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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 1
Qualifier:
according to
Guideline:
OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))
Principles of method if other than guideline:
Prediction was done using OECD QSAR tool box v.3.4
GLP compliance:
not specified
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material: 5-acetamido-2-aminobenzenesulphonic acid
- IUPAC name: 2-amino-5-acetamidobenzene-1-sulfonic acid
- Molecular formula: C8H10N2O4S
- Molecular weight: 230.243 g/mole
- Smiles :O=C(Nc1ccc(N)c(S(=O)(=O)O)c1)C
- Inchl: 1S/C8H10N2O4S/c1-5(11)10-6-2-3-7(9)8(4-6)15(12,13)14/h2-4H,9H2,1H3,(H,10,11)(H,12,13,14)
- Substance type: Organic
- Physical state: Solid crystal powder (white to yellowish grey)
Oxygen conditions:
aerobic
Inoculum or test system:
other: Microorganisms
Duration of test (contact time):
28 d
Parameter followed for biodegradation estimation:
other: BOD
Key result
Parameter:
other: (BOD)
Value:
10.5
Sampling time:
28 d
Remarks on result:
other: other details not available
Details on results:
Perccent biodegradation of test chemical 5-acetamido-2-aminobenzenesulphonic acid estimated was 10.5 % by considering BOD as Parameter 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" or "e" )  and ("f" and ( not "g") )  )  and ("h" and ( not "i") )  )  and ("j" and "k" )  )

Domain logical expression index: "a"

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

Domain logical expression index: "b"

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

Domain logical expression index: "c"

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

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Acylation involving an activated (glucuronidated) carboxamide group AND Acylation >> Acylation involving an activated (glucuronidated) carboxamide group >> Carboxylic Acid Amides AND Acylation >> Direct acylation involving a leaving group AND Acylation >> Direct acylation involving a leaving group >> Carboxylic Acid Amides AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides AND AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> Carboxylic Acid Amides 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 Acylation AND Acylation >> Direct Acylation Involving a Leaving group AND Acylation >> Direct Acylation Involving a Leaving group >> Acetates by Protein binding by OECD

Domain logical expression index: "f"

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

Domain logical expression index: "g"

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 AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds OR AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds >> Four- and Five-Membered Lactones OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR No alert found OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> Coumarins OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide and Aminoalkylamine Side Chain OR Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines OR Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes OR Radical >> Generation of ROS by glutathione depletion (indirect) OR Radical >> Generation of ROS by glutathione depletion (indirect) >> Haloalkanes Containing Heteroatom OR Radical >> Radical mechanism via ROS formation (indirect) >> Amino Anthraquinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Coumarins OR Radical >> Radical mechanism via ROS formation (indirect) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitro Azoarenes 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 SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters 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 OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Amino Anthraquinones OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Fused-Ring Primary Aromatic Amines OR SN1 >> Nucleophilic attack after nitrenium ion formation >> p-Aminobiphenyl Analogs OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitro Azoarenes 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 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Acylation involving a leaving group after metabolic activation OR SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Haloalkanes Containing Heteroatom OR SN2 >> Alkylation, ring opening SN2 reaction OR SN2 >> Alkylation, ring opening SN2 reaction >> Four- and Five-Membered Lactones OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Coumarins OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Vicinal Dihaloalkanes OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) >> Vicinal Dihaloalkanes OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Haloalkanes Containing Heteroatom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives 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: "h"

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

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 222 Da

Domain logical expression index: "k"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 338 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
not readily biodegradable
Conclusions:
Percent biodegradation of test chemical 5-acetamido-2-aminobenzenesulphonic acid estimated was 10.5 % by considering BOD as parameter and microorganisms as inoculum in 28 days. Therefore it is concluded that test chemical 5-acetamido-2-aminobenzenesulphonic acid is not readily biodegradable.
Executive summary:

Biodegradability of test chemical 5-acetamido-2-aminobenzenesulphonic acid (CAS no. 96-78-6) is predicted using OECD QSAR tool box v.3.4 using log Kow as primary descriptor. Percent biodegradation of test chemical 5-acetamido-2-aminobenzenesulphonic acid estimated was 10.5 % by considering BOD as parameter and microorganisms as inoculum in 28 days. Therefore it is concluded that test chemical 5-acetamido-2-aminobenzenesulphonic acid is not readily biodegradable.

