Benzamide, N-[[4-[(cyclopropylamino)carbonyl]phenyl]sulfonyl]-2-methoxy-

Biodegradation in soil

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

supporting study

Study period:

03 Feb 2004 - 04 May 2006

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

other: US EPA Subdivision N, Section 162-1

Qualifier:

according to guideline

Guideline:

other: Canada PMRA DACO Number 8.2.3.4.2

GLP compliance:

yes (incl. QA statement)

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

aerobic

Soil classification:

USDA (US Department of Agriculture)

Soil no.:

#1

Soil type:

silt loam

% Clay:

16

% Silt:

66

% Sand:

18

% Org. C:

1.8

pH:

6.7

CEC:

13.3 meq/100 g soil d.w.

Bulk density (g/cm³):

1.08

Soil no.:

#2

Soil type:

loam

% Clay:

21

% Silt:

35

% Sand:

44

% Org. C:

0.9

pH:

7.2

CEC:

9.5 meq/100 g soil d.w.

Bulk density (g/cm³):

1.19

Soil no.:

#3

Soil type:

loamy sand

% Clay:

6

% Silt:

18

% Sand:

76

% Org. C:

2.3

pH:

6.3

Soil no.:

#4

Soil type:

loamy sand

% Clay:

5

% Silt:

19

% Sand:

76

% Org. C:

1.1

pH:

5.9

CEC:

10 meq/100 g soil d.w.

Bulk density (g/cm³):

1.11

Details on soil characteristics:

COLLECTION AND STORAGE
- Geographic location: Seven test soils were used in this study:
• AXXa (LaacherHof, Field Plot 'AXXa') origin EU
• Alll (Laacher Hof, Field Plot'AM') origin EU
• HAH (Hoefchen am Hohenseh, Field Plot '4A') origin EU
• PKV (Pikeville Loamy Sand) origin US

- Collection procedures: Field sampled with showel into pot
- Sampling depth (cm): 0 - 20 cm
- Storage conditions: 4 °C refrigerator
- Storage length: differ from soil to soil
- Soil preparation: The soils were sieved to < 2 mm particle size and air-dried at ambient temperature.

Soil No.:

#1

Duration:

120 d

Soil No.:

#2

Duration:

120 d

Soil No.:

#3

Duration:

120 d

Soil No.:

#4

Duration:

365 d

Soil No.:

#1

Initial conc.:

0.427 mg/kg soil d.w.

Based on:

test mat.

Soil No.:

#2

Initial conc.:

0.427 mg/kg soil d.w.

Based on:

test mat.

Soil No.:

#3

Initial conc.:

0.427 mg/kg soil d.w.

Based on:

test mat.

Soil No.:

#4

Initial conc.:

0.072 mg/kg soil d.w.

Based on:

test mat.

Soil No.:

#1

Initial conc.:

160 g/ha d.w.

Based on:

test mat.

Soil No.:

#2

Initial conc.:

160 g/ha d.w.

Based on:

test mat.

Soil No.:

#3

Initial conc.:

160 g/ha d.w.

Based on:

test mat.

Soil No.:

#4

Initial conc.:

160 g/ha d.w.

Based on:

test mat.

Parameter followed for biodegradation estimation:

radiochem. meas.

Soil No.:

#1

Temp.:

20 ± 1 °C

Microbial biomass:

631 µg microbial C/g soil (Initial Biomass)

Soil No.:

#2

Temp.:

20 ± 1 °C

Microbial biomass:

239 µg microbial C/g soil (Initial Biomass)

Soil No.:

#3

Temp.:

20 ± 1 °C

Microbial biomass:

481 µg microbial C/g soil (Initial Biomass)

Soil No.:

#4

Temp.:

20 ± 1 °C

Microbial biomass:

169 µg microbial C/g soil (Initial Biomass)

Details on experimental conditions:

EU Soil:
2. EXPERIMENTAL DESIGN
- Soil condition: fresh
- Soil (g/replicate): 100 g/replicate
- Control conditions, if used: 3 (biomass)
- No. of replication controls, if used: 3 (biomass)
- No. of replication treatments: 14
- Test apparatus: 250-mL glass flask
- Details of traps for CO2 and organic volatile, if any: Flow through system, Ethylene Glycol (organic volatiles), 2 N KOH (CO2)
- Identity and concentration of co-solvent: Acetonitrile

Test material application
- Volume of test solution used/treatment: 100 µL
- Application method: Applied by syringe (fine droplets)
- Is the co-solvent evaporated: No

