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EC number: 210-441-2 | CAS number: 615-66-7
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Biodegradation in water: screening tests
Administrative data
Link to relevant study record(s)
- Endpoint:
- biodegradation in water: ready biodegradability
- 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 predictive model developed by US EPA.
- Qualifier:
- no guideline available
- Principles of method if other than guideline:
- The Biodegradation Probability Program (BIOWIN) estimates the probability for the rapid aerobic biodegradation of an organic chemical in the presence of mixed populations of environmental microorganisms .The model is part of the EpiSuite program of the US-EPA. Estimations are made with BIOWIN version 4.10Estimates are based upon fragment constants that were developed using multiple linear and non-linear regression analyses. Experimental biodegradation data for the multiple linear and non-linear regressions were obtained from Syracuse Research Corporation's (SRC) data base of evaluated biodegradation data (Howard et. al., 1987). This version (v4.10) designates the models as follows (see also Boethling et al. 2003):
Biowin1 = linear probability model
Biowin2 = nonlinear probability model
Biowin3 = expert survey ultimate biodegradation model
Biowin4 = expert survey primary biodegradation model
Biowin5 = MITI linear model
Biowin6 = MITI nonlinear model
Biowin7 = anaerobic biodegradation model - GLP compliance:
- not specified
- Oxygen conditions:
- other: aerobic (Biowin 1-6) and anaerobic (Biowin 7)
- Inoculum or test system:
- other: mixed populations of environmental microorganisms
- Duration of test (contact time):
- 2.408 mo
- Details on study design:
- Using the computer tool BIOWIN v4.10 by US-EPA (EPIWIN) the aerobic as well as the anaerobic biodegradability of the test material can be estimated. The follwoing seven different models are used by the tool: Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI LInear Model, MITI Non-Linear Model and Anaerobic Model (calles Biowin 1-7, respectively). Due to this results the overall prediction of readily biodegradability is done for the desired chemical.
- Parameter:
- other: half-life
- Value:
- 50
- Sampling time:
- 2.408 mo
- Remarks on result:
- not readily biodegradable based on QSAR/QSPR prediction
- Details on results:
- - BIOWIN 1 - linear biodegradation prediction: 0.0297: Does Not Biodegrade Fast
- BIOWIN 2 - non-linear biodegradation prediction: 0.0078: Does Not Biodegrade Fast
- BIOWIN 3 - survey model ultimate biodegradation timeframe: 2.4076 Months
- BIOWIN 4 - survey model primary biodegradation timeframe: : 3.2599 Days-Weeks
- BIOWIN 5 - MITI linear biodegradation prediction: 0.0034: Does Not Biodegrade Fast
- BIOWIN 6 - MITI non-linear biodegradation prediction: -4.1164: Does Not Biodegrade Fast
- BIOWIN 7 - Anaerobic Linear biodegradation prediction: -0.4081: Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO - Validity criteria fulfilled:
- not specified
- Interpretation of results:
- not readily biodegradable
- Conclusions:
- Results from the BIOWIN evaluation of 2-chloro-p-phenylenediamine indicate that the chemical is not readily biodegradable.
- Executive summary:
Biodegradation, the degradation of a chemical substance by the action of microorganisms, is estimated by EPI Suite using seven models contained in BIOWIN. Version 4.10 designates these models as follows:
Probability of Rapid Biodegradation:
Biowin1: linear regression probability model
Biowin2: nonlinear regression probability model
Expert Survey Biodegradation:
Biowin3: expert survey ultimate biodegradation model
Biowin4: expert survey primary biodegradation model
MITI Biodegradation Probability:
Biowin5: MITI linear regression model
Biowin6: MITI nonlinear regression model
Anaerobic Biodegradation Probability
Biowin7: anaerobic biodegradation model
Biodegradability estimates made by these models are based on fragment constants that were developed
using multiple linear or non-linear regression analyses.
