Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### UNITED STA

TES ENVIRONMENTA L PROTECTION AGENCY WASHINGTON, D.C. 20460 OFFICE OF PREVENTION, PESTICIDE S

AND TOXIC SUBSTANCES 

### MEMORANDUM Date : 09 /29 /20 08 Subject : Sulfentrazone . Section 3 Registration Request to Add New Uses on: Brassica , Head and Stem, Subgroup 5A; Brassica , Leafy Greens, Subgroup 5B; Melon, Subgroup 9A; Fruiting Vegetable, Group 8 and Okra; Pea, Succulent; Flax; Strawberry ; and Tuberous and Corm Vegetable, Subgroup 1C. Summary of Analy tical Chemistry and Residue Data. PC Code: 129081 DP Barcode: D 349321 Decision No.: 38805 0 Registration No s : 279 - 3220 & 279 - 3189 Petition No.: 7E7308 Regulatory Action: Amended Section 3 Risk Assessment Type: NA Case No.: NA T XR No.: NA CAS No.: 122836 - 35 - 5 MRID No.: see MRID Summary Table 40 CFR: § 180. 498 

### From: William D. Wassell, Chemist

Registration Action Branch 1 (RAB1) Health Effects Division (HED, 7509P) Through: George F. Kramer, Ph.D., Branch Senior Chemist

RAB1/HED (7509P) To: Daniel Rosenblatt , RM 05

Registration Division (RD, 7505P) MRID Summa ry Table MRID No. Study Type Comme nts 47311401 860.1500 broccoli New DER; 47311401.der.doc 47311402 860.1500 mustard greens New DER; 4731140 2 .der.doc 47311403 860.1500 cantaloupe New DER; 473 1140 3 .der.doc 47311404 860.1500 pepper 47311405 860.1500 tomato

860.15 20 tomato New DERs ; 4731140 4 .der.doc (includes MRID 47311405) and 47311405.der.doc 47311406 860.1500 succulent pea New DER; 4731140 6 .der.doc 47311407 860.1500 flax

860.15 20 flax New DERs ; 47311407 .de 1 .doc and 47311407.de2.doc 47311408 860.1500 strawberry New DER; 47311408 .der.doc 

### This document was originally prepared under contract by Dy namac Corporation (2275 Research Boulevard, Suite 300; Rockville, MD 208 50 ; submitted: 05/22/2008 ) . This document has been reviewed by HED and revised to reflect current Office of Pes ticide Programs (OPP) policies.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### Executive Summary Sulfentrazone is an aryl triazolinone herbicide used to control a variety of broadleaf weeds. The mode - of - action for controlling emerging weeds is by protoporphy rinogen oxidase (PPO) inhibition. Sulfentrazone acts by the same mechanism as the diphenyl ether herbicides in which membrane disruption is initiated by the inhib ition of PPO in the chlorophyll biosy nthetic pathway and leads to the subsequent build- up of toxic intermediates. Plants emerging from soils treated with sulfentrazone turn necrotic and die shortly after exposure to light. The Interregional Research Proj ect No. 4 (IR- 4) has submitted a petition propos ing the establishment of permanent tolerances for the combined residues of the herbicide sulfentrazone [N - [ 2,4 - dichloro - 5 - [ 4 - (difluoromethyl) - 4,5 - dihydro - 3 - methyl - 5 - oxo - 1 H - 1,2,4 - triazol - 1 - yl ] phenyl ] methanesul fonamide ] and its metabolites HMS [N - (2,4 - dichloro - 5 - (4 - (difluoromethyl) - 4,5 - dihydro - 3 - hydroxy methyl - 5 - oxo - 1 H

- 1,2,4 - triazol yl )phenyl)methanesulfonamide)] and DMS [( N - 2,4 - dichloro - 5 - [ 4 - (difluoromethyl) - 4,5 - dihydro 5 - oxo - 1 H - 1,2,4 - triazol - 1 - yl )phenyl)methan esulfonamide] in/on : Brassica , head and stem, subgroup 5A * ..................... 0.20 ppm Brassica , leafy greens, subgroup 5B ........................... 0.35 ppm Melon, subgroup 9A ................................ ................... 0.10 ppm Vegetable, fruiting, group 8 ................................ ........ 0.05 ppm Okra ................................ ................................ ............. 0.05 ppm Pea, succulent ................................ .............................. 0.05 ppm Flax ................................ ................................ ............. 0.05 ppm Strawberry ................................ ................................ ... 0.05 ppm Vegetable, tuberous and corm, subgroup 1C * ............ 0.15 ppm * Individual tolerances are established for residues in/on cabbage at 0.20 ppm and potato at 0.15 ppm . 

### A tolerance is currently established under 40 CFR §180.498(a)(1) for the combined residues of sulfentrazone and it s major metabolite, HMS, in/on soy bean seed at 0.05 ppm. In addition, permanent tolerances are established under 40 CFR §180.498(a)(2) for the combined residues of sulfentrazone and its metabolites HMS and DMS in/on several food commodities ; these established tolerances range from 0. 1 5 ppm (various plant commodities) to 0.40 ppm (peanut meal ). Time - limited tolerance s for the combined residues of sulfentrazone and its metabolites HMS and DMS have been established under 40 CFR § 180.4 98 (b) in co nnection with Section 18 Emergency Exemptions ; these include tolerances for residues in/on bean, succulent - seed without pod (lima bean & cowpea) at 0. 1 ppm with a 12/31/0 7 expiration date , flax seed at 0.2 ppm with a 12/31/10 expiration date, and strawberr y at 0.60 ppm with a 12/31/10 expiration date . Finally, tolerances are established under 40 CFR § 180.498(d) for inadvertent and indirect combined residues of sulfentrazone and its metabolites HMS and DMS in/on cereal grain (excluding sweet corn) bran, forage, grain, hay, hulls, stover, and straw at 0.1 - 0.6 ppm as a result of the application of sulfentrazone to growing crops. There are no Mexican, Canadian or Codex maximum residue limits (MRL s) established for sulfentrazone in/on any of the subject crops; therefore, there are no compatibility issues to be reconciled.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### The sulfentrazone end -use products (EPs) relevant for this registration request are Spartan ® 

### Herbicide (EPA Reg. No. 279 - 3189 ; 75% dry- flowable or DF formulation) and Spartan ® 

### 4F Herbicide (EPA Reg. No. 279 - 3220 ; 4 lb/gal flowable - concentrate (FlC) formulation) . IR- 4 requests the amendment of these EP labels to incorporate new uses on head and stem Brassica , leafy greens Brassica , fruiting vegetables including okra, melons, strawberry, succulent peas and beans, and flax . These EPs are proposed for: (i) preplant or preemergence applications on all of the above - listed crops at maximum seasonal rates of 0.1875 - 0.375 lb ai/A using ground or aerial equip ment; and (ii) postemergence applications on fruiting vegetables at a maximum seasonal rate of 0.375 lb ai/A. No pre - harvest intervals (PHI s) were proposed for these crops. The nature of the residue in soy bean s as well as rotational crops is adequately understood. The HED Metabolism Committee has determined that the parent compound, sulfentrazone, and the metabolite HMS are the residues of concern in soy beans, and that sulfentrazone and the metabolites HMS and DMS are the residues o f concern in rotational crops (D226434, 6/14/96, G. Kramer). In addition, HED concluded that the results of the rotational crop metabolism studies may be translated to support preemergence uses on all ty pes of crops (D220548, 3/13/96, G. Kramer). However , as the proposed use pattern on f ruiting v egetables includes postemergence application s , metabolism data are not available to support this specific use pattern. HED is, therefore, recommending that all proposed uses should be limited to preemergence appl ication only unless the petitioner is willing to submit new metabolism studies on fruiting vegetables reflecting postemergence application . However , as the enforcement method for plant commodities determines free and conjugated forms of the analy tes, the tolerance expression should be revised to indicate the residues of concern are the combined residues of free and conjugated sulfentrazone, and its metabolites HMS and DMS. The nature of the residue in livestock is adequately understood based on acceptable ruminant and poultry metabolism studies. Sulfentrazone per se and its metabolites HMS and DMS were identified as the residues of concern in meat, milk, poultry, and eggs. Based on established and proposed sulfentrazone tolerances and the results of live stock metabolism studies, conventional feeding studies and tolerances for livestock commodities are not required for the purpose of this petition only . There is an adequate residue analy tical method for the purpose s of tolerance enforcement. A gas chromatography (GC) method for the determination of sulfentrazone and its metabolites DMS and HMS was submitted with a petition for a sulfentrazone tolerance on soy beans (PP# 4F04 4 07). A petition method validation (PMV) was successfully completed by the Agency ’ s Analy tical Chemistry Laboratory (ACL). The limit of quantitation (LOQ) and limit of detection (LOD) were determined to be 0.05 ppm and 0.005 - 0.025 ppm, respectively . The method has been forwarded to the Food and Drug Administration (FDA) for inclusion in the Pesticide Analy tical Methods Vol. II (PAM II). The data requirements for multiresidue methods (MRMs) are fulfilled. The FDA MRMs are not suitable as enforcement methods since sulfentrazone residues of concern were not successfully recovered by the FDA MRMs . Samples of raw agricultural and processed commodities were analy zed for residues of sulfentrazone and its metabolites DMS and HMS using either a GC /XSD halogen - specific detector) method or a liquid chromatograph equipped with tandem mass spectrometersSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### (LC/MS/MS) method . The validated LOQ was 0.05 ppm for each analy te. The se methods are adequate for data collection based on acceptable method validation and concurrent recovery data. Pending submission of a revised Section F as specified in Tabl e 15 , adequate crop field trial data have been submitted for: broccoli, one of the representative commodities of head and stem Brassica (subgroup 5A); provided the proposed use directions (Section B) are modified, mustard greens, the sole representative c ommodity of Brassica leafy greens (subgroup 5B); peas (succulent and edible -podded); bell and non -bell pepper s and tomato es, the representative commodities of fruiting vegetables (group 8) ; cantaloupe , the sole representative commodity of melon subgroup (subgroup 9A) ; strawberries; and flax. The submitted data showed that the combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on mature commodities listed above following application(s) of a representative formulation of sulfentrazone according to the proposed crop use pattern. It is, however, noted that higher residues were observed in/on mustard green samples treated at <1.0x . The field trial data are supported by adequate storage stability data, and no corrections need to be applied to th e observed residue levels . A revised Section B should be submitted to remove the proposed postemergence use on fruiting vegetables. The previously reviewed data for potato, the representative commodity of tuberous and corm vegetables (subgroup 1C) may be used to support the requested use pattern for the subgroup. These data were submitted as part of PP # 2 E6405 (D 287102 , 1/10/03, G. Kramer) and showed that the maximum combined residues of sulfentrazone and its metabolites HMS and DMS were 0.077 ppm in/on potato tubers after a preemergence treatment at 1x. The previously reviewed data for cabbage, another representative commodity of head and stem Brassica (subgroup 5A) may be used to support the requested use pattern for the subgroup. These data were submitted in conjunction with PP#1E6311 (D276111, 12/9/02, G. Kramer) and indicate that the combined residues of sulfentrazone, HMS, and SCA (quantitated as DMS) were <0.15 - 0.18 ppm and <0.15 - 0.17 ppm in/on cabbage heads with and without wrapper leaves, respec tively, following application at 1x . The submitted data for the fruiting vegetables may used to support the proposed use on okra. The submitted flax and tomato processing studies are unacceptable since the studies did not conclusively demonstrate that sulfentrazone residues of concern will not concentrate in processed fractions as a result of the proposed use. Quantifiable residues were not detected in the RACs used for processing, and the field trials were conducted at only 1x (flax) or 2x (tomatoes) rates. Since phy totoxicity does not appear to be an issue, the processing studies need to be repeated using an exaggerated application rate (equal to the maximum theoretical concentration factor or 5x, whichever is less). Rotational crop studies for corn, rice, sorghum, and wheat were previously submitted in conjunction with the soy

