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Biodegradation in water

Biodegradability of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (CAS no. 52320 -66 -8) is predicted using QSAR toolbox version 3.3 (2017) with logKow as the primary descriptor. Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide was estimated to be not readily biodegradable in water.

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 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl) diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The bioconcentration factor (BCF) of 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide 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 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3-oxobutanamide 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 2 -[(E)-2 -(4 -chloro-2 -nitro phenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The soil adsorption coefficient i.e Koc value of 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide was estimated to be 1108 L/kg (log Koc=3.0445) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide has a moderate sorption to soil and sediment and therefore have slow migration potential to ground water.

Additional information

Biodegradation in water

Various predicted data for the target compound 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide(CAS No. 52320-66-8) 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 3.3 with logKow as the primary descriptor, percentage biodegradability of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4-ethoxyphenyl)-3-oxobutanamide(CAS No. 52320-66-8) was estimated.Test substance undergoes 5.3% degradation by BOD in 28 days. Thus, based on percentage degradation, the test chemical2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamidewas 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 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide(CAS No. 52320-66-8) 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 chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3-oxobutanamideis expected to be not readily biodegradable.

 

In a supporting weight of evidence study from authoritative database (J-CHECK & HSDB, 2017 and EnviChem, 2014) for the read across chemical 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl) didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) (CAS no. 6358-85-6),biodegradation experiment was conducted for 14 days for evaluating the percentage biodegradability of read across substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide). The study was performed according to OECD Guideline 301 C (Ready Biodegradability: Modified MITI Test (I)). 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 2,2'-[(3,3'-dichlorobiphenyl- 4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) was determined to be 0% by BOD parameter in 14 days. Thus, based on percentage degradation, 2,2'-[(3,3'-dichloro biphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) is considered to be not readily biodegradable in nature.

 

Another biodegradation study was conducted for 14 days for evaluating the percentage biodegradability of test substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) (CAS no. 6358-85-6) (OECD SIDS, 2003). 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. 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 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenylbutanamide) was determined to be 0% by BOD and UV-Vis parameter in 14 days. Thus, based on percentage degradation, 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) is considered to be not readily biodegradable in nature.

 

On the basis of above results for target chemical2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide(from OECD QSAR toolbox version 3.3 and EPI suite, 2017) and for its read across substance (from authoritative database J-CHECK, HSDB & EnviChem and secondary source OECD SIDS), it can be concluded that the test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamidecan be expected to be not readily biodegradable in nature.

Bioaccumulation: aquatic / sediment

Various predicted data for the target compound 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (CAS No. 52320-66-8) 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 aprediction done using the BCFBAF Program(v3.01) of Estimation Programs Interface (EPI Suite, 2017) was used to predict the bioconcentration factor (BCF) of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The bioconcentration factor (BCF) of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide 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 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3-oxobutanamide 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), theBio-concentration Factor (BCF) of the test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (CAS no. 52320 -66 -8) was estimated to be 8897, 11660, 12007, 11778, 9645, 3446, 496, 86.8, 44.2, 40.0, 39.5, 39.3 and 38.1 at pH range 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10-12, 13 and 14, respectively. This value (86.8 at pH 7.0) indicates that the test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was considered to be non-accumulative in aquatic organisms.

 

Bioconcentration Factor (BCF) of test chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated using Chemspider database(ChemSpider, 2017). The bioconcentration factor of test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 489.98 at pH 5.5 and 4.10 at pH 7.4, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.

 

Another predicted data was estimated using Scifinder database (American Chemical Society (ACS), 2017) was used for predicting the bioconcentration factor (BCF) of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The bioconcentration factor (BCF) of 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 3290, 3400, 3410, 3350, 2860, 1170, 178, 28.4, 12.6 and 11.0 (at 25 deg C) at pH range 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10, respectively which does not exceed the bio concentration threshold of 2000 at pH 7.0, indicating that the chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide 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 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated to be 52.9 dimensionless . The predicted BCF result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide is non-bioaccumulative in nature.

