3-hydroxy-4-[(2-methoxy-5-nitrophenyl)azo]-N-(3-nitrophenyl)naphthalene-2-carboxamide

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 3.3 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material : 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide
- Common name : 3-hydroxy-4-[(2-methoxy-5-nitrophenyl)azo]-N-(3-nitrophenyl)naphthalene-2-carboxamide, C.I. Pigment Red 23
- Molecular formula : C24H17N5O7
- Molecular weight : 487.4263 g/mol
- Smiles notation : c12c(c(c(cc1cccc2)C(=O)Nc1cc(ccc1)[N+](=O)[O-])O)/N=N/c1c(ccc(c1)[N+](=O)[O-])OC
- InChl : 1S/C24H17N5O7/c1-36-21-10-9-17(29(34)35)13-20(21)26-27-22-18-8-3-2-5-14(18)11-19(23(22)30)24(31)25-15-6-4-7-16(12-15)28(32)33/h2-13,30H,1H3,(H,25,31)/b27-26+
- 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:

0.2

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 0.2% 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 5 nearest neighbours
Domain  logical expression:Result: In Domain

((((("a" or "b" or "c" or "d" or "e" )  and "f" )  and "g" )  and "h" )  and ("i" and "j" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Non-covalent interaction AND Non-covalent interaction >> DNA intercalation AND Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain by DNA binding by OASIS v.1.3

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 >> Aromatic azo AND SN1 >> Nitrenium Ion formation >> Aromatic nitro by DNA binding by OECD

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides by Protein binding by OASIS v1.3

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 by Protein binding by OECD

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Amides AND Phenol Amines AND Phenols by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "f"

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

Domain logical expression index: "g"

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

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 5) ONLY

Domain logical expression index: "i"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 307 Da

Domain logical expression index: "j"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 520 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS no. 6471 -49 -4) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 0.2% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS no. 6471 -49 -4) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 0.2% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide 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 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS No. 6471-49-4) and 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 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide(CAS No. 6471-49-4) was estimated.Test substance undergoes 0.2% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamidewas estimated to be not readily biodegradable in water.

 

In another prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compound3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide(CAS No. 6471-49-4) in the presence of mixed populations of environmental microorganisms 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 chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamideis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 1-(4-Methyl-2-nitrophenylazo)-2-naphthol (CAS no. 2425-85-6),biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1-(4-Methyl-2-nitrophenylazo)-2-naphthol. 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 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol was determined to be 0 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,1 -(4 -Methyl-2 -nitrophenylazo)-2 –naphthol is considered to be not readily biodegradable in nature.

 

For the read across chemical Disperse Blue 143 (CAS no. 61968-28-3), biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance Disperse Blue 143 (J-CHECK, 2017 and EnviChem, 2014). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I). Activated sludge was used as a test inoculums for the study. 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 Disperse Blue 143 was determined to be 0 and 2.7% by BOD and HPLC parameter in 14 days. Thus, based on percentage degradation, Disperse Blue 143 is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK & EnviChem), it can be concluded that the test substance3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamidecan be expected to be not readily biodegradable in nature.