Experimental conditions (in addition to defined fields)
- Moisture maintenance method: Flow through system with humidified air
- Continuous darkness: Yes

US Soil:
2. EXPERIMENTAL DESIGN
- Soil condition: fresh
- Soil (g/replicate): 100 g/replicate
- Control conditions, if used: 4 (biomass)
- No. of replication controls, if used: 4 (biomass)
- No. of replication treatments: 26
- Test apparatus: 250-mL glass flask
- Details of traps for CO2 and organic volatile, if any: Flow through system, Ethylene Glycol (organic volatiles), 2 N KOH (CO2)
- Identity and concentration of co-solvent: Acetonitrile

Test material application
- Volume of test solution used/treatment: 95 µL
- Application method: Applied by syringe (fine droplets)
- Is the co-solvent evaporated: No

Experimental conditions (in addition to defined fields)
- Moisture maintenance method: Flow through system with humidified air
- Continuous darkness: Yes

5. SAMPLING DETAILS
- Sampling intervals:
Hofchen am Hohenseh 4a: Day 0, 1,37 14,30,62,91, 120.
Laacher Hof AIII: Day 0, 1,37 14,30,62,91, 120.
Laacher Hof Axxa: Day 0, 1,37 14,30,62,91, 120.
Pikeville, NC: Day 0, 1,37 14,30,62,90, 120, 180,272,365.
- Sampling method for soil samples: Entire sample removed for extraction
- Method of collection of CO2 and volatile organic compounds: At each sampling time, the 2 N KOH traps were removed for CO2 and ethylene glycol trap was removed for extraction of volatile organics.

Soil No.:

#1

Sampling day(s):

120 d

% Total extractable:

7

% Non extractable:

35.4

% CO2:

51.7

% Other volatiles:

0

% Recovery:

96.3

St. dev.:

5

Remarks on result:

other:

Remarks:

Recovery after 120 days in soil Hoefchen am Hohenseh 4A

Soil No.:

#2

Sampling day(s):

120 d

% Total extractable:

11.6

% Non extractable:

34.7

% CO2:

48.5

% Other volatiles:

0

% Recovery:

98

St. dev.:

5.6

Remarks on result:

other:

Remarks:

Recovery after 120 days in soil Laacher Hof AIII

Soil No.:

#3

Sampling day(s):

120 d

% Total extractable:

12.8

% Non extractable:

26.8

% CO2:

53.3

% Other volatiles:

0

% Recovery:

98

St. dev.:

5.7

Remarks on result:

other:

Remarks:

Recovery after 120 days in soil Laacher Hof AXXa

Soil No.:

#4

Sampling day(s):

120 d

% Total extractable:

16.2

% Non extractable:

24.8

% CO2:

56.3

% Recovery:

97.3

Remarks on result:

other:

Remarks:

Recovery after 120 days in soil Pikeville

Soil No.:

#4

Sampling day(s):

365 d

% Total extractable:

11.1

% Non extractable:

23

% CO2:

59.9

% Other volatiles:

0

% Recovery:

99.3

St. dev.:

7.7

Remarks on result:

other:

Remarks:

Recovery after 365 days in soil Pikeville

Parent/product:

parent

Soil No.:

#1

% Degr.:

51.7

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days in soil Hoefchen am Hohenseh 4A

Parent/product:

parent

Soil No.:

#2

% Degr.:

48.5

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days in soil Laacher Hof AIII

Parent/product:

parent

Soil No.:

#3

% Degr.:

53.3

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days in soil Laacher Hof AXXa

Parent/product:

parent

Soil No.:

#4

% Degr.:

56.3

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days in soil Pikeville

Parent/product:

parent

Soil No.:

#4

% Degr.:

59.9

Parameter:

radiochem. meas.

Sampling time:

365 d

Remarks on result:

other:

Remarks:

Mineralisation after 365 days in soil Pikeville

Soil No.:

#1

DT50:

5.9 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#1

DT50:

12.5 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Soil No.:

#2

DT50:

10.6 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#2

DT50:

22.5 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Soil No.:

#3

DT50:

7.3 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#3

DT50:

15.5 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Soil No.:

#4

DT50:

9.3 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#4

DT50:

19.7 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Transformation products:

yes

No.:

#1

No.:

#2

Details on transformation products:

- Other:
Under aerobic conditions, the test substance (AE 0001789) undergoes hydrolysis of the cyclopropyl amide bond to give AE 0001789-descyclpropylamino (AE 0893016) as a major product. In addition it also undergoes demethylation to give a minor transformation product, AE 0001789-desmethyl (AE 1448796). The parent and metabolites undergo extensive mineralization to CO2 which is the major transformation product. The formation of nonextractable residues in soil is also a major dissipation pathway for AE 0001789.

