2,2'-[(3-acetamidophenyl)imino]diethyl diacetate

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:

Prediction was done using OECD QSAR tool box v.3.3

GLP compliance:

not specified

Specific details on test material used for the study:

Name of the test chemical: 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate
Molecular Formula: C16H22N2O5
Molecular Weight: 322.359 g/mol
InChI: 1S/C16H22N2O5/c1-12(19)17-15-5-4-6-16(11-15)18(7-9-22-13(2)20)8-10-23-14(3)21/h4-6,11H,7-10H2,1-3H3,(H,17,19)
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:

1.214

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

The test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1) showed 1.21 % biodegradation 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 7 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 ( not "l") )  )  and "m" )  and ("n" and ( not "o") )  )  and ("p" and "q" )  )

Domain logical expression index: "a"

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

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as AN2 AND AN2 >> Shiff base formation after aldehyde release AND AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters AND SN1 AND SN1 >> Nucleophilic attack after carbenium ion formation AND SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters AND SN2 AND SN2 >> Acylation AND SN2 >> Acylation >> Specific Acetate Esters AND SN2 >> Nucleophilic substitution at sp3 Carbon atom AND SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters by DNA binding by OASIS v.1.3

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 >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "d"

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

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Ester aminolysis AND Acylation >> Ester aminolysis >> Amides by Protein binding by OASIS v1.3

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Acylation AND Acylation >> Direct Acylation Involving a Leaving group AND Acylation >> Direct Acylation Involving a Leaving group >> Acetates by Protein binding by OECD

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as SN1 AND SN1 >> Nitrenium Ion formation AND SN1 >> Nitrenium Ion formation >> Tertiary aromatic amine by DNA binding by OECD

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Acylation OR Acylation >> Direct Addition of an Acyl Halide OR Acylation >> Direct Addition of an Acyl Halide >> Acyl halide OR Acylation >> Isocyanates and Isothiocyanates OR Acylation >> Isocyanates and Isothiocyanates >> Isocyanates OR Acylation >> P450 Mediated Activation to Acyl Halides OR Acylation >> P450 Mediated Activation to Acyl Halides >> 1,1-Dihaloalkanes OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates OR Acylation >> P450 Mediated Activation to Isocyanates or Isothiocyanates >> Benzylamines-Acylation OR Michael addition OR Michael addition >> P450 Mediated Activation of Heterocyclic Ring Systems OR Michael addition >> P450 Mediated Activation of Heterocyclic Ring Systems >> Furans OR Michael addition >> P450 Mediated Activation of Heterocyclic Ring Systems >> Thiophenes-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 >> Hydroquinones OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Methylenedioxyphenyl OR Michael addition >> P450 Mediated Activation to Quinones and Quinone-type Chemicals >> Polycyclic (PAHs) and heterocyclic (HACs) aromatic hydrocarbons-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated amides OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated esters OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated ketones OR Michael addition >> Quinones and Quinone-type Chemicals OR Michael addition >> Quinones and Quinone-type Chemicals >> Quinones OR No alert found OR Schiff base formers OR Schiff base formers >> Chemicals Activated by P450 to Glyoxal  OR Schiff base formers >> Chemicals Activated by P450 to Glyoxal  >> Ethanolamines (including morpholine) OR Schiff base formers >> Chemicals Activated by P450 to Glyoxal  >> Ethylenediamines (including piperazine) OR Schiff base formers >> Chemicals Activated by P450 to Mono-aldehydes OR Schiff base formers >> Chemicals Activated by P450 to Mono-aldehydes >> Benzylamines-Schiff base OR Schiff base formers >> Direct Acting Schiff Base Formers OR Schiff base formers >> Direct Acting Schiff Base Formers >> Mono aldehydes OR SN1 >> Carbenium Ion Formation OR SN1 >> Carbenium Ion Formation >> Allyl benzenes OR SN1 >> Carbenium Ion Formation >> Hydrazine OR SN1 >> Carbenium Ion Formation >> Polycyclic (PAHs) and heterocyclic (HACs) aromatic hydrocarbons-SN1 OR SN1 >> Iminium Ion Formation OR SN1 >> Iminium Ion Formation >> Aliphatic tertiary amines OR SN1 >> Nitrenium Ion formation >> Aromatic azo OR SN1 >> Nitrenium Ion formation >> Aromatic nitro OR SN1 >> Nitrenium Ion formation >> Aromatic phenylureas OR SN1 >> Nitrenium Ion formation >> Primary aromatic amine OR SN1 >> Nitrenium Ion formation >> Secondary aromatic amine OR SN1 >> Nitrenium Ion formation >> Unsaturated heterocyclic azo 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 >> Aziridines OR SN2 >> Direct Acting Epoxides and related >> Epoxides OR SN2 >> Episulfonium Ion Formation OR SN2 >> Episulfonium Ion Formation >> 1,2-Dihaloalkanes OR SN2 >> Epoxidation of Aliphatic Alkenes OR SN2 >> Epoxidation of Aliphatic Alkenes >> Halogenated polarised alkenes OR SN2 >> Nitrosation-SN2 OR SN2 >> Nitrosation-SN2 >> Nitroso-SN2 OR SN2 >> P450 Mediated Epoxidation OR SN2 >> P450 Mediated Epoxidation >> Coumarins OR SN2 >> P450 Mediated Epoxidation >> Thiophenes-SN2 OR SN2 >> Ring opening SN2 Reaction OR SN2 >> Ring opening SN2 Reaction >> Lactones OR SN2 >> Ring opening SN2 Reaction >> Sultones OR SN2 >> SN2 at an sp3 Carbon atom OR SN2 >> SN2 at an sp3 Carbon atom >> Aliphatic halides by DNA binding by OECD

