Reaction mass of N,N-ethanediylbis- Hexadecanamide, N-[2-[(1-oxohexadecyl)amino]ethyl]-Octadecanamide, Hexadecanoic acid, 12-hydroxystearic acid, reaction products with ethylenediamine, N,N-ethanediylbis-Octadecanamide and Octadecanoic acid, 12-hydroxystearic acid, reaction products with ethylenediamine

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: screening tests

Type of information:

calculation (if not (Q)SAR)

Remarks:

Migrated phrase: estimated by calculation

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Scientifically acceptable calculation

Principles of method if other than guideline:

BIOWIN v4.10

Details on inoculum:

BIOWIN v4.10 calculation

BIOWIN (v4.10) Program Results:

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

SMILES : O=C(NCCNC(=O)CCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCC

CHEM  : Octadecanamide, N,N -1,2-ethanediylbis-

MOL FOR: C38 H76 N2 O2

MOL WT : 593.04

--------------------------- BIOWIN v4.10 Results ----------------------------

 

Biowin1 (Linear Model Prediction)   : Biodegrades Fast

Biowin2 (Non-Linear Model Prediction): Biodegrades Fast

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months

Biowin4 (Primary Biodegradation Timeframe): Days

Biowin5 (MITI Linear Model Prediction)   : Biodegrades Fast

Biowin6 (MITI Non-Linear Model Prediction): Biodegrades Fast

Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast

Ready Biodegradability Prediction: NO

 

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

TYPE | NUM |      Biowin1 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Linear C4 terminal chain [CCC-CH3]      | 0.1084 | 0.2169

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | 0.2102 | 0.4203

MolWt| * | Molecular Weight Parameter               |        | -0.2823

Const| * | Equation Constant                        |        | 0.7475

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

RESULT  |   Biowin1 (Linear Biodeg Probability)    |        | 1.1024

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

 

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

TYPE | NUM |      Biowin2 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Linear C4 terminal chain [CCC-CH3]      | 1.8437 | 3.6874

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | 2.6913 | 5.3826

MolWt| * | Molecular Weight Parameter               |        | -8.4212

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

RESULT  | Biowin2 (Non-Linear Biodeg Probability)  |        | 0.9749

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

 

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 | Linear C4 terminal chain [CCC-CH3]      | 0.2983 | 0.5967

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | -0.0542 | -0.1084

MolWt| * | Molecular Weight Parameter               |        | -1.3105

Const| * | Equation Constant                        |        | 3.1992

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

RESULT  | Biowin3 (Survey Model - Ultimate Biodeg) |        | 2.3769

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

 

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

TYPE | NUM |      Biowin4 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Linear C4 terminal chain [CCC-CH3]      | 0.2691 | 0.5381

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | 0.2054 | 0.4109

MolWt| * | Molecular Weight Parameter               |        | -0.8556

Const| * | Equation Constant                        |        | 3.8477

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

RESULT  |  Biowin4 (Survey Model - Primary Biodeg) |        | 3.9411

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

 

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 | Amide  [-C(=O)-N or -C(=S)-N]          | 0.1266 | 0.2533

Frag | 2 | Methyl [-CH3]                           | 0.0004 | 0.0008

Frag | 34 | -CH2- [linear]                          | 0.0494 | 1.6801

MolWt| * | Molecular Weight Parameter               |        | -1.7643

Const| * | Equation Constant                        |        | 0.7121

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

RESULT  | Biowin5 (MITI Linear Biodeg Probability) |        | 0.8821

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

 

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

TYPE | NUM |      Biowin6 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | 0.8859 | 1.7717

Frag | 2 | Methyl [-CH3]                           | 0.0194 | 0.0389

Frag | 34 | -CH2- [linear]                          | 0.4295 | 14.6028

MolWt| * | Molecular Weight Parameter               |        |-17.1204

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

RESULT  |Biowin6 (MITI Non-Linear Biodeg Probability)|        | 0.8604

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

 

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 | Linear C4 terminal chain [CCC-CH3]      | -0.3177 | -0.6355

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | -0.5679 | -1.1358

Frag | 2 | Methyl [-CH3]                           | -0.0796 | -0.1591

Frag | 34 | -CH2- [linear]                          | 0.0260 | 0.8837

Const| * | Equation Constant                        |        | 0.8361

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

RESULT  |  Biowin7 (Anaerobic Linear Biodeg Prob)  |        | -0.2106

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

 

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.

