3,4-dicyanoaniline

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 : 4-aminobenzene-1,2-dicarbonitrile
- Common name : 3,4-dicyanoaniline
- Molecular formula : C8H5N3
- Molecular weight : 143.148 g/mol
- Smiles notation : N#Cc1c(C#N)ccc(N)c1
- InChl : 1S/C8H5N3/c9-4-6-1-2-8(11)3-7(6)5-10/h1-3H,11H2
- Substance type : Organic
- Physical state : Solid

Radiolabelling:

not specified

Test temperature:

25 deg.C

Analytical monitoring:

not specified

Key result

Type:

Koc

Value:

31 L/kg

Temp.:

25 °C

Remarks on result:

other: Log Koc= 1.4914 (estimated by MCI method)

Transformation products:

not specified

KOCWIN Program (v2.00) Results:

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

SMILES : C(#N)c(c(C(#N))ccc1N)c1

CHEM : 1,2-Benzenedicarbonitrile, 4-amino-

MOL FOR: C8 H5 N3

MOL WT : 143.15

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

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 5.274

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 3.3493

Fragment Correction(s):

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

2 Nitrile/Cyanide (-C#N) ............... : -1.3354

Corrected Log Koc .................................. : 1.4914

Estimated Koc: 31 L/kg <===========

Validity criteria fulfilled:

not specified

Conclusions:

The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 31 L/kg (log Koc=1.4914) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a negligible sorption to soil and sediment and therefore have rapid 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 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 31 L/kg (log Koc=1.4914) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a negligible sorption to soil and sediment and therefore have rapid 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 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 31 L/kg (log Koc=1.4914) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a negligible sorption to soil and sediment and therefore have rapid migration potential to ground water.

Key value for chemical safety assessment

Koc at 20 °C:

31

Additional information

Various predicted data for the target compound 4-aminobenzene-1,2-dicarbonitrile(CAS No. 56765-79-8) 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 4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8). The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 31 L/kg (log Koc=1.4914) by means of MCI method (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a negligible sorption to soil and sediment and therefore have rapid migration potential to ground water.

 

The Soil Adsorption Coefficient i.e Koc value of test substance 4-aminobenzene-1,2-dicarbonitrile (CAS no. 56765 -79 -8) was estimated using Adsorption Coefficient module (v12.1.0.50374) program as Koc 58, 97.3, 104 and 105  at pH range 0, 1, 2 and 3-14, respectively (log Koc value ranges from 1.8 ± 1.0 to 2.0 ± 1.0)(ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017).This Koc value indicates that the test substance has a low sorption to soil and therefore have moderate 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 4-aminobenzene-1,2-dicarbonitrile(CAS no. 56765 -79 -8) was estimated. The adsorption coefficient (Koc) value of test substance 4-aminobenzene-1,2-dicarbonitrile was estimated to be 90.34 (Log Koc = 1.9558) at both pH 5.5 and 7.4, respectively. This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a low sorption to soil and sediment and therefore have moderate migration potential to groundwater.

 

Additional soil adsorption coefficient i.e Koc value of test chemical4-aminobenzene-1,2-dicarbonitrile (CAS No. 56765 -79 -8)was estimated using the SciFinder database (American Chemical Society (ACS), 2017).The soil adsorption coefficient i.e Koc value of 4-aminobenzene-1,2-dicarbonitrile was estimated to be 48.4, 51.9 and 52.3 at pH range 1, 2, and 3-10, respectively (log Koc value ranges from 1.6848 to 1.718) (at 25 deg C). This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a low sorption to soil and sediment and therefore have moderate 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 4-aminobenzene-1,2-dicarbonitrile was estimated to be 55.5 L/kg (log Koc = 1.7442).The predicted KOC result based on the 5 OECD principles. This Koc value indicates that the substance 4-aminobenzene-1,2-dicarbonitrile has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

In a supporting weight of evidence study from authoritative database (HSDB, 2017) for the read across chemical 1,2-Dicyanobenzene (CAS no. 91-15-6),adsorption experiment was conducted for estimating the adsorption coefficient (Koc) value of read across chemical 1,2-Dicyanobenzene. The adsorption coefficient (Koc) value was calculated using a logKow of 0.99 and a regression derived equation. The adsorption coefficient (Koc) value of substance 1,2-Dicyanobenzene was estimated to be 82 (Log Koc = 1.9138). This Koc value indicates that the substance 1,2-Dicyanobenzene has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

For the read across chemical 3,4-dimethylaniline (CAS no. 95-64-7),adsorption study was conducted for estimating the adsorption coefficient (Koc) value of test chemical 3,4-dimethylaniline (HSDB, 2017).The adsorption coefficient (Koc) value was calculated using a logKow of 1.84 and a regression derived equation. The adsorption coefficient (Koc) value of read across substance 3,4-dimethylaniline was estimated to be 240 (Log Koc = 2.38). This Koc value indicates that the substance 3,4 -dimethylaniline has a low sorption tosoil and sediment and therefore have moderate migration potential to ground water.

 

On the basis of above overall results for target chemical 4-aminobenzene-1,2-dicarbonitrile(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 substance 4-aminobenzene-1,2-dicarbonitrile ranges from 31–105indicating that the test chemical 4-aminobenzene-1,2-dicarbonitrile has a negligible to low sorption to soil and sediment and therefore have rapid to moderate migration potential to ground water.

 

[LogKoc: 1.4914]