Under aerobic conditions, AE 0001789 will rapidly degrade to AE 0893016 and AE 1448796. Both metabolites declined by the end of the study, suggesting that they are transient metabolites. This is further reinforced by the high percentage of 14CO2 by the study termination.

- Formation and decline of each transformation product during test:
- AE 0001789-descyclopropylamino (AE 0893016) was first detected at day 0 (0.4%) in the Hofchen am Hohenseh 4A soil and steadily increased to a maximum of 9.5% of the applied radioactivity on day 7, then declined through the end of the study.
- AE 0001789- desmethyl (AE 1448796) was first detected at day 1 (1.3%) in the Hofchen am Hohenseh 4A soil and steadily increased to a maximum of 4.9% of the applied radioactivity on day 14, then declined through the end of the study.

- AE 0001789-descyclopropylamino (AE 0893016) was first detected at day 1 (1.1%) in the Laacher Hof AllI soil and steadily increased to a maximum of 10.9% of the applied radioactivity on day 14, then declined through the end of the study.
- AE 0001789- desmethyl (AE 1448796) was first detected at day 1 (0.1%) in the Laacher Hof AllI soil and steadily increased to a maximum of 7.2% of the applied radioactivity on day 30, then declined through the end of the study.

- AE 0001789-descyclopropylamino (AE 0893016) was first detected at day 1 (2.7%) in the Laacher Hof AXXA soil and steadily increased to a maximum of 10.7% of the applied radioactivity on day 7, then declined through the end of the study.
- AE 0001789- desmethyl (AE 1448796) was first detected at day 1 (0.3%) in the Laacher Hof AXXa soil and steadily increased to a maximum of 6.6% of the applied radioactivity on day 14, then declined through the end of the study.

- AE 0001789-descyclopropylamino (AE 0893016) was first detected at day 1 (2.5%) in the Pikeville soil and steadily increased to a maximum of 7.4% of the applied radioactivity on day 7, then declined through the end of the study.
- AE 0001789-desmethyl (AE 1448796) was first detected at day 3 (1.2%) in the Pikeville soil and steadily increased to a maximum of 5.5% of the applied radioactivity on day 14, then declined through the end of the study.

Evaporation of parent compound:

yes

Volatile metabolites:

yes

Residues:

yes

Major Outcomes of Study:

AE 0001789 readily undergoes decarboxylation to AE 0893016, (9.5% Hofchen am Hohenseh at day 7, 10.9% LaacherAIII at day 14, 10.7% LaacherAXXa at day 7, 7.4% Pikeville at day 7). In addition AE 0001789 undergoes demethylation to (AE 1448796) (4.9% Hofchen am Hohenseh at day 14, 7.2% Laacher Hof AIII at day 30, 6.6% LaacherAXXa at day 14, 5.5% Pikeville at day 14). Parent AE 0001789 and is metabolites, mineralize rapidly under aerobic condition to CO2(51.7% Hofchen am Hohenseh, 48.5% Laacher Hof AIII, 53.3% LaacherAXXa, 59.9% Pikeville) by study end).

Reference 2

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

supporting study

Study period:

13 Oct 2004 - 12 Apr 2006

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 307 (Aerobic and Anaerobic Transformation in Soil)

Qualifier:

according to guideline

Guideline:

other: US EPA Subdivision N, Section 162-2

GLP compliance:

yes (incl. QA statement)

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

aerobic/anaerobic

Soil classification:

USDA (US Department of Agriculture)

Soil no.:

#1

Soil type:

sandy loam

% Clay:

10

% Silt:

14

% Sand:

76

% Org. C:

2

pH:

6.4 - 6.7

CEC:

9.8 meq/100 g soil d.w.

Bulk density (g/cm³):

1.17

Details on soil characteristics:

Soil Laacherhof AXXa:
- Geographic location: Monheim NRW, Germany, N 51° 04.647', E 06° 53.517'
- Pesticide use history at the collection site: No pesticides used since 1988
- Collection procedures: Hand shoveled
- Storage conditions: Stored at ca.2-8 °C
- Storage length: 16 d
- Sampling depth: 0-20 cm

Soil No.:

#1

Duration:

180 d

Soil No.:

#1

Initial conc.:

0.47 - 0.48 other: mg a.i./kg soil (methoxybenzoyl label and sulfonylbenzamide label)

Based on:

act. ingr.

