1,3,5-Triazine-2,4-diamine, N2-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-

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

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

other: US-EPA Pesticide Assessment Guidelines, Subdivision N, Environmental Fate, §162-2: Anaerobic Soil Metabolism Studies (1982).

Qualifier:

according to guideline

Guideline:

OECD Guideline 307 (Aerobic and Anaerobic Transformation in Soil)

GLP compliance:

yes (incl. QA statement)

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

anaerobic

Soil classification:

USDA (US Department of Agriculture)

Soil no.:

#1

Soil type:

silt loam

% Clay:

18.1

% Silt:

72.2

% Sand:

9.7

% Org. C:

2.8

pH:

6.5

CEC:

17.6 meq/100 g soil d.w.

Bulk density (g/cm³):

1.04

Soil No.:

#1

Duration:

180 d

Soil No.:

#1

DT50:

> 1 000 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: under anaerobic conditions

Transformation products:

no

Evaporation of parent compound:

no

Volatile metabolites:

no

Residues:

yes

Kinetics of Parent Compound Degradation:

Under aerobic conditions, AE 1170437 was fast metabolized. After 30 days

incubation, the remaining amount of parent was 55.1% (label A) and 60.6% (label B)

of AR. Then, conditions were changed from aerobic to anaerobic. Under these

anaerobic conditions, no further degradation of the AE 1170437 was observed.

Conclusion:

The test compound, AE 1170437, was found subject to degradation in a flooded

anaerobic soil environment under laboratory conditions. At first the test item was

incubated under aerobic conditions for 30 days. Under these conditions, AE 1170437

was metabolized and three metabolites were formed, which were already identified in

the aerobic soil metabolism studies. After flooding the system and displacement of

oxygen by argon, the test system became anaerobic. Under anaerobic conditions,

AE 1170437 and the metabolites formed under aerobic conditions remained

unchanged. No additional metabolite was formed in significant amounts under

anaerobic conditions.

This laboratory study showed that the test compound AE 1170437 is not degradable

in soil under flooded anaerobic conditions. The transformation products remained

unchanged. No metabolite is formed under anaerobic conditions.

Reference 2

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

key study

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: EC-Directive 91/414/EEC Annex I Part 7 and Annex II Part 9

Qualifier:

according to guideline

Guideline:

other: EPA-Guidelines for Aerobic Soil Metabolism Studies, § 162-1

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:

10

% Silt:

17

% Sand:

73

% Org. C:

1.3

pH:

6.8

CEC:

7.7 meq/100 g soil d.w.

Bulk density (g/cm³):

1.07

Soil no.:

#2

Soil type:

loam

% Clay:

22

% Silt:

34

% Sand:

44

% Org. C:

1

pH:

6.7

CEC:

9.1 meq/100 g soil d.w.

Bulk density (g/cm³):

1.06

Soil no.:

#3

Soil type:

sandy loam

% Clay:

16

% Silt:

30

% Sand:

54

% Org. C:

1.6

pH:

5.3

CEC:

8.9 meq/100 g soil d.w.

Bulk density (g/cm³):

1.02

Soil no.:

#4

Soil type:

loam

% Clay:

20

% Silt:

46

% Sand:

34

% Org. C:

2

pH:

6.7

CEC:

13 meq/100 g soil d.w.

Bulk density (g/cm³):

0.97

Soil No.:

#1

Duration:

120 d

Soil No.:

#2

Duration:

120 d

Soil No.:

#3

Duration:

120 d

Soil No.:

#4

Duration:

120 d

Soil No.:

#1

DT50:

51.6 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: LH AXXa

Soil No.:

#2

DT50:

29.8 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: LH AIIIa

Soil No.:

#3

DT50:

21.7 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: Wurmwiese

Soil No.:

#4

DT50:

42.1 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: Hoefchen a.H.

