1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide

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:

key study

Study period:

03 Nov 2010 - 23 Sep 2013

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)

Deviations:

no

Qualifier:

according to guideline

Guideline:

EPA OPPTS 835.4100 (Aerobic Soil Metabolism)

Deviations:

no

Qualifier:

according to guideline

Guideline:

other: Commission Directive 95/36/EC amending Council Directive 91/414, 1995; Regulation (EC) No 1107/2009, 2009

Deviations:

no

GLP compliance:

yes

Remarks:

Ministerium für Arbeit, Gesundheit und Soziales des Landes Nordrhein-Westfalen, Düsseldorf, Germany

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

aerobic

Soil classification:

USDA (US Department of Agriculture)

Year:

2013

Soil no.:

#1

Soil type:

loamy sand

% Clay:

5

% Silt:

16

% Sand:

79

% Org. C:

ca. 1.8

pH:

6.2

CEC:

8.4 meq/100 g soil d.w.

Bulk density (g/cm³):

1.21

Soil no.:

#2

Soil type:

loam

% Clay:

25

% Silt:

40

% Sand:

35

% Org. C:

5.1

pH:

7.3

CEC:

19.3 meq/100 g soil d.w.

Bulk density (g/cm³):

0.96

Soil no.:

#3

Soil type:

silt loam

% Clay:

15

% Silt:

54

% Sand:

31

% Org. C:

2.7

pH:

5.3

CEC:

9.6 meq/100 g soil d.w.

Bulk density (g/cm³):

1.04

Soil no.:

#4

Soil type:

silt loam

% Clay:

19

% Silt:

56

% Sand:

25

% Org. C:

2.7

pH:

6.4

CEC:

12.7 meq/100 g soil d.w.

Bulk density (g/cm³):

1.05

Details on soil characteristics:

SOIL COLLECTION AND STORAGE
- Geographic location: North Rhine-Westphalia, Germany
- Pesticide use history at the collection site: No pesticide used for previous 5 years
- Collection procedures: Samples taken with shovel and placed in plastic bags
- Sampling depth: 0 - 20 cm
- Storage conditions: 20 °C
- Storage length: 7 days before application
- Soil preparation: Soil passed through 2 mm sieve

PROPERTIES OF THE SOILS (in addition to defined fields)
- Moisture at 1/3 atm: 11.1, 33.9, 25.6, 23.1%, respectively
- Bulk density: 1.21, 0.96, 1.04, 1.05 g/cm3, respectively

Soil No.:

#1

Duration:

>= 0 - <= 119 d

Soil No.:

#2

Duration:

>= 0 - <= 119 d

Soil No.:

#3

Duration:

>= 0 - <= 119 d

Soil No.:

#4

Duration:

>= 0 - <= 119 d

Soil No.:

#1

Initial conc.:

0.5 mg/kg soil d.w.

Based on:

act. ingr.

Soil No.:

#2

Initial conc.:

0.5 mg/kg soil d.w.

Based on:

act. ingr.

Soil No.:

#3

Initial conc.:

0.5 mg/kg soil d.w.

Based on:

act. ingr.

Soil No.:

#4

Initial conc.:

0.5 mg/kg soil d.w.

Based on:

act. ingr.

Parameter followed for biodegradation estimation:

CO2 evolution

radiochem. meas.

Soil No.:

#1

Temp.:

20 +/- 2 °C

Humidity:

53.9% of MWHC

Microbial biomass:

DAT-0: 627 mg microbial carbon/kg soil dwt

Soil No.:

#2

Temp.:

20 +/- 2 °C

Humidity:

53.9% of MWHC

Microbial biomass:

DAT-0: 2349 mg microbial carbon/kg soil dwt

Soil No.:

#3

Temp.:

20 +/- 2 °C

Humidity:

53.9% of MWHC

Microbial biomass:

DAT-0: 486 mg microbial carbon/kg soil dwt

Soil No.:

#4

Temp.:

20 +/- 2 °C

Humidity:

53.9% of MWHC

Microbial biomass:

DAT-0: 774 mg microbial carbon/kg soil dwt

Details on experimental conditions:

1. EXPERIMENTAL DESIGN
- Soil preincubation conditions (duration, temperature if applicable): Stored at approximately 20 °C for 7 days propir to use.
- Soil condition: fresh
- Soil (g/replicate): 200 g/replicate, duplicate samples for each sampling interval
- No. of replication treatments: 2 per sampling interval
- Test apparatus (Type/material/volume): 300 mL Erlenmeyer glass flasks were used as incubation vessels
- Details of traps for CO2 and organic volatile, if any: each flask was fitted with a trap attachment (permeable for oxygen) containing soda lime for absorption of carbon dioxide and a polyurethane (PU) foam plug for adsorption of volatile organic compounds (VOC).
- Identity and concentration of co-solvent: Aqueous 0.01 M CaCl2 solution

2. TEST MATERIAL APPLICATION
- Volume of test solution used/treatment: 195 μL of application solution was applied per replicate
- Application method (e.g. applied on surface, homogeneous mixing etc.): Application solution were applied drop-wise onto the soil surface of the respective equilibrated test systems using a pipette to obtain the nominal test item concentration of 533 μg/kg soil dry weight.
- Is the co-solvent evaporated: No

