3-hydroxy-4-[(2-methoxy-5-nitrophenyl)azo]-N-(3-nitrophenyl)naphthalene-2-carboxamide

Endpoint summary

Description of key information

Biodegradation in water

Biodegradability of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS no. 6471 -49 -4) is predicted using QSAR toolbox version 3.3 (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 chemical 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). If released in to the environment, 3.53% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide in water is estimated to be 180 days (4320 hrs). The half-life (180 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2-carboxamide in sediment is estimated to be 1620.833 days (38900 hrs). However, as the percentage release of test chemical into the sediment is less than 5% (i.e, reported as 4.88%), indicates that 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2-carboxamide is not persistent in sediment.

 

Biodegradation in soil

The half-life period of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS No. 6471 -49 -4) 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, 91.6% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide in soil is estimated to be 360 days (8640 hrs). Based on this half-life value of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide, it is concluded that the chemical is persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to high.

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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl) diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). The bioconcentration factor (BCF) of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 10 L/kg whole body w.w (at 25 deg C) which does not exceed the bio concentration threshold of 2000, indicating that the chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). The soil adsorption coefficient i.e Koc value of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2-carboxamide was estimated to be 119900 L/kg (log Koc=5.0787)  by means of MCI method (at 25 deg C). This Koc value indicates that the substance 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide 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 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS No. 6471-49-4) and supporting weight of evidence studies for its read across substance were reviewed for the biodegradation end point which are summarized as below:

 

In a prediction done by SSS (2017) using OECD QSAR toolbox version 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide(CAS No. 6471-49-4) was estimated.Test substance undergoes 0.2% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamidewas 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 compound3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide(CAS No. 6471-49-4) 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 chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamideis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 1-(4-Methyl-2-nitrophenylazo)-2-naphthol (CAS no. 2425-85-6),biodegradation experiment was conducted for 28 days for evaluating the percentage biodegradability of read across substance 1-(4-Methyl-2-nitrophenylazo)-2-naphthol. 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 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol was determined to be 0 and 1% by BOD and HPLC parameter in 28 days. Thus, based on percentage degradation,1 -(4 -Methyl-2 -nitrophenylazo)-2 –naphthol is considered to be not readily biodegradable in nature.

 

For the read across chemical Disperse Blue 143 (CAS no. 61968-28-3), biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of read across substance Disperse Blue 143 (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 Disperse Blue 143 was determined to be 0 and 2.7% by BOD and HPLC parameter in 14 days. Thus, based on percentage degradation, Disperse Blue 143 is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK & EnviChem), it can be concluded that the test substance3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamidecan 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). If released in to the environment, 3.53% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide in water is estimated to be 180 days (4320 hrs). The half-life (180 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2-carboxamide in sediment is estimated to be 1620.833 days (38900 hrs). However, as the percentage release of test chemical into the sediment is less than 5% (i.e, reported as 4.88%), indicates that 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2-carboxamide is not persistent in sediment.

 

Biodegradation in soil

The half-life period of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS No. 6471 -49 -4) 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, 91.6% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide in soil is estimated to be 360 days (8640 hrs). Based on this half-life value of 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide, it is concluded that the chemical is persistent in the soil environment and the exposure risk to soil dwelling animals is moderate to high.

On the basis of available information, the test substance 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide can be considered to be not readily biodegradable in nature.

Bioaccumulation: aquatic / sediment

Various predicted data for the target compound 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS No. 6471-49-4) 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl) diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). The bioconcentration factor (BCF) of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 10 L/kg whole body w.w (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 bioaccumulation i.e BCF for test substance 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 107 dimensionless . The predicted BCF result based on the 5 OECD principles.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017) for the read across chemical 1-(4-Methyl-2-nitrophenylazo)-2-naphthol (CAS no. 2425-85-6),bioaccumulation experiment was conducted on test organism Cyprinus carpio for 6 weeks for evaluating the bioconcentration factor (BCF value) of 1-(4-Methyl-2-nitrophenylazo)-2-naphthol.The study was performed according to “OECD Guideline 305 C (Bioaccumulation: Test for the Degree of Bioconcentration in Fish)” 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 1 mg/land 0.1 mg/l, respectively. Test chemical solution was prepared in crystal sugar or HCO-40.Analytical method involve the recovery ratio: Fish : 85.8 %, - Limit of quantitation : Test water : 1st concentration area : 0.024 mg/L, 2nd concentration area : 0.0024 mg/L, Fish : 0.28 microg/g. Range finding study involve the LC50 (48hr) ≥ 400 mg/l on Rice fish (Oryzias latipes). Lipid content of the test organism Cyprinus carpio was determined to be4.2% at start of exposure. The bioconcentration factor (BCF value) of substance 1-(4-Methyl-2-nitrophenylazo)-2-naphthol on Cyprinus carpio was determined to be in the range of 0.3 – 2.7 L/Kg at a conc. of 1 mg/l and ≤ 2.9 L/Kg at a conc. of 0.1 mg/l, respectively.

