Page 1 of 13 **UNITED STA TES ENVIRONMENTA**  **L PROTECTION A GENCY** 

**WA SHINGTON, D.C. 20460**  **OFFICE OF CHEMICAL SAFETY AND**  **POLLUTION PREVENTION MEMORANDUM**  **Date:** 05 - JUN - 2014 **Subject :**  **Sulfentrazone** . Section 3 Registration Request to Add New Use on Apples .

**Summary of Analytical Chemistry and Residue Data. PC Code:**  129081 **DP Barcode:** D 415626 **Decision No.:** 4 83232 **Registration No s**  **. :**  279 - 3370, 279 - 3189, & 279 - 3220 **Petition No.:** 3E8202 **Regulatory Action:** Amended Section 3 **Risk Assessment Type:** NA **Case No.:** 7231 **T XR No.:**  NA **CAS No.:** 122836 - 35 - 5 **MRID No.:** 49124501 **40 CFR:** § 180. 498 **From:** George F. Kramer, Ph.D., Branch Senior Chemist

Registration Action Branch 1 (RAB1) Health Effects Division (HED, 7509P) **Through:** Charles W. Smith III, Branch Chief

RAB1/HED (7509P) **To:** Laura Nollen/Barbara Madden, RM 05

Registration Division (RD, 7505P) **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 protoporphyrinogen oxidase (PPO) inhibition. Sulfentrazone acts by the same mechanism as the diphenyl ether herbicides in which membrane disruption is initiated by the inhibition 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 Project No. 4 (IR - 4) has submitted a petition proposing the establishment of permanent tolerances for the combined residues of the free and conjugated forms of sulfentrazone, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the proposed tolerance levels specified below is to be determined by measuring only

the sum of sulfentrazone ( N - [2,4 - dichloro - 5 - [4 - (difluoromethyl) - 4,5 - dihydro 3 - methyl - 5 - oxo - 1 H

- 1,2,4 - triazol - 1 - yl ]phenyl]methanesulfonamide) 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 - 1 - 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 )methanesulfonamide, calculated as the stoichiometricSulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 2 of 13 equivalent of sulfentrazone in or on the following commodity :

Apple 0.15 A tolerance is currently

established under 40 CFR §180.498(a)(1) for the combined residues of sulfentraz one and its 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; the se established tolerances range from 0.15 ppm (various plant commodities) to 0.40 ppm (peanut meal and Brassica , leafy

greens, subgroup 5B). Tolerances for the combined residues of sulfentrazone and its metabolites HMS and DMS have been established under 40 CFR §180.498(c) in connection with regional registrations; these include tolerances for residues in/on succulent lima bean, succulent cowpea, and wheat grain at 0.15 ppm. 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. The sulfentrazone end - use products (EPs) relevant for this registration request include 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). The petitioner request s the amendment of these EP labels to incorporate a new use on apples . These EPs are proposed for a maximum seasonal rate of 0.375 lb ai/A using ground equipment with a pre - harvest interval (PHI) of 14 days. The nature of the residue in plants is adequatel y understood. Data concerning the metabolism of sulfentrazone following preemergent applications in soy beans and confined rotational crops were submitted in conjunction with the s oy bean petition (PP#4F04407 , D211168 ). The HED Metabolism Committee determined that sulfentrazone and its metabolite HMS are the residues of concern in so yb eans , and that sulfentrazone and its metabolites HMS and DMS (free and conjugated) are the residues of 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 preemergent uses on all crops (D220548, 3/13/96, G. Kramer). Data concerning the metabolism of sulfentrazone following postemergent applications in corn, soy bean, and radish were submitted in conjunction with recent petition s (D389972, 5 / 9 / 12 , G. Kramer) . The metabolism of sulfentrazone was similar to that following preemergent application; no additional major metabolites were identified. HED thus concludes metabolism data are now available to support postemergence applications and that sulfentrazone and its metabolites HMS and DMS (free and conjugated) are the re sidues of concern . 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 . There is an adequate residue anal ytical method for the purposes 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#4F04407). A petition method validation (PMV) was successfull y completed by the Agency ’s Anal ytical Chemistry L aboratory

(ACL). The limit of quantitation (LOQ) and limit of detection (LOD) were determined to be 0.05 ppm and 0.005 - 0.025 ppm, respectivel y. TheSulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 3 of 13 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 FD A MRMs are not suitable as enforcement methods since sulfentrazone residues of concern were not successfull y recovered b y the FDA MRMs. Samples of raw agricultural and processed commodities were anal yz ed for residues of sulfentrazone and its metabolites D MS and HMS using a liquid chromatograph equipped with tandem mass spectrometers (LC/MS/MS) method. The validated LOQ was 0.025 - 0.05 ppm for each anal yt e. These methods are adequate for data collection based on acceptable method validation and concurrent recovery data. The submitted field trial residue data apple are adequate. The field trial data reflect the proposed use patterns; an adequate number of trials were conducted in the appropriate geographic regions; and samples were analyzed for the residue of concern using validated data - collection methods. The storage intervals were also validated. No quantifiable residues were found in apples treated at an exaggerated rate (5 X); therefore, s eparate tolerances are not required for apple processed commo dities. Analy tical standards for sulfentrazone and its metabolites DMS and HMS are currentl y available at the EPA National Pesticide Standards. However, as the existing stocks are depleted, the Repository has requested that the registrant provide additional amounts of sulfentrazone (5 g) and H MS ( 3 g) . N o Codex, Canadian, or Mexican maximum residue limits (MRL s) have been established for sulfentrazone on apples . Therefore, harmonization of MRL s and U.S. tolerances is not an issue at this time. **Regulatory Recommendations and Residue Chemistry Deficiencies** There are no residue chemistry issues that would preclude granting an uncondition al registration for the requested use on apples . The proposed 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:

