4,4'-methylenebis(cyclohexylamine)

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Reference 1

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:

GLP guideline study (OECD 301C) of the structural analogue DM-PACM (CAS 6864-37-5). PACM and DM-PACM are considered read-across analogues based on structural similarity and similar physico-chemical and toxicological properties. The common structural features of the two substances are: a common functional primary amine group; the amines are bound to a cyclic aliphatic organic substituent; there are no elements other than carbon, hydrogen and nitrogen; identical structures except for a methyl group on each cyclohexane, ortho to the amine on DM-PACM similar molecular weights, both under 500 daltons, qualifying as “low molecular weight” compounds. For a detailed read across justification see also the attached justification document.

Reason / purpose for cross-reference:

read-across source

Parameter:

% degradation (O2 consumption)

Value:

0

Sampling time:

28 d

Parameter:

% degradation (TOC removal)

Value:

3

Sampling time:

28 d

Parameter:

% degradation (test mat. analysis)

Remarks:

by HPLC

Value:

0

Sampling time:

28 d

Results with reference substance:

The degradation of the reference substance anline was 76% and 83% (based on BOD) after 7 and 14 days, respectively. Therefore, the test conditions in this test were confirmed to be valid.

Measured biochemical oxygen demand (BOD)

Vessel no.	Sample	BOD (mg)
		day 7	day 14	day 21	day 28
1	sludge + aniline (reference)	70.4	79.3	80.4	85.0
2	water + test substance	0	0	0	0
3	sludge + test substance	1.4	3.2	3.8	4.6
4	sludge + test substance	1.3	3.2	3.9	4.6
5	sludge + test substance	1.8	4.0	5.0	5.9
6	blank control	1.9	4.4	6.3	10.4

 

 

BOD, DOC and HPLC measurement after 28 d

Sample		water + test substance	sludge + test substance
Vessel no.		2	3	4	5
BOD^1	mg	0	0	0	0
DOC^2	mg	22.8	22.8	22.3	22.2
	%	100	100	98	94
HPLC^3	mg	28.6	28.5	29.4	28.4
	%	95	95	98	95

¹: biochemical oxygen demand

²: dissolved organic carbon

³: remaining amount of test substance (measured by HPLC method)

pH values and visual control

Date of measurement	Sample	pH	appearance
Day 0	water + test substance	10.6	test substance entirely dissolved
	sludge + test substance	Vessel 3: 8.9 Vessel 4: 8.8 Vessel 5: 8.8	test substance entirely dissolved
Day 28	water + test substance	10.4	test substance largely undissolved
	sludge + test substance	Vessel 3: 7.4 Vessel 4: 7.3 Vessel 5: 7.4	sludge partly undissolved

Validity criteria fulfilled:

yes

Interpretation of results:

other: under test conditions no biodegradation observed.

Reference 2

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

(Q)SAR

Adequacy of study:

key study

Study period:

2021

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification

Justification for type of information:

1. SOFTWARE
OASIS Catalogic v5.14.1.5

2. MODEL (incl. version number)
CATALOGIC 301C v11.16

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
See section 'Test Material'.

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
See attached QMRF.

5. APPLICABILITY DOMAIN
See attached QPRF.

6. ADEQUACY OF THE RESULT
- The model is scientifically valid (see attached QMRF).
- The model estimates the biodegradability of a substance Screening information on the ready biodegradability is required for substances manufactured or imported in quantities of 1 t/y or more. Depending on the results, further information may be required for substances manufactured or imported in quantities of 100 t/y or more (simulation testing on ultimate degradation in surface water/soil/sediment). Column 2 of REACH Annex VII provides exemptions for conducting the study. It does not need to be conducted if the substance is inorganic. According to column 2 of REACH Annex IX, testing is not required if the substance is highly insoluble in water, or the substance is readily biodegradable.
- See attached QPRF for reliability assessment.