Soil No.:

#1

Initial conc.:

0.79 other: mg a.i./Lwater (methoxybenzoyl label and sulfonylbenzamide label)

Based on:

act. ingr.

Soil No.:

#1

Initial conc.:

176.5 - 178.5 other: g a.i./ha (methoxybenzoyl label and sulfonylbenzamide label)

Based on:

act. ingr.

Parameter followed for biodegradation estimation:

radiochem. meas.

Soil No.:

#1

Temp.:

20 ±1 °C

Microbial biomass:

359 mg microbial C/ kg soil

Details on experimental conditions:

2. EXPERIMENTAL DESIGN
- Soil preincubation conditions:
- Soil condition: Air dried, sieved (2 mm)
- Soil (g/replicate): 100 g/replicate (dry wt.)
- Control conditions, if used: None
- No. of replication treatments: Duplicate (Single for day 5, 7 aerobic, day 126 (methoxybenzoyl label only))
- Test apparatus: 250-mL Pyrex Erlenmeyer flask with side-arm (aerobic) and double-valve sealable top (anaerobic)
- Details of traps for CO2 and organic volatile, if any:
Aerobic- Soda lime and glass wool (biometer flask)
Anaerobic — Sealed system for collection of volatiles
- Identity and concentration of co-solvent: Acetonitrile

Test material application
- Volume of test solution used/treatment: 106 µL
- Application method: Treatment solution added using a 250-µL pipette uniformly onto the soil surface; samples were rotated for mixing
- Is the co-solvent evaporated: None

Any indication of the test material adsorbing to the walls of the test apparatus: None

Experimental conditions (in addition to defined fields)
- Moisture maintenance method: Not necessary- samples were flooded after 7 days
- Continuous darkness: Yes


5. SAMPLING DETAILS
- Sampling intervals:
Aerobic: 0, 5, 7 days post-application
Anaerobic (methoxybenzoyl): 0, 7, 18,21,40,62,92, 118, 126 and 180 days post-flooding
Anaerobic (sulfonylbenzamide): 0, 7, 18,21, 40, 62, 92, 1 1 8, 1 80 days post flooding
- Sampling method for soil samples: Entire sample filtered, extracted and air dried.
- Method of collection of CO2 and volatile organic compounds:
Aerobic: Test systems were purged with nitrogen before flooding.
Anaerobic: Volatiles purged into series of traps (2 M KOH, 2 M KOH, Ethylene Glycol, 1 M H2S04) with nitrogen gas at each sampling interval.
- Sampling intervals/times for:
> Moisture content: Moisture was adjusted at the time of treatment.
> Sample storage before analysis: Refrigerated (< 8 °C)
- Other observations, if any: None

Soil No.:

#1

Sampling day(s):

180 d

% Total extractable:

24.1

% Non extractable:

18.8

% CO2:

14.3

% Other volatiles:

5.6

% Recovery:

88.7

St. dev.:

6.6

Remarks on result:

other:

Remarks:

Material balance of radioactivity of [methoxybenzoyl-UL-14C] AE 0001789 from anaerobic soil after 180 days.

Soil No.:

#1

Sampling day(s):

180 d

% Total extractable:

67.2

% Non extractable:

7.9

% CO2:

3.1

% Other volatiles:

0

% Recovery:

96.2

St. dev.:

1.1

Remarks on result:

other:

Remarks:

Material balance of radioactivity of [sulfonylbenzamide-UL-14C] AE 0001789 from anaerobic soil after 180 days.

Parent/product:

parent

Soil No.:

#1

% Degr.:

14.3

Parameter:

radiochem. meas.

Sampling time:

180 d

Remarks on result:

other:

Remarks:

Mineralisation of [methoxybenzoyl-UL-14C] AE 0001789 from anaerobic soil after 180 days.

Parent/product:

parent

Soil No.:

#1

% Degr.:

3.1

Parameter:

radiochem. meas.

Sampling time:

180 d

Remarks on result:

other:

Remarks:

Mineralisation of [sulfonylbenzamide-UL-14C] AE 0001789 from anaerobic soil after 180 days.

Soil No.:

#1

DT50:

59.5 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Remarks on result:

other:

Remarks:

Label Position: Methoxybenzoyl

Soil No.:

#1

DT50:

126.3 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C. Label Position: Methoxybenzoyl

Soil No.:

#1

DT50:

48.5 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Remarks on result:

other:

Remarks:

Label Position: Sulfonylbenzamide

Soil No.:

#1

DT50:

103 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C. Label Position: Sulfonylbenzamide

Transformation products:

yes

No.:

#1

No.:

#2

No.:

#3

No.:

#4

Details on transformation products:

- Other: Identification of the transformation products was accomplished by mass spectral analysis and co-chromatography with reference standards.

