Bis(p-aminophenyl)-4-methylenecyclohexa-2,5-dienylideneammonium acetate

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:

Data is from OECD QSAR toolbox version.3.3 and 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 biodegradation test was carried out for 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate according to the OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)).

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material (IUPAC name): Bis(p-aminophenyl)-4-methylenecyclohexa-2,5-dienylideneammonium acetate
- Common name: Bis(p-aminophenyl)-4-methylenecyclohexa-2,5-dienylideneammonium acetate
- Molecular formula: C21H21N3O2
- Molecular weight: 347.416 g/mol
- Smiles notation: N=C1C=C\C(C=C1)=C(\c1ccc(N)cc1)c1ccc(N)cc1.C(C)(=O)O
- InChl: 1S/C19H17N3.C2H4O2/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15;1-2(3)4/h1-12,20H,21-22H2;1H3,(H,3,4)
- Substance type: Organic
-Physical state: solid

Oxygen conditions:

aerobic

Inoculum or test system:

other: micro-organisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

0.4

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Anilines (Acute toxicity) AND Dianilines by US-EPA New Chemical Categories

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 >> Primary aromatic amine by DNA binding by OECD

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Strong binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Michael Addition AND Michael Addition >> Quinoide type compounds AND Michael Addition >> Quinoide type compounds >> Quinone methide(s)/imines; Quinoide oxime structure; Nitroquinones, Naphthoquinone(s)/imines  by Protein binding by OASIS v1.3

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Anilines (Unhindered) by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "f"

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

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >>  Michael-type addition, quinoid structures OR AN2 >>  Michael-type addition, quinoid structures >> Quinoneimines OR AN2 >>  Michael-type addition, quinoid structures >> Quinones OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines OR Non-covalent interaction >> DNA intercalation >> Quinones OR Non-specific OR Non-specific >> Incorporation into DNA/RNA, due to structural analogy with  nucleoside bases    OR Non-specific >> Incorporation into DNA/RNA, due to structural analogy with  nucleoside bases    >> Specific Imine and Thione Derivatives OR Radical OR Radical >> Generation of reactive oxygen species OR Radical >> Generation of reactive oxygen species >> Thiols OR Radical >> Radical mechanism by ROS formation OR Radical >> Radical mechanism by ROS formation >> Polynitroarenes 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) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroaniline Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitroarenes with Other Active Groups OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR Radical >> Radical mechanism via ROS formation (indirect) >> p-Aminobiphenyl Analogs OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Specific Imine and Thione Derivatives OR Radical >> ROS formation after GSH depletion (indirect) OR Radical >> ROS formation after GSH depletion (indirect) >> Quinoneimines OR SN1 OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation OR SN1 >> Nucleophilic attack after diazonium or carbenium ion formation >> Nitroarenes with Other Active Groups 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 >> Fused-Ring Primary Aromatic Amines OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> p-Aminobiphenyl Analogs OR SN1 >> Nucleophilic attack after metabolic nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroaniline Derivatives OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitroarenes with Other Active Groups OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitrophenols, Nitrophenyl Ethers and Nitrobenzoic Acids OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Polynitroarenes OR SN1 >> Nucleophilic substitution on diazonium ions OR SN1 >> Nucleophilic substitution on diazonium ions >> Specific Imine and Thione Derivatives OR SN2 OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 OR SN2 >> SN2 attack on activated carbon Csp3 or Csp2 >> Nitroarenes with Other Active Groups by DNA binding by OASIS v.1.3

Domain logical expression index: "h"

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

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Not calculated by Hydrolysis half-life (pH 6.5-7.4) ONLY

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as Non-Metals by Groups of elements

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Alkali Earth OR Halogens by Groups of elements

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Class 5 (Not possible to classify according to these rules) by Acute aquatic toxicity classification by Verhaar (Modified) ONLY

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 172 Da

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 371 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The test chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was predicted to be not readily biodegradable in water.

Executive summary:

Biodegradability of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS no. 6035-94-5) is predicted using OECD QSAR toolbox version 3.3 with log Kow as the primary descriptor. Test substance undergoes 0.40 % degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS no. 6035-94-5) is predicted using OECD QSAR toolbox version 3.3 with log Kow as the primary descriptor. Test substance undergoes 0.40 % degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate 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

Following different studies includes predicted data and experimental study for the target chemical and the structurally similar read across to conclude the biodegradation in water of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) in environment.

 

Biodegradability of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS no. 6035-94-5) is predicted using OECD QSAR toolbox version 3.3 with log Kow as the primary descriptor. Test substance undergoes 0.40 % degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was estimated to be not readily biodegradable in water.

 

Similar estimated data from Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS no. 6035 -94 -5) 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 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate is expected to be not readily biodegradable.

 

The predicted data is supported by the experimental study of structurally similar read across 2, 2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid) ( CAS no. 81-11-8) from the J-check indicates that The test chemical 2, 2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid) ( CAS no. 81-11-8) was subjected to biodegradation test by taking 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) test chemical showed 0% and 2 % biodegradation by BOD and HPLC parameters respectively so it is concluded that it is not readily biodegradable

 

Further it is supported by the experimental study for the structurally similar read across 3,3'-Sulphonyldianiline ( CAS no. 599 -61 -1) from the

J-check indicates that

The test chemical 3,3'-Sulphonyldianiline ( CAS no. 599 -61 -1) was subjected to biodegradation test by taking sludge as a inoculums at 30 mg/L concentration . Biodegradation was analysed by using three parameters BOD,TOC and HPLC. 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%, 0% and 1 % biodegradation by BOD, TOC and HPLC parameters respectively so it is concluded that it is not readily biodegradable

 

On the basis of above results for target chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) (from EPI suite) and for its read across chemical (from J-CHeck 2017) it can be concluded that the chemical

Following different studies includes predicted data and experimental study for the target chemical and the structurally similar read across to conclude the biodegradation in water of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) in environment.

 

Biodegradability of 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS no. 6035-94-5) is predicted using OECD QSAR toolbox version 3.3 with log Kow as the primary descriptor. Test substance undergoes 0.40 % degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate was estimated to be not readily biodegradable in water.

 

Similar estimated data from Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS no. 6035 -94 -5) 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 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate is expected to be not readily biodegradable.

 

The predicted data is supported by the experimental study of structurally similar read across 2, 2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid) ( CAS no. 81-11-8) from the J-check indicates that The test chemical 2, 2'-ethene-1,2-diylbis(5-aminobenzenesulfonic acid) ( CAS no. 81-11-8) was subjected to biodegradation test by taking 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) test chemical showed 0% and 2 % biodegradation by BOD and HPLC parameters respectively so it is concluded that it is not readily biodegradable

 

Further it is supported by the experimental study for the structurally similar read across 3,3'-Sulphonyldianiline ( CAS no. 599 -61 -1) from the

J-check indicates that

The test chemical 3,3'-Sulphonyldianiline ( CAS no. 599 -61 -1) was subjected to biodegradation test by taking sludge as a inoculums at 30 mg/L concentration . Biodegradation was analysed by using three parameters BOD,TOC and HPLC. 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%, 0% and 1 % biodegradation by BOD, TOC and HPLC parameters respectively so it is concluded that it is not readily biodegradable

 

On the basis of above results for target chemical 4-amino-N-(4-aminophenyl)-N-(4-methylenecyclohexa-2,5-dien-1-ylidene)anilinium acetate (CAS No. 6035-94-5) (from EPI suite) and for its read across chemical (from J-CHeck 2017) it can be concluded that the chemical 4-a