3,4-dicyanoaniline

Endpoint summary

Description of key information

Biodegradation in water

Biodegradability of 4-aminobenzene-1,2-dicarbonitrile (CAS no. 56765 -79 -8) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 6.36% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 4-aminobenzene-1,2-dicarbonitrile was estimated to be not readily biodegradable in water.

Biodegradation in water and sediment

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound 4-aminobenzene-1,2-dicarbonitrile

(CAS No. 56765 -79 -8). If released in to the environment, 25.3% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 4-aminobenzene-1,2-dicarbonitrile in water is estimated to be 37.5 days (900 hrs). The half-life (37.5 days estimated by EPI suite) indicates that the chemical is not persistent in water and the exposure risk to aquatic animals is moderate to low whereas the half-life period of 4-aminobenzene-1,2-dicarbonitrile in sediment is estimated to be 337.5 days (8100 hrs). However, as the percentage release of test chemical into the sediment is less than 1% (i.e, reported as 0.0856%), indicates that 4-aminobenzene-1,2-dicarbonitrile is not persistent in sediment.

 

Biodegradation in soil

The half-life period of 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 74.6% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 4-aminobenzene-1,2-dicarbonitrile in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of 4-aminobenzene-1,2-dicarbonitrile, it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to low.

Bioaccumulation: aquatic / sediment

BCFBAF model (v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The bioconcentration factor (BCF) of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 4-aminobenzene-1,2-dicarbonitrile is not expected to bioaccumulate in the food chain.

Adsorption / desorption

KOCWIN model (v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 31 L/kg (log Koc=1.4914) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a negligible sorption to soil and sediment and therefore have rapid migration potential to ground water.

Additional information

Biodegradation in water

Various predicted data for the target compound 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765-79-8) and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2017) using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical4-aminobenzene-1,2-dicarbonitrile(CAS No. 56765-79-8) was estimated.Test substance undergoes 6.36% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical4-aminobenzene-1,2-dicarbonitrilewas estimated to be not readily biodegradable in water.

 

In another prediction using the Estimation Programs Interface Suite (EPI suite, 2017), the biodegradation potential of the test compound4-aminobenzene-1,2-dicarbonitrile(CAS No. 56765-79-8) in the presence of mixed populations of environmental microorganisms was estimated.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 chemical4-aminobenzene-1,2-dicarbonitrileis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, SRC PhysProp database, 2017 and EnviChem, 2014) for the read across chemical 1,2-Dicyanobenzene (CAS no. 91-15-6),biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance 1,2-Dicyanobenzene. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)) under aerobic conditions at a temperature of 25°C and pH 7.0, respectively. Concentration of inoculum i.e, sludge used was 30 mg/l and initial test substance conc. used in the study was 100 mg/l, respectively. The percentage degradation of substance 1,2-Dicyanobenzene was determined to be3.3 and < 0% by BOD, O2 consumption, Test mat. analysis and GC parameter in 14 days. Thus, based on percentage degradation,1,2-Dicyanobenzene is considered to be not readily biodegradable in nature.

 

For the read across chemical 1-hydroxy-3-amino-benzene (CAS no. 591-27-5) from peer reviewed journal (P. Gerike and W. K. Fischer, 1981),biodegradation study was conducted for 42 days for evaluating the percentage biodegradability of read across substance 1-hydroxy-3-amino-benzene. The study was performed according to other guideline “AFNOR T 90-302 Test”. The percentage degradation of substance 1-hydroxy-3-amino-benzene was determined to be 13 and 22% degradation by DOC removal parameter after 28 and 42 days. Thus, based on percentage degradation,1-hydroxy-3-amino-benzene is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 30 days for evaluating the percentage biodegradability of the sane read across substance 1-hydroxy-3-amino-benzene (CAS no. 591-27-5) (P. Gerike and W. K. Fischer, 1981). The study was performed according to OECD Guideline 301 D (Ready Biodegradability: Closed Bottle Test).The percentage degradation of substance 1-hydroxy-3-amino-benzene was determined to be 1% by BOD parameter after 30 days. Thus, based on percentage degradation, 1-hydroxy-3-amino-benzene is considered to be not readily biodegradable in nature.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, HSDB, 2017 and EnviChem, 2014) for the read across chemical 3,4-dimethylaniline (CAS no. 95-64-7),biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 3,4-dimethylaniline. The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). Concentration of inoculum i.e, sludge used was 100 mg/l and initial test substance conc. used in the study was 30 mg/l, respectively. The percentage degradation of substance 3,4-dimethylaniline was determined to be 7.1 and 4.8% by BOD and GC parameter in 28 days. Thus, based on percentage degradation, 3,4 -dimethylaniline is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical 4-aminobenzene-1,2-dicarbonitrile (from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, SRC PhysProp database, HSDB & EnviChem and peer reviewed journal), it can be concluded that the test substance 4-aminobenzene-1,2-dicarbonitrile can be expected to be not readily biodegradable in nature.

