2,2'-dimethyl-4,4'-methylenebis(cyclohexylamine)

Biodegradation in water: screening tests

Description of key information

Not readily biodegradable (according to OECD criteria).

Key value for chemical safety assessment

Biodegradation in water:

not biodegradable

Type of water:

freshwater

Additional information

Parent compound:

Concerning the biodegradation potential of 4,4'-methylenebis(2-methylcyclohexanamine) (CAS 6864 -7 -5, DMDC) in water, a test performed by NITE (Japan, 2001) according to OECD TG 301C is selected as key study. In this study mixed inoculum according to MITI was used. After 28 days no significant biodegradation was oberserved (0% BOD/ThOD). Further studies performed by BASF 1977 and 1990 (according to OECD 302B) support this result. The result is supported by the model CATALOGIC 301C v11.15 (OASIS Catalogic v5.13.1). The model predicted that the substance would be degraded to 39% after 28 d based on oxygen consumption (BASF SE, 2019). The substance was within the applicability domain of the model. The model was used to predict potential metabolites of DMDC.

Metabolites:

Metabolites (n = 128) from the degradation of 4,4'-methylenebis(2 -methylcyclohexanamine (CAS 6864 -37 -5) were predicted using the QSAR model Catalogic 301C v11.15. The metabolites are identified by the Smiles code. The table below also lists the estimated quantity of appearance from the degradationas well as the log Kow and the biodegradability (BOD prediction). The metabolites with a quantity of > 0.001 mol/mol parent are regarded to be relevant for the environmental assessment. It was attempted to identify the relevant metabolites either via the QSAR Toolbox and/or the advanced search option for substances on the ECHA website. In case a name and/or CAS number was assigned, the PBT/vPvB status acording to the ECHA website was checked.

Based on the available information, it can be concluded that only three metabolites (metab. no. 2, 117, 123) have a log Kow > 3. In addition, these substances are not readily biodegradable. However, as their predicted quantitiy is below 0.001 mol/mol parent, they are not relevant for the PBT assessment of the parent substance's metabolites.

37 of the 128 metabolites have a predicted quantity of > 0.001 mol/mol parent and are regarded as relevant for further assessment. 26 of these metabolites are not readily biodegradable, but all of these 37 metabolites have a log Kow < 3; therefore, a significant bioaccumulation potential is not expected. It can be concluded that these substances are not PBT/vPvB substances.

Their toxicity (T) was not further assessed as no critical combination of potential P/vP (= not readily biodegradable) and potential B/vB (log Kow > 3) properties was observed.

Table: QSAR prediction for CAS-#6864 -37 -5 using CATALOGIC 301C v11.15 – July 2018 (OASIS CATALOGIC v5.13.1.156; 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 v11.15 – July 2018 (OASIS CATALOGIC v5.13.156))

