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Biodegradation in water

Biodegradability of1,4-bis[(2-methylphenyl)amino]anthraquinone(CAS no. 6737 -68 -4) is predicted using QSAR toolbox version 3.4 (2017) with logKow as the primary descriptor. Test substance undergoes 0.2% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical1,4-bis[(2-methylphenyl)amino]anthraquinonewas estimated to be not readily biodegradable in water.

Bioaccumulation: aquatic / sediment

Using Bio-concentration Factor (v12.1.0.50374) module Bio-concentration Factor of the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS no. 6737 -68 -4) was estimated to be 6215, 7406, 7550, 7565 and 7567 at pH range 0, 1, 2, 3 and 4-14, respectively. This value indicates that the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone 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 1,4 -bis[(2 -methylphenyl)amino] anthraquinone (CAS No. 6737 -68 -4). The soil adsorption coefficient i.e Koc value of 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 4979000 L/kg (log Koc=6.6972) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone 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 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS No. 6737-68-4) and supporting weight of evidence studies for its structurally similar 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 chemical 1,4 -bis[(2 -methylphenyl) amino]anthraquinone(CAS No. 6737 -68 -4) was estimated.Test substance undergoes 0.2% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical1,4-bis[(2-methylphenyl)amino]anthraquinonewas 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 compound1,4-bis[(2-methylphenyl)amino]anthraquinone(CAS No. 6737-68-4) 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 chemical1,4-bis[(2-methylphenyl)amino]anthraquinoneis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical Alizarin Cyanin Green F (CAS no. 4403-90-1), biodegradation experiment was conducted for 5 days for evaluating the percentage biodegradability of read across substance Alizarin Cyanin Green F (CAS no. 4403-90-1) using 5 day BOD test under aerobic conditions. Sewage sludge was used as a test inoculum. Initial test substance conc. used in the study was 2.5 mg/l. The percentage degradation of substance Alizarin Cyanin Green F was determined to be 0% by BOD parameter in 5 days. Thus, based on percentage degradation, Alizarin Cyanin Green F is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of read across substance 7,12-dihydrotetraphene-7,12-dione (CAS no. 2498-66-0) (J-CHECK, 2017 and EnviChem, 2014). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I). Activated sludge was used as a test inoculums for the study. 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 7,12 -dihydrotetraphene-7,12 -dione was determined to be 1 and 3% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation, 7,12 -dihydrotetraphene-7,12 -dione is considered to be not readily biodegradable in nature.

 

For the read across chemical 1-N,4-N-diphenylbenzene-1,4-diamine (CAS no. 74-31-7) from authoritative database (J-CHECK and HSDB, 2017 & EnviChem, 2014), biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance 1-N,4-N-diphenylbenzene-1,4-diamine. The study was performed according to OECD Guideline 301 C (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-N,4-N-diphenylbenzene-1,4-diamine was determined to be 0.2 and 0.3% by BOD and GC parameter in 14 days. Thus, based on percentage degradation,1-N,4-N-diphenylbenzene-1,4-diamine is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone (from OECD QSAR toolbox version 3.4 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB and EnviChem), it can be concluded that the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone can be expected to be not readily biodegradable in nature.

Bioaccumulation: aquatic / sediment

Various predicted data and experimental study for the target compound1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS No. 6737-68-4) and supporting weight of evidence study for its structurally similar read across substance were reviewed for the bioaccumulation end point which are summarized as below:

 

In a prediction done by using Bio-concentration Factor (v12.1.0.50374) moduleACD (Advanced Chemistry Development)/I-Lab predictive module, 2017), theBio-concentration Factor (BCF) of the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS no. 6737 -68 -4) was estimated to be 6215, 7406, 7550, 7565 and 7567 at pH range 0, 1, 2, 3 and 4-14, respectively. This value indicates that the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone was considered to be very bioaccumulative in aquatic organisms.

