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

Endpoint summary

Description of key information

Biodegradation in water

Biodegradability of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]naphthalene-2-carboxamide (CAS no. 6410 -30 -6) is predicted using OECD QSAR toolbox version 3.4 (2017) with logKow as the primary descriptor. Test substance undergoes 4.4% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical

N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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 N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide (CAS No. 6410 -30 -6). If released in to the environment, 3.86% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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 N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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 3.93%), indicates that N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide is not persistent in sediment.

 

Biodegradation in soil

The half-life period of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]naphthalene-2-carboxamide (CAS No. 6410 -30 -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, 92.2% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]naphthalene-2-carboxamide in soil is estimated to be 360 days (8640 hrs). Based on this half-life value of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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.

Additional information

Biodegradation in water

Various predicted data for the target compound N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]naphthalene-2-carboxamide (CAS No. 6410-30-6) 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 3.4 with logKow as the primary descriptor, percentage biodegradability of test chemical N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide (CAS No. 6410 -30 -6) was estimated.Test substance undergoes 4.4% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide 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 compound N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide (CAS No. 6410 -30 -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  N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide is expected to be not readily biodegradable.

 

For the read across chemical(1Z)-1-(phenylhydrazinylidene)naphthalen-2-one(CAS no. 842-07-9),the carbon dioxide evolution test (former Sturm test) is a static method used for evaluating the ultimate aerobic biodegradability of a read across substance(1Z)-1-(phenylhydrazinylidene)naphthalen-2-onein water (Sustainability Support Services (Europe) AB has letter of access, Report no. 03/0063/36/ 1, 2003). Activated sludge was obtained from laboratory wastewater plant treating municipal sewage. Activated sludge of a concentration of 30 mg/I dry substance was pre-aerated for about two days before the start of the test. Mixtures of the test substance, a defined inorganic medium and a non pre-adapted inoculurn (e .g. activated sludge or effluent of a municipal or laboratory waste water treatment plant) are incubated and aerated at room temperature up to 28 days. The biologically produced carbon dioxide is trapped in a 0,25 mol. potassium hydroxide solution. The production of carbon dioxide (C02) is a clear indication of biodegradation. The measured amount of carbon dioxide at the end of the test is compared with the calculated maximal theoretical production (ThC02) and indicated as biodegradation degree in percent. The conductivity shift of the absorption solution is used for calculating of the C02 production. Biodegradation degree of the reference substance after 14 days (% CO2/ThCO2): 60 - 70%. The percentage degradation of the read across substance (1Z)-1-(phenylhydrazinylidene)naphthalen-2-onewas determined to be <10% in 28 days by CO2/ThCO2 parameter. Thus, the substance(1Z)-1-(phenylhydrazinylidene)naphthalen-2-oneis considered to be not readily biodegradable according to OECD criteria.

 

In a supporting weight of evidence study from authoritative database (J-CHECK, 2017 and Envichem, 2014) and secondary source (OECD SIDS, 1999 and HPVIS, 2017) for the read across chemical Barium bis[2-chloro-5-[(2-hydroxy-1-naphthyl)azo]toluene-4-sulphonate] (CAS no. 5160-02-1), biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance Barium bis[2-chloro-5-[(2-hydroxy-1-naphthyl)azo]toluene-4-sulphonate]. 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 read across substance Barium bis[2 -chloro-5 -[(2 -hydroxy-1 -naphthyl)azo]toluene-4 -sulphonate] was determined to be 0% by BOD parameter in 14 days. Thus, based on percentage degradation, Barium bis[2 -chloro-5 -[(2 -hydroxy-1 -naphthyl)azo]toluene-4 -sulphonate] is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 28 days for evaluating the percentage biodegradability of the same read across substance Barium bis[2 -chloro-5 -[(2 -hydroxy-1 -naphthyl)azo]toluene-4 -sulphonate] (CAS no. 5160 -02 -1) (OECD SIDS, 1999 and HPVIS, 2017). The study was performed according to OECD Guideline 302 B (Inherent biodegradability: Zahn-Wellens/EMPA Test) under aerobic conditions. Activated sludge was used as a test inoculum for the study. Initial test substance conc. used in the study was 1300 mg/l. The percentage degradation of read across substance Barium bis[2 -chloro-5 -[(2 -hydroxy-1 -naphthyl)azo] toluene-4 -sulphonate] was determined to be 25, 26, 28 and 33% in 5, 10, 15 and 21 days, respectively. Thus, based on percentage degradation, Barium bis[2 -chloro-5 -[(2 -hydroxy-1 -naphthyl)azo]toluene-4 -sulphonate] is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemicalN-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]naphthalene-2-carboxamide(from OECD QSAR toolbox version 3.4 and EPI suite, 2017) and for its read across substance (from experimental study report, authoritative database J-CHECK, Envichem and secondary source), it can be concluded that the test substanceN-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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 N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide (CAS No. 6410 -30 -6). If released in to the environment, 3.86% of the chemical will partition into water according to the Mackay fugacity model level III and the half-life period of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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 N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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 3.93%), indicates that N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide is not persistent in sediment.

 

Biodegradation in soil

The half-life period of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]naphthalene-2-carboxamide (CAS No. 6410 -30 -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, 92.2% of the chemical will partition into soil according to the Mackay fugacity model level III. The half-life period of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]naphthalene-2-carboxamide in soil is estimated to be 360 days (8640 hrs). Based on this half-life value of N-(4-chlorophenyl)-3-hydroxy-4-[(E)-2-(2-methyl-5-nitrophenyl)diazen-1-yl]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 N-(4 -chlorophenyl)-3 -hydroxy-4 -[(E)-2 -(2 -methyl-5 -nitrophenyl)diazen-1 -yl]naphthalene-2 -carboxamide can be considered to be not readily biodegradable in nature.