Evaporation of parent compound:

not specified

Volatile metabolites:

yes

Residues:

yes

Details on results:

Major Outcomes of Study:
The test substance (AE 0001789) degraded rapidly to 50.6%, and 54.4% of the applied radioactivity in 7 days under aerobic conditions, for the methoxybenzoyl and sulfonylbenzamide labels respectively. Under anaerobic conditions, this degradation was considerably slower. In the methoxybenzoyl label, AE 0001789 degraded from 55.7% at day 0 to 17.3% by the end of the study. In the sulfonylbenzamide label, AE 0001789 degraded from 56.1% at day 0 to 10.7% by the end of the study.
 
There were four major metabolites in this study. AE 0893016 was present in both label studies, at a maximum of 21.0% at day 21 in the methoxybenzoyl label, and 19.9% at day 18 in the sulfonylbenzamide label. AE 0467398 was present in the sulfonylbenzamide label study, with a maximum of 52.5% by the end of the study. AE 0852999 was also present in the sulfonylbenzamide label, with a maximum of 14.6% at day 7 (anaerobic). Salicylic acid was found in the methoxybenzoyl label, with a maximum of 18.1% at day 118.
 
14C02 accounted for 14.3%, and organic volatiles accounted for 5.6% of the applied radioactivity by the end of the study in the methoxybenzoyl label. Volatiles remained low in the sulfonylbenzamide label. Non-extractable residues reached a maximum of 22.4% at day 126 in the methoxybenzoyl label, and 7.9% at the end of the study in the sulfonylbenzamide label.

Significance of Results to Environmental Behavior of Test Compound

Under anaerobic soil conditions, the test substance will degrade significantly. However, degradation of the substance will proceed more rapidly under aerobic conditions.

Reference 3

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

key study

Study period:

03 Jun 2003 - 25 Oct 2004

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 307 (Aerobic and Anaerobic Transformation in Soil)

Qualifier:

according to guideline

Guideline:

other: US EPA Subdivision N, Section 162-1

Qualifier:

according to guideline

Guideline:

other: Commission Directive 95/36/EC amending Council Directive 91/414/EEC (Annexes I and II, Fate and Behaviour in the Environment), July 14, 1995

Qualifier:

according to guideline

Guideline:

other: SETAC Procedures for Assessing the Environmental Fate and Ecotoxicity of Pesticides

GLP compliance:

yes (incl. QA statement)

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

aerobic

Soil classification:

USDA (US Department of Agriculture)

Soil no.:

#1

Soil type:

sandy loam

% Clay:

9

% Silt:

33.9

% Sand:

57.1

% Org. C:

1

pH:

5.9

CEC:

4.5 meq/100 g soil d.w.

Bulk density (g/cm³):

2.6

Soil no.:

#2

Soil type:

silt loam

% Clay:

15

% Silt:

66

% Sand:

19

% Org. C:

2.33

pH:

6.3

CEC:

12.9 meq/100 g soil d.w.

Bulk density (g/cm³):

2.09

Soil no.:

#3

Soil type:

loamy sand

% Clay:

7

% Silt:

10

% Sand:

83

% Org. C:

2.38

pH:

6.5

CEC:

11 meq/100 g soil d.w.

Bulk density (g/cm³):

2.5

Soil no.:

#4

Soil type:

silt loam

% Clay:

12

% Silt:

51.1

% Sand:

36.9

% Org. C:

0.83

pH:

7.5

CEC:

8 meq/100 g soil d.w.

Bulk density (g/cm³):

2.55

Details on soil characteristics:

SOIL COLLECTION AND STORAGE

1#: Soil Pikeville:
- Geographic location: Pikeville, North Carolina, USA, N 35° 29.303', W 78° 02.421'
- Pesticide use history at the collection site: No pesticides for over 10 year
- Collection procedures: Hand shoveled
- Storage conditions: Stored at ca. 5 °C
- Storage length: June 02, 2003
- Sampling depth: 0-8 inch
- Soil preparation: Sieved (2 mm)

2#: Soil Hoefchen:
- Geographic location: Burscheid NRW, Germany, N 51° 04.011', E 07° 06.327'
- Pesticide use history at the collection site: No pesticides used since 1989
- Collection procedures: Hand shoveled
- Storage conditions: Stored at ca. 5 °C
- Storage length: June 02, 2003
- Sampling depth: 0-8 inch
- Soil preparation: Sieved (2 mm)

