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Biodegradation in water: screening tests

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Description of key information

The substance is not readily biodegradable (according to OECD criteria).

Key value for chemical safety assessment

Biodegradation in water:
under test conditions no biodegradation observed

Additional information

Parent compound:


The test item (CAS 101012-97-9) was found to be not readily biodegradable (0% degradation in 28 d based on O2 consumption) following exposure in two Manometric Respirometry Tests (OECD 301F; BASF, 1986; BASF, 2011).


 


Di-tridecylamine, branched and linear (CAS 101012-97-9) is a mixture of (predominantly) di-alkyl amines with varying alkyl-chain length in a range between C24 and C27. The main fraction consists of isomers of di-tridecylamines (C26H55N). Secondary fractions were detected to have chain lengths of C13 and C39. The following structures and relative fractions were proposed:


 


Table 1: Composition of DTDA (CAS 101012-97-9) according to analytical report 17Y36412 (BASF SE, 2017)














































Isomers



Quantity



Secondary fraction: Isomers of tridecyl amines



 



Isomers of C13H29N



0.9 %



Main fraction: Homologues of Dialkyl amines



 



Isomers of C24H51N



< 0.1 %



Isomers of C25H53N



0.4 – 0.5 %



Isomers of C26H55N



92 – 94 %



Isomers of C27H57N



0.25 – 0.35 %



Secondary fraction: Homologues of trialkyl amines



 



Isomers of C39H79N and C39H81N



< 5.2 %



 


 


Predicted metabolites:


The biodegradability and the potentially forming metabolites of the Substance were predicted using the QSAR model CATALOGIC 301C v11.16 (December 2019; available in OASIS Catalogic v.5.14.1.5) for the isomer C26H55N, which represents the isomer with the highest percentage of the Substance (92 to 94%). In order to take account of the effect of linear and branched structures, a linear isomer (CAS 5910 -75 -8) and a highly branched molecule (no CAS, SMILES:CCCC(CNCC(CCC)CC(CC)CC(C)C)CC(CC)CC(C)C) were used for the prediction. Both isomers were completely within the applicability domain of the model (BASF SE; 2020).


For the screening assessment of the metabolites’ persistence, the CATALOGIC 301C model also predicted the ready biodegradability of the metabolites. The evaluation of the bioaccumulation potential of the relevant metabolites (> 0.1% of parent molecule) was based on the predicted log Kow by the CATALOGIC 301C model. In addition, the BCF base-line model v04.11 (November 2019; available in OASIS Catalogic v.5.14.1.5; see IUCLID Ch. 5.3.1) was used to predict the BCF for the relevant metabolites. The relevant metabolites with the predicted quantity, BOD (% in 28 d), log Kow, and BCF are summarized in Table 2 and Table 3.


The linear isomer of C26H55N was predicted to be readily biodegradable (72% BOD of ThOD in 28 d), while the branched isomer of C26H55N failed the criterion for ready biodegradability (51% BOD of ThOD in 28 d). In case of the linear isomer 51 metabolites were predicted with 4 metabolites with a fraction of > 0.001 mol/mol parent, which is equivalent to > 0.1%. All four metabolites were predicted to be readily biodegradable (63–76% BOD of ThOD in 28 d; Table 2). Therefore, the relevant metabolites of the linear isomer are assessed to be neither P nor vP.


 


Table 2: QSAR prediction for CAS 101012-97-9 (isomer: C26H55N, linear) using CATALOGIC 301C v11.16 – December 2019 (OASIS CATALOGIC v5.14.1.5; only metabolites with a quantity > 0.001 mol/mol parent (> 0.1%) after 28 d are listed; metabolite no: according to (Q)SAR model Catalogic v11.16 – December 2019 (OASIS CATALOGIC v5.14.1.5))


 




























































#



Metabolite
No #



Name (CAS No., Smiles)



Quantity
(mol/mol parent)



BOD prediction
(% after 28 d)



LogKow



BCF     



parent



1



Tridecanamine, N-tridecyl-, branched and linear: C26H54-NH, linear (CCCCCCCCCCCCCNCCCCCCCCCCCCC)



0.0662



72



11.61



7.1



1



27



Tridecylamine (CAS 2869-34-3; CCCCCCCCCCCCCN)



0.27



73



5.26



1549     



2



51



3-(Tridecylammonio) propanoate (CCCCCCCCCCCCCNCCC(O)=O)



0.0997



76



2.266



4.68     



3



54



Ethylamine (CAS 75-04-7; CCN)



0.0340



63



-0.15



3.39     



4



52



N-Ethyl-1-tridecanamine (CAS 59570-06-8; CCCCCCCCCCCCCNCC)



0.0297



74



6.21



398         



 


The number of metabolites was higher for the branched isomer (n = 95) with 24 reaching a quantity of > 0.001 mol/mol parent (Table 3). Four of the relevant metabolites are predicted to be readily biodegradable. The remaining 20 relevant metabolites reach a BOD between 35 to 56% BOD of ThOD in 28 d and should be regarded as not readily biodegradable.


Therefore, the metabolites are assessed to be potentially P/vP from a precautionary point of view, but they do not meet the criteria for B/vB substances (BCF values < 2000 L/kg, see IUCLID Ch. 5.3.1).