Principles of method if other than guideline:

Estimation of ready biodegradation in water using CATALOGIC v5.14.1.5 BOD 28 days MITI (OECD 301C) v11.16

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

other: model calculation

Duration of test (contact time):

28 d

Key result

Parameter:

% degradation (O2 consumption)

Value:

42

Sampling time:

28 d

Concomitant predictions :

Not ready degradable

Primary Half Life = 9.72 days

Ultimate Half Life = 1m 5d

Predicted value (model result): O2 -consumption (BOD) = 0.42 ± 0.0317

Predicted metabolites:

Table: QSAR prediction for CAS 1761 -71 -3 using CATALOGIC 301C v11.16 (OASIS CATALOGIC v5.14.1.5; metabolites with a quantity > 0.001 mol/mol parent after 28 d are highlighted by grey background and bold type; metabolite no: according to (Q)SAR model Catalogic v11.16)

#	Metabolite (no)	Smiles	Quantity (mol/mol parent)	LogKow	BOD prediction (% after 28 d)
1	11	NC1CCC(CC(O)(CC(O)=O)C(O)=O)CC1	0,2413	-3	53
2	23	C=C	0,1722	1	10
3	14	NC1CCC(O)(CC(O)=O)CC1	0,1639	-3	55
4	parent	NC1CCC(CC2CCC(N)CC2)CC1	0,1358	2	42
5	15	NC1CCC(=O)CC1	0,1302	-0,419	38
6	3	NC1CCC(CC2CCC(=O)OCC2)CC1	0,09323	2	61
7	17	O=C1CCC(=O)CCO1	0,02389	0,434	53
8	19	OC(=O)CCC(O)=O	0,01969	-0,754	90
9	42	NC1CCC(CCC(O)=O)CC1	0,002273	-1	67
10	56	NC1CCC(CC(CCC(N)CO)C(O)=O)CC1	0,001727	-3	60
11	68	NC1CCC(CC=O)CC1	0,001571	1	60
12	54	NC1CCC(CC(=O)CC(O)=O)COC1=O	0,001571	-5	73
13	58	NC(CCCCC1CCC(=O)CC1)CO	0,001571	0,99	74
14	59	NC1CCC(CCCCC(=O)CO)CC1	0,001571	2	76
15	16	O=C1CCC(=O)CC1	0,001552	-0,924	56
16	79	NC(CCC(O)CC(=O)CC(O)=O)CC(O)=O	0,001396	-6	82
17	32	NC1CCC(CC2CCC(N)C(=O)OC2)CC1	0,0008525	0,766	52
18	61	NC1CCC(CC(O)CCC(N)CC(O)=O)CC1	0,0007579	-3	47
19	67	NC1CCC(CC(O)C(O)=O)CC1	0,0007417	-3	51
20	53	NC1CCC(CC(O)(CC(O)=O)C(O)=O)COC1=O	0,0007417	-6	59
21	80	NC1CCC(CC2CCC(N)OC(=O)C2)CC1	0,000672	3	59
22	60	NC1CCC(CC2CCC(N)CC(=O)O2)CC1	0,000672	0,766	51
23	55	NC1CCC(CC2CCC(N)COC2=O)CC1	0,000672	0,766	53
24	78	NC(CCC(O)CC(O)(CC(O)=O)C(O)=O)CC(O)=O	0,0006594	-5	63
25	57	NC(CCCCC1CCC(N)CC1)CO	0,0005148	1	58
26	33	NC1CCC(CC2CCC(=O)C(=O)OC2)CC1	0,0002887	2	78
27	45	NC1CCC(CC2CCC(=O)OCC2)COC1=O	0,0002887	-0,1892	68