3#: Soil Laacherhof AXXa:
- Geographic location: Monheim NRW, Germany, N 51° 04.647', E 06° 53.517'
- Pesticide use history at the collection site: No pesticides used since 1988
- Collection procedures: Hand shoveled
- Storage conditions: Stored at ca. 5 °C
- Storage length: June 02, 2003
- Sampling depth: 0-8 inch
- Soil preparation: Sieved (2 mm):

4 #: Soil Laacherhof AIII:
- Geographic location: Monheim NRW, Germany, N 51° 05. 173', E 06° 55.758'
- Pesticide use history at the collection site: Several pesticides used. However a safener like AE 0001789 was not used in the past.
- Collection procedures: Hand shoveled
- Storage conditions: Stored at ca. 5 °C
- Storage length: June 02, 2003
- Sampling depth: 0-8 inch
- Soil preparation: Sieved (2 mm)

Soil No.:

#1

Duration:

364 d

Soil No.:

#2

Duration:

120 d

Soil No.:

#3

Duration:

120 d

Soil No.:

#4

Duration:

120 d

Soil No.:

#1

Initial conc.:

6.6 other: µg per 100 g of soil as dry matter

Based on:

test mat.

Soil No.:

#2

Initial conc.:

40 other: µg per 100 g of soil as dry matter

Based on:

test mat.

Soil No.:

#3

Initial conc.:

40 other: µg per 100 g of soil as dry matter

Based on:

test mat.

Soil No.:

#4

Initial conc.:

40 other: µg per 100 g of soil as dry matter

Based on:

test mat.

Parameter followed for biodegradation estimation:

radiochem. meas.

Soil No.:

#1

Temp.:

20.1 °C ± 0.2°C

Microbial biomass:

day 0 without solvent used for application & test item: 220 (as mg microbial carbon per kg of soil)

Soil No.:

#2

Temp.:

20.1 °C ± 0.2°C

Microbial biomass:

day 0 without solvent used for application & test item: 738 (as mg microbial carbon per kg of soil)

Soil No.:

#3

Temp.:

20.1 °C ± 0.2°C

Microbial biomass:

day 0 without solvent used for application & test item: 319 (as mg microbial carbon per kg of soil)

Soil No.:

#4

Temp.:

20.1 °C ± 0.2°C

Microbial biomass:

day 0 without solvent used for application & test item: 680 (as mg microbial carbon per kg of soil)

Details on experimental conditions:

1. PRELIMINARY EXPERIMENTS: No

2. EXPERIMENTAL DESIGN:
- Soil condition: fresh
- Soil: 100 g dry mass / replicate
- No. of replication controls, if used: not used
- No. of replication treatments: 2 (Pikeville), 1-2 (Hoefchen, LH AXXa, LH AIII)
- Test apparatus (Type/material/volume): Erlenmeyer flask
- Details of traps for CO2 and organic volatile, if any: Solid soda lime traps
- Identity and concentration of co-solvent: Acetonitrile/water (1:2; v:v)

Test material application
- Volume of test solution used/treatment: 80.3 µL (Pikeville) and 487 µL (Hoefchen, LH AXXa, LH AIII)
- Application method: The soil samples were treated directly as it would happen during a spray application
- Is the co-solvent evaporated: No

Any indication of the test material adsorbing to the walls of the test apparatus: No

Experimental conditions (in addition to defined fields)
- Moisture maintenance method: Weighing and adding lost water
- Continuous darkness: Yes

5. SAMPLING DETAILS
- Sampling intervals: 0, 1, 3, 7, 14, 30, 62, 90, 120, days post-application (240, 364)
- Method of collection of CO2 and volatile organic compounds: Soda lime & PU
- Sampling intervals/times for:
> Moisture content: Every sampling date
> Sample storage before analysis: Soil: not stored prior extraxtion; Extracts: 1st analysis performed one day

Soil No.:

#1

Sampling day(s):

364 d

% Total extractable:

6.4

% Non extractable:

24.3

% CO2:

70.3

% Other volatiles:

< 0.1

Remarks on result:

other:

Remarks:

Material balances after 364 days, Pikeville: 101.0%

Soil No.:

#1

Sampling day(s):

120 d

% Total extractable:

11.4

% Non extractable:

35.3

% CO2:

58.6

% Other volatiles:

< 0.1

Remarks on result:

other:

Remarks:

Material balances after 120 days, Pikeville: 105.3%

Soil No.:

#2

Sampling day(s):

