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Environmental fate & pathways

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
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 (IUPAC name) : (E)-(ethyl N-hydroxyethenecarboximidate)
- Common name : Ethyl N-hydroxyacetimidate, Ethyl Acetohydroximate
- Molecular formula : C4H9NO2
- Molecular weight : 103.12 g/mol
- Smiles notation : C(=N/O)(\OCC)C
- InChl : 1S/C4H9NO2/c1-3-7-4(2)5-6/h6H,3H2,1-2H3
- Substance type : Organic
- Physical state : Liquid
Oxygen conditions:
aerobic
Inoculum or test system:
other: Microorganisms
Duration of test (contact time):
28 d
Parameter followed for biodegradation estimation:
other: BOD
Key result
Parameter:
other: BOD
Value:
5.3
Sampling time:
28 d
Remarks on result:
other: Other details not known
Details on results:
Test substance undergoes 5.3% 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 10 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Aliphatic Amines by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Alkoxy AND Ether by Organic Functional groups

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Alkoxy AND Ether AND Overlapping groups by Organic Functional groups (nested)

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Aliphatic Carbon [CH] AND Aliphatic Carbon [-CH2-] AND Aliphatic Carbon [-CH3] AND Azomethine, aliphatic attach [-N=C] AND Hydroxy, nitrogen attach [-OH] AND Olefinic carbon [=CH- or =C<] AND Oxime, aliphatic attach [-CH=N-OH]  AND Oxygen, nitrogen attach [-O-] by Organic functional groups (US EPA)

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.3

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinones OR AN2 >> Carbamoylation after isocyanate formation OR AN2 >> Carbamoylation after isocyanate formation >> N-Hydroxylamines OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> N-methylol derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Amino Anthraquinones OR Radical >> Radical mechanism via ROS formation (indirect) >> N-Hydroxylamines OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> N-Nitroso Compounds OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Amino Anthraquinones OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> N-Hydroxylamines OR SN1 >> Nucleophilic attack after nitrenium and/or carbenium ion formation OR SN1 >> Nucleophilic attack after nitrenium and/or carbenium ion formation >> N-Nitroso Compounds OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Alkylation, direct acting epoxides and related OR SN2 >> Alkylation, direct acting epoxides and related >> Epoxides and Aziridines OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Alkylphosphates, Alkylthiophosphates and Alkylphosphonates OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters by DNA binding by OASIS v.1.3

Domain logical expression index: "g"

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

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 2) ONLY

Domain logical expression index: "j"

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

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as weeks - months by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Aliphatic Amines by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Alkoxy Silanes OR Carbamate Esters, Phenyl OR Neutral Organics by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as -CH2-  [linear] AND Methyl  [-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Alkyl substituent on aromatic ring by Bioaccumulation - metabolism alerts

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as -CH2-  [linear] AND Methyl  [-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as No alert found by Bioaccumulation - metabolism alerts

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 88.1 Da

Domain logical expression index: "s"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 152 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
not readily biodegradable
Conclusions:
The test chemical (E)-(ethyl N-hydroxyethenecarboximidate) was estimated to be not readily biodegradable in water.
Executive summary:

Biodegradability of (E)-(ethyl N-hydroxyethenecarboximidate) (CAS no. 10576 -12 -2) is predicted using QSAR toolbox version 3.3 with logKow as the primary descriptor. Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical (E)-(ethyl N-hydroxyethenecarboximidate) was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of (E)-(ethyl N-hydroxyethenecarboximidate) (CAS no. 10576 -12 -2) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical (E)-(ethyl N-hydroxyethenecarboximidate) 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 (E)-(ethyl N-hydroxyethenecarboximidate) (CAS No. 10576-12-2) and various supporting weight of evidence studies for its read across substance with logKow as the primary descriptor 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(E)-(ethyl N-hydroxyethene carboximidate) (CAS No. 10576-12-2) was estimated.Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical(E)-(ethyl N-hydroxyethenecarboximidate)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(E)-(ethyl N-hydroxyethenecarboximidate)(CAS No. 10576-12-2) 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(E)-(ethyl N-hydroxyethenecarboximidate)is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical (2-aminoethyl)dimethylamine (CAS no. 108-00-9),biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance (2-aminoethyl)dimethylamine. Activated sludge was used as a test inoculums for the study. 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-aminoethyl)dimethylamine was determined to be 0 and 2% by BOD, TOC removal and HPLC parameter in 28 days. Thus, based on percentage degradation, (2-aminoethyl)dimethylamine is considered to be not readily biodegradable in nature.

 

For the read across chemical (bis(butan-2-yl)amine (CAS no. 626-23-3),biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance (bis(butan-2-yl)amine (J-CHECK, 2017). Activated sludge was used as a test inoculums for the study. 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(butan-2-yl)amine was determined to be 0 and 1% by BOD, TOC removal and GC parameter in 28 days. Thus, based on percentage degradation, (bis(butan-2 -yl)amine is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical (E)-(ethyl N-hydroxyethenecarboximidate) (from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, 2017), it can be concluded that the test substance (E)-(ethyl N-hydroxyethenecarboximidate) can be expected to be not readily biodegradable in nature.