Reaction products of tetrabromophthalic anhydride with 2,2'-oxydiethanol and methyloxirane

Biodegradation in soil

Administrative data

Endpoint:

biodegradation in soil, other

Remarks:

QSAR estimate

Type of information:

calculation (if not (Q)SAR)

Remarks:

Migrated phrase: estimated by calculation

Adequacy of study:

key study

Study period:

February 2018

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Estimation method (EPI Suite) recommended in IUCLID Guidance Documents.

Justification for type of information:

1. SOFTWARE
Epi Suite US EPA version 4.11
2. MODEL (incl. version number)
BIOWIN version 4.10
3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL:
CAS: 77098-07-8
CAS: 77098-07-8
Model used:
SMILES : O=C(c1c(c(c(c(c1C(=O)OCCOCCO)Br)Br)Br)Br)OCC(C)O
CHEM : 1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, mixed esters with
diethylene glycol and propylene glycol
MOL FOR: C15 H16 Br4 O7
MOL WT : 627.91
4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
[Explain how the model fulfils the OECD principles for (Q)SAR model validation. Consider attaching the QMRF or providing a link]
- Defined endpoint: yes combination of models with different endpoints
- Unambiguous algorithm: yes
- Defined domain of applicability: yes
- Appropriate measures of goodness-of-fit and robustness and predictivity: yes
- Mechanistic interpretation: no

5. APPLICABILITY DOMAIN
[Explain how the substance falls within the applicability domain of the model]
- Descriptor domain: All relevant fragments are included in the BIOWIN models
- Structural and mechanistic domains: applicable all relevant structure fragments included
- Similarity with analogues in the training set: severla simial analogs inthe training set
- Other considerations (as appropriate): prdiction of the lower molecular weight components seems to be relaible. For the higher molecular weight components solublility and bioaccessibility may become the limiting factor. This coudl be mitagated by hydrolysis prior to degradation.

Data source

Reference

Reference Type:

other: software program

Title:

Estimation Programme EPISUITE v4.11. US EPA 2000-2012

Author:

Anonymous

Year:

2012

Bibliographic source:

U.S. Environmental Protection Agency, Washington, DC, U.S.A. http://www.epa.gov/opptintr/exposure/pubs/episuite.htm

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

Estimated using EPI Suite v4.11, BIOWIN version 4.10.

GLP compliance:

no

Test type:

other: Estimated using EPI Suite v4.11, BIOWIN v4.10

Test material

Test material information

1

Reference substance name:

Reaction products of 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate with 2,2'-oxy-diethanol and 2-epoxypropane

EC Number:

616-436-5

Cas Number:

77098-07-8

Molecular formula:

Ester product of C8 H2 Br4 O4 with C4 H10 O3 and C3 H8 O2 and condensation products, thereof.

IUPAC Name:

Reaction products of 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate with 2,2'-oxy-diethanol and 2-epoxypropane

Specific details on test material used for the study:

The model is only based on the lowest molecular weight structure of the material with one aromatic ring, one diethyleneglycol group and one propyleneglyucol residue. This may overpredict biodegradability due to the assumed lower bioavailability of the higher molecular weight componens. However thses also have th epotential to hydorlyse and degradtaion is expected as well.

Radiolabelling:

no

Results and discussion

% Degradation

Parameter:

not specified

Remarks on result:

not determinable

Half-life / dissipation time of parent compound

DT50:

ca. 2 880 h

Remarks on result:

other: calculated

Transformation products:

no

Evaporation of parent compound:

not specified

Volatile metabolites:

not specified

Residues:

not specified

Any other information on results incl. tables

The estimated half-life for biodegration in soil was 2880 hr. It is in accordance with measured values obtained for a structural analog, 1,2 -Benzenedicarboxylic acid, 3,45,6 -tetrabromo0, bis(2 -ethylhexyl) ester (CARN 26040 -51 -7).

Applicant's summary and conclusion

Conclusions:

Aerobic biodegradation in soils is not expected to be a significant route of environmental degradation. Anaerobic degration may be possible. However, the primary route for degradation of the Reference Substance in soil is expected to be via hydrolysis. A low binding coefficient indicates binding to soil particulates will not interfer with hydrolysis.

Executive summary:

Modeling indicates that soil is the most important compartment with respect to the environmental distribution of the Reference Substance. Fast aerobic biodegradation in soil is not expected based on the soil and STP modeling, however, anaerobic biodegradation may be possible. If applicable to soil, these results suggest the Reference Substance would not biodegrade in the upper aerobic soil levels, but may biodegrade in lower anaerobic levels or in other soil regions where anaerobic conditions exist. Further, hydrolysis is expected with half-lives of 1.363 and 13.69 days at pH 8 and 7, respectively. Thus, the moisture content in or on soils may allow abiotic degradation, which would proceed at faster rates than biological degradation. The low adsorption coefficient (10) indicates binding to soil will be low and thus should not affect biotic or abiotic degradation.