Any indication of the test material adsorbing to the walls of the test apparatus: No. Mean material balances were 97.2% AR (range of 94.2 to 100.7% AR) for soil Laacher Hof AXXa, 98.5% AR (range of 95.0 to 101.3% AR) for soil Dollendorf II, 98.0% AR (range of 94.5 to 101.7% AR) for soil Hanscheiderhof and 98.0% AR (range of 94.3 to 100.8% AR) for soil Hoefchen Am Hohenseh 4a.
The complete material balances found at all sampling intervals in all soils demonstrated that no significant portion of radioactivity dissipated from the test systems or was lost during sample processing.

3. EXPERIMENTAL CONDITIONS (in addition to defined fields)
- Moisture maintenance method: Re-weighing and addition of lost water on DAT-29, DAT-59 and DAT-90.
- Continuous darkness: Yes
4. SAMPLING DETAILS
- Sampling intervals: 0/0.02*, 0/1*, 2, 6, 9, 16, 22, 29, 62, 91 and 119 days after application
(*D0/0.02 and D0/1: Samples shaken overhead with CaCl2 solution for 0.5 h and 24 h, respectively)
- Sampling method for soil samples: In order to determine the desorption behavior of the test item in soil, the entire soil sample was first extracted with aqueous CaCl2 solution. After shaking for 24 hours to gain equilibrium, the suspension was centrifuged and the supernatant was removed. The remaining soil was extracted with organic solvents at room temperature (ambient organic extracts) and under elevated temperature conditions (70 °C, aggressive organic extracts).
- Method of collection of CO2 and volatile organic compounds: Soda lime for absorption of 14CO2 and polyurethane foam for volatile organic compounds
- Sampling intervals/times for:
> Moisture content: DAT-29, DAT-59 and DAT-90
> Sample storage before analysis: The soils were processed immediately after sampling; prior to analysis all extracts were stored in a freezer in the dark.
- Other observations, if any: Soil microbial biomass was determined at test start, in the middle and at the end. Measurements were conducted for untreated soil at DAT-0, DAT-62 and DAT-212, as well as for soil treated with application solvent at DAT-60 and DAT-120

Soil No.:

#1

% Recovery:

97.2

St. dev.:

2.1

Soil No.:

#2

% Recovery:

98.5

St. dev.:

2.1

Soil No.:

#3

% Recovery:

98

St. dev.:

1.8

Soil No.:

#4

% Recovery:

98

St. dev.:

1.9

Key result

Soil No.:

#1

% Degr.:

41.9

St. dev.:

0.5

Parameter:

other: Percentage of applied radioactivity remaining

Sampling time:

119 d

Key result

Soil No.:

#2

% Degr.:

4.9

St. dev.:

0.1

Parameter:

other: Percentage of applied radioactivity remaining

Sampling time:

119 d

Key result

Soil No.:

#3

% Degr.:

55.9

St. dev.:

0.1

Parameter:

other: Percentage of applied radioactivity remaining

Sampling time:

119 d

Key result

Soil No.:

#4

% Degr.:

17.1

St. dev.:

0.8

Parameter:

other: Percentage applied radioactivity remaining

Sampling time:

119 d

Key result

Soil No.:

#1

DT50:

94.4 d

Type:

other: DFOP

Temp.:

20 °C

Key result

Soil No.:

#2

DT50:

18.4 d

Type:

other: FOMC

Temp.:

20 °C

Key result

Soil No.:

#3

DT50:

182.7 d

Type:

other: FOMC

Temp.:

20 °C

Key result

Soil No.:

#4

DT50:

43.8 d

Type:

other: FOMC

Temp.:

20 °C

Transformation products:

yes

No.:

#1

No.:

#2

No.:

#3

No.:

#4

No.:

#5

No.:

#6

Details on transformation products:

- Formation and decline of each transformation product during test:
Besides the formation of carbon dioxide, six major degradation products were identified. Pyrazole-carboxamide-quinazolinone-carboxylic acid (Reg 1) was detected with maximum amounts of 6.5%AR at DAT-119 in soil Dollendorf II, Pyrazole-carboxamide-N-methyl-quinazolinone (Reg 2) with 14.6%AR at DAT-91 in soil Hoefchen Am Hohenseh 4a, test substance-amide (Reg 3) with 6.9%AR at DAT-62 in soil Hanscheiderhof, test substance-carboxylic acid (Reg 4)with 47.8%AR at DAT-62 in soil Dollendorf II, Pyrazole-carboxamide-desmethyl-amide-carboxylic acid (Reg 6) with 12.0%AR at DAT-119 in soil Hoefchen Am Hohenseh 4a and Pyrazole-carboxamide-N-methyl-quinazolinone-carboxylic acid (Reg 8) with 10.6%AR at DAT-119 in soil Dollendorf II. Furthermore, five minor degradation products were found with no component exceeding 3.5%AR at any sampling interval.

