Reaction mass of: N,N'-[1,3-Phenylenebis(methylene)bis[12-hydroxyoctadecanamide], N,N'-hexane-1,6-diylbis(12-hydroxyoctadecanamide) and N,N'-ethane-1,2-diylbis(12-hydroxyoctadecan-1-amide)

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

EU Method C.4-C (Determination of the "Ready" Biodegradability - Carbon Dioxide Evolution Test)

Version / remarks:

92/69/EEC, C4-C (OECD Guideline No. 301B)

GLP compliance:

yes

Oxygen conditions:

aerobic

Inoculum or test system:

not specified

Reference substance:

benzoic acid, sodium salt

Parameter:

% degradation (CO2 evolution)

Value:

9

Sampling time:

28 d

Details on results:

Points of degradation plot (test substance):
4.5 % degradation after 1 d
6.5 % degradation after 2 d
7.5 % degradation after 3 d
7.5 % degradation after 5 d
7.5 % degradation after 7 d
8 % degradation after 9 d
8 % degradation after 11 d
8 % degradation after 14 d
8 % degradation after 16 d
9 % degradation after 21 d
9 % degradation after 28 d
9 % degradation after 29 d

Results with reference substance:

Points of degradation plot (reference substance):
7 % degradation after 1 d
26 % degradation after 2 d
40 % degradation after 3 d
55 % degradation after 5 d
64 % degradation after 7 d
70 % degradation after 9 d
72 % degradation after 11 d
75 % degradation after 14 d
76 % degradation after 16 d
78 % degradation after 21 d
79 % degradation after 28 d
80 % degradation after 29 d

Validity criteria fulfilled:

yes

Interpretation of results:

not readily biodegradable

Conclusions:

According to the study results, 12-hydroxyoctadecanoic acid, reaction products with 1,3-benzenedimethanamine and hexamethylenediamine is not readily biodegradable.

Executive summary:

The biodegradability of 12-hydroxyoctadecanoic acid, reaction products with 1,3-benzenedimethanamine and hexamethylenediamine is assessed in a guideline study according to EU Method C.4-C (Carbon Dioxide Evolution Test). The substance was observed to be not readily biodegradable, showing 9 % degradation by CO2 evolution after 28 days.

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

08. Jan. 2019 - 19. Mar. 2019

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

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

Deviations:

yes

Remarks:

Temperature range was 19.7 – 20.9 °C instead of 20.0 – 24.0 °C. As degradation of the positive control was in the normal range this is considered as uncritical concerning the outcome of the study.

GLP compliance:

yes (incl. QA statement)

Oxygen conditions:

aerobic

Inoculum or test system:

sewage, predominantly domestic, adapted

Details on inoculum:

Activated sludge from a biologic sewage treatment plant was used as inoculum. The chosen plant treats mostly domestic sewage. The sludge was taken from the activation basin of the ESN (Stadtentsorgung Neustadt) sewage treatment plant, Im Altenschemel, 67435 NW-Lachen-Speyerdorf. Date of collection: 11. Jan. 2019, batch no: 20190111. The sludge was filtrated, washed with test medium (2x) and re-suspended in test medium. It was then aerated until use. The dry matter was determined to contain 4800 mg of suspended solids/L.

Duration of test (contact time):

28 d

Initial conc.:

27.4 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

CO2 evolution

Reference substance:

aniline

Key result

Parameter:

% degradation (CO2 evolution)

Value:

7

Sampling time:

28 d

Details on results:

The degree of biodegradation reached 7 % after 28 days. The 10-day-window was not detected. Degradation missed 60 % within 28 days, too. The abiotic degradation reached 2.5 %.

Results with reference substance:

The degradation percentage of the reference compound at Day 7 was > 60%.

Validity criteria fulfilled:

yes

Interpretation of results:

not readily biodegradable

Conclusions:

The result of the test can be considered valid.

Executive summary:

The test item Bisamid was tested using a concentration of nominally 20 mg organic carbon/L Bisamid in test medium following OECD 301B and EU-Method C.4-C. Aniline was chosen as positive control. Activated sludge was used as inoculum (concentration in the test 25.0 mg dry matter/L). The test was left running for 28 days. All validity criteria were met. Degradation of the positive control surpassed the pass level of 60 % after 7 days. The following data were determined for the test item Bisamid:

10-day-window: not detected

degradation at the end of 10-day-window: none

degradation at the end of the test: 7 %

pass level following guideline: 60 % at the end of 10-day-window for pure substances, respective 60 % at the end of the test for mixtures

Therefore, when applying the 10-day-window, the test item Bisamid is not readily biodegradable following OECD 301B and EU C.4-C respectively. As degradation missed 60% in the course of the test, Bisamid is considered as not ultimately biodegradable, within 28 days, as well.

