2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate

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): 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate
- Molecular formula: C9H13NO7S2
- Molecular weight: 311.3337 g/mol
- Smiles notation: COC1=C(C=CC(=C1)S(=O)(=O)CCOS(=O)(=O)O)N
- InChl: 1S/C9H13NO7S2/c1-16-9-6-7(2-3-8(9)10)18(11,12)5-4-17-19(13,14)15/h2-3,6H,4-5,10H2,1H3,(H,13,14,15)
- 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:

0.125

Sampling time:

28 d

Remarks on result:

other: Other details not known

Details on results:

Test substance undergoes 0.125% 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 8 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

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

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Radical AND Radical >> Radical mechanism via ROS formation (indirect) AND Radical >> Radical mechanism via ROS formation (indirect) >> Single-Ring Substituted Primary Aromatic Amines AND SN1 AND SN1 >> Nucleophilic attack after nitrenium ion formation AND SN1 >> Nucleophilic attack after nitrenium ion formation >> Single-Ring Substituted Primary Aromatic Amines by DNA binding by OASIS v.1.4

Domain logical expression index: "c"

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: "d"

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

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> Substituted Anilines by Protein binding by OASIS v1.4

Domain logical expression index: "f"

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

Domain logical expression index: "g"

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

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "i"

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

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Moderate binder, NH2 group OR Non binder, impaired OH or NH2 group OR Strong binder, OH group OR Weak binder, NH2 group by Estrogen Receptor Binding

Domain logical expression index: "k"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >> Michael-type addition to quinoid structures  AND AN2 >> Michael-type addition to quinoid structures  >> Substituted Anilines by Protein binding by OASIS v1.4

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Schiff base formation OR Schiff base formation >> Schiff base formation with carbonyl compounds OR Schiff base formation >> Schiff base formation with carbonyl compounds >> Aromatic carbonyl compounds by Protein binding by OASIS v1.4

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as High (Class III) by Toxic hazard classification by Cramer (extension) ONLY

Domain logical expression index: "n"

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

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Aromatic amine   [-NH2  or  -NH-] AND Aromatic ether  [-O-aromatic carbon] AND Aromatic-H AND Benzene AND -CH2-  [linear] AND Methyl  [-CH3] by Bioaccumulation - metabolism alerts

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Aromatic chloride   [-CL] by Bioaccumulation - metabolism alerts

Domain logical expression index: "q"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 223 Da

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 415 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate was estimated to be not readily biodegradable in water.

Executive summary:

Biodegradability of 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate (CAS no. 26672 -22 -0) is predicted using QSAR toolbox version 3.4 with logKow as the primary descriptor. Test substance undergoes 0.125% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate was estimated to be not readily biodegradable in water.