 

In a supporting weight of evidence study from authoritative database (J-CHECK & HSDB, 2017 and EnviChem, 2014) and secondary source (OECD SIDS, 2003) for the read across chemical 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) (CAS no. 6358-85-6), bioaccumulation experiment was conducted on test organism Cyprinus carpio for 6 weeks for evaluating the bioconcentration factor (BCF value) of 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) (CAS no. 6358-85-6).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 0.1mg/l and 0.01 mg/l, respectively. Test chemical solution was prepared in HCO-40 or crystal sugar. Analytical method involve therecovery ratio:Test water : 1st concentration area : 94.2 %, 2nd concentration area : 100 %, Fish : 80.7 %, - Limit of detection : Fish : 0.0186 ppm. Range finding study involve the TLm (48 hr) ≥ 420 mg/l (w/v) on Rice fish (Oryzias latipes). Lipid content of the test organism was determined to be 2.8%. The bioconcentration factor (BCF value) of substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) on Cyprinus carpio was determined to be in the range of 0.38 – 3.2 L/Kg at a conc. of 0.1 mg/l and 2.4 – 5.4 L/Kg at a conc. of 0.01 mg/l, respectively, which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) is not expected to bioaccumulate in the food chain.

 

On the basis of above results for target chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (from EPI suite, ACD labs,ChemSpider, SciFinder database and CompTox Chemistry Dashboard,  2017) and for its read across substance (from authoritative database and secondary source), it can be concluded that the BCF value of test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide ranges from 4.10 – 178 which does not exceed the bioconcentration threshold of 2000, indicating that the chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide is not expected to bioaccumulate in the food chain.

 

Adsorption / desorption

Various predicted data for the target compound 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (CAS No. 52320-66-8) 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 2 -[(E)-2 -(4 -chloro-2 -nitro phenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The soil adsorption coefficient i.e Koc value of 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide was estimated to be 1108 L/kg (log Koc=3.0445) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide has a moderate sorption to soil and sediment and therefore have slow migration potential to ground water.

 

The Soil Adsorption Coefficient i.e Koc value of test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 21215, 27803, 28631, 28086, 22999, 8217, 1184, 207, 105, 95.3, 94.2, 94.1, 93.8 and 90.9 at pH range 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11-12, 13 and 14, respectively (log Koc ranges from 2.0 ± 1.0 to 4.5 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017). This Koc value (207 at pH 7.0) indicates that the test substance 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide has a low sorption to soil and therefore have moderate migration potential to groundwater.

 

In an another prediction done by usingSciFinder database (American Chemical Society (ACS), 2017), the soil adsorption coefficient i.e Koc value of test chemical 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide (CAS No. 52320 -66 -8). The soil adsorption coefficient i.e Koc value of 2 -[(E)-2 -(4 -chloro-2 -nitrophenyl)diazen-1 -yl]-N-(4 -ethoxyphenyl)-3 -oxobutanamide was estimated to be 11300, 11700, 11500, 9860, 4040, 615, 97.7, 43.3 and 37.9 at pH range 1, 2 -3, 4, 5, 6, 7, 8, 9 and 10, respectively (log Koc value ranges from 1.578 to 4.05) (at 25 deg C). This Koc value (615 at pH 7.0) indicates that the substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide has a moderate sorption to soil and sediment and therefore have slow migration potential to ground water.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) (CAS no. 6358-85-6),adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1 -diyl]bis(3 -oxo-N-phenyl butanamide). The adsorption coefficient (Koc) value was calculated using an estimated logKow and a regression derived equation. The adsorption coefficient (Koc) value of substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) was estimated to be 67 (Log Koc = 1.826). This Koc value indicates that the substance 2,2'-[(3,3'-dichlorobiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(3-oxo-N-phenylbutanamide) has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

On the basis of above overall results for target chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide (from EPI suite, ACD labs andSciFinder database,2017) and for its read across substance (from authoritative database HSDB, 2017), it can be concluded that the Koc value of test substance 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamideranges from 207–1108 (at pH 7.0) indicating that the test chemical 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide has a low to moderate sorption to soil and sediment and therefore have moderate to slow migration potential to ground water.