Transformation products:

yes

No.:

#1

No.:

#2

No.:

#3

Evaporation of parent compound:

no

Volatile metabolites:

no

Residues:

yes

The data gathered in the current laboratory investigation demonstrate, that the test item AE 1170437 was well degraded in all 4 soils with a DT50 of 21.7 to 51.6 days (20 °C) according to first order multi compartment kinetics. In the course of the experiment three major degradation products were detected and quantified together with the test item. AE 2158968 (report name: triazine indanone) increased to a maximum concentration of 15.8% of AR at DAT-38 in soil Wurmwiese. AE 2158969 (report name: carboxylic

acid) was max. 16.8% at DAT-59 in soil AIIIa. Both metabolites declined at the end of the study. The metabolite AE 1956114 (report name: diaminotriazine) was max. 31.6% of AR at DAT-120 in soil AIIIa. In the course of the experiment additionally up to 6 TLC zones indication degradation products were detected and quantified. The maximum amount of an unidentified zone was 2.5% of AR (Z6, DAT-120, soil Wurmwiese). Along with the overall metabolism of the test item, bound residues were formed. The portions of non-extracted residues were low at the beginning of the study (1.0% - 1.5% of AR) and increased to 17.1% - 24.6% at DAT-120.

The amount of 14CO2 increased over the entire study period. At the end of the study 5.0% - 30.6% of AR was quantified as carbon dioxide indicating the complete mineralization of AE 1170437.

The test item AE 1170437 will be degraded in soil under aerobic conditions. The DT50 in soil is expected to be in the range of 21.7 to 51.6 days. Three major metabolites were formed. The high amount of 14CO2 indicates the complete mineralization.

Reference 3

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

key study

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: EC-Directive 91/414/EEC Annex I Part 7 and Annex II Part 9

Qualifier:

according to guideline

Guideline:

other: EPA-Guidelines for Aerobic Soil Metabolism Studies, § 162-1

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:

9.9

% Silt:

17.5

% Sand:

72.6

% Org. C:

1.64

pH:

6.8

CEC:

7.3 meq/100 g soil d.w.

Bulk density (g/cm³):

1.15

Soil no.:

#2

Soil type:

loam

% Clay:

17.5

% Silt:

41.5

% Sand:

41

% Org. C:

1.29

pH:

7.1

CEC:

9.2 meq/100 g soil d.w.

Bulk density (g/cm³):

1.13

Soil no.:

#3

Soil type:

loam

% Clay:

15.8

% Silt:

36.9

% Sand:

47.3

% Org. C:

2.08

pH:

6.4

CEC:

9.6 meq/100 g soil d.w.

Bulk density (g/cm³):

1.1

Soil no.:

#4

Soil type:

silt loam

% Clay:

17.9

% Silt:

70.5

% Sand:

11.6

% Org. C:

2.07

pH:

7.2

CEC:

12.8

Bulk density (g/cm³):

1.09

Soil No.:

#1

Duration:

122 d

Soil No.:

#2

Duration:

122 d

Soil No.:

#3

Duration:

122 d

Soil No.:

#4

Duration:

122 d

Soil No.:

#1

DT50:

41.3 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: LH AXXa

Soil No.:

#2

DT50:

27.7 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: LH AIIIa

Soil No.:

#3

DT50:

27.9 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: Wurmwiese

Soil No.:

#4

DT50:

36.8 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: Hoefchen a.H.

Transformation products:

yes

No.:

#1

No.:

#2

Evaporation of parent compound:

no

Volatile metabolites:

no

Residues:

yes

The test item AE 1170437 (Radiolabel used: [indane-3-13/14C] AE 1170437) will be degraded in soil under aerobic conditions. The DT50 in soil is expected to be in the range of 27.7 to 41.3 days. The high amount of 14CO2 indicates the complete mineralization.

Reference 4

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

key study

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

GLP compliance:

yes (incl. QA statement)

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

aerobic

Soil classification:

not specified

Soil no.:

#1

Soil type:

sandy loam

% Clay:

8.4

% Silt:

25.9

% Sand:

65.7

% Org. C:

0.5

pH:

8.6

CEC:

9.7 meq/100 g soil d.w.

Bulk density (g/cm³):

1.23

Soil no.:

#2

Soil type:

sandy loam

% Clay:

15.6

% Silt:

7.8

% Sand:

76.6

% Org. C:

1.7

pH:

6.5

CEC:

6 meq/100 g soil d.w.

Bulk density (g/cm³):

1.13

Soil No.:

#1

Duration:

368 d

Soil No.:

#2

Duration:

368 d

Soil No.:

#1

Initial conc.:

600 g/ha d.w.

Based on:

act. ingr.

Soil No.:

#2

Initial conc.:

600 g/ha d.w.

Based on:

act. ingr.

