3-aminomethyl-3,5,5-trimethylcyclohexylamine

Biodegradation in soil

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in soil: simulation testing

Remarks:

Prediction of degradation products using CATALOGIC 301 C v .09.13

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 v5.11.19

2. MODEL (incl. version number)
CATALOGIC 301C v.09.13

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 and degradation products using OASIS Catalogic v5.11.19 BOD 28 days MITI (301 C v .09.13).

GLP compliance:

no

Test type:

other: QSAR

Oxygen conditions:

aerobic

Remarks on result:

other: The applied QSAR model was used to predict the identity and quantity of the degradation products of the substance.

Transformation products:

yes

-Concomitant predictions:

Not ready degradable

Primary Half Life = 9.24 days

Ultimae Half Life = 3m 27d

 

- Predicted value (model result): O2 -consumption (BOD) = 0.15 ± 0.0172

 

Predicted metabolites:

 

Table: QSAR prediction for CAS 2855-13-2 (3-aminomethyl-3,5,5-trimethylcyclohexylamine (IPDA) using CATALOGIC 301 C v .09.13 - June, 2016; metabolites with a quantity > 0. 1 % parent after 28 d are highlighted by bold type; metabolite no: according to (Q)SAR model Catalogic v09.13)

No	Metabolite no	Smiles	Level	Transformation no	Transformation name	Quantity (%)	Log Kow	BOD prediction % 80D (28 d)
1	13	CC1(C)CC(N)CC(C)(C(O )=O}C1	2	66	Aldehyde Oxidation	14,82	-1,06	9
2	Parent	CC1(C)CC(N)CC(C)(CN)C1	0			12,23	1,90	15
3	66	CC(C)(CC(C)(C)C(O)=O)C(O)=O	7	66	Aldehyde Oxidation	7,011	1,48	0
4	68	CC(C)(CC(C)(CC(O)=O)C(O)=O)C(O)=O	7	66	Aldehyde oxidation	10,56	0,73	0
5	57	CC(C)(C)CC(C)(CO)C(O)=O	6	346	Decarboxylation	6,41	1,84	1
6	35	CC/C)/CC/C)/CC/0)=0)CN)C/0)=0	4	66	Aldehvde Oxidation	5,713	-2,70	7
7	33	CC/C)/CC/O)=OlCC/C)/CN)C/0)=0	4	66	Aldehvde Oxidation	5,713	-2,70	22
8	46	CC(C)(CC(C)(C)CN)C(O)=O	5	346	Decarboxylation	4,54	-1,37	8
9	45	CC{C){C)CC{C){CN)C{O)=O	5	346	Decarboxylation	4,54	-1,37	22
10	107	CC(C)(C)C(O)=O	14	319	Decarboxylation	4,097	1,45	0
11	47	CC(C)(CC(O)=O)CC(C)(CO)C(0)=O	5	309	Ester hydrolysis	3,519	0,51	1
12	12	CC1(C)CC(C)(CN)CC( =O) OC1	2	184	Bayer-Villiger oxidation	2,192	0,95	13
13	11	CC1(C)CC(=O)OCC(C)(CN)C1	2	184	Bayer-Villiger oxidation	2,192	0,95	17
14	74	CC/Cl/CC/Cl/CO)C/Ol=OlC/O)=O	8	487	Methvl arouo oxidation	2,06	0,01	0
15	25	CC1(C(O)=O)CC(N)CC(C)(CN)C1	3	66	Aldehyde Oxidation	1,751	-2,54	18
16	38	CC1(C)CC( C)(C(O)=O)CC( =O)OC1	4	184	Bayer-Villiqer oxidation	1,37	1,18	8
17	37	CC1(C)CC(=O) OCC(C)(C(O)=O)C1	4	184	Bayer-Villiqer oxidation	1,37	1,18	5
18	73	CC{CC{C){C)C)C{O)=O	8	216	Decarboxylation	1,082	2,85	20
