N-(2-phenoxyphenyl)methanesulphonamide

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:

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 (as cited in study report): N-(2-phenoxyphenyl)methanesulfonamide
- Molecular formula (if other than submission substance): C13H13NO3S
- Molecular weight (if other than submission substance): 263.316 g/mol
- Smiles notation (if other than submission substance): S(Nc1c(Oc2ccccc2)cccc1)(=O)(=O)C
- InChI: 1S/C13H13NO3S/c1-18(15,16)14-12-9-5-6-10-13(12)17-11-7-3-2-4-8-11/h2-10,14H,1H3
- 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:

15.6

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 15.6% 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 5 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

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

Domain logical expression index: "b"

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

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Aliphatic Carbon [CH] AND Aliphatic Carbon [-CH2-] AND Aliphatic Carbon [-CH3] AND Aliphatic Nitrogen, one aromatic attach [-N] AND Aliphatic Oxygen, two aromatic attach [-O-] AND Aromatic Carbon [C] AND Miscellaneous sulfide (=S) or oxide (=O) AND Olefinic carbon [=CH- or =C<] AND Oxygen, two olefinic attach [-O-] AND Suflur {v+4} or {v+6} AND Sulfamide, aliphatic attach [-SO2-N] AND Sulfonyl amide, aliphatic attach [-S(=O)N-] AND Sulfur, nitrogen attach [-S-] by Organic functional groups (US EPA)

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 Aliphatic Nitrogen, one aromatic attach [-N] AND Aliphatic Oxygen, two aromatic attach [-O-] AND Aromatic Carbon [C] AND Miscellaneous sulfide (=S) or oxide (=O) AND Olefinic carbon [=CH- or =C<] AND Oxygen, two olefinic attach [-O-] AND Suflur {v+4} or {v+6} AND Sulfamide, aliphatic attach [-SO2-N] AND Sulfonyl amide, aliphatic attach [-S(=O)N-] AND Sulfur, nitrogen attach [-S-] by Organic functional groups (US EPA)

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Aliphatic Carbon [CH] OR Aliphatic Carbon [-CH2-] OR Aliphatic Carbon [-CH3] OR Aliphatic Nitrogen, one aromatic attach [-N] OR Aliphatic Oxygen, two aromatic attach [-O-] OR Aromatic Carbon [C] OR Miscellaneous sulfide (=S) or oxide (=O) OR Olefinic carbon [=CH- or =C<] OR Oxygen, two olefinic attach [-O-] OR Suflur {v+4} or {v+6} OR Sulfamide, aliphatic attach [-SO2-N] OR Sulfonyl amide, aliphatic attach [-S(=O)N-] OR Sulfur, nitrogen attach [-S-] by Organic functional groups (US EPA) ONLY

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Aromatic compound OR Diarylether OR Ether OR Sulfonic acid derivative by Organic functional groups, Norbert Haider (checkmol) ONLY

Domain logical expression index: "g"

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

Domain logical expression index: "h"

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 Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Fused-Ring Primary Aromatic Amines 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) >> Fused-Ring Primary Aromatic Amines OR Radical >> Radical mechanism via ROS formation (indirect) >> Hydrazine Derivatives 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 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 metabolic nitrenium ion formation 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 nitrenium and/or carbenium ion formation OR SN1 >> Nucleophilic attack after nitrenium and/or carbenium ion formation >> N-Nitroso Compounds OR SN2 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 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Quinoline 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: "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 Acylation OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Formamides OR 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 >> Arenes OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Polycyclic (PAHs) and heterocyclic (HACs) aromatic hydrocarbons-Michael addition OR SN1 OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine by DNA binding by OECD

Domain logical expression index: "k"

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

Domain logical expression index: "l"

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

Domain logical expression index: "m"

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

Domain logical expression index: "n"

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

Domain logical expression index: "o"

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

Domain logical expression index: "p"

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

Domain logical expression index: "q"

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

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 178 Da

Domain logical expression index: "s"

