2-[(4-chloro-2-nitrophenyl)azo]-N-(4-ethoxyphenyl)-3-oxobutyramide

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption

Remarks:

adsorption

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

weight of evidence

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

accepted calculation method

Justification for type of information:

Estimated data generated using the EPI Suite model developed by the USEPA.

Qualifier:

according to guideline

Guideline:

other: Modeling database

Principles of method if other than guideline:

Prediction done using KOCWIN Program (v2.00)

GLP compliance:

not specified

Type of method:

other: MCI Method

Media:

soil

Specific details on test material used for the study:

- Name of test material (IUPAC name): 2-[(E)-2-(4-chloro-2-nitrophenyl)diazen-1-yl]-N-(4-ethoxyphenyl)-3-oxobutanamide
- Molecular formula: C18H17ClN4O5
- Molecular weight: 404.808 g/mol
- Smiles notation: O=C(Nc1ccc(OCC)cc1)[C@@H](\N=N\c1c([N+](=O)[O-])cc(cc1)Cl)C(=O)C
- InChl: 1S/C18H17ClN4O5/c1-3-28-14-7-5-13(6-8-14)20-18(25)17(11(2)24)22-21-15-9-4-12(19)10-16(15)23(26)27/h4-10,17H,3H2,1-2H3,(H,20,25)/b22-21+
- Substance type: Organic
- Physical state: Solid

Radiolabelling:

not specified

Test temperature:

25 deg.C

Analytical monitoring:

not specified

Key result

Type:

Koc

Value:

1 108 L/kg

Temp.:

25 °C

Remarks on result:

other: Log Koc= 3.0445 (estimated by MCI method)

Transformation products:

not specified

KOCWIN Program (v2.00) Results:

==============================

SMILES : O=C(Nc2ccc(OCC)cc2)C(N=Nc1c(N(=O)(=O))cc(cc1)CL)C(=O)C

CHEM :

MOL FOR: C18 H17 CL1 N4 O5

MOL WT : 404.81

--------------------------- KOCWIN v2.00 Results ---------------------------

Koc Estimate from MCI:

---------------------

First Order Molecular Connectivity Index ........... : 13.312

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 7.5392

Fragment Correction(s):

1 Nitrogen to non-fused aromatic ring ... : -0.5225

1 Ether, aromatic (-C-O-C-) ........... : -0.6791

1 Nitro (-NO2) ......................... : -0.4889

1 N-CO-C (aliphatic carbon) ............ : -1.0277

1 Ketone (-C-CO-C-) ................... : -1.1290

1 Azo (-N=N-) ......................... : -0.6475

Corrected Log Koc .................................. : 3.0445

Estimated Koc: 1108 L/kg <===========

Validity criteria fulfilled:

not specified

Conclusions:

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.

Executive summary:

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.

Description of key information

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.

Key value for chemical safety assessment

Koc at 20 °C:

1 108

Additional information

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.

[LogKoc: 3.0445]