28	70	NC(CCC(O)CC1CCC(=O)OCC1)CC(O)=O	0,0002567	-3	67
29	41	NC1CCC(CC(C(O)=O)C(O)=O)CC1	3,95E-05	-3	71
30	49	NC1CCC(CC(CC(O)=O)C=CC(O)=O)COC1=O	0	-4	69
31	62	NC1CCC(CC(O)CCC(=O)CC(O)=O)CC1	0	-3	68
32	34	NC1CCC(CC(CCC(=O)C(O)=O)CO)CC1	0	0,399	78
33	38	NC1CCC(CC(C=CC(O)=O)C(O)=O)CC1	0	-2	77
34	9	NC1CCC(CC(CC(O)=O)C(=O)CC(O)=O)CC1	0	-3	62
35	66	NC1CCC(CC(O)C(=O)CC(O)=O)CC1	0	-3	60
36	2	NC1CCC(CC2CCC(=O)CC2)CC1	0	3	62
37	4	NC1CCC(CC(CCC(O)=O)CCO)CC1	0	-0,98	65
38	81	NC1CCC(CC(CCC(N)O)CC(O)=O)CC1	0	-3	65
39	82	NC1CCC(CC(CCC=O)CC(O)=O)CC1	0	-1	65
40	69	NC(CCC(O)CC1CCC(=O)CC1)CC(O)=O	0	-3	68
41	44	NC1CCC(CC2CCC(=O)CC2)COC1=O	0	0,2604	69
42	65	NC1CCC(CC(O)C(O)CC(O)=O)CC1	0	-3	60
43	64	NC1CCC(CC(O)C=CC(O)=O)CC1	0	-0,677	62
44	47	NC1CCC(CC(CCC(O)=O)CC=O)COC1=O	0	-4	70
45	48	NC1CCC(CC(CCC(O)=O)CC(O)=O)COC1=O	0	-4	69
46	37	NC1CCC(CC(CCC(O)=O)C(O)=O)CC1	0	-2	77
47	72	NC(CCC(O)CC(CCC(O)=O)CC=O)CC(O)=O	0	-4	73
48	73	NC(CCC(O)CC(CCC(O)=O)CC(O)=O)CC(O)=O	0	-4	72
49	50	NC1CCC(CC(CC(O)=O)C(O)CC(O)=O)COC1=O	0	-5	68
50	39	NC1CCC(CC(C(O)CC(O)=O)C(O)=O)CC1	0	-3	76
51	8	NC1CCC(CC(CC(O)=O)C(O)CC(O)=O)CC1	0	-3	62
52	71	NC(CCC(O)CC(CCC(O)=O)CCO)CC(O)=O	0	-4	73
53	10	NC1CCC(CC(CC(O)=O)C(O)=O)CC1	0	-2	55
54	63	NC1CCC(CC(O)CCC(O)=O)CC1	0	-2	62
55	28	OC(=O)C=O	0	-1	100
56	52	NC1CCC(CC(CC(O)=O)C(O)=O)COC1=O	0	-5	61
57	40	NC1CCC(CC(C(=O)CC(O)=O)C(O)=O)CC1	0	-4	76
58	26	OCC=O	0	-2	100
59	27	OCC(O)=O	0	-1	100
60	18	C=CC(=O)CCC(O)=O	0	0,1537	60
61	24	C1CO1	0	-0,0454	100
62	12	NC1CCC(CC(=O)CC(O)=O)CC1	0	-3	66
63	75	NC(CCC(O)CC(CC(O)=O)C(O)CC(O)=O)CC(O)=O	0	-5	71
64	51	NC1CCC(CC(CC(O)=O)C(=O)CC(O)=O)COC1=O	0	-6	68
65	74	NC(CCC(O)CC(CC(O)=O)C=CC(O)=O)CC(O)=O	0	-4	72
66	29	OC(=O)C(O)=O	0	-2	100
67	6	NC1CCC(CC(CCC(O)=O)CC(O)=O)CC1	0	-1	64
68	31	CC(O)=O	0	0,0868	100
69	35	NC1CCC(CC(CCC(=O)C(O)=O)C=O)CC1	0	0,3744	78
70	46	NC1CCC(CC(CCC(O)=O)CCO)COC1=O	0	-3	70
71	36	NC1CCC(CC(CCC(=O)C(O)=O)C(O)=O)CC1	0	-3	78
72	7	NC1CCC(CC(CC(O)=O)C=CC(O)=O)CC1	0	-2	64
73	76	NC(CCC(O)CC(CC(O)=O)C(=O)CC(O)=O)CC(O)=O	0	-6	71
74	13	NC1CCC(CC(O)=O)CC1	0	-2	58
75	25	OCCO	0	-1	100
76	5	NC1CCC(CC(CCC(O)=O)CC=O)CC1	0	-1	65
77	20	CCC(O)=O	0	0,578	100
78	77	NC(CCC(O)CC(CC(O)=O)C(O)=O)CC(O)=O	0	-5	64

