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Registration Dossier
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EC number: 266-257-8 | CAS number: 66215-27-8
Hydrolysis
Administrative data
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- 1979/04/12 to 1979/05/10
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- test procedure in accordance with national standard methods with acceptable restrictions
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 1 979
- Report date:
- 1979
Materials and methods
Test guideline
- Qualifier:
- equivalent or similar to guideline
- Guideline:
- other: Pesticide Assessment Guidelines, Subdivision N, Chemistry: Environmental Fate ; 161-1 Hydrolysis studies. U.S. Environmental Protection Agency
- Version / remarks:
- 18 Oct 1982
- Deviations:
- yes
- Remarks:
- minor
- GLP compliance:
- no
- Remarks:
- GLP not formally adopted at the time of the study. Study was performed according to sound scientific practices.
Test material
- Reference substance name:
- N-cyclopropyl-1,3,5-triazine-2,4,6-triamine
- EC Number:
- 266-257-8
- EC Name:
- N-cyclopropyl-1,3,5-triazine-2,4,6-triamine
- Cas Number:
- 66215-27-8
- Molecular formula:
- C6H10N6
- IUPAC Name:
- N2-cyclopropyl-1,3,5-triazine-2,4,6-triamine
Constituent 1
- Radiolabelling:
- yes
- Remarks:
- [U-14C]triazine labelled cyromazine
Study design
- Analytical monitoring:
- yes
- Details on sampling:
- After various time intervals ranging from 0 to 28 days, samples were removed and analysed as described below.
Aliquots of the hydrolysis solutions at different time intervals were diluted with the same volume of ethanol. - Buffers:
- Buffer 1:
Phthalate buffer, pH 5.00 ± 0.01
0.1 M potassium hydrogen
phthalate + 0.05 M NaOH
Buffer 2:
Phosphate buffer, pH 7.00 ± 0.01
0.041 M Na2HPO4+
0.028 M KH2PO4
Buffer 3:
Borate buffer, pH 9.00 ± 0.02
0.043 M borax +
0.017 M KH2PO4 - Details on test conditions:
- Solutions of 100 ppm 14C-ring labelled cyromazine were prepared in the following aqueous solutions : 0.1N HCl, 0.1N NaOH and buffered solutions of pH 5, 7 and 9, respectively.
An automatic pipette was used to fill 50 cm3 Erlenmeyer flasks with 30 cm3 each of these solutions. After closing the flasks with glass stoppers and suitable clamps, they were kept in thermostatically controlled water-bath shakers at 30.0, 50.0 and 70.0 °C) (shaking frequency = 150 r.p.m.).
Duration of testopen allclose all
- Duration:
- 28 d
- pH:
- 9
- Temp.:
- 70 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 9
- Temp.:
- 50 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 9
- Temp.:
- 30 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 7
- Temp.:
- 70 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 7
- Temp.:
- 30 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 5
- Temp.:
- 70 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 5
- Temp.:
- 50 °C
- Initial conc. measured:
- 100 mg/L
- Duration:
- 28 d
- pH:
- 5
- Temp.:
- 30 °C
- Initial conc. measured:
- 100 mg/L
- Number of replicates:
- not stated
- Positive controls:
- no
- Negative controls:
- no
- Statistical methods:
- The rate constants and half-lives were calculated using the equation:
k(rate) [s-1] = lnc0-lnc/t
t0.5 [h] = ln2/3600xk(rate)
c0 = initial concentration
c = concentration at time t
3600 = conversion factor (1h is equal to 3600s)
Results and discussion
- Preliminary study:
- No preliminary study identified.
- Transformation products:
- yes
Identity of transformation productsopen allclose all
- No.:
- #2
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- 6-(cyclopropylamino)-1H-1,3,5-triazine-2,4-dione
- Molecular formula:
- C6H8N4O2
- Molecular weight:
- 168.15
- SMILES notation:
- C1CC1NC2=NC(=O)NC(=O)N2
- InChl:
- 1S/C6H8N4O2/c11-5-8-4(7-3-1-2-3)9-6(12)10-5/h3H,1-2H2,(H3,7,8,9,10,11,12)
- No.:
- #1
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- 6-amino-4-(cyclopropylamino)-1H-1,3,5-triazin-2-one
- CAS number:
- 92510-62-8
- Molecular formula:
- C6H9N5O
- Molecular weight:
- 167.17
- SMILES notation:
- C1CC1NC2=NC(=O)NC(=N2)N
- InChl:
- 1S/C6H9N5O/c7-4-9-5(8-3-1-2-3)11-6(12)10-4/h3H,1-2H2,(H4,7,8,9,10,11,12)
- Details on hydrolysis and appearance of transformation product(s):
- Hydrolysis in the acidic solutions (0.1N HCl):
Cyromazine - 16%
2-amino-4-cyclopropylamino-6-hydroxy-s- triazine - 76%
Hydrolysis in the alkaline solutions (0.1N NaOH):
Cyromazine - 79%
2-amino-4-cyclopropylamino-6-hydroxy-s- triazine - 9%
2—cyclopropylamino—4,6-dihydroxy—s—triazine - 4%
Total recovery of test substance (in %)open allclose all
- % Recovery:
- 99
- pH:
- 9
- Duration:
- 28 d
- % Recovery:
- 99
- pH:
- 7
- Duration:
- 28 d
- % Recovery:
- 99
- pH:
- 5
- Duration:
- 28 d
Dissipation DT50 of parent compound
- Remarks on result:
- other: No hydrolysis, DT50 not measurable
- Other kinetic parameters:
- In O.1N HCl, half-lives for cyromazine were calculated to be 7.7 days at 70°C and 106 days at 50°C. At 70°C cyromazine hydrolyzed in O.1N NaOH with a half-life of 80 days.
- Details on results:
- No significant hydrolysis of 14C-cyromazine occurred at pH 5, 7, 9 at three different temperatures of 30, 50 and 70 °C over a period of 28 days.
Some hydrolysis was observed in 0.1 N hydrochloric acid and in 0.1 N sodium hydroxide solutions at 50 and 70°C to 2-amino-4-cyclopropylamino-6-hydroxy-s- triazine.
Applicant's summary and conclusion
- Validity criteria fulfilled:
- not specified
- Conclusions:
- No significant hydrolysis of cyromazine occurred at pH 5, 7 and 9 at three different temperatures (70, 50 and 30°C) over a period of 28 days.
- Executive summary:
The chemical hydrolysis of cyromazine in different aqueous media with pH values ranging from 1 to 13 and at a concentration of 100 ppm was investigated.
No significant hydrolysis of cyromazine occurred at pH 5, 7 and 9 at three different temperatures (70, 50 and 30°C) over a period of 28 days. In 0.1N HCl, cyromazine was hydrolyzed at 50°C and 70°C with half-lives of 106 and 7.7 days, respectively. At 70°C the half-life of cyromazine in 0.1N NaOH was found to be 80 days.
Under acidic conditions, the main hydrolysis product was the 2-amino-4-cyclopropylamino-G-hydroxy-s-triazine. Under alkaline conditions, besides compound mentioned before also 2-cyclopropyl-amino-4,6-dihydroxy-s-triazine was formed.
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