4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

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:

Data is from computational model developed by USEPA

Qualifier:

according to guideline

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: 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid / Acid Yellow 49
- IUPAC name: 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid
- Molecular formula: C16H13Cl2N5O3S
- Molecular weight: 426.283 g/mole
- Smiles :n1(c2ccccc2)c(c(\N=N\c2c(cc(S(O)(=O)=O)c(c2)Cl)Cl)c(n1)C)N
- Inchl: 1S/C16H13Cl2N5O3S/c1-9-15(16(19)23(22-9)10-5-3-2-4-6-10)21-20-13-7-12(18)14(8-11(13)17)27(24,25)26/h2-8H,19H2,1H3,(H,24,25,26)/b21-20+
- Substance type: Organic
- Physical state: Solid powder (yellow)

Radiolabelling:

not specified

Vehicle:

not specified

Test organisms (species):

other: Fish

Route of exposure:

aqueous

Test type:

other: estimation

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:

3.162 L/kg

Basis:

whole body w.w.

Calculation basis:

other: estimated

Remarks on result:

other: Non-bioaccumulative

BCFBAF Program (v3.01) Results:

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

SMILES : n1(c3ccccc3)c(c(N=Nc2c(cc(S(O)(=O)=O)c(c2)CL)CL)c(n1)C)N

CHEM :

MOL FOR: C16 H13 CL2 N5 O3 S1

MOL WT : 426.28

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

Summary Results:

Log BCF (regression-based estimate): 0.50 (BCF = 3.16 L/kg wet-wt)

Biotransformation Half-Life (days) : 0.0761 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 0.65 (BAF = 4.5 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 1.70

Equation Used to Make BCF estimate:

Log BCF = 0.50 (Ionic; Log Kow dependent)

Estimated Log BCF = 0.500 (BCF = 3.162 L/kg wet-wt)

Validity criteria fulfilled:

not specified

Conclusions:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS No. 12239-15-5) is 3.162 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid is non bioaccumulative in food chain.

Executive summary:

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) is 3.162 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid is non bioaccumulative in food chain.

Description of key information

Using BCFBAF Program (v3.00) model of EPI suite (2017) the estimated bio concentration factor (BCF) for 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) is 3.162 L/kg wet-wt at 25 deg. c which does not exceed the bioconcentration threshold of 2000. Therefore it is concluded that test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid is non bioaccumulative in food chain.

Key value for chemical safety assessment

BCF (aquatic species):

3.162 L/kg ww

Additional information

Predicted data studies for target chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) and experimental study for its structurally similar read across chemical have been conducted and their results are summarized below for bioaccumulation endpoint.

First weight of evidence study was by done using BCFBAF Program (v3.00) model of Estimation Program Interface (EPI suite 2017) the estimated bio concentration factor (BCF) for 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) is 3.162 L/kg wet-wt at 25 deg. c

Next weight of evidence study was done by using Bio-concentration Factor (v12.1.0.50374) module of Advanced Chemistry Development/ I-lab predictive module (2017) in this study the bio-concentration Factor at range pH 1-14  of the chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS no.12239 -15 -5) estimated to be 1.0 dimensionless.

Third weight of evidence study was done by using Scifinder database of American chemical Society (ACS 2017) in this  study the Bioconcentration factor (BCF) for test chemical  4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS No: 12239-15-5) was predicted in aquatic organisms by at pH 1-10 and temperature 25 °C .The Bioconcentration factor (BCF) of test substance 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid at pH 1-10 and temperature 25 °C was estimated to be 1.0 dimensionless.

 

Fourth weight of evidence study was done by using Chemspider- ACD/PhysChem Suite of Royal society of Chemistry (RCS, 2017) in this study the Bioconcentration factor (BCF) of test substance 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid at pH 5.5 and pH 7.4 was estimated to be 1.0 dimensionless. This BCF value suggests that the test chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid is non bioaccumulative in aquatic organisms.

Next weight of evidence study was done 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 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid (CAS no.12239 -15 -5) was estimated to be 16.8 dimensionless . The predicted BCF result was based on the 5 OECD principles.

 Last weight of evidence study was done from authoritative database ( Jcheck, 2017) in this study the bioaccumulation test was conducted for 6 weeks for determination the bioconcentration factor (BCF) of read across chemical 2,5-dichloro-4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonic acid (CAS no 84-57-1) on test organism Cyprinus carpio. Recovery ratio of Test water was 102 %, Fish : 61.0 %, - Limit of detection : Test water : 1st concentration area : 0.095 microg/mL, 2ndconcentration area : 0.0095 microg/mL, Fish : 5.5 microg/g .Nominal concentrations used was 1st Concentration area: 2.0 mg/L (w/v), 2nd Concentration area: 0.2 mg/L (w/v) and range finding study was carried out on Rice fish (Oryzias latipes) LC50(48h) 434 mg/L. The lipid content of fish was 3.8 % at start of exposure. Thus according to static fish test the bioconcentration factor (BCF) for read across chemical 2,5-dichloro-4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonic acid was determined according static fish test. The BCF value was observed to be 2.8 L/kg at dose concentration 2 mg/L and ≤ 32 L/kg at dose concentration 0.2 mg/L on test organism Cyprinus carpio during 6 weeks period. Therefore it is concluded that read across chemical 2,5-dichloro-4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonic acid is nonbioaccumulative in fish and food chain as these values are far less than 2000 criteria.

On the basis of above results for target chemical 4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5) (from EPI suite, ACD labs, Sci Finder database, Chemspider and CompTox Chemistry Dashboard 2017) and for its read across chemicals (From J check) it can be concluded that the BCF value of test substance4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  ranges from 1 to 16.8 dimensionless which does not exceed the bioconcentration threshold of 2000, indicating that the chemical4-[(5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)azo]-2,5-dichlorobenzenesulphonic acid  (CAS No. 12239-15-5)is expected to be nonbioaccumulative in the food chain.