Reference 3

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

documentation insufficient for assessment

Qualifier:

no guideline available

Principles of method if other than guideline:

The test guideline is not specified.

GLP compliance:

not specified

Oxygen conditions:

not specified

Inoculum or test system:

not specified

Reference substance:

acetic acid, sodium salt

Parameter:

not specified

Value:

0

Sampling time:

2 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

1.8

Sampling time:

5 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

1.9

Sampling time:

7 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

1.9

Sampling time:

9 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

2.4

Sampling time:

14 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

2.4

Sampling time:

19 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

3

Sampling time:

23 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

3.2

Sampling time:

27 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

5

Sampling time:

28 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

5

Sampling time:

29 d

Remarks on result:

other: test substance

Parameter:

not specified

Value:

17

Sampling time:

2 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

49.2

Sampling time:

5 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

64.2

Sampling time:

7 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

70.2

Sampling time:

9 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

73.8

Sampling time:

14 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

79.3

Sampling time:

19 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

82.2

Sampling time:

23 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

86.9

Sampling time:

27 d

Remarks on result:

other: reference substance

Parameter:

not specified

Value:

87.3

Sampling time:

29 d

Remarks on result:

other: reference substance

Interpretation of results:

not readily biodegradable

Conclusions:

According to the study results, 1,3-bis[12-hydroxy-octadecamide-N-methylene]-benzene is not readily biodegradable.

Executive summary:

The biodegradability of 1,3-bis[12-hydroxy-octadecamide-N-methylene]-benzene is assessed in this study. The test guideline is not specified. The substance was observed to be not readily biodegradable.

Reference 4

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

The biodegradability is estimated by calculation from molecular fragments using the models BioWin3 and BioWin5 (BIOWIN v4.10), using EPI Suite.

Principles of method if other than guideline:

The biodegradability is estimated by calculation from molecular fragments using the models BioWin3 and BioWin5 (BIOWIN v4.10), using EPI Suite.

GLP compliance:

no

Specific details on test material used for the study:

Calculation is based on the structure of the test material.
- Name of test material (as cited in study report): Octadecanamide, N,N -1,2-ethanediylbis[12-hydroxy-

Parameter:

not specified

Remarks on result:

not measured/tested

Details on results:

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months
Biowin5 (MITI Linear Model Prediction) : Biodegrades Fast
Ready Biodegradability Prediction: NO

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

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months

Biowin5 (MITI Linear Model Prediction)   : Biodegrades Fast

Ready Biodegradability Prediction: NO

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

TYPE | NUM |      Biowin3 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Linear C4 terminal chain [CCC-CH3]      | 0.2983 | 0.5967

Frag | 2 | Aliphatic alcohol [-OH]                 | 0.1600 | 0.3199

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

MolWt| * | Molecular Weight Parameter               |        | -1.3813

Const| * | Equation Constant                        |        | 3.1992

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

RESULT  | Biowin3 (Survey Model - Ultimate Biodeg) |        | 2.6261

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

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

TYPE | NUM |      Biowin5 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Aliphatic alcohol [-OH]                 | 0.1611 | 0.3223

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | 0.1266 | 0.2533

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

Frag | 32 | -CH2- [linear]                          | 0.0494 | 1.5813

Frag | 2 | -CH-  [linear]                          | -0.0507 | -0.1013

MolWt| * | Molecular Weight Parameter               |        | -1.8595

Const| * | Equation Constant                        |        | 0.7121

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

RESULT  | Biowin5 (MITI Linear Biodeg Probability) |        | 0.9090

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

Validity criteria fulfilled:

not applicable

Interpretation of results:

not readily biodegradable

Conclusions:

The given biodegradability is calculated from BIOWIN using the models BioWin3 and BioWin5. The criteria for readily biodegradable are BioWin3: weeks or faster and BioWin5: probability is >= 0.5. For 12-hydroxy-N-[2-(12-hydroxyoctadecanoylamino)ethyl]octadecanamide, the result of BioWin3 is weeks-months while the result of BioWin5 is >= 0.5. Therefore, the substance should be classified as not readily biodegradable.