19	26	CC1(C)CC(N)CC(CN)(C(O)=O)C1	3	66	Aldehyde Oxidation	0,8757	-2,54	25
20	85	CC(=CC(C)(C)C)C(0)=0	10	315	Beta-oxidation	0,8469	2,76	29
21	90	CC(C(O)C(C)(C)C)C(O)=O	11	310	Beta-oxidation	0,7361	1,31	27
22	102	CC/C/=O)C/C)/C)C)C/O)=O	13	71	Keto-enol tautomerism	0,6399	0,80	41
23	77	CC(CC(O)=O)(CC(C)(CN)C(O)=O)C(O)=O	8	66	Aldehyde oxidation	0,4864	-3,94	36
24	60	CC(CC(O)=O)(CC{C)(CO)C(O)=O)CN	6	309	Ester hydrolysis	0,4158	-4,17	8
25	76	CC(CC(O)=O)(CC(C)(CO)C(O)=O)C(O)=O	8	487	Methyl group oxidation	0,3756	-0,73	0
26	112	CC/=C/O)C/C)(O)CC(O)=O)C/O)=O	16	315	Beta-oxidation	0,3542	-1,00	89
27	70	CC(C)(CC(C)(CO)C(O)=O)CN	7	346	Decarboxylation	0,3304	-2,83	7
28	105	CC(C)(C)CCC(O)=O	13	319	Decarboxylation	0,2703	2,43	32
29	104	CC(CC(C)(O)CC(O)=O)C(O)=O	13	216	Decarboxylation	0,2699	-0,44	66
30	79	CC(C)(CC(CC(O)=O)(CN)C(O)=O)C(O)=O	8	66	Aldehyde oxidation	0,2432	-3,94	25
31	61	CC(C)(CC(O)=O)CC(CN)(CO)C(O)=O	6	309	Ester hydrolysis	0,2079	-4,17	31
32	106	CC(C)(CC(=O)CC(O)=O)C(O)=O	13	340	Decarboxylation	0,1833	-0,95	28
33	71	CC(C)(C)CC(CN)(CO)C(0)=0	7	346	Decarboxylation	0,1652	-2,83	32
34	50	CC1{CN)CC{=O)OCC{C){C{O)=O)C1	5	184	Bayer-Villiaer oxidation	0,1618	-3,49	11
35	49	CC1/C/Ol=OlCC/=OlOCC/Cl/CNlC1	5	184	Baver-Villiaer oxidation	0,1618	-3,49	28
36	110	CC/C)/CO)C/O)=O	15	487	Methvl arouo oxidation	0,157	-0,02	0
37	101	CC(C)CC(CC(O)=O)C(O)=O	12	216	Decarboxylation	0,135	1,06	72
38	9	CC1(C)CC(N)C(=O )OC(C)(CN)C1	1	747	Bayer-Villiger oxidation	0,1068	-0,60	17
39	8	CC1 (C )CC( C)( CN)CC( N)C( =0)01	1	747	Bayer-Villiger oxidation	0,1068	-0,60	14
40	44	CC(C)(CC(=O)CC(C){O)C=O)C(O)=O	4	357	Oxidative deamination and N-dealkylation	0,0988	-1,21	34
41	41	CC(C)(O)CC(=O)CC{C){C=O)C{0)=0	4	357	Oxidative deamination and N-dealkylation	0,0988	-1,21	68
42	21	CC(C)(CC(N)CC(C)(O)CN)C(O)=O	2	309	Ester hydrolvsis	0,09499	-3,89	23
43	18	CC(C)(O)CC( N)CC(C)(CN)C(O)=O	2	309	Ester hydrolvsis	0,09499	-3,89	39
44	100	CC(C)(CC(O)(CC(O)=O)C(O)=O)C(O)=O	12	164	Beta-oxidation	0,08658	-0,61	25
45	52	CC1(C)CC{CN){C/O)=O)CC/=O)OC1	5	184	Bayer-Villiaer oxidation	0,08092	-3,49	31
46	51	CC1(C)CC(=O)OCC(CN)(C(O)=O)C1	5	184	Bayer-Villiaer oxidation	0,08092	-3,49	29
47	86	CC(CC(C)(CO)C(O)=O)(CO)C(O)=O	10	487	Methyl ciroup oxidation	0,07865	-1,04	0
48	91	CC(CC(C)(CC(O)=O)C(O)=O)C(O)=O	11	216	Decarboxylation	0,07059	0,28	34
49	64	CC(C)(C)CC(C)(O)C=O	6	357	Oxidative deamination and N-dealkylation	0,06711	1,09	25
50	63	CC(C)(O)CC(C)(C)C=O	6	357	Oxidative deamination and N-dealkylation	0,06711	1,09	8
51	109	CC(=CC(C)(O)CC(O)=O)C(O)=O	14	164	Beta-oxidation	0,0613	-0,53	70
52	32	CC( C)( CC(=O) CC(C)(0)CN)C( 0)=0	3	356	Oxidative deamination and N-dealkylation	0,05934	-4,39	23
