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Biodegradation in water: screening tests

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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: Cinnamyl formate
- IUPAC name: (2E)-3-phenylprop-2-en-1-yl formate
- Molecular formula: C10H10O2
- Molecular weight: 162.187 g/mole
- Smiles :c1(\C=C\COC=O)ccccc1
- Inchl: 1S/C10H10O2/c11-9-12-8-4-7-10-5-2-1-3-6-10/h1-7,9H,8H2/b7-4+
- Substance type: Organic
- Physical state: Liquid (Colorless to yellowish)
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:
92.4
Sampling time:
28 d
Remarks on result:
other: other details not available

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" )  and "d" )  and "e" )  and "f" )  and "g" )  and "h" )  and "i" )  and "j" )  and ("k" and ( not "l") )  )  and ("m" and ( not "n") )  )  and ("o" and ( not "p") )  )  and ("q" and ( not "r") )  )  and ("s" and "t" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Formic acid and formates by OECD HPV Chemical Categories

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Class 3 (unspecific reactivity) by Acute aquatic toxicity classification by Verhaar (Modified)

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 Not calculated by Biodeg BioHC half-life (Biowin) ONLY

Domain logical expression index: "e"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 1) ONLY

Domain logical expression index: "f"

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

Domain logical expression index: "g"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 5) ONLY

Domain logical expression index: "h"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 6) ONLY

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Biodegrades Fast by Biodeg probability (Biowin 7) ONLY

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as days - weeks by Biodeg ultimate (Biowin 3) ONLY

Domain logical expression index: "k"

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

Domain logical expression index: "l"

Referential boundary: The target chemical should be classified as AN2 OR AN2 >> Shiff base formation after aldehyde release OR AN2 >> Shiff base formation after aldehyde release >> Specific Acetate Esters OR AN2 >> Shiff base formation for aldehydes OR AN2 >> Shiff base formation for aldehydes >> Haloalkane Derivatives with Labile Halogen OR Radical OR Radical >> Generation of reactive oxygen species OR Radical >> Generation of reactive oxygen species >> Thiols OR SN1 OR SN1 >> Nucleophilic attack after carbenium ion formation OR SN1 >> Nucleophilic attack after carbenium ion formation >> Specific Acetate Esters OR SN2 OR SN2 >> Acylation OR SN2 >> Acylation >> Specific Acetate Esters OR SN2 >> Acylation involving a leaving group  OR SN2 >> Acylation involving a leaving group  >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom OR SN2 >> Alkylation, nucleophilic substitution at sp3-carbon atom >> Haloalkane Derivatives with Labile Halogen OR SN2 >> Nucleophilic substitution at sp3 Carbon atom OR SN2 >> Nucleophilic substitution at sp3 Carbon atom >> Specific Acetate Esters by DNA binding by OASIS v.1.3

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as No alert found by DNA binding by OECD

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as 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 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 >> Polarised Alkenes-Michael addition OR Michael addition >> Polarised Alkenes-Michael addition >> Alpha, beta- unsaturated esters OR Schiff base formers OR Schiff base formers >> Direct Acting Schiff Base Formers OR Schiff base formers >> Direct Acting Schiff Base Formers >> Mono aldehydes by DNA binding by OECD

Domain logical expression index: "o"

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

Domain logical expression index: "p"

Referential boundary: The target chemical should be classified as Non binder, impaired OH or NH2 group OR Non binder, non cyclic structure by Estrogen Receptor Binding

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Group 14 - Carbon C AND Group 16 - Oxygen O by Chemical elements

Domain logical expression index: "r"

Referential boundary: The target chemical should be classified as Group 15 - Nitrogen N by Chemical elements

Domain logical expression index: "s"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 134 Da

Domain logical expression index: "t"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 194 Da

Validity criteria fulfilled:
not specified
Interpretation of results:
readily biodegradable
Conclusions:
The test chemical (2E)-3-phenylprop-2-en-1-yl formate showed 92.40 % degradation by considering BOD as parameter and Microorganisms as inoculum in aerobic condition in 28 days.
Executive summary:

Biodegradability of test chemical (2E)-3-phenylprop-2-en-1-yl formate (CAS no. 104 -65 -4) was determined by using OECD QSAR tool box v3.3 with log Kow as primary descriptor. The test chemical (2E)-3-phenylprop-2-en-1-yl formate showed 92.40 % degradation by considering BOD as parameter and Microorganisms as inoculum in aerobic condition in 28 days. On the basis of percent degradation value in 28 days it is concluded that this test chemical is readily biodegradable.

Description of key information

Biodegradability of test chemical (2E)-3-phenylprop-2-en-1-yl formate (CAS no. 104 -65 -4) was determined by using OECD QSAR tool box v3.3 with log Kow as primary descriptor. The test chemical (2E)-3-phenylprop-2-en-1-yl formate showed 92.40 % degradation by considering BOD as parameter and Microorganisms as inoculum in aerobic condition in 28 days. On the basis of percent degradation value in 28 days it is concluded that this test chemical is readily biodegradable.

