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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
Qualifier:
equivalent or similar 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-(3-chlorophenyl)-4-(3-chloropropyl)piperazine
- Molecular formula :C13H18Cl2N2
- Molecular weight :273.205 g/mol
- Smiles notation : N1(c2cc(Cl)ccc2)CCN(CC1)CCCCl
- InChl : 1S/C13H18Cl2N2/c14-5-2-6-16-7-9-17(10-8-16)13-4-1-3-12(15)11-13/h1,3-4,11H,2,5-10H2
- Substance type:Organic
- Physical state:Solid
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:
0.767
Sampling time:
28 d
Remarks on result:
other: Other details not known
Details on results:
Test substance undergoes 0.76% 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 6 nearest neighbours
Domain  logical expression:Result: In Domain

(((((("a" or "b" or "c" or "d" )  and "e" )  and "f" )  and ("g" and ( not "h") )  )  and "i" )  and ("j" and "k" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Aliphatic Amines by US-EPA New Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine OR SN2 OR SN2 >> SN2 at an sp3 Carbon atom OR SN2 >> SN2 at an sp3 Carbon atom >> Aliphatic halides by DNA binding by OECD ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as SN2 OR SN2 >> Nucleophilic substitution at sp3 carbon atom OR SN2 >> Nucleophilic substitution at sp3 carbon atom >> Alkyl halides  by Protein binding by OASIS v1.3 ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as SN2 OR SN2 >> SN2 reaction at sp3 carbon atom OR SN2 >> SN2 reaction at sp3 carbon atom >> Alkyl halides by Protein binding by OECD ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as weeks - months 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 7) ONLY

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Non binder, without OH or NH2 group by Estrogen Receptor Binding

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Non binder, MW>500 OR Non binder, non cyclic structure by Estrogen Receptor Binding

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Bioavailable by Lipinski Rule Oasis ONLY

Domain logical expression index: "j"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 254 Da

Domain logical expression index: "k"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 479 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
not readily biodegradable
Conclusions:
The test chemical 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine was estimated to be not readily biodegradable in water.
Executive summary:

Biodegradability of 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine (CAS no. 39577 -43 -0) is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor (2017). Test substance undergoes 0.76% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1 -(3 -chlorophenyl)-4 -(3 -chloropropyl)piperazine was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine (CAS no. 39577 -43 -0) is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor (2017). Test substance undergoes 0.76% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1 -(3 -chlorophenyl)-4 -(3 -chloropropyl)piperazine 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-(3-chlorophenyl)-4-(3-chloropropyl)piperazine (CAS No. 39577-43-0) and various supporting weight of evidence studies for its read across substances 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 chemical1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine(CAS No. 39577-43-0) was estimated.Test substance undergoes 0.76% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1 -(3 -chlorophenyl)-4 -(3 -chloropropyl)piperazine 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 -(3 -chlorophenyl)-4 -(3 -chloropropyl)piperazine (CAS No. 39577-43-0) 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-(3-chlorophenyl)-4-(3-chloropropyl)piperazine 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 9 -(2 -carboxyphenyl)-3,6 -bis(diethylamino) xanthenium chloride (CAS no. 81 -88 -9), biodegradation in water screening test is conducted for 4 weeks (28 days) for evaluating the biodegradability of read across substance 9 -(2 -carboxyphenyl)-3,6 -bis(diethylamino)xanthenium chloride. Concentration of inoculum i.e, sludge was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of read across substance is determined to be 0, 2 and 7% degradation by BOD, TOC removal and UV-Vis parameter in 28 days. Thus, based on percentage degradation, substance 9 -(2 -carboxyphenyl)-3,6 -bis (diethylamino)xanthenium chloride is considered to be not readily biodegradable in nature.

 

For the another read chemical 4,4'-methylenebis(N,N-dimethylaniline) (CAS no. 101-61-1), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 4,4'-methylenebis(N,N-dimethylaniline) (J-CHECK, 2017). 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 read across substance was determined to be 0 and 1% degradation by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 4,4'-methylenebis(N,N-dimethyl aniline) is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine(CAS No. 39577-43-0)(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 1 -(3 -chlorophenyl)-4 -(3 -chloropropyl)piperazine can be expected to be not readily biodegradable in nature.