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Biodegradation in water

Biodegradability of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no. 15958 -68 -6) is predicted using OECD QSAR toolbox version 3.4 (2017) with logKow as the primary descriptor. Test substance undergoes 0.86% degradation by BOD in 28 days.Thus, based on percentage degradation, the test chemical 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10-dione 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 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). If released in to the environment, 8.61% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione in water is estimated to be 60 days (1440 hrs). The half-life (60 days estimated by EPI suite) indicates that the chemical is persistent in water and the exposure risk to aquatic animals is moderate to high whereas the half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione in sediment is estimated to be 541.66 days (13000 hrs). However, as the percentage release of test chemical into the sediment is less than 1% (i.e, reported as 0.217%), indicates that 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione is not persistent in sediment.

Biodegradation in soil

The half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS No. 15958 -68 -6) 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, 91.2% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione in soil is estimated to be 120 days (2880 hrs). Based on this half-life value of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione, 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

Using Bio-concentration Factor (v12.1.0.50374) module ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017), Bio-concentration Factor of the test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was estimated to be 13.2, 105, 3163, 20186,  31556, 33340, 33528, 33547 and 33549 at pH range 0, 1, 2, 3, 4, 5, 6, 7 and 8-14, respectively. This value indicates that the test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was considered to be very bioaccumulative in aquatic organisms.

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 1,5 -bis(cyclo hexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene -9,10 -dione was estimated to be 35140.0 L/kg (log Koc= 4.5458)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10 -dione has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

Additional information

Biodegradation in water

Various predicted data for the target compound 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) and supporting weight of evidence studies for its closest 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 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemical1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) was estimated.Test substance undergoes 0.86% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10-dione was 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 compound1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) 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 chemical 1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10-dione is expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, HSDB, SRC (Syracuse Research Corporation) PhysProp 2017 and Envichem, 2014) for the read across chemical 2-amino-9,10-dihydroanthracene-9,10-dione (CAS no. 117-79-3), biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 2 -amino-9,10 -dihydroanthracene-9,10 -dione. 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 of 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 2 -amino-9,10 -dihydroanthracene-9,10 -dione was determined to be 1 and 3% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 2 -amino-9,10 -dihydroanthracene-9,10 -dione is considered to be not readily biodegradable in nature.

 

For the read across chemical 1-hydroxy-9,10-dihydroanthracene-9,10-dione (CAS no. 129-43-1), biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1-hydroxy-9,10-dihydroanthracene-9,10-dione (J-CHECK, HSDB, SRC (Syracuse Research Corporation) PhysProp database, 2017). 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 of 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 -hydroxy-9,10 -dihydroanthracene-9,10 -dione was determined to be 2 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,1 -hydroxy-9,10 -dihydroanthracene-9,10 -dione is considered to be not readily biodegradable in nature.

 

Another biodegradation study from authoritative database (J-CHECK, 2017) and secondary source (OECD SIDS, 1996) was conducted for 28 days for evaluating the percentage biodegradability of read across substance sodium 1-amino-9,10-dihydroanthracene-9,10-dione (CAS no. 82-45-1). The study was performed according to OECD Guideline 301C “Ready biodegradability: Modified MITI Test (I)” under aerobic conditions. 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-amino-9,10-dihydroanthracene-9,10-dione was determined to be 0 and 2% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,1-amino-9,10-dihydroanthracene-9,10-dione is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(from OECD QSAR toolbox version 3.4 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB, SRC (Syracuse Research Corporation) PhysProp and secondary source OECD SIDS), it can be concluded that the test substance1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dionecan 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 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). If released in to the environment, 8.61% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione in water is estimated to be 60 days (1440 hrs). The half-life (60 days estimated by EPI suite) indicates that the chemical is persistent in water and the exposure risk to aquatic animals is moderate to high whereas the half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione in sediment is estimated to be 541.66 days (13000 hrs). However, as the percentage release of test chemical into the sediment is less than 1% (i.e, reported as 0.217%), indicates that 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione is not persistent in sediment.

Biodegradation in soil

The half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS No. 15958 -68 -6) 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, 91.2% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione in soil is estimated to be 120 days (2880 hrs). Based on this half-life value of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione, 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 substance1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dionecan be considered to be notreadily biodegradable in nature.

