Cinnamonitrile

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 (IUPAC name): (E)-3-phenylprop-2-enenitrile
- Common name: Cinnamyl nitrile
- Molecular formula: C9H7N
- Molecular weight: 129.161 g/mol
- Smiles notation: N#C\C=C\c1ccccc1
- InChl: 1S/C9H7N/c10-8-4-7-9-5-2-1-3-6-9/h1-7H/b7-4+
- Substance type: Organic

Inoculum or test system:

other: Microorganisms

Duration of test (contact time):

28 d

Parameter followed for biodegradation estimation:

other: BOD

Key result

Parameter:

other: % degradation (BOD)

Value:

1.186

Sampling time:

28 d

Remarks on result:

other: other details not available

Details on results:

The test chemical (E)-3-phenylprop-2-enenitrile showed 1.1857 % biodegradation by considering BOD 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" )  and "e" )  and "f" )  and "g" )  and "h" )  and ("i" and ( not "j") )  )  and ("k" and ( not "l") )  )  and ("m" and ( not "n") )  )  and "o" )  and "p" )  and "q" )  and ("r" and "s" )  )

Domain logical expression index: "a"

Referential boundary: The target chemical should be classified as Alkene AND Aryl AND Nitrile by Organic Functional groups

Domain logical expression index: "b"

Referential boundary: The target chemical should be classified as Alkene AND Aryl AND Nitrile AND Overlapping groups by Organic Functional groups (nested)

Domain logical expression index: "c"

Referential boundary: The target chemical should be classified as Acetylenic Carbon [#C] AND Aromatic Carbon [C] AND Olefinic carbon [=CH- or =C<] by Organic functional groups (US EPA)

Domain logical expression index: "d"

Referential boundary: The target chemical should be classified as Aromatic compound by Organic functional groups, Norbert Haider (checkmol)

Domain logical expression index: "e"

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

Domain logical expression index: "f"

Referential boundary: The target chemical should be classified as Does NOT Biodegrade Fast by Biodeg probability (Biowin 6) ONLY

Domain logical expression index: "g"

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

Domain logical expression index: "h"

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

Domain logical expression index: "i"

Referential boundary: The target chemical should be classified as Not categorized by US-EPA New Chemical Categories

Domain logical expression index: "j"

Referential boundary: The target chemical should be classified as Acid Chlorides OR Aldehydes (Acute toxicity) OR Aliphatic Amines OR Anhydrides, Carboxylic acid OR Anilines (Acute toxicity) OR Anionic Surfactants OR Benzotriazole-hindered phenols OR Benzotriazoles (Acute toxicity) OR beta-Naphthylamines, Sulfonated OR Cationic (quaternary ammonium) surfactants OR Dianilines OR Diisocyanates OR Epoxides OR Esters (Acute toxicity) OR Esters (Chronic toxicity) OR Hydrazines and Related Compounds OR Imides (Acute toxicity) OR Neutral Organics OR Organotins (Acute toxicity) OR Peroxides OR Phenols (Acute toxicity) OR Polynitroaromatics (Acute toxicity) OR Soluble complexes of Zinc OR Substituted Triazines (Acute toxicity) OR Thiols (Acute toxicity) by US-EPA New Chemical Categories

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 Moderate binder, OH grooup OR Non binder, impaired OH or NH2 group OR Non binder, MW>500 OR Strong binder, OH group OR Weak binder, OH group by Estrogen Receptor Binding

Domain logical expression index: "m"

Referential boundary: The target chemical should be classified as No pKa value AND No pKb value by Ionization at pH = 1

Domain logical expression index: "n"

Referential boundary: The target chemical should be classified as Acidic [0,10) OR Acidic [20,30) OR Acidic [90,100] OR Basic [0,10) OR Basic [10,20) OR Basic [20,30) OR Basic [30,40) OR Basic [50,60) OR Basic [70,80) OR Basic [90,100] by Ionization at pH = 1

Domain logical expression index: "o"

Referential boundary: The target chemical should be classified as Fast by Bioaccumulation - metabolism half-lives ONLY

Domain logical expression index: "p"

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

Domain logical expression index: "q"

Referential boundary: The target chemical should be classified as Not calculated by Hydrolysis half-life (pH 6.5-7.4) ONLY