Metabolites with a quantity < 0.001 mol/mol parent after 28 d are not considered being relevant for the PBT/vPvB assessment and, therefore their PBT/vPvB status and BCF value were not assessed.

 

Conclusion:

Overall predicted metabolites: 77 metabolits

15 metabolites: quantity > 0.001; thereof: 9 RBD and 15 log Kow <3.

Metabolite No. 23 (BOD 10%) is identified as ethylene (CAS 74 -85-1). The results of the BioHCwin for ethylene indicate a half-life of 2.91 days and is therefore also considered as not P/vP.

All relevant predicted metabolites are neither PBT nor vP/vB

T: not assessed as no critical combination nRBD (~P/vP) plus log Kow >3 (~B/vB)

Interpretation of results:

not readily biodegradable

Remarks:

according to OECD criteria

Reference 3

Endpoint:

biodegradation in water: inherent biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

May 1986

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Comparable to guideline study with acceptable restrictions

Qualifier:

according to guideline

Guideline:

OECD Guideline 302 B (Inherent biodegradability: Zahn-Wellens/EMPA Test)

Qualifier:

according to guideline

Guideline:

other: ISO 8192B

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

activated sludge, industrial, non-adapted

Details on inoculum:

- Source of inoculum/activated sludge: Activated sludge, non adapted, from the industrial wastewater treatment plant of BASF, production site Ludwigshafen, Germany
- Concentration of sludge: 1000 mg/L dry weight

Duration of test (contact time):

28 d

Initial conc.:

400 mg/L

Based on:

TOC

Parameter followed for biodegradation estimation:

TOC removal

Details on study design:

TEST CONDITIONS
- Test temperature: room temperature (20-25°C) on a magnetic stirrer, aerated with air (sparging)
- pH: measured (6.8-7.6)

TEST SYSTEM
- Culturing apparatus: 5 L-glass bottle
- Liquid volume: 3000 ml
556 mL stock solution, 390 mL synthetic sewage, 705 mL water, 788 mL activated sludge
- inoculum: 1000 mg/L dry weight
- Number of culture flasks/concentration: 1 flask
- Test performed in open system: no


SAMPLING
- Sampling frequency: samples were taken at regular intervals and the sample volume (approx. 50 ml) was always replaced with tap water. Thus,
the starting volume remained constant during the whole test (approx. 3000 ml), but the reference value to calculate the elimination degree had to be corrected after each sampling.

CONTROL AND BLANK SYSTEM
- Inoculum blank: no blank flask was tested in parallel but a statistically obtained mean value of 17 mg/L DOC was used to calculate the elimination
- reference substance: no reference substance was tested in parallel

Parameter:

% degradation (DOC removal)

Value:

< 10

Sampling time:

28 d

Kinetic of elimination, pH:

Time (days)	Reference value	Test substance (mg/L TOC)	Test substance elimination(%)	pH
0	400	425	-6	7.5
3 h	393	406	1	7.2
1	386	359	11	7.3
3	380	405	-2	7.6
7	373	345	12	7.4
12	367	351	9	7.5
19	361	344	9	7.5
23	355	357	4	6.8
28	349	363	1	6.9

Interpretation of results:

not inherently biodegradable

Conclusions:

The test item showed no biodegradation under the present conditions of this inherent biodegradation study according to Zahn-Wellens .

Executive summary:

The test item was exposed to activated sludge from a industrial waste water treatment plant at a concentration of 1000 mg/l for 28 days. The test item attained less than 10 % degradation after 28 days and therefore cannot be considered to be inherently biodegradable.

Reference 4

Endpoint:

biodegradation in water: screening tests

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Performed according to German Industrial Standards.

