N-(phenylsulphonyl)benzenesulphonamide

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 data is predicted using the OECD QSAR toolbox version 3.4 with logKow as the primary descriptor.

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material (IUPAC name): N-(benzenesulfonyl)benzenesulfonamide
- Common name: N-(phenylsulphonyl)benzenesulphonamide
- Molecular formula : C12H11NO4S2
- Molecular weight : 297.354 g/mol
- Smiles notation :
O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1
- InChl : 1S/C12H11NO4S2/c14-18(15,11-7-3-1-4-8-11)13-19(16,17)12-9-5-2-6-10-12/h1-10,13H
- Substance type: Organic
- Physical state: Solid

Oxygen conditions:

aerobic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Based on:

not specified

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: BOD

Value:

0.833

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 0.83% 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" )  and "d" )  and "e" )  and "f" )  and "g" )  and ("h" and ( not "i") )  )  and ("j" and ( not "k") )  )  and "l" )  and ("m" and ( not "n") )  )  and ("o" and "p" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group AND Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group >> Arenesulfonamides AND AN2 AND AN2 >> Nucleophilic addition at polarized N-functional double bond AND AN2 >> Nucleophilic addition at polarized N-functional double bond >> Arenesulfonamides by Protein binding by OASIS v1.4

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group AND Acylation >> Acylation involving an activated (glucuronidated) sulfonamide group >> Arenesulfonamides AND AN2 AND AN2 >> Nucleophilic addition at polarized N-functional double bond AND AN2 >> Nucleophilic addition at polarized N-functional double bond >> Arenesulfonamides by Protein binding by OASIS v1.4

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Amides by Aquatic toxicity classification by ECOSAR

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg primary (Biowin 4) 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 weeks - months by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OASIS v.1.4

Domain logical expression index: "i"

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 and Trihydroxybenzenes OR AN2 >> Nucleophilic addition reaction with cycloisomerization OR AN2 >> Nucleophilic addition reaction with cycloisomerization >> Hydrazine Derivatives OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Amino Anthraquinones OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide and Aminoalkylamine Side Chain OR Non-covalent interaction >> DNA intercalation >> Quinones and Trihydroxybenzenes OR Radical 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) >> Hydrazine Derivatives OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones and Trihydroxybenzenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines OR SN1 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 nitrenium ion formation OR SN1 >> Nucleophilic attack after nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines OR SN2 OR SN2 >> Direct nucleophilic attack on diazonium cation OR SN2 >> Direct nucleophilic attack on diazonium cation >> Hydrazine Derivatives by DNA binding by OASIS v.1.4

Domain logical expression index: "j"

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

Domain logical expression index: "k"

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 >> Arenes OR SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation OR SN1 >> Nitrenium Ion formation >> Aromatic nitro by DNA binding by OECD

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Reactive unspecified by Acute aquatic toxicity MOA by OASIS ONLY

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Aromatic-H AND Benzene AND Unsubstituted phenyl group (C6H5-) by Bioaccumulation - metabolism alerts

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as -CH2-  [linear] by Bioaccumulation - metabolism alerts

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 157 Da

Domain logical expression index: "p"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 323 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical N-(benzenesulfonyl)benzenesulfonamide was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of N-(benzenesulfonyl)benzenesulfonamide (CAS no. 2618 -96 -4) is predicted using QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 0.83% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical N-(benzenesulfonyl)benzenesulfonamide was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of N-(benzenesulfonyl)benzenesulfonamide (CAS no. 2618 -96 -4) is predicted using QSAR toolbox version 3.4 (2017) with logKow as the primary descriptor. Test substance undergoes 0.83% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical N-(benzenesulfonyl)benzenesulfonamide 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 N-(benzenesulfonyl)benzenesulfonamide (CAS No. 2618-96-4) 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 a prediction done by SSS (2017) using OECD QSAR toolbox version 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemical N-(benzenesulfonyl)benzene sulfonamide(CAS No. 2618 -96 -4) was estimated.Test substance undergoes 0.83% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical N-(benzene sulfonyl)benzenesulfonamidewas 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 compoundN-(benzenesulfonyl)benzenesulfonamide(CAS No. 2618-96-4) 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 chemicalN-(benzenesulfonyl)benzenesulfonamideis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017 and EnviChem, 2014) for the read across chemical 3 -nitro-N-phenyl-4 -(phenylamino)benzene-1 -sulfonamide (CAS no. 5124 -25 -4), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 3-nitro-N-phenyl-4-(phenylamino)benzene-1-sulfonamide. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). 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 substance 3 -nitro-N-phenyl-4 -(phenylamino)benzene-1 -sulfonamide was determined to be 0 and 5% by BOD and UV-Vis parameter in 28 days. Thus, based on percentage degradation, 3 -nitro-N-phenyl-4 -(phenylamino)benzene-1 -sulfonamide is considered to be not readily biodegradable in nature.

 

For the read across chemical N-Butyl-benzenesulfonamide (CAS no. 3622-84-2), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance N-Butyl-benzenesulfonamide (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 substance N-Butyl-benzenesulfonamide was determined to be 0 and 1% by BOD, TOC removal and HPLC parameter in 28 days. Thus, based on percentage degradation, N-Butyl-benzenesulfonamide is considered to be not readily biodegradable in nature.

 

Another biodegradation study from secondary source (HPVIS, 2017) was conducted for 28 days for evaluating the percentage biodegradability of read across substance N-Butyl-benzene sulfonamide (CAS no. 3622 -84 -2). The study was performed according to OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test).Activated sludge was used as a test inoculum obtained from sewage treatment plant, Netherlands. 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). Initial test substance conc. used for the study were21.75 & 21.8 mg/l based on test material and 45.0 & 45.2 mg/l based on CO2 mg/l, respectively. OECD mineral medium was used as a test medium for the study. Study was performed using brown glass bottles of 2l volume at a temperature of 20-23°C. Sampling was done on day 1, 4, 6, 8, 11, 14, 18, 22, 26 and 28, respectively. Sodium acetate (40.2 mg/l) was used as a reference substance for the study. 10-day window criteria was not reached. ThCO2 was determined to be 2.07 mg CO2/mg test substance. The percentage degradation of substance N-Butyl-benzenesulfonamide was determined to be 12 and 23% at 21.8 and 21.75 mg/l conc. by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, N-Butyl-benzenesulfonamide is considered to be not readily biodegradable in nature.

 

In a supporting weight of evidence study for the same read across chemical N-Butyl-benzenesulfonamide (CAS no. 3622-84-2),biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance N-Butyl-benzenesulfonamide (HPVIS, 2017). The study was performed according to OECD Guideline 301 B (Ready Biodegradability: CO2 Evolution Test). Activated sludge was used as a test inoculum. Initial test substance conc. used for the study was21.5 mg/l, respectively. The percentage degradation of substance N-Butyl-benzenesulfonamide was determined to be 18% by CO2 evolution parameter in 28 days. Thus, based on percentage degradation, N-Butyl-benzenesulfonamide is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemicalN-(benzenesulfonyl)benzenesulfonamide(from OECD QSAR toolbox version 3.4 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK & EnviChem and secondary source HPVIS), it can be concluded that the test substanceN-(benzenesulfonyl)benzenesulfonamidecan be expected to be not readily biodegradable in nature.