Biodegradation in water and sediment

Estimation Programs Interface (EPI Suite, 2017) prediction model was run to predict the half-life in water and sediment for the test compound 4-aminobenzene-1,2-dicarbonitrile

(CAS No. 56765 -79 -8). If released in to the environment, 25.3% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 4-aminobenzene-1,2-dicarbonitrile in water is estimated to be 37.5 days (900 hrs). The half-life (37.5 days estimated by EPI suite) indicates that the chemical is not persistent in water and the exposure risk to aquatic animals is moderate to low whereas the half-life period of 4-aminobenzene-1,2-dicarbonitrile in sediment is estimated to be 337.5 days (8100 hrs). However, as the percentage release of test chemical into the sediment is less than 1% (i.e, reported as 0.0856%), indicates that 4-aminobenzene-1,2-dicarbonitrile is not persistent in sediment.

 

Biodegradation in soil

The half-life period of 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8) in soil was estimated using Level III Fugacity Model by EPI Suite version 4.1 estimation database (EPI suite, 2017). If released into the environment, 74.6% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 4-aminobenzene-1,2-dicarbonitrile in soil is estimated to be 75 days (1800 hrs). Based on this half-life value of 4-aminobenzene-1,2-dicarbonitrile, it is concluded that the chemical is not persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to low.

On the basis of available information, the test substance 4-aminobenzene-1,2-dicarbonitrile can be considered to be not readily biodegradable in nature.

Bioaccumulation: aquatic / sediment

Various predicted data for the target compound 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765-79-8) 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 theBCFBAF Program(v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The bioconcentration factor (BCF) of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 3.162 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 4-aminobenzene-1,2-dicarbonitrile is not expected to bioaccumulate in the food chain.

 

In an another prediction done by using Bio-concentration Factor (v12.1.0.50374) moduleACD (Advanced Chemistry Development)/I-Lab predictive module, 2017), theBCF of the test substance 4-aminobenzene-1,2-dicarbonitrile was estimated to be 2.59, 4.34, 4.66, 4.69 and 4.70 at pH range 0, 1, 2, 3 and 4-14, respectively. This value indicates that the test substance 4-aminobenzene-1,2-dicarbonitrile was considered to be non-accumulative in aquatic organisms.

 

Bioconcentration Factor (BCF) of test chemical 4-aminobenzene-1,2-dicarbonitrile was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 4-aminobenzene-1,2-dicarbonitrile was estimated to be 3.79 at both pH 5.5 and 7.4, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 4-aminobenzene-1,2-dicarbonitrile is not expected to bioaccumulate in the food chain.

 

Another predicted data was estimated usingSciFinder database (American Chemical Society (ACS), 2017) was used for predicting the bioconcentration factor (BCF) of test chemical 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The bioconcentration factor (BCF) of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 48.4, 51.9 and 52.3 at pH range 1, 2 and 3-10, respectively (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 4-aminobenzene-1,2-dicarbonitrile is not expected to bioaccumulate in the food chain.

 

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 4-aminobenzene-1,2-dicarbonitrile was estimated to be 4.31 dimensionless. The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 4-aminobenzene-1,2-dicarbonitrile is non-bioaccumulative in nature.

 

In a supporting weight of evidence study from authoritative database (J-CHECK & HSDB, 2017 and EnviChem, 2014) for the read across chemical 1,2-Dicyanobenzene (CAS no. 91-15-6),bioaccumulation experiment was conducted on test organism Cyprinus carpio for 6 weeks for evaluating the bioconcentration factor (BCF value) of 1,2-Dicyanobenzene.The study was performed according to 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 0.2mg/land 0.02 mg/l, respectively. Test chemical solution was prepared in acetone. Analytical method involve therecovery ratio: Test water : 1st concentration area : 97.0 %, 2nd concentration area : 93.5 %, Fish : 83.9 %, - Limit of detection: Fish : 0.10 ppm. Range finding study involve the TLm (48 hr) 29 mg/l (w/v) on Rice fish (Oryzias latipes). Lipid content of the test organism Cyprinus carpio was determined to be 6.9%. The bioconcentration factor (BCF value) of substance 1,2-Dicyanobenzene on Cyprinus carpio was determined to be in the range of 0.8-1.3 L/Kg at a conc. of 0.2 mg/l and ≤ 5.5 L/Kg at a conc. of 0.02 mg/l, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 1,2 -Dicyanobenzene is not expected to bioaccumulate in the food chain.