Qualifier:

according to guideline

Guideline:

other: BOD5: German Industrial Standard DIN 38409, T 51 COD: German Industrial Standard DIN 38409, T 43

Principles of method if other than guideline:

BOD5: German Industrial Standard DIN 38409, T 51
COD: German Industrial Standard DIN 38409, T 43

GLP compliance:

no

Oxygen conditions:

aerobic

Inoculum or test system:

other: Effluent from wastewater treatment plant, industrial

Duration of test (contact time):

5 d

Initial conc.:

731 mg/L

Based on:

TOC

Parameter followed for biodegradation estimation:

O2 consumption

Details on study design:

Test substance solved at 40°C and cooled down to ambient temperature

Stock solution:
1014 mg/l substance
731 mg/l TOC (730 mg/g substance)
2410 mg/l COD (2374 mg/g substance)

Dillution: 200, 300, 450 mL

Parameter:

other: BOD5*100/COD

Value:

< 2

Sampling time:

5 d

Remarks on result:

other: Sampling time not reported

Details on results:

Stock solution:
1014 mg/l substance
731 mg/l TOC (730 mg/g substance)
2410 mg/l COD (2374 mg/g substance)

BOD5: < 2mg/l (<2 mg/g substance)
BOD5/COD: 0,0008

Key result

Parameter:

BOD5

Value:

< 2 mg O2/g test mat.

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

Under test conditions no biodegradation observed.

Executive summary:

The test item was examined for its 5 day biological oxygen demand BOD5 and its chemical oxygen demand COD occording to german industrial standards

DIN 38409, T 51 and DIN 38409, T 43. The test item attained less than 2 mg/g BOD and less than 1 % degradation (BOD5/COD) and therefore cannot be considered biodegradable.

Reference 5

Endpoint:

biodegradation in water: ready biodegradability

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: Accepted calculation method

Principles of method if other than guideline:

Calculation based on BIOWIN v4.00, Estimation Programs Interface Suite™ for Microsoft® Windows v 4.10. US EPA, United States Environmental Protection Agency, Washington, DC, USA.

GLP compliance:

no

Oxygen conditions:

other: not applicable

Inoculum or test system:

other: not applicable

Parameter:

not specified

Remarks:

Data not available from this type of model.

Remarks on result:

other: Data not available from this type of model.

Details on results:

For detailed description on the model and its applicability, see "Any other information on materials and methods incl. tables".

Biowin1 (Linear Model Prediction): Biodegrades Fast

Biowin2 (Non-Linear Model Prediction): Biodegrades Fast

Biowin3 (Ultimate Biodegradation Timeframe): Weeks

Biowin4 (Primary Biodegradation Timeframe): Days-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

 

BIOWIN 1:

TYPE	NUM	Biowin1 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Aliphatic amine [-NH2 or -NH-]	0.1538	0.3077
MolWt	*	Molecular Weight Parameter		-0.1001
Const	*	Equation Constant		0.7475
RESULT	Biowin1 (Linear Biodeg Probability)			0.9551

 

BIOWIN 2:

TYPE	NUM	Biowin2 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Aliphatic amine [-NH2 or -NH-]	1.1099	2.2198
MolWt	*	Molecular Weight Parameter		-2.9872
RESULT	Biowin2 (Non-Linear Biodeg Probability)			0.9039

 

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

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

 

Biowin 3:

TYPE	NUM	Biowin3 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Aliphatic amine [-NH2 or -NH-]	0.0244	0.0489
MolWt	*	Molecular Weight Parameter		-0.4649
Const	*	Equation Constant		3.1992
RESULT	Biowin3 (Survey Model - Ultimate Biodeg)			2.7832

 

BIOWIN 4:

TYPE	NUM	Biowin4 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Aliphatic amine [-NH2 or -NH-]	0.0433	0.0866
MolWt	*	Molecular Weight Parameter		-0.3035
Const	*	Equation Constant		3.8477
RESULT	Biowin4 (Survey Model - Primary Biodeg)			3.6308

