2-(4-aminoanilino)-5-nitrobenzenesulphonic acid

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:

equivalent or similar 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: 2-[(4-aminophenyl) amino]-5-nitrobenzenesulfonic acid
- Molecular formula: C12H11N3O5S
- Molecular weight: 309.301 g/mol
- Smiles notation : O=S(=O)(O)c1c(Nc2ccc(N)cc2)ccc([N+]([O])=O)c1
- InChl : 1S/C12H11N3O5S/c13-8-1-3-9(4-2-8)14-11-6-5-10(15(16)17)7-12(11)21(18,19)20/h1-7,14H,13H2,(H,18,19,20)
- Substance type: Organic
- Physical Appearance: 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:

0.967

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 0.966% 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" )  and "d" )  and "e" )  and ("f" and ( not "g") )  )  and "h" )  and ("i" and ( not "j") )  )  and ("k" and "l" )  )

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 SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Primary aromatic amine by DNA binding by OECD

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 days - weeks by Biodeg primary (Biowin 4) ONLY

Domain logical expression index: "e"

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

Domain logical expression index: "f"

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

Domain logical expression index: "g"

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

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Very fast by Bioaccumulation - metabolism half-lives ONLY

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Anilines (Hindered) OR Phenol Amines OR Phenols, Poly OR Salt by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "k"

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

Domain logical expression index: "l"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 371 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical 2-[(4-aminophenyl)amino]-5-nitrobenzenesulfonic acid was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 2-[(4-aminophenyl)amino]-5-nitrobenzenesulfonic acid (CAS no. 91 -29 -2) is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 0.966% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 2 -[(4 -aminophenyl)amino]-5 -nitrobenzenesulfonic acid was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 2-[(4-aminophenyl)amino]-5-nitrobenzenesulfonic acid (CAS no. 91 -29 -2) is predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 0.966% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 2 -[(4 -aminophenyl)amino]-5 -nitrobenzenesulfonic acid 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

Various predicted data for the target compound 2-[(4-aminophenyl)amino]-5-nitrobenzenesulfonic acid (CAS No. 91-29-2) and 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 2 -[(4 -aminophenyl)amino]-5 -nitrobenzenesulfonic acid(CAS No. 91-29-2) was estimated.Test substance undergoes 0.966% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 2 -[(4 -aminophenyl)amino]-5 -nitrobenzenesulfonic acid was estimated to be not readily biodegradable in water.

 

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 2 -[(4 -amino phenyl)amino]-5 -nitrobenzenesulfonic acid(CAS No. 91-29-2) was estimated.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  2-[(4-aminophenyl)amino]-5-nitrobenzenesulfonic acid is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 2­aminonaphthalene-1-sulfonic acid (CAS no. 81-16-3), read across chemical 2-aminonaphthalene-1-sulfonic acid was tested for biodegradability in water by taking activated sludge as a inoculums at 30 mg/L concentration . Biodegradation was analyzed by using four parameters BOD, TOC, UV-Vis and HPLC. The initial concentration of test chemical was 100 mg/L and study design was of standard type. After 2 weeks( 14 days) test chemical showed 3.8% , 0.7 % , 0 % and 5.8% biodegradation by BOD, TOC, UV-Vis and HPLC parameters respectively so it is concluded that the chemical 2-aminonaphthalene-1-sulfonic acid is not readily biodegradable.

 

For the read across chemical 2,2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid) (CAS no. 81-11-8), The read across chemical 2, 2'-ethene-1,2 -diylbis(5 -aminobenzenesulfonic acid) was subjected to biodegradation test by taking activated sludge as a inoculums at 30 mg/L concentration . Biodegradation was analysed by using two parameters BOD and HPLC. The initial concentration of test chemical was 100 mg/L and study design is of standard type. After 4 weeks (28 days) chemical showed 0% and 2 % biodegradation by BOD and test chemical concentration HPLC parameters respectively so it is concluded that it is not readily biodegradable.

 

On the basis of above results for target chemical 2-[(4-aminophenyl)amino]-5-nitrobenzenesulfonic acid(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, 2017), it can be concluded that the test substance 2-[(4-aminophenyl)amino]-5-nitrobenzenesulfonic acidcan be expected to be not readily biodegradable in nature.