2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)prop-1-enyl]-1,3,3-trimethyl-3H-indolium acetate

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 computational model developed by USEPA

Qualifier:

according to guideline

Guideline:

other: Modeling database

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:

no

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):

2.652 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.

Key result

Parameter:

other: Half-life

Value:

50

Sampling time:

2.652 mo

Remarks on result:

other: not readily biodegradable as estimated by BIOWIN model.

Details on results:

Biowin1 (Linear Model Prediction) : -0.0239: Does Not Biodegrade Fast
Biowin2 (Non-Linear Model Prediction): 0.0002: Does Not Biodegrade Fast
Biowin3 (Ultimate Biodegradation Timeframe): 1.5996: Recalcitrant
Biowin4 (Primary Biodegradation Timeframe): 2.6519: Weeks-Months
Biowin5 (MITI Linear Model Prediction) : -0.3988: Does Not Biodegrade Fast
Biowin6 (MITI Non-Linear Model Prediction): 0.0003: Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): -2.8859: Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO

BIOWIN (v4.10) Program Results:

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

SMILES : c12N(C)C(=CC=CC3=N(OC(=O)C)(C)c4ccccc4C3(C)C)C(C)(C)c1cccc2

CHEM : 3H-Indolium, 2-[3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-

propenyl]-1,3,3-trimethyl-, acetate

MOL FOR: C27 H32 N2 O2

MOL WT : 416.57

--------------------------- 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): Recalcitrant

Biowin4 (Primary Biodegradation Timeframe): Weeks-Months

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 | 2 | Carbon with 4 single bonds & no hydrogens | -0.1839 | -0.3679

Frag | 1 | Tertiary amine | -0.2053 | -0.2053

MolWt| * | Molecular Weight Parameter | | -0.1983

Const| * | Equation Constant | | 0.7475

============+============================================+=========+=========

RESULT | Biowin1 (Linear Biodeg Probability) | | -0.0239

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Carbon with 4 single bonds & no hydrogens | -1.7232 | -3.4464

Frag | 1 | Tertiary amine | -2.2229 | -2.2229

MolWt| * | Molecular Weight Parameter | | -5.9153

============+============================================+=========+=========

RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 0.0002

============+============================================+=========+=========

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 | 2 | Carbon with 4 single bonds & no hydrogens | -0.2121 | -0.4242

Frag | 1 | Tertiary amine | -0.2548 | -0.2548

MolWt| * | Molecular Weight Parameter | | -0.9206

Const| * | Equation Constant | | 3.1992

============+============================================+=========+=========

RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 1.5996

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Carbon with 4 single bonds & no hydrogens | -0.1534 | -0.3069

Frag | 1 | Tertiary amine | -0.2880 | -0.2880

MolWt| * | Molecular Weight Parameter | | -0.6010

Const| * | Equation Constant | | 3.8477

============+============================================+=========+=========

RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 2.6519

============+============================================+=========+=========

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 | 2 | Carbon with 4 single bonds & no hydrogens | 0.0676 | 0.1352

Frag | 1 | Tertiary amine | -0.0848 | -0.0848

Frag | 8 | Aromatic-H | 0.0082 | 0.0657

Frag | 7 | Methyl [-CH3] | 0.0004 | 0.0029

Frag | 3 | -C=CH [alkenyl hydrogen] | 0.0062 | 0.0186

Frag | 1 | Quaternary amine | -0.0093 | -0.0093

MolWt| * | Molecular Weight Parameter | | -1.2393

Const| * | Equation Constant | | 0.7121

============+============================================+=========+=========

RESULT | Biowin5 (MITI Linear Biodeg Probability) | | -0.3988

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE

------+-----+--------------------------------------------+---------+---------

Frag | 2 | Carbon with 4 single bonds & no hydrogens | 0.3990 | 0.7980

Frag | 1 | Tertiary amine | -0.8396 | -0.8396

Frag | 8 | Aromatic-H | 0.1201 | 0.9611

Frag | 7 | Methyl [-CH3] | 0.0194 | 0.1360

Frag | 3 | -C=CH [alkenyl hydrogen] | 0.0285 | 0.0855

Frag | 1 | Quaternary amine | 0.2550 | 0.2550

MolWt| * | Molecular Weight Parameter | |-12.0258

============+============================================+=========+=========

RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.0003

============+============================================+=========+=========

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 | 2 | Carbon with 4 single bonds & no hydrogens | -0.3342 | -0.6685

Frag | 1 | Tertiary amine | -1.0749 | -1.0749

Frag | 8 | Aromatic-H | -0.0954 | -0.7634

Frag | 7 | Methyl [-CH3] | -0.0796 | -0.5570

Frag | 3 | -C=CH [alkenyl hydrogen] | -0.0735 | -0.2206

Frag | 1 | Quaternary amine | -0.4377 | -0.4377

Const| * | Equation Constant | | 0.8361

============+============================================+=========+=========

RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | -2.8859

============+============================================+=========+=========

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:

no

Interpretation of results:

not readily biodegradable

Conclusions:

The biodegradability of the substance was calculated using seven different Biowin 1-7 models of the BIOWIN v4.10 software. The results indicate that test chemical is expected to be not readily biodegradable.

Executive summary:

Estimation Programs Interface Suite was run to predict the biodegradation potential of the test compound in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI LInear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1 -7, respectively) of the BIOWIN v4.10 software. The results indicate that test chemical is expected to be not readily biodegradable.

Description of key information

The biodegradability of the substance was calculated using seven different Biowin 1-7 models of the BIOWIN v4.10 software. The results indicate that test chemical is expected to be not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Type of water:

freshwater

Additional information

Following different studies includes estimated study for the target chemical and experimental study for read-across analogues which is extracted by using mechanistic approach and functionally and structurally similar to the target chemical to observe the biodegradation rate of test chemical in water.

Estimation Programs Interface Suite was run to predict the biodegradation potential of the test compound in the presence of mixed populations of environmental microorganisms. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI LInear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1 -7, respectively) of the BIOWIN v4.10 software. The results indicate that test chemical is expected to be not readily biodegradable.

In second study, aerobic biodegradation experiment was performed for read across chemical using activated sludge at concentration 0.5 g/L dry material as inoculums and initial concentration of chemical taken was 100 mg/L for 42 days. By considering DOC removal parameter read across chemical showed 16 % degradation in 42 days. The read across chemical belongs to D category according to table 1 and 2 as its limit value falls in that range. This percentage value is very less So it is concluded that test chemical is not readily biodegradable.

Last biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across chemical. Activated sludge was used as a test inoculums for the study. 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. After 14 days of incubation Percent biodegradation of read across chemical was observed to be 0% by BOD parameter and 0.7% by HPLC parameter. Thus, based on percentage degradation, read across chemical is considered to be not readily biodegradable in water.

Based on above observations, it is concluded that test chemical is not readily degradable in water.