Xanthylium, 9-[2-(ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate

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 (as cited in study report): Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate
- Molecular formula : C28H31N2O3.xUnspecified
- Molecular weight: 443.5639 g/mol
- Smiles notation: CCNc1cc2c(cc1C)c(c3cc(c(cc3[o+]2)NCC)C)c4ccccc4C(=O)OCC
- InChI: 1S/C28H31N2O3/c1-6-29-23-15-25-21(13-17(23)4)27(19-11-9-10-12-20(19)28(31)32-8-3)22-14-18(5)24(30-7-2)16-26(22)33-25/h9-16,29-30H,6-8H2,1-5H3/q+1
- 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: % biodegradability by BOD

Value:

6.167

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

Percent biodegrdation of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate was determined to be 6.16 % 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 5 nearest neighbours
Domain  logical expression:Result: In Domain

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

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Esters (Chronic toxicity) 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 >> Secondary aromatic amine by DNA binding by OECD

Domain logical expression index: "c"

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

Domain logical expression index: "d"

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

Domain logical expression index: "e"

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

Domain logical expression index: "f"

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 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds OR AN2 >> Michael-type addition on alpha, beta-unsaturated carbonyl compounds >> Four- and Five-Membered Lactones OR AN2 >> Schiff base formation OR AN2 >> Schiff base formation >> Polarized Haloalkene Derivatives OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Haloalkenes with Electron-Withdrawing Groups OR AN2 >> Thioacylation via nucleophilic addition after cysteine-mediated thioketene formation >> Polarized Haloalkene Derivatives OR Non-covalent interaction OR Non-covalent interaction >> DNA intercalation OR Non-covalent interaction >> DNA intercalation >> Coumarins OR Non-covalent interaction >> DNA intercalation >> DNA Intercalators with Carboxamide Side Chain OR Non-covalent interaction >> DNA intercalation >> Quinones OR Radical OR Radical >> Generation of reactive oxygen species OR Radical >> Generation of reactive oxygen species >> Thiols OR Radical >> Generation of ROS by glutathione depletion (indirect) OR Radical >> Generation of ROS by glutathione depletion (indirect) >> Haloalkanes Containing Heteroatom OR Radical >> Radical mechanism via ROS formation (indirect) OR Radical >> Radical mechanism via ROS formation (indirect) >> Coumarins OR Radical >> Radical mechanism via ROS formation (indirect) >> Nitro Azoarenes OR Radical >> Radical mechanism via ROS formation (indirect) >> Quinones OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation OR SN1 >> Nucleophilic attack after reduction and nitrenium ion formation >> Nitro Azoarenes OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters 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 >> Haloalkenes with Electron-Withdrawing Groups OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Sulfonates and Sulfates OR SN2 >> Alkylation, ring opening SN2 reaction OR SN2 >> Alkylation, ring opening SN2 reaction >> Four- and Five-Membered Lactones OR SN2 >> Direct acting epoxides formed after metabolic activation OR SN2 >> Direct acting epoxides formed after metabolic activation >> Coumarins OR SN2 >> DNA alkylation OR SN2 >> DNA alkylation >> Alkylphosphates, Alkylthiophosphates and Alkylphosphonates OR SN2 >> DNA alkylation >> Vicinal Dihaloalkanes OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) OR SN2 >> Internal SN2 reaction with aziridinium and/or cyclic sulfonium ion formation (enzymatic) >> Vicinal Dihaloalkanes OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Haloalkanes Containing Heteroatom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters OR SN2 >> Ring opening SN2 reaction OR SN2 >> Ring opening SN2 reaction >> Sultones OR SN2 >> SN2 at sp3 and activated sp2 carbon atom OR SN2 >> SN2 at sp3 and activated sp2 carbon atom >> Polarized Haloalkene Derivatives by DNA binding by OASIS v.1.3

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 Biodegrades Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "i"

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

Domain logical expression index: "j"

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

Domain logical expression index: "k"

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

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as Alkyl arenes AND Aromatic amine AND Aryl AND Carboxylic acid ester AND Overlapping groups AND Xanthene by Organic Functional groups (nested)

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as Benzyl by Organic Functional groups (nested)

Domain logical expression index: "n"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 234 Da

Domain logical expression index: "o"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 453 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

Percent biodegrdation of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate was determined to be 6.16 % by considering BOD as parameter and microrganisms as inoculum in 28 days.

Executive summary:

Biodegradability of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate (CAS no. 12224 -98 -5) was determined by using OECD QSAR tool box v3.3 and five closest red across chemical with log Kow as primary descriptor. Percent biodegrdation of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate was determined to be 6.16 % by considering BOD as parameter  and microrganisms as inoculum in 28 days.

Description of key information

Biodegradability of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate (CAS no. 12224 -98 -5) was determined by using OECD QSAR tool box v3.3 and five closest red across chemical with log Kow as primary descriptor. Percent biodegrdation of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate was determined to be 6.16 % by considering BOD as parameter  and microrganisms as inoculum in 28 days.