Parameter followed for biodegradation estimation:

CO2 evolution

radiochem. meas.

Soil No.:

#1

% Recovery:

98.5

St. dev.:

4.8

Remarks on result:

other: In the California soil, the average material balance ranged from 89.6 to 108.9% of the applied radioactivity.

Soil No.:

#2

% Recovery:

98.6

St. dev.:

1.8

Remarks on result:

other: In the North Carolina soil, the average material balance ranged from 96.3 to 103.0% of the applied radioactivity.

Soil No.:

#1

DT50:

87.6 d

Type:

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

Temp.:

25 °C

Remarks on result:

other: - Locations of the label: [Indane-3-13C/14C]

Soil No.:

#2

DT50:

176 d

Type:

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

Temp.:

25 °C

Remarks on result:

other: - Locations of the label: [Indane-3-13C/14C]

Transformation products:

yes

No.:

#1

No.:

#2

Evaporation of parent compound:

no

Volatile metabolites:

no

Residues:

yes

Under aerobic conditions, the substance mineralizes to CO2 (37.2 % California, 17.8% North Carolina by study end). The substance steadily degraded to either AE 1170437- carboxylic acid (17.2% maximum on day 123 in the California soil and 9.9% maximum on day 122 in North Carolina soil) or AE 1170437-triazine indanone (9.2% maximum on day 26 in the California soil and 16.7% maximum on day 122 in North Carolina soil). The DT50 of parent was 87.6 days in the California soil (1#) and 176 days in the North Carolina soil (2#).

An aerobic soil environment will have a significant contribution to the overall degradation of AE 1170437. The parent compound is oxidized to either AE 1170437 -triazine indanone or AE 1170437-carboxylic acid which are further mineralized to CO2.

AE 1170437 is also dissipated through the formation of bound residues.

Reference 5

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

supporting study

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)

GLP compliance:

yes (incl. QA statement)

Test type:

laboratory

Oxygen conditions:

aerobic

Soil no.:

#1

Soil type:

silt loam

% Clay:

18.3

% Silt:

72

% Sand:

9.7

% Org. C:

1.77

pH:

7.22

CEC:

16.1 meq/100 g soil d.w.

Bulk density (g/cm³):

2.591

Soil no.:

#2

Soil type:

loam

% Clay:

16.5

% Silt:

34.1

% Sand:

49.4

% Org. C:

1.5

pH:

5.96

CEC:

12.3 meq/100 g soil d.w.

Bulk density (g/cm³):

2.598

Details on soil characteristics:

SOIL COLLECTION AND STORAGE
Test soils Hoefchen 'Am Hohenseh 4a' and Laacher Hof 'Wurmwiese' were chosen to
represent typical agricultural soils of European origin. Texture shows variation
including loam and silt loam type, and physico-chemical characteristics were not
extreme in any parameter. Pesticide history of the collection sites is documented
over more than five years (none used).

Soil No.:

#1

Duration:

120 d

Soil No.:

#2

Duration:

120 d

Parameter followed for biodegradation estimation:

test mat. analysis

Transformation products:

no

The test items AE 1170437 and AE 1170438 were found subject to similarly rapid

degradation in a typical soil environment under aerobic laboratory conditions. In this

study the concentration of AE 1170437 remaining was slightly lower to its

diastereomer AE 1170438, the difference was not significant. The two

diastereoisomers therefore showed comparable degradation behaviour in soil.

At study end the residue levels in the soil

Hoefchen 'Am Hohenseh 4a' were 18.9 and 23.5% of the applied for AE 1170437

and AE 1170438, respectively. At study end the residue levels in the soil Laacher Hof

'Wurmwiese' were 33.7 and 39.6% of the applied for AE 1170437 and AE 1170438,

respectively.

Reference 6

Endpoint:

biodegradation in soil: simulation testing

Type of information:

experimental study

Adequacy of study:

key study

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

GLP compliance:

yes (incl. QA statement)

Test type:

laboratory

Radiolabelling:

yes

Oxygen conditions:

aerobic

Soil classification:

not specified

Soil no.:

#1

Soil type:

sandy loam

% Clay:

8.4

% Silt:

25.9

% Sand:

65.7

% Org. C:

0.5

pH:

8.6

CEC:

9.7 meq/100 g soil d.w.

