Registration Dossier

Administrative data

Endpoint:
hydrolysis
Type of information:
experimental study
Adequacy of study:
key study
Study period:
30 Sep 2015
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
guideline study with acceptable restrictions

Data source

Referenceopen allclose all

Reference Type:
study report
Title:
Unnamed
Year:
2016
Report Date:
2016
Title:
Unnamed
Year:
2017
Report Date:
2017

Materials and methods

Test guidelineopen allclose all
Qualifier:
according to
Guideline:
OECD Guideline 111 (Hydrolysis as a Function of pH)
Qualifier:
according to
Guideline:
EU Method C.7 (Degradation: Abiotic Degradation: Hydrolysis as a Function of pH)
GLP compliance:
no
Remarks:
Preliminary test

Test material

Reference
Name:
Unnamed
Type:
Constituent
Radiolabelling:
no

Study design

Analytical monitoring:
yes
Details on sampling:
- Sampling method: Aliquots (100 μL) of a stock solution of the test item in acetonitrile (10 g/l) were added to vials containing buffer solution (10 mL), which had been purged with nitrogen and pre-equilibrated at test temperature (50 °C) in a water bath. This produced test solutions of nominal concentration 100 mg/L. One pair of samples was processed for analysis immediately, whilst another pair was returned to the water bath for 10 minutes prior to processing. On both occasions, the entire volume of each sample was extracted with chloroform (10 mL) and the extract analysed directly by gas chromatography (GC).
Buffers:
pH 4.0 : Potassium dihydrogen orthophosphate (3.00 g) and disodium hydrogen orthophosphate dodecahydrate (6.40 g) were dissolved in purified water (950 ml) and the pH was adjusted to 4.0 ± 0.05 with orthophosphoric acid. The volume was then adjusted to 1000 ml with purified water.pH 7.0 : Potassium dihydrogen orthophosphate (6.80 g) was dissolved in purified water (950 ml), 1M sodium hydroxide (30 ml) was added and the pH was adjusted to 7.0 ± 0.05 with 1M hydrochloric acid. The volume was then adjusted to 1000 ml with purified water.pH 9.0 : Disodium tetraborate decahydrate (16.6 g) and potassium dihydrogen orthophosphate (1.80 g) were dissolved in purified water (950 ml) and the pH was adjusted to 9.0 ± 0.05 with 1M hydrochloric acid.. The volume was then adjusted to 1000 ml with purified water.
Duration of testopen allclose all
Duration:
10 min
pH:
4
Temp.:
50 °C
Initial conc. measured:
88.7 mg/L
Duration:
10 min
pH:
7
Temp.:
50 °C
Initial conc. measured:
92.1 mg/L
Duration:
10 min
pH:
9
Temp.:
50 °C
Initial conc. measured:
82.4 mg/L
Number of replicates:
2 replicates
Positive controls:
no
Negative controls:
no

Results and discussion

Preliminary study:
Preliminary investigationThe preliminary study showed that at pH 4, 7 and 9 and 50 ± 0.5 °C, greater than 50% hydrolysis had occurred after 10 minutes, indicating a half-life of significantly less than 1 day under environmental conditions (25 °C).Degradation productDegrdation product was detected by GC Analysis after the extraction treatment of the test solution. The chemical structure of this product is not determined. pH of test solutionsThe pH values showed that there was no significant change in pH of the buffer solutions after addition of the test substance, indicating that the test systems were close to nominal pH.
Transformation products:
not measured
Remarks:
expert statement (Javier CUESTA-PÉREZ, 2017)
Identity of transformation products
No.:
#1
Reference
Reference substance name:
Unnamed
IUPAC name:
Carbonylbis(azanediyl-2-methylpropane-2,1,3-triyl) tetraprop-2-enoate
Identifier:
common name
Identity:
N,N’-Di(1,1-bis(acryloyloxymethyl)ethyl)urea
CAS number:
n.a
Molecular formula:
C21H28N2O9
Molecular weight:
452.455
SMILES notation:
O=C(C=C)OCC(C)(COC(=O)C=C)NC(=O)NC(C)(COC(=O)C=C)COC(=O)C=C
InChl:
InChI=1S/C21H28N2O9/c1-7-15(24)29-11-20(5,12-30-16(25)8-2)22-19(28)23-21(6,13-31-17(26)9-3)14-32-18(27)10-4/h7-10H,1-4,11-14H2,5-6H3,(H2,22,23,28)
Dissipation DT50 of parent compoundopen allclose all
pH:
4
Temp.:
25 °C
DT50:
< 1 d
Type:
not specified
pH:
7
Temp.:
25 °C
DT50:
< 1 d
Type:
not specified
pH:
9
Temp.:
25 °C
DT50:
< 1 d
Type:
not specified

Any other information on results incl. tables

CONCLUSION

The test item was determined to be hydrolytically unstable under acidic, neutral and basic conditions.

Table 1: Preliminary investigation results for hydrolysis of the test item

pH

Ct (mg/l)

 

t0min

t10min

 

Measured

Mean

Measured

Mean

4

85.3, 92.0

88.7

17.9, 18.1

18.0

7

94.7, 89.5

92.1

5.1, 6.2

5.7

9

77.5, 87.2

82.4

2.1, 2.8

2.4

 

Applicant's summary and conclusion

Conclusions:
The test item was determined to be hydrolytically unstable under acidic, neutral and basic conditions. The most probable outcome of the hydrolysis of the test item is the stable urea derivate, Carbonylbis(azanediyl-2-methylpropane-2,1,3-triyl) tetraprop-2-enoate (CUESTA-PÉREZ, J., 2017).