#	Metab. No	Smiles	Name	Quantity (mol/mol parent)	Log Kow	BOD pred. (% after 28 d)	PBT-Assessment: ECHA (disseminated substances)
Parent	1	CC1CC(CC2CCC(N)C(C)C2)CCC1N	4,4'-Methylenebis(2-methylcyclohexanamine) (CAS 6864-37-5)	1.24E-01	2.30	39	not PBT/vPvB
1	2	CC1CC(CC2CCC(=O)C(C)C2)CCC1N	not identified	7.95E-06	3.60	56	not checked
2	3	CC1CC(CC2(O)CCC(=O)C(C)C2)CCC1N	not identified	7.95E-06	2.09	55	not checked
3	4	CC1CC(CC2(O)CCC(=O)OC(C)C2)CCC1N	not identified	8.82E-02	1.64	54	not identified
4	5	CC1CC(CC(O)(CCC(O)=O)CC(C)O)CCC1N	not identified	7.07E-06	-1.24	58	not checked
5	6	CC1CC(CC(O)(CC(C)O)C=CC(O)=O)CCC1N	not identified	7.07E-06	0.04	58	not checked
6	7	CC1CC(CC(O)(CC(C)O)C(O)CC(O)=O)CCC1N	not identified	7.07E-06	-2.78	57	not checked
7	8	CC1CC(CC(O)(CC(C)O)C(=O)CC(O)=O)CCC1N	not identified	7.07E-06	-2.37	57	not checked
8	9	CC1CC(CC(O)(CC(C)O)C(O)=O)CCC1N	not identified	2.17E-01	-1.91	50	not identified
9	10	CC1CC(CC(O)(CC(C)=O)C(O)=O)CCC1N	not identified	4.90E-06	-2.83	58	not checked
10	11	CC1CC(CC(O)(COC(C)=O)C(O)=O)CCC1N	not identified	5.44E-02	-2.22	56	not identified
11	12	CC1CC(CC(O)(CO)C(O)=O)CCC1N	not identified	4.35E-06	-1.62	52	not checked
12	13	CC1CC(CC(O)(C=O)C(O)=O)CCC1N	not identified	4.35E-06	-3.25	52	not checked
13	14	CC1CC(CC(O)(C(O)=O)C(O)=O)CCC1N	not identified	4.48E-02	-3.59	50	not identified
14	15	CC1CC(CC(=O)C(O)=O)CCC1N	not identified	3.91E-06	0.39	58	not checked
15	16	CC1CC(CC(O)=O)CCC1N	not identified	3.91E-06	-1.48	56	not checked
16	17	CC1CC(O)(CC(O)=O)CCC1N	not identified	1.25E-01	-2.98	54	not identified
17	18	CC1CC(=O)CCC1N	not identified	9.95E-02	0.00	49	not identified
18	19	CC1CC(=O)CCC1=O	not identified	1.66E-06	-0.51	77	not checked
19	20	CC1CC(=O)CCC(=O)O1	not identified	1.84E-02	0.85	76	not identified
20	21	CC=CC(=O)CCC(O)=O	not identified	1.47E-06	0.57	85	not checked
21	22	OC(=O)CCC(O)=O	Succinic acid (CAS 110-15-8)	1.52E-02	-0.75	90	not PBT/vPvB
22	23	CCC(O)=O	Propionic acid (CAS 79-09-4)	1.35E-06	0.58	100	not checked
23	26	CC=C	Propene (CAS 115-07-1)	1.47E-06	1.68	80	not checked
24	27	CC1CO1	Methyloxirane (CAS 75-56-9)	1.47E-06	0.37	77	not checked
25	28	CC(O)CO	1,2-Propanediol (CAS 57-55-6)	1.47E-06	-0.78	73	not checked
26	29	CC(O)C=O	not identified	1.47E-06	-1.21	73	not checked
27	30	CC(O)C(O)=O	D-lactic acid (CAS 10326-41-7)	4.73E-02	-0.65	68	not PBT/vPvB
28	31	CC=O	Acetaldehyd (CAS 75-07-0)	1.00E-06	-0.17	100	not checked
29	32	CC(O)=O	Acetic acid (CAS 64-19-7)	1.61E-05	0.09	100	not checked
30	34	CC1CC(CC2CCC(N)C(CO)C2)CCC1N	not identified	4.70E-07	2.64	48	not checked
31	35	CC1CC(CC2CCC(N)C(C=O)C2)CCC1N	not identified	4.70E-07	2.61	48	not checked
32	36	CC1CC(CC2CCC(N)C(C(O)=O)C2)CCC1N	not identified	6.61E-03	-0.34	46	not identified
33	37	CC1CC(CC2CCC(N)C(C(O)=O)C2)CCC1=O	not identified	2.02E-07	-0.84	57	not checked
