1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxyanthraquinone

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: screening tests

Type of information:

(Q)SAR

Adequacy of study:

weight of evidence

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 limited documentation / justification

Justification for type of information:

The supporting QMRF report has been attached

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I))

Principles of method if other than guideline:

The data is predicted using the OECD QSAR toolbox version 3.3 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
- Molecular formula: C34H34N2O4
- Molecular weight: 534.6526 g/mole
- Smiles notation: CCCCc1ccc(cc1)Nc2ccc(c3c2C(=O)c4c(ccc(c4C3=O)O)O)Nc5ccc(cc5)CCCC
-InChl: 1S/C34H34N2O4/c1-3-5-7-21-9-13-23(14-10-21)35-25-17-18-26(36-24-15-11-22(12-16-24)8-6-4-2)30-29(25)33(39)31-27(37)19-20-28(38)32(31)34(30)40/h9-20,35-38H,3-8H2,1-2H3
- Substance type: Organic

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Based on:

not specified

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

0

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

No degradation of test substance 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was determined in 28 days by using BOD parameter.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 6 nearest neighbours
Domain  logical expression:Result: In Domain

(((((((((("a" or "b" or "c" or "d" )  and "e" )  and "f" )  and "g" )  and "h" )  and ("i" and ( not "j") )  )  and "k" )  and "l" )  and ("m" and ( not "n") )  )  and ("o" and "p" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Hydroquinones OR Phenols, Poly by Aquatic toxicity classification by ECOSAR ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Alkyl arenes OR Anthracenone/ Antracendione OR Aromatic amine OR Aryl OR Cycloketone OR Diketone OR Fused carbocyclic aromatic OR Phenol by Organic Functional groups ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Alkyl arenes OR Anthracenone/ Antracendione OR Aromatic amine OR Aryl OR Overlapping groups OR Phenol by Organic Functional groups (nested) ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Alcohol, olefinic attach [-OH] OR Aliphatic Carbon [CH] OR Aliphatic Carbon [-CH2-] OR Aliphatic Carbon [-CH3] OR Aliphatic Nitrogen, two aromatic attach [-N-] OR Aromatic Carbon [C] OR Carbonyl, olefinic attach [-C(=O)-] OR Diarylketone OR Hydroxy, aromatic attach [-OH] OR Ketone in a ring, olefinic aromatic attach OR Miscellaneous sulfide (=S) or oxide (=O) OR Nitrogen, two or tree olefinic attach [>N-] OR Olefinic carbon [=CH- or =C<] OR Ortho-hydroxy to misc. -CO-  OR Oxygen, one aromatic attach [-O-] by Organic functional groups (US EPA) ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 7) ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 5) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 2) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Not calculated by Biodeg BioHC half-life (Biowin) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Not possible to classify according to these rules by DPRA Lysine peptide depletion

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Low reactive OR Low reactive >> Activated haloarenes OR Low reactive >> Epoxides by DPRA Lysine peptide depletion

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as High (Class III) by Toxic hazard classification by Cramer (original) ONLY

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Not bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Group 14 - Carbon C AND Group 15 - Nitrogen N AND Group 16 - Oxygen O by Chemical elements

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Group 16 - Sulfur S by Chemical elements

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 340 Da

Domain logical expression index: "p"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 544 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 0% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 28198 -05 -2) is predicted using OECD QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 0% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Various predicted data for the target compound 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione (CAS No. 28198-05-2) and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2017) using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione (CAS No. 28198-05-2) was estimated. Test substance undergoes 0% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.

 

In another prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compound 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione(CAS No. 28198-05-2) in the presence of mixed populations of environmental microorganisms was estimated. The biodegradability of the substance was calculated using seven different models such as Linear Model, Non-Linear Model, Ultimate Biodegradation Timeframe, Primary Biodegradation Timeframe, MITI Linear Model, MITI Non-Linear Model and Anaerobic Model (called as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017 and Envichem, 2014) for the read across chemical Bis(octylphenyl)amine (CAS no. 26603-23-6), biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance Bis(octylphenyl)amine. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance Bis(octylphenyl)amine was determined to be 0 and 5.2% by BOD and UV-Vis parameter in 14 days. Thus, based on percentage degradation, Bis(octylphenyl)amine is considered to be not readily biodegradable in nature.

 

For the read across chemical 4-octyl-N-(4-octylphenyl)aniline (CAS no. 101-67-7) from authoritative database (J-CHECK, 2017), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 4 -octyl-N-(4 -octylphenyl)aniline. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 4 -octyl-N-(4 -octylphenyl)aniline was determined to be 0 and 2% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 4 -octyl-N-(4 -octylphenyl)aniline is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2,2'-methylenebis(6-tert-butyl-4-methylphenol) (CAS no119-47-1) (J-CHECK, HSDB, 2017 and Envichem, 2014). Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 2,2'-methylenebis(6 -tert-butyl-4 -methylphenol) was determined to be 0 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 2,2'-methylenebis(6 -tert-butyl-4 -methylphenol) is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical1,4-bis[(4-butylphenyl)amino]-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB and Envichem), it can be concluded that the test substance 1,4 -bis[(4 -butylphenyl)amino]-5,8 -dihydroxy-9,10 -dihydroanthracene-9,10 -dione can be expected to be not readily biodegradable in nature.