5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride

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 4.10. Estimates 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

Specific details on test material used for the study:

- Name of test material: 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride
- IUPAC name: 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride
- Molecular formula: C18H21N6Cl
- Molecular weight: 356.8589 g/mole
- Smiles : Cc1cn[n+](n1/N=N/c2ccc(cc2)N(C)Cc3ccccc3)C.[Cl-]
- Inchl: 1S/C18H21N6.ClH/c1-15-13-19-23(3)24(15)21-20-17-9-11-18(12-10-17)22(2)14-16-7-5-4-6-8-16;/h4-13H,14H2,1-3H3;1H/q+1;/p-1/b21-20+;
- Substance type: Organic
- Physical state: Solid powder

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):

1.93 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.

Biowin 1 and 2, are intended to convey a general indication of biodegradability under aerobic conditions, and not for any particular medium.
Biowin 1 (Linear model)
The fast biodegradation probability for any compound is calculated by summing, for all the fragments present in that compound, the fragment coefficient multiplied by the number of instances of the fragment in the compound (for MW, the value of that parameter is multiplied by its coefficient), and then adding this summation to the equation constant which is 0.7475. The summed values for each fragment coefficient multiplied by the number of instances appear in the "VALUE" column of the linear results screen.

Biowin 2 (Non-linear model)
Calculation of the fast biodegradation probability for any compound begins by summing, for all the fragments present in that compound, the fragment coefficient multiplied by the number of instances of the fragment in the compound (for MW, the value of that parameter is multiplied by its coefficient), then adding this summation to the equation constant which is 3.0087. The summed values for each fragment coefficient multiplied by the number of instances appear in the "VALUE" column of the non-linear results screen. The non-linear fast biodegradation probability is then calculated from the logistic equation as follows, where total = 3.0087 + the summation as described above:

Biowin 3 and 4 yield estimates for the time required to achieve complete ultimate and primary biodegradation in a typical or "evaluative" aquatic environment.

Biowin 5 and 6 are predictive models for assessing a compound’s biodegradability in the Japanese MITI (Ministry of International Trade and Industry) ready biodegradation test; i.e. OECD 301C. These models use an approach similar to that used to develop Biowin1 and 2. This protocol for determining ready biodegradability is among six officially approved as ready biodegradability test guidelines of the OECD (Organization for Economic Cooperation and Development). A total dataset of 884 chemicals was compiled to derive the fragment probability values that are applied in this MITI Biodegradability method. The dataset consists of 385 chemical that were critically evaluated as "readily degradable" and 499 chemicals that were critically evaluated as "not readily biodegradable".

Biowin 7, the anaerobic biodegradation model, is the most recent. As for the other Biowin models, multiple (linear) regression against molecular fragments was used to develop the model, which predicts probability of rapid degradation in the "serum bottle" anaerobic biodegradation screening test. This endpoint is assumed to be predictive of degradation in a typical anaerobic digester. Biowin7 estimates the probability of fast biodegradation under methanogenic anaerobic conditions; specifically, under the conditions of the "serum bottle" anaerobic biodegradation screening test (Meylan et al. 2007). A total of 169 compounds with serum bottle test data were identified for use in model development.

Out of seven different Biowin models, Biowin model 3 and 4 will help in estimating biodgeradability of the test chemical which was described as below-

Ultimate Biodegradation Timeframe and Primary Biodegradation Timeframe (Biowin 3 and 4)
These two models estimate the time required for "complete" ultimate and primary biodegradation.  Primary biodegradation is the transformation of a parent compound to an initial metabolite.  Ultimate biodegradation is the transformation of a parent compound to carbon dioxide and water, mineral oxides of any other elements present in the test compound, and new cell material. Then the rating was given to each model, which indicates the time required to achieve ultimate and primary biodegradation in a typical or "evaluative" aquatic environment. The ratings for each compound were averaged to obtain a single value for modeling.  The ultimate or primary rating of a compound is calculated by summing, for all the fragments present in that compound.

Key result

Parameter:

other: half life

Value:

50

Sampling time:

1.93 mo

Remarks on result:

other: not readily biodegradable as estimated by BIOWIN model

Details on results:

Biowin1 (Linear Model Prediction) : (0.4438) Does Not Biodegrade Fast
Biowin2 (Non-Linear Model Prediction): (0.0228) Does Not Biodegrade Fast
Biowin3 (Ultimate Biodegradation Timeframe): (1.9297) Months
Biowin4 (Primary Biodegradation Timeframe): (2.8806) Weeks
Biowin5 (MITI Linear Model Prediction) : (-0.3155) Does Not Biodegrade Fast
Biowin6 (MITI Non-Linear Model Prediction): (0.0006) Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): (-1.4222) Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO

BIOWIN (v4.10) Program Results:

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

SMILES : Cc1cnn(H)(n1N=Nc2ccc(cc2)N(C)Cc3ccccc3)CCL

CHEM :

MOL FOR: C18 H21 CL1 N6

MOL WT : 356.86

--------------------------- 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): Months

Biowin4 (Primary Biodegradation Timeframe): 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 | Aliphatic chloride [-CL] | -0.1114 | -0.1114

