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Biodegradation in water: screening tests

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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
Reference:
Composition 1
Qualifier:
according to
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 3.4 with logKow as the primary descriptor.
GLP compliance:
not specified
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material: 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione
- Molecular formula: C26H30N2O2
- Molecular weight: 402.535 g/mol
- Smiles notation: O=C1c2c(c(NC3CCCCC3)ccc2)C(=O)c2cccc(NC3CCCCC3)c12
- InChl: 1S/C26H30N2O2/c29-25-20-14-8-16-22(28-18-11-5-2-6-12-18)24(20)26(30)19-13-7-15-21(23(19)25)27-17-9-3-1-4-10-17/h7-8,13-18,27-28H,1-6,9-12H2
- Substance type: Organic
- Physical state: Solid
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:
0.857
Sampling time:
28 d
Remarks on result:
other: Other details not known
Details on results:
Test substance undergoes 0.86% degradation by BOD in 28 days.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 7 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 ( not "l") )  )  and ("m" and "n" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >>  Michael-type addition, quinoid structures AND AN2 >>  Michael-type addition, quinoid structures >> Quinones and Trihydroxybenzenes AND Non-covalent interaction AND Non-covalent interaction >> DNA intercalation AND Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes AND Radical AND Radical >> Radical mechanism via ROS formation (indirect) AND Radical >> Radical mechanism via ROS formation (indirect) >> Quinones and Trihydroxybenzenes by DNA binding by OASIS v.1.4

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Secondary aromatic amine by DNA binding by OECD

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> N-Substituted Aromatic Amines by Protein binding by OASIS v1.4

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Ketones by Skin irritation/corrosion Inclusion rules by BfR

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg primary (Biowin 4) ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "g"

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

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Reactive unspecified by Acute aquatic toxicity MOA by OASIS ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Quinones (Genotox) AND Structural alert for genotoxic carcinogenicity by Carcinogenicity (genotox and nongenotox) alerts by ISS

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Halogenated benzene (Nongenotox) OR Hydrazine (Genotox) OR Nitro-aromatic (Genotox) OR No alert found OR Primary aromatic amine,hydroxyl amine and its derived esters (Genotox) OR Structural alerts for both genotoxic and nongenotoxic carcinogenicity by Carcinogenicity (genotox and nongenotox) alerts by ISS

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as No alert found by Protein binding alerts for Chromosomal aberration by OASIS v.1.2

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >> Michael addition to the quinoid type structures OR AN2 >> Michael addition to the quinoid type structures >> N-Subsituted Aromatic Amines by Protein binding alerts for Chromosomal aberration by OASIS v.1.2

Domain logical expression index: "m"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 227 Da

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 475 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
under test conditions no biodegradation observed
Conclusions:
The test chemical 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.
Executive summary:

Biodegradability of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no. 15958 -68 -6) is predicted using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 0.86% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10-dione was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no. 15958 -68 -6) is predicted using OECD QSAR toolbox version 3.4 (2017) with logKow as the primary descriptor. Test substance undergoes 0.86% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 1,5 -bis(cyclohexyl amino)-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 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) and supporting weight of evidence studies for its closest 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 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemical1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) was estimated.Test substance undergoes 0.86% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1,5 -bis(cyclohexyl amino)-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 compound1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) 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 1,5 -bis(cyclohexyl amino)-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, HSDB, SRC (Syracuse Research Corporation) PhysProp 2017 and Envichem, 2014) for the read across chemical 2-amino-9,10-dihydroanthracene-9,10-dione (CAS no. 117-79-3), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2 -amino-9,10 -dihydroanthracene-9,10 -dione. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)) under aerobic conditions at a temperature of 25°C and pH of 7.0, respectively. 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 -amino-9,10 -dihydroanthracene-9,10 -dione was determined to be 1 and 3% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 2 -amino-9,10 -dihydroanthracene-9,10 -dione is considered to be not readily biodegradable in nature.

 

For the read across chemical 1-hydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 129-43-1), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1-hydroxy-9,10-dihydroanthracene-9,10-dione (J-CHECK, HSDB, SRC (Syracuse Research Corporation) PhysProp database, 2017). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)) under aerobic conditions at a temperature of 25°C and pH of 7.0, respectively. 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 1 -hydroxy-9,10 -dihydroanthracene-9,10 -dione was determined to be 2 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,1 -hydroxy-9,10 -dihydroanthracene-9,10 -dione is considered to be not readily biodegradable in nature.

 

Another biodegradation study from authoritative database (J-CHECK, 2017) and secondary source (OECD SIDS, 1996) was conducted for 28 days for evaluating the percentage biodegradability of read across substance sodium 1-amino-9,10-dihydroanthracene-9,10-dione (CAS no. 82-45-1). The study was performed according to OECD Guideline 301C “Ready biodegradability: Modified MITI Test (I)” under aerobic conditions. 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 1-amino-9,10-dihydroanthracene-9,10-dione was determined to be 0 and 2% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,1-amino-9,10-dihydroanthracene-9,10-dione is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(from OECD QSAR toolbox version 3.4 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB, SRC (Syracuse Research Corporation) PhysProp and secondary source OECD SIDS), it can be concluded that the test substance1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dionecan be expected to be not readily biodegradable in nature.