Executive summary:

The given biodegradability is calculated from BIOWIN using the models BioWin3 and BioWin5. The criteria for readily biodegradable are BioWin3: weeks or faster and BioWin5: probability is >= 0.5. For 12-hydroxy-N-[2-(12-hydroxyoctadecanoylamino)ethyl]octadecanamide, the result of BioWin3 is weeks-months while the result of BioWin5 is >= 0.5. Therefore, the substance should be classified as not readily biodegradable. Nevertheless, the estimation by calculation only provides an approximation and cannot replace empirical studies. The EPA recommends that EPI Suite is a screening-level tool and should not be used if acceptable measured values are available.

Reference 5

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

The biodegradability is estimated by calculation from molecular fragments using the models BioWin3 and BioWin5 (BIOWIN v4.10), using EPI Suite.

Principles of method if other than guideline:

The biodegradability is estimated by calculation from molecular fragments using the models BioWin3 and BioWin5 (BIOWIN v4.10), using EPI Suite.

GLP compliance:

no

Specific details on test material used for the study:

Calculation is based on the structure of the test material.
- Name of test material (as cited in study report): Octadecanamide, N,N'-1,6-hexanediylbis 12-hydroxy-

Parameter:

not specified

Remarks on result:

not measured/tested

Details on results:

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months
Biowin5 (MITI Linear Model Prediction) : Biodegrades Fast
Ready Biodegradability Prediction: NO

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

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months

Biowin5 (MITI Linear Model Prediction)   : Biodegrades Fast

Ready Biodegradability Prediction: NO

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

TYPE | NUM |      Biowin3 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Linear C4 terminal chain [CCC-CH3]      | 0.2983 | 0.5967

Frag | 2 | Aliphatic alcohol [-OH]                 | 0.1600 | 0.3199

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

MolWt| * | Molecular Weight Parameter               |        | -1.5053

Const| * | Equation Constant                        |        | 3.1992

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

RESULT  | Biowin3 (Survey Model - Ultimate Biodeg) |        | 2.5021

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

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

TYPE | NUM |      Biowin5 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Aliphatic alcohol [-OH]                 | 0.1611 | 0.3223

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | 0.1266 | 0.2533

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

Frag | 36 | -CH2- [linear]                          | 0.0494 | 1.7790

Frag | 2 | -CH-  [linear]                          | -0.0507 | -0.1013

MolWt| * | Molecular Weight Parameter               |        | -2.0264

Const| * | Equation Constant                        |        | 0.7121

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

RESULT  | Biowin5 (MITI Linear Biodeg Probability) |        | 0.9397

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

Validity criteria fulfilled:

not applicable

Interpretation of results:

not readily biodegradable

Conclusions:

The given biodegradability is calculated from BIOWIN using the models BioWin3 and BioWin5. The criteria for readily biodegradable are BioWin3: weeks or faster and BioWin5: probability is >= 0.5. For Octadecanamide, N,N'-1,6-hexanediylbis 12-hydroxy-, the result of BioWin3 is weeks-months while the result of BioWin5 is >= 0.5. Therefore, the substance should be classified as not readily biodegradable.

Executive summary:

The given biodegradability is calculated from BIOWIN using the models BioWin3 and BioWin5. The criteria for readily biodegradable are BioWin3: weeks or faster and BioWin5: probability is >= 0.5. For Octadecanamide, N,N'-1,6-hexanediylbis 12-hydroxy-, the result of BioWin3 is weeks-months while the result of BioWin5 is >= 0.5. Therefore, the substance should be classified as not readily biodegradable. Nevertheless, the estimation by calculation only provides an approximation and cannot replace empirical studies. The EPA recommends that EPI Suite is a screening-level tool and should not be used if acceptable measured values are available.

Reference 6

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

The biodegradability is estimated by calculation from molecular fragments using the models BioWin3 and BioWin5 (BIOWIN v4.10), using EPI Suite.

Principles of method if other than guideline:

The biodegradability is estimated by calculation from molecular fragments using the models BioWin3 and BioWin5 (BIOWIN v4.10), using EPI Suite.