Domain logical expression index: "r"

Parametric boundary:The target chemical should have a value of Molecular weight which is >= 118 Da

Domain logical expression index: "s"

Parametric boundary:The target chemical should have a value of Molecular weight which is <= 154 Da

Validity criteria fulfilled:

not specified

Interpretation of results:

not readily biodegradable

Conclusions:

The test chemical (E)-3-phenylprop-2-enenitrile showed 1.1857 % biodegradation by considering BOD parameter and Microorganisms as inoculum in 28 days. Based on percent biodegradability value it is concluded that this test chemical is not readily biodegradable.

Executive summary:

Biodegradability of test chemical (E)-3-phenylprop-2-enenitrile (CASno.1885-38-7) was predicted by using OECD QSAR tool box v3.3 with log Kow as primary descriptor. The test chemical (E)-3-phenylprop-2-enenitrile showed 1.1857 % biodegradation by considering BOD parameter and Microorganisms as inoculum in 28 days. Based on percent biodegradability value it is concluded that this test chemical is not readily biodegradable.

Description of key information

Biodegradability of test chemical (E)-3-phenylprop-2-enenitrile (CASno.1885-38-7) was predicted by using OECD QSAR tool box v3.3 with log Kow as primary descriptor. The test chemical (E)-3-phenylprop-2-enenitrile showed 1.1857 % biodegradation by considering BOD parameter and Microorganisms as inoculum in 28 days. Based on percent biodegradability value it is concluded that this test 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 the target compound (E)-3-phenylprop-2-enenitrile (CAS no.1885-38-7)and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which is summarized as below:

In first weight of evidence study biodegradability of test chemical (E)-3-phenylprop-2-enenitrile (CASno.1885-38-7) was predicted by using OECD QSAR tool box v3.3 with log Kow as primary descriptor. The test chemical (E)-3-phenylprop-2-enenitrile showed 1.1857 % biodegradation by considering BOD parameter and Microorganisms as inoculums in 28 days. Based on percent biodegradability value it is concluded that this test chemical is not readily biodegradable.

 Another prediction was done by using Estimation Programs Interface Suite (EPI suite, 2017) to estimate biodegradation potential of the test compound(E)-3-phenylprop-2-enenitrile (CAS no. 1885-38-7) 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 (E)-3-phenylprop-2-enenitrileis expected to be not readily biodegradable.

In supporting weight of evidence study Biodegradation experiment was carried out according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)) for evaluating the percentage biodegradability of read across substance (2-bromovinyl)benzene (CAS no. 103-64-0) from Eisei Kagaku journal (1988). Initial test substance conc. used in the study was 20 mg/L. A water, acetone or DMSO solution (0.1 ml) of the read across chemical was added to a mixture of river/sea water (4.9 ml) from an unpolluted area and an autoclaved solution (5.0ml) of 0.2% peptone in a sterile test tube with a tight plug. After sealed with film and fixed at an angle of 30°in a dark box, the test tubes were incubated at 30°C and shaked at 120rpm. Inoculum used for the study was mixed culture obtained from different sources (Sea water from Enoshima Beach and River water from Tama River).The percentage degradation of test substance in both river and sea water was determined to be 5 and 6% by BOD parameter in 3 days. Thus, based on percentage degradation, read across chemical (2-bromovinyl)benzene is considered to be not readily biodegradable in nature.

Another weight of evidence study done from authoritative database ( Jcheck, 2017) for read across chemical (2 -bromovinyl)benzene (CAS no.103-62-4). In this study Biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance (2 -bromovinyl)benzene (CAS no. 103-62-4). 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 was determined to be 0 and 4% degradation by BOD and GC parameter in 28 days. Thus, based on percentage degradation, read across chemical (2 -bromovinyl)benzene is considered to be not readily biodegradable in nature.

On the basis of results of above mentioned studies for target chemical (E)-3-phenylprop-2-enenitrile (CAS no.1885-38-7) (from OECD QSAR tool box v3.3 and EPI suite) and supporting weight of evidence study. It is concluded that the test chemical (E)-3-phenylprop-2-enenitrile can be expected to be not readily biodegradable.