bean petition (PP#4F 0 4407). Permanent tolerances have been established for indirect or inadvertent residues of sulfentrazone and its metabolites, HMS and DMS, in cereal grains ( excluding sweet corn), bran, forage, grain, hay, hulls, stover, and straw. As the 1x use rate in soy

beans (0.375 lb ai/A) is ≥ the 1x use rate of the proposed new uses, the established tolerances for indirect or inadvertent residues of sulfentrazone and its metabolites, HMS and DMS are adequate to support the subject petition. The proposed rotational crop restrictions are adequate and consistent with previous sulfentrazone petitions.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### Analy tical standards for sulfentrazone and its metabolites DMS and HMS are currently available at the EPA National Pesticide Standards Repository . However, the standard s for sulfentrazone and its metabolite DMS will expire 10/1/2012 and 5/1/2012, respectively, and the standard for HMS has expired 4/1/2008 . Regulatory Recommendations and Residue Chemistry De ficiencies HED has examined the residue chemistry database for sulfentrazone. There are no residue chemistry issues that would preclude granting a conditional registration for the requested uses p ending submissions of

: a revised Section B (see requirements under Directions for Use) ; reference standard for the metabolite HMS (see requirements under Submittal of Analy tical Reference Standards ); and a revised Section F (see Table 15). Full and unconditional registration will be grante d following submission of adequate flax and tomato processing studies. The propose d uses and the submitted data support the establishment of the following tolerances for the combined residues of free and conjugated sulfentrazone and its metabolites HMS and DMS in/on : Brassica , head and stem, subgroup 5A ....................... 0.20 ppm

Brassica , leafy greens, subgroup 5B ........................... 0. 40 ppm Melon, subgroup 9A ................................ ................... 0.1 5 ppm Vegetable, fruiting, group 8 ................................ ........ 0. 1 5 ppm Okra ................................ ................................ ............. 0. 1 5 ppm Pea, succulent ................................ .............................. 0. 1 5 ppm Flax ................................ ................................ ............. 0. 1 5 ppm Strawberry ................................ ................................ ... 0. 1 5 ppm Vegetable, tu

berous and corm, subgroup 1C .............. 0.15 ppm A human - health risk assessment is forthcoming. Note to RD: As the enforcement method for plant commodities determines free and conjugated forms of the analy

tes, the tolerance expression should be revised to indicate tolerances are established for combined r esidues of free and conjugated forms of sulfentrazone, and its metabolites HMS and DMS. 860.1200 Directions for Use A revised Section B is required. The proposed label for Spartan ® 

### 4F Herbicide (EPA Reg. No. 279 - 3220 ), a 4 lb/gal FlC formulation, should be modified to correct the application rates listed as “ dry ounces Spartan ® 

### Herbicide per acre ” to “fluid ounces Spartan ® 

### Herbicide per acre . ” Also, as metabolism data are not available to support postemergence a pplications on f

ruiting v egetables , these proposed uses should be limited to preemergence application only . Additionally, the proposed labels should be revised to specify a maximum single and seasonal application rate of 0.020 lb ai/A for Spartan ® 

### to Brassica leafy greens subgroup 5B as this rate is supported by the submitted crop field trial data for mustard greens.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### 860.1 520 Processed Food and Feed New flax and tomato processing studies should be submitted. Since phy totoxicity does not appear to be an issue, the requested processing studies should use an exaggerated application rate (equal to the maximum theoretical concentration factor or 5x, whichever is less). 860.1650 Submittal of Analy tical Reference Standards As the reference standard for the metabolite HMS has expired 4/1/2008 , the petitioner must submit a new standard . If new standards are being submitted, they should be sent to the Analy tical Chemistry Lab, which is located at Fort Meade, to the attention of either Theresa Cole or Thuy Nygen at the following address: USEPA National Pesticide Standards Repository /Analy tical Chemistry Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755 - 5350 860.1550 Proposed Tolerances A summary of recommended tolerances are presented in Table 1 5 . The petitioner is required to submit a revised Section F to reflect appropriate tolerance levels. Background The chemical structure and nomenclature of sulfentrazone are presented in Table 1 , and the physicochemical properties of the technical grade of sulfentrazone are presented in Table 2 .Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 7 of 34 Table 1. Sulfentrazone N om enclature . Chemical structure

Cl Cl

N H S O 2 CH 3

N N N O CH 3

CH F 2

Common name Sulfentrazone Company experimental name F6285; FMC 97285 IUPAC name 2',4' - dichloro - 5' - (4 - difluoromethyl - 4,5 - dihydro - 3 - methyl - 5 - oxo - 1 H - 1,2,4 - triazol 1 - yl)methanesulfonanilide CAS name 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 registry number 122836 - 35 - 5 End -use product (EP) 4 lb/gal FlC formulation (Spartan® 4F Herbicide; EPA Reg. No. 279 - 3220) and 75% DF formulation (Spartan® Herbicide; EPA Reg. No. 279 - 3189 ) Chemical structure of DMS metabolite

Cl Cl

N H S O 2 CH 3

N N N O C H F 2

Common name 3 - desmethyl sulfentrazone; DMS Chemical name N - (2,4 - dichloro - 5 - (4 - (difluoromethyl) - 4,5 - dihydro - 5 - oxo - 1 H - 1,2,4 - triazol - 1 - yl)phenyl)methanesulfonamide Chemical structure of HMS metabolite

Cl Cl

N H S O 2 C H 3

N N N O C HF 2

O H

Common name 3 - hydroxymethyl sulfentrazone; HMS Chemical name N - (2,4 - dichloro - 5 - (4 - (difluoromethyl) - 4,5 - dihydro - 3 - hydroxymethyl - 5 - oxo - 1 H1,2,4 - triazol - 1 - yl)phenyl)methanesulfonamideSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 8 of 34 Table 2. Physicochemical Properties of Technical Grade Sulfentrazone . Parameter Value Reference Melting range 120 - 122 oC pH 4.78 at 23 oC Density 0.53 g/cm3 Water solubility 4.0 x 10 2 μg/g Solvent solubility 18.6% w /w in acetonitrile Vapor pressure 8 x 10 - 10 mm Hg Dissociation constant, pKa 6.56 Octanol/water partition coefficient, Log(KOW) 1.49 at pH 5 DP# 288712, 3/ 6 /03, G. Kramer , G. Reddy, and L. Liu

UV/visible absorption spectrum Not available 

### 860.1200 Directions for Use A list of the sulfentrazone end -use products relevant to this registration request is presented in Table 3. The proposed crop use directions are summarized in Table 4 A . In formation regarding rotational crop restrictions is listed in Table 4B. T able 3 . Summary of Proposed End - Use Products . Trade Name Reg. No. ai (% of formulation) Formulation

Type Target Crops Target Pests Label Date Spartan ® 4F Herbicide 279 - 3220 39.6 (4 lb/gal) FlC Specimen label code: Spartan4F

_ 3

_ 12 - 17 - 07 Spartan ® Herbicide 279 - 3189 75 DF Row Crops: corn (field, seed, and pop); peanut; potato; soybean; sugarcane; sunflower; tobacco . Vegetable Crops: asparagus; Brassica , head and stem; Brassica , leafy greens; cabbage (transplant only); dry shelled beans and peas; fruiting vegetables (except cucurbits) and okra; horseradish; melons; strawberry; succulent peas and beans; Oil Crops: flax; mint . B roadleaf, grass,

and sedge weeds . Specimen label

code: Spartan _3_12 - 17 - 07Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 9 of 34 Table 4 A . Summary of Proposed Directions for Use of Sulfentrazone . Applic. Timing, Ty pe, and Equip. Formulation

[EPA Reg. No.] Applic. Rate ,

lb ai/A [Soil Type] Max. No. Applic.

per Season Max. Seasonal

Applic. Rate (lb ai/A) PHI

(days) Brassica , Head and Stem [broccoli, Chinese broccoli, Brussels sprouts, Chinese (napa) cabbage, Chinese mustard, cauliflower, cavalo broccoli, kohlrabi] 4 lb/gal FlC [279 - 3220] 75% DF [279 - 3189] 0.070 - 0.281

[coarse] 0. 094 - 0.375 [medium and fine] Not specified

(NS) 0.375 NS Early preplant, preemergence, preplant incorporated Use Directions and Limitations Do not incorporate to depths greater than 2 inches. Brassica , L eafy Greens [ b roccoli raab, Chinese (bok choy) cabbage, collards, kale, mizuna , mustard greens, mustard spinach, rape greens] 4 lb/gal FlC [279 - 3220] 75% DF [279 - 3189] 0.070 - 0.281

[coarse] 0.094 - 0.375 [medium and fine] NS 0.375 NS Early preplant, preemergence, preplant incorporated Use Directions and Limitations : Do not incorporate to depths greater than 2 inches. Fruiting Vegetables (except curcurbits) [eggplant, groundcherry (Physalis spp), pepino, pepper (includes bell pepper, chili pepper, cooking pepper, pimento, sweet pepper), tomatillo, tomato] and o kra 4 lb/gal FlC [279 - 3220] 75% DF [279 - 3189] 0.070 - 0.281

[coarse] 0.094 - 0.375 [medium and fine] NS 0.375 NS Preplant banded or postemergence with shielded/hooded sprayer Use Directions and Limitations : None . Succulent Peas and Beans [bean (Phaseolus; includes green lima bean and succulent broad bean), bean ( Vigna ; includes blackeyed pea, cowpea, southern pea), pea (Pisum ; includes English pea, garden pea, green pea); pigeon pea 4 lb/gal FlC [279 - 3220] 75% DF [279 - 3189] 0.070 - 0.1875

[coarse] 0.094 - 0.1875 [medium] 0 .117 - 0.1875 [fine] NS 0.1875 NS Preemergence Use Directions and Limitations : Do not incorporate. Flax 4 lb/gal FlC [279 - 3220] 75% DF [279 - 3189] 0.070 - 0.281

[coarse] 0.094 - 0.375 [medium and fine] NS 0.375 NS Preemergence Use Directio ns and Limitations : Do not apply directly on crop after the crop emergence or if

the seedling sprouts are close to the soil surface.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 10 of 34 Melon [ c itron melon, muskmelon, watermelon] 4 lb/gal FlC [279 - 3220] 75% DF [279 - 3189] 0.093 - 0.1875

[coarse] 0.093 - 0.2125 [medium] 0.117 - 0.25 [fine] NS 0.25 NS Preemergence Use Directions and Limitations : Do not apply directly on crop after the crop emergence or if

the seedling sprouts are close to the soil surface. Straw berry 4 lb/gal FlC [279 - 3220 ] 75% DF [279 - 3189] 0.070 - 0.281

[coarse] 0.094 - 0.375 [medium and fine] NS 0.375 NS Preemergence Use Directions and Limitations: Do not apply directly on crop after the crop emergence or if

the seedling sprouts are close to the soil surface. 

### The following re strictions apply to all proposed crops: Application rates are dependent on soil texture, percent organic matter (%OM), and pH. Use on soils classified as sand which have <1% OM is prohibited. Applications are to be made in a minimum of 10 gallons per acre (GPA) using ground equipment or a minimum of 5 GPA using aerial equipment.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 11 of 34 Table 4B. Plantback Intervals for Use of Sulfentrazone . Rotational Crop 1 Plantback Interval (months) Alfalfa 12 Barley 4 Cabbage Anytime Canola 24 Cereal Grains (Buck

wheat, Oats, Pearl Millet, Proso Millet, Teosinte, Wild Rice) 12 Corn, Field 10 Corn, Pop 18 Corn, Sweet 18 Cotton 18 Dry Shell Peas and Beans Anytime Horseradish Anytime Limas Anytime Mint Anytime Peanuts Anytime Potatoes Anytime Rice 10 Rye 4 Sorghum 10 2 Soybean Anytime Sugar Beets 36 Sugarcane Anytime Sunflowers Anytime Sweet Potatoes 12 Triticale 4 Tobacco Anytime Turf Anytime Wheat 4 1 For all other crops not listed, the rotation interval is a minimum of 12 months . 2 Sorghum

– 18 - mo nth rotation for rates above 8.0 oz/A . 

### Conclusions . The use directions are adequate to allow HED an assessment of whether the submitted residue data reflect the maximum residues likely to occur . However, the label for Spartan ® 

### 4F Herbicide (EPA Re g. No. 279 - 3220 ), a 4 lb/gal FlC (liquid) formulation, should be modified to correct the application rates listed as “ dry ounces Spartan ® 

### Herbicide per acre ” to “fluid ounces Spartan® Herbicide per acre ” . Also, as metabolism data are not available to support postemergence applications on f ruiting v egetables (except curcurbits) , these proposed uses should be limited to preemergence application only . Additionally, the proposed labels should be revised to specify a maximum single and seasonal application rate of 0.020 lb ai/A to Brassica leafy greens, subgroup 5B , as this rate is supported by the submitted crop field trial data for mustard greens. A revised Section B is required. 860.1300 Nature of the Residue – Plants and Livestock DP# 226434, 6/14/96, G . Kramer (HED Metabolism Committee Meeting of 5/20/96) DP# 220548, 3/13/96, G. Kramer 

### Data concerning the metabolism of sulfentrazone in soy beans and confined rotational crops were submitted in conjunction with the soy bean petition (PP#4F 0 4407). Sulfentrazone is metabolized via four different pathways: (1) Oxidation of the 3 - methyl group to form 3 - hydroxy methylSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### sulfentrazone or HMS , followed by further oxidation to form sulfentrazone carboxylic acid which is decarboxylated to 3 - desm ethyl sulfentrazone or DMS . (2) Hydrolysis of the trifluoromethyl group to form desdifluoromethyl sulfentrazone which is oxidized and decarboxylated to form desdifluoromethyl desmethyl sulfentrazone. (3) Hydrolysis of the sulfonamide group to form desmethylsulfonyl sulfentrazone. (4) Scission of the phenyl and triazole rings to produce methyl triazole. The corresponding phenyl metabolites are believed to remain bound. The HED Metabolism Committee has determined that the parent compound, sulfentrazone, and the metabolite HMS are the residues of concern in soy beans, and that sulfentrazone and the metabolites HMS and DMS are the residues of concern in rotational crops (D226434, 6/14/96, G. Kramer). In addition, HED concluded that the results of the rotati onal crop metabolism studies may be translated to support preemergent uses on all ty pes of crops (D220548, 3/13/96, G. Kramer). For the proposed uses of sulfentrazone , limited to preemergence application, the nature of the residue in crops is understood . The residues of concern are sulfentrazone and its metabolites HMS and DMS. However, as the enforcement method for plant commodities determines free and conjugated forms of the analy tes, the tolerance expression should be revised to indicate the residue s of concern are the combined residues of free and conjugated sulfentrazone, and its metabolites HMS and DMS . Additionally, a s the proposed directions for use on fruiting vegetables include postemergence applications, HED concludes metabolism data are not available to support the postemergence applications. Adequate ruminant and poultry metabolism studies were submitted in conjunction with the soy bean petition (PP#4F 0 4407). The metabolism of sulfentrazone in livestock differs from that in plants as metab olism proceeds only by oxidation of the 3 - methyl group to form 3 - hydroxy methyl sulfentrazone (HMS) , followed by further oxidation to form sulfentrazone carboxylic acid which is decarboxylated to 3 - desmethyl sulfentrazone (DMS) . Sulfentrazone per se and it s metabolites HMS and DMS were identified as the residues of concern in meat, milk, poultry and eggs. 860.1340 Residue Analytical Methods Letter dated 9/18/98 from G. Kramer to M. Clower (FDA) D 2 33520 , 3/25/97 , G. Kramer 

### Enforcement method A GC analy

ti cal method for the determination of sulfentrazone, DMS, and HMS residues (free and conjugated) in/on various matrices was submitted with a petition for a sulfentrazone tolerance on soy

beans (PP# 4F04 4 07). A PMV was successfully completed by the Agency ’s A CL . The LOQ and LOD were determined to be 0.05 ppm and 0.005 - 0.025 ppm, respectively . HED concluded that the method is suitable for enforcement purposes (D 233520, G. Kramer, 3/25/97). The method was forwarded to FDA for inclusion in PAM II (Letter, G. K ramer, 9/18/98). This method is suitable for enforcement of the tolerances associated with this petition.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### Data - collection methods Samples of raw agricultural commodities (RACS) and processed commodities were analy zed for residues of sulfentrazone and its metabolites DMS and HMS using the FMC method entitled, “Analy tical Methodology for the Determination of Sulfentrazone, 3 - Desmethyl Sulfentrazone, and 3 - Hydroxy

methyl Sulfentrazone in/on Various Matrices, Study Number 162MVL 96R1” with minor modification s. Residues in/on broccoli and mustard greens were determined using GC /XSD , while residues in/on cantaloupe, fruiting vegetables (pepper and tomato), peas, flax, and strawberry were determined using LC/MS/MS . Briefly, homogenized samples were refluxed with acetone:0.25N HCl (30:10, v:v) for 1 hour followed by filtration and concentration, then refluxed a second time with 1N HCI for 2 hours to free all conjugated analy

tes of concern and to completely convert sulfentrazone 3 - carboxylic acid (SCA) to DMS . The method quanti fies residues of SCA as DMS and calculate s SCA residues by a molecular weight - conversion factor (1.12). SCA is a metabolism intermediate in formation of DMS. The extract was filtered, cleaned-up on a C8 solid -phase extraction (SPE) cartri dge and eluted with acetonitrile. The eluate was dried under a gentle stream of nitrogen and additionally clean ed up on a s ilicon (Si) SPE ; eluted twice with ethyl acetate:hexane (60:40, v:v). The eluate s were combined, concentrated , and reconstituted with acetonitrile. For samples of broccoli and mustard greens, an aliquot was analy zed for sulfentrazone and DMS by GC /XSD . A second aliquot was derivatized with B STFA ( N,O -bis[trimenthylsilyl]trifluoroacetamide) and analy zed for HMS by GC/XSD. For sample s of cantaloupe, fruiting vegetables (pepper and tomato), peas, flax, and strawberry and the processed commodities of flax and tomato , the eluate was concentrated to near dry

ness and brought to volume with 25% acetonitrile in water for analysis by LC /MS/MS . For tomato samples, the SPE cleanup step s w ere eliminated; after filtration, the aqueous solution was brought to volume with water and analy zed by LC /MS/MS . The data- collection methods described above are adequate based on acceptable method validation and concurrent recovery data. 860.1360 Multiresidue Methods Residue Chemistry Memo , 2 /7 /95 , G. Kramer 

### MRM data for sulfentrazone and HMS were previously submitted and forwarded to FDA (Memo, 2/7/95, G. Kramer). Neither compound was recovered by any of the protocols. The FDA PESTDATA database dated 10/99 (PAM Vol. I , Appendix II) indicates that DMS is not recovered using MRM Sections 303 (Mills, Onley, and Gaither; Protocol E, nonfatty ) and 304 (Mills, fatty food). No information for recovery of DMS us ing Section 302 (Luke Method; Protocol D) is available. 860.1380 Storage Stability IR- 4 conducted concurrent storage stability studies with the broccoli, cantaloupe, flax, mustard greens, pea (succulent shelled and edible -podded), pepper, strawberry, and tomato field trials, and the flax and tomato processing studies.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 14 of 34 

### The results indicate that residues of sulfentrazone, DMS, and HMS are reasonably stable under frozen storage conditions in/on broccoli for 427 days , cantaloupe for 352 days , flax seed for 484 days , mustard greens for 391 days , pea (succulent shelled and edible -podded) for 757 days, pepper for 596 days, strawberry for 389 days, tomato and tomato paste for 552 days, flax meal for 500 days , and flax oil for 494 days. The storage duration s and conditions of samples from the crop field trials submitted to support this petition are presented in Table 5 .

Table 5 . Summary of Storage Conditions and Duration s of Samples from

Crop Field Trial and Processing Studies. Matrix Storage Tem perature (° C) Actual Storage

Duration Interval of Demonstrated Storage Stability Broccoli - 38 to - 3 Treated samples: 234 - 403 days (7.7 - 13.3 months) Control samples: 236 - 446 days (7.7 - 14.7 months) Residues of sulfentrazone, DMS, and HMS are

stable in frozen storage in/on broccoli for up to 427 days. Mustard greens - 38 to - 3 Treated samples: 104 - 351 days (3.4 - 11.5 months) Control samples: 99 - 439 days (3.3 - 14.4 months) Residues of sulfentrazone, DMS, and HMS are

stable in/on mustard greens during frozen storage f or up to 391 days . Pea, succulent - 38 to - 1 385 - 742 days (12.7 - 24.4 months) Residues of sulfentrazone, DMS, and HMS are

stable in/on peas stored frozen for up to 757 days . Pepper - 40 to - 2 Treated: 450 - 584 days (14.8 - 19.2 months) Control: 450 - 610 days (14.8 - 20.0 months) Residues of sulfentrazone, DMS, and HMS are

stable in frozen storage in/on peppers for up to 596 days .

Tomato ~ - 18 483 - 573 days (15.9 - 18.8 months) Residues of sulfentrazone, DMS, and HMS are

stable in frozen storage in/on tomatoes for up to 552 days . Tomato RAC 506 days (16.6 months) Tomato puree 513 - 519 days (16.9 - 17.1 months) Tomato paste - 12 (processing facility)

- 18 (analytical laboratory) 500 - 506 days

(16.4 - 16.6 months) Residues of sulfentrazone, DMS, and HMS are

stable in frozen storage in/on tomatoes and tomato paste for up to 552 days. Cantaloupe - 38 to - 6 278 - 364 days (9.1 - 12.0 months) Residues of sulfentrazone, DMS, and HMS are

stable in frozen storage in/on cantaloupe for up to 352 days. Strawberry - 38 to - 1 Tre ated samples: 116 - 394 days (3.8 - 13.0 months) Control samples: 116 - 434 days (3.8 - 14.3 months) Residues of sulfentrazone, DMS, and HMS are

stable in frozen storage in/on strawberries for up to 389 days .Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 15 of 34 Flax, seed - 38 to 0.7 354 - 382 days (11.6 - 12.6 months) Residues of sulfentrazone, DMS, and HMS are

stable in/on flax seed during frozen storage for up to 484 days . Flax, seed Treated: 407 days (13.4 months) Control: 406 - 410 days ( 13.4 - 13.5 months) Flax, meal Treated: 468 days (15.4 months) Control: 460 - 623 days (15.1 - 20 .5 months) Flax, oil - 29 to - 14 (p rocessing facility)

- 38 to 0.7 ( analytical laboratory)

Treated: 443 days (14.6 months) Control: 434 - 624 days (14.3 - 20.5 months) Residues of sulfentrazone, DMS, and HMS are

stable in frozen storage for up to 484 days in/on flax seed, 500 days in/on flax meal, and 494 days in/on flax oil.



### Conclusions . The available storage stability data for sulfentrazone are adequate to support the storage conditions and durations of samples of broccoli, cantaloupe, flax, mustard greens, pea (succulent shelled and edible -podded), pepper, strawberry, and tomato from the submitted crop field trials and the flax and tomato processing studies. There are no storage stability issues and no corrections for storage stability need be applied to the field trial and processing studies. 860.1480 Meat, Milk, Poultry, and Eggs PP#s 2F6391, 2E6498, 2E6405, & 2E6500; D 287102, 1/10/03, G. Kramer 

### HED previously determined that, based on the established sulfentrazone tol erances for soy bean and cereal grain commodities and the results of the livestock metabolism studies, conventional feeding studies are not required. This conclusion was reevaluated in conjunction with PP#s 2F6391 and 2E6405 ( 

### D287102, 1/10/03, G. Kramer) b ased on revised dietary burdens resulting from a diet comprised of corn and potato commodities for beef and dairy cattle and corn and rice commodities for poultry. Since a dietary exposure of 10x would not result in quantifiable residues, HED concluded th at conventional ruminant and poultry feeding studies were still not required. In the current petition, the only livestock feedstuff is flax meal. Flax meal is a feed commodity for cattle and swine (10% of diet) and poultry (30% of diet), but would contribute a minor percentage to livestock diets compared to soy beans and cereal grains. Residues of sulfentrazone and its metabolites in/on flax will not result in a higher dietary burden, and tolerances for residues in/on meat, milk, poultry, and egg are not required to support preemergence uses on flax .Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### 860.1500 Crop Field Trials Vegetable, tuberous and corm, subgroup 1C P P#s 2F6391, 2E6498, 2E6405, & 2E6500; D287102, 1/10/03, G. Kramer 

### No new tuberous and corm vegetable field trial data were submitted. An individual tolerance has been established for the combined residues of sulfentrazone and its metabolites HMS and DMS in/on potato at 0.15 ppm [40 CFR §180.498(a)(2)] . Since potato is the representative commodity for the tuberous and corm vegetable, su bgroup 1C, IR- 4 is proposing to convert the individual tolerance for potato to a crop subgroup 1C tolerance at the same level. The available potato field trial data (MRID 45582201) were reviewed in conjunction with PP#2E6405. Fourteen potato field trials were conducted in WA (3 trials), ID (2 trials), ME, FL, NC, OH, CO, ND, NJ, NY, and CA at seasonal application rates of 0.375 lb ai/A (1x the maximum proposed seasonal rate) with PHI s of 68 - 158 days. The maximum combined residues of sulfentrazone and its metabolites HMS and DMS were 0.077 ppm in/on treated potato tubers. Conclusions . The previously submitted residue data for potato are adequate to support the proposed crop subgroup tolerance of 0.15 ppm for tuberous and corm vegetables, subgroup 1C. Brassica , head and stem, subgroup 5A Broccoli 47311401.der.doc 

### IR- 4 has submitted field trial data for sulfentrazone on broccoli, a representative commodity of the Brassica head and stem subgroup 5A. Six field trials were conducted on broccoli in the United States in Zones 1 (NY; 1 trial), 6 (TX; 1 trial), 10 (CA and NM; 3 trials), and 12 (OR; 1 trial) during the 2001 growing season. Each trial site consisted of one untreated plot and one treated plot. A 4 lb/gal FlC formulation of sulfentrazone was app lied as a single broadcast application to soil 72 hours prior to transplanting broccoli or to direct seeded broccoli at the 2 - 4 leaf growth stage, at a rate of 0.34 - 0.38 lb ai/A (~0.9 - 1.0x the maximum proposed seasonal rate). The applications were made in 19 - 35 GPA spray volumes, without an adjuvant. Mature broccoli was harvested at 45 to 73 - day PHI s . Residues of sulfentrazone, DMS, and HMS were each below the LOQ (<0.05 ppm) in/on all samples of broccoli harvested 45 - 73 days following one broadcast appl ication either to soil 72 hours prior to transplanting or to direct seeded broccoli at the 2 - to 4 - leaf growth stage at a rate of 0.34 - 0.38 lb ai/A ; see Table 6 . Total sulfentrazone residues were all <0.15 ppm in/on all treated samples of broccoli.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 17 of 34 T able 6 . Summary of Residue Da ta from Broccoli Field Trials with Sulfentrazone . Residue Levels (ppm) Commodity Total Applic.

Rate (lb ai/A) PHI

(days) n Min. Max. HAFT 1 Median Mean Std. Dev. Proposed Use Pattern: Preplant/preemergence application at a maximum rate of 0.375 lb ai/A Sulfentrazone Broccoli 0.34 - 0.38 45 - 73 12 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- DMS Broccoli 0.34 - 0.38 45 - 73 12 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- HMS Broccoli 0.34 - 0.38 45 - 73 12 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- Total Broccol i 0.34 - 0.38 45 - 73 12 <0.15 <0.15 < 0.15 < 0.15 < 0.15 -- 1 HAFT = h ighest - average f ield trial. For calculation of the total residues , HAFT, median, and mean , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Varying degrees of phy

totoxicity were reported at both CA trial sites and at the NY and TX trial sites. The petitioner indicated that treated broccoli plants were stunted with burned, curled leaves. Although phy

totoxicity was attributed to the test substance application, these isolated instances of phy

totoxicity did not have an adverse impact on the residue trials. Cabbage PP#1E6311, DP# 276111, 12/9/02, G. Kramer 

### A tolerance of 0.20 ppm has been established [40 CFR §180.498(a)(2)] for the combined residues of sulfentrazone and its metabolites HMS and DMS in/on cabbage based on residue data reviewed in PP#1E6311. These data indicate that the combined residues of sulfentrazone, HMS, and SCA (quanti fied as DMS) were <0.15 - 0.18 ppm and <0.15 - 0.17 ppm in/on cabbage heads with and without wrapper leaves, respectively, harv e sted 68 - 104 days following a single ground broadcast application of the 75% DF formulation at 0.375 lb ai/A (1x rate) made 1 - 3 days prior to transplanting or at the 2 - to 4 - leaf growth stage (33 days after planting) to direct seeded cabbage. The petition review concluded that two additional cabbage field trials should be conducted in Regions 1 and 8 as a condition for full registration. Conclusions : The submitted residue data for broccoli along with the previously reviewed data for cabbage are adequate to support the proposed crop subgroup tolerance of 0. 20 ppm for Brassica head and stem , subgroup 5A . Following application of a representative formulation of sulfentrazone at 1x, the combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on broccoli, <0.15 - 0.18 ppm in/on cabbage heads with wrapper leaves , and <0.15 - 0.17 ppm in/on cabbage heads without wrapper leaves . As a condition for full registration, HED previously required two additional cabbage field trials to be conducted in Regions 1 and 8. These trials are no longer needed since an adequate number of broccoli and cabbage field trials are available to satisfy geographic representation for head and stem Brassica , subgroup 5A. Brassica , leafy greens, subgroup 5B Mustard Greens 4 7311402.der.docSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 18 of 34 

### IR- 4 has submitted field trial data for sulfentrazone on mustard greens, the representative commodity of the Brassica leafy greens subgroup 5B. Seven field trials were cond ucted on mustard greens in the United States in Zones 2 (GA and NJ; 2 trials), 3 (FL ; 1 trial), 4 (TN; 1 trial), 5 (OH; 1 trial), 6 (TX; 1 trial), and 10 (CA; 1 trial) during the 2001 - 2002 growing seasons. Each trial consisted of one untreated plot and tw o treated plots, except for one trial (TN) which contained three treated plots. Each treated plot received a single preemergence broadcast soil application of a 4 lb/gal FlC formulation of sulfentrazone at target rate s of ~0.10 lb ai/A (~0.3x; Treatment P lot 2), ~0.20 lb ai/A (~0.5x; Treatment Plot 3) or ~0.40 lb ai/A (~1.1x; Treatment Plot 4). All applications were made in 20 - 40 GPA spray volumes, without an adjuvant. Mature samples were collected 40 - 66 days after treatment. The results of the field trials indicate that residues of sulfentrazone were all below the LOQ (<0.05 ppm) in/on all samples of mustard greens harvested 40 - 66 days following a preemergence broadcast soil application of a 4 lb/gal FlC formulation of sulfentrazone at a rate of ~0.10 lb ai/A (Treatment Plot 2), ~0.20 lb ai/A (Treatment Plot 3) or ~0.40 lb ai/A (Treatment Plot 4); see Table 7. Maximum residues of DMS were 0.098 ppm, 0.136 ppm, and <0.05 ppm in/on mustard green samples from Treatment Plots 2, 3, and 4, respectively . Max imum residues of HMS were 0.051 ppm, 0.162 ppm, and <0.05 ppm in/on mustard green samples from Treatment Plots 2, 3, and 4, respectively . Maximum total residues were 0.198 ppm, 0.291 ppm, and <0.15 ppm in/on mustard green samples from Treatment Plots 2, 3 , and 4, respectively . T able 7 . Su mma ry of Residue Data from Mustard Green Field Trials with Sulfentrazone . Residue Levels (ppm) Commodity PHI

(days) Trt

Plot No. Total Applic. Rate (lb ai/A) n Min. Max. HAFT 1 Median Mean Std. Dev. Proposed Use P attern: Preplant/preemergence application at a maximum rate of 0.375 lb ai/A Sulfentrazone 2 0.092 - 0.108 14 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- 3 0.199 - 0.222 14 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- Mustard greens, leaves 40 - 66 4 0.402 2 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- DMS 2 0.092 - 0.108 14 <0.05 0.098 0.074 < 0.05 0.053 0.013 3 0.199 - 0.222 14 <0.05 0.136 0.109 < 0.05 0.058 0.024 Mustard greens, leaves 40 - 66 4 0.402 2 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- HMS 2 0.092 - 0.108 1 4 <0.05 0.05 1 0.05 1 < 0.05 < 0.050 0.00 0 3 0.199 - 0.222 14 <0.05 0.162 0.148 < 0.05 0.0 70 0.03 7 Mustard greens, leaves 40 - 66 4 0.402 2 <0.05 <0.05 0.05 < 0.05 < 0.05 -- Total 2 0.092 - 0.108 14 < 0.15 < 0.198 0.174 < 0.15 0.154 0.013 3 0.199 - 0.222 14 < 0.15 < 0.291 0.248 < 0.15 0.178 0.049 Mustard greens, leaves 40 - 66 4 0.402 2 <0.15 <0.15 < 0.15 < 0.15 < 0.15 -- 1 HAFT = h ighest - average f ield trial. For calculation of the total residues , HAFT, median, and mean , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Varying degrees of phy

totoxicity were reported at the FL and GA trial sites. The petitioner noted that crops were stunted by 15% (Treatment Plot 2) and 75% (Treatment Plot 3) at the GA trial site and 20% (Treatment Plot 2) and 45% (Treatment Plot 3) at the FL site. AlthoughSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 19 of 34 

### phy totoxicity was attributed to the test substance application, these isolated instances of phy totoxicity did not have an adverse impact on the residue trials. Conclusions : The submitted residue data for mustard greens , which i s the representative commodity of Brassica leafy greens, subgroup 5B , are adequate to fulfill data requirements provided the use directions are revised to indicate a maximum single and seasonal application rate of 0.20 lb ai/A. The number and locations of crop field trials are in accordance with OPPTS Guideline 860.1500 and the trials conducted reflect the revised proposed use pattern. The residue data for mustard greens indicate that total residues were <0.15 ppm in/on two samples treated at 0.402 lb ai/A (~1.1x). It is noted that higher residues were observed on samples treated at <1.0x. Maximum total residues of <0.198 ppm and <0.291 ppm were reported in/on samples treated at ~0.3x and ~0.5x. The residue data for mustard greens were not entered into the Agency ’s tolerance spreadsheet as specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determine the tolerance level as more than half of the samples (8 of 14) had residues that were less then the LOQ (0.05 ppm) . HED concludes a tolerance level of 0.40 ppm for free and conjugated residues of sulfentrazone, HMS and DMS in/on Brassica leafy greens, subgroup 5B . A revised Section F is required. Vegetable, Legume, Group 6 Pea, succulent 47311406.der.doc 

### IR- 4 has submitted field trial data for sulfentrazone on succulent shelled and edible -podded peas. Eleven pea field trials were conducted in the United States during the 2003 - 2004 growing seasons. Eight field trials were conducted on succulent shelled peas in Zon es 1 (NY; 1 trial), 5 (MI , OH, and WI ; 4 trials), 11 (ID and WA; 2 trials), and 12 (OR; 1 trial). Three edible -podded pea trials were conducted in Zones 2 (NJ; 1 trial) and 10 (CA; 2 trials). Each trial consisted of one untreated plot and two treated plo ts. Each treated plot received a single preemergence broadcast soil application of a 75% DF formulation of sulfentrazone at a rate of ~0.1875 lb ai/A (1x; Treatment Plot 2), or ~0.25 lb ai/A (1.3x; Treatment Plot 3). All applications were made in 20 - 38 GPA spray volumes, without an adjuvant. Mature peas were collected from treatment plots at 52 - to 168 - day PHI s . The results of the field trials show that residues of sulfentrazone, DMS, and HMS were each below the LOQ (<0.05 ppm) in/on samples of peas ( succulent shelled and edible -podded) harvested 52 - 168 days after a single preemergence broadcast application of a 75% DF formulation of sulfentrazone made to soil at target rate s of ~0.1875 lb ai/A (1x; Treatment Plot 2) or ~0.25 lb ai/A (1.3x; Treatment Plo t 3); see Table 8. Total sulfentrazone residues were <0.15 ppm in/on all treated samples of succulent shelled and edible -podded peas.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 20 of 34 T able 8 . Summary of Residue Data from Succulent Pea Field Trials with Sulfentrazone . Residue Levels (ppm) Commodity PHI

(days) Trt

No. To tal Applic. Rate (lb ai/A) n Min. Max. HAFT Median Mean Std. Dev. Proposed Use Pattern: Preemergence application at a maximum rate of 0. 1875 lb ai/A Sulfentrazone 2 0.181 - 0.198 22 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- Pea, succulent shelled and edible - podded 52 - 168 3 0.242 - 0.264 22 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- DMS 2 0.181 - 0.198 22 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- Pea, succulent shelled and edible - podded 52 - 168 3 0.242 - 0.264 22 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- HMS 2 0.181 - 0.198 22 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- Pea, succulent shelled and edible - podded 52 - 168 3 0.242 - 0.264 22 <0.05 <0.05 < 0.05 < 0.05 < 0.05 -- Total 2 0.181 - 0.198 22 < 0.15 <0.15 < 0.15 < 0.15 < 0.15 -- Pea, succulent shelled and edible - podded 52 - 168 3 0.242 - 0.264 22 < 0.15 <0.15 < 0.15 < 0.15 < 0.15 -- 1 HAFT = h ighest - average f ield trial. For calculation of the total residues , HAFT, median, and mean , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Varying degrees of phy

totoxicity were reported at five of the trial sites. The petitioner reported the following phy

totoxic effects: (i) at the NY and OH trials, stunting with slight yellowing which increased with treatment rate, (ii) at the NJ site, whitening and yellowing o f foliage in 20% of plants, (iii) at one CA site crop stunting with lower leaf burning of 50 - 75% of crops. No phy totoxic effects were noted at the six remaining trials. Although phy totoxicity was attributed to the test substance application, these isolated instances of phy totoxicity did not have an adverse impact on the residue trials. Conclusions : The submitted residue data for succulent peas are adequate to fulfill data requirements. The number and locations of crop field trials are in accordance wit h OPPTS Guideline 860.1500 , and the trials conducted reflect the proposed use pattern. The field trial data will support a tolerance of 0.15 ppm for succulent peas. The combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on mature peas ( succulent shelled and edible -podded) following treatment according to the proposed use pattern. A revised Section F is required since the petitioner has proposed a tolerance level of 0. 0 5 ppm for residues in/on mature peas ( succulent shelled and edible -podded) . Vegetable, fruiting, group 8 47311404.der.doc (includes MRID 47311405) 

### IR- 4 has submitted field trial data for sulfentrazone on peppers (bell and non -bell) and tomatoes, the representative commodities of the fruiting vegetables, crop group 8. Twenty- four fruiting vegetable field trials were conducted in the United States during the 2004 growing season. Six bell pepper trials were conducted in Zones 2 (MD; 1 trial), 3 (FL; 1 trial), 5 (WI ; 1 trial), 6 (TX; 1 trial), and 10 (CA; 2 trials). Four non -bell pepper trials were conducted in Zones 2 (GA; 1Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 21 of 34 

### trial), 5 (WI ; 1 trial), 6 (TX; 1 trial), and 10 (NM; 1 trial). Fourteen tomato trials were conducted in Zones 1 (NY; 1 trial), 2 (MD and NC; 2 trials), 3 (FL; 2 trials), 5 (MI ; 1 trial), and 10 (CA and NM; 8 trials). Each trial consisted of one untreated plot and multiple (at least two) treatment plots. Each treatment plot received one banded application to the soil surface made at pre - transplant stage followed by one postemergence application between rows using a shielded/hooded sprayer. Treatment Plots 2, 3, and 4 were treated with a 4 lb/gal FlC formulation whereas Treatment Plots 5 and 6 were treated with a 75% DF for mulation of sulfentrazone. Treatment Plots 2 and 5 received two applications at ~0.250 lb ai/A for a total rate of ~0.500 lb ai/A (1.3x). Treatment Plots 3 and 6 received two applications at ~0.375 lb ai/A for a total rate of ~0.750 lb ai/A (2.0x). Treatment Plot 4 received two applications at ~0.200 lb ai/A for a total rate of ~0.4 00 lb ai/A (1.1x). Peppers were treated at a 47 - to 84 - day RTI , and tomatoes were treated at a 34 - to 99 - day RTI . The second application made to each tomato treated plot at the MD site was over- applied by ~64%. Mature peppers and tomatoes were collected at 19 - to 22 - day PHI s . The crop field study shows that residues of sulfentrazone, DMS, and HMS were each <LOQ (<0.05 ppm) in/on all samples of peppers and tomatoes harvested 19 - 22 days following the last of two applications (a soil surface, pre - transplant, banded application followed by a postemergence application made between rows with a shielded/hooded sprayer) of either a 4 lb/gal FlC formulation or a 75% DF formulation of sulfentrazone, at total rates of 0.40 lb ai/A (1.1x) , 0.50 lb ai/A (1.3x) , and 0 .75 lb ai/A (2.0x); see Table 9 . Total combined residue s of sulfentrazone, DMS, and HMS were all <0.15 ppm in/on all treated samples of peppers and tomatoes. No residue decline data were submitted; however, decline data are not required because residues were nonquantifiable at the earliest harvest time. T able 9. Summary of Residue Data from Fruiting Vegetable Field Trials with Sulfentrazone . Residue Levels (ppm) Commodity PHI

(days) Trt

Plot No. Total Applic. Rate (lb ai/A) n Min. Max. HAF T 1 Median Mean Std. Dev. Proposed Use Pattern: Preplant or post emergence application at a maximum seasonal rate of 0. 375 lb ai/A Sulfentrazone 2 0.505 - 0.512 12 <0.05 <0.05 <0.05 <0.05 <0.05 -- 19 - 21 3 0.739 - 0.773 12 <0.05 <0.05 <0.05 <0.05 <0. 05 --

4 0.410 2 <0.05 <0.05 <0.05 <0.05 <0.05 -- 5 0.504 - 0.507 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- Bell Pepper 21 6 0.758 - 0.779 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- 2 0.499 - 0.505 8 <0.05 <0.05 <0.05 <0.05 <0.05 -- Non - bell pepper 19 - 22 3 0.750 - 0.761 8 <0.05 < 0.05 <0.05 <0.05 <0.05 -- 2 0.489 - 1.004 28 <0.05 <0.05 <0.05 <0.05 <0.05 -- 19 - 21 3 0.730 - 0.982 28 <0.05 <0.05 <0.05 <0.05 <0.05 -- 21 4 0.537 2 <0.05 <0.05 <0.05 <0.05 <0.05 --

5 0.490 - 0.504 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- Tomato 19 - 21 6 0.7 39 - 0.758 4 <0.05 <0.05 <0.05 <0.05 <0.05 --Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 22 of 34 DMS 2 0.505 - 0.512 12 <0.05 <0.05 <0.05 <0.05 <0.05 -- 19 - 21 3 0.739 - 0.773 12 <0.05 <0.05 <0.05 <0.05 <0.05 --

4 0.410 2 <0.05 <0.05 <0.05 <0.05 <0.05 -- 5 0.504 - 0.507 4 <0.05 <0.05 <0.0 5 <0.05 <0.05 -- Bell Pepper 21 6 0.758 - 0.779 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- 2 0.499 - 0.505 8 <0.05 <0.05 <0.05 <0.05 <0.05 -- Non - bell pepper 19 - 22 3 0.750 - 0.761 8 <0.05 <0.05 <0.05 <0.05 <0.05 -- 2 0.489 - 1.004 28 <0.05 <0.05 <0.05 <0.05 <0.05 -- 19 - 21 3 0.730 - 0.982 28 <0.05 <0.05 <0.05 <0.05 <0.05 -- 21 4 0.537 2 <0.05 <0.05 <0.05 <0.05 <0.05 --

5 0.490 - 0.504 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- Tomato 19 - 21 6 0.739 - 0.758 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- HMS 2 0.505 - 0.512 12 <0.0 5 <0.05 <0.05 <0.05 <0.05 -- 19 - 21 3 0.739 - 0.773 12 <0.05 <0.05 <0.05 <0.05 <0.05 --

4 0.410 2 <0.05 <0.05 <0.05 <0.05 <0.05 -- 5 0.504 - 0.507 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- Bell Pepper 21 6 0.758 - 0.779 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- 2 0.499 - 0.505 8 <0.05 <0.05 <0.05 <0.05 <0.05 -- Non - bell pepper 19 - 22 3 0.750 - 0.761 8 <0.05 <0.05 <0.05 <0.05 <0.05 -- 2 0.489 - 1.004 28 <0.05 <0.05 <0.05 <0.05 <0.05 -- 19 - 21 3 0.730 - 0.982 28 <0.05 <0.05 <0.05 <0.05 <0.05 -- 21 4 0.537 2 <0.05 <0.05 <0.05 <0.0 5 <0.05 --

5 0.490 - 0.504 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- Tomato 19 - 21 6 0.739 - 0.758 4 <0.05 <0.05 <0.05 <0.05 <0.05 -- Total 2 0.505 - 0.512 12 <0.15 <0.15 <0.15 <0.15 <0.15 -- 19 - 21 3 0.739 - 0.773 12 <0.15 <0.15 <0.15 <0.15 <0.15 --

4 0.410 2 <0.15 <0.15 <0.15 <0.15 <0.15 -- 5 0.504 - 0.507 4 <0.15 <0.15 <0.15 <0.15 <0.15 -- Bell Pepper 21 6 0.758 - 0.779 4 <0.15 <0.15 <0.15 <0.15 <0.15 -- 2 0.499 - 0.505 8 <0.15 <0.15 <0.15 <0.15 <0.15 -- Non - bell pepper 19 - 22 3 0.750 - 0.761 8 <0.15 <0.15 <0.15 <0 .15 <0.15 -- 2 0.489 - 1.004 28 <0.15 <0.15 <0.15 <0.15 <0.15 -- 19 - 21 3 0.730 - 0.982 28 <0.15 <0.15 <0.15 <0.15 <0.15 -- 21 4 0.537 2 <0.15 <0.15 <0.15 <0.15 <0.15 --

5 0.490 - 0.504 4 <0.15 <0.15 <0.15 <0.15 <0.15 -- Tomato 19 - 21 6 0.739 - 0.758 4 <0 .15 <0.15 <0.15 <0.15 <0.15 -- 1 HAFT = h ighest - average f ield trial. For calculation of the total residues , HAFT, median, and mean , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Conclusions : The submitted residue data for peppers (bell and non -bell) and tomatoes are adequate. The number and locations of crop field trials are in accordance with OPPTS Guideline 860.1500 and the trials conducted reflect the proposed use pattern. The field trial data will support a tolerance of 0.15 ppm for residues in/on fruiting vegetables, crop group 8 . Following two applications (a soil surface, pre - transplant, banded application followed by a postemergence application made between rows with a shielded/hooded sprayer) of representativ e formulations at

~ 1.1 - 2.0x, the combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on theSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 23 of 34 

### representative commodities. A revised Section B is required to remove postemergence uses on the labels since metabolism data are not available to su pport this use pattern. A revised Section F is also required since the petitioner has proposed a crop group tolerance level of 0.05 ppm. Okra O kra residue data were not submitted in support the proposed use on okra. IR- 4 has propos ed to translate the existing and submitted fruiting vegetable data (peppers and tomatoes) to okra. The proposed use on okra is identical to the proposed use on the fruiting vegetables crop group. HED has approved adding okra to the fruiting vegetable crop group (see minutes of ChemSAC meeting of 10/18/06 ) . Until 40 CFR § 180.41 is updated, a separate tolerance must be established for residues in/on okra. Conclusions . The available data for the fruiting vegetable s, crop group 8 may used to support the proposed tolerance for residues in/on okra. The tolerance should be established at the same level as the fruiting vegetable group tolerance, 0.15 ppm. Melon subgroup 9A 4 7311403.der.doc 

### IR- 4 has submitted field trial data for sulfentrazone on cantaloupe, the representative c ommodity of the melon subgroup 9A. Eight field trials were conducted on cantaloupe in the United States in Zones 1 (NY; 1 trial), 2 (NC; 1 trial), 5 (WI ; 1 trial), 6 (TX; 1 trial), 9 (CO; 1 trial), and 10 (CA and NM; 3 trials) during the 2002 growing seas on. Each trial consisted of one untreated plot and two treated plots, except for one trial (NY) which had three treated plots. Each treated plot received a single broadcast application of a 75% DF formulation of sulfentrazone to soil surface at pre - transplant or preemergence at rates of ~ 0.20 lb ai/A ( 0.8x; Treatment Plot 2), ~ 0.25 lb ai/A ( 1.0x; Treatment Plot 3) or ~ 0.15 lb ai/A ( 0.6x; Treatment Plot 4) . Applications were made in 21 - 42 GPA, without an adjuvant. Mature cantaloupes were collected from the fields at 59 - to 94 - day PHI s . The results of the field trials indicate that residues of sulfentrazone, DMS, and HMS were below the LOQ (<0.05 ppm) in/on all samples of cantaloupe harvested 59 - 94 days after a single broadcast application of a 75% DF for mulation of sulfentrazone to soil surface at pre - transplant or preemergence at rates of ~ 0.20 lb ai/A (Treatment Plot 2), ~ 0.25 lb ai/A (Treatment Plot 3) or

~ 0.15 lb ai/A (Treatment Plot 4) , with one exception ; see Table 10 . In one CA trial, residues of HMS were 0.052 ppm in/on cantaloupe samples from Treatment Plot 2. Maximum total residues were <0.152 ppm, <0.15 ppm, and <0.15 ppm in/on cantaloupes from Treatment Plots 2, 3, and 4, respectively .Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 24 of 34 T able 10 . Summary of Residue Data from C antaloupe Fiel d Trials with Sulfentrazone . Residue Levels (ppm) Commodity PHI

(days) Trt

No. Total Applic. Rate (lb ai/A) n Min. Max. HAFT 1 Median Mean Std. Dev. Proposed Use Pattern: Pre emergence application at a maximum seasonal rate of 0. 25 lb ai/A Sulfentr azone 2 0.20 - 0.22 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- 3 0.25 - 0.27 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- Cantaloupe, fruit 59 - 94 4 0.16 2 <0.05 <0.05 <0.05 <0.05 <0.05 -- DMS 2 0.20 - 0.22 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- 3 0.25 - 0.27 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- Cantaloupe, fruit 59 - 94 4 0.16 2 <0.05 <0.05 <0.05 <0.05 <0.05 -- HMS 2 0.20 - 0.22 16 <0.05 0.052 0.051 <0.05 <0.05 -- 3 0.25 - 0.27 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- Cantaloupe, fruit 59 - 94 4 0.16 2 <0.05 <0.05 <0.05 <0.0 5 <0.05 -- Total 2 0.20 - 0.22 16 <0.15 <0.15 2 < 0.15 1 <0.15 <0.15 -- 3 0.25 - 0.27 16 <0.15 <0.15 <0.15 <0.15 <0.15 -- Cantaloupe, fruit 59 - 94 4 0.16 2 <0.15 <0.15 <0.15 <0.15 <0.15 -- 1 HAFT = h ighest - average f ield trial. For calculation of the total residues , HAFT, median, and mean , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Varying degrees of phy

totoxicity were reported at four trial sites (CA; 2 trials, NC, and NY). The petitioner noted that leaf crinkling, n ecrosis, and stunted growth were observed in crops at the NY site, crops from the NC site had marginal and intervenal necrosis, and crops from two CA trials were reported to have stunted growth, leaf discoloration, burning, and distortion. Although phy

totoxicity was attributed to the test substance application, these isolated instances of phy totoxicity did not have an adverse impact on the residue trials. Conclusion s: The submitted residue data for cantaloupes are adequate to support a tolerance of 0.15 ppm for residues in/on the melon subgroup 9A. The number and locations of crop field trials are in accordance with OPPTS Guideline 860.1500 , and the trials conducted reflect the proposed use pattern. Following pre - transplant or preemergence a pplication o f a representative formulation at ~ 0.6 - 1 .0x, the combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on mature cantaloupes . A revised Section F is required since the petitioner has proposed a crop sub group tolerance level of 0. 1 0 ppm.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### Strawberry 47311408.der.doc 

### IR- 4 has submitted field trial data for sulfentrazone on strawberry . Eight strawberry field trials were conducted in the United S tates during the 2003 growing season. Three perennial strawberry trials were conducted in Zones 2 (NJ; 1 trial), 5 (MI ; 1 trial), and 12 (OR; 1 trial). Five annual strawberry trials were conducted in Zones 3 (FL; 2 trials), and 10 (CA; 3 trials). Each trial site consisted of one untreated plot and two treated plots. Each treated plot received one bro adcast soil application of a 75% DF formulation of sulfentrazone at pre -plant (annual strawberry crops) or during the dormant phase (perennial strawberry crops) at a rate of 0.25 - 0.26 lb ai/A ( 1.0x; Treatment Plot 2) or 0.38 - 0.40 lb ai/A ( 1.6x; Treatment P lot 3), in 20 - 35 GPA spray volumes, without an adjuvant. Mature strawberries were harvested at 56 - to 189 - day PHI s . The results of the field trials show that residues of sulfentrazone, DMS, and HMS were each <LOQ (0.05 ppm) in/on all samples of strawberry harvested 56 - 189 days following a single b roadcast soil application of a 75% DF formulation of sulfentrazone made preplant (annual strawberry crops) or during the dormant phase (perennial strawberry crops) at a rate of 0.25 - 0.26 lb ai/A (Treatment Plot 2) or 0.38 - 0.40 lb ai/A (Treatment Plot 3) ; see Table 11 . Total sulfentrazone residues were <0.15 ppm in/on all treated samples of strawberry . T able 11 . Summary of Residue Da ta from Strawberry Field Trials with Sulfentrazone . Residue Levels (ppm) Commodity Total Applic.

Rate (lb ai/A) PHI

(days) n Min. Max. HAFT 1 Median Mean Std. Dev. Proposed Use Pattern: Pre emergence application at a maximum seasonal rate of 0. 25 lb ai/A Sulfentrazone 0.25 - 0.26 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- Strawberry 0.38 - 0.40 56 - 189 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- DMS 0.25 - 0.26 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- Strawberry 0.38 - 0.40 56 - 189 16 <0.05 <0.05 <0.05 <0.05 <0.05 -- HMS 0.25 - 0.26 16 <0.05 <0.05 0.05 0.05 <0.05 -- Strawberry 0.38 - 0.40 56 - 189 16 <0.05 <0.05 0.05 0.05 <0.05 -- Total 0.25 - 0.26 16 <0.15 <0.15 <0.15 <0.15 <0.15 -- Strawberry 0.38 - 0.40 56 - 189 16 <0.15 <0.15 <0.15 <0.15 <0.15 -- 1 HAFT = h ighest - average f ield trial. For calculation of the total residues , HAFT, median, and mean , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Varying degrees of phy

totoxicity were reported at the MI trial site and two CA trial sites. At the MI trial site, there was a 25 - 30% reduction in size in Treatment Plot 2 and a 40% reduction Treatment Plot 3. At the Salinas, CA trial, a few weeks after application, there were signs of phy totoxicity in both treated plots, with the Treatment Plot 3 being more affected. By the end of the growing season, the Treatment Plot 2 plants were stunted with 5 - 8% dead or missing plants and the Treatment Plot 3 was 25 - 30% dead, with the remainder 25% stunted, producing little or no fruit. At the Watsonville, CA trial, a few weeks after application, there were signs of similar levels of phy

totoxicity in both treated plots. By the end of the growing season, the treated plots had fewer plants with fruit than the control plot and no mature berries. In addition, the plantsSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 26 of 34 

### were not uniform. Treatment Plot 3 also had many small plants throughout the plot. No phy totoxic effects were noted at the five remaining trials. Conclusions : The submitted residue data for strawberries are adequate to fulfill data requirements. The number and locations of crop field trials are in accordance with OPPTS Guideline 860.1500 , and the trials conducted reflect the proposed use pattern. The field trial data support a tolerance of 0.15 ppm for residues in/on strawberry . The combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on mature strawberrie s following a pre -plant or dormant application of a representative sulfentrazone formulation at 1.0 - 1 . 6x . A revised Section F is required since the petitioner has proposed a tolerance level of 0.05 ppm for residues in/on strawberries. Flax 47311407.de 1 . doc 

### IR- 4 has submitted field trial data for sulfentrazone on flax. Six flax field trials were conducted in the United States in Zones 5 (ND; 3 trials) and 7 (SD; 3 trials) during the 2002 growing season. Each trial consisted of one untreated and one tre ated plot. The treated plots received a single preemergence broadcast soil application of a 75% DF formulation or a mixture of two 75% DF formulations of sulfentrazone at a rate of ~0.375 lb ai/A (1.0x), in 18 - 20 GPA spray volumes, without an adjuvant. F lax seed was harvested at 111 - to 123 - day PHI s . The results of the field trials indicate that residues of sulfentrazone, DMS, and HMS were each <LOQ (0.05 ppm) in/on all samples of flax seed harvested 111 - 123 days after a single preemergence broadcast soil application of a 75% DF formulation or mixture of two 75% DF formulations of sulfentrazone at a rate of ~0.375 lb ai/A; see Table 12. Total sulfentrazone residues were <0.15 ppm in/on all treated samples of flax seed. T able 12 . Summary of Residue Da ta from Flax Field Trials with Sulfentrazone . Residue Levels (ppm) Commodity Total Applic.

Rate (lb ai/A) PHI

(days) n Min. Max. HAFT 1 Median Mean Std. Dev. Proposed Use Pattern: Pre emergence application at a maximum seasonal rate of 0. 375 lb ai/A Su lfentrazone Flax, seed 0.365 - 0.383 111 - 123 12 <0.05 <0.05 <0.05 <0.05 <0.05 -- DMS Flax, seed 0.365 - 0.383 111 - 123 12 <0.05 <0.05 <0.05 <0.05 <0.05 -- HMS Flax, seed 0.365 - 0.383 111 - 123 12 <0.05 <0.05 <0.05 <0.05 <0.05 -- Total Flax, seed 0.365 - 0.383 111 - 123 12 <0.15 <0.15 <0.15 <0.15 <0.15 -- 1 HAFT = h ighest - average f ield trial. For calculation of the total residues , HAFT, median, and mean , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Conclusions : The submitted residue data for flax are adequate to fulfill the data requirements. The number and locations of crop field trials are in accordance with OPPTS Guideline 860.1500 , and the trials conducted reflect the proposed use pattern. The field trial data will supp ort a tolerance of 0.15 ppm for residues in/on flax seed . The combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on flax seed following a preemergence application of aSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 27 of 34 

### representative sulfentrazone formulation at 1.0x. A revised Section F is required since the petitioner has proposed a tolerance for residues in/on flax seed at 0.05 ppm. 860.1520 Processed Food and Feed Flax 47311407.de2.doc 

### IR- 4 has submitted processing data for sulfentrazone on flax. In one trial conducted in ND during the 2002 growing season, flax seed was harvested 123 days following a single preemergence broadcast soil application of a 75% DF formulation of sulfentrazone at a rate of 0.3718 lb ai/A (~1x), without an adjuvant. The harvested flax seeds were processed into meal and oil using simulated commercial processing procedures. The processing study indicates that all residues of sulfentrazone, DMS, and HMS were <LOQ (0.05 ppm) in flax seed (RAC), meal, and oil; see Table 13. Since all residues were <LOQ, proce ssing factors (PF) could not be calculated (NC). It is noted that no phy totoxic effects were reported following application of the test substance. T abl e 13. Residue Data from a Flax Processing Study with Sulfentrazone. Sulfentrazone DMS HMS Total Processed Commodity Total Rate (lb ai/A) PHI

(days) Residues

(ppm) PF Residues

(ppm) PF Residues

(ppm) PF Residues

(ppm) PF Flax, seed (RAC) <0.05 -- <0.05 -- <0.05 -- <0.15 -- Flax, meal <0.05 NC <0.05 NC <0.05 NC <0.15 NC Flax, oil 0.3718 123 <0.05 NC <0.05 NC <0.05 NC <0.15 NC 

### Conclusions : The submitted flax processing study is unacceptable for regulatory purposes since the study has not conclusively demonstrated that sulfentrazone residues of concern will not concentrate in flax meal and oil as a result of the proposed use. Quantifiable residues were not detected in the flax seeds used for processing, and the field trial was conducted at only a 1x rate. Since no phy

totoxic effects were reported, the flax processing study needs to be repe ated using an exaggerated application rate ( equal to the maximum theoretical concentration factor for flax or 5x , whichever is less ) . Tomato 47311405.der.doc 

### IR- 4 has submitted the results of a tomato processing study with sulfentrazone. Samples used f or processing were generated from a field trial conducted in CA during the 2004 growing season. Tomatoes were harvested 20 days following two applications ( one banded application to soil surface pre - transplant and one postemergence application between row s using a shielded/hooded sprayer) of a 4 lb/gal flowable concentrate (FlC) formulation of sulfentrazone, applied at rates of ~0.250 lb ai/A/application, for a total rate of ~0.500 lb ai/A (~1.3x; Treatment Plot 2) or at ~0.375 lb ai/A/application, for a total rate of ~0.750 lb ai/A (2.0x; Treatment Plot 3). Applications were made at a 99 - day RTI , in 25 - 31 GPA spray volumes, without an adjuvant. The collected tomato samples were processed into paste and puree using simulated commercialSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 28 of 34 

### procedures. The processing study indicates that all residues of sulfentrazone, DMS, and HMS were <LOQ (<0.05 ppm) in/on tomato fruit , paste, and puree; see Table 14. Since all residues were <LOQ, processing factors could not be calculated. The study reported that phy totox ic effects occurred after the first application but the crops fully recovered by the second application. The maximum theoretical concentration factors are 5.5x for processing to tomato paste (OPPTS 860.1520, Table 1). T able 14. Residue Data from a Tom a to Processing Study with Sulfentrazone. Sulfentrazone DMS HMS Total Processed Commodity Total Rate (lb ai/A) PHI

(days) Residues

(ppm) PF Residues

(ppm) PF Residues

(ppm) PF Residues

(ppm) PF 0.5006 <0.05

<0.05 -- <0.05

< 0.05 -- <0.05

<0.05 -- <0.15

<0.15 -- Tomato, fruit (RAC) 0.7607 <0.05 <0.05 NC

NC <0.05 <0.05 NC

NC <0.05 <0.05 NC

NC <0.15 <0.15 NC

NC 0.5006 <0.05

<0.05 NC

NC <0.05 <0.05 NC

NC <0.05 <0.05 NC

NC <0.15 <0.15 NC

NC Tomato, paste 0.7607 <0.05 <0.05 NC

NC <0.05 <0.05 N C

NC <0.05 <0.05 NC

NC <0.15 <0.15 NC

NC 0.5006 <0.05

<0.05 NC

NC <0.05 <0.05 NC

NC <0.05 <0.05 NC

NC <0.15 <0.15 NC

NC Tomato, puree 0.7607 20

<0.05 <0.05 NC

NC <0.05 <0.05 NC

NC <0.05 <0.05 NC

NC <0.15 <0.15 NC

NC 1 For calculation of the total residues , the LOQ value ( < 0.05 ppm) was used for all residues reported as below the LOQ. 

### Conclusions : The submitted tomato processing study is unacceptable since the study does not conclusively demonstrated that sulfentrazone residues of concern will not conc entrate in tomato paste and puree as a result of the proposed use. Although the petitioner reported phy totoxic effects after the first application, these plants recovered by the second application. Therefore, an attempt should be made to apply sulfentraz one at an exaggerated rate (equal to the maximum theoretical concentration factor or 5x, whichever is less) to obtain sample s with quantifiable residues so that processing factors may be determined. 860.1650 Submittal of Analytical Reference Standards Analy tical standards for sulfentrazone and its metabolites DMS and HMS are currently available at the EPA National Pesticide Standards Repository (personal communication with Dallas Wright, ACB, 4/21 /0 8 ) . However, the standard s for sul fentrazone and its metabolite DMS will expire 10/1/2012 and 5/1/2012, respectively, and the standard for its metabolite HMS has expired 4/ 1/200 8 . The registrant must either recertify the lot in the repository and send an updated certificate of analysis (C OA), or submit new standards (different lot #) if the previous lots will not be recertified. If new COAs are being submitted, they should be faxed to the repository at 410 - 305 - 2999. If new standards are being submitted, they should be sent to the Analy ti cal Chemistry Lab, which is located at Fort Meade , to the attention of either Theresa Cole or Thuy Nygen at the following address:Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

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### USEPA National Pesticide Standards Repository /Analy tical Chemistry Branch/OPP 701 Mapes Road Fort George G. Meade, MD 2 0755 - 5350 (Note that the mail will be returned if the extended zip code is not used.) 860.1850 /1900 Confined/Field Accumulation in Rotational Crops Rotational crop studies for corn, rice, sorghum, and wheat were previously submitted in conjunction with the soy

bean petition (PP#4F 0 4407). Permanent tolerances have been established for indirect or inadvertent residues of sulfentrazone and its metabolites, HMS and DMS, in cereal grains (excluding sweet corn), bran, forage, grain, hay, hulls, stover, and straw as a result of the use on soy

beans . As the 1x use rate in soy beans (0.375 lb ai/A) is ≥ the 1x use rate of the proposed new uses, the established tolerances for indirect or inadvertent residues of sulfentrazone and its metabolites, HMS and DMS are adequate to support the subject petition. The proposed rotational crop restrictions are adequate and consistent with previous sulfentrazone petitions. 860.1550 Proposed Tolerances The HED Metabolism Committee has determined that the parent compound, sulfentrazone, and the metabolite HMS are the residues of concern in soy beans, and that sulfentrazone and the metabolites HMS and DMS are the residues of concern in rotational crops (D226434, 6/14/96, G. Kramer). As the enforcement method for plant commodities determines free and conjugated forms of the analy

tes, the tolerance expression should be revised to indicate the residues of concern are the combined residues of free and conjugated sulfentrazone, and its metabolites HMS and DMS. Sulfentrazone tolerances are currently estab lished under 40 CFR §180.498 . A tolerance is established under 40 CFR §180.498(a)(1) for the combined residues of sulfentrazone and it s major metabolite, HMS, in/on soy bean seed at 0.05 ppm. P ermanent tolerances are established under 40 CFR §180.498(a)(2 ) for the combined residues of sulfentrazone and its metabolites HMS and DMS in/on several food commodities; these established tolerances range from 0.15 ppm (various plant commodities) to 0.40 ppm (peanut meal). Time - limited tolerances for the combined residues of sulfentrazone and its metabolites HMS and DMS have been established under 40 CFR § 180.498(b) in connection with Section 18 Emergency Exemptions ; these include tolerances for bean, succulent seed without pod (lima bean & cowpea) at 0.1 ppm with a 12/31/07 expiration date, flax seed at 0.2 ppm with a 12/31/10 expiration date, and strawberry at 0.60 ppm with a 12/31/10 expiration date. Finally, tolerances are established under 40 CFR § 180.498(d) for inadvertent and indirect combined residues of sul fentrazone and its metabolites HMS and DMS in/on cereal grain (excluding sweet corn) bran, forage, grain, hay, hulls, stover, and straw at 0.1 - 0.6 ppm as a result of the application of sulfentrazone to growing crops. The proposed tolerance expression in the current petition should be revised to indicate tolerances for combined residues of free and conjugated sulfentrazone and its metabolites HMS and DMS are the residues of concern.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 30 of 34 

### Pending submission of a revised Section F as specified in Table 15, adeq uate crop field trial data have been submitted for: broccoli, one of the representative commodities of head and stem Brassica (subgroup 5A); provided the proposed use directions are modified, mustard greens, the sole representative commodity of Brassica l eafy greens (subgroup 5B); peas (succulent and edible -podded); bell and non -bell peppers and tomatoes, the representative commodities of fruiting vegetables (group 8); cantaloupe, the sole representative commodity of melon subgroup (subgroup 9A); strawberries; and flax. The submitted data showed that the combined residues of sulfentrazone, DMS, and HMS were <0.15 ppm in/on mature commodities listed above following application(s) of a representative formulation of sulfentrazone according to the proposed crop use pattern. It is, however, noted that higher residues were observed in/on mustard green samples treated at <1.0x. The field trial data are supported by adequate storage stability data, and no corrections need to be applied on the observed residues. A revised Section B must be submitted to remove the proposed postemergence use on fruiting vegetables. The residue data for mustard greens were not entered into the Agency ’s tolerance spreadsheet as specified by the Guidance for Setting Pesticide Toleranc es Based on Field Trial Data SOP to determine the tolerance level as more than half of the samples (8 of 14) had residues that were less then the LOQ (0.05 ppm). HED concludes a tolerance level of 0.40 ppm for combined residues of free and conjugated sulf entrazone, HMS and DMS in/on Brassica leafy greens, subgroup 5B . A revised Section F is required. The previously reviewed data for potato, the representative commodity of tuberous and corm vegetables (subgroup 1C) may be used to support the requested use pattern for the subgroup. These data were submitted as part of PP # 2 E6405 (DP#s 287102 , 1/10/03, G. Kramer) and showed that the maximum combined residues of sulfentrazone and its metabolites HMS and DMS were 0.077 ppm in/on potato tubers after a preemerg ence treatment at 1x. The previously reviewed data for cabbage, another representative commodity of head and stem Brassica (subgroup 5A) may be used to support the requested use pattern for the subgroup. These data were submitted in conjunction with PP#1 E6311 (DP# 276111, 12/9/02, G. Kramer) and indicate that the combined residues of sulfentrazone, HMS, and SCA (quanti fied as DMS) were <0.15 - 0.18 ppm and <0.15 - 0.17 ppm in/on cabbage heads with and without wrapper leaves, respectively, following applicatio n at 1x . The petition review concluded that two additional cabbage field trials should be conducted in Regions 1 and 8 as a condition for full registration. These trials are no longer needed since an adequate number of broccoli and cabbage field trials are available to satisfy geographic representation for head and stem Brassica , subgroup 5A. The submitted data for the fruiting vegetables may used to support the proposed use on okra. New flax and tomato processing studies are required. No Codex , Canadi an, or Mexican MRL s have been established for sulfentrazone on the subject crops; therefore, harmonization of MRL s and U.S. tolerances is not an issue at this time . An International Residue Limit (IRL) form is appended to this Summary Document and follows this section. A tolerance summary for sulfentrazone is presented in Table 15 .Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 31 of 34 Table 15 . Tolerance Summa ry for Sulfentrazone . Commodity Proposed T olerance (ppm) Recommended

Tolerance (ppm) Comments Brassica , head and stem, subgroup 5A 0.20 0.20 The e stablished tolerance for cabbage under 180.498(a)(2) should be removed concomitantly when the subgroup 5A tolerance is established Brassica , leafy greens, subgroup 5B 0.35 0.40 Melon subgroup 9A 0.10 0.15 Vegetable, fruiting, group 8 0.05 0.15 Okra 0.05 0.15 Pea, succulent 0.05 0.15 Flax 0.05 0.15 The established time limited tolerance for flax seed under 180.498(b) should be removed concomitantly when the permanent flax tolerance is established. Straw berry 0.05 0.15 The established time limited tolerance for straw

berry under 180.498(b) should be removed concomitantly when the permanent strawberry tolerance is established. Vegetable, tuberous and corm, subgroup 1C 0.15 0.15 Tolerance recommendation is based on residue data translated from potato . T he established tolerance for potato under 180.498(a)(2) should be removed concomitantly when the subgroup 1C tolerance is established. 

### References DP # : 288712 Subject: Sulfentrazone

– Briefing Memorandum for Meeting of Metabolism Assessment

Review C ommittee From: G. Kramer To: Y. Donovan Dated: 3 / 6 /03 MRID(s): NoneSulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 32 of 34 

### DP #s : 287102, 286879, 287256, 287257 Subject: PP#s 2F6391, 2E6498, 2E6405 & 2E6500. Sulfentrazone in/on Dried Shelled Pea

and Bean, Field Corn, Succulent Lima Bean, Potatoes and Asparagus. Summary of Analy tical Chemistry and Residue Data. From: G. Kramer To: D. Morgan/J. Miller Dated: 1 / 10/03 MRID(s): 45537402, 45567404, 45739201, 45582201, 45752601, 45567403, 45582201 DP # : 276111 Subject: PP# 1E6311. Sulfentrazone on Cabbage, Horseradish, and Mint. Evaluation of

Residue Data and Analy

tical Methods. From: G. Kramer To: S. Brothers/R. Forrest Dated: 12 / 9 /02 MRID(s): 45393501 and 45393502 DP # : 233520 Subject: PP# 4F04407. Sulfentrazone (Authority Herbicide) for Use on Soy be ans. Results of Petition Method Validation (PMV). From: G. Kramer To: S. Robbins/K. Boyle Dated: 3 /25 / 97 MRID(s): 44118801 and 44118802 DP # : 226434 Subject: HED Metabolism Committee of 5/20/96. Sulfentrazone. PP#4F04407. From: G. Kramer To: HED M etabolism Committee Members Dated: 6 / 14/ 96 MRID(s): None DP # : 220548 Subject: PP# 4F04407. Sulfentrazone for Use on Soy beans. Data Waiver Request. From: G. Kramer To: J. Miller Dated: 3 / 13 / 96 MRID(s): None DP # : None Subject: Multiresidue Method T esting of sulfentrazone and 3 - hydroxy methyl

sulfentrazone. From: G. Kramer To: H. Hundley Dated: 2 /7 / 95 MRID(s): 43345416Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 33 of 34 

### Attachments: International Residue Limit Status sheet DOCUMENT TRACKING RDI : RAB1 Chemistry Team: 08 /20/2008 Petition Number: 7E7308 DP#: 349321 PC Code: 129081 Template Version September 2005Sulfentrazone Summary of Analytical Chemistry and Residue Data DP#: 349321

Page 34 of 34 

# INTERNATIONAL RESIDUE LIMIT STATUS Chemical Name: N - [2,4 - dichloro - 5 - [4 - (difluoromethyl) - 4,5 - dihydro - 3 - methyl - 5 - oxo 1H - 1,2,4 - triazol - 1 - yl]phenyl]methanesulfona mide Common Name: Sulfentrazone X Proposed tolerance ⁬ Reevaluated tolerance ⁬ Other Date: 4/17/08

Codex Status (Maximum Residue Limits) U. S. Tolerances X No Codex proposal step 6 or above ⁬ No Codex proposal step 6 or above for the crops requested Petition Number: PP#7E7308 DP#: 349321 Other Identifier: Reviewer/Branch: J. Tyler/RAB1 Residue definition (step 8/CXL): N/A Residue definition: C om bined residues of sulfentrazone and its metabolites 3 - hydroxymethyl sulfentrazone (HMS) and 3 - desmethyl sulfentrazone (DMS) Crop (s) MRL (mg/kg) Crop(s) Tolerance (ppm) Brassica , head and stem, subgroup 5A 0.20 Brassica , leafy greens, subgroup 5B 0.35 Melon, subgroup 9A 0.10 Vegetable, fruiting, group 8 0.05 Okra 0.05 Pea, succulent 0.0 5 Flax 0.05 Straw berry 0.05 Vegetable, tuberous and corm, subgroup 1C 0.15 Limits for Canada Limits for Mexico X No Limits ⁬ No Limits for the crops requested ⁬ No Limits X No Limits for the crops requested Residue definition: N/A Residue def inition: sulfentrazone Crop(s) MRL (mg/kg) Crop(s) MRL (mg/kg)

Notes/Special Instructions: S.Funk, 04/28/2008.