1,1'-(4-chlorobutylidene)bis[4-fluorobenzene]

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:

Prediction was done using OECD QSAR tool box v.3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material :1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene
- Molecular formula): C16H15ClF2
- Molecular weight : 280.743 g/mol
- Smiles notation : c1(C(c2ccc(cc2)F)CCCCl)ccc(cc1)F
- InChl: 1S/C16H15ClF2/c17-11-1-2-16(12-3-7-14(18)8-4-12)13-5-9-15(19)10-6-13/h3-10,16H,1-2,11H2
- 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:

0.2

Sampling time:

28 d

Remarks on result:

other: other details not available

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 5 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Alkyl chloride OR Alkyl halide OR Aromatic compound OR Aryl fluoride OR Aryl halide OR Halogen derivative by Organic functional groups, Norbert Haider (checkmol) ONLY

Domain logical expression index: "b"

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

Domain logical expression index: "c"

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 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds OR AN2 >> Nucleophilic addition to alpha, beta-unsaturated carbonyl compounds >> alpha, beta-Unsaturated Aldehydes OR AN2 >> Schiff base formation OR AN2 >> Schiff base formation >> alpha, beta-Unsaturated Aldehydes OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation OR AN2 >> Schiff base formation by aldehyde formed after metabolic activation >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Geminal Polyhaloalkane Derivatives OR AN2 >> Shiff base formation for aldehydes >> Haloalkane Derivatives with Labile Halogen OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical OR Radical >> Generation of ROS by glutathione depletion (indirect) OR Radical >> Generation of ROS by glutathione depletion (indirect) >> Haloalkanes Containing Heteroatom OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Geminal Polyhaloalkane Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR SN1 OR SN1 >> Alkylation after metabolically formed carbenium ion species OR SN1 >> Alkylation after metabolically formed carbenium ion species >> Polycyclic Aromatic Hydrocarbon Derivatives OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> N-Nitroso Compounds 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 involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Geminal Polyhaloalkane Derivatives OR SN2 >> Acylation involving a leaving group  >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Acylation involving a leaving group after metabolic activation OR SN2 >> Acylation involving a leaving group after metabolic activation >> Geminal Polyhaloalkane Derivatives OR SN2 >> Alkylation, direct acting epoxides and related OR SN2 >> Alkylation, direct acting epoxides and related >> Epoxides and Aziridines OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation OR SN2 >> Alkylation, direct acting epoxides and related after P450-mediated metabolic activation >> Polycyclic Aromatic Hydrocarbon Derivatives OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline Derivatives OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Vicinal Dihaloalkanes OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) >> Vicinal Dihaloalkanes OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Haloalkanes Containing Heteroatom OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation OR SN2 >> Nucleophilic substitution at sp3 carbon atom after thiol (glutathione) conjugation >> Geminal Polyhaloalkane Derivatives OR SN2 >> SN2 at an activated carbon atom OR SN2 >> SN2 at an activated carbon atom >> Quinoline Derivatives by DNA binding by OASIS v.1.3

Domain logical expression index: "d"

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

Domain logical expression index: "e"

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

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 6) ONLY

Domain logical expression index: "g"

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

Domain logical expression index: "h"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 216 Da

Domain logical expression index: "i"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 295 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene (CAS no.3312 -04 -7) showed 0.20 % biodegradation in 28 days by BOD parameter and microorganisms as inoculum. This percent biodegradation value is very less so it is concluded that this test chemical is not readily biodegradable.

Executive summary:

Biodegradability of test chemical is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. The test chemical 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene (CAS no.3312 -04 -7) showed 0.20 % biodegradation in 28 days by BOD parameter and microorganisms as inoculum. This percent biodegradation value is very less so it is concluded that this test chemical is not readily biodegradable.

Description of key information

Biodegradability of test chemical is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. The test chemical 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene (CAS no.3312 -04 -7) showed 0.20 % biodegradation in 28 days by BOD parameter and microorganisms as inoculum. This percent biodegradation value is very less so it is concluded that this test chemical is not readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Predicted data for target compound1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene (CAS no.3312 -04 -7) and supporting weight of evidence studies for its closest read across chemicals with log Kow as a primary descriptor were reviewed for the biodegradation endpoint which are summarized as below.

Biodegradability of test chemical is predicted using OECD QSAR tool box v.3.3 using log Kow as primary descriptor. The test chemical 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene (CAS no.3312 -04 -7) showed 0.20 % biodegradation in 28 days by BOD parameter and microorganisms as inoculum. This percent biodegradation value is very less so it is concluded that this test chemical is not readily biodegradable.

 

 In another prediction done by using Estimation Programs Interface Suite (EPI suite, 2017) BIOWIN v4.10. The biodegradation potential of the test chemical   1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene (CAS no. 3312 -04 -7) in the presence of mixed populations of environmental microorganisms. 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-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzeneis expected to be not readily biodegradable.

 

 In the supporting weight of evidence study from authoritative database ( j check 2017). The read across chemical 6-chloro-2-N-ethyl-4-N-(propan-2-yl)-1,3,5-triazine-2,4-diamine ( 1912-24-9) was subjected to biodegradation test by taking activated sludge as a inoculums at 30 mg/L concentration . Biodegradation was analysed by using two parameters BOD and HPLC. The initial concentration of test chemical was 100 mg/L and study design is of standard type. After 4 weeks( 28 days) chemical 6-chloro-2-N-ethyl-4-N-(propan-2-yl)-1,3,5-triazine-2,4-diamine showed 1% biodegradation by BOD and HPLC parameters. So it is concluded that the read across chemical 6-chloro-2-N-ethyl-4-N-(propan-2-yl)-1,3,5-triazine-2,4-diamine is not readily biodegradable.

 

In another supporting weight of evidence study from same source as stated above biodegradation experiment was carried out for read across chemical (chlorodiphenylmethyl)benzene ( CAS no. 76-83-5) by taking sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD and HPLC parameter. The initial concentration of test chemical was 100 mg/L and study design is of standard type. After 4 weeks (28 days) test chemical showed 0% biodegradation by BOD and HPLC. So it is concluded that read across chemical (chlorodiphenylmethyl)benzene is not readily biodegradable.

 

All the studies stated above showed same results i.e., test chemical is not readily biodegradable. Therefore on the basis of above results for target chemical1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene (CAS no.3312 -04 -7) from ( EPI suite 2017 and OECD QSAR tool box v3.3 2017) and for its read across substances ( from authoritative database) it is concluded that the target chemical1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene is be expected to be not readily biodegradable.