120 d

% Total extractable:

7.9

% Non extractable:

30.8

% CO2:

61.9

% Other volatiles:

< 0.1

Remarks on result:

other:

Remarks:

Material balances after 120 days, Hoefchen: 100.5%

Soil No.:

#3

Sampling day(s):

120 d

% Total extractable:

20

% Non extractable:

33.3

% CO2:

47.2

% Other volatiles:

< 0.1

Remarks on result:

other:

Remarks:

Material balances after 120 days, Laacherhof AXXa: 100.5%

Soil No.:

#4

Sampling day(s):

120 d

% Total extractable:

17.8

% Non extractable:

37.5

% CO2:

43

% Other volatiles:

< 0.1

% Recovery:

98.3

Remarks on result:

other:

Remarks:

Material balances after 120 days, Laacherhof AIII

Parent/product:

parent

Soil No.:

#1

% Degr.:

70.3

Parameter:

radiochem. meas.

Sampling time:

364 d

Remarks on result:

other:

Remarks:

Mineralisation after 364 days, Pikeville

Parent/product:

parent

Soil No.:

#1

% Degr.:

58.6

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days, Pikeville

Parent/product:

parent

Soil No.:

#2

% Degr.:

61.9

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days, Hoefchen

Parent/product:

parent

Soil No.:

#3

% Degr.:

47.2

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days, Laacherhof AXXa

Parent/product:

parent

Soil No.:

#4

% Degr.:

43

Parameter:

radiochem. meas.

Sampling time:

120 d

Remarks on result:

other:

Remarks:

Mineralisation after 120 days, Laacherhof AIII

Soil No.:

#1

DT50:

2.3 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#1

DT50:

4.9 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Soil No.:

#2

DT50:

2.9 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#2

DT50:

6.2 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Soil No.:

#3

DT50:

7.6 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#3

DT50:

16.1 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Soil No.:

#4

DT50:

8 d

Type:

(pseudo-)first order (= half-life)

Temp.:

20 °C

Soil No.:

#4

DT50:

17 d

Type:

(pseudo-)first order (= half-life)

Temp.:

12 °C

Remarks on result:

other:

Remarks:

Calculated DT50 at 12 °C, based on results at 20 °C.

Transformation products:

yes

No.:

#1

No.:

#2

No.:

#3

No.:

#4

Details on transformation products:

Four major transformation products in soil were found:
• AE 0001789-cyclopropyl-sulfamoylbenzamide (AE 0852999, 4-[(2-methoxy benzoyl)sulfamoyl] benzoic acid): maximum concentration 29.6% of the applied amount, observed on the 7th day of incubation (Pikeville), 22.0% on day 7 (Hoefchen), 30.3% on day 14 (Laacherhof AXXa) and 15.7% on day 14 (Laacherhof AIM). The corresponding concentrations at the end of the study were 1.3%, 4.4%, 10.9% and 2.5%, respectively.
• AE 0001789-descyclopropylamino (AE 0893016, 4-[(2-methoxybenzoyl) sulfamoyl] benzoic acid): maximum concentration 5.8% of the applied amount, found at the 1st day of incubation (Pikeville), 8.0% on day 3 (Hoefchen), 9.3% on day 7 (Laacherhof AXXa) and 13.0% on day 7 (Laacherhof AIM). The corresponding concentrations at the end of the study were <0.1% of the applied amount in all soils.
• AE 0001789-sulfamoylbenzoic acid (AE 0467398, 4-sulfamoylbenzoic acid):
maximum concentration 0.8% of the applied amount, measured on the 3rd day of incubation (Pikeville), 2.3% on day 7 (Hoefchen), 11.5% on day 62 (Laacherhof AXXa) and 28.4% on day 30 (Laacherhof AIM). The corresponding concentrations at the end of the study were <0.1 %, 1.6%, 2.6% and 11.3%, respectively.
• AE 0001789-desmethyl (AE 1448796, N-cyclopropyl-4-[(2-hydroxybenzoyl) sulfamoyl]benzamide): maximum concentration 2.7% of the applied amount, measured on the 3rd day of incubation (Pikeville), 3.6% on day 7 (Hoefchen), 6.0% on day 30 (Laacherhof AXXa) and 3.8% on day 14 (Laacherhof AIM). The corresponding concentrations at the end of the study were 0.4%, 0.8%, 3.7% and 2.3%, respectively.

