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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.
Reference:
Composition 1
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
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material: C.I. Basic Violet 2 / (4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride)
- IUPAC name: 4-[(4-amino-3-methylphenyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline hydrochloride
- Molecular formula: C22H24ClN3
- Molecular weight: 365.906 g/mole
- Smiles :C(\c1cc(c(N)cc1)C)(c1cc(c(N)cc1)C)=C1\C=C(C(=[NH+])C=C1)C.[ClH-]
- Inchl: 1S/C22H23N3.ClH/c1-13-10-16(4-7-19(13)23)22(17-5-8-20(24)14(2)11-17)18-6-9-21(25)15(3)12-18;/h4-12,23H,24-25H2,1-3H3;1H
- Substance type: Organic
- Physical state: Solid Green crystalline powder
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:
4.796
Basis:
whole body w.w.
Calculation basis:
other: estimated
Remarks on result:
other: Bioaccumulative

BCFBAF Program (v3.01) Results:

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

SMILES : CC1=CC(C=CC1=N(H)(H))=C(c2ccc(N)c(C)c2)c3ccc(N)c(C)c3

CHEM : Benzenamine, 4-[(4-amino-3-methylphenyl)(4-imino-3-methyl-2,5-cyclohe

xadien-1-ylidene)methyl]-2-methyl-, monohydrochlor

MOL FOR: C22 H24 N3

MOL WT : 330.46

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

Summary Results:

Log BCF (regression-based estimate): 0.68 (BCF = 4.8 L/kg wet-wt)

Biotransformation Half-Life (days) : 0.0947 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 0.56 (BAF = 3.61 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 1.54

Equation Used to Make BCF estimate:

Log BCF = 0.6598 log Kow - 0.333 + Correction

Correction(s): Value

No Applicable Correction Factors

Estimated Log BCF = 0.681 (BCF = 4.796 L/kg wet-wt)

Validity criteria fulfilled:
not specified
Conclusions:
The bioconcentration factor (BCF) of 4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride (CAS No. 3248-91-7) was estimated to be 4.796 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 4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride (CAS No. 3248-91-7). The bioconcentration factor (BCF) of 2-amino-5-[(4-amino-3-sulfonatophenyl)(3-sulfocyclohexa-2,5-dien-1-ylidene)methyl]-3-methylbenzenesulfonate was estimated to be 4.796 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical  4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride  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 4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride (CAS No. 3248-91-7). The bioconcentration factor (BCF) of 2-amino-5-[(4-amino-3-sulfonatophenyl)(3-sulfocyclohexa-2,5-dien-1-ylidene)methyl]-3-methylbenzenesulfonate was estimated to be 4.796 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical  4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride  is not expected to bioaccumulate in the food chain.

Key value for chemical safety assessment

BCF (aquatic species):
4.796 L/kg ww

Additional information

Following different studies includes predicted data and experimental study for the target chemical and the structurally similar read across to conclude the bioaccumulation of 4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride (CAS No. 3248-91-7) in environment.

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride (CAS No. 3248-91-7). The bioconcentration factor (BCF) of 2-amino-5-[(4-amino-3-sulfonatophenyl)(3-sulfocyclohexa-2,5-dien-1-ylidene)methyl]-3-methylbenzenesulfonate was estimated to be 4.796 L/kg whole body w.w (at 25 deg C) which does not exceed the bioconcentration threshold of 2000, indicating that the chemical  4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride  is not expected to bioaccumulate in the food chain.

Similar estimation is done by ACD (Advanced Chemistry Development)/I-Lab predictive module Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor over the entire pH scale (pH 0 -14) of the test substance4-[(4-amino-3-methylphenyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline hydrochloride(CAS no. 3248 -91-7) was estimated to be in a range of 1 -17.1. This value indicates that the test substance4-[(4-amino-3-methylphenyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline hydrochloridewas considered to be non-accumulative in aquatic organisms.

Futher estimation 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 substance4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride (CAS No. 3248-91-7)was estimated to be 37.4 dimensionless . The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance

4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride

is non-bioaccumulative in nature.

The predicted data of the target chemical is supported by the strucurally similar read across Biphenyl-2-ylamine(CAS: 90-41-5) from J-CHECK indicating that the Bioaccumulation test of Biphenyl-2-ylamine was carried out in fish or shellfish. The bioconcentration factor (BCF) of Biphenyl-2-ylamine (CAS No. 90-41-5) is 10-30 L/kg at a concentration of 200 ppb(w/v) and 10-42 L/kg at a concentration of 20 ppb(w/v) which does not exceed the bio concentration threshold of 2000, indicating that the chemical is not expected to bioaccumulate in the food chain.

Another experimental study for the strucurally similar read across 4,4'-methylenedianiline (CAS: 101 -77 -9) from the publication Chemosphere 1994 and j-check suggests that the Bioaccumulation test was carried out on fish or shellfish to study the Bioaccumulation of 4,4'-methylenedianiline in environment. The bioconcentration factor (BCF) of 4,4'-methylenedianiline (CAS No. 101-77-9) is 3-14 L/kg at a concentration of0.2ppb(w/v) and 3.1-15 L/kg at a concentration of0.02ppb(w/v) which does not exceed the bio concentration threshold of 2000, indicating that the chemical is not expected to bioaccumulate in the food chain.

On the basis of above results for target chemical 4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride (CAS No. 3248-91-7) (from EPI suite, ACD LAB CompTox Chemistry Dashboard) and for its read across chemical (from J-CHeck 2017 and peer reviewed journal), and the value of BCF ranges from 1 to 42 which does not exceed the bio-concentration threshold of 2000, it can be concluded that the chemical 4-[(4-amino-m-tolyl)(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]-o-toluidine monohydrochloride  is not expected to be bioaccumulate in the food chain.