Bioaccumulation: aquatic/sediment

Various predicted data for the target compound 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS No. 15958-68-6) were reviewed for the bioaccumulation end point which are summarized as below:

 

In a prediction done byUsing Bio-concentration Factor (v12.1.0.50374) moduleACD (Advanced Chemistry Development)/I-Lab predictive module, 2017), theBCF of the test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was estimated to be 13.2, 105, 3163, 20186,  31556, 33340, 33528, 33547 and 33549 at pH range 0, 1, 2, 3, 4, 5, 6, 7 and 8-14, respectively. This value indicates that the test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was considered to be very bioaccumulative in aquatic organisms.

 

Bioconcentration Factor (BCF) of test chemical 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no.15958 -68 -6) as estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was estimated to be 16936.89 at pH 5.5 and 16970.10 at pH 7.4, respectively, which exceeds the bioconcentration threshold of 5000, indicating that the chemical 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene-9,10 -dione is expected to very bioaccumulative 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 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). The bioconcentration factor (BCF) of 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was estimated to be 351, 10500, 67200, 105000, 111000 and 112000 at pH range 0, 1, 2, 3, 4, 5 and 6-10, respectively (at 25 deg C) which exceeds the bioconcentration threshold of 5000, indicating that the chemical 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione is  expected to very bioaccumulative in the food chain.

 

On the basis of above results for target chemical1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(from ACD labs,ChemSpider and SciFinder database,  2017), it can be concluded that the BCF value of test substance1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione ranges from 13.2 –112000which exceeds the bioconcentration threshold of 5000, indicating that the chemical 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione is expected to be very bioaccumulative in the food chain.

Adsorption/desorption

Various predicted data for the target compound1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(CAS No. 15958-68-6) 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 1,5 -bis(cyclo hexylamino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6). The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene -9,10 -dione was estimated to be 35140.0 L/kg (log Koc= 4.5458)  by means of MCI method (at 25 deg C).

 

The Soil Adsorption Coefficient i.e Koc value of test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no. 15958 -68 -6) was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 23.8 , 190, 5695, 36344, 56816, 60027, 60366, 60400 and 60404 at pH range 0, 1, 2, 3, 4, 5, 6, 7 and 8 -14 respectively (log Koc value range from1.4 ± 1.0 to 4.8 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017).

 

In an another prediction done by using ChemSpider Database (2017),the Soil Adsorption Coefficient i.e Koc value of test substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione (CAS no. 15958 -68 -6) was estimated. The adsorption coefficient (Koc) value of substance 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione was estimated to be 37011.89 (Log Koc = 4.568) at pH 5.5 and 37084.46 (Log Koc = 4.569) at pH 7.4, respectively.

 

Additional soil adsorption coefficient i.e Koc value of test chemical1,5 -bis(cyclohexyl amino)-9,10 -dihydroanthracene-9,10 -dione (CAS No. 15958 -68 -6)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 1,5 -bis(cyclohexylamino)-9,10 -dihydroanthracene-9,10 -dione was estimated to be 449, 13500, 85900, 134000, 142000 and 143000 at pH range 1, 2, 3, 4, 5 and 6 -10, respectively (log Koc value ranges from 2.652 to 5.15) (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 adsorption coefficient i.e KOC for test substance 1,5 -bis(cyclohexylamino)-9,10 -dihydro anthracene-9,10 -dione (CAS no. 15958 -68 -6) was estimated to be 119000 L/kg (log Koc = 5.07).The predicted KOC result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 1,4-Bis(p-tolylamino)anthraquinone (CAS no.128-80-3), adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1,4-Bis(p-tolylamino)anthraquinone. The adsorption coefficient (Koc) value was calculated using a structure estimation method based on molecular connectivity indices. The adsorption coefficient (Koc) value of substance 1,4 -Bis(p-tolylamino)anthraquinone was estimated to be 4800000 (Log Koc = 6.681). This Koc value indicates that the substance 1,4 -Bis(p-tolylamino)anthraquinone has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

On the basis of above overall results for target chemical1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione(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 substance1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dione ranges from 23.8 –143000indicating that the test chemical 1,5-bis(cyclohexylamino)-9,10-dihydroanthracene-9,10-dionehas a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.