1-(N,N-bis(2-ethylhexyl)aminomethyl)-1,2,4-triazole

Hydrolysis

Link to relevant study record(s)

Reference

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

key study

Study period:

June 2009

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

comparable to guideline study

Remarks:

For this study no standard guideline is available but study was performed according to GLP.

Qualifier:

no guideline followed

Principles of method if other than guideline:

The decomposition of the test item in water or in mixtures of organic solvents and water is very fast and therefore its hydrolysis parameters cannot be determined according to OECD Guideline TG111 (“Hydrolysis as a Function of pH”). Therefore, this study was subdivided into two parts:

- Investigations on the test item and hydrolysis products by LC/MS with an aqueous/organic mobile phase.
- NMR investigations on the test item in an organic solvent and in mixtures of this organic solvent and water.

GLP compliance:

yes (incl. QA statement)

Radiolabelling:

no

Analytical monitoring:

yes

Positive controls:

no

Negative controls:

no

Preliminary study:

The purpose of this study was to show that the test item hydrolyses in water very quickly. Therefore, two different sets of experiments have been performed:
 
Investigations by LC/MS
Investigations by 1H-NMR

Transformation products:

yes

No.:

#1

No.:

#2

No.:

#3

Key result

Remarks on result:

not determinable because of methodological limitations

Details on results:

Investigations by LC/MS:

Introduction of the test item in organic solvent into a HPLC-MS system leads to only one sharp peak in the chromatogram, which is identical to the reference solution of the degradation product bis(2-ethylhexyl)amine. This proves that the test item hydrolyses almost instantly, when it comes into contact with the aqueous eluent of the HPLC.
 
Investigations by 1H-NMR:

Solutions of the test item in pure acetonitrile and in mixtures of acetonitrile and water at different ratios and after different times have been analyzed by 1H-NMR. The experiments prove that hydrolysis of the test item, even with small amounts of water, is very fast. A stable equilibrium is formed within one hour. The degradation products are clearly identified.
 
In nature, where the test item would come into contact with a billion-fold excess of water, immediate hydrolysis will occur

Conclusions:

The substance EC 401-280-0 hydrolyses in contact with water almost immediately. The identified hydrolyses products are formaldehyde, bis(2-ethylhexylamine) and 1H-1,2,4-triazole.

Description of key information

The substance EC 401-280-0 hydrolyses in contact with water almost immediately. The identified hydrolyses products are formaldehyde, bis(2-ethylhexylamine) and 1H-1,2,4-triazole.

Hydrolysis of formaldehyde and bis(2-ethylhexyl)amine is not expected due to their chemical structure. The hydrolysis half-life of 1H-1,2,4-triazole is > 30days.

Additional information

Parent substance EC 401 -280 -0

The results of the Hydrolysis study (Ciba, 2009) show that the test item hydrolyses rapidly in water. The identified degradation products are bis(2-ethylhexyl)amine, 1H-1,2,4-triazole and formaldehyde. The study includes two sets of experiments:

1st experiment: Investigation by LC/MS showed one sharp peak which is identical with a degradation product of the test item. This proves that the test item hydrolyses almost instantly, when it comes into contact with the aqueous eluent of the HPLC.

2nd experiment: Investigation by H-NMR showed that solutions of the test item are stable in pure acetonitrile for at least 20 h. Immediately after addition of D2O degradation products of the test item occured. The experiments prove that hydrolysis of test item, even with small amounts of water, is very fast.

hydrolysis products:

bis(2 -ethyhexyl)amine

The structure of the substance does not contain any functional groups sensitive to hydrolysis

Formaldehyde

Hydrolysis is not expected

1H-1,2,4 -triazole

Data with 1,2,4-triazole show that hydrolysis half-life was not observed during 30 days, therefore the half-life is > 30days.