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Not possible to classify according to these rules by DPRA Cysteine peptide depletion

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Low reactive OR Low reactive >> N-substituted aromatic amides by DPRA Cysteine peptide depletion

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, MW>500 OR Strong binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "m"

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

Domain logical expression index: "n"

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

Domain logical expression index: "o"

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

Domain logical expression index: "p"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 121 Da

Domain logical expression index: "q"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 416 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate showed 1.21 % biodegradation in 28 days by considering BOD as parameterand microorganisms as inoculum. As the percent biodegradation is very less it is concluded that this chemical is not readily biodegradable.

Executive summary:

Biodegradability of test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1) is predicted using OECD QSAR tool box v.3.3using log Kow as a primary descriptor. The test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate showed 1.21 % biodegradation in 28 days by considering BOD as parameterand microorganisms as inoculum. As the percent biodegradation is very less it is concluded that this chemical is not readily biodegradable.

Description of key information

Biodegradability of test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1) is predicted using OECD QSAR tool box v.3.3using log Kow as a primary descriptor. The test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate showed 1.21 % biodegradation in 28 days by considering BOD as parameterand microorganisms as inoculum. As the percent biodegradation is very less it is concluded that this 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 target compound 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1)and supporting weight of evidence studies for its closest read across chemicals with log Kow as a primary descriptor were reviewed for the biodegradation endpoint which are summarized as below.

 

Biodegradability of test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1) is predicted using OECD QSAR tool box v.3.3using log Kow as a primary descriptor. The test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate showed 1.21 % biodegradation in 28 days by considering BOD as parameterand microorganisms as inoculum. As the percent biodegradation is very less it is concluded that this chemical is not readily biodegradable.

 

In another prediction done using Estimation Programs Interface Suite (EPI suite, 2017) the biodegradation potential of the test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS No: 27059 -08 -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 as Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical  2,2'-[(3-acetamidophenyl)imino]diethyl diacetate is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from seconadary source ( J checK) for read across chemical 5-tert-butyl-2-[4-[2-[5-tert-butylbenzoxazol-2-yl]vinyl]phenyl]benzoxazole (CAS no. 1552-47-2). The Biodegradability test was carried out for 28 days, activated sludge was taken as inoculum, concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l. The percentage degradation of read across substance 5-tert-butyl-2-[4-[2-[5-tert-butylbenzoxazol-2-yl]vinyl]phenyl]benzoxazole was determined to be 1 % degradation by BOD, 0 % degradation by HPLC parameter in 28 days. Thus, based on percentage degradation, 5-tert-butyl-2-[4-[2-[5-tert-butylbenzoxazol-2-yl]vinyl]phenyl]benzoxazole is considered to be not readily biodegradable in water.

 

In another supporting weight of evidence study from seconadary source (J checK) for read across substance 3-(dimethylamino)benzoic acid (CAS no. 99-64-9). The Biodegradability test was carried out for 28 days, activated sludge was taken as inoculum and concentration of inoculum i. e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l. The percentage degradation of test substance was determined to be 0% degradation by BOD and 1% degradation by TOC removal and HPLC parameter in 28 days. These values of percentages very less, so test chemical 3-(dimethylamino)benzoic acid is considered to be not readily biodegradable.

 

On the basis of above results for target chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1)from ( EPI suite 2017 and OECD QSAR tool box v3.3 2017) and for its read across substances ( from secondary source) the target chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1)can be expected to be not readily biodegradable.