 

Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks

(Primary & Ultimate) 2.00 -> months 1.00 -> longer

 

BIOWIN 5:

TYPE	NUM	Biowin5 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Aliphatic amine [-NH2 or -NH-]	0.0333	0.0666
Frag	1	-CH2- [linear]	0.0494	0.0494
Frag	8	-CH2- [cyclic]	0.0197	0.1578
Frag	4	-CH - [cyclic]	0.0124	0.0498
MolWt	*	Molecular Weight Parameter		-0.6258
Const	*	Equation Constant		0.7121
RESULT	Biowin5 (MITI Linear Biodeg Probability)			0.4099

 

BIOWIN 6:

TYPE	NUM	Biowin6 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Aliphatic amine [-NH2 or -NH-]	-0.2845	-0.5691
Frag	1	-CH2- [linear]	0.4295	0.4295
Frag	8	-CH2- [cyclic]	0.2365	1.8922
Frag	4	-CH - [cyclic]	-0.1295	-0.5178
MolWt	*	Molecular Weight Parameter		-6.0730
RESULT	Biowin6 (MITI Non-Linear Biodeg Probability)			0.0901

 

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

 

BIOWIN 7:

TYPE	NUM	Biowin7 FRAGMENT DESCRIPTION	COEFF	VALUE
Frag	2	Aliphatic amine [-NH2 or -NH-]	0.1773	0.3546
Frag	1	-CH2- [linear]	0.0260	0.0260
Frag	8	-CH2- [cyclic]	-0.1200	-0.9601
Frag	4	-CH - [cyclic]	0.0395	0.1578
Const	*	Equation Constant		0.8361
RESULT	Biowin7 (Anaerobic Linear Biodeg Prob)			0.4143

 

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 applicable

Interpretation of results:

other: not readily biodegradable

Conclusions:

The test item was predicted to be not readily biodegradable using the calculation method BIOWIN (Version 4.10)

Description of key information

The substance was calculated to be moderately biodegradable (42% not readily biodegradable).

In an OECD 302 study with industrial sludge the substance was neither readily nor inherently biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

not biodegradable

Additional information

PACM (4,4'-methylenebis(cyclohexylamine)) was shown to be poorly degraded in water. The substance is not readily biodegradable. The conclusion is based on the following data:

- CATALOGIC v5.14.1 OECD 301C v.11.16 : 42% ± 3,17%, not readily biodegradable.

- BASF AG (1986). OECD 302B (inherent biodegradability), industrial activated sludge: < 10% after 28 d, poorly eliminated from water

- NITE (2001): 0% after 28 days Read Across to DM-PACM (CAS 6864-37-5) 

- BIOWIN v4.10 (EPI Suite v4.10; 2011): overall conclusion on six modules: not readily biodegradable

- BASF AG (1986). Report no. 01/114/86 BOD5/COD determination, industrial wastewater BOD: <2mg/L (2 mg/g substance)

 

 

Metabolites:

CATALOGIC 301C v11.16 (OASIS Catalogic v5.14.1.5) predicted for the parent compound 77 metabolites, identifying 15 metabolites as relevant degradation products in terms of PBT/vPvB assessment, with an estimated quantity of ≥ 0.1% (for details see ‘Attached background material’ of the respective Endpoint Study Record).

Nine of the relevant metabolites were calculated to be readily biodegradable (≥ 60% after 28 days, based on BOD). The other relevant metabolites were estimated to be not readily biodegradable (10 to 55% after 28 days, based on BOD). In conclusion, six of the predicted metabolites present in a concentration of ≥ 0.1% (equivalent to >=0.001 mol/mol parent) are estimated to be not readily biodegradable.

