Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl]azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: ready biodegradability

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:

no guideline available

Principles of method if other than guideline:

The data is predicted using the OECD QSAR toolbox version 3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: disodium 2-[(5-carbamoyl-1-ethyl-2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridin-3-yl)diazenyl]-4-({4-chloro-6-[(3-{[2-(sulfonatooxy)ethyl] sulfonyl}phenyl)amino]-1,3,5-triazin-2-yl}amino)benzenesulfonate
- Molecular formula: C26H26ClN9O12S3.2Na
- Molecular weight: 832.1576 g/mol
- Smiles notation: CCn1c(c(c(c(c1=O)C(=O)N)C)/N=N/c2cc(ccc2S(=O)(=O)[O-])Nc3nc(nc(n3)Cl)Nc4cccc(c4)S(=O)(=O)CCOS(=O)(=O)[O-])O.[Na+].[Na+]
- InChI: 1S/C26H26ClN9O12S3.2Na/c1-3-36-22(38)19(21(28)37)13(2)20(23(36)39)35-34-17-12-15(7-8-18(17)50(42,43)44)30-26-32-24(27)31-25(33-26) 29-14-5-4-6-16(11-14)49(40,41)10-9-48-51(45,46)47;;/h4-8,11-12,39H,3,9-10H2,1-2H3,(H2,28,37)(H,42,43,44)(H,45,46,47)(H2,29,30,31,32,33);;/q;2*+1/p-2/b35-34+;;
- Substance type: Organic

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

CO2 evolution

Key result

Parameter:

% degradation (CO2 evolution)

Value:

26.8

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 26.79% degradation by CO2 evolution parameter in 28 days.

The prediction was based on dataset comprised from the following descriptors: "CO2 evolution"
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" )  and ("f" and ( not "g") )  )  and "h" )  and "i" )  and "j" )  and ("k" and ( not "l") )  )  and "m" )  and ("n" and "o" )  )

Domain logical expression index: "a"

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

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 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: "e"

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 v1.3

Domain logical expression index: "f"

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: "g"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Isocyanates and Isothiocyanates OR Acylation >> Isocyanates and Isothiocyanates >> Isocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Formamides OR Michael addition OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Alkyl phenols OR No alert found OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine OR SN2 OR SN2 >> Direct Acting Epoxides and related OR SN2 >> Direct Acting Epoxides and related >> Epoxides by DNA binding by OECD

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 7) ONLY

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Reactive unspecified by Acute aquatic toxicity MOA by OASIS ONLY

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Group 1 - Alkali Earth Li,Na,K,Rb,Cs,Fr AND Group 14 - Carbon C AND Group 15 - Nitrogen N AND Group 16 - Oxygen O AND Group 16 - Sulfur S AND Group 17 - Halogens Cl AND Group 17 - Halogens F,Cl,Br,I,At by Chemical elements

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Group 15 - Phosphorus P by Chemical elements

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Not bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 322 Da

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 1.19E003 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy) ethyl]sulphonyl] phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy) ethyl]sulphonyl] phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate (CAS No. 84000 -63 -5) was predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 26.79% degradation by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, the test chemical Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl] phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy) ethyl]sulphonyl] phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate (CAS No. 84000 -63 -5) was predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 26.79% degradation by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, the test chemical Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl] phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate 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 Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate (CAS No. 84000-63-5) and various supporting weight of evidence studies for its closest read across substance with logKow as the primary descriptor 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 Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate (CAS No. 84000-63-5) was estimated.Test substance undergoes 26.79% degradation by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, the test chemical Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate was estimated to be not readily biodegradable in water.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across 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),biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1,3,5 -tris(3,5 -di-tert-butyl-4 -hydroxybenzyl)-1,3,5 -triazinane-2,4,6 –trione. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 1,3,5 -tris(3,5 -di-tert-butyl-4 -hydroxybenzyl)-1,3,5 -triazinane-2,4,6 -trione was determined to be 0 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,1,3,5 -tris(3,5 -di-tert-butyl-4 -hydroxybenzyl)-1,3,5 -triazinane-2,4,6 -trione is considered to be not readily biodegradable in nature.

 

For the same read across chemical1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazinane-2,4,6-trione (CAS no. 27676-62-6), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1,3,5 -tris(3,5 -di-tert-butyl-4 -hydroxybenzyl)-1,3,5 -triazinane-2,4,6 –trione(HPVIS, 2016). The study was performed according to OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test). Fresh sewage treatment plant sample was used as a test inoculum. Initial test substance conc. used in the study were 10 and 20 mg/l, respectively. Water was used as a vehicle as specified in the guideline containing 0.5 ml of the Nonylphenol 10E05P0 solution. The only deviation from the guideline method is the volume of the test solution was reduced from 3.0 L to 1.5L. The carbon dioxide formed by biodegradation was absorbed with NaOH and determined on a carbon analyser. The percentage degradation of substance 1,3,5 -tris(3,5 -di-tert-butyl-4 -hydroxybenzyl)-1,3,5 -triazinane-2,4,6 -trione was determined to be 0 and 7% by CO2 evolution  parameter in 28 days. Thus, based on percentage degradation,1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazinane-2,4,6-trione 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 methylene bis[dibutyl(dithiocarbamate)] (CAS No. 10254-57-6) (HPVIS, 2016). The study was performed according to OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test) under aerobic conditions at a temperature of 21°C. Activated sludge, domestic was used as a test inoculum. Initial test substance conc. used in the study were 10 mg/l, respectively. Control solutions with inoculum and the standard material, sodium benzoate, together with a toxicity control were used for validation purposes. Benzoic acid, sodium salt was used as a positive control. The degradation of the test material was assessed by the determination of carbon dioxide produced. Benzoic acid, sodium salt undergoes 50% degradation in 28 days. The percentage degradation of read across substance methylene bis[dibutyl(dithiocarbamate)] was determined to be 5, 7, 19 and 21% by CO2 evolution  parameter in 6, 14, 20 and 28 days, respectively. Thus, based on percentage degradation, methylene bis[dibutyl(dithiocarbamate)] is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate (from OECD QSAR toolbox version 3.3, 2017) and for its read across substance (from authoritative database J-CHECK and secondary source HPVIS), it can be concluded that the test substance Disodium 2-[[5-carbamoyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3-pyridyl] azo]-4-[[4-chloro-6-[[3-[[2-(sulphonatooxy)ethyl]sulphonyl]phenyl]amino]-1,3,5-triazin-2-yl]amino]benzenesulphonate can be expected to be not readily biodegradable in nature.