Description of key information

Biodegradability of 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate (CAS no. 26672 -22 -0) is predicted using QSAR toolbox version 3.4 (2017) with logKow as the primary descriptor. Test substance undergoes 0.125% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate 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 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate (CAS No. 26672-22-0) and supporting weight of evidence studies for its 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 chemical2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate(CAS No. 26672-22-0) was estimated.Test substance undergoes 0.125% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphatewas 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 compound2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate(CAS No. 26672-22-0) 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 chemical2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphateis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from peer reviewed journal (P. Pitter, 1976) for the read across chemical 5-aminonaphthalene-2-sulfonic acid (CAS no. 119-79-9), a batch test in an open system was conducted for 5 days for evaluating the biodegradability of read across 5-aminonaphthalene-2-sulfonic acid. Adapted activated sludge was used as a test inoculum obtained from a sewage plant is cultivated in a 1000ml volumetric cylinder. The mixture is aerated with pressure air. Every day 200 ml of the mixture is driven off so that the sludge age is 5 days. After driving off the 200ml of the mixture aeration is interrupted, and after sedimentation ca. 600mlof the liquid phase is driven off. The residue (200 ml of the thickened activated sludge) is diluted with tap water to the volume of ca.800 ml and 600 mg/l of starch or glucose, 600 mg/l of peptone, 25 ml of a phosphate buffer pH 7.2, and the solution of the tested compound are added. Then the mixture in the cylinder is made up to 1000ml with tap water and aerated for 23 h (the recirculation ratio is 0-25). After this period the procedure is repeated. Test chemical conc. used for the study was 200 mg/l based on COD. To 1000-1500ml of the biological medium such amount of the solution of the substance tested is added that the initial COD is 200 mg/l. Then such an amount of the adapted activated sludge, washed and thickened by sedimentation, is dosed to the medium that the concentration of the dry matter is 100 mg/l. Simultaneously, a blank test is prepared. The beaker is placed in a dark room with a roughly 3 constant temperature of 20±3°C on an electromagnetic stirrer and a pH of 7.2 for 120 hrs. The initial value of COD or organic carbon of the liquid phase are determined. Samples. filtered or centrifuged before analysis, are taken at suitable intervals. The decrease of the tested substance in the liquid phase is evaluated by determining COD or organic carbon. The results are compared with those of a blank test and standard compound decomposition. With the degree of degradation also the average specific rate of degradation is determined, expressed in terms of mg COD (or organic carbon) removed by a gramme of dry matter of the activated sludge per hour. The percentage degradation of 5-aminonaphthalene-2-sulfonic acid was determined to be 0% degradation by COD parameter in 5 days. Thus, based on percentage degradation, test substance 5 -aminonaphthalene-2 -sulfonic acid was considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance 2-amino-5-methylbenzene sulfonic acid (CAS no. 88-44-8) (authoritative database J-CHECK, 2017 and secondary source OECD SIDS, 2003). The study was performed according to OECD Guide-line 301 C "Ready Biodegradability: Modified MITI Test (I)" under aerobic conditions. Aniline was used as a reference substance for the study. 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. Reference substance undergoes >40% and >60% degradation in 7 and 14 days, respectively. The percentage degradation of substance was determined to be 0 and <0% degradation by BOD, O2 consumption, TOC removal, Test mat. analysis and UV-Vis parameter in 14 days. Thus, based on percentage degradation, 2 -amino-5 -methylbenzene sulfonic acid is considered to be not readily biodegradable in nature.

 

For the read across chemical 4-Amino-1,1’-azobenzene-3,4'-disulfonic acid (CAS no. 101-50-8), biodegradation study of read across substance 4-Amino-1,1’-azobenzene-3,4'-disulfonic acid (acid yellow 9) was performed using 15 different Streptomyces spp. for 14 days (A. Paszcyzynski, et. al; 1991). The test was performed using 15 different Streptomyces spp as an inoculum. The test substance conc. used is 50 mg/l. Each Streptomyces spp. was grown in a cotton-plugged 250 ml flask containing 25 ml of the following medium: 0.2 M Tris buffer (pH 7.6) 100 ml, 1.0g vitamin-free Casamino acids, 100 µg thiamine, 100 µg biotin, 2 g D-glucose, 900 ml deionized water. Thiamine, biotin, and D-glucose were filter sterilized and added to the autoclaved medium. The dye was filter sterilized and added at 0.005% (w/v) to the autoclaved basal medium. Cultures were incubated at 37ᵒC for 14 days with shaking (200 rev min1). Three replicates for each strain grown in only the basal medium were incubated as well. Degradation of test substance was determined by spectrophotometrically and by using HPLC. Degradation of the test substance was confirmed by HPLC. A Hewlett-Packard HP 1090 Liquid Chromatograph equipped with a HP 40 diode array UV-VIS detector and automatic injector was used. The chromatograph was controlled by an HP 9000 series 300 computer which used HP 7995 A ChemStation software. A reverse phase column from Phenomenex (Rancho Palos Verdes, CA, type Spherex 5C 18 size 250 × 2.0 mm, s/no PP/6474A) was used. Each 15-min analysis used a solvent gradient of acetonitrile (solvent A) and 10mM DMS buffer pH 4.5 (solvent B), with the following conditions: 0-5 min, 100% A; 5-12 min, 25% A, 75% B; 12-15 min, 100% B; post time 2 min, injection volume 10µl. Absorption was measured at 250, 325, 350, 400 and 450 nm, and spectra were collected automatically by the peak controller. Spectrophotometric assay was also carried out. A 1 ml sample of actinomycete culture medium was centrifuged and then diluted 2.5 fold with water. Azo dye substrate present was then measured spectrophotometrically (Hewlett-Packard 8452 diode array spectrophotometer operated by PC Vectra computer with HP’s MSTM-DOS/UV-VIS software). The percentage biodegradation of test substance was determined to be 0% i.e; no degradation of test substance was observed by the 15 different Streptomyces spp. Thus, the test substance was considered to be not readily biodegradable in nature.