- Pathways for transformation:
Based on the results of the study, the following pathway for the degradation of [Pyrazole-carboxamide-14C] under aerobic conditions is proposed, with e.g. the following possible processes involved:
• Cyclization of Pyrazole-carboxamide to result in the formation of Reg 2 and Reg 8
• Hydrolysis of the nitrile group of Pyrazole-carboxamide to result in Reg 3 (amide)
• Hydrolytic deamination of the amino group to result in Reg 4 (Carboxylic acid)
• Demethylation of the carboxylic acid amide of Reg 4 to result in Reg 6 (Desmethylamide-COOH).
• Cyclization of Reg 4 to result in formation of Reg 8 (N-methyl-quinazolinone-COOH).
• Cyclization of Reg 6 to result in Reg 1 (quinazolinone-COOH).
• Demethylation of the pyrimidine ring of Reg 8 to result in Reg 1 (Quinazolinone-COOH).
• Mineralization (carbon dioxide formation).
• Formation of non-extractable 14C-residues.

Evaporation of parent compound:

no

Volatile metabolites:

no

Residues:

yes

Details on results:

TEST CONDITIONS
- Aerobicity (or anaerobicity), moisture, temperature and other experimental conditions maintained throughout the study: Yes

MAJOR TRANSFORMATION PRODUCTS
- Range of maximum concentrations in % of the applied amount and day(s) of incubation when observed: Six major degradation products were identified. Pyrazole-carboxamide-quinazolinone-carboxylic acid (Reg 1) was detected with maximum amounts of 6.5%AR at DAT-119 in soil Dollendorf II, Pyrazole-carboxamide-N-methyl-quinazolinone (Reg 2) with 14.6%AR at DAT-91 in soil Hoefchen Am Hohenseh 4a, test substance-amide (Reg 3) with 6.9%AR at DAT-62 in soil Hanscheiderhof, test substance-carboxylic acid (Reg 4 with 47.8%AR at DAT-62 in soil Dollendorf II, Pyrazole-carboxamide-desmethyl-amide-carboxylic acid (Reg 6) with 12.0%AR at DAT-119 in soil Hoefchen Am Hohenseh 4a and Pyrazole-carboxamide-N-methyl-quinazolinone-carboxylic acid (Reg 8) with 10.6%AR at DAT-119 in soil Dollendorf II.

MINOR TRANSFORMATION PRODUCTS
- Range of maximum concentrations in % of the applied amount and day(s) of incubation when observed: Five minor degradation products were found with no component exceeding 3.5%AR at any sampling interval.

EXTRACTABLE RESIDUES
- % of applied amount at day 0: 40.6, 30.1, 21.6 and 28.7 in soils Laacher Hof AXXa and Hanscheiderhof, Dollendorf II and Hoefchen Am Hohenseh 4a, respectively.
- % of applied amount at end of study period: 27.6, 17.2, 33.0 and 30.7 in soils Laacher Hof AXXa and Hanscheiderhof, Dollendorf II and Hoefchen Am Hohenseh 4a, respectively.

NON-EXTRACTABLE RESIDUES
- % of applied amount at day 0: : 0.2, 0.7, 0.3 and 0.3% in soils Laacher Hof AXXa, Dollendorf II, Hanscheiderhof and Hoefchen Am Hohenseh 4a, respectively.
- % of applied amount at end of study period: 5.2, 13.9, 9.3 and 8.1% in soils Laacher Hof AXXa, Dollendorf II, Hanscheiderhof and Hoefchen Am Hohenseh 4a, respectively.

MINERALISATION
- % of applied radioactivity present as CO2 at end of study: 0.5%AR. Due to the low amount of CO2 detected no further identification procedures were performed.

VOLATILIZATION
- % of the applied radioactivity present as volatile organics at end of study: Formation of VOC was insignificant as demonstrated by values of ≤ 0.1% AR at all sampling intervals.

            Best-fit degradation kinetics of Test Substance in soils under aerobic conditions for trigger evaluation according to FOCUS

Soil	Kinetic	DT50	DT90	chi^2error	Visual
(Soil Type)	Model^1	[d]	[d]	[%]	Assessment ^2
Laacher Hof AXXa (Loamy Sand)	DFOP	94.5	959.1	1.0	+
Dollendorf II (Loam)	FOMC	18.4	83.4	1.9	+
Hanscheiderhof (Silt Loam)	FOMC	183	> 1000	0.7	+
Hoefchen Am Hohenseh 4a (Silt Loam)	FOMC	43.8	176.8	1.3	+
^1FOMC = first order multi compartment DFOP = double first order in parallel
^2Visual assessment: + good; ○ moderate; - poor

Reference 2

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

key study

Study period:

9 Jan 2013 - 14 Feb 2015

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)

Deviations:

no

Qualifier:

according to guideline

Guideline:

EPA OPPTS 835.4200 (Anaerobic Soil Metabolism)

Deviations:

no

Qualifier:

according to guideline

Guideline:

other: Japanese MAFF New Test Guidelines for Supporting Registration of Chemical Pesticides 12 Nousan 8147, Annex No. 2-5-3

Deviations:

no

Qualifier:

according to guideline

Guideline:

other: Commission Regulation (EU) No 283/2013 in accordance with Regulation (EC) No 1107/2009

Deviations:

no

GLP compliance:

yes

Remarks:

Ministerium für Arbeit, Gesundheit und Soziales des Landes Nordrhein-Westfalen, Düsseldorf, Germany

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

aerobic/anaerobic

Soil classification:

USDA (US Department of Agriculture)

Year:

2014

Soil no.:

#1

Soil type:

sandy loam

% Clay:

7

% Silt:

19

% Sand:

74

% Org. C:

1.6

pH:

6.3

CEC:

8.6 meq/100 g soil d.w.