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 N-(2-phenoxyphenyl)methanesulfonamide was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of N-(2-phenoxyphenyl)methanesulfonamide is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor (2017). Test substance undergoes 15.6% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical N-(2 -phenoxyphenyl)methane sulfonamide was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of N-(2-phenoxyphenyl)methanesulfonamide is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor (2017). Test substance undergoes 15.6% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical N-(2 -phenoxyphenyl)methane sulfonamide 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

Predicted data for the target compound N-(2-phenoxyphenyl)methanesulfonamide (CAS No. 51765-51-6) and various study for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

For target chemical N-(2-phenoxyphenyl)methanesulfonamide(CAS No. 51765-51-6), biodegradability is predicted using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor (2017). Test substance undergoes 15.6% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical N-(2 -phenoxyphenyl)methane sulfonamide was estimated to be not readily biodegradable in water.

 

Estimation Programs Interface Suite (EPI suite, 2017) was run to predict the biodegradation potential of the test compound N-(2-phenoxyphenyl)methanesulfonamide (CAS no. 51765 -51 -6) 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 N-(2 -phenoxyphenyl)methanesulfonamide is expected to be not readily biodegradable.

 

In a weight of evidence study from authoritative database (J-CHECK, 2016), experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1-methyl-3-phenoxybenzene (CAS no. 3586-14-9). 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 2% and 1% by BOD and GC parameter in 28 days. Thus, based on percentage degradation, 1 -methyl-3 -phenoxybenzene is considered to be not readily biodegradable in nature.

 

For another read across chemical N-butylbenzenesulfonamide (CAS no. 3622 -84 -2), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of test substance. 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% by BOD, HPLC and TOC removal parameter in 28 days. Thus, based on percentage degradation, N-butylbenzenesulfonamide is considered to be not readily biodegradable in nature.

 

Another biodegradation study for the same read across substance N-butylbenzenesulfonamide (CAS no. 3622-84-2) was conducted for 28 days for evaluating the percentage biodegradability of substance (U.S. Environmental Protection Agency, 2016).The study was performed according to OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test) at a temperature of20-23°C.Initial test substance conc. used in the study was 45 and 45.2 mg/l (mg CO2/l) & 21.8 and 21.75 mg/l (based on test mat.), respectively. Activated sludge was used as a test inoculum obtained fromsewage treatment plant. Concentrated sludge (6.5 g solids/L) was left to settle for 30 min; the decanted liquid was used as inoculum (7.65 ml/L mineral medium).Sampling was carried out on day 1, 4, 6, 8, 11, 14, 18, 22, 26 and 28, respectively. Sodium acetate of conc. 40.2 mg/l was used as a reference substance for the study. Reference substance undergoes percentage degradation of 105% after 28 days. The percentage degradation of read across substance was determined to be 12% and 23% byCO2 evolution in 28 days. Thus, based on percentage degradation, N-butylbenzenesulfonamide is considered to be not readily biodegradable in nature.

 

For the same read across chemical N-butylbenzenesulfonamide (CAS no. 3622-84-2) from secondary source (High Production Volume Challenge Program, 2016), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability. The study was performed according to OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test). Initial test substance conc. used in the study was 21.5 mg/l. Activated sludge was used as a test inoculum. In the toxicity control more than 25% degradation occurred within 14 days (based on ThCO2). Therefore, the test substance was assumed to be not inhibitory. The percentage degradation of read across substance was determined to be18% byCO2 evolution parameter in 28 days. Thus, based on percentage degradation, N-butylbenzenesulfonamide is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical N-(2-phenoxyphenyl)methanesulfonamide (fromOECD QSAR toolbox version 3.3 and EPI Suite, 2017) and for its read across substance (from authoritative database J-CHECK, 2016 and secondary source High Production Volume Challenge Program, 2016), it can be concluded that the test substance N-(2-phenoxyphenyl)methanesulfonamide can be expected to be not readily biodegradable in nature.