Octasodium 2,2'-[(2,2'-disulphonato[1,1'-biphenyl]-4,4'-diyl)bis[imino(6-chloro-1,3,5-triazine-4,2-diyl)imino(1-hydroxy-3-sulphonatonaphthalene-6,2-diyl)azo]]bisnaphthalene-1,5-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

Guideline:

other: 301C

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 the test chemical: 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt
- Molecular formula: C58H38Cl2N14O26S8.8Na
- Molecular weight: 1850.3 g/mol
- Substance type: Organic
- SMILES : Oc1c2ccc(Nc3nc(Nc4ccc(-c5ccc(Nc6nc(Nc7ccc8c(c7)cc(S(=O)(=O)O{-}.[Na]{+})c(/N=N/c7ccc9c(S(=O)(=O)O{-}.[Na]{+})cccc9c7S(=O)(=O)O{-}.[Na]{+})c8O)nc(Cl)n6)cc5S(=O)(=O)O{-}.[Na]{+})c(S(=O)(=O)O{-}.[Na]{+})c4)nc(Cl)n3)cc2cc(S(=O)(=O)O{-}.[Na]{+})c1/N=N/c1ccc2c(S(=O)(=O)O{-}.[Na]{+})cccc2c1S(=O)(=O)O{-}.[Na]{+}

Oxygen conditions:

not specified

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: % degradability BOD

Value:

0.84

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

Percent biodegradation of the test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt was estimated to be 0.84 % by considering BOD as parameter and Microorganism as inoculum in 28 days.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 10 nearest neighbours
Domain  logical expression:Result: In Domain

(((((((((((("a" or "b" or "c" or "d" )  and ("e" and ( not "f") )  )  and "g" )  and "h" )  and "i" )  and ("j" and ( not "k") )  )  and ("l" and ( not "m") )  )  and ("n" and ( not "o") )  )  and ("p" and ( not "q") )  )  and ("r" and ( not "s") )  )  and ("t" and ( not "u") )  )  and ("v" and "w" )  )

Domain logical expression index: "a"

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

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] OR Aliphatic Nitrogen, one aromatic attach [-N] OR Aliphatic Nitrogen, two aromatic attach [-N-] OR Amino Triazine/Pyrazine/Pyrimidine  OR Aromatic Carbon [C] OR Aromatic Nitrogen OR Azo [-N=N-] OR Chlorine, aromatic attach [-Cl] OR Chlorine, olefinic attach [-Cl] 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 Sym-Triazine ring  by Organic functional groups (US EPA) ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Aromatic amine OR Aromatic heterocyclic halide OR Aryl OR Aryl halide OR Azo OR Biphenyl OR Fused carbocyclic aromatic OR Overlapping groups OR Phenol OR Sulfonic acid by Organic Functional groups (nested) ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Aromatic amine OR Aromatic heterocyclic halide OR Aryl OR Aryl halide OR Azo OR Biphenyl OR Fused carbocyclic aromatic OR Naphtalene OR Phenol OR Sulfonic acid OR Triazine by Organic Functional groups 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 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinoneimines OR AN2 >>  Michael-type addition, quinoid structures >> Quinones OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds >> alpha, beta-Unsaturated Aldehydes OR AN2 >> Schiff base formation OR AN2 >> Schiff base formation >> alpha, beta-Unsaturated Aldehydes OR AN2 >> Schiff base formation >> Polarized Haloalkene Derivatives OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Haloalkenes with Electron-Withdrawing Groups OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Polarized Haloalkene Derivatives OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical OR Radical >> Generation of reactive oxygen species OR Radical >> Generation of reactive oxygen species >> Thiols OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> p-Aminobiphenyl Analogs OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR Radical >> ROS formation after GSH depletion (indirect) OR Radical >> ROS formation after GSH depletion (indirect) >> Quinoneimines OR SN1 OR SN1 >> Alkylation after metabolically formed carbenium ion species OR SN1 >> Alkylation after metabolically formed carbenium ion species >> Polycyclic Aromatic Hydrocarbon Derivatives OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> N-Nitroso Compounds OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> p-Aminobiphenyl Analogs OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN1 >> Nucleophilic attack after nitrenium and/or carbenium ion formation OR SN1 >> Nucleophilic attack after nitrenium and/or carbenium ion formation >> N-Nitroso Compounds OR SN2 OR SN2 >> Alkylation, direct acting epoxides and related OR SN2 >> Alkylation, direct acting epoxides and related >> Epoxides and Aziridines OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation >> Haloalkenes with Electron-Withdrawing Groups OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation >> Polycyclic Aromatic Hydrocarbon Derivatives OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives OR SN2 >> SN2 at sp3 and activated sp2 carbon atom OR SN2 >> SN2 at sp3 and activated sp2 carbon atom >> Polarized Haloalkene Derivatives by DNA binding by OASIS v.1.3