 

Table: QSAR prediction for CAS 1761-71-3 using CATALOGIC 301C v11.16 (OASIS CATALOGIC v5.14.1.5; metabolites with a quantity > 0.001 mol/mol parent after 28 d are highlighted by grey background and bold type; metabolite no: according to (Q)SAR model Catalogic v11.16)

 

#	Metabolite (no)	Smiles	Quantity (mol/mol parent)	LogKow	BOD prediction (% after 28 d)
1	11	NC1CCC(CC(O)(CC(O)=O)C(O)=O)CC1	0,2413	-3	53
2	23	C=C	0,1722	1	10
3	14	NC1CCC(O)(CC(O)=O)CC1	0,1639	-3	55
4	parent	NC1CCC(CC2CCC(N)CC2)CC1	0,1358	2	42
5	15	NC1CCC(=O)CC1	0,1302	-0,419	38
6	3	NC1CCC(CC2CCC(=O)OCC2)CC1	0,09323	2	61
7	17	O=C1CCC(=O)CCO1	0,02389	0,434	53
8	19	OC(=O)CCC(O)=O	0,01969	-0,754	90
9	42	NC1CCC(CCC(O)=O)CC1	0,002273	-1	67
10	56	NC1CCC(CC(CCC(N)CO)C(O)=O)CC1	0,001727	-3	60
11	68	NC1CCC(CC=O)CC1	0,001571	1	60
12	54	NC1CCC(CC(=O)CC(O)=O)COC1=O	0,001571	-5	73
13	58	NC(CCCCC1CCC(=O)CC1)CO	0,001571	0,99	74
14	59	NC1CCC(CCCCC(=O)CO)CC1	0,001571	2	76
15	16	O=C1CCC(=O)CC1	0,001552	-0,924	56
16	79	NC(CCC(O)CC(=O)CC(O)=O)CC(O)=O	0,001396	-6	82
17	32	NC1CCC(CC2CCC(N)C(=O)OC2)CC1	0,0008525	0,766	52
18	61	NC1CCC(CC(O)CCC(N)CC(O)=O)CC1	0,0007579	-3	47
19	67	NC1CCC(CC(O)C(O)=O)CC1	0,0007417	-3	51
20	53	NC1CCC(CC(O)(CC(O)=O)C(O)=O)COC1=O	0,0007417	-6	59
21	80	NC1CCC(CC2CCC(N)OC(=O)C2)CC1	0,000672	3	59
22	60	NC1CCC(CC2CCC(N)CC(=O)O2)CC1	0,000672	0,766	51
23	55	NC1CCC(CC2CCC(N)COC2=O)CC1	0,000672	0,766	53
24	78	NC(CCC(O)CC(O)(CC(O)=O)C(O)=O)CC(O)=O	0,0006594	-5	63
25	57	NC(CCCCC1CCC(N)CC1)CO	0,0005148	1	58
26	33	NC1CCC(CC2CCC(=O)C(=O)OC2)CC1	0,0002887	2	78
27	45	NC1CCC(CC2CCC(=O)OCC2)COC1=O	0,0002887	-0,1892	68
28	70	NC(CCC(O)CC1CCC(=O)OCC1)CC(O)=O	0,0002567	-3	67
29	41	NC1CCC(CC(C(O)=O)C(O)=O)CC1	3,95E-05	-3	71
30	49	NC1CCC(CC(CC(O)=O)C=CC(O)=O)COC1=O	0	-4	69
31	62	NC1CCC(CC(O)CCC(=O)CC(O)=O)CC1	0	-3	68
32	34	NC1CCC(CC(CCC(=O)C(O)=O)CO)CC1	0	0,399	78
33	38	NC1CCC(CC(C=CC(O)=O)C(O)=O)CC1	0	-2	77
34	9	NC1CCC(CC(CC(O)=O)C(=O)CC(O)=O)CC1	0	-3	62
35	66	NC1CCC(CC(O)C(=O)CC(O)=O)CC1	0	-3	60
36	2	NC1CCC(CC2CCC(=O)CC2)CC1	0	3	62
37	4	NC1CCC(CC(CCC(O)=O)CCO)CC1	0	-0,98	65