Results from the BIOWIN evaluation of 2-chloro-p-phenylenediamine indicate that the chemical is not readily biodegradable.
Reference
BIOWIN (v4.10) Program Results:
==============================
SMILES : Nc(c(cc(N)c1)CL)c1
CHEM : 1,4-Benzenediamine, 2-chloro-
MOL FOR: C6 H7 CL1 N2
MOL WT : 142.59
--------------------------- BIOWIN v4.10 Results ----------------------------
Biowin1 (Linear Model Prediction) : Does Not Biodegrade Fast
Biowin2 (Non-Linear Model Prediction): Does Not Biodegrade Fast
Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months
Biowin4 (Primary Biodegradation Timeframe): Days-Weeks
Biowin5 (MITI Linear Model Prediction) : Does Not Biodegrade Fast
Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin1 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 1 | Aromatic chloride [-CL] | -0.1824 | -0.1824
Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.2338 | -0.4675
MolWt| * | Molecular Weight Parameter | | -0.0679
Const| * | Equation Constant | | 0.7475
============+============================================+=========+=========
RESULT | Biowin1 (Linear Biodeg Probability) | | 0.0297
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 1 | Aromatic chloride [-CL] | -2.0155 | -2.0155
Frag | 2 | Aromatic amine [-NH2 or -NH-] | -1.9070 | -3.8140
MolWt| * | Molecular Weight Parameter | | -2.0248
============+============================================+=========+=========
RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 0.0078
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin3 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 1 | Aromatic chloride [-CL] | -0.2066 | -0.2066
Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.1349 | -0.2699
MolWt| * | Molecular Weight Parameter | | -0.3151
Const| * | Equation Constant | | 3.1992
============+============================================+=========+=========
RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 2.4076
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 1 | Aromatic chloride [-CL] | -0.1653 | -0.1653
Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.1084 | -0.2168
MolWt| * | Molecular Weight Parameter | | -0.2057
Const| * | Equation Constant | | 3.8477
============+============================================+=========+=========
RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 3.2599
============+============================================+=========+=========
Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks
(Primary & Ultimate) 2.00 -> months 1.00 -> longer
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin5 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 1 | Aromatic chloride [-CL] | 0.0062 | 0.0062
Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.1577 | -0.3154
Frag | 3 | Aromatic-H | 0.0082 | 0.0247
MolWt| * | Molecular Weight Parameter | | -0.4242
Const| * | Equation Constant | | 0.7121
============+============================================+=========+=========
RESULT | Biowin5 (MITI Linear Biodeg Probability) | | 0.0034
============+============================================+=========+=========
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 1 | Aromatic chloride [-CL] | -0.2191 | -0.2191
Frag | 2 | Aromatic amine [-NH2 or -NH-] | -1.2264 | -2.4527
Frag | 3 | Aromatic-H | 0.1201 | 0.3604
MolWt| * | Molecular Weight Parameter | | -4.1164
============+============================================+=========+=========
RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.0198
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable
A Probability Less Than 0.5 indicates --> NOT Readily Degradable
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin7 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 1 | Aromatic chloride [-CL] | -0.4023 | -0.4023
Frag | 2 | Aromatic amine [-NH2 or -NH-] | -0.2778 | -0.5556
Frag | 3 | Aromatic-H | -0.0954 | -0.2863
Const| * | Equation Constant | | 0.8361
============+============================================+=========+=========
RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | -0.4081
============+============================================+=========+=========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast
Ready Biodegradability Prediction: (YES or NO)
----------------------------------------------
Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey model) result is "weeks" or faster (i.e. "days", "days to weeks", or "weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then the prediction is YES (readily biodegradable). If this condition is not satisfied, the prediction is NO (not readily biodegradable). This method is based on application of Bayesian analysis to ready biodegradation data (see Help). Biowin5 and 6 also predict ready biodegradability, but for degradation in the OECD301C test only; using data from the Chemicals
Evaluation and Research Institute Japan (CERIJ) database.
Description of key information
Biodegradation, the degradation of a chemical substance by the action of microorganisms, is estimatedby EPI Suite using seven models contained in BIOWIN. Version 4.10 designates these models asfollows:
Probability of Rapid Biodegradation:
Biowin1: linear regression probability model
Biowin2: nonlinear regression probability model
Expert Survey Biodegradation:
Biowin3: expert survey ultimate biodegradation model
Biowin4: expert survey primary biodegradation model
MITI Biodegradation Probability:
Biowin5: MITI linear regression model
Biowin6: MITI nonlinear regression model
Anaerobic Biodegradation Probability
Biowin7: anaerobic biodegradation model
Biodegradability estimates made by these models are based on fragment constants that were developed
using multiple linear or non-linear regression analyses.
Results from the BIOWIN evaluation of 2-chloro-p-phenylenediamine indicate that the chemical is not readily biodegradable.
Key value for chemical safety assessment
- Biodegradation in water:
- inherently biodegradable
Additional information
The biodegradation potential of the test compound 2-chloro-p-phenylenediamine (CAS No. 615-66-7) was investigated to a greater or lesser extent. Various biodegradation studies for the target substance 2-chloro-p-phenylenediamine (CAS No. 615-66-7) and for its relevant read across substances such as 3 -chloroaniline (CAS No.- 108-42-9) and 2,4,6-trichloroaniline (CAS No. 634-93-5) by considering its structure-activity relationships, were reviewed and are summarized as follows:
The biodegradation potential of the test compound 2-chloro-p-phenylenediamine (CAS No. 615-66-7) in the presence of mixed populations of environmental microorga nisms, is estimated by Estimation Programs Interface Suite (EPI suite, 2017) using seven models contained in BIOWIN Version 4.10. Thus, results from the BIOWIN evaluation of 2-chloro-p-phenylenediamine indicate that the chemical is not readily biodegradable.
The above study is supported by the data from an authoritative database such as Japan chemicals collborative knowledge database (J-check, 2010), the biodegradat ion study was conducted for 28 days for evaluating the biodegradability potential of test substance 3 -chloroaniline (CAS No.- 108-42-9). 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 test substance was determined to be 1, 3 and 0% by BOD, TOC removal and HPLC parameters in 28 days. Thus, based upon the study it can be concluded that 3 -chloroaniline is not readily biodegradable in water.
Moreover, in a 28-days Manometric respirometry test following the OECD guideline 301F was conducted by SSS (2016) to determine the ready biodegradability of the test item 2,4,6-trichloroaniline (CAS No. 634-93-5). The test system included control, test item and reference item. The concentration of test and reference item (Sodium Benzoate) chosen for the study was 100mg/L, while that of inoculum was 10ml/l. ThOD (Theoretical oxygen demand) of test and reference item was determined by calculation. % Degradation was calculated using the values of BOD and ThOD for test item and reference item.
The BOD 28 value of 2,4,6-trichloroaniline (CAS No. 634-93-5) was observed to be 0.023 mgO2/mg. ThOD was calculated as 0.896 mgO2/mg. Accordingly, the % degradation of the test item after 28 days of incubation at 22 ± 2°C according to manometric respirometry test was found to be 2.57%.
Based on the results, the test item, under the test conditions, was found to be not readily biodegradable at 22 ± 2°C over a period of 28 days.
Based on the above predicted and experimental studies for target substance 2-chloro-p-phenylenediamine (CAS No. 615-66-7) and read across substances such as 3 -chloroaniline (CAS No.- 108-42-9) and 2,4,6-trichloroaniline (CAS No. 634-93-5) by applying weight of evidence approach, it is concluded that the test substance 2-chloro-p-phenylenediamine (CAS No. 615-66-7) is expected to be not readily biodegradable under test conditions.
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