Besides QSAR modelling, the relevant degradation products were also checked if they were registered under the REACH Regulation 1907/2006. None of the substances were registered in the ECHA disseminated database.


It can be concluded that none of the predicted and relevant metabolites meet the criteria for P/vP as well as B/vB substances; therefore, they are not PBT and not vPvB.


 


Table3:QSAR prediction for CAS 101012-97-9 (isomer: C26H55N, branched) using CATALOGIC 301C v11.16 – December 2019 (OASIS CATALOGIC v5.14.1.5; only metabolites with a quantity > 0.001 mol/mol parent (> 0.1%) after 28 d are listed; metabolites with a BOD of < 60% (nRBD) and log Kow > 3 are highlighted by bold type; metabolite no: according to (Q)SAR model Catalogic v11.16 – December 2019 (OASIS CATALOGIC v5.14.1.5))


 
















































































































































































































































#



Metabolite
No #



Name (CAS No, Smiles)



Quantity
(mol/mol parent)



BOD prediction
(% after 28 d)



LogKow



BCF    



parent



1



Tridecanamine, N-tridecyl-, branched and linear: C26H54-NH, branched (CCCC(CC(CC)CC(C)C)CNCC(CCC)CC(CC)CC(C)C)



5.20E-05



51



11.17



7.2



1



16



CCC(CCCNCC(CC(CC)CC(C)C)C(O)=O)CC(C)C



0.1681



49



4.35



5.5



2



23



2-Ethyl-4-methylpentanoic acid (CAS 108-81-6; CCC(CC(C)C)C(O)=O)



0.1427



39



2.89



4.57



3



55



(2S,4S)-2-(Aminomethyl)-4-ethyl-6-methylheptanoic acid (CAS 849487-76-9; CCC(CC(C)C)CC(CN)C(O)=O)



0.1403



43



-0.38



3.47



4



24



(2Z)-2-Ethyl-4-methyl-2-pentenoic acid (CCC(=CC(C)C)C(O)=O)



0.1241



67



2.80



12.3



5



36



CCC(CCCN)CC(C)C



0.1148



43



3.63



107.15



6



25



 (2S,3S)-2-Ethyl-3-hydroxy-4-methylpentanoic acid (CAS 73199-02-7; CCC(C(O)C(C)C)C(O)=O)



0.1079



65



1.35



3.09



7



27



(2R,3S)-3-Hydroxy-4-methyl-2-vinylpentanoic acid (CAS 458523-92-7; CCC(C(=O)C(C)C)C(O)=O)



0.09375



56



0.84



3.09



8



15



CCC(CC(C)C)CC(CNCC(CC(CC)CC(C)C)C(O)=O)C(O)=O



0.06011



42



2.95



5.25



9



17



CCC(CCCNCCCC(CC)CC(C)C)CC(C)C



0.05012



47



8.37



16.21



10



8



CCCC(CC(CC)CC(C)C)CNCC(CC(CC)CC(C)C)C(O)=O



0.01192



48



5.75



6.61



11



46



CCC(CC(C)C)CC(C(O)=O)C(O)=O



0.01037



67



2.46



4.07



12



39



CCCC(CC(CC)CC(C)C)C(O)=O



0.007628



46



5.27



40.74



13



48



CCCC(CC(CC)CC(C)C)CN



0.007628



62



5.03



467.74



14



84



CCC(CC(C)C)CC(CNCCC(O)=O)C(O)=O



0.004622



46



-0.76



3.71



15



73



CCC(CC(C)C)CC(CNCC(CC(CC)CC(C)C(O)=O)C(O)=O)C(O)=O



0.002876



35



1.71



5.12



16



74



CCC(CC(C)C)CC(CNCC(CC(CC)C=C(C)C(O)=O)C(O)=O)C(O)=O



0.0025



38



1.63



4.79



17



85



CCC(CCCNCC(C(O)=O)C(O)=O)CC(C)C



0.002311



46



-0.76



3.72



18



75



CCC(CC(C)C)CC(CNCC(CC(CC)C(O)C(C)C(O)=O)C(O)=O)C(O)=O



0.002173



38



0.17



4.37



19



77



CCC(CC(C)C)CC(CNCC(CC(CC)C(=O)C(C)C(O)=O)C(O)=O)C(O)=O



0.001889



43



-0.34



4.37



20



78



CCC(CC(C)C)CC(CNCC(CC(CC)C(O)=O)C(O)=O)C(O)=O



0.001642



38



0.31



4.47



21



79



CCC(CC(C)C)CC(CNCC(C=C(CC)C(O)=O)C(O)=O)C(O)=O



0.001427



43



0.23



4.17



22



19



CCC(CCC(O)=O)CC(C)C



0.001318



52



3.87



8.32



23



80



CCC(CC(C)C)CC(CNCC(C(O)C(CC)C(O)=O)C(O)=O)C(O)=O



0.001241



43



-1.23



3.8



24



82



CCC(CC(C)C)CC(CNCC(C(=O)C(CC)C(O)=O)C(O)=O)C(O)=O



0.001078



48



-1.74



3.8