Sodium hydrogen 8-aminonaphthalene-1,6-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 3.4 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: sodium hydrogen 8-aminonaphthalene-1,6-disulfonate
- Molecular formula: C10H8NNaO6S2
- Molecular weight: 325.2962 g/mol
- Smiles notation: c1cc2cc(cc(c2c(c1)S(=O)(=O)O)N)S(=O)(=O)[O-].[Na+]
- InChl: 1S/C10H9NO6S2.Na/c11-8-5-7(18(12,13)14)4-6-2-1-3-9(10(6)8)19(15,16)17;/h1-5H,11H2,(H,12,13,14)(H,15,16,17);/q;+1/p-1
- 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:

1.725

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 1.73% 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 7 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Naphthalene sulfonic acids, condensates by OECD HPV Chemical Categories

Domain logical expression index: "b"

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

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Non-covalent interaction AND Non-covalent interaction >> DNA intercalation AND Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines AND Radical AND Radical >> Radical mechanism via ROS formation (indirect) AND Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines AND SN1 AND SN1 >> Nucleophilic attack after metabolic nitrenium ion formation AND SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines by DNA binding by OASIS v.1.4

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> Substituted Anilines by Protein binding by OASIS v1.4

Domain logical expression index: "e"

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

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Acid moiety AND Anilines (Unhindered) AND Salt by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Non-covalent interaction AND Non-covalent interaction >> DNA intercalation AND Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines AND Radical AND Radical >> Radical mechanism via ROS formation (indirect) AND Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines AND SN1 AND SN1 >> Nucleophilic attack after metabolic nitrenium ion formation AND SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines by DNA binding by OASIS v.1.4

Domain logical expression index: "h"

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 No alert found OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Amino Anthraquinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroaniline Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroarenes with Other Active Groups OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR Radical >> Radical mechanism via ROS formation (indirect) >> p-Aminobiphenyl Analogs OR Radical >> Radical mechanism via ROS formation (indirect) >> Polynitroarenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones and Trihydroxybenzenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation >> Nitroarenes with Other Active Groups OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Amino Anthraquinones OR SN1 >> Nucleophilic attack after nitrenium ion formation OR SN1 >> Nucleophilic attack after nitrenium ion formation >> p-Aminobiphenyl Analogs OR SN1 >> Nucleophilic attack after nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroaniline Derivatives OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroarenes with Other Active Groups OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Polynitroarenes OR SN2 OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 >> Nitroarenes with Other Active Groups by DNA binding by OASIS v.1.4

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg primary (Biowin 4) 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"

Similarity boundary:Target: Nc1cc(S(O)(=O)=O)cc2cccc(S(=O)(=O)O{-}.[Na]{+})c12
Threshold=60%,
Dice(Atom centered fragments)
Atom type; Count H attached; Hybridization

Domain logical expression index: "l"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 239 Da

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 341 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical sodium hydrogen 8-aminonaphthalene-1,6-disulfonate was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of sodium hydrogen 8-aminonaphthalene-1,6-disulfonate (CAS no. 74543 -22 -9) is predicted using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 1.73% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical sodium hydrogen 8 -aminonaphthalene-1,6 -disulfonate was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of sodium hydrogen 8-aminonaphthalene-1,6-disulfonate (CAS no. 74543 -22 -9) is predicted using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 1.73% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical sodium hydrogen 8 -aminonaphthalene-1,6 -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 compoundsodium hydrogen 8-aminonaphthalene-1,6-disulfonate(CAS No. 74543-22-9) 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 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemicalsodium hydrogen 8-aminonaphthalene-1,6-disulfonate(CAS No. 74543-22-9) was estimated.Test substance undergoes 1.73% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical sodium hydrogen 8 -aminonaphthalene-1,6 -disulfonate was estimated to be not readily biodegradable in water.

 

In a supporting weight of evidence study from peer reviewed journal (D. Brown and B. Hamburger, 1987) for the read across chemical 4-amino-3-methylbenzenesulfonic acid (CAS no. 98-33-9),biodegradation experiment was carried out for 28 days for evaluating the percentage biodegradability of the read across substance 4 -Amino-3 -methylbenzenesulfonic acid. The study was performed according to EPA OTS 796.3180 (Ready Biodegradability: Modified AFNOR Test) under aerobic conditions. The percentage degradation of substance 4-amino-3-methylbenzenesulfonic acid was determined to be 2 and 12% by DOC removal parameter in 28 days. Thus, based on percentage degradation, 4 -Amino-3 -methylbenzenesulfonic acid was considered to be not readily biodegradable in water.

