1-(3-chlorophenyl)-4-(3-chloropropyl)piperazinium 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

Oxygen conditions:

other: aerobic (Biowin 1-6) and anaerobic (Biowin 7)

Inoculum or test system:

other: mixed populations of environmental microorganisms

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

Remarks on result:

other: not readily biodegradable as estimated by BIOWIN model

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 test chemical is expected to be not readily biodegradable.

Executive summary:

Estimation Programs Interface Suite (2018) was run to predict the biodegradation potential of the test chemical 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

Estimation Programs Interface Suite (2018) was run to predict the biodegradation potential of the test chemical 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.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data of the test chemical and various supporting studies for its functionally similar read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done using Estimation Programs Interface Suite (2018), the biodegradation potential of the test chemical in the presence of mixed populations of environmental microorganisms was predicted. 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 a supporting weight study from authoritative database (J-CHECK, 2018) and secondary source (OECD SIDS, 2003), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of test chemical. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I) under aerobic conditions at a temperature of 25°C, respectively. Activated sludge was used as a test inoculums for the study. Fresh sludge samples were collected from ten sites in Japan, such as municipal sewage-treatment plants, rivers, lakes and seas. The filtered supernatant of an activated sludge (cultivated sludge for 3 months) were mixed with an equal volume of the filtered supernatant of freshly collected ten-source mixture when used. And the activated sludge were cultivated for OECD TG 301C.Thirty mg of the test substance or aniline (reference substance) and 9 mg as MLSS (mixed liquor suspended solid) of activated sludge were added to 300 ml of test medium (OECD TG 301C).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. A volume of mixture was 300 ml. The test and reference solutions were cultivated in BOD meter together with the inoculum blank and abiotic control ones at 25 deg C for 28 days, during which the oxygen consumption was continuously measured. After termination of the test, the residual amount of the test substance and DOC (dissolved organic carbon) were determined individually with HPLC and TOC meter. And pH values of test solutions were measured. The biodegradability was calculated from the oxygen consumption and the residual amount. Aniline was used as a reference substance for the study. Test chemical was not detected at both water plus test substance and sludge plus test substance solutions after 28 days. In water plus test substance solutions, o-chlorobenzyl alcohol was detected by LC-MS after 28 days. Production rate of o-chlorobenzyl alcohol was 99% from the measurement by HPLC. Therefore, it is considered that test chemical hydrolyzed into o-chlorobenzyl alcohol. In sludge plus test substance solutions, o-chlorobenzyl alcohol, o-chlorobenzaldehyde and o-chlorobenzoic acid were detected respectively after 28 days. Mean production rates of o-chlorobenzyl alcohol, o-chlorobenzaldehyde and o-chlorobenzoic acid were 92, 2 and 3 % respectively. Consequently it is considered that test chemical is hydrolyzed and produces o-chlorobenzyl alcohol, and then the o-chlorobenzyl alcohol is slowly biodegradable to o-chlorobenzaldehyde and o-chlorobenzoic acid. Degradation pathway of test chemical is as follows: o-chlorobenzyl alcohol, o-chlorobenzaldehyde, o-chlorobenzoic acid. The percentage degradation of test chemical was determined to be 0 and 100% by BOD, TOC removal and HPLC parameter in 28 days. The test chemical formed o-Chlorobenzyl alcohol, o-Chlorobenzaldehyde and o-Chlorobenzoic acid in the test solution. Thus, based on percentage degradation (0% by BOD), test chemical is considered to be not readily biodegradable in nature.

 

Another biodegradation studywas conducted for 28 days for evaluating the percentage biodegradability of test chemical. The study was performed according to Zahn-Wellns test under aerobic conditions at a temperature of25°C, respectively. Sludge was used as a test inoculums for the study. Concentration of inoculum i.e, sludge used was 200 mg/l and initial test substance conc. used in the study was 160 mg/l, respectively. The percentage degradation of test chemical was determined to be 0% by after a period of 28 days. Thus, based on percentage degradation, test chemical is considered to be not readily biodegradable in nature.

 

On the basis of above overall results of test chemical, it can be concluded that the test chemical can be considered to be not readily biodegradable in nature.