Bulk density (g/cm³):

1.23

Soil no.:

#2

Soil type:

sandy loam

% Clay:

15.6

% Silt:

7.8

% Sand:

76.6

% Org. C:

1.7

pH:

6.5

CEC:

6 meq/100 g soil d.w.

Bulk density (g/cm³):

1.13

Soil No.:

#1

Duration:

368 d

Soil No.:

#2

Duration:

368 d

Soil No.:

#1

Initial conc.:

600 g/ha d.w.

Based on:

act. ingr.

Soil No.:

#2

Initial conc.:

600 g/ha d.w.

Based on:

act. ingr.

Parameter followed for biodegradation estimation:

CO2 evolution

Soil No.:

#1

Temp.:

25 °C

Microbial biomass:

107 mg C/kg (dry basis)

Soil No.:

#2

Temp.:

25 °C

Microbial biomass:

228 mg C/kg (dry basis)

Soil No.:

#1

% Recovery:

96.5

St. dev.:

2.2

Remarks on result:

other: California soil

Soil No.:

#2

% Recovery:

99.5

St. dev.:

1.9

Remarks on result:

other: North Carolina soil

Soil No.:

#1

DT50:

82.2 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: California soil

Soil No.:

#2

DT50:

146 d

Type:

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

Temp.:

20 °C

Remarks on result:

other: North Carolina soil

Transformation products:

yes

No.:

#1

No.:

#2

No.:

#3

Evaporation of parent compound:

no

Volatile metabolites:

no

Residues:

yes

Under aerobic conditions, AE 1170437 oxidizes to AE 1170437-diaminotriazine (37.9 % by study end in California soil, 20.8% maximum on Day 122 in North Carolina soil), AE 1170437-carboxylic acid (16.5% maximum on day 26 in the California soil and 9.0% maximum on day 122 in North Carolina soil) and AE 1170437-triazine indanone (9.5% maximum on day 26 in the California soil and 14.5% maximum on day 122 in North Carolina soil). AE 1170437 is also mineralized to CO2 (14.0% California, 3.5% North Carolina by study end) and dissipated to form non-extractable residues (18.2% California, 34.1% North Carolina by study end). The DT50 of parent was 82.2 days in the California soil and 146 days in the North Carolina soil.

Description of key information

Aerobic Biodegradation in soil (OECD 307)

DT50 soil: 22-177 days at 20-25 °C

Anaerobic Biodegradation in soil (OECD 307)

DT50 soil: > 365 days at 20-25°C

Additional information

The behaviour of the substance has been extensively investigated in several studies. The objective of the studies was to determine the metabolic pathway, degradation rate and half-life 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 metabolites including 14CO2 and bound residues were quantified to establish material balances.

An aerobic soil environment will have a significant contribution to the overall degradation of the substance. The substance is oxidized to degradation products which were further mineralized to CO2. The half-lives in aerobic soils (DT50) of the substance were between 22 – 177 days (mean values of 25 -161 days) in the different soils (4 EU soils and 2 US soils).

An additional anaerobic study investigates the biotic degradation under anaerobic conditions. Indaziflam was found to be subject to degradation in a flooded anaerobic soil environment under laboratory conditions. This laboratory study showed that the inaziflam is not degradable in soil under flooded anaerobic conditions. The transformation products remained unchanged. No metabolites were formed under anaerobic conditions.

Summary of DT50 for indaziflam in Aerobic Soil:

Test substance			Aerobic Soil Conditions
Soil Type	Label	pH 1	t,°C/ % MWHC	DT50	Method of Calculation
Sandy Loam	Mean of both labels	8.6/7.9	25°C/33.2 %	85	Single first order (SFO)
Sandy Loam	Mean of both labels	6.5/5.4	25°C/26.3 %	161	SFO
Sandy loam	Mean of both labels	6.8/6.5	20°C/46.7 %	46	Single first order in parallel kinetics (FOMC)2 Double First Order in Parallel (DFOP)3
Loam	Mean of both labels	6.7/6.3	20°C/51.6 %	29	FOMC DFOP
Sandy Loam	Mean of both labels	5.3/5.0	20°C/56.6 %	25	FOMC DFOP
Loam	Mean of both labels	6.7/6.3	20°C/64.3 %	39	FOMC DFOP

1)pH in water/pH in 0.01 M CaCl2

2) Indane label

3) Triazine label