 

For the read across chemical 3,4-dimethylaniline (CAS no. 95-64-7),bioaccumulation study was conducted on test organism Cyprinus carpio for 6 weeks for evaluating the bioconcentration factor (BCF value) of 3,4-dimethylaniline (J-CHECK & HSDB, 2017 and EnviChem, 2014).The study was performed according to 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 1 mg/l and 0.1 mg/l, respectively. Range finding study involve the TLm (48 hr) 121 mg/l (w/v) on Rice fish (Oryzias latipes).The bioconcentration factor (BCF value) of substance 3,4-dimethylaniline on Cyprinus carpio was determined to be in the range of 1.9-3.3 L/Kg at a conc. of 1 mg/l and ≤ 10 L/Kg at a conc. of 0.1 mg/l, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 3,4-dimethylaniline is not expected to bioaccumulate in the food chain.

 

On the basis of above results for target chemical 4-aminobenzene-1,2-dicarbonitrile(from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database J-CHECK & HSDB and EnviChem), it can be concluded that the BCF value of test substance 4-aminobenzene-1,2-dicarbonitrile ranges from 1.77 – 4.70 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 4-aminobenzene-1,2-dicarbonitrile is not expected to bioaccumulate in the food chain.

Adsorption / desorption

Various predicted data for the target compound 4-aminobenzene-1,2-dicarbonitrile(CAS No. 56765-79-8) and supporting weight of evidence study for its read across substance were reviewed for the adsorption end point which are summarized as below:

 

In aprediction done using theKOCWIN Program(v2.00) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the soil adsorption coefficient i.e Koc value of test chemical 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 31 L/kg (log Koc=1.4914) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a negligible sorption to soil and sediment and therefore have rapid migration potential to ground water.

 

The Soil Adsorption Coefficient i.e Koc value of test substance 4-aminobenzene-1,2-dicarbonitrile (CAS no. 56765 -79 -8) was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 58, 97.3, 104 and 105  at pH range 0, 1, 2 and 3-14, respectively (log Koc value ranges from 1.8 ± 1.0 to 2.0 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017).This Koc value indicates that the test substance has a low sorption to soil and therefore have moderate migration potential to groundwater.

 

In an another prediction done by using ChemSpider Database (2017),the Soil Adsorption Coefficient i.e Koc value of test substance 4-aminobenzene-1,2-dicarbonitrile(CAS no. 56765 -79 -8) was estimated. The adsorption coefficient (Koc) value of test substance 4-aminobenzene-1,2-dicarbonitrile was estimated to be 90.34 (Log Koc = 1.9558) at both pH 5.5 and 7.4, respectively. This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a low sorption to soil and sediment and therefore have moderate migration potential to groundwater.

 

Additional soil adsorption coefficient i.e Koc value of test chemical4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 48.4, 51.9 and 52.3 at pH range 1, 2, and 3-10, respectively (log Koc value ranges from 1.6848 to 1.718) (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

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 adsorption coefficient i.e KOC for test substance 4-aminobenzene-1,2-dicarbonitrile was estimated to be 55.5 L/kg (log Koc = 1.7442).The predicted KOC result based on the 5 OECD principles. This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 1,2-Dicyanobenzene (CAS no. 91-15-6),adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1,2-Dicyanobenzene. The adsorption coefficient (Koc) value was calculated using a logKow of 0.99 and a regression derived equation. The adsorption coefficient (Koc) value of substance 1,2-Dicyanobenzene was estimated to be 82 (Log Koc = 1.9138). This Koc value indicates that the substance 1,2-Dicyanobenzene has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

For the read across chemical 3,4-dimethylaniline (CAS no. 95-64-7),adsorption study was conducted for estimating the adsorption coefficient (Koc) value of test chemical 3,4-dimethylaniline (HSDB, 2017).The adsorption coefficient (Koc) value was calculated using a logKow of 1.84 and a regression derived equation. The adsorption coefficient (Koc) value of read across substance 3,4-dimethylaniline was estimated to be 240 (Log Koc = 2.38). This Koc value indicates that the substance 3,4 -dimethylaniline has a low sorption tosoil and sediment and therefore have moderate migration potential to ground water.

 

On the basis of above overall results for target chemical 4-aminobenzene-1,2-dicarbonitrile(from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the Koc value of test substance 4-aminobenzene-1,2-dicarbonitrile ranges from 31–105indicating that the test chemical 4-aminobenzene-1,2-dicarbonitrile has a negligible to low sorption to soil and sediment and therefore have rapid to moderate migration potential to ground water.