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Environmental fate & pathways

Bioaccumulation: aquatic / sediment

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Reference
Endpoint:
bioaccumulation in aquatic species, other
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Estimated data generated using the EPI Suite program developed by the USEPA.
Qualifier:
according to
Guideline:
other: Modeling database
Principles of method if other than guideline:
Prediction done using BCFBAF (v3.01) model
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
Radiolabelling:
not specified
Vehicle:
not specified
Test organisms (species):
other: Fish
Route of exposure:
aqueous
Test type:
not specified
Water / sediment media type:
natural water: freshwater
Test temperature:
25 deg.C
Reference substance (positive control):
not specified
Key result
Temp.:
25 °C
Type:
BCF
Value:
10 L/kg
Basis:
whole body w.w.
Calculation basis:
other: estimated
Remarks on result:
other: Non-bioaccumulative

BCFBAF Program (v3.01) Results:

==============================

SMILES : O=C(Nc2ccc(OCC)cc2)C(N=Nc1c(N(=O)(=O))cc(cc1)CL)C(=O)C

CHEM :

MOL FOR: C18 H17 CL1 N4 O5

MOL WT : 404.81

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

Log BCF (regression-based estimate): 1.00 (BCF = 10 L/kg wet-wt)

Biotransformation Half-Life (days) : 0.484 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 2.29 (BAF = 195 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 4.61

Equation Used to Make BCF estimate:

Log BCF = 1.00 { Aromatic Azo Specification }

Correction(s): Value

Aromatic Azo compound 0.000

Estimated Log BCF = 1.000 (BCF = 10 L/kg wet-wt)

Validity criteria fulfilled:
not specified
Conclusions:
The bioconcentration factor (BCF) of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical is not expected to bioaccumulate in the food chain.
Executive summary:

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl) diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The bioconcentration factor (BCF) of 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.

Description of key information

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl) diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The bioconcentration factor (BCF) of 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.

Key value for chemical safety assessment

BCF (aquatic species):
10 L/kg ww

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 study for its structurally similar read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In aprediction done using the BCFBAF Program(v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The bioconcentration factor (BCF) of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.

 

In an another prediction done by using Bio-concentration Factor (v12.1.0.50374) moduleACD (Advanced Chemistry Development)/I-Lab predictive module, 2017), theBio-concentration Factor (BCF) of the test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (CAS no. 52320 -66 -8) was estimated to be 8897, 11660, 12007, 11778, 9645, 3446, 496, 86.8, 44.2, 40.0, 39.5, 39.3 and 38.1 at pH range 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10-12, 13 and 14, respectively. This value (86.8 at pH 7.0) indicates that the test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was considered to be non-accumulative in aquatic organisms.

 

Bioconcentration Factor (BCF) of test chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 489.98 at pH 5.5 and 4.10 at pH 7.4, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.

 

Another predicted data was estimated using Scifinder database (American Chemical Society (ACS), 2017) was used for predicting the bioconcentration factor (BCF) of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The bioconcentration factor (BCF) of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 3290, 3400, 3410, 3350, 2860, 1170, 178, 28.4, 12.6 and 11.0 (at 25 deg C) at pH range 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10, respectively which does not exceed the bio concentration threshold of 2000 at pH 7.0, indicating that the chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the bioaccumulation i.e BCF for test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 52.9 dimensionless . The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide is non-bioaccumulative in nature.

 

In a supporting weight of evidence study from authoritative database (J-CHECK & HSDB, 2017 and EnviChem, 2014) and secondary source (OECD SIDS, 2003) 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),bioaccumulation experiment was conducted on test organism Cyprinus carpio for 6 weeks for evaluating the bioconcentration factor (BCF value) of 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) (CAS no. 6358-85-6).The study was performed according to other guideline "Bioaccumulation test of a chemical substance in fish or shellfish" provided in "the Notice on the Test Method Concerning New Chemical Substances", respectively. Cyprinus carpio was used as a test organism for the study. Test chemical nominal conc. used for the study were 0.1mg/l and 0.01 mg/l, respectively. Test chemical solution was prepared in HCO-40 or crystal sugar. Analytical method involve therecovery ratio:Test water : 1st concentration area : 94.2 %, 2nd concentration area : 100 %, Fish : 80.7 %, - Limit of detection : Fish : 0.0186 ppm. Range finding study involve the TLm (48 hr) ≥ 420 mg/l (w/v) on Rice fish (Oryzias latipes). Lipid content of the test organism was determined to be 2.8%. The bioconcentration factor (BCF value) of substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) on Cyprinus carpio was determined to be in the range of 0.38 – 3.2 L/Kg at a conc. of 0.1 mg/l and 2.4 – 5.4 L/Kg at a conc. of 0.01 mg/l, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) is not expected to bioaccumulate in the food chain.

 

On the basis of above results for target chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database and secondary source), it can be concluded that the BCF value of test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide ranges from 4.10 – 178 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.