Registration Dossier

Administrative data

Endpoint:
other distribution data
Type of information:
experimental study
Adequacy of study:
key study
Study period:
1985
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Data from peer-reviewed handbook or collection of data; comparable to guideline study with acceptable restrictions

Data source

Reference
Reference Type:
study report
Title:
Unnamed
Year:
1985
Report Date:
1985

Materials and methods

Principles of method if other than guideline:
The mobilities of (2-ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate and its three major soil degradates, its initial hydrolysis product, lactyl-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate (aerobic), its second hydrolysis product, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (aerobic) and its reduction product, 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid (anaerobic), in soil were examined in relation to their potential to be leached by water using thin layer chromatography on 6 soils.
GLP compliance:
not specified
Type of study:
soil leaching
Media:
water - soil

Test material

Reference
Name:
Unnamed
Type:
Constituent
Test material form:
solid: particulate/powder
Remarks:
migrated information: particulates
Details on test material:
Radioactive Chemicals
14C-(2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate, uniformly labelled 14C in benzoic acid ring, 4 mCi/mmole, in acetone, 11.6 µg/µL, approximately 0.22 Mio. dpm/µL, for tests with Altvan, Hanford and Muscatine soils, > 98% purity.

14C-(2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate obtained from California Bionuclear, uniformly labelled 14c in benzoic acid ring, 195mCi/mmole, in methanol, 1.2 µg/µL, approximately 0.11 Mio. dpm/µL, for tests with Kibbie and Ritzsville soils, > 9S% C purity.

14C Atrazine from Pathfinder, uniformly labelled 14C ring labelled 58.3 mCi/mmole, in ethyl acetate, 1.3 µg/µL 1.1 x 10 dpm/µL, depending of type of experiment, purity of 83.5% increased by purification to 91.1%

5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid California Bionuclear, 419 mCi/mmole in methanol, 0.685 mg/mL, 8.43 x 10 dpm/µl

lactyl-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate 19 mCi/mmole, uniformly labelled 14C in benzoic acid ring, in methanol, 1.12 mg/mL, 0.11 Mio. dpm/µL

5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid, 14CF3 labelled, specific activity 7.20 mCi/mo1e, purified by TCC before use

Soils
(Characterization see below)
- Runford Series Soil
- Ritzsville Series Soil
- Altvan Series soil
- Wooster Series Soil
- Muscatine Series Soil
- Kibbie Series Soil

Results and discussion

Any other information on results incl. tables

On all soils, 2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate was highly immobile with Rf values of almost 0. Rf values ranging from 0.13 to 0.91 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl lactic acid, 0.31 to ca. 1 for 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, and 0.08 to 0.62 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid, suggested that mobility of the degradates was significantly greater than the parental (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate. Rfvalues correlated fairly to well with soil organic matter, ranging from 0.480 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl lactic acid, to 0.878 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid.

Applicant's summary and conclusion

Conclusions:
2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate is highly immobile in soil, whereas its degradation products, 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl lactic acid (aerobic), 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (aerobic) and 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid are more mobile, the mobility increasing with polarity.

Executive summary:

The mobility of (2-ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate and its three major soil degradates, its initial hydrolysis product, 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl lactic acid (aerobic), its second hydrolysis product, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid (aerobic) and its reduction product, 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid (anaerobic) in soil was examined in relation to its potential to be leached by water.

Thin layer chromatography was performed using six soils from different geographical locations, with an organic matter content between 0.43 and 2.6% w/w of the soil, as the stationary phase. On all soils, (2 -ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate was highly immobile with Rf values of almost 0. Rf values ranging from 0.13 to 0.91 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl lactic acid, 0.31 to ca. 1 for 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid, and 0.08 to 0.62 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid, suggested that mobility of the degradates was greater than that of the parental (2-ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate in the soil/water system. Rf values correlated fairly to well with soil organic matter, ranging from 0.480 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl lactate, to 0.878 for 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid, the anaerobic degradation product. The order of mobility was 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid > 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-amino benzoic acid > 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl lactic acid > (2-Ethoxy-1-methyl-2-oxoethyl)-5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate, with the parental substance being the less mobile of the tested substances.