 

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

2006

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))

GLP compliance:

yes (incl. QA statement)

Oxygen conditions:

aerobic

Inoculum or test system:

other: The micro-organisms were taken from different sources.

Details on inoculum:

Inoculum from specially grown non adapted micro-organisms.

Duration of test (contact time):

28 d

Initial conc.:

40 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

O2 consumption

Reference substance:

benzoic acid, sodium salt

Parameter:

% degradation (O2 consumption)

Value:

4

Sampling time:

28 d

Validity criteria fulfilled:

yes

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test item must be regarded as not readily biodegradable in the 10-d-window and after 28 days.

Executive summary:

The ready biodegradation in the Modified MITI Test was determined with a non adapted inoculum for the test item over a period of 28 days. The study was conducted according to OECD guideline 301 C. The test item concentration selected as appropriate was 40 mg/L, corresponding to a ThOD of 108 mgO2/L in the test vessel. The oxygen was depleted by the respiration of bacteria and the degradation was followed by measuring the oxygen concentration. The biodegradation is therefore expressed as the percentage BOD and was calculated for each study day.

 

The oxygen depletion in the inoculum control came to 0.0 mgO2/L after 28 days.

 

In order to check the activity of the test system sodium benzoate was used as functional control. The functional control reached the pass level of a biodegradation > 40 % after 1 day and > 65 % biodegradation was reached after 3 days. After 17 days the degradation came to a maximum of 94 %.

The test item did not reach the 10 % level (beginning of biodegradation) until day 28. The biodegradation remained at a level of 0 – 4 %. The mean biodegradation came to 2 % after 28 days.

 

The test item must be regarded as not readily biodegradable in the 10-d-window and after 28 days.

Reference 3

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

12 February 1991- 22 April 1991

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: GLP Guideline study with acceptable restrictions

Qualifier:

equivalent or similar to guideline

Guideline:

OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test)

GLP compliance:

yes

Oxygen conditions:

aerobic

Inoculum or test system:

activated sludge, non-adapted

Details on inoculum:

- Source of activated sludge: Municipal sewage treatment plant, Schijndel, The Netherlands
- Preparation of inoculum: activated sludge aerated for 4 h and then left to settle at least for 1/2 h. The supernatant was decanted to provide a sufficiently large volume for a 1% inoculum for each test flask

Duration of test (contact time):

28 d

Initial conc.:

10 mg/L

Based on:

test mat.

Initial conc.:

20 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

CO2 evolution

Details on study design:

TEST CONDITIONS
- Composition of medium: according to guideline
- Test temperature: 20 +/- 2°C
- pH: pH blank, 6.2; pH positive control, 5.8; pH test substance 10mg/L, 5.9; pH test substance 20mg/L, 6.0

TEST SYSTEM
- Culturing apparatus: 3L bottles all-glass brown filled with 3L test medium
- Number of culture flasks/concentration: 1
- Method used to create aerobic conditions: aeration with CO2 free air at a constant rate of 50-100 mL air/min
- Details of trap for CO2: after the aeration period, three CO2-absorber bottles were filled with 80 ml 0.025 N Ba(OH)2 and connected in series to the exit air line of each test bottle.



