5-methyl-3-phenylisoxazole-4-carbonyl chloride

Bioaccumulation: aquatic / sediment

Link to relevant study record(s)

Reference

Endpoint:

bioaccumulation in aquatic species, other

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

Estimated data generated using the EPI Suite program developed by the USEPA.

Qualifier:

according to guideline

Guideline:

other: Modeling database

Principles of method if other than guideline:

Prediction done using BCFBAF (v3.01) model

GLP compliance:

not specified

Specific details on test material used for the study:

- Name of test material (IUPAC name): 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride
- Common name: 5-methyl-3-phenylisoxazole-4-carbonyl chloride
- Molecular formula : C11H8ClNO2
- Molecular weight : 221.642 g/mol
- Smiles notation : c1(ccccc1)c1c(C(=O)Cl)c(on1)C
- InChl : 1S/C11H8ClNO2/c1-7-9(11(12)14)10(13-15-7)8-5-3-2-4-6-8/h2-6H,1H3
- Substance type: Organic
- Physical state: Solid

Radiolabelling:

not specified

Vehicle:

not specified

Test organisms (species):

other: Fish

Route of exposure:

aqueous

Test type:

not specified

Water / sediment media type:

natural water: freshwater

Test temperature:

25 deg.C

Reference substance (positive control):

not specified

Key result

Temp.:

25 °C

Type:

BCF

Value:

9.256 L/kg

Basis:

whole body w.w.

Calculation basis:

other: estimated

Remarks on result:

other: Non-bioaccumulative

BCFBAF Program (v3.01) Results:

==============================

SMILES : O=C(c(c(no1)c(cccc2)c2)c1C)CL

CHEM : 4-Isoxazolecarbonyl chloride, 5-methyl-3-phenyl-

MOL FOR: C11 H8 CL1 N1 O2

MOL WT : 221.64

--------------------------------- BCFBAF v3.01 --------------------------------

Summary Results:

Log BCF (regression-based estimate): 0.97 (BCF = 9.26 L/kg wet-wt)

Biotransformation Half-Life (days) : 0.0779 (normalized to 10 g fish)

Log BAF (Arnot-Gobas upper trophic): 0.85 (BAF = 7.05 L/kg wet-wt)

Log Kow (experimental): not available from database

Log Kow used by BCF estimates: 1.97

Equation Used to Make BCF estimate:

Log BCF = 0.6598 log Kow - 0.333 + Correction

Correction(s): Value

No Applicable Correction Factors

Estimated Log BCF = 0.966 (BCF = 9.256 L/kg wet-wt)

Validity criteria fulfilled:

not specified

Conclusions:

The bioconcentration factor (BCF) of 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated to be 9.256 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride is not expected to bioaccumulate in the food chain.

Executive summary:

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 5 -methyl-3 -phenyl-1,2 -oxazole-4 -carbonyl chloride (CAS No. 16883 -16 -2). The bioconcentration factor (BCF) of 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated to be 9.256 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride is not expected to bioaccumulate in the food chain.

Description of key information

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 5 -methyl-3 -phenyl-1,2 -oxazole-4 -carbonyl chloride (CAS No. 16883 -16 -2). The bioconcentration factor (BCF) of 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated to be 9.256 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride is not expected to bioaccumulate in the food chain.

Key value for chemical safety assessment

BCF (aquatic species):

9.256 L/kg ww

Additional information

Various predicted data for the target compound 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride (CAS No. 16883-16-2) and supporting weight of evidence study for its read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In aprediction done using the BCFBAF Program(v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 5 -methyl-3 -phenyl-1,2 -oxazole-4 -carbonyl chloride (CAS No. 16883 -16 -2). The bioconcentration factor (BCF) of 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated to be 9.256 L/kg whole body w.w (at 25 deg C).

