(cc1)Nc1nc(nc(n1)N(CCO)CCO)Nc1ccccc1)S(=O)(=O)[O-]
- InChl: 1S/C40H44N12O10S2.2K/c53-21-17-51(18-22-54)39-47-35(41-29-7-3-1-4-8-29)45-37(49-39)43-31-15-13-27(33(25-31)63(57,58)59)11-12-28-14-16-32(26-34(28)64(60,61)62)44-38-46-36(42-30-9-5-2-6-10-30)48-40(50-38)52(19-23-55)20-24-56;;/h1-16,25-26,53-56H,17-24H2,(H,57,58,59)(H,60,61,62)(H2,41,43,45,47,49)(H2,42,44,46,48,50);;/q;2*+1/p-2/b12-11+;;
- Substance type: Organic
- Physical state: Solid

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Based on:

not specified

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

1.55

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 1.55% 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 6 nearest neighbours
Domain  logical expression:Result: In Domain

(((((("a" or "b" or "c" or "d" )  and ("e" and ( not "f") )  )  and ("g" and ( not "h") )  )  and "i" )  and ("j" and ( not "k") )  )  and ("l" and "m" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as C.I. Fluorescent Brightener 28 113 by OECD HPV Chemical Categories

Domain logical expression index: "b"

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

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acid moiety OR Salt OR Triazines, Aromatic by Aquatic toxicity classification by ECOSAR ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain OR Radical OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitro Azoarenes OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitro Azoarenes OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Alkylation, direct acting epoxides and related OR SN2 >> Alkylation, direct acting epoxides and related >> Epoxides and Aziridines OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters by DNA binding by OASIS v.1.3

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as No alert found OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines by DNA binding by OECD

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Non binder, MW>500 by Estrogen Receptor Binding

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Non binder, without OH or NH2 group by Estrogen Receptor Binding

Domain logical expression index: "l"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 516 Da

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 1.17E003 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate (CAS no. 71230 -67 -6) is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 1.55% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2' -disulphonate was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate (CAS no. 71230 -67 -6) is predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 1.55% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate 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 Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate (CAS No. 71230-67-6) and various supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2017) using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical Dipotassium 4,4'-bis[6 -anilino-4 -[bis(2 -hydroxyethyl)amino-1,3,5 -triazin-2 -yl]amino]stilbene-2,2'-disulphonate (CAS No. 71230-67-6) was estimated.Test substance undergoes 1.55% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate 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.

 

In a supporting weight of evidence study from secondary source (OECD SIDS, 2005 and HPVIS, 2017) for the read across chemical 2,2'-ethene-1,2 -diylbis[5 -({4 -anilino-6 -[bis(2 -hydroxyethyl)amino]-1,3,5 -triazin-2 -yl}amino)benzenesulfonic acid] (CAS no. 4404 -43 -7), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2,2'-ethene-1,2 -diylbis[5 -({4 -anilino-6 -[bis(2 -hydroxyethyl)amino]-1,3,5 -triazin-2 -yl}amino)benzenesulfonic acid]. The study was performed according to OECD Guideline 301 D (Ready Biodegradability: Closed Bottle Test) under aerobic conditions. Activated sludge (domestic, non-adapted) was used as a test inoculum for the study. Reference substance aniline undergoes 81 and 83% degradation after 15 and 28 days respectively. The percentage degradation of substance 2,2'-ethene-1,2 -diylbis[5 -({4 -anilino-6 -[bis(2 -hydroxyethyl)amino]-1,3,5 -triazin-2 -yl}amino)benzenesulfonic acid] was determined to be 7, 8 and <10% by using O2 consumption parameter in 5, 10 and 28 days, respectively. Thus, based on percentage degradation, 2,2'-ethene-1,2 -diylbis[5 -({4 -anilino-6 -[bis(2 -hydroxyethyl)amino]-1,3,5 -triazin-2 -yl}amino)benzenesulfonic acid] is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance disodium 4,4'-bis[6 -anilino-[4 -[bis(2 -hydroxyethyl)amino]-1,3,5 -triazin-2 -yl]amino]stilbene-2,2'-disulphonate (CAS no. 4193 -55 -9) (OECD SIDS, 2005 and HPVIS, 2017).The study was performed according to OECD Guideline 303 A "Simulation Test - Aerobic Sewage Treatment: Coupled Unit Test" under aerobic conditions. Activated sludge obtained from sewage treatment plant (STP) was used as a test inoculum for the study. Initial test substance concentration used for the study was 117.6 mg/l based on TOC (20 mg/l) (TOC content of test substance: 17%). TOC content in nutrient solution was 115 mg/l. No reference substance was used for the study. The percentage degradation of substance disodium 4,4'-bis[6 -anilino-[4 -[bis(2 -hydroxyethyl)amino]-1,3,5 -triazin-2 -yl]amino]stilbene-2,2'-disulphonate was determined to be 11% degradation by using TOC removal parameter in 21 days. Thus, based on percentage degradation, disodium 4,4'-bis[6 -anilino-[4 -[bis(2 -hydroxyethyl)amino]-1,3,5 -triazin-2 -yl]amino]stilbene-2,2'-disulphonate is considered to be not readily biodegradable in nature.

 

For the read across chemicaltetrasodium 2,2'-ethene-1,2-diylbis[5-({4-[bis(2-hydroxyethyl)amino]-6-[(4- sulfonatophenyl)amino]-1,3,5-triazin-2-yl}amino)benzenesulfonate] (CAS no. 16470-24-9) from secondary source (OECD SIDS, 2001 and HPVIS, 2017), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance tetrasodium 2,2'-ethene-1,2-diylbis[5-({4-[bis(2-hydroxyethyl)amino]-6-[(4- sulfonatophenyl)amino]-1,3,5-triazin-2-yl}amino)benzenesulfonate]. The study was performed according toEPA OTS 796.3180 (Ready Biodegradability: Modified AFNOR Test) and OECD Guideline 301 A (Ready Biodegradability: DOC Die Away Test), respectively, under aerobic conditions. Domestic sewage effluent was used as a test inoculum obtained from sewage treatment plant. Initial test substance concentration used for the study was 40 mg/l based on DOC (Dissolved Organic Carbon). Modifications of the guideline involve sterilisation instead of sterile filtration and bacterial concentration of 2.6000000 per ml, respectively. The percentage degradation of substance tetrasodium 2,2'-ethene-1,2 -diylbis[5 -({4 -[bis(2 -hydroxyethyl)amino]-6 -[(4 - sulfonatophenyl)amino]-1,3,5 -triazin-2 -yl}amino)benzenesulfonate] was determined to be 1.2% by using DOC removal parameter in 28 days. Thus, based on percentage degradation, tetrasodium 2,2'-ethene-1,2 -diylbis[5 -({4 -[bis(2 -hydroxyethyl)amino]-6 -[(4 - sulfonatophenyl)amino]-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 Dipotassium 4,4'-bis[6-anilino-4-[bis(2-hydroxyethyl)amino-1,3,5-triazin-2-yl]amino]stilbene-2,2'-disulphonate (from OECD QSAR toolbox version 3.3, 2017) and for its read across substance (from authoritative database and secondary source), it can be concluded that the test substance Dipotassium 4,4'-bis[6 -anilino-4 -[bis(2 -hydroxyethyl)amino-1,3,5 -triazin-2 -yl]amino]stilbene-2,2'-disulphonate can be expected to be not readily biodegradable in nature.