Bulk density (g/cm³):

1.27

Soil no.:

#2

Soil type:

silt loam

% Clay:

15

% Silt:

57

% Sand:

26

% Org. C:

1.8

pH:

6.1

CEC:

11.1 meq/100 g soil d.w.

Bulk density (g/cm³):

1.12

Soil no.:

#3

Soil type:

loam

% Clay:

27

% Silt:

31

% Sand:

42

% Org. C:

4.9

pH:

7.1

CEC:

20.6 meq/100 g soil d.w.

Bulk density (g/cm³):

0.98

Details on soil characteristics:

SOIL COLLECTION AND STORAGE
- Geographic location: Monheim, Burscheid and Blankenheim, Germany for the Laacher Hof AXXa, Hoefchen am Hohenseh 4a and Dollendorf II, respectively
- Pesticide use history at the collection site: No plant protection products applied for at least 5 years.
- Collection procedures: Sampling by a spade and combined in a plastic bag.
- Sampling depth (cm): 0 - 20 cm
- Storage conditions: 20 °C
- Storage length: 8 days from sampling until pre-equilibration. Soil was pre-equilibrated at 20 °C until application (4 days).
- Soil preparation (e.g., 2 mm sieved; air dried etc.): soil was passed through a 2 mm sieve

PROPERTIES OF THE SOILS (in addition to defined fields)
- Moisture at 1/3 atm (%): 10.2, 20.7 and 31.7 [g H2O ad 100 g soil dwt] for the Laacher Hof AXXa, Hoefchen am Hohenseh 4a and Dollendorf II, respectively
- Bulk density (g/cm3): 1.27, 1.12 and 0.98 [gm/cm3] for the Laacher Hof AXXa, Hoefchen am Hohenseh 4a and Dollendorf II, respectively

Soil No.:

#1

Duration:

120 d

Soil No.:

#2

Duration:

120 d

Soil No.:

#3

Duration:

120 d

Soil No.:

#1

Initial conc.:

0.5 mg/kg soil d.w.

Based on:

act. ingr.

Soil No.:

#2

Initial conc.:

0.5 mg/kg soil d.w.

Based on:

act. ingr.

Soil No.:

#3

Initial conc.:

0.5 mg/kg soil d.w.

Based on:

act. ingr.

Parameter followed for biodegradation estimation:

CO2 evolution

radiochem. meas.

Soil No.:

#1

Temp.:

20.1

Humidity:

10.2 at 0.33 bar [g H2O ad 100 g soil DW]

Microbial biomass:

950 [mg microbial carbon / kg soil DW] DAT 0

Soil No.:

#2

Temp.:

20.1

Humidity:

20.7 at 0.33 bar [g H2O ad 100 g soil DW]

Microbial biomass:

836 [mg microbial carbon / kg soil DW] DAT 0

Soil No.:

#3

Temp.:

20.1

Humidity:

31.7 at 0.33 bar [g H2O ad 100 g soil DW]

Microbial biomass:

2419 [mg microbial carbon / kg soil DW] DAT 0

Details on experimental conditions:

1. EXPERIMENTAL DESIGN
- Soil preincubation conditions (duration, temperature if applicable):.Soil was pre-equilibrated at 20 °C until application (4 days). 8 days from sampling until pre-equilibration
- Soil condition:: air dried
- Soil (g/replicate): 100 g dwt/replicate
- Control conditions, if used (present differences from other treatments, i.e., sterile/non-sterile, experimental conditions):
- No. of replication treatments:3 soils x 2 replicates each soil
- Test apparatus (Type/material/volume): 300 mL glass Erlenmeyer flask
- Details of traps for CO2 and organic volatile, if any:Aerobic Study Phase: Each individual test flask was fitted with a separate trap
attachment, in which soda lime and a polyurethane (PU) foam plug were contained as
trapping media for carbon dioxide and organic volatile compounds, respectively. The
assembly was permeable to atmospheric oxygen. Two separate layers of soda lime
were used, allowing for the collection of 14CO2 emanating from the flasks without
interference from atmospheric CO2. The soda lime pellets incluincluded an indicator dye,
warning by color change in case of CO2 saturation of the pellets.

Anaerobic (Flooded) Study Phase: The test systems were closed with gas sampling
bags which allowed for analysis of the gaseous headspace formed upon anaerobic
incubation.