 

Bioconcentration Factor (BCF) of test chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 6684.17 at pH 5.5 and 6684.65 at pH 7.4, respectively, which exceeds the bioconcentration threshold of 5000, indicating that the chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone is expected to very 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 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS No. 6737 -68 -4). The bioconcentration factor (BCF) of 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 118000 at pH 1 and 120000 at pH range 2-10, respectively (at 25 deg C) which does exceeds the bio-concentration threshold of 5000, indicating that the chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone is expected to very bioaccumulate in the food chain.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 1,4-bis(isopropylamino)-9,10-anthraquinone (CAS no. 14233-37-5),bioaccumulation experiment was conducted on test organism Cyprinus carpio for 60 days for evaluating the bioconcentration factor (BCF value) of 1,4-bis(isopropylamino)-9,10-anthraquinone. 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 0.001mg/l and 0.0001 mg/l, respectively. Test chemical solution was prepared in HCO-20. Analytical method involve the recovery ratio: Test water :96.9%, Fish : 84.9 %, - Limit of quantitation : Test water : 1st concentration area : 0.058 microg/L, 2nd concentration area : 0.0058 microg/L, Fish : 6.2 ng/g. Range finding study involve the LC50 (96 hr) > 0.100 mg/l (w/v) on Rice fish (Oryzias latipes).The bioconcentration factor (BCF value) of substance 1,4-bis(isopropylamino)-9,10-anthraquinone on Cyprinus carpio was determined to be 5400 L/Kg at a conc. of 0.001 mg/l and 5300 L/Kg at a conc. of 0.0001 mg/l, respectively, which exceeds the bioconcentration threshold of 5000, indicating that the chemical 1,4-bis(isopropylamino)-9,10-anthraquinone is expected to very bioaccumulate in the food chain.

 

On the basis of above overall results for target chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone (from ACD labs,ChemSpider and Scifinder,2017) and for its read across substance from authoritative database (J-CHECK, 2017), it can be concluded that the BCF value of test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone ranges from 6215– 120000, which does exceeds the bioconcentration threshold of 5000, indicating that the chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone is expected to be very bioaccumulate in the food chain.

Adsorption / desorption

Various predicted data for the target compound 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS No. 6737-68-4) and supporting weight of evidence study for its structurally similar 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 1,4 -bis[(2 -methylphenyl)amino] anthraquinone (CAS No. 6737 -68 -4). The soil adsorption coefficient i.e Koc value of 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 4979000 L/kg (log Koc=6.6972) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

The Soil Adsorption Coefficient i.e Koc value of test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS no. 6737 -68 -4) was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 17087, 20360, 20758, 20798, 20802 and 20803 at pH range 0, 1, 2, 3, 4 and 5-14, respectively (log Koc ranges from 4.2 ± 1.0 to 4.3 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017). This Koc value indicates that the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a strong sorption to soil and therefore have negligible to slow 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 1,4-bis[(2-methylphenyl)amino]anthraquinone (CAS no. 6737 -68 -4) was estimated. The adsorption coefficient (Koc) value of test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 19034.94 (Log Koc = 4.279) at pH 5.5 and 19036.30 (Log Koc = 4.279) at 7.4, respectively. This Koc value indicates that the test substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a strong sorption to soil and therefore have negligible to slow migration potential to groundwater.

 

Additional soil adsorption coefficient i.e Koc value of test chemical1,4 -bis[(2 -methylphenyl)amino] anthraquinone (CAS No. 6737 -68 -4)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 1,4 -bis[(2 -methylphenyl)amino]anthraquinone was estimated to be 147000, 150000 and 151000 at pH range 1, 2 and 3-10, respectively (log Koc ranges from 5.167 to 5.178) (at 25 deg C). This Koc value indicates that the substance 1,4-bis[(2-methylphenyl)amino]anthraquinone has a very strong sorption to soil and sediment and therefore have negligible 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 1,4-bis[(2-methylphenyl)amino]anthraquinone was estimated to be 69000 L/kg (log Koc = 4.838).The predicted KOC result based on the 5 OECD principles. This Koc value indicates that the substance 1,4 -bis[(2 -methylphenyl)amino]anthraquinone has a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.

 

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 test 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 tosoil and sediment and therefore have negligible migration potential to ground water.

 

For the read across chemical 1-N,4-N-diphenylbenzene-1,4-diamine (CAS no. 74-31-7), adsorption study was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1-N,4-N-diphenylbenzene-1,4-diamine (HSDB, 2017). 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 -N,4 -N-diphenyl benzene-1,4 -diaminewas estimated to be 130000 (Log Koc = 5.113). This Koc value indicates that the substance 1 -N,4 -N-diphenylbenzene-1,4 -diamine 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 chemical 1,4-bis[(2-methylphenyl)amino]anthraquinone (from EPI suite, ACD labs,ChemSpider, Scifinder 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 substance1,4-bis[(2-methylphenyl)amino]anthraquinone ranges from 19036.30–4979000, indicating that the test chemical 1,4 -bis[(2 -methylphenyl)amino]anthraquinone has a strong to very strong sorption to soil and sediment and therefore have negligible to slow migration potential to ground water.