Description of key information

Biodegradability of test chemical 5-acetamido-2-aminobenzenesulphonic acid (CAS no. 96-78-6) is predicted using OECD QSAR tool box v.3.4 using log Kow as primary descriptor. Percent biodegradation of test chemical 5-acetamido-2-aminobenzenesulphonic acid estimated was 10.5 % by considering BOD as parameter and microorganisms as inoculum in 28 days. Therefore it is concluded that test chemical 5-acetamido-2-aminobenzenesulphonic acid is not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:
under test conditions no biodegradation observed

Additional information

Predicted data for the target compound 5-acetamido-2-aminobenzenesulphonic acid (CAS No: 96-78-6) and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below.

Biodegradability of test chemical 5-acetamido-2-aminobenzenesulphonic acid (CAS no. 96-78-6) is predicted using OECD QSAR tool box v.3.4 using log Kow as primary descriptor. Percent biodegradation of test chemical 5-acetamido-2-aminobenzenesulphonic acid estimated was 10.5 % by considering BOD as parameter and microorganisms as inoculum in 28 days. Therefore it is concluded that test chemical 5-acetamido-2-aminobenzenesulphonic acid is not readily biodegradable.

 

Another prediction done by using Estimation Programs Interface Suite (EPI suite, 2017) to predict the biodegradation potential of the test chemical 5-acetamido-2-aminobenzenesulphonic acid (CAS No: 96 -78 -6) in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical 5-acetamido-2-aminobenzenesulphonic acid is not readily biodegradable.

 

In a supporting weight of evidence study for read across chemical 3-Aminobenzene sulphonic acid (CAS no. 121-47-1) from authoritative database (J Check, 2017) biodegradation test was conducted by taking sludge as inoculums at 30 mg/L concentration. Biodegradation was analyzed by using three parameters that are O2 consumption (BOD), TOC removal and test material analysis by UV vis. The initial concentration of read across chemical was 100 mg/L and equipment used in the study used was of standard type. After 4 weeks read across chemical showed 1.1 % degradation by O2 Consumption (BOD) parameter and less than 0.0 % degradation by both TOC removal and Test material analysis by UV vis parameter so it is concluded that read across chemical 3-Aminobenzene sulphonic acid is not readily biodegradable.

 

In another supporting weight of evidence study for read across chemical 2-amino-5-methylbenzene sulfonic acid (CAS no. 88-44-8) from same source as mentioned above (J Check, 2017) biodegradation experiment was performed by taking activated sludge as inoculums at 30 mg/L concentration. Biodegradation was analyzed by using three parameters that are O2 consumption (BOD), TOC removal and test material analysis by UV vis. The initial concentration of read across chemical was 100 mg/L and equipment used in the study was of standard type. After 2 weeks read across chemical showed 0.0 % degradation by O2 Consumption (BOD) parame ter and less than 0.0 % degradation by both TOC removal and Test material analysis by UV vis parameter so it is concluded that read across chemical 2-amino-5-methylbenzene sulfonic acid is not readily biodegradable.

 

On the basis of above results for target chemical 5-acetamido-2-aminobenzenesulphonic acid (CAS No: 96-78-6) (from OECD QSAR tool box v3.4 and EPI suite, 2017) and for its read across substance (from authoritative database), it is concluded that the test substance 5-acetamido-2-aminobenzenesulphonic acid (CAS No: 96-78-6) can be expected to be not readily biodegradable in nature.