 

In a supporting weight of evidence study from peer reviewed journal (J. Ruff, et. al; 1999) for the read across chemical 6-aminonaphthalene-1,3-disulfonic acid (CAS no. 118-33-2),biodegradation experiment was conducted for 9 days for evaluating the percentage biodegradability of read across substance 6 -aminonaphthalene-1,3 -disulfonic acid. Test chemical 6 -aminonaphthalene-1,3 -disulfonic acid was purchased from TCI (Tokyo) at the highest purity available. Glassware was cleaned thoroughly and care taken to exclude extraneous sulfur. Pseudomonas putida strain S-313 was used as a test inoculum obtained from activated sludge from sewage treatment plants in Konstanz, Germany (largely communal) and Ludwigshafen, Germany (largely industrial).Initial experiments were done with the phosphate-buffered medium. The sulfur-free acetate-Tris-buffered salts medium gave the same products with negligible background growth, and thus used as a standard medium. Sulfur was provided at 50µM, except for disulfonates, where the initial sulfonate concentration was 30µM.Cultures were grown in screw-capped tubes on a roller at 30°C.Samples were taken at 3-day intervals for 9 days. Bacteria were removed by centrifugation and the protein content measured, and 100µl portions of the supernatant fluid were examined by HPLC. Substrates and products were determined by isocratic reversed-phase high-pressure liquid chromatography (HPLC) or by ion-pair chromatography. The apparatus included a diode array detector. Chromatograms were initially evaluated with wavelength settings of 245 nm for the amino-naphthalenedisulfonates. Protein was assayed by a Lowry-type method.The percentage degradation of test chemical 6 -aminonaphthalene-1,3 -disulfonic acid was determined to be 0% by using Pseudomonas putida strain S-313 as an inoculum. Thus, based on percentage degradation, chemical 6 -aminonaphthalene-1,3 -disulfonic acid can be considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 30 days under aerobic conditions for evaluating the percentage biodegradability of read across substance 6 -aminonaphthalene-1,3 -disulfonic acid (CAS no. 118 -33 -2) (from peer reviewed journal GREIM H., et. al; 1994 and secondary source IUCLID dataset, 2000). The study was performed according to OECD Guideline 301 D "Ready Biodegradability: Closed Bottle Test". Initial test substance conc. used in the study were 3, 10 and 30 mg/l, respectively. The percentage degradation of substance 6 -aminonaphthalene-1,3 -disulfonic acid was determined to be 0% by BOD parameter in 30 days. Thus, based on percentage degradation, 6 -aminonaphthalene-1,3 -disulfonic acid is considered to be not readily biodegradable in nature.

On the basis of above results for target chemical 2-[(4-amino-3-methoxyphenyl)sulphonyl]ethyl hydrogen sulphate (from OECD QSAR toolbox version 3.4 and EPI suite, 2017) and for its read across substance (from peer reviewed journal, authoritative database J-CHECK and secondary source OECD SIDS and IUCLID dataset), it can be concluded that the test substance 5-amino-2-methoxybenzene-1-sulfonic acid can be expected to be not readily biodegradable in nature.