SAMPLING
- Sampling frequency: 2,5,7,9,12,16,21,28 d
- Sampling method: CO2 was determined by titration of remaining Ba(OH)2 with 0.05 N standardized HCL, after barium carbonate precipitation (from
the reaction between CO2 and barium hydroxide). Periodically the C02—absorber nearest to the test bottle was removed for titration. The remaining
two absorbers were each moved one position in the direction of the test bottle, and a new absorber filled with 80 ml of 0025 N Ba(OH)2 (normalized
the same day) was placed at the far end of the series. All samples were stored at —20°C for three months after delivery of this report.



CONTROL AND BLANK SYSTEM
- Inoculum blank: 1
- Reference compound: 1

Reference substance:

acetic acid, sodium salt

Parameter:

% degradation (CO2 evolution)

Value:

2.1

Sampling time:

12 d

Remarks on result:

other: 10 mg/L test substance

Parameter:

% degradation (CO2 evolution)

Value:

15

Sampling time:

28 d

Remarks on result:

other: 10 mg/L test substance

Parameter:

% degradation (CO2 evolution)

Value:

0.7

Sampling time:

12 d

Remarks on result:

other: 20 mg/L test substance

Parameter:

% degradation (CO2 evolution)

Value:

5.5

Sampling time:

28 d

Remarks on result:

other: 20 mg/L test substance

Details on results:

The test substance is not readily biodegradable under the tested conditions. The test substance was not degraded over 60% on a 10-day window
(days 2-12) for any of the tested concentrations (10 and 20 mg/L)

Results with reference substance:

103.5% sodium acetate was biodegraded by day 28. Degradation of >60% of reference substance was reached within 14 days

Interpretation of results:

other: not readily biodegradable as < 16% degradation under test conditions

Reference 4

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

supporting study

Study period:

24 Oct - 23 Dec 1975

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: basic data given

Qualifier:

equivalent or similar to guideline

Guideline:

OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))

Deviations:

yes

Remarks:

test duration was 2 weeks

GLP compliance:

not specified

Oxygen conditions:

aerobic

Inoculum or test system:

mixture of sewage, soil and natural water

Details on inoculum:

- Concentration of sludge: 30 ppm

Duration of test (contact time):

14 d

Initial conc.:

100 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

O2 consumption

Details on study design:

TEST SYSTEM
- Measuring equipment: Coulometer

CONTROL AND BLANK SYSTEM
- Inoculum blank: Yes

STATISTICAL METHODS: not stated

Parameter:

% degradation (O2 consumption)

Value:

1.1

Sampling time:

14 d

Details on results:

not biodegradable

Table 1. Result of biodegradability

	Degradability
Result by O2 consumption	1.1%
Result by HPLC	(-) %

Reference 5

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

key study

Justification for type of information:

Refer to chapter 13

Reason / purpose for cross-reference:

read-across source

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (CO2 evolution)

Value:

15

Sampling time:

28 d

Executive summary:

The ready biodegradation in the Modified MITI Test was determined with a non adapted inoculum for the test item over a period of 28 days. The study was conducted according to OECD guideline 301 C. The test item concentration selected as appropriate was 40 mg/L, corresponding to a ThOD of 108 mgO2/L in the test vessel. The oxygen was depleted by the respiration of bacteria and the degradation was followed by measuring the oxygen concentration. The biodegradation is therefore expressed as the percentage BOD and was calculated for each study day.

 

The oxygen depletion in the inoculum control came to 0.0 mgO2/L after 28 days.

 

In order to check the activity of the test system sodium benzoate was used as functional control. The functional control reached the pass level of a biodegradation > 40 % after 1 day and > 65 % biodegradation was reached after 3 days. After 17 days the degradation came to a maximum of 94 %.

The test item did not reach the 10 % level (beginning of biodegradation) until day 28. The biodegradation remained at a level of 0 – 4 %. The mean biodegradation came to 2 % after 28 days.

 

The test item must be regarded as not readily biodegradable in the 10-d-window and after 28 days.

