2-chloro-p-phenylenediamine

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

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

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.

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.

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.