Key value for chemical safety assessment

Biodegradation in water:

under test conditions no biodegradation observed

Additional information

Two predicted data study for target chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate (CAS no. 12224-98-5) and Experimental studies for its structurally similar read across chemicals have been conducted and their results are summarized below for biodegradation in water endpoint.

In first weight of evidence study the biodegradability of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate (CAS no. 12224 -98 -5) was determined by using OECD QSAR tool box v3.3 and five closest red across chemical with log Kow as primary descriptor. Percent biodegrdation of test chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate was determined to be 6.16 % by considering BOD as parameter  and microorganisms as inoculums in 28 days.

Another predicted data study was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound Xanthylium, 9 -(2 -(ethoxycarbonyl)phenyl)-3,6 -bis(ethylamino)-2,7 -dimethyl-, molybdatetungstatephosphate (CAS no. 12224 -98 -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 chemical Xanthylium, 9 -(2 -(ethoxycarbonyl)phenyl)-3,6 -bis(ethylamino)-2,7 -dimethyl-, molybdatetungstatephosphate is expected to be not readily biodegradable.

Next weight of evidence study was experimental study done from authoritative database (J Check, 2017) for read across chemical [9-(2-carboxyphenyl)-6-(diethylamino) xanthen-3-ylidene]-diethylazanium; chloride (CAS no. 81-88-9) in this study the read across chemical was subjected to biodegradation test by taking sludge as inoculums at 30 mg/L concentration. Biodegradation was analysed by using BOD, TOC and UV vis parameters. The initial concentration of read across chemical was 100 mg/L. After 4 weeks (28 days)read across chemical [9-(2-carboxyphenyl)-6-(diethylamino)xanthen-3-ylidene]-diethylazanium;chloride showed 0 % biodegradability by BOD parameter 2.0 % biodegradation by TOC parameter and 7 % biodegradation by UV Vis parameter and activated sludge as inoculums in 28 days so it is concluded that read across chemical [9-(2-carboxyphenyl)-6-(diethylamino)xanthen-3-ylidene]-diethylazanium;chloride is not readily biodegradable.

 

Next study was also experimental study done from Science of the Total Environment 533 (2015) 446–453 for structurally similar read across chemical Uranine in this study a combination of two biodegradation tests (Closed Bottle test and Manometric Respiratory test, OECDs 301 D, F) was carried out to investigate the biodegradability of the Uranine.

The Manometric Respiratory tests works with higher bacterial density (5–10×106CFUs/mL) and diversity as the Closed Bottle test thus increasing the probability for biodegradation. This test was performed according to the OECD guidelines (OECD, 1992) in the dark at room temperature (20 ± 1 °C) under gentle stirring. CO2 production as the parameter of the endpoint biodegradation was measured indirectly by the OxiTop OC110-system.

The concentration of standard solution for uranine was 16.7 mg/L, corresponding to the theoretical oxygen demand ThOD of 30 mg/L. Inoculum was derived from the municipal sewage treatment plant (Lüneburg, Germany). Aliquots (measuring) of 80ml of inoculum were added to 1 L of mineral medium. The test consisted of four different series: (i) a blank series (containing only the mineral medium and inoculum), (ii) quality control (containing readily biodegradable sodium acetate as the only relevant carbon source apart from the inoculum), (iii) a test series (containing the target compound) and (iv) toxicity control (containing target compound and sodium acetate as carbon source). The amount of sodium acetate for each series corresponded to ThOD of 5 mg/L. A compound is qualified as “ready biodegradable” when 60% of ThOD expressed as percentage of oxygen consumption is consumed within a period of 10 days after the oxygen uptake reached 10% of ThOD. Samples from the beginning (day 0) and the end of the test (day 28) were collected and stored at −20 °C until analysis with HPLC-FLD and LC–M/MS.

No toxic effects on bacteria were observed in the toxicity control as well as no degradation was observed in the sterile control. The measurements with HPLC-FLD confirmed that no elimination of uranine occurred during the Manometric Respiratory Test. Only 0.1% degradation of read across substance Uranine was observed. The reason for the negative values in Manometric Respiratory test might be interpreted as high degradation in the blank control and should be considered could be due to some background in the blanks and can be considered as 0% degradation of the read across substance.Based on the results obtained in Manometric Respiratory test method, Uranine is expected to be not readily biodegradable.

And Closed Bottle Test was performed according to the guidelines of the Organization for Economic Co-operation and Development OECD 301D. This test is characterized by low bacteria density (102–105 colony forming units (CFUs)/mL), low nutrient content, and constant temperature (20 ± 1 °C) and it was kept in the dark. The average biodegradation value after 28 days for Uranine monitored by measurement of the oxygen concentration was 7.6. Based on the results obtained, Uranine is expected to be not readily biodegradable.

On the basis of all the studies mentioned above for target chemical Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, molybdatetungstatephosphate and experimental studies for its read across chemicals it is concluded that target chemical is expected to be not readily biodegradable.