GLP compliance:

no

Specific details on test material used for the study:

Calculation is based on the structure of the test material.
- Name of test material (as cited in study report): N,N'-(Benzene-1,3-diyldimethanediyl)bis(12-hydroxyoctadecanamide)

Parameter:

not specified

Remarks on result:

not measured/tested

Details on results:

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months
Biowin5 (MITI Linear Model Prediction) : Biodegrades Fast
Ready Biodegradability Prediction: NO

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

Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months

Biowin5 (MITI Linear Model Prediction)   : Biodegrades Fast

Ready Biodegradability Prediction: NO

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

TYPE | NUM |      Biowin3 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Linear C4 terminal chain [CCC-CH3]      | 0.2983 | 0.5967

Frag | 2 | Aliphatic alcohol [-OH]                 | 0.1600 | 0.3199

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

MolWt| * | Molecular Weight Parameter               |        | -1.5494

Const| * | Equation Constant                        |        | 3.1992

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

RESULT  | Biowin3 (Survey Model - Ultimate Biodeg) |        | 2.4579

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

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

TYPE | NUM |      Biowin5 FRAGMENT DESCRIPTION        | COEFF | VALUE

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

Frag | 2 | Aliphatic alcohol [-OH]                 | 0.1611 | 0.3223

Frag | 2 | Amide  [-C(=O)-N or -C(=S)-N]          | 0.1266 | 0.2533

Frag | 2 | Aromatic-CH2                             | -0.0557 | -0.1114

Frag | 4 | Aromatic-H                               | 0.0082 | 0.0329

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

Frag | 30 | -CH2- [linear]                          | 0.0494 | 1.4825

Frag | 2 | -CH-  [linear]                          | -0.0507 | -0.1013

MolWt| * | Molecular Weight Parameter               |        | -2.0859

Const| * | Equation Constant                        |        | 0.7121

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

RESULT  | Biowin5 (MITI Linear Biodeg Probability) |        | 0.5052

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

Validity criteria fulfilled:

not applicable

Interpretation of results:

not readily biodegradable

Conclusions:

The given biodegradability is calculated from BIOWIN using the models BioWin3 and BioWin5. The criteria for readily biodegradable are BioWin3: weeks or faster and BioWin5: probability is >= 0.5. For N,N'-[1,3-Phenylenebis(methylene)bis[12-hydroxyoctadecanamide], the result of BioWin3 is weeks-months while the result of BioWin5 is >= 0.5. Therefore, the substance should be classified as not readily biodegradable.

Executive summary:

The given biodegradability is calculated from BIOWIN using the models BioWin3 and BioWin5. The criteria for readily biodegradable are BioWin3: weeks or faster and BioWin5: probability is >= 0.5. For N,N'-[1,3-Phenylenebis(methylene)bis[12-hydroxyoctadecanamide], the result of BioWin3 is weeks-months while the result of BioWin5 is >= 0.5. Therefore, the substance should be classified as not readily biodegradable. Nevertheless, the estimation by calculation only provides an approximation and cannot replace empirical studies. The EPA recommends that EPI Suite is a screening-level tool and should not be used if acceptable measured values are available.

Description of key information

The substance consists of multiple different constituents with similar chemical structure: N,N'-ethane-1,2-diylbis(12-hydroxyoctadecanamide), N,N'-hexane-1,6-diylbis(12-hydroxyoctadecanamide) and N,N'-[1,3-phenylenebis(methylene)]bis(12-hydroxyoctadecanamide). There are no experimental data on the multi-constituent substance available. The individual constituents and mixtures of similar structured bisamides are considered suitable read-across substances.

In three experimental studies on the read-across substances 1,3-bis[12-hydroxy-octadecamide-N-methylene]-benzene, 12-hydroxyoctadecanoic acid, reaction products with 1,3-benzenedimethanamine and hexamethylenediamine and N,N'-ethane-1,2-diylbis(12-hydroxyoctadecan-1-amide) degradation of less than 10 % after 28 days was observed. Therefore, the read-across substances were considered ‘not readily biodegradable’.

Predictions of the biodegradability of three individual constituents of the substance by the QSAR software tool EPI Suite v4.1.1 (used models: BioWin3 and BioWin5) also resulted in ‘not readily biodegradable’ in all three cases.

Based on the results on biodegradation of the read-across substances and the QSAR predictions on the biodegradability of individual constituents, the substance is expected to be not readily biodegradable. Testing of the substance is not considered necessary.

Additional information

The calculation on the biodegradability of individual constituents by ChemProp predicted aerobic and anaerobic biodegradation. The half-life estimated from reference molecules is 170 h in all three cases. However, the constituents were outside of the applicability domain of the used models. Therefore, these results are disregarded for assessment.