2. TEST MATERIAL APPLICATION
- Volume of test solution used/treatment: The test systems were treated with 400 μL application solution per flask,.
- Application method (e.g. applied on surface, homogeneous mixing etc.): The test substance solution was evenly distributed as small droplets applied directly onto the soil surface using an Eppendorf pipette
- Is the co-solvent evaporated: No

Any indication of the test material adsorbing to the walls of the test apparatus: No. The complete material balance found at all sampling intervals demonstrated that no significant portion of radioactivity dissipated from the flasks or was lost during processing.

3. EXPERIMENTAL CONDITIONS (in addition to defined fields)
- Moisture maintenance method:Addition of wagter where warranted. Water addition was not required
- Continuous darkness: Yes

4. OXYGEN CONDITIONS (delete elements as appropriate)
- Methods used to create the an/aerobic conditions: Aerobic conditions were maintained by passive diffusion of atmospheric oxygen through the volatiles trap attachments. Anaerobic conditions were maintained by the nitrogen gas atmosphere in the closed test flasks. In addition, before closing the test systems on DAT-15 (= DASF-0, DD) or DAT-29 (= DASF-0, AX and HH), the flooded soil in the closed test flasks was flushed vigorously with argon gas for 1 minute. To ensure absence of any interfering oxygen, the entire test systems were placed into a continuously nitrogen-flooded box in the incubation chamber
- Evidence that an/aerobic conditions were maintained during the experiment (e.g. redox potential): Oxygen content in the water layer decreased during the study from about 1.3 to 2.0 mg/L at DASF-0 to 0.2 to 0.7 mg/L at study end demonstrating the shift to anaerobic conditions. Redox potential measurements indicated reducing conditions in the soil layer and in the water layer from DASF-29 of the study onwards.

5. SAMPLING DETAILS
- Sampling intervals: For the aerobic incubation phase, test systems were processed at two sampling time points, DAT-0 and DAT-15 (soil DD) and DAT-29 (soils AX, HH), respectively. For the anaerobic incubation phase samples were collected at 8 dates, being DAT-15 and 18, 22, 29, 45, 73, 105 and 134, corresponding to 0, 3, 7, 14, 30, 58, 90 and 119 days after soil flooding (DASF) for test system DD. For test systems AX and HH samples were taken on DAT-29, 32, 37, 44, 59, 91, 120 and 150 days after treatment, corresponding to 0, 3, 8, 15, 30, 62, 91 and 121 DASF.
- Sampling method for soil samples: At each sampling interval, duplicate samples were processed and analyzed.
- Method of collection of CO2 and volatile organic compounds: Polyurethane (PU) Foam Plugs that were used to trap organic volatiles were extracted with 50 mL ethyl acetate each, under sonication for 30 min. Aliquots of the extracts were radioassayed by LSC.
The radioactivity (i.e. 14CO2) absorbed to the soda lime was liberated with 18% aqueous HCl and purged into LS cocktails with nitrogen. For this purpose aqueous HCl was added drop-wise to the 100-mL Erlenmeyer flask containing the soda lime, and liberated 14CO2 was carried by a stream of nitrogen for about 30 minutes whilst stirring. The 14CO2 was absorbed in a series of three LS vials each filled with 15 mL of icecooled scintillation cocktail Oxysolve C400 (Zinsser Analytic) which were afterwards subjected to LSC.
- Sampling intervals/times for:
> Sterility check, if sterile controls are used: Not applicable
> Moisture content: During the aerobic incubation phase of 15 days (soil DD) and 29 days (soils AX, HH) it was not necessary to adjust the moisture (weighing of sampled flasks indicated no significant losses. For the anaerobic incubation phase the soil was flooded and therefoer moisture maintenance was not required.
> Redox potential/other: In soil and water layer, at each anaerobic sampling interval.
> Sample storage before analysis: Typically direct analysis of all samples.

Soil No.:

#1

% Recovery:

99.4

St. dev.:

1.1

Soil No.:

#2

% Recovery:

99.5

St. dev.:

1.7

Soil No.:

#3

% Recovery:

101.6

St. dev.:

1.2

Key result

Soil No.:

#1

% Degr.:

>= 31.7 - <= 99.2

Parameter:

radiochem. meas.

Sampling time:

121 d

Key result

Soil No.:

#2

% Degr.:

>= 29.1 - <= 102.1

Parameter:

radiochem. meas.

Sampling time:

121 d

Key result

Soil No.:

#3

% Degr.:

>= 22.6 - <= 101.3

Parameter:

radiochem. meas.

Sampling time:

119 d

Key result

Soil No.:

#1

DT50:

124 d

St. dev.:

1.2

Type:

other: Double First Order in parallel

Temp.:

20 °C

Key result

Soil No.:

#2

DT50:

116 d

St. dev.:

0.7

Type:

other: Double First Order in Parallel

Temp.:

20 °C

Key result

Soil No.:

#3

DT50:

79 d

St. dev.:

0.5

Type:

other: Double First Order in Parallel

Temp.:

20 °C

Transformation products:

yes

No.:

#1

No.:

#2

No.:

#3

Details on transformation products:

- Formation and decline of each transformation product during test: Three major degradation products were identified during the study:test substance-carboxylic acid (max. aerobic: 31.2%AR at DAT-15; anaerobic: 44.2%AR at DAT-45); test substance-N-methyl-quinazolinone (max. aerobic: 12.6%AR at DAT-29; anaerobic: 34.7%AR at DAT-150) and test substance-N-methyl-quinazolinone-carboxylic acid ( max. aerobic: < LOD; anaerobic: 11.2%AR at DAT 134).