Two minor transformation products were detected in this study with maximum concentrations of 1.2% and 3.0% (day 62 and day 120, Pikeville). At the end of the study they were no longer detectable
In all cases it could be shown, that all metabolites were declining towards the end of the study.
- Figure attached: No
- Other: The test item is well degraded in soil either via desmethylation of the methoxy group and/or loss of anisic acid moiety forming AE 0001789- cyclopropylsulfamylbenzamide or via secession of the cyclopropylamino group also followed by secession of the anisic acid moiety. All these metabolites were finally mineralized to 14CO2.

Evaporation of parent compound:

no

Volatile metabolites:

no

Residues:

yes

Conclusion:

The data gathered in the current laboratory investigation demonstrated that AE 0001789 was degraded rapidly in all 4 soils with a DT50 of 2 - 8 days (mean 5 days, 20 °C).

In the course of the experiment four major degradation products were detected and quantified together with unaltered test item and material remaining at the origin after TLC separation.

The metabolite AE 0001789-cyclopropyl-sulfamoylbenzamide (AE 0852999, ZMF14) was found as a degradation product with a maximum amount of 30.3% of AR after 14 days of incubation (max. in soil LH AXXa), then declining to 10.9% at study termination.

The metabolite AE 0001789-sulfamoylbenzoic acid (AE 0467398, ZMF13) was measured with 28.4% of AR (max. at DAT 30 in soil LH AIII), then declining to 11.3% at study termination.

The metabolite AE 0001789-descyclopropylamino (AE 0893016, ZMF12) was 13.0% of AR (max. at DAT 7 in soil LH AIII), declining to 0.4% at DAT 62 and the metabolite AE 0001789-desmethyl (AE 1448796) was 6.0% of AR (max. at DAT 30 in soil LH AXXa), then declining to 3.7% at study termination.

 

The total of all other detected individual radioactive zones corresponded to 5.3% of AR in maximum during the entire study (up to 4 zones incl. origin of TLC) and showed a significant trend for a decrease towards the end of the test.

In all test series the amount of14C02 rapidly increased over the entire study period. At the end of the study, 364 days after application (Pikeville soil), about 70% of the applied radioactivity was measured as14C02. The values for soil Hoefchen, LH

AXXa and LH AIII (120 days after application) were 62%, 47% and 43%, respectively

Along with the overall metabolism of the test substance bound residues were formed. The portions of unextractable residues at DAT 0 were low (5.4 to 7.1%), then increased to a value of 24.3 to 37.5% at study termination.

Description of key information

Aeroboc soil:  DT50 of parent substance: 4.9 - 22.5 days at 12 °C (aerob, OECD 307, EPA 162-1, four soils).

Anaeroboc soil: DT50 of parent substance: 103 - 126.3 days at 12 °C (anaerob, OECD 307, one soil).

Key value for chemical safety assessment

Half-life in soil:

22.5 d

at the temperature of:

12 °C

Additional information

The degradation of Cyprosulfamide in soil has been extensively investigated. The objective of the studies was to determine the route and rate of degradation of the substance under aerobic and anaerobic conditions in soil. For this purpose, the concentrations of the substance and its metabolites in soil, their rate of formation and degradation and their identity were determined with radioactive labelled test item under laboratory conditions. Additionally, volatile components including 14CO2 as terminal degradation product and non-extractable residues were quantified to establish full material balances.

Following intended use, the aerobic soil environment will have a significant contribution to the overall degradation of the substance. The substance is oxidized to degradation products which are mineralized to CO2.

 The route of degradation of the substance in soil has been investigated in two aerobic soil metabolism studies (M-257897-01-2 [OECD 307] and M-279303-02-1 [EPA 162-1]) with the substance uniformly 14C-labelled each in the two phenyl rings (firstly insulfonylbenzamide, S-label, and secondly in the methoxybenzoyl ring, M-label). In each study four different soils were investigated under aerobic conditions. 14C-labelled Cyprosulfamide (S- and M-label) were degraded in soil to result in DT50 values ranging from 2.3 to 10.6 days at 20 °C (4.9 - 22.5 days, recalculated to 12 °C) assuming single first order degradation kinetics. After 120 days 43 - 61.9% of AR were found mineralized to 14CO2.

 An additional study investigated the biotic degradation under anaerobic conditions (M-279306-01-1), following OECD 307. The test compound was degraded under conditions of flooded anaerobic soil of the laboratory. Degradation of Cyprosulfamide (S- and M-label) was significantly slower as reflected by a DT50 of 48.5 - 59.5 days at 20°C (103 - 126.3 days, recalculated to 12 °C) assuming first order degradation kinetics. After 180 days 3.1 - 14.3% of AR were found mineralized to 14CO2.