53	29	CC( C)( O)CC( =O)CC(C)( CN)C( 0)=0	3	356	Oxidative deamination and N-dealkylation	0,05934	-4,39	45
54	1	CC1(C)CC(=O)CC(C)(CN)C1	1	762	Oxidative deamination and N-dealkylation	0,05626	1,40	28
55	111	CC(C(O)C(C)(O)CC(O)=O)C(O)=O	15	310	Beta-oxidation	0,05328	-1,57	74
56	43	CC(Cl{CC{O)=O)CC{Cl{O)CN	4	123	Decarboxvlation	0,05073	-2,83	20
57	42	CC(C)(O)CC(C)(CC(O)=O)CN	4	123	Decarboxylation	0,05073	-2,83	12
58	54	CC(C){C)CC(C)(O)CN	5	346	Decarboxylation	0,04031	1,11	18
59	53	CC(C)(O)CC(C)(C)CN	5	346	Decarboxylation	0,04031	1,11	13
60	10	CC1(C)CC(N)CC(C)(CN)OC1=O	1	747	Bayer-Villiger oxidation	0,0316	-0,60	25
61	7	CC1(C)CC(N)CC(C)(CN)C(=0)01	1	747	Bayer-Villiqer oxidation	0,0316	-0,60	44
62	6	CC1 (C)CC( C)( CN)CC( N)OC1=O	1	747	Bayer-Villiqer oxidation	0,0316	1,15	13
63	5	CC1(C)CC(N)OC(=O)C(C)(CN)C1	1	747	Bayer-Villiqer oxidation	0,0316	1,15	24
64	20	CC1(C)CC(=O)C(=O)OC(C)(CN)C1	2	356	Oxidative deamination and N-dealkylation	0,01975	0,93	24
65	19	CC1(C)CC( C)(CN)CC(=O)C(=0)01	2	356	Oxidative deamination and N-dealkylation	0,01975	0,93	16
66	81	CC(CC/CC/O)=O)/CO)C/O)=O)/CO)C/O)=O	9	488	Methvl arouo oxidation	0,01467	-1,49	0
67	80	CC(CC(O)=O)(CC(CO)(CO)C(O)=O)C(O)=O	9	488	Methyl ciroup oxidation	0,01467	-1,79	0
68	99	CC(C)(C)CC(C(O)=O)C(O)=O	12	66	Aldehyde oxidation	0,004702	1,03	37
69	97	CC(=CC(C)(CC(O)=O)C(O)=O)C(O)=O	12	315	Beta-oxidation	0,0004693	0,20	62
70	2	CC1(C)CC(N)CC(C)(C=O)C1	1	357	Oxidative deamination and N-dealkylation	0,000395	1,88	12
71	36	CC/C)/CC/C)/CC/O)=O)CN)C=O	4	93	Primarv hvdroxvl arouo oxidation	0,0001756	-2,37	10
72	34	CC/C)/CC/O)=OlCC/C)/CN)C=O	4	93	Primarv hvdroxvl arouo oxidation	0,0001756	-2,37	26
73	23	CC(C)(CC(C)(CC( O)=O)CN)CO	3	309	Ester hydrolvsis	0,0001756	-2,34	10
74	22	CC(C)(CC(O)=O)CC(C)(CN)CO	3	309	Ester hydrolvsis	0,0001756	-2,34	26
75	58	CC/Cl/CC/C)/CC/Ol=O)C/O)=O)C=O	6	93	Primarv hvdroxvl arouo oxidation	0,0001097	0,48	5
76	48	CC(C)(CC(C)(CC(O)=O)C(O)=O)CO	5	309	Ester hydrolvsis	0,0001097	0,51	5
77	56	CC(C)(CC(C)(C)C=O)C(O)=O	6	357	Oxidative deamination and N-dealkylation	0,00007558	1,81	5
78	55	CC(C)(C)CC(C)(C=O)C(0)=0	6	357	Oxidative deamination and N-dealkylation	0,00007558	1,81	30
79	96	CC/=C/O)C/C)/C)C)C/O)=O	12	315	Beta-oxidation	0,00004894	1,88	41
80	14	CC1/C=O)CC/N)CC/C)/CN)C1	2	93	Primarv hvdroxvl arouo oxidation	0,00004668	0,41	21
81	3	CC1(C O)CC( N)CC(C)( CN)C1	1	487	Methyl i:iroup oxidation	0,00004668	0,44	21
82	108	CCC/O)=O	14	319	Decarboxylation	0,00004254	0,58	100
83	15	CC1/C)CC/ N)CC/CN)/C=O)C1	2	93	Primarv hvdroxvl arouo oxidation	0,00002334	0,41	28