Evaporation of parent compound:

no

Remarks:

Formation of volatile organic compounds was not significant, values being < 0.1%AR at all sampling intervals in all soils.

Volatile metabolites:

no

Remarks:

Formation of volatile organic compounds was not significant, values being < 0.1%AR at all sampling intervals in all soils.

Residues:

yes

Details on results:

TEST CONDITIONS
- Aerobicity (or anaerobicity), moisture, temperature and other experimental conditions maintained throughout the study: Yes

MAJOR TRANSFORMATION PRODUCTS
- Range of maximum concentrations in % of the applied amount and day(s) of incubation when observed:
Total extractable residues decreased during the aerobic incubation phase (DAT-0 to DAT-29) from 99.2 to 96.6%AR in soil Laacher Hof AXXa, from 102.1 to 93.2%AR in soil Hoefchen am Hohenseh 4a and from 101.3 to 93.8%AR in soil Dollendorf II (DAT-0 to DAT-15).
Non-extractable residues (NER) increased during the aerobic incubation phase (DAT-0 to DAT-29) from 0.2 to 3.2%AR in soil Laacher Hof AXXa, from 0.3 to 4.7%AR in soil Hoefchen am Hohenseh 4a and from 0.9 to 5.5%AR in soil Dollendorf II (DAT-0 to DAT-15).
During the anaerobic incubation phase (DAT-29 (DASF-0) to DAT-134 (DASF-119)) TOTAL extractable residues decreased from 98.4 to 92.5%AR in soil Laacher Hof AXXa, from 95.4 to 90.2%AR in soil Hoefchen am Hohenseh 4a and from 99.6 to 95.2%AR in soil Dollendorf II (DAT-15 (DASF-0) to DAT-134 (DASF-119)).
During the anaerobic incubation phase (DAT-29 (DASF-0) to DAT-150 (DASF-121)) NERs further increased towards the end of the study to 7.8%AR in soil Laacher Hof AXXa, 10.4%AR in soil Hoefchen am Hohenseh 4a and to 7.6%AR in soil Dollendorf II (DAT-15 (DASF-0) to DAT-134 (DASF-119)).

TOTAL UNIDENTIFIED RADIOACTIVITY (RANGE) OF APPLIED AMOUNT:
The total unidentified radioactivity in the entire systems reached values not higher than 8.1% AR. The maximum level of individual unidentified minor degradation products in the entire systems was not higher than 5.2% AR

EXTRACTABLE RESIDUES: Day 0: 99.2%AR in soil Laacher Hof AXXa; 102.1%AR in soil Hoefchen am Hohenseh 4a; 101.3 in soil Dollendorf II
- % of applied amount at end of study period: 92.5%AR in soil Laacher Hof AXXa; 90.2%AR in soil Hoefchen am Hohenseh 4a; 95.2%AR in soil Dollendorf II

NON-EXTRACTABLE RESIDUES
- % of applied amount at day 0: 0.2%AR in soil Laacher Hof AXXa; 0.3%AR in soil Hoefchen am Hohenseh 4a; 0.9 in soil Dollendorf II
- % of applied amount at end of study period: 7.8%AR in soil Laacher Hof AXXa; 10.4%AR in soil Hoefchen am Hohenseh 4a; 7.6%AR in soil Dollendorf II

MINERALISATION
- % of applied radioactivity present as CO2 at end of study: During the aerobic phase, the maximum amount of 14CO2 was 0.1 to 0.4% AR. Formation of other volatile radioactivity was insignificant (< 0.1% AR) in the aerobic and anaerobic incubation phase of all soils tested.

VOLATILIZATION
- % of the applied radioactivity present as volatile organics at end of study: Formation of volatile organic compounds other than CO2 was insignificant as demonstrated by values of ≤ 0.1% AR at all sampling intervals.

Description of key information

Aerobic Biodegradation in soil (OECD 307):

DT50 soil: 18.4 – 183 days at 20 °C, M-465975-02-1

 

Anaerobic Biodegradation in soil (OECD 307):

DT50 soil: 79 – 124 days at 20 °C, M-478837-01-1

Key value for chemical safety assessment

Half-life in soil:

183 d

at the temperature of:

20 °C

Additional information

Aerobic Biodegradation in Soil:

The degradation and time-dependence of sorption of was investigated according to OECD guideline 307 in four soils (source: Laacher Hof AXXa – Monheim Germany, Dollendorf II – Blankenheim Germany, Hanscheiderhof - Monheim Germany and Hoefchen Am Hohenseh 4a – Burscheid Germany) under aerobic conditions in the dark in the laboratory for 119 days at 20 ± 2 °C (mean: 19.7 °C) and a soil moisture of 55 ± 5% (mean: 53.9%) of the maximum water holding capacity (M-465975-02-1). The study application rate was 54.9 µg/100 g soil (dry weight), equal to 0.5 mg test substance/kg soil (dry weight). Duplicate test systems were processed and analyzed at 0, 2, 6, 9, 16, 22, 29, 62, 91 and 119 days after treatment.