 

Another biodegradation study was carried out for 28 days for evaluating the percentage biodegradability of the read across substance 4 -Amino-3 -methylbenzenesulfonic acid (CAS no. 98 -33 -9). The study was performed according to OECD Guideline 302 B (Inherent biodegradability: Zahn-Wellens/EMPA Test) under aerobic conditions(D. Brown and B. Hamburger, 1987). The percentage degradation of substance 4 -Amino-3 -methylbenzenesulfonic acid was determined to be 22% by DOC removal parameter in 28 days. Thus, based on percentage degradation, 4 -Amino-3 -methylbenzenesulfonic acid was considered to be not readily biodegradable in nature.

 

For the same read across substance4 -Amino-3 -methylbenzenesulfonic acid (CAS no. 98 -33 -9)from peer reviewed journal (D. Brown and B. Hamburger, 1987), biodegradation study was carried out for evaluating the percentage biodegradability of the read across substance 4 -Amino-3 -methylbenzenesulfonic acid (CAS no. 98 -33 -9). Activated sludge was used as an inoculum and the study was performed under anaerobic conditions at a temperature of 35°C for a period of approx. 100 days. Samples of the aqueous phase were analyzed either qualitatively or quantitatively by an appropriate chromatographic method for the presence of certain of the expected aromatic amine metabolites. The percentage degradation of substance4 -Amino-3 -methylbenzenesulfonic acidwas determined to be 0% by appropriate chromatography method and DOC analysis in approx. 100 days. Thus, based on percentage degradation, 4 -Amino-3 -methylbenzenesulfonic acid was considered to be not readily biodegradable in nature.

 

In an another supporting weight of evidence study from peer reviewed journal (J. Ruff et.al, 1999), biodegradation experiment was conducted for 9 days for evaluating the percentage biodegradability of read across substance 6 -aminonaphthalene-1,3 -disulfonic acid (CAS no. 118-33-2). Test chemical 6 -aminonaphthalene-1,3 -disulfonic acid was purchased from TCI (Tokyo) at the highest purity available. Glassware was cleaned thoroughly and care taken to exclude extraneous sulfur. Pseudomonas putida strain S-313 was used as a test inoculum obtained from activated sludge from sewage treatment plants in Konstanz, Germany (largely communal) and Ludwigshafen, Germany (largely industrial).Initial experiments were done with the phosphate-buffered medium. The sulfur-free acetate-Tris-buffered salts medium gave the same products with negligible background growth, and thus used as a standard medium. Sulfur was provided at 50µM, except for disulfonates, where the initial sulfonate concentration was 30µM.Cultures were grown in screw-capped tubes on a roller at 30°C.Samples were taken at 3-day intervals for 9 days. Bacteria were removed by centrifugation and the protein content measured, and 100µl portions of the supernatant fluid were examined by HPLC. Substrates and products were determined by isocratic reversed-phase high-pressure liquid chromatography (HPLC) or by ion-pair chromatography. The apparatus included a diode array detector. Chromatograms were initially evaluated with wavelength settings of 245 nm for the amino-naphthalenedisulfonates. Protein was assayed by a Lowry-type method. The percentage degradation of read across chemical 6 -aminonaphthalene-1,3 -disulfonic acid was determined to be 0% by using Pseudomonas putida strain S-313 as an inoculum. Thus, based on percentage degradation, chemical 6 -aminonaphthalene-1,3 -disulfonic acid can be considered to be not readily biodegradable in nature.

 

Additional biodegradation experiment was conducted for 30 days under aerobic conditions for evaluating the percentage biodegradability of the same read across substance 6 -amino naphthalene-1,3 -disulfonic acid (CAS no. 118 -33 -2) (from peer reviewed journal (GREIM H. et. al, 1994) and secondary source). The study was performed according to OECD Guideline 301 D "Ready Biodegradability: Closed Bottle Test". Initial test substance conc. used in the study were 3, 10 and 30 mg/l, respectively. The percentage degradation of substance 6 -aminonaphthalene-1,3 -disulfonic acid was determined to be 0% by BOD parameter in 30 days. Thus, based on percentage degradation, 6 -aminonaphthalene-1,3 -disulfonic acid is considered to be not readily biodegradable in nature.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2016) for read across substance2-amino-5-methylbenzene sulfonic acid (CAS no. 88-44-8), biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance 2-amino-5-methylbenzene sulfonic acid. Concentration of inoculum i.e, activated 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 2-amino-5-methylbenzene sulfonic acid was determined to be <0 and 0% by BOD, O2 consumption, TOC removal, Test mat. analysis and UV-Vis parameter in 14 days. Thus, based on percentage degradation, 2-amino-5-methylbenzene sulfonic acid is considered to be not readily biodegradable in water.

 

On the basis of above results for target chemical sodium hydrogen 8-aminonaphthalene-1,6-disulfonate (from OECD QSAR toolbox version 3.4, 2017) and for its read across substance (from peer reviewed journals, secondary source and authoritative database J-CHECK), it can be concluded that the test substance sodium hydrogen 8 -aminonaphthalene-1,6 -disulfonate can be expected to be not readily biodegradable in nature.