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 Not calculated by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Not calculated by Biodeg ultimate (Biowin 3) 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, impaired OH or NH2 group by Estrogen Receptor Binding

Domain logical expression index: "l"

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

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Moderate binder, NH2 group OR Moderate binder, OH grooup by Estrogen Receptor Binding

Domain logical expression index: "n"

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

Domain logical expression index: "o"

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

Domain logical expression index: "p"

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

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Weak binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "r"

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

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as Weak binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "t"

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

Domain logical expression index: "u"

Referential boundary: The target chemical should be classified as Very strong binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "v"

Parametric boundary:The target chemical should have a value of log BCF max which is >= 0.959 log(L/kg wet)

Domain logical expression index: "w"

Parametric boundary:The target chemical should have a value of log BCF max which is <= 3.08 log(L/kg wet)

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

Percent biodegradation of the test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt was estimated to be 0.84 % by considering BOD as parameter and Microorganism as inoculum in 28 days. On the basis of percent degradability value it can be concluded that test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt is not readily biodegradable.

Executive summary:

Biodegradability of test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt (CAS no. 68110-30-5) was estimated by using OECD QSAR tool box v3.3 by considering ten closest read across chemical log Kow as primary descriptor. Percent biodegradation of the test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt was estimated to be 0.84 % by considering BOD as parameter and Microorganism as inoculum in 28 days. On the basis of percent degradability value it can be concluded that test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt is not readily biodegradable.

Description of key information

Biodegradability of test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt (CAS no. 68110-30-5) was estimated by using OECD QSAR tool box v3.3 by considering ten closest read across chemical log Kow as primary descriptor. Percent biodegradation of the test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt was estimated to be 0.84 % by considering BOD as parameter and Microorganism as inoculum in 28 days. On the basis of percent degradability value it can be concluded that test chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt is not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data study for target chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt (CAS no. 68110-30-5) and experimental studies for its structurally similar read across chemicals have been conducted and their results are summarized below for biodegradation in water endpoint.

Another study was experimental study done from Chemosphere journal Vo1.15 (1986) for structurally similar read across chemical Disodium 4,4'-bis(2-hydroxynaphthalen-1-ylazo)biphenyl-2,6'-disulphonate (CAS no.10169 -02 -5) in this study the aerobic biodegradation experiment was performed for read across chemical Disodium 4,4'-bis(2-hydroxynaphthalen-1-ylazo)biphenyl-2,6'-disulphonate using activated sludge at concentration 0.5 g/L dry material as inoculums and initial concentration of chemical taken was 100mg/L for 42 days. By considering DOC removal parameter read across chemical showed 17% degradation in 42 days. The read across chemical Disodium 4,4'-bis(2-hydroxynaphthalen-1-ylazo)biphenyl-2,6'-disulphonate belongs to D category according to table 1 and 2 as its limit value falls in that range. This percentage value is very less So it is concluded that Disodium 4,4'-bis(2-hydroxynaphthalen-1-ylazo)biphenyl-2,6'-disulphonate (CAS no. 10169 -02 -5) is not readily biodegradable.

Next study was also experimental study done from same source as mentioned in above experimental study in this study the aerobic biodegradation experiment was performed for read across chemical tetrasodium;3-[[4-[[4-[(2E)-2-(6-amino-1-oxo-3-sulfonatonaphthalen-2-ylidene)hydrazinyl]-6-sulfonatonaphthalen-1-yl]diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1,5-disulfonate CAS no. 4399 -55 -7) using activated sludge at concentration 0.5 g/L dry material as inoculums and initial concentration of chemical taken was 100 mg/L for 42 days. By considering DOC removal parameter read across chemical showed -27 % degradation in 42 days. This percentage value is very less So it is concluded that read across chemical tetrasodium; 3-[[4-[[4-[(2E)-2-(6-amino-1-oxo-3-sulfonatonaphthalen-2-ylidene)hydrazinyl]-6-sulfonatonaphthalen-1-yl]diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1,5-disulfonate is not readily biodegradable.

On the basis of results of all the studies mentioned above for target chemical 1,5-Naphthalenedisulfonic acid, 2,2'-[(2,2'-disulfo[1,1'-biphenyl]-4,4'-diyl)bis[imino (6-chloro-1,3,5-triazine-4,2-diyl)imino (1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis-, octasodium salt (CAS no. 68110-30-5) and for its structurally similar read across chemicals it can be concluded that test chemical is not readily biodegradable.