4-methoxy-N-phenyl-o-toluidine

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:

The prediction was done by using OECD QSAR tool box v3.3

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material: 4-methoxy-2-methyl-N-phenylaniline
- IUPAC name: 4-methoxy-2-methyl-N-phenylaniline
- Molecular formula: C14H15NO
- Molecular weight: 213.279 g/mol
- Smiles: c1(c(cc(cc1)OC)C)Nc1ccccc1
- InChl: 1S/C14H15NO/c1-11-10-13(16-2)8-9-14(11)15-12-6-4-3-5-7-12/h3-10,15H,1-2H3
- Substance type: Organic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: % degradability (BOD)

Value:

0.55

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

Percent degradability of test chemical 4-methoxy-2-methyl-N-phenylaniline was estimated to be 0.550 % by considering BOD as parameter in 28 days.

The prediction was based on dataset comprised from the following descriptors: BOD
Estimation method: Takes average value from the 8 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 ( not "n") )  )  and "o" )  and ("p" and ( not "q") )  )  and ("r" and ( not "s") )  )  and "t" )  and ("u" and "v" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Alkylarylether OR Amine OR Aromatic compound OR Ether OR Secondary amine OR Secondary aromatic amine by Organic functional groups, Norbert Haider (checkmol) ONLY

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Aliphatic Carbon [CH] OR Aliphatic Carbon [-CH2-] OR Aliphatic Carbon [-CH3] OR Aliphatic Nitrogen, two aromatic attach [-N-] OR Aromatic Carbon [C] OR Nitrogen, two or tree olefinic attach [>N-] OR Olefinic carbon [=CH- or =C<] OR Oxygen, one aromatic attach [-O-] by Organic functional groups (US EPA) ONLY

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Alkyl arenes OR Aromatic amine OR Ether OR Overlapping groups OR Precursors quinoid compounds by Organic Functional groups (nested) ONLY

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Alkyl arenes OR Aromatic amine OR Aryl OR Ether OR Precursors quinoid compounds by Organic Functional groups ONLY

Domain logical expression index: "e"

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

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg primary (Biowin 4) 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 Does NOT Biodegrade Fast by Biodeg probability (Biowin 6) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OECD

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Michael addition OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Alkyl phenols OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Arenes OR SN1 OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine OR SN1 >> Nitrosation-SN1 OR SN1 >> Nitrosation-SN1 >> N-Nitroso-SN1 OR SN2 OR SN2 >> Direct Acting Epoxides and related OR SN2 >> Direct Acting Epoxides and related >> Epoxides by DNA binding by OECD

Domain logical expression index: "k"

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

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Non binder, impaired OH or NH2 group OR Non binder, non cyclic structure by Estrogen Receptor Binding

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as No alert found by Protein binding by OASIS v1.3

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Michael Addition OR Michael Addition >> Michael addition on conjugated systems with electron withdrawing group OR Michael Addition >> Michael addition on conjugated systems with electron withdrawing group >> alpha,beta-Carbonyl compounds with polarized double bonds  OR Michael Addition >> Polarised Alkenes OR Michael Addition >> Polarised Alkenes >> Polarised Alkene - alkenyl pyridines, pyrazines, pyrimidines or triazines  by Protein binding by OASIS v1.3

Domain logical expression index: "o"

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

Domain logical expression index: "p"

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

Domain logical expression index: "q"

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

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Group 14 - Carbon C AND Group 15 - Nitrogen N AND Group 16 - Oxygen O by Chemical elements

Domain logical expression index: "s"

Referential boundary: The target chemical should be classified as Group 16 - Sulfur S by Chemical elements

Domain logical expression index: "t"

Referential boundary: The target chemical should be classified as Alkylarylether AND Amine AND Aromatic compound AND Ether AND Secondary amine AND Secondary aromatic amine by Organic functional groups, Norbert Haider (checkmol) ONLY

Domain logical expression index: "u"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 104 Da

Domain logical expression index: "v"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 260 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

Percent degradability of test chemical 4-methoxy-2-methyl-N-phenylaniline was estimated to be 0.550 % by considering BOD as parameter and microorganisms as inoculum in 28 days. On the basis of percent degradability value it is concluded that this test chemical is not readily biodegradable.

Executive summary:

Biodegradability of test chemical 4-methoxy-2-methyl-N-phenylaniline (CAS no. 41317 -15 -1) was estimated by using OECD QSAR tool box v3.3 by considering eight closest read across chemicals with log Kow as primary descriptor. Percent degradability of test chemical 4-methoxy-2-methyl-N-phenylaniline was estimated to be 0.550 % by considering BOD as parameter  and microorganisms as inoculum in 28 days. On the basis of percent degradability value it is concluded that this test chemical is not readily biodegradable.

Description of key information

Biodegradability of test chemical 4-methoxy-2-methyl-N-phenylaniline (CAS no. 41317 -15 -1) was estimated by using OECD QSAR tool box v3.3 by considering eight closest read across chemicals with log Kow as primary descriptor. Percent degradability of test chemical 4-methoxy-2-methyl-N-phenylaniline was estimated to be 0.550 % by considering BOD as parameter  and microorganisms as inoculum in 28 days. On the basis of percent degradability value 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 the target compound 4-methoxy-2-methyl-N-phenylaniline (CAS no. 41317 -15 -1)and supporting weight of evidence studies for its structurally similar read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In first predicted data study the biodegradability of test chemical 4-methoxy-2-methyl-N-phenylaniline (CAS no. 41317 -15 -1) was estimated by using OECD QSAR tool box v3.3 by considering eight closest read across chemicals with log Kow as primary descriptor. Percent degradability of test chemical 4-methoxy-2-methyl-N-phenylaniline was estimated to be 0.550 % by considering BOD as parameter and microorganisms as inoculum in 28 days. On the basis of percent degradability value it is concluded that this test chemical is not readily biodegradable.

 

Next predicted data study was done by using estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound 4-methoxy-2-methyl-N-phenylaniline (CAS no. 41317 -15 -1) 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 Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical 4-methoxy-2-methyl-N-phenylanilineis expected to be not readily biodegradable.

 

Further to support the above studies of target chemical experimental study have been conducted for read across chemical from authoritative database J- CHECK (2017)in this study Biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2-(2-Methylpropoxy) naphthalene. 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 test substance was determined to be 1 and 19% by BOD and HPLC parameters respectively in 28 days. Thus, based on percentage degradation, 2-(2-Methylpropoxy)naphthalene is considered to be not readily biodegradable in nature.

 

One more experimental study have been conducted to support predicted data of target chemical same source as mentioned above (J-CHECK, 2017) in this study read across chemical Benzenamine, N-phenyl- (CAS no.122 -39 -4) was subjected to biodegradation test by taking activated sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using three parameter namely BOD, GC and UV Vis . The initial concentration of read across chemical was 100 mg/L. The read across chemical Benzenamine, N-phenyl- showed 0 % biodegradability by BOD parameter 6.5 % by GC parameter and 5.0 % by UV vis parameter by using activated sludge as inoculumin 14 days. On the basis of percent biodegradability it is concluded that read acros chemical Benzenamine, N-phenyl- is not readily biodegradable.

 

On the basis of results of above mentioned studies for target chemical 4-methoxy-2-methyl-N-phenylaniline (CAS no. 41317 -15 -1) (from OECD QSAR tool box v3.3 and EPI suite) and supporting weight of evidence study (from J Check, 2017). It is concluded that the test chemical 4-methoxy-2-methyl-N-phenylaniline can be expected to be not readily biodegradable.