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

Frag | 1 | Alkyl substituent on aromatic ring | 0.0547 | 0.0547

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.1281 | 0.1281

MolWt| * | Molecular Weight Parameter | | -0.1699

Const| * | Equation Constant | | 0.7475

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

RESULT | Biowin1 (Linear Biodeg Probability) | | 0.4438

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

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

TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE

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

Frag | 1 | Aliphatic chloride [-CL] | -1.8528 | -1.8528

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

Frag | 1 | Alkyl substituent on aromatic ring | 0.5771 | 0.5771

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 1.7991 | 1.7991

MolWt| * | Molecular Weight Parameter | | -5.0674

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

RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 0.0228

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

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 | Aliphatic chloride [-CL] | -0.1732 | -0.1732

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

Frag | 1 | Alkyl substituent on aromatic ring | -0.0749 | -0.0749

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.0220 | 0.0220

MolWt| * | Molecular Weight Parameter | | -0.7886

Const| * | Equation Constant | | 3.1992

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

RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 1.9297

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

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

TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE

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

Frag | 1 | Aliphatic chloride [-CL] | -0.1006 | -0.1006

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

Frag | 1 | Alkyl substituent on aromatic ring | -0.0685 | -0.0685

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.0049 | 0.0049

MolWt| * | Molecular Weight Parameter | | -0.5149

Const| * | Equation Constant | | 3.8477

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

RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 2.8806

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

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 | Aliphatic chloride [-CL] | 0.0011 | 0.0011

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

Frag | 1 | Aromatic-CH3 | 0.0415 | 0.0415

Frag | 1 | Aromatic-CH2 | -0.0557 | -0.0557

Frag | 10 | Aromatic-H | 0.0082 | 0.0822

Frag | 1 | Methyl [-CH3] | 0.0004 | 0.0004

Frag | 1 | -CH2- [linear] | 0.0494 | 0.0494

MolWt| * | Molecular Weight Parameter | | -1.0617

Const| * | Equation Constant | | 0.7121

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

RESULT | Biowin5 (MITI Linear Biodeg Probability) | | -0.3155

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

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

TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE

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

Frag | 1 | Aliphatic chloride [-CL] | -0.6391 | -0.6391

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

Frag | 1 | Aromatic-CH3 | 0.3072 | 0.3072

Frag | 1 | Aromatic-CH2 | -0.1246 | -0.1246

Frag | 10 | Aromatic-H | 0.1201 | 1.2014

Frag | 1 | Methyl [-CH3] | 0.0194 | 0.0194

Frag | 1 | -CH2- [linear] | 0.4295 | 0.4295

MolWt| * | Molecular Weight Parameter | |-10.3021

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

RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.0006

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

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 | Aliphatic chloride [-CL] | -0.0147 | -0.0147

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

Frag | 1 | Alkyl substituent on aromatic ring | -0.1145 | -0.1145

Frag | 1 | Unsubstituted phenyl group (C6H5-) | 0.2182 | 0.2182

Frag | 1 | Aromatic-CH3 | -0.2573 | -0.2573

Frag | 1 | Aromatic-CH2 | -0.0073 | -0.0073

Frag | 10 | Aromatic-H | -0.0954 | -0.9543

Frag | 1 | Methyl [-CH3] | -0.0796 | -0.0796

Frag | 1 | -CH2- [linear] | 0.0260 | 0.0260

Const| * | Equation Constant | | 0.8361

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

RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | -1.4222

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

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

Validity criteria fulfilled:

not specified

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 the 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2) is expected to be not readily biodegradable.

Executive summary:

Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2) 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 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2) is expected to be not readily biodegradable.

Description of key information

Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2)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 that5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2) is expected to be not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Following studies include the predicted data and experimental study for the target chemical and structurally similar read acoss to conclude the extent of

5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2) towards Biodegradability in water is summarized as follows:

Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2) 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 that5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride (CAS: 29508-47-2) is expected to be not readily biodegradable.

Similar predicted data for the target chemical suggests that the Biodegradability of 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride  (CAS: 29508-47-2) is predicted using OECD QSAR toolbox version 3.3 with log Kow as the primary descriptor. Test substance undergoes 0.91 % degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 5-[[p-(benzylmethylamino)phenyl]azo]-1,4-dimethyl-1H-1,2,4-triazolium chloride  (CAS: 29508-47-2) was estimated to be not readily biodegradable in water.

The above predicted data of target chemical is supported by the experimental study of structurally similar read across C.I. Solvent Red 49 (CAS no. 509 -34 -2) from the authoritative database J-CHECK 2017, suggests that the Biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of test substance C.I. Solvent Red 49 (CAS no. 509 -34 -2). Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l. The percentage degradation of test substance was determined to be 0 and 1% degradation by BOD, TOC removal and HPLC in 28 days.  Thus, based on percentage degradation, C.I. Solvent Red 49 was considered to be not readily biodegradable in nature.

Another supporting experimental study for the structurally similar read across 4-(1-methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]aniline (CAS: 10081-67-1) from the authoritative database J-CHECK 2017, also suggests that the Biodegradation screening test was conducted for 28 days for evaluating the percentage biodegradability of the test substance.

Concentration of inoculum i.e, sludge is 30 mg/l and initial test substance conc. used in the study is 100 mg/l. The percentage degradation of test substance was found to be 0% by BOD, and 1% by HPLC. Thus, the substance 4-(1-methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]aniline (CAS: 10081 -67 -1) is non-biodegradable in water.