34	38	CC1CC(O)(CC2CCC(N)C(C(O)=O)C2)CCC1=O	not identified	2.02E-07	-2.34	56	not checked
35	39	CC1CC(O)(CC2CCC(N)C(C(O)=O)C2)CCC(=O)O1	not identified	2.24E-03	-2.79	55	not identified
36	40	CC(O)CC(O)(CCC(O)=O)CC1CCC(N)C(C(O)=O)C1	not identified	1.79E-07	-3.06	62	not checked
37	41	CC(O)CC(O)(CC1CCC(N)C(C(O)=O)C1)C=CC(O)=O	not identified	1.79E-07	-3.28	62	not checked
38	42	CC(O)CC(O)(CC1CCC(N)C(C(O)=O)C1)C(O)CC(O)=O	not identified	1.79E-07	-4.60	61	not checked
39	43	CC(O)CC(O)(CC1CCC(N)C(C(O)=O)C1)C(=O)CC(O)=O	not identified	1.79E-07	-4.20	61	not checked
40	44	CC(O)CC(O)(CC1CCC(N)C(C(O)=O)C1)C(O)=O	not identified	5.51E-03	-3.74	55	not identified
41	45	CC(=O)CC(O)(CC1CCC(N)C(C(O)=O)C1)C(O)=O	not identified	1.24E-07	-4.65	60	not checked
42	46	CC(=O)OCC(O)(CC1CCC(N)C(C(O)=O)C1)C(O)=O	not identified	1.38E-03	-4.04	59	not identified
43	47	NC1CCC(CC(O)(CO)C(O)=O)CC1C(O)=O	not identified	1.11E-07	-3.44	57	not checked
44	48	NC1CCC(CC(O)(C=O)C(O)=O)CC1C(O)=O	not identified	1.11E-07	-5.08	57	not checked
45	49	NC1CCC(CC(O)(C(O)=O)C(O)=O)CC1C(O)=O	not identified	1.14E-03	-4.82	55	not identified
46	50	NC1CCC(CC(=O)C(O)=O)CC1C(O)=O	not identified	9.91E-08	-4.63	65	not checked
47	51	NC1CCC(CC(O)=O)CC1C(O)=O	not identified	9.91E-08	-3.30	64	not checked
48	52	NC1CCC(O)(CC(O)=O)CC1C(O)=O	not identified	3.18E-03	-4.81	62	not identified
49	53	NC1CCC(=O)CC1C(O)=O	not identified	2.53E-03	-4.44	45	not identified
50	54	OC(=O)C1CC(=O)CCC1=O	not identified	4.21E-13	-1.74	74	not checked
51	55	OC(=O)C1CC(=O)OCCC1=O	not identified	2.10E-03	-0.39	67	not identified
52	56	OC(=O)C1COC(=O)CCC1=O	not identified	2.10E-03	-0.39	78	not identified
53	57	CC1CC(CC2CCC(=O)C(C(O)=O)C2)CCC1N	not identified	2.64E-03	-0.84	62	not identified
54	58	CC1CC(CC(CCC(O)=O)CCC(O)=O)CCC1N	not identified	1.75E-12	-0.43	74	not checked
55	59	CC1CC(CC(CCC(O)=O)C=CC(O)=O)CCC1N	not identified	1.75E-07	-0.65	74	not checked
56	60	CC1CC(CC(CCC(O)=O)C(O)CC(O)=O)CCC1N	not identified	1.75E-07	-1.97	73	not checked
57	61	CC1CC(CC(CCC(O)=O)C(=O)CC(O)=O)CCC1N	not identified	1.75E-07	-2.48	73	not checked
58	62	CC1CC(CC(CCC(O)=O)C(O)=O)CCC1N	not identified	1.75E-07	-1.41	69	not checked
59	63	CC1CC(CC(C=CC(O)=O)C(O)=O)CCC1N	not identified	1.75E-07	-1.63	69	not checked
60	64	CC1CC(CC(C(O)CC(O)=O)C(O)=O)CCC1N	not identified	1.75E-07	-2.95	68	not checked
61	65	CC1CC(CC(C(=O)CC(O)=O)C(O)=O)CCC1N	not identified	1.75E-07	-3.46	68	not checked
62	66	CC1CC(CC(C(O)=O)C(O)=O)CCC1N	not identified	3.00E-04	-2.39	62	not checked
63	67	CC1CC(CCC(O)=O)CCC1N	not identified	1.72E-07	-0.99	59	not checked
64	68	CC1CC(C=CC(O)=O)CCC1N	not identified	1.72E-07	0.30	59	not checked
65	69	CC1CC(C(O)CC(O)=O)CCC1N	not identified	1.72E-07	-2.53	57	not checked
66	70	CC1CC(C(=O)CC(O)=O)CCC1N	not identified	1.72E-07	-3.04	57	not checked
67	71	CC1CC(C(O)=O)CCC1N	not identified	6.47E-03	-1.97	46	not identified