 

In an another prediction done by using Bio-concentration Factor (v12.1.0.50374) moduleACD (Advanced Chemistry Development)/I-Lab predictive module, 2017), theBCF over the entire pH scale (pH 0 -14) of the test substance 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride (CAS no. 16883 -16 -2) was estimated to be 14.6.

 

Bioconcentration Factor (BCF) of test chemical 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated to be 26.95 at both pH 5.5 and 7.4, respectively.

 

Another predicted data was estimated usingSciFinder database (American Chemical Society (ACS), 2017) was used for predicting the bioconcentration factor (BCF) of test chemical5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride(CAS No. 16883-16-2). The bioconcentration factor (BCF) of 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated to be 277 (at 25 deg C).

 

From CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical), the bioaccumulation i.e BCF for test substance 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride was estimated to be 44.1 dimensionless . The predicted BCF result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017 and EnviChem, 2014) and from secondary source (OECD SIDS, 1998) for the read across chemical 2-Phenylpropene (CAS no. 98-83-9),bioaccumulation experiment was conducted on test organism Cyprinus carpio for 8 weeks for evaluating the bioconcentration factor (BCF value) of chemical 2-Phenylpropene (CAS no. 98-83-9).The study was performed according to OECD Guideline 305 (Bioconcentration: Flow-through Fish Test) and other guideline "Bioaccumulation test of a chemical substance in fish or shellfish" provided in "the Notice on the Test Method Concerning New Chemical Substances", respectively at a temperature of 25°C.Cyprinus carpio was used as a test organism for the study. Test chemical nominal conc. used for the study were 0.3mg/land 0.03 mg/l, respectively. Test chemical solution was prepared in Tween 80.Analytical method involve the recovery ratio: Test water: 1st concentration area: 89.4 %, 2nd concentration area : 81.8 %, Fish : 77.6%, - Limit of detection : 0.055 ppm. Range finding study involve the TLm (48 hr) 6.8 mg/l (w/v) on Rice fish (Oryzias latipes).The bioconcentration factor (BCF value) of 2-Phenylpropene on Cyprinus carpio was determined to be in the range of 15-140 L/Kg at a conc. of 0.3 mg/l and 12-113 L/Kg at a conc. of 0.03 mg/l, respectively.

 

For the read across chemical (1-bromoethenyl)benzene (CAS no. 98-81-7), bioaccumulation study was conducted on test organism Cyprinus carpio for 35 days for evaluating the bioconcentration factor (BCF value) of chemical (1-bromoethenyl)benzene (J-CHECK, 2017).The study was performed according to OECD Guideline 305 (Bioconcentration: Flow-through Fish Test)and other guideline "Bioaccumulation test of a chemical substance in fish or shellfish" provided in "the Notice on the Test Method Concerning New Chemical Substances", respectively. Cyprinus carpio was used as a test organism for the study. Test chemical nominal conc. used for the study were 0.02mg/land 0.002mg/l, respectively. Test chemical solution was prepared in HCO-40.Analytical method involve the recovery ratio: Test water: 1st concentration area : 97.2 %, Fish : 83.9 %, - Limit of detection : Test water: 1st concentration area : 0.49 µg/l, 2nd concentration area : 0.049 µg/l, Fish : 17 ng/g. Range finding study involve the LC50 (96 hr) 2.22 mg/l on Rice fish (Oryzias latipes). Lipid content of the test organism Cyprinus carpio was determined to be2.23 and 2.98% at the start and end of exposure. The bioconcentration factor (BCF value) of substance(1-bromoethenyl)benzene on Cyprinus carpio was determined to be in the range of 54-157 L/Kg and 101 L/Kg at a conc. of 0.02 mg/l and 52-150 L/Kg and 102 L/Kg at a conc. of 0.002mg/l, respectively.

 

On the basis of above results for target chemical 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride(from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database J-CHECK & EnviChem and secondary source OECD SIDS), it can be concluded that the BCF value of test substance5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chlorideranges from 9.256 – 277 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chlorideis not expected to bioaccumulate in the food chain.