2-[(4-chloro-2-nitrophenyl)azo]-N-(4-ethoxyphenyl)-3-oxobutyramide

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 (IUPAC name): 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide
- Molecular formula: C18H17ClN4O5
- Molecular weight: 404.808 g/mol
- Smiles notation: O=C(Nc1ccc(OCC)cc1)[C@@H](\N=N\c1c([N+](=O)[O-])cc(cc1)Cl)C(=O)C
- InChl: 1S/C18H17ClN4O5/c1-3-28-14-7-5-13(6-8-14)20-18(25)17(11(2)24)22-21-15-9-4-12(19)10-16(15)23(26)27/h4-10,17H,3H2,1-2H3,(H,20,25)/b22-21+
- Substance type: Organic
- Physical state: Solid

Oxygen conditions:

aerobic

Inoculum or test system:

other: Micro-organisms

Duration of test (contact time):

28 d

Based on:

not specified

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

5.275

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 5.3% 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" and ("b" and ( not "c") )  )  and "d" )  and ("e" and "f" )  )

Domain logical expression index: "a"

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

Domain logical expression index: "b"

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

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Moderate binder, NH2 group OR Non binder, impaired OH or NH2 group OR Non binder, MW>500 OR Non binder, non cyclic structure OR Strong binder, OH group OR Weak binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "d"

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

Domain logical expression index: "e"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 218 Da

Domain logical expression index: "f"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 408 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (CAS no. 52320 -66 -8) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (CAS no. 52320 -66 -8) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide 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-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide(CAS No. 52320-66-8) and supporting weight of evidence studies for its structurally similar 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 chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4-ethoxyphenyl)-3-oxobutanamide(CAS No. 52320-66-8) was estimated.Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamidewas 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 compound 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide(CAS No. 52320-66-8) 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 chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3-oxobutanamideis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK & HSDB, 2017 and EnviChem, 2014) for the read across chemical 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl) didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) (CAS no. 6358-85-6),biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). 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 2,2'-[(3,3'-dichlorobiphenyl- 4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) was determined to be 0% by BOD parameter in 14 days. Thus, based on percentage degradation, 2,2'-[(3,3'-dichloro biphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of test substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) (CAS no. 6358-85-6) (OECD SIDS, 2003). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)) under aerobic conditions at a temperature of 25°C. 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 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) was determined to be 0% by BOD and UV-Vis parameter in 14 days. Thus, based on percentage degradation, 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB & EnviChem and secondary source OECD SIDS), it can be concluded that the test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamidecan be expected to be not readily biodegradable in nature.