 

Two additional studies investigating the ready biodegradability of the read Across Source substance Amides, C16-C18 (even), N,N'-ethylenebis were available. The report from Coenen (1991) was chosen as key study. This test was performed following the OECD Guideline No. 301B: Ready Biodegradability: Modified Sturm Test (1981), under GLP conditions. Activated sludge was used as inoculum and test material concentrations were 10 and 20 mg/L. On day 28 (end of the test) biodegradation values reached 15% and 5.5% at 10 and 20 mg/L test concentrations respectively. An additional supporting study was obtained from the Japanese Ministry of International Trade and Industry (MITI, 1976). This ready biodegradability test was carried out according to the OECD Guideline TG 301C: MITI (I), using activated sludge as inoculum at a concentration of 30 ppm. The test concentration used in the study was 100 ppm. After 14 days (end of the study), the test substance reached a biodegradation value of 1.1%. Thus, these results support those from the key study and Amides, C16-C18 (even), N,N'-ethylenebis can be considered as not readily biodegradable but the substance is hardly soluble in water and the very low solubility of the test substance may reduce the availability of the substance in the test medium.

Therefore, an additional calculation was used to investigate the biodegradation of  Amides, C16-C18 (even), N,N'-ethylenebis. A QSAR prediction using the following models Biowin1, Biowin2, Biowin3, Biowin4, Biowin5, Biowin6 and Biowin7 shows that the substance is not persistent in the environment and the biodegradation takes place in a time frame of weeks.

Description of key information

The ready biodegradation in the Modified MITI Test was determined with a non adapted inoculum for the test item over a period of 28 days. The study was conducted according to OECD guideline 301 C. The test item concentration selected as appropriate was 40 mg/L, corresponding to a ThOD of 108 mgO2/L in the test vessel. The oxygen was depleted by the respiration of bacteria and the degradation was followed by measuring the oxygen concentration. The biodegradation is therefore expressed as the percentage BOD and was calculated for each study day.

 

The oxygen depletion in the inoculum control came to 0.0 mgO2/L after 28 days.

 

In order to check the activity of the test system sodium benzoate was used as functional control. The functional control reached the pass level of a biodegradation > 40 % after 1 day and > 65 % biodegradation was reached after 3 days. After 17 days the degradation came to a maximum of 94 %.

The test item did not reach the 10 % level (beginning of biodegradation) until day 28. The biodegradation remained at a level of 0 – 4 %. The mean biodegradation came to 2 % after 28 days.

 

The test item must be regarded as not readily biodegradable in the 10-d-window and after 28 days.

 

Two additional studies investigating the ready biodegradability of the read Across Source substance Amides, C16-C18 (even), N,N'-ethylenebis were available. The report from Coenen (1991) was chosen as key study. This test was performed following the OECD Guideline No. 301B: Ready Biodegradability: Modified Sturm Test (1981), under GLP conditions. Activated sludge was used as inoculum and test material concentrations were 10 and 20 mg/L. On day 28 (end of the test) biodegradation values reached 15% and 5.5% at 10 and 20 mg/L test concentrations respectively. An additional supporting study was obtained from the Japanese Ministry of International Trade and Industry (MITI, 1976). This ready biodegradability test was carried out according to the OECD Guideline TG 301C: MITI (I), using activated sludge as inoculum at a concentration of 30 ppm. The test concentration used in the study was 100 ppm. After 14 days (end of the study), the test substance reached a biodegradation value of 1.1%. Thus, these results support those from the key study and Amides, C16-C18 (even), N,N'-ethylenebis can be considered as not readily biodegradable but the substance is hardly soluble in water and the very low solubility of the test substance may reduce the availability of the substance in the test medium.

Therefore, an additional calculation was used to investigate the biodegradation of  Amides, C16-C18 (even), N,N'-ethylenebis. A QSAR prediction using the following models Biowin1, Biowin2, Biowin3, Biowin4, Biowin5, Biowin6 and Biowin7 shows that the substance is not persistent in the environment and the biodegradation takes place in a time frame of weeks.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed