### Test Material: Sulfentrazone

MRID: 48958902

T it le: Keenan, D.J. and A. DePompei. 2012. [ 14 

### C]Sulfen tr azone: Aerobic Aquatic Sediment Metabolism.

EPA PC Code: 129081

OCSPP Guideline: 835.4300

For CDM Smith:

Primary Reviewer: Dana Worcester Signature:

# ~~**{.;)~ ·** 

Date: 11 / 12 / 13



### Secondary Reviewer: Kathleen Ferguso n Signature:

# 'i(~f'**~**

Date: 11112 / 1 3

QC/QA Manager: J oan Gaidos

For the Environmental Protection Agency:

Final Reviewer: Michael Barrett 

### Signature: 

# /J/.

Date: 11 / 12 /13

Date: 9112 / 2014Sulfentrazone (PC 129081 ) MRID 48958902

Page 2 of 22 

### Aerobic Degradation of Sulfentrazone in Aquatic Systems

Report: MRID 4 8958902

. Keenan, D.J. and A. DePompei. 2012. [ 14 

### C]Sulfentrazone:

Aerobic Aquatic Sediment Metabolism

. U npublished study performed by Ricerca Biosciences, LLC, Concord, Ohio ; sponsored and submitted by FMC Corporation, Ewing, New Jersey. Ricerca Study No.: 028157

. FMC Study No.:

162E2211E1. FMC Report No.: PC

- 0781. Experiment started October 28, 2011

and ter minated February 13, 2012 (p. 18). Final report issued September 18,

20 1 2

. Document No.: MRID 4 8958902

Guideline: OCSPP 835.4 3 00

Statements: The study was conducted according to USEPA Principles of Good Laboratory

Practice (p. 3) . Signed and dated Data Confidentiality, GLP, and Quality Assurance statements were provided (pp. 2

- 4). The authenticity of the study report is certified in the Quality Assurance Statement.

Classification: This study is classified as supplemental

. Posttreatment r edox potentials

,

d issolved oxygen content, and pH of the test systems were not reported

. Limits of Detection and Quantitation were not reported. Additional details on data limitations that would be required to upgrade the study are provided in the

“ Study Deficiencies, Re viewer's Comments, and Data Needs ” section.

PC Code: 1 29081

Reviewer: Michael R. Barrett

U.S. EPA Date: September 12 , 2014

E xecutive S ummary

The a erobic transformation of [ phenyl

14 

### C]

- and [carbonyl

14 

### C]

- labeled sulfentrazone was studied

in a California pond water : silty clay loam sediment system (sediment pH 6.1

, organic matter 5.1 % )

and a California canal water : sandy loam sediment system (sediment pH 6.0

, organic matter 2.1 %)

for 100 days in a closed system in the dark at 20  C. Th e systems w ere treated at 0. 164

- 0.176 mg a.i./ L

. It was unknown if aerobic conditions were maintained, since redox potentials were not reported

. Microbial population determinations of untreated sediments indicated the systems were viable at study initiation and termination

.

In the pond water : silty clay loam sediment system (combined labels), the o verall mass balances

were 9 4.7

- 110.0 % of the applied

. In the canal water : sandy loam sediment system (combined labels),

the o verall mass balances were 94.7

- 108.4 % of the applied. There was some decline in recoveries during the experiments

.

Observed DT 50 

### values, calculated half

- lives, and information on transformation pro ducts are listed

in Table 1

. Rates and patterns of d issipation of sulfentrazone were comparable between the two

sediments.

In the pond water : silty clay loam sediment (both labels)

, residues in the water decreased from 98.5

- 104.6% of the applied at time 0 to 49.9

- 58.6% at 100 days. E x tractable soil residues increased from

2.5

- 2.7 % of the applied at day 0 to 42.0

- 5 3.1 % at 70 days and w ere 41.7

- 43.8 % at 100 days.

Unextracted radioactivity increased from 1.6

- 2.8 % of the applied at day 0 to 5.4

- 9.2% at 14 day sSulfentrazone (PC 129081 ) MRID 48958902

Page 3 of 22 

### and was 7 .3

- 7.7 % at 100 days. Total evolved 14 

### CO 2 

### totaled 0.1

- 0.3% of the applied at 100 days; volatile organics were 0.1%.

In the canal water : sandy loam sediment (both labels)

, residues in the water decreased from 99.0

- 100.9% of the applied at time 0 to 60.0

- 60.9% at 100 days. E xtractable soil residues increased from

2.4

- 2.7 % of the applied at day 0 to 3 3.1

- 37.4 % at 70 days and were 3 1. 9

- 36.0 % at 100 days.

Unextracted radioactivity increased from 1.7

- 3.2 % of the applied at day 0 to 6. 9

- 9.3 % at 100 day s

. Total evolved 14 

### CO 2 

### totaled 0.1

- 0.9 % of the applied at 100 days; volatile organics were 0.2

- 0.9 %.

Table 1. Results S ynopsis: Aerobic Aquatic Metabolism of Sulfentrazone in the Total System

Total System Observed

DT 50 ( days ) Calculated

Half

- life ( days ) 1 Model

Parameters and

Statistics Transformation Products Common Name

( maximum % of a pplied observed,

associated interval )

Major Minor

California

P ond water : silty clay loam sediment (20oC, sediment pH 6.1 ) >100 679

SFO C 0 = 100

k = 0.00102

S

c = 425

S SFO = 3 86 None SCA ( 1.0 % at 100 days) HMS (1.2 % at 100 days)

CO 2 (0.3% at 100 days)

California

C anal water : sandy

loam sediment system (20oC, sediment pH 6.0 ) >100 612

SFO C 0 = 100

k = 0.00113

S

c = 202

S SFO = 185 None SCA (1.3% at 100 days) HMS (1.4% at 100 days)

CO 2 ( 0.9% at 100 days)

1 Calculated half

- lives and model parameters selected in accordance with N AFTA kinetics guidance (USEPA, 201 2 ) ; Simple First Order (SFO)

.



### I. Materials and Methods

A. Materials

1. Test Material: [ P henyl

- U

14 

### C]

- and [carbonyl

14 

### C]

- labeled s ulfentrazone (p. 19, Appendix 6, pp. 139

- 140). Phenyl Specific activity: 22.9 mCi/mMol (p. 19, Appendix 6,

p. 139) Radiochemical purity: 98.3% Chemical purity: Not reported

Lot No.: 54175

- 2

- 22Sulfentrazone (PC 129081 ) MRID 48958902

Page 4 of 22 

### Carbonyl Specific activity: 30.6 mCi/mMol (p. 20, Appendix 6,

p. 140). Radiochemical purity: 99.5% Chemical purity: Not reported.

Lot No.: 54175

- 1

- 22

Solubility in water: Not reported

2. Reference Compounds: The following compound s w ere used in the analysis

.

Table 2. Reference Compounds

Applicant’s Code Name (synonyms) Chemical Name Purity (%) Lot No.

Sulfentrazone N

- [2, 4

- D ichloro

- 5

- [4

- difluoromethyl

- 4,5

- dihydro

3

- methyl

- 5

- oxo

- 1H

- 1,2,4

- triazol

- 1

- yl]phenyl]methanesulfonamide -- E9337:19

Sulfentrazone

- 3

- carboxylic acid (SCA) 1

- [2,4

- D ichloro

- 5

- [N(methylsulfonyl)amino

phenyl]

- 4

- difluoromethyl

- 4,5

- dihydro

- 5

- oxo

- 1H

1,2,4

- triazol

- 3

- carboxylic acid -- SU

- 4

3

- Desmethyl sulfentrazone (DMS) 1

- [2,4

- D ichloro

- 5

- (N

- (methylsulfonyl)amino

phenyl]

- 4

- difl uoromethyl

- 1H

- 1,2,4

- triazol

- 5(4H)

-

one -- SU

- 24

3

- Hydroxymethyl

- sulfentrazone (HMS) 1

- [2,4

- D ichloro

- 5

- (N

- (methylsulfonyl)amino

phenyl]

- 4

- difluoromethyl

- 3

- hydroxy

- methyl

- 1H

1,2,4

- triazol

- 5(4H)

- one -- SU

- 29

Methyl triazole 4

- D ifluoromethyl

- 5

- methyl2,4

- dihydro[1,2,4]

- triazole

- 3

- one -- SU

- 32

Data obtained from pp. 20

- 22 of the study report.



### 3. Water: Sediment : Water and sediment collection and characterization are summarized in Table

3 and Tables 4a

- 4 b

, respectively.

Table 3. Water : Sediment Collection and Storage

Description Pond water : sediment Canal water:sediment

Geographic location California

Pesticide use history at the

collection site Not reported.

Collection date Not reported, received October 10, 2011

Collection procedures Water: In accordance with ISO 10381

- 6

Sediment: In accordance with ISO 10381

- 6

Storage conditions Stored in a dark incubator at 4 ± 2 C  ̊

Storage length Not reported, ca. 3 weeks based on date of receipt and experimental start date (October 28, 2011)

Preparation Water: Not reported.

Sediment: Wet sieved (2.0 mm)

. Data obtained from p p. 1 8, 22

- 23 of the study report.Sulfentrazone (PC 129081 ) MRID 48958902

Page 5 of 22 

### Table 4a. Parameters for Characterization of Pond Water:Sediment Sample s

Parameter (unit) Field Sampling/Post Handling Stage of Test Procedure

Prior to Test During Test End of Test

Water Temperature ( o C ) Not reported
pH Not reported TOC (mg/L) 2.9

Microbial biomass: Not reported

O 2 Not reported Redox potential (E h , mV) Not reported

Sediment Sampling Depth Not reported
pH ( 1:1 sediment:water ) 6.1
Soil Texture (USDA) Silty clay loam

Particle Size Distribution 16 % sand

50 % silt

34 % clay Organic matter (%) 5.1 CEC (meq/100 g) 15.5 Microbial biomass (μg/g)

-- 484.6 17.4 Redox potential (E h , mV) Not reported

Data obtained from p. 23; Table 1, p. 38; and Appendix 3, p p

. 123

- 1 26 of the study report. Soil texture confirmed by the reviewer using USDA

- NRCS technical support tools.

-- = Not reported.



### Table 4b. Parameters for Characterization of Canal Water:Sediment Samples

Parameter (unit) Field Sampling/Post Handling Stage of Test Procedure

Prior to Test During Test End of Test

Water Temperature ( oC) Not reported
pH Not reported TOC (mg/L) 3.0

Microbial biomass Not reported

O 2 Not reported Redox potential (E h , mV) Not reported

Sediment Sampling Depth Not reported pH ( 1:1 sediment:water ) 6.0
Soil Texture (USDA) Sand y loam

Particle Size Distribution 60 % sand

31 % silt

9 % clay Organic matter (%) 2.1 CEC (meq/100 g) 6.8 Microbial biomass (μg/g)

-- 55.8 34.9 Redox potential (E h , mV) Not reported

Data obtained from p. 30 ; Table 2, p. 39; and Appendix 3, p.. 127

- 130 of the study report. Soil texture confirmed by the reviewer using USDA

- NRCS technical support tools.Sulfentrazone (PC 129081 ) MRID 48958902

Page 6 of 22 

### B. S tudy Design

1. Experimental Conditions: Table 5 summarizes the experimental conditions.

Table 5. Experimental Design

Experimental Design Pond water:sediment Canal water:sediment

Duration of the test 100 days

Water : Type and size of filter used Not reported
Amount of sediment and water per treatment :

Water Volume: ca . 178 mL

Depth: Water was added to a height of 10 cm.

Sediment Weight: ca. 65 g dry wt. ca. 70 g dry wt.

Depth: 2.5 cm.

Water/sediment ratio Volume:Weight 2.7:1 (178 mL water: 65 g dry wt. sediment). 2.5 :1 ( 178 mL water: 7 0 g dry wt. sediment).

Depth: 4 :1

Application rates :

Nominal 0.139 μ g a.i./ mL

Actual Phenyl: 0.171 μg a.i./ mL Carbonyl: 0.164 μg a.i./mL Phenyl: 0.176 μg a.i./mL Carbonyl: 0.169 μg a.i./mL
Number of replicates:

Control, if used Sterile controls were not used.

Treated Duplicate s ample s per system were collected at each sampling interval

. Test apparatus:

Type/material/volume Nonsterile: Wide

- mouth glass bottles ( ca . 250 mL ), each separately connected to a

continuous flow

- through volatiles trapping system

. Sterile: Sterile controls were not used.
Details of traps for CO 2 and organic volatile, if

any Humidified air was pulled over the test system, then through o ne tube

of ethylene glycol and two tubes of 1N NaOH

. If no traps were used, is the system closed? Nonsterile: Volatile traps were used.

Sterile: Sterile controls were not used
Identity and final concentration (based on water volume) of co

- solvent None, water

Test material application method:

Volume of the test solution used/treatment 1 m L (1000  L)/sample (application rate based on 175

- 180 mL water

in sample)
Application method ( i.e. , mixed/not mixed) The test solution was applied to the water surface via glass pipette
Any indication of the test material adsorbing to the walls of the test apparatus? No

Microbial biomass/population of treated (units): Not determined in treated systems.

Water

-- Sediment

-- Experimental conditions:

Temperature: 20 ± 2°C, graphical data appears to show several deviations
Continuous darkness (yes/no) Yes

Other details (if any) The water:sediment systems were acclimated to test conditions for 9 days prior to treatment.

Data obtained from p p. 23

- 25 ; Table 3, p

. 40 ; and Appendix 4

, p p. 131

- 13 6 of the study report.Sulfentrazone (PC 129081 ) MRID 48958902

Page 7 of 22 

### 2. Sampling during Study Period : Table 6 summarizes sampling during the study period.

Table 6. Sampling during Study Period

Parameter Details

Sampling intervals (duration) Nonsterile: 0, 14 , 30, 45, 70, and 100 days posttreatment

Sterile controls: Sterile controls were not used.

Sampling method D uplicate s ample s w ere colle cted at each sampling interval

. Method of collection of CO 2 and organic volatile compounds Respective volatile traps were collected at each samplin g interval

.

Sampling Intervals/Times

Temperature

Not reported Redox potential in water layer

Dissolved oxygen in water layer

pH in water layer

Redox potential in sediment

pH in sediment Not determined.

Other details, if any Samples not analyzed immediately were stored at <

- 5 ̊C

Data obtained from p p

. 2 5

- 27 of the study report.



### 3. Analytical Procedures:

Separation of the W ater and S ediment : The water layer was separated from the sediment by decanting (p. 27 ).

Extraction/ C lean U p/ C oncentration M ethods: Water was analyzed directly by LSC and HPLC ( p. 27 ).

S ediment was extracted once with acetonitrile and twice with acetonitrile:water (80:20, v:v) by shaking at room temperature (p. 2 8 ). Resulting extracts were analyzed for total radioactivity by LSC. The acetonitrile extract was concentrated under a stream of nitrogen and analyzed by HPLC; the acetonitrile:water extract was apparently not furt her analyzed.

Determination of U nextracted R esidues: Extracted s ediment was analyzed for total radioactivity by LSC following combustion ( p

. 28 ).

Determination of V olatile Residues : Aliquots of the trapping solutions were analyzed for total radioactivity using LSC (p. 25). The presence of CO 2 

### was not confirmed.

Total R adioactivity M easurement: T otal [ 14 

### C ] residues were determined by summing the

concentrations of residues measured in the water layer, s ediment extracts, extracted s ediment and

volatiles trapping solutions ( p. 3 0 )

.

Derivatization M ethod : None reported

.

Identification and Q uantification of P arent C ompound and Transformation Products : W ater layer and acetonitrile:water sediment e xtract samples were analyzed by HPLC using a Luna C 18Sulfentrazone (PC 129081 ) MRID 48958902

Page 8 of 22 

### column eluted with a gradient mobile phase of (A) 0.01M ammonium acetate in water or water and (B) acetonitrile (p. 27). A second confirmatory method was not utilized.

Detection Li mits (LOD, LOQ) for the P arent Compound and Transformation Products : Limits of detection (LOD) and quantitation (LOQ) w ere not reported.

II. R esults and Discussion

A. Data :

Study results, including total mass balances and distribution of radioactivity, are presented in

Tables 7a and 7 d

. T he incubation temperature was reported as 20 ± 2 oC (p. 24). Graphical data appears to show deviations from the range (Appendix 4, pp. 131

- 132). Microbial population

determinations of untreated sediments indicated the systems were viable at study initiation and termination ( Appendix 3, pp. 125

- 126, 129

- 130 ). D issolved oxygen , redox potentials and pH results were not reported.

B. Mass Bal ance:

In the pond water:silty clay loam sediment system treated with the phenyl label , the o verall mass balances range was 96.4

- 1 10.0 % of the applied (Table 3, p. 41)

. In the pond water:silty clay loam sediment system treated with the carbonyl label, the o verall mass balances range was 94.7

- 102.5% of the applied (Table 8, p. 43).

In the canal water:sandy loam sediment system treated with the phenyl label , the o verall mass balances range was 99.9

- 108.4 % of the applied (Table 6, p. 42)

. In the canal water:sandy loam sediment system treated with the carbonyl label, the o verall mass balances range was 94.7

- 104.5% of the applied (Table 10, p. 44). The recoveries met guideline requirements in both water:sediment

systems.

C. Bound and Extractable Residues:

In the pond water:silty clay loam sediment treated with the phenyl label

, extractable radioactivity increased from 2.7% of the applied at day 0 to 53.1% at 70 days and was 41.7% at 100 days (Table 4, p. 41) . Unextracted radioactivity increased f rom 2.8% of the applied at day 0 to 9.2% at 14 days and was 7.3% at 100 days.

In the pond water:silty clay loam sediment treated with the carbonyl label

, extractable radioactivity increased from 2.5% of the applied at day 0 to 43.8% at 100 days (Table 8, p. 43) . Unextracted radioactivity increased from 1.6% of the applied at day 0 to 7.7% at 100 days.

In the canal water:sandy loam sediment treated with the phenyl label

, extractable radioactivity increased from 2.7% of the applied at day 0 to 37.4% at 70 days and was 36.0% at 100 days (Table 6, p. 42) . Unextracted radioactivity increased from 3.2% of the applied at day 0 to 9.3% at 100 days.Sulfentrazone (PC 129081 ) MRID 48958902

Page 9 of 22 

### In the pond water:sandy loam sediment treated with the carbonyl label

, extractable radioactivity

increased from 2. 4% of the applied at day 0 to 33.1% at 70 days and was 31.9% at 100 days (Table 10, p. 44) . Unextracted radioactivity increased from 1.7% of the applied at day 0 to 6.9% at 100 days.

D. Volatilization:

Evolved 14 

### CO 2 

### totaled a maximum 0.2

- 0.3 % in the pon d water:silty c lay loam sediment systems (Table 4 , p. 41 ; Table 8, p. 43). Volatile organics were 0.1%.

Evolved 14 

### CO 2 

### totaled a maximum 0.1

- 0.9% in the canal water:sandy loam sediment systems (Table 6 , p. 42 ; Table 10, p. 44). Volatile organics were 0.2

- 0.9%.Sulfentrazone (PC 129081 ) MRID 48958902

Page 10 of 22 

### Table 7 a

. Transformation of [phenyl

14 

### C]sulfentrazone, expressed as a percentage of applied radioactivity in aerobic water:silty clay

loam sediment

Sampling Interval (days) 0 14 30 45 70 100
Replicate 1 2 1 2 1 2 1 2 1 2 1 2

Sulfentrazone 107.2 106.5 100.0 97.9 92.9 102.3 94.3 97.3 97.3 94.6 93.5 99.6

SCA 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

HMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

DMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

Extractables 2.7 1.9 25.8 25.4 32.9 36.1 44.2 39.1 41.3 53.1 41.7 41.0

Water 104.5 104.6 74.2 72.5 60.0 66.2 50.2 58.2 56.4 42.4 51.9 58.6

Unextracted residues 2.8 2.8 8.8 9.2 3.3 4.7 5.8 4.7 5.5 7.5 7.3 6.9

CO 2 na na 0.1 0.1 0.1 0.1 0.2 0.2 0.2 0.2 0.3 0.3
Volatile organics na na 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.1 0.1

Mass balance 110.0 109.2 108.9 107.1 96.4 107.1 100.4 102.3 103.6 103.3 101.3 106.8

Dat a obtained from Table 4, p. 41 and Table 28, p. 53 of the study report

. na = Not applicable



### Table 7b. Transformation of [carbonyl

14 

### C]sulfentrazone, expressed as a percentage of applied radioactivity in aerobic water:silty clay loam sediment

Sampling Interval (days) 0 14 30 45 70 100
Replicate 1 2 1 2 1 2 1 2 1 2 1 2

Sulfentrazone 101.0 99.5 95.9 96.1 92.8 90.9 91.7 92.8 91.1 93.9 86.1 97.0
Methyl triazole 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

SCA 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.0 1.5

HMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.8 1.2

DMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

Extractables 2.5 2.4 24.5 26.0 34.2 34.9 39.7 37.4 42.0 41.0 43.8 38.7

Water 98.5 97.1 71.4 70.1 58.7 56.1 52.0 55.5 49.4 52.9 44.1 49.9

Unextracted residues 1.5 1.6 5.2 5.4 4.4 4.0 5.3 4.7 5.3 6.2 6.7 7.7

CO 2 na na 0.1 0.1 0.2 0.2 0.1 0.1 0.1 0.1 0.1 0.1
Volatile organics na na 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.1 0.1

Mass balance 102.5 101.1 101.2 101.6 97.4 95.1 97.1 97.6 96.9 100.3 94.7 96.5
Data obtained from Table 8, p. 43 and Table 32, p. 55 of the study report

. na = Not applicableSulfentrazone (PC 129081 ) MRID 48958902

Page 11 of 22 

### Table 7c. Transformation of [phenyl

14 

### C]sulfentrazone, expressed as a percentage of applied radioactivity in aerobic water:sandy

loam sediment.

Sampling Interval (days) 0 14 30 45 70 100

Replicate 1 2 1 2 1 2 1 2 1 2 1 2

Sulfentrazone 102.1 101.0 100.5 101.1 93.7 95.6 96.4 94.5 94.5 96.8 94.2 90.7

SCA 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

HMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

DMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

Extractables 2.7 2.0 20.6 22.4 26.6 31.3 36.2 28.8 33.5 37.4 36.0 29.8

Water 99.3 99.0 79.9 78.7 70.5 65.7 60.2 65.7 61.4 59.7 58.2 60.9

Unextracted residues 3.2 2.2 7.8 6.7 3.0 5.6 6.2 4.8 5.9 6.6 9.1 9.3

CO 2 na na 0.2 0.2 0.3 0.3 0.5 0.5 0.5 0.5 0.9 0.9

Volatile organics na na 0.0 0.0 0.0 0.0 0.1 0.1 0.2 0.2 0.9 0.9

Mass balance 105.3 103.2 108.4 108.1 100.5 102.9 103.1 99.9 101.5 104.5 105.1 101.8 Data obtained from Table 6, p. 42 and Table 30, p. 54 of the study report. na = Not applicableSulfentrazone (PC 129081 ) MRID 48958902

Page 12 of 22 

### Table 7d. Transformation of [carbonyl

14 

### C]sulfentrazone, expressed as a percentage of applied radioactivity in aerobic water:sandy

loam sediment.

Sampling Interval (days) 0 14 30 45 70 100

Replicate 1 2 1 2 1 2 1 2 1 2 1 2

Sulfentrazone 102.0 103.0 96.8 94.9 92.1 93.8 92.4 91.1 93.6 93.3 84.8 87.3

Methyl triazole 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

SCA 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.3 1.0

HMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 1.4 1.2

DMS 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

Extractables 2.4 2.1 18.8 21.0 25.8 26.9 32.1 29.8 33.1 31.5 31.9 29.5

Water 99.6 100.9 78.0 73.9 66.3 66.9 60.3 61.3 60.8 62.0 55.6 60.0

Unextracted residues 1.7 1.5 5.1 4.5 3.8 3.6 4.8 4.8 6.6 5.3 6.9 6.0

CO 2 na na 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1

Volatile organics na na 0.0 0.0 0.0 0.0 0.0 0.0 0.1 0.1 0.2 0.2

Mass balance 103.7 104.5 102.0 99.5 95.9 97.4 97.3 95.9 100.6 98.9 94.7 95.8 Data obtained from Table 10, p. 44 and Table 34, p. 56 of the study report. na = Not applicableSulfentrazone (PC 129081 ) MRID 48958902

Page 13 of 22 

### E . Transformation of Parent Compound: Transformation kinetics of the parent compound (combined labels) in the total systems are summarized in the following Figure

. Transformation product information summarized in Table 8

.

Using firs t

- order linear regression, the study authors determined a half

- lives for each label of each sediment. In the pond water:silty loam sediment system, the half

- lives were 897 and 559 days for the phenyl label and carbonyl label, respectively (p. 35). In the c anal water:sandy loam sediment system, the half

- lives were 809 and 500 days for the phenyl label and carbonyl label, respectively (p. 35). The reviewer calculated system half

- lives were 679 days for the pond system and 612 days for the canal system.

Transformation Kinetics of SulfentrazoneSulfentrazone (PC 129081 ) MRID 48958902

Page 14 of 22 

### Table 8 . Transformation Products of Sulfentrazone in Total Aquatic System s

System Transformation product(s) Maximum

% AR

Observed Associated

Interval (days) Final % AR

Observed Final Interval

(days)

California pond water:silty clay loam sediment (20oC, sediment pH 6.1) SCA (carbonyl) 1.0 100 1.0

100
HMS (carbonyl) 1.2 100 1.2

California canal water:sandy loam sediment system (20oC, sediment pH 6.0) SCA (carbonyl) 1.3 100 1.3

100
HMS (carbonyl) 1.4 100 1.4

1 Water and sediment pH obtained from Table s 28

- 34 , pp. 5 3

- 56 of the study report.



### Aerobic Aquatic Degradation Pathway. A pathway was not provided by the study author

. Sulfentrazone was relatively stable (DT50 ca. 20

- 22 months) with formation of very minor transformation products and some limited binding to the sediment

.

III. S tudy Deficiencies

, Reviewer's Comments , and Data Needs

1. The study authors did not report posttreatment pH, DO and redox potentials. Although the study protocol states that these would be measured (Appendix 5, p. 138) and a protocol deviation (p. 37) suggests that these were measured at all but the final sampling interval for the pond system, no methodology is provided and no data are r eported. It is therefore uncertain whether aerobic conditions were maintained in the water:sediment systems.Sulfentrazone (PC 129081 ) MRID 48958902

Page 15 of 22 

### 2. The pesticide use histories for the source sites for the sediments and waters were not reported

. The sediments and waters were not analyzed for p esticides to establish that they were not contaminated prior to treatment.

3. Limits of Detection (LOD) and Quantitation (LOQ) for sulfentrazone and its transformation products were not reported.

4. Lengths and conditions of storage of sediments and associated waters prior to shipment to the test facility were not reported. Other than temperature (4oC) and access to air, conditions of storage of sediments and associated waters at the test facility prior to preparation of water:sediment systems for pretreatment acclimation were not reported (pp. 22

- 23). Current OCSPP guidelines specify if storage is necessary, sediment and water should be sieved and stored together, water

- logged (6

- 10 cm water layer), in the dark, at 4 ± 2°C for a maximum of 4 weeks, with free access of air (open containers). It was not reported if the water was sieved.

5. The incubation temperature was 2 0 ± 2  C, which is more variable than specified by guidelines (p. 25 ). The maximum and minimum temperatures were not reported. Data was provided graphically. In addition, graphs were difficult to read.

6. The study author s did not relate the application rate to a field use rate

.

The following are required to potentially upgrade this study from “supplemental” to “acceptable”

status:

1. Confirmation is needed of whether aerobic conditions were maintained in the water:sediment systems. The study authors did not report post

- treatment pH, dissolved oxygen and redox potentials.

2. Control sample analytical results for sulfentrazone residues need to be reported to determine whether background levels of sulfentrazone or degradates ma y have been present in the test system before treatment. The pesticide use histories associated with the source sediment / water source material should be reported.

3. Collection details, including geographic location of the source sites, should be reported

. The study authors reported that the sediments were collected and managed in accordance with ISO

10381

- 6 (p. 23).

4. Limits of Detection (LOD) and Quantitation (LOQ) for sulfentrazone and its transformation products were not reported.

5. Details of the lengt hs and conditions of storage of sediments and associated waters prior to shipment to the test facility should be reported. Other than temperature (4oC) and access to air, conditions of storage of sediments and associated waters at the test facility prior t o preparation of water:sediment systems for pretreatment acclimation were not reported (pp. 22

- 23). Current OCSPP guidelines specify if storage is necessary, sediment and water should be sieved and stored together, water

- logged (6

- 10 cm water layer),

in th e dark, at 4 ± 2°C for a maximum of 4 weeks, with free access of air (open containers). It was not reported if the sediment was sieved.Sulfentrazone (PC 129081 ) MRID 48958902

Page 16 of 22 

### 6. A more detailed accounting of temperature of the incubated soil:sediment mixture during the study is

needed. The incuba by guidelines (p. 25). Daily temperature ranges should be reported numerically (the included graphs were difficult to read).

7. The application rate of the test substance should be related to a field use rate equivalent.



### IV. References

1. U.S. Environmental Protection Agency. 2012. NAFTA Guidance for Evaluating and Calculating Degradation Kinetics in Environmental Media.

2. U.S. Environmental Protection Agency. 2008. Fate, Transport and Transformation Test

- Guidelines, OPPTS 835.4 3 00, Aerobic Aquatic Metabolism. Office of Prevention, Pesticides and Toxic Substances, Washington, DC. EPA 712

- C

- 08

- 01 8

.Sulfentrazone (PC 129081 ) MRID 48958902

Page 17 of 22 DER ATTA CHMENT 1

. Sulfentrazone and Its Environmental Transformation Products. A

Code Name/ Synonym Chemical Name Chemical Structure Study Type MRID Maximum %AR (day) Final %AR (study length)

PARENT

Sulfentrazone IUPAC: 2′,4′

- Dichloro

- 5′

- (4

- difluoromethyl

- 4,5

- dihydro

- 3

- methyl

- 5

- oxo

- 1 H

- 1,2,4

- triazol

1

- yl)methanesulfonanilide

CAS: N

- [2,4

- dichloro

- 5

- [4

- (difluoromethyl)

- 4,5

- dihydro

- 3

- methyl

- 5

- oxo

- 1 H

- 1,2,4

- triazol

1

- yl]phenyl]methanesulfonamide

CAS No.: 122836

- 35

- 5

Formula: C 11 H 10 Cl 2 F 2 N 4 O 3 S

MW: 387.1 g/mol

SMILES: CLc1cc(CL)c(NS(=O)(=O)C)cc 1N2N=C(C)N(C(F)F)C2(=O) 835.4300

Aerobic aquatic

metabolism 48958902 Pond

water/silty clay loam 107.2% (0 d) 99.6% (100 d)

Canal water/sandy

loam 102.1% (0 d) 94.2% (100 d)

MAJOR (>10%) TRANSFORMATION PRODUCTS
No major transformation products were identified.

MINOR (<10%) TRANSFORMATION PRODUCTS

Sulfentrazone 3

- carboxylic acid (SCA) IUPAC: 1

- (2,4

- Dichloro

- 5

- (N

- (methylsulfonyl)amino)

- pheny]

- 4

- difluoromethyl

- 4,5

- dihydro

- 5

-

oxo

- 1 H

- 1,2,4

- triazol

- 3

- carboxylic acid

CAS: N

- [2,4

- dichloro

- 5

- [4

- (difluoromethyl)

- 4,5

- dihydro

- 5

-

oxo

- 1 H

- 1,2,4

- triazol

- 1

- yl]phenyl]methanesulfonamido

3

- carboxylic acid

CAS N o.: 134391

- 01

- 08

Formula: C 11 H 8 Cl 2 F 2 N 4 O 5 S

MW: 417.18 g/mol 835.4300

Aerobic aquatic

metabolism 48958902 Pond

water/silty clay loam 1.0% (100 d) 1.0% (100 d)

Canal water/sandy

loam 1.3% (100 d) 1.3% (100 d)Sulfentrazone (PC 129081 ) MRID 48958902

Page 18 of 22 Code Name/ Synonym Chemical Name Chemical Structure Study Type MRID Maximum %AR (day) Final %AR (study length)

SMILES: CS(=O)(=O)Nc1cc(c(cc1Cl)Cl)n 2c(=O)n(c(n2)C(=O)O)C(F)F

3

- Hydroxymethyl

sulfentrazone (HMS) IUPAC: 1

- (2,4

- Dichloro

- 5

- (N

- (methylsulfonyl)amino)

- pheny]

- 4

- difluoromethyl

- 3

- hydroxy

methyl

- 1 H

- 1,2,4

- triazol

- 5(4H)

-

one

CAS No.: 134390

- 99

- 1

Formula: C 11 H 10 Cl 2 F 2 N 4 O 4 S

MW: 403.19 g/mol

SMILES: CS(=O)(=O)Nc1cc(c(cc1Cl)Cl)n 2c(=O)n(c(n2)CO)C(F)F 835.4300

Aerobic aquatic

metabolism 48958902 Pond

water/silty clay loam 1.2% (100 d) 1.2% (100 d)

Canal water/sandy

loam 1.4% (100 d) 1.4% (100 d)

Carbon dioxide IUPAC: Carbon dioxide

Formula: CO 2 MW: 44 g/mol

SMILES: C(=O)=O 835.4300

Aerobic aquatic

metabolism Pond

water/silty clay loam 0.3% (100 d) 0.3% (100 d)

Canal water/sandy

loam 0.9% (100 d) 0.9% (100 d)

REFERENCE COMPOUNDS NOT IDENTIFIED

3

- Desmethyl sulfentrazone (DMS) IUPAC: 1

- (2,4

- Dichloro

- 5

- (N

- (methylsulfonyl)amino)

- pheny]

- 4

- difluoromethyl

- 1 H

- 1,2,4

- triazol

- 5(4H)

- one

CAS: N

- [2,4

- dichloro

- 5

- [4

- (difluoromethyl)

- 4,5

- dihydro

- 5

-

oxo

- 1,2,4

- triazol

- 1

- yl]phenyl]methanesulfonamide

CAS No.: 134391

- 02

- 09

Formula: C 10 H 8 Cl 2 F 2 N 4 O 3 S

MW: 373.17 g/mol

SMILES: CS(=O)(=O)Nc1cc(c(cc1Cl)Cl)n 835.4300

Aerobic aquatic

metabolism 48958902 NA NASulfentrazone (PC 129081 ) MRID 48958902

Page 19 of 22 Code Name/ Synonym Chemical Name Chemical Structure Study Type MRID Maximum %AR (day) Final %AR (study length)

2c(=O)n(cn2)C(F)F
Methyl triazole IUPAC: 4

- Difluoromethyl

- 5

- methyl

- 2,4

- dihydro[1,2,4]triazole

- 3

- one

Formula: C 4 H 5 F 2 N 3 O

MW: 149.1 g/mol

SMILES: Cc1n[nH]c(=O)n1C(F)F 835.4300

Aerobic aquatic

metabolism 48958902 NA NA

A AR means “applied radioactivity”

. MW means “molecular weight”. NA means “not applicable”

.Sulfentrazone (PC 129081 ) MRID 48958902

Page 20 of 22 

### Attachment 2: Statistics Spreadsheets and GraphsSulfentrazone (PC 129081 ) MRID 48958902

Page 21 of 22 

### Attachment 3: Calculation s

Calculations were performed by the reviewer using R software, and the following equations.

Single First

- Order (SFO) Model

(eq. 1)

where,

C t 

### = concentration at time t (%)

C 0 

### = initial concentration (%) e = Euler’s number (

- )

k = SFO rate constant of decline (d

- 1 

### ) t = time (d)

The SFO equation is solved with R kinetics software by adjusting C 0 

### and k to minimize the objective function (S SFO 

### ) shown in equation 9.

DT 50 

### = natural log (2)/k (eq. 2)

DT 90 

### = ln (10)/k (eq. 3)

Indeterminate Order Rate Equation (IORE) Model

(eq. 4)

where, N = order of decline rate (

- )

k IORE 

### = IORE rate constant of decline (d

- 1 

### )

This equation is solved with R kinetics software by adjusting C0, kIORE, and N to minimize the objective function for IOR E (SIORE) (See equation 9). Half

- lives for the IORE model are calculated using equation 5, which represents a first

- order half

- life that passes through the DT 90 

### of the IORE model. (Traditional DT 50 

### and DT 90 

### values for the IORE model can be calculated using equations 6 and 7.)

(eq. 5)

DT 50 

### = (eq. 6)

DT 90 

### = (eq. 7)Sulfentrazone (PC 129081 ) MRID 48958902

Page 22 of 22 

### Double First

- Order in Parallel (DFOP) Model

(eq. 8)

where, g = the fraction of C 0 

### applied to compartment 1 (

- )

k 1 

### = rate constant for compartment 1 (d

- 1 

### )

k 2 

### = rate constant for compartment 2 (d

- 1 

### )

If C 0 

### x g is set equal to a and C 0 

### (1

- g) is set equal to c , then the equation can be solved with R

kinetics software for a , c , k 1 

### , and k 2 

### by minimizing the objective funct ion (S DFOP 

### ) as described in equation 9.

DT 50 

### and DT 90 

### values can be calculated using equations 2 and 3, with k 1 

### or k 2 

### in place of k.

Objective Function: SFO, IORE, and DFOP are solved by minimizing the objective function (S SFO 

### , S IORE 

### , or S DFOP 

### ).

(eq. 9)

where,

S SFO 

### , S IORE 

### , or S DFOP 

### = objective function of kinetics model fit (% 2 

### ) n = number of data points (

- )

C model,t 

### = modeled value at time corresponding to C d,t 

### (%)

C d,t 

### = experimental concentration at time t (%)

Critical Value to Determi ne Whether SFO is an Adequate Kinetics Model

If S SFO 

### is less than S C 

### , the SFO model is adequate to describe kinetics. If not, the faster of t IORE 

### or the DFOP DT 50 

### for compartment 2 should be used.

(eq. 10)

where,

S
c 

### = the critical value that defines the confidence contours (% 2 

### ) p = number of parameters (3 in this case) α = the confidence level (0.50 in this case) F(α, p, n

- p) = F distribution with α level of confidence and degrees of freedom p and n

- p