Overall mean material balance was 97.2% of applied radioactivity (%AR) for soil Laacher Hof AXXa, 98.5%AR for soil Dollendorf II, 98.0%AR for soil Hanscheiderhof and 98.0%AR for soil Hoefchen Am Hohenseh 4a.

The following maximum amounts of carbon dioxide were detected at DAT-119 (study end): 1.0%AR in soil Laacher Hof AXXa, 2.5%AR in soil Dollendorf II, 0.6%AR in soil Hanscheiderhof and 2.2%AR in soil Hoefchen Am Hohenseh 4a. Formation of volatile organic compounds was not significant, values being ≤ 0.1%AR at all sampling intervals in all soils.

Total extractable residues decreased from 94.3%AR at DAT-0 to 84.3%AR at DAT-119 in soil Dollendorf II, from 94.1%AR at DAT-0 to 91.9%AR at DAT-119 in soil Hanscheiderhof and from 94.1%AR at DAT-0 to 90.6%AR at DAT-119 in soil Hoefchen Am Hohenseh 4a. In soil Laacher Hof AXXa the extractable radioactivity remained constant over the period of incubation with 95.0%AR at DAT-0 and 94.4%AR at DAT-119.

Non-extractable residues (NER) increased from 0.2, 0.7, 0.3 and 0.3%AR at DAT-0 to maximum amounts of 5.2, 13.9, 9.3 and 8.1%AR at DAT-119 in soils Laacher Hof AXXa, Dollendorf II, Hanscheiderhof and Hoefchen Am Hohenseh 4a, respectively.

The amount of test substance in the soil extracts decreased from 91.2%AR at DAT-0 to 41.9%AR at DAT-119 in soil Laacher Hof AXXa, from 87.7%AR at DAT-0 to 4.9%AR at DAT-119 in soil Dollendorf II, from 92.1%AR at DAT-0 to 55.9%AR at DAT-119 in soil Hanscheiderhof and from 88.8%AR at DAT-0 to 17.1%AR at DAT-119 in soil Hoefchen Am Hohenseh 4a, respectively.

Besides the formation carbon dioxide, six major degradation products were identified. [Test substance]-quinazolinone-carboxylic acid was detected with maximum amounts of 6.5%AR at DAT-119 in soil Dollendorf II, [test substance]-N-methyl-quinazolinone with 14.6%AR at DAT-91 in soil Hoefchen Am Hohenseh 4a,[test substance]-amide with 6.9%AR at DAT-62 in soil Hanscheiderhof, [test substance]-carboxylic acid with 47.8%AR at DAT-62 in soil Dollendorf II, [test substance]-desmethyl-amide-carboxylic acid with 12.0%AR at DAT-119 in soil Hoefchen Am Hohenseh 4a and [test substance]-N-methyl-quinazolinone-carboxylic acid with 10.6%AR at DAT-119 in soil Dollendorf II. Furthermore, five minor degradation products were found with no component exceeding 3.5%AR at any sampling interval.

The experimental data could be well described by a double first order in parallel kinetic model for soil Laacher Hof AXXa (loamy sand) as well as by a first order multi compartment kinetic model for soils Dollendorf II (loam), Hanscheiderhof (silt loam) and Hoefchen Am Hohenseh 4a (silt loam).

The calculated half-lives of test substance under aerobic conditions were 94.4 days in soil Laacher Hof AXXa, 18.4 days in soil Dollendorf II, 183 days in soil Hanscheiderhof and 43.8 days in soil Hoefchen Am Hohenseh 4a.

The sorption of test substance to soil increased in the course of the study. The calculated RTDS values (Ratio of concentration of test item in soil [µg/g]/ concentration of test item in solution [µg/mL]) were 4.61, 11.69, 6.71 and 8.04 mL/g for soils Laacher Hof AXXa, Dollendorf II, Hanscheiderhof and Hoefchen Am Hohenseh 4a, respectively, at the beginning of the study (DAT-0). With time of aging in soil, RTDSvalues increased to 13.91, 38.62, 19.39, and 28.82 mL/g on DAT-119 for the four soils.

The formation of carbon dioxide indicates the potential for mineralization of the test item and its transformation products. Therefore, the substance is not expected to have a potential for accumulation in the environment.

 

Anaerobic Biodegradation in Soil

The degradation was investigated according to OECD guideline 307 in three soils (source: Laacher Hof AXXa – Monheim Germany, Dollendorf II – Blankenheim Germany, and Hoefchen Am Hohenseh 4a – Burscheid Germany) under anaerobic conditions in the dark in the laboratory for 120 days at 20 ± 2 °C (mean: 20.1 °C) applying an aerobic incubation phase of 15 days for soil Dollendorf II and 29 days for soils Laacher Hof AXXa and Hoefchen am Hohenseh 4a (soil moisture 55 ± 5% of the maximum water holding capacity) before the start of the anaerobic incubation phase (total study period 135 days for soil Dollendorf II and 149 days for soils Laacher Hof AXXa and Hoefchen am Hohenseh 4a) (M-478837-01-1). The study application rate was 53.3 µg/100 g soil (dry weight), equal to 0.5 mg test substance/kg soil (dry weight).