 

Another bioaccumulation study was conducted for estimating the BCF (bioaccumulation factor) value of the same read across chemical 1-(4-Methyl-2-nitrophenylazo)-2-naphthol (CAS no. 2425-85-6) (HSDB, 2017). The bioaccumulation factor (BCF) value was calculated using alog Kow of 6.5 and a regression-derived equation. The estimated BCF (bioaccumulation factor) value of 1 -(4 -Methyl-2 -nitrophenylazo)-2 -naphthol was determined to be 10 dimensionless.

 

For the read across chemical 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol (CAS no. 2814-77-9),bioaccumulation study was conducted for estimating the BCF (bioaccumulation factor) value of read across chemical 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol (HSDB, 2017). The bioaccumulation factor (BCF) value was calculated using a log Kow of 6.6 and a regression-derived equation. The estimated BCF (bioaccumulation factor) valueof 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol was determined to be 10 dimensionless.

 

On the basis of above results for target chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (from EPI suiteand CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database J-CHECK and HSDB), it can be concluded that the BCF value of test substance3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamideranges from 10 – 107 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide is not expected to bioaccumulate in the food chain.

Adsorption / desorption

Various predicted data for the target compound 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS No. 6471-49-4) 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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4). The soil adsorption coefficient i.e Koc value of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2-carboxamide was estimated to be 119900 L/kg (log Koc=5.0787)  by means of MCI method (at 25 deg C).

 

The Soil Adsorption Coefficient i.e Koc value of test substance 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 208899, 222491, 223948, 224095, 224109, 224111, 224107, 224067, 223671, 219790, 187277, 75359, 10500 and 993 at pH range 0, 1, 2, 3, 4, 5-6, 7, 8, 9, 10, 11, 12, 13 and 14 respectively (logKoc value ranges from 3.0 ± 1.0 to 5.4 ± 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 3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide (CAS no. 6471 -49 -4) was estimated. The adsorption coefficient (Koc) value of test substance 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 53494.91 (Log Koc = 4.728) at pH 5.5 and 53492.33 (Log Koc = 4.728) at pH 7.4, respectively.

 

Additional soil adsorption coefficient i.e Koc value of test chemical3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl) diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide (CAS No. 6471 -49 -4)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 84300, 84600, 84700, 84600, 84300, 81000 at pH range 1, 2, 3-7, 8, 9 and 10 (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 3 -hydroxy-4 -[(E)-2 -(2 -methoxy-5 -nitrophenyl)diazen-1 -yl]-N-(3 -nitrophenyl)naphthalene-2 -carboxamide was estimated to be 236000 L/kg (log Koc = 5.372).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-Methyl-2-nitrophenylazo)-2-naphthol (CAS no. 2425-85-6), adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1-(4-Methyl-2-nitrophenylazo)-2-naphthol. 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 -Methyl-2 -nitrophenylazo)-2 –naphthol was estimated to be 130000 (Log Koc = 5.113).

 

For the read across chemical 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol (CAS no. 2814-77-9),adsorption study was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1-[(2-chloro-4-nitrophenyl)diazenyl]-2-naphthol (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 test substance 1 -[(2 -chloro-4 -nitrophenyl)diazenyl]-2 -naphthol was estimated to be 230000 (Log Koc = 5.361).

 

On the basis of above overall results for target chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamide(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 substance3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamideranges from53492.33–224111indicating that the test chemical3-hydroxy-4-[(E)-2-(2-methoxy-5-nitrophenyl)diazen-1-yl]-N-(3-nitrophenyl)naphthalene-2-carboxamidehas a very strong sorption to soil and sediment and therefore have negligible migration potential to ground water.