84	4	CC1(C)CC(N)CC(CN)(CO)C1	1	488	Methyl i:iroup oxidation	0,00002334	0,44	28
85	75	CC(C)(CC(C)(CO)C(O)=O)C=O	8	357	Oxidative deamination and N-dealkylation	0,00001591	0,35	5
86	69	CC(CC(O)=O){CC(C)(CN)C=O)C(O)=O	7	93	Primary hydroxvl arouo oxidation	0,00001296	-4,19	39
87	59	CC{CC(O)=O)(CC(C){CN)CO)C(O)=O	6	309	Ester hydrolvsis	0,00001296	-4,17	39
88	67	CC{Cl/CC/Cl/CO)C/O)=O)CO	7	487	Mettwl arouo oxidation	0,00001041	0,78	5
89	82	CC(CC(O)=O)(CC(C)(C=O)C(O)=O)C(O)=O	9	357	Oxidative deamination and N-dealkylation	0,000008098	-0,76	54
90	65	CC{C){C)CC{C){C{O)=O)C{O)=O	7	66	Aldehyde oxidation	0,000007558	1,48	27
91	72	CC(C){CC{CC{O)=O){CN)C{O)=O)C=O	7	93	Primary hydroxvl ciroup oxidation	0,000006481	-4,19	29
92	62	CC(C)(CC(CC(O)=O)(CN)C(O)=O)CO	6	309	Ester hydrolysis	0,000006481	-4,17	29
93	103	CC(CC(O)=O)C=C/C)C/O)=O	13	216	Decarboxylation	0,000004688	0,98	71
94	84	CC(C)(CC(CC(O)=O)(C=O)C(O)=O)C(O)=O	9	357	Oxidative deamination and N-dealkylation	0,000004049	-0,76	37
95	93	CC(C)(C)CC(C=O)C(0)=0	11	93	Primary hydroxvl ciroup oxidation	0,00000275	1,36	40
96	88	CC(C)(C)CC(CO)C(O)=O	10	216	Decarboxylation	0,00000275	1,38	40
97	78	CC(C)(C)CC(CO)(C=O)C(0)=0	8	357	Oxidative deamination and N-dealkylation	0,00000275	0,35	44
98	94	CC(C)(CC(CC(O)=O)C/O)=O)C(0)=0	11	216	Decarboxylation	0,000002699	0,28	29
99	92	CC(CC(O)=O)CC(C)(C(O)=O)C(O)=O	11	216	Decarboxylation	0,000002699	0,28	62
100	28	CC(C)(CC(C)(CC=O)CN)C(O)=O	3	37	Oxidative deamination and N-dealkylation	0,000002531	-2,37	10
101	27	CC(C)(CC=O)CC( C)(CN)C(0)=0	3	37	Oxidative deamination and N-dealkylation	0,000002531	-2,37	26
102	17	CC/C)/CC/C)/CC/N)O) CN)C/ 0)=0	2	309	Ester hvdrolvsis	0,000002531	-3,89	10
103	16	CC/C)/CC/N)O)CC/C)/CN)C/O)=O	2	309	Ester hvdrolvsis	0,000002531	-3,89	26
104	31	CC( C)( CC(=O) C(O)=O)CC( C)( O)CN	3	309	Ester hydrolysis	0,000001581	-0,96	24
105	30	CC( C)( O)CC( C)( CC(=O)C(O)=O)CN	3	309	Ester hydrolysis	0,000001581	-0,96	16
106	83	CC(C)(C)CC(CO)(C(O)=O)C(0)=0	9	66	Aldehyde oxidation	0,000000275	0,01	42
107	98	CC(0)(CC(0)=O)CC(C)(C(0)=O)C(O)=O	12	164	Beta-oxidation	2,699E-07	-1,22	60
108	95	CC(C)CC(CC(O)=O)(C(O)=O)C(O)=O	11	216	Decarboxylation	0,000000135	0,28	56
109	24	CC1(C)CC(=O)CC( C)(C(O)=O)C1	3	356	Oxidative deamination and N-dealkylation	2,5E-09	1,63	10
110	87	CC/CC/O)=O)/CC/C\/C/O\=O)C/O)=O)C/O)=O	10	66	Aldehvde Oxidation	8E-10	-0,50	51
111	89	CC(C)(CC(CC(O)=O)(C(O)=O)C(O)=O)C(O)=O	10	66	Aldehyde oxidation	4E-10	-0,50	34
112	39	CC1(C(O)=O)CC(=O)CC(C)(CN)C1	4	356	Oxidative deamination and N-dealkylation	3E-10	-3,04	22
113	40	CC1(C)CC(=O)CC(CN)(C(O)=O)C1	4	356	Oxidative deamination and N-dealkylation	1E-10	-3,04	33