68	72	CC1CC(C(O)=O)CCC1=O	not identified	1.08E-07	0.72	77	not checked
69	73	CC1CC(O)(C(O)=O)CCC1=O	not identified	1.08E-07	-0.47	76	not checked
70	74	CC1CC(O)(C(O)=O)CCC(=O)O1	not identified	1.20E-03	-0.92	74	not identified
71	75	CC(O)CC(O)(CCC(O)=O)C(O)=O	not identified	9.57E-08	-1.19	96	not checked
72	76	CC(O)CC(O)(C=CC(O)=O)C(O)=O	not identified	9.57E-08	-1.40	96	not checked
73	77	CC(O)CC(O)(C(O)CC(O)=O)C(O)=O	not identified	9.57E-08	-1.53	95	not checked
74	78	CC(O)CC(O)(C(=O)CC(O)=O)C(O)=O	not identified	9.57E-08	-2.32	95	not checked
75	79	CC(O)CC(O)(C(O)=O)C(O)=O	not identified	2.94E-03	-2.17	93	not identified
76	80	CC(=O)CC(O)(C(O)=O)C(O)=O	not identified	6.63E-03	-3.09	91	not identified
77	82	CC1CC(CC2CC(C)C(N)CC(=O)O2)CCC1N	not identified	6.36E-04	1.60	42	not checked
78	83	CC1CC(CC(O)CC(C)C(N)CC(O)=O)CCC1N	not identified	7.17E-04	-1.69	39	not checked
79	84	CC1CC(CC(O)CC(C)C(N)CC(O)=O)CCC1=O	not identified	2.19E-08	-2.19	56	not checked
80	85	CC(CC(O)CC1(O)CCC(=O)C(C)C1)C(N)CC(O)=O	not identified	2.19E-08	-3.29	55	not checked
81	86	CC(CC(O)CC1(O)CCC(=O)OC(C)C1)C(N)CC(O)=O	not identified	2.43E-04	-3.74	53	not checked
82	87	CC(CC(O)CC(O)(CCC(O)=O)CC(C)O)C(N)CC(O)=O	not identified	1.95E-03	-4.42	59	not identified
83	88	CC1CC(CC(O)CC(C)C(=O)CC(O)=O)CCC1N	not identified	2.19E-08	-2.19	48	not checked
84	89	CC1CC(CC(O)CC(C)C(O)=O)CCC1N	not identified	2.86E-04	-1.13	40	not checked
85	90	CC1CC(CC(O)C=C(C)C(O)=O)CCC1N	not identified	1.90E-03	0.29	44	not identified
86	91	CC1CC(CC2CCC(N)C(C)C(=O)O2)CCC1N	not identified	6.36E-04	1.60	33	not checked
87	92	CC1CC(CC(O)CCC(N)C(C)C(O)=O)CCC1N	not identified	6.66E-04	-1.69	34	not checked
88	93	CC1CC(CC(O)CCC(N)=C(C)C(O)=O)CCC1N	not identified	1.42E-03	-0.14	31	not identified
89	94	CC=C(N)CCC(O)CC1CCC(N)C(C)C1	not identified	1.13E-03	2.25	30	not identified
90	95	CC=C(N)CCC(O)CC1CCC(=O)C(C)C1	not identified	1.88E-03	1.74	46	not identified
91	96	CC1CC(CC2CCC(N)C(C)OC2=O)CCC1N	not identified	6.36E-04	1.60	29	not checked
92	97	CC1CC(CC(CCC(N)C(C)O)C(O)=O)CCC1N	not identified	1.56E-03	-1.69	30	not identified
93	98	CC1CC(CC(CCC(N)C(C)=O)C(O)=O)CCC1N	not identified	1.13E-03	-1.44	33	not identified
94	99	CC1CC(CCCCC(N)C(C)=O)CCC1N	not identified	3.38E-04	2.58	36	not checked
95	100	CC1CC(CCCCC(N)C(C)=O)CCC1=O	not identified	1.03E-03	2.08	51	not identified
96	101	CC1CC(CCCCC(=O)C(C)=O)CCC1N	not identified	1.03E-03	1.77	52	not identified
97	102	CC1CC(CC2CC(C)C(N)COC2=O)CCC1N	not identified	6.36E-04	1.60	35	not checked
98	103	CC1CC(CC(CC(C)C(N)CO)C(O)=O)CCC1N	not identified	1.63E-03	-1.69	38	not identified
99	104	CC(CCCC1CCC(N)C(C)C1)C(N)CO	not identified	4.87E-04	2.33	37	not checked
100	105	CC(CCCC1CCC(N)C(C)C1)C(=O)CO	not identified	1.49E-03	2.74	44	not identified
101	106	CC(CCCC1CCC(=O)C(C)C1)C(N)CO	not identified	1.49E-03	1.83	56	not identified