Key value for chemical safety assessment

Biodegradation in water:
readily biodegradable

Additional information

Predicted data for the target compound(2E)-3-phenylprop-2-en-1-yl formate (CAS no. 104 -65 -4)and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below:

In first prediction the biodegradability of test chemical (2E)-3-phenylprop-2-en-1-yl formate (CAS no. 104 -65 -4) was determined by using OECD QSAR tool box v3.3 with log Kow as primary descriptor. The test chemical (2E)-3-phenylprop-2-en-1-yl formate showed 92.40 % degradation by considering BOD as parameter and Microorganisms as inoculum in aerobic condition in 28 days. On the basis of percent degradation value in 28 days it is concluded that this test chemical is readily biodegradable.

 Another prediction was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate the biodegradation potential of the test compound (2E)-3-phenylprop-2-en-1-yl formate (CAS no. 104 -65 -4) 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 Biowin 1-7, respectively) of the BIOWIN v4.10 software. The results indicate that chemical  (2E)-3-phenylprop-2-en-1-yl formate is expected to be readily biodegradable.

Next, experimental study of read across substance 2E)-2-(phenylmethylidene)heptanal (CAS no. 122-40-7) was conducted to support the prediction study of target chemical (from Food and chemical Toxicolgy journal , 2015) in this study Biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance (2E)-2-(phenylmethylidene)heptanal under aerobic conditions. The study was performed according to OECD Guideline 301 F (Ready Biodegradability: Manometric Respirometry Test). Concentration of inoculum i.e, sludge used was 30 mg/l and initial read across substance conc. used in the study was 100 mg/l, respectively. Aniline was used as a reference substance for the study. Test vessels involve the Bottle 1 & 2: Basal culture medium + activated sludge 30 mg/l + test chemical (100 mg/l); Bottle 3: Basal culture medium + activated sludge 30mg/l+ aniline (100mg/l) and Bottle 4: Basal culture medium + activated sludge 30 mg/l. Reference substance undergoes 61% degradation in 28 days. The percentage degradation of read across substance (2E)-2-(phenylmethylidene)heptanal was determined to be 90% by BOD parameter in 28 days. Thus, based on percentage degradation, (2E)-2 -(phenylmethylidene)heptanal is considered to be readily biodegradable in nature.

 

One more experimental study was conducted for read across substance 2 -phenylethyl propanoate (PEP) (from Pest Management Science journal, 2008) in this study Biodegradation experiment was conducted for 30 days for evaluating the percentage biodegradability of 2 -phenylethyl propanoate. Pond water was used as inoculums collected from the Iowa State University Horticulture Farm pond (Ames, IA, USA). Initial read across substance conc. used for the study was 10μg/g. The pH of the water was 7.3, the alkalinity was 91 mg/ml, and the total hardness was 182 mg/ml. Pond water (100 ml) was kept in French square bottles and spiked with 3H-PEP in 300 μl of acetone carrier solvent to result in a concentration of 10 μg/ml. Samples were taken at days 0, 0.25, 0.5, 1, 3, 7, 14, 21 and 30 post-treatment. Quantitative analysis of PEP was performed using a Hewlett-Packard (Palo Alto, CA, USA) series 1100 HPLC system with a quaternary pump, an autosampler, a thermostatted column compartment, and a Spectroflow 757 absorbance detector (ABI Analytical, Kratos Division, Ramsey, NJ, USA). Data were collected and analyzed using HP Chemstation system software (REV. A.04.01). An Alltech Adsorbosphere® (Deerfield, IL, USA) C18 column (4.6×250 mm, 5-μm particle size) was used. Detection was conducted at 270 nm with a flow rate of 1.0 ml/min at room temperature. The mobile phase was methanol/distilled water (70:30, v/v).Dissipation rates of PEP were calculated using first-order open models. A student’s t-test was used to compare dissipation rates of PEP in light and in dark from the water dissipation studies. Dissipation of PEP in water was very rapid with a DT 50 of 5 days. Volatility loss was negligible in one month with mass balance from 96% to 100%. The primary degradation product was 2-phenylethanol, which was produced from ester hydrolysis of phenethyl propionate; another degradation product was 2-(4-hydroxyphenyl) ethanol, which was probably a biotransformation product of 2-phenylethanol in microbes. The percentage degradation of read across substance 2-phenylethyl propanoate was determined to be 50% in 5 days. Thus, based on percentage degradation, 2-phenylethyl propanoate is considered to be readily biodegradable in nature.

On the basis of results of above mentioned studies for target chemical (2E)-3-phenylprop-2-en-1-yl formate (CAS no. 104 -65 -4) (from OECD QSAR tool boxv3.3 and EPI suite) and supporting weight of evidence studies. It is concluded that the test chemical (2E)-3-phenylprop-2-en-1-yl formate can be expected to be readily biodegradable.