38	81	NC1CCC(CC(CCC(N)O)CC(O)=O)CC1	0	-3	65
39	82	NC1CCC(CC(CCC=O)CC(O)=O)CC1	0	-1	65
40	69	NC(CCC(O)CC1CCC(=O)CC1)CC(O)=O	0	-3	68
41	44	NC1CCC(CC2CCC(=O)CC2)COC1=O	0	0,2604	69
42	65	NC1CCC(CC(O)C(O)CC(O)=O)CC1	0	-3	60
43	64	NC1CCC(CC(O)C=CC(O)=O)CC1	0	-0,677	62
44	47	NC1CCC(CC(CCC(O)=O)CC=O)COC1=O	0	-4	70
45	48	NC1CCC(CC(CCC(O)=O)CC(O)=O)COC1=O	0	-4	69
46	37	NC1CCC(CC(CCC(O)=O)C(O)=O)CC1	0	-2	77
47	72	NC(CCC(O)CC(CCC(O)=O)CC=O)CC(O)=O	0	-4	73
48	73	NC(CCC(O)CC(CCC(O)=O)CC(O)=O)CC(O)=O	0	-4	72
49	50	NC1CCC(CC(CC(O)=O)C(O)CC(O)=O)COC1=O	0	-5	68
50	39	NC1CCC(CC(C(O)CC(O)=O)C(O)=O)CC1	0	-3	76
51	8	NC1CCC(CC(CC(O)=O)C(O)CC(O)=O)CC1	0	-3	62
52	71	NC(CCC(O)CC(CCC(O)=O)CCO)CC(O)=O	0	-4	73
53	10	NC1CCC(CC(CC(O)=O)C(O)=O)CC1	0	-2	55
54	63	NC1CCC(CC(O)CCC(O)=O)CC1	0	-2	62
55	28	OC(=O)C=O	0	-1	100
56	52	NC1CCC(CC(CC(O)=O)C(O)=O)COC1=O	0	-5	61
57	40	NC1CCC(CC(C(=O)CC(O)=O)C(O)=O)CC1	0	-4	76
58	26	OCC=O	0	-2	100
59	27	OCC(O)=O	0	-1	100
60	18	C=CC(=O)CCC(O)=O	0	0,1537	60
61	24	C1CO1	0	-0,0454	100
62	12	NC1CCC(CC(=O)CC(O)=O)CC1	0	-3	66
63	75	NC(CCC(O)CC(CC(O)=O)C(O)CC(O)=O)CC(O)=O	0	-5	71
64	51	NC1CCC(CC(CC(O)=O)C(=O)CC(O)=O)COC1=O	0	-6	68
65	74	NC(CCC(O)CC(CC(O)=O)C=CC(O)=O)CC(O)=O	0	-4	72
66	29	OC(=O)C(O)=O	0	-2	100
67	6	NC1CCC(CC(CCC(O)=O)CC(O)=O)CC1	0	-1	64
68	31	CC(O)=O	0	0,0868	100
69	35	NC1CCC(CC(CCC(=O)C(O)=O)C=O)CC1	0	0,3744	78
70	46	NC1CCC(CC(CCC(O)=O)CCO)COC1=O	0	-3	70
71	36	NC1CCC(CC(CCC(=O)C(O)=O)C(O)=O)CC1	0	-3	78
72	7	NC1CCC(CC(CC(O)=O)C=CC(O)=O)CC1	0	-2	64
73	76	NC(CCC(O)CC(CC(O)=O)C(=O)CC(O)=O)CC(O)=O	0	-6	71
74	13	NC1CCC(CC(O)=O)CC1	0	-2	58
75	25	OCCO	0	-1	100
76	5	NC1CCC(CC(CCC(O)=O)CC=O)CC1	0	-1	65
77	20	CCC(O)=O	0	0,578	100
78	77	NC(CCC(O)CC(CC(O)=O)C(O)=O)CC(O)=O	0	-5	64

 

Metabolites with a quantity < 0.001 mol/mol parent after 28 d are not considered being relevant for the PBT/vPvB assessment and, therefore their PBT/vPvB status and BCF value were not assessed.

 

Conclusion: It can be concluded that the substance is moderately biodegraded but not sufficiently in terms of criteria for inherent or readily biodegradation.