During the aerobic incubation phase, duplicate test systems were processed and analyzed at 0 and 15 days (soil Dollendorf II) or 29 days (soils Laacher Hof AXXa and Hoefchen am Hohenseh 4a) after treatment (DAT). During the anaerobic incubation phase, duplicate test systems were processed and analyzed at DAT-15, DAT-18, DAT-22, DAT-29, DAT-45, DAT-73, DAT-105 and DAT-134, corresponding to 0, 3, 7, 14, 30, 58, 90 and 119 days after soil flooding (DASF) for soil Dollendorf II. For soils Laacher Hof AXXa and Hoefchen am Hohenseh 4a duplicate test systems were processed and analyzed during the anaerobic incubation phase at DAT-29, DAT-32, DAT-37, DAT-44, DAT-59, DAT-91, DAT-120 and DAT-150, corresponding to 0, 3, 8, 15, 30, 62, 91 and 121 days after soil flooding (DASF).

Overall mean material balance was 99.4% of applied radioactivity (%AR) for soil Laacher Hof AXXa, 99.5%AR for soil Hoefchen am Hohenseh 4a and 101.6%AR for soil Dollendorf II.

The following maximum amounts of carbon dioxide were detected at DAT-15 or DAT-29 (end of aerobic incubation phase for soil: 0.1%AR in soil Dollendorf II, 0.3%AR in soil Laacher Hof AXXa and 0.4%AR in soil Hoefchen am Hohenseh 4a. Formation of volatile organic compounds was not significant, values being < 0.1%AR at all sampling intervals in all soils.

Total extractable residues decreased during the aerobic incubation phase (DAT-0 to DAT-29) from 99.2 to 96.6%AR in soil Laacher Hof AXXa, from 102.1 to 93.2%AR in soil Hoefchen am Hohenseh 4a and from 101.3 to 93.8%AR in soil Dollendorf II (DAT-0 to DAT-15). During the anaerobic incubation phase (DAT-29 (DASF-0) to DAT-134 (DASF-119)) total extractable residues decreased from 98.4 to 92.5%AR in soil Laacher Hof AXXa, from 95.4 to 90.2%AR in soil Hoefchen am Hohenseh 4a and from 99.6 to 95.2%AR in soil Dollendorf II (DAT-15 (DASF-0) to DAT-134 (DASF-119)).

Non-extractable residues (NER) increased during the aerobic incubation phase (DAT-0 to DAT-29) from 0.2 to 3.2%AR in soil Laacher Hof AXXa, from 0.3 to 4.7%AR in soil Hoefchen am Hohenseh 4a and from 0.9 to 5.5%AR in soil Dollendorf II (DAT-0 to DAT-15). During the anaerobic incubation phase (DAT-29 (DASF-0) to DAT-150 (DASF-121)) NERs further increased towards end of the study to 7.8%AR in soil Laacher Hof AXXa, 10.4%AR in soil Hoefchen am Hohenseh 4a and to 7.6%AR in soil Dollendorf II (DAT-15 (DASF-0) to DAT-134 (DASF-119)).

The amount of test substance in the entire system decreased during the aerobic incubation phase (DAT-0 to DAT-29) from 99.2 to 61.3%AR in soil Laacher Hof AXXa, from 102.1 to 60.6%AR in soil Hoefchen am Hohenseh 4a and from 101.3 to 51.7%AR in soil Dollendorf II (DAT-0 to DAT-29). During the anaerobic incubation phase (DAT-29 (DASF-0) to DAT-150 (DASF-121)) the amount of test substance in the entire system further decreased towards end of the study to 31.7%AR in soil Laacher Hof AXXa, 29.1%AR in soil Hoefchen am Hohenseh 4a and to 22.6%AR in soil Dollendorf II (DAT-15 (DASF-0) to DAT-134 (DASF-119)).

Three major degradation products were identified during the study: [test substance]-carboxylic acid (max. aerobic: 31.2%AR at DAT-15; anaerobic: 44.2%AR at DAT-45); [test substance]-N-methyl-quinazolinone (max. aerobic: 12.6%AR at DAT-29; anaerobic: 34.7%AR at DAT-150) and [test substance]-N-methyl-quinazolinone-carboxylic acid (max. aerobic: < LOD; anaerobic: 11.2%AR at DAT‑134).

The experimental data could be well described by a double first order in parallel kinetic model for all soils tested. The calculated half-lives of test substance under anaerobic conditions were 124 days in soil Laacher Hof AXXa, 116 days in soil Hoefchen am Hohenseh 4a and 79 days in soil Dollendorf II.

The results indicate that the substance is not expected to have a potential for accumulation in the terrestrial environment.