102	107	CC1CC(CC2CC(C)C(N)C(=O)OC2)CCC1N	not identified	8.07E-04	1.60	34	not checked
103	108	CC1CC(CC2CC(C)C(N)C(=O)OC2)CCC1=O	not identified	2.46E-08	1.10	50	not checked
104	109	CC1CC(CC2(O)CCC(=O)C(C)C2)COC(=O)C1N	not identified	2.46E-08	-0.41	48	not checked
105	110	CC1CC(CC2(O)CCC(=O)OC(C)C2)COC(=O)C1N	not identified	2.73E-04	-0.86	47	not checked
106	111	CC1CC(CC(O)(CCC(O)=O)CC(C)O)COC(=O)C1N	not identified	2.19E-08	-3.74	54	not checked
107	112	CC1CC(CC(O)(CC(C)O)C=CC(O)=O)COC(=O)C1N	not identified	2.19E-08	-2.46	54	not checked
108	113	CC1CC(CC(O)(CC(C)O)C(O)CC(O)=O)COC(=O)C1N	not identified	2.19E-08	-5.28	53	not checked
109	114	CC1CC(CC(O)(CC(C)O)C(=O)CC(O)=O)COC(=O)C1N	not identified	2.19E-08	-4.87	53	not checked
110	115	CC1CC(CC(O)(CC(C)O)C(O)=O)COC(=O)C1N	not identified	6.72E-04	-4.41	45	not checked
111	116	CC1CC(CC(O)(CC(C)=O)C(O)=O)COC(=O)C1N	not identified	1.52E-03	-5.33	55	not identified
112	117	CC1CC(CC2CC(C)C(=O)C(=O)OC2)CCC1N	not identified	2.73E-04	3.13	42	not checked
113	118	CC1CC(CC(CC(C)C(=O)C(O)=O)CO)CCC1N	not identified	2.19E-08	1.23	42	not checked
114	119	CC1CC(CC(CC(C)C(=O)C(O)=O)C=O)CCC1N	not identified	2.19E-08	1.21	42	not checked
115	120	CC1CC(CC(CC(C)C(=O)C(O)=O)C(O)=O)CCC1N	not identified	2.25E-04	-2.32	40	not checked
116	121	CC(CCCC1CCC(N)C(C)C1)C(=O)C(O)=O	not identified	9.82E-04	2.28	43	not checked
117	122	CC1CC(CC(CC(C)C=O)C(O)=O)CCC1N	not identified	9.82E-04	-0.66	55	not checked
118	123	CC1CC(CC2CC(C)C(N)OC(=O)C2)CCC1N	not identified	6.36E-04	3.35	40	not checked
119	124	CC1CC(CC(CC(C)C(N)O)CC(O)=O)CCC1N	not identified	5.09E-08	-1.69	43	not checked
120	125	CC1CC(CC(CC(C)C=O)CC(O)=O)CCC1N	not identified	5.09E-08	-0.17	43	not checked
121	126	CC1CC(CC(CC(C)C(O)=O)CC(O)=O)CCC1N	not identified	5.09E-08	-0.50	41	not checked
122	127	CC1CC(CC(O)(CC(C)C(O)=O)CC(O)=O)CCC1N	not identified	6.66E-04	-2.01	39	not checked
123	128	CC1CC(CC(O)(CC(O)=O)C=C(C)C(O)=O)CCC1N	not identified	5.79E-04	-2.09	47	not checked
124	129	CC1CC(CC(O)(CC(O)=O)C(O)C(C)C(O)=O)CCC1N	not identified	5.03E-04	-3.14	44	not checked
125	130	CC1CC(CC(O)(CC(O)=O)C(O)=C(C)C(O)=O)CCC1N	not identified	3.35E-08	-2.57	55	not checked
126	131	CC1CC(CC(O)(CC(O)=O)C(=O)C(C)C(O)=O)CCC1N	not identified	4.38E-04	-3.14	55	not checked
127	132	CC1CC(CC(O)(CC(O)=O)C(O)=O)CCC1N	not identified	9.33E-04	-2.79	50	not checked
128	133	CC1CC(CC(=O)CC(O)=O)CCC1N	not identified	1.98E-03	-2.55	64	not identified

(metabolites which are predicted at quantity >0.001 after 28 d are highlighted in grey and written in bold letters)

(metabolite no: according to (Q)SAR model CATALOGIC 301C v11.15 – July 2018 (OASIS CATALOGIC v5.13.1.156))

Conclusion:

Summing up the available experimental and calculated data, DMDC (CAS 6864 -37 -5) is concluded to be not readily biodegradable from a precautionary point of view.