 

Conclusion:

Overall predicted metabolites: 112 metabolits

 

40 metabolites: quantity > 0.1%; thereof: 4 RBD and 40 log Kow <3.

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)

Reference 2

Endpoint:

biodegradation in soil: simulation testing

Data waiving:

exposure considerations

Justification for data waiving:

the study does not need to be conducted because direct and indirect exposure of soil is unlikely

Reason / purpose for cross-reference:

data waiving: supporting information

Description of key information

A simulation study according to OECD 303A revealed a biodegradation of 42% after 31 days in laboratory WWTP. No data are available on degradation rates in soil; therefore, the substance is regarded as P/vP from a precautionary point of view.

Degradation products were predicted using a QSAR model. 4 of 40 relevant degradation products are readily biodegradable.

Additional information

QSAR-disclaimer:

In Article 13 of Regulation (EC) No 1907/2006, it is laid down that information on intrinsic properties of substances may be generated by means other than tests, provided that the conditions set out in Annex XI (of the same Regulation) are met.

According to Annex XI of Regulation (EC) No 1907/2006 (Q)SAR results can be used if (1) the scientific validity of the (Q)SAR model has been established, (2) the substance falls within the applicability domain of the (Q)SAR model, (3) the results are adequate for the purpose of classification and labelling and/or risk assessment and (4) adequate and reliable documentation of the applied method is provided.

For the assessment of the substance, (Q)SAR results were used for the prediction of potential degradation products. The criteria listed in Annex XI of Regulation (EC) No 1907/2006 are considered to be adequately fulfilled and therefore the endpoint(s) sufficiently covered and suitable for risk assessment.

Therefore, experimental simulation testing in soil is not provided.

 

Assessment:

A simulation study according to OECD 303A revealed a biodegradation of 42% after 31 days in laboratory WWTP.

According to REACH Annex IX, 9.2.1.3, column 1, a test on biodegradation in soil is only required for substances with a high potential for adsorption to soil. Since the test substance has a calculated log Koc of 2.97 at pH7 it is expected to have a low potential for adsorption to soil and sediment. According to a Mackay Level I model calculation, the main target compartment for isophorone diamine will be the hydrosphere (99.8 %), followed by sediment and soil with a percentage of just 0.08 % each. Therefore, no biodegradation test in soil is required.

The degradation products of IPDA are predicted via QSAR modelling of degradability and bioaccumulation for the PBT/vPvB assessment. None of the relevant degradation products has a high potential for adsorption to soil considering the calculated logKow.

Moreover, in accordance with Annex XI Section 3 and Annex IX 9.2.1.3, column 2, it is demonstrated in the risk assessment that the manufacture and all uses of the lifecycle of the substance do not pose an unacceptable risk for environmental compartments. In the chemical safety report operational conditions (OC) and risk mitigating measures (RMM) define how direct or indirect exposure into the environment is prevented and it is demonstrated that the risk characterization ratios (RCRs) of the chemical safety assessment are below 1 for all compartments (see Chemical Safety Report).

The degradation products of IPDA are predicted via QSAR modelling of degradability and bioaccumulation for the PBT/vPvB assessment. None of the relevant degradation products has a high potential for adsorption to soil considering the calculated logKow.

Moreover, in accordance with Annex XI Section 3 and Annex IX 9.2.1.4, column 2, it is demonstrated in the risk assessment that the manufacture and all uses of the lifecycle of the substance do not pose an unacceptable risk for environmental compartments. In the chemical safety report operational conditions (OC) and risk mitigating measures (RMM) define how direct or indirect exposure into the environment is prevented and it is demonstrated that the risk characterization ratios (RCRs) of the chemical safety assessment are below 1 for all compartments (see Chemical Safety Report).

 For the persistence assessment, the substance itself is assessed to be P/vP from a precautionary point of view. Potentially forming degradation products have been predicted using a valid QSAR model (CATALOGIC 301 C v .09.13). The substance is within the applicability domain of the model. The model predicted 112 degradation products, of which 40 can be regarded as relevant based on their predicted quantity (see the corresponded endpoint study record). These relevant degradation products were evaluated with regard to their biodegradability and bioaccumulation potential based on QSAR data. 4 substances were readily biodegradable. Significant accumulation is not to be expected for all relevant biodegradation products as their logKow <3. Thus, they are neither PBT, nor vPvB.