Apple 0.15 A human - health risk assessment is forthcoming. **Background** The chemical structure and nomenclature of sulfentrazone are presented in Table 1, and the phy sicochemical properties of the technical grade of sulfentrazone are presented in Table 2.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 4 of 13 **Ta ble 1.**  **Sulfentrazone N om**  **enclature** . Chemical structure

Common name Sulfentrazone Com pany 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 fo rmulation (Spartan® 4F Herbicide; EPA Reg. No. 279 - 3220) and 75% DF formulation (Spartan ® Herbicide; EPA Reg. No. 279 - 3189 ) Chemical structure of DMS metabolite

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

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)methanesulfonamide Cl Cl

N H S O 2 C H 3

N N N O C H 3

C H F 2

Cl Cl

N H S O 2 C H 3

N N N O C H F 2

Cl Cl

N H S O 2 CH 3

N N N O C H F 2

O HSulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 5 of 13 **Table 2. Physicochemical Properties of**  **Technical Grade Sulfentrazone**  **.** Parameter Value Reference Melting range 120 - 122 oC DP# 288712, 3/ 6 /03, G. Kramer , G. Reddy, and L. Liu 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 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 . Information regarding rotational crop restrictions is listed in Table 4B. **Table 3. Summary of Proposed End -**  **Use Products .**  Trade Name Reg. No. ai (% of formulation) Formulation

Type Target Crops Target Pests Spartan ® 4F Herbicide 279 - 3220 39.6 (4 lb ai/gal) FlC Rhubarb, Turnips, Sunflower Subgroup 20B, Cowpeas, Wheat (Spring), Tree Nut Crop Group 14, Pistachio, LowGro wing Berry Crop Group 13 - 07, Citrus Fruit Crop Group 10 - 10, Nongrass Animal Feeds Crop Group 18 Broadleaf, grass, and sedge weeds. Spartan ® Herbicide 279 - 3189 75 DF F6285 4F CAL Herbicide 279 - 3370 39.6 (4 lb ai/gal) FlC Rhubarb, Turnips, Sunflower Subgroup 20B, Wheat (Spring), Tree Nut Crop Group 14, Pistachio, Low - Gro wi ng Berry Crop Group 13 - 07, Citrus Fruit Crop Group 10 - 10, Nongrass Animal Feeds Crop Group 18 **Table 4. Summary of Proposed Directions for Use of Sulfentrazone.** App. Timing; Type; and Equip. Formulation (EPA Reg. No.) Application

Rates Max. # App.

per Year Max. Yearly

App. Rate Use Directions and Limitations **Citrus Fruit Crop Group 10 -**  **10 c**  Apply as soil application to orchard floors or as uniform band application directed towards base of the trunk of trees. Ground, impregnated onto dry bulk fertilizer. Spartan 4F Herbicide (279 - 3320) 0.125 - 0.375

lb ai/A Up to 3 0.375 lb ai/A *General use directions: min of 10 GP A. PHI = 14 days. RTI = 60 days. Apply using ground equipment only; do not use airblast sprayer or apply by air. Avoid direct or indirect spray contact with foliage and fruit. F6285 4F CAL Herbicide (279 - 3370) Spartan Herbicide (279 - 3189)Sulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 6 of 13 Conclusions : The use directions are adequate to allow HED an assessment of whether the submitted residue data reflect the maximum residues likely to occur. **860.1300 Nature of the Residue –**  **Plants** The nature of the residue in plants is adequatel y understood. Data concerning the metabolism of sulfentrazone following preemergent applications in soy beans and confined rotational crops were submitted in conjunction with the soy bean petition (PP#4F04407, D211168). The HED Metabolism Committee determined that sulfentrazone and its metabolite HMS are the residues of concern in so yb eans, and that sulfentrazone and its metabolites HMS and DMS (free and conjugated) are the residues of 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 preemergent uses on all crops (D220548, 3/13/96, G. Kramer). Data concerning the metabolism of sulfentrazone following postemergent applications in corn, soy bean, and radish were submitted in conjunction with recent petitions (D389972, 5/9/12, G. Kramer). The metabolism of sulfentrazone was similar to that following preemergent application; no additional major metabolites were identified. HED thus concludes metabolism data are now available to support postemergence applications and that sulfentrazone and its metabolites HMS and DMS (free and conjugated) are the residues of concern. **860.1300 Nature of the Residue –** **Livestock** 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 metabolism proceeds onl y b y oxidation of the 3 - methyl group to form HMS , followed b y further oxidation to form sulfentrazone carbox yl ic acid which is decarbox yl ated to DMS . Sulfentrazone per se and its metabolites HMS and DMS were identified as the residues of concern in meat, milk, poultry , and eggs. **860.1340 Residue Analytical Methods Enforcement**  **M ethod**  A GC anal ytical 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 so yb eans (PP#4F04 4 07). A PMV was successfully completed by

the Agency ’s ACL . The LOQ and LOD were determined to be 0.05 ppm and 0.005 - 0.025 ppm, respectivel y. 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. Kramer, 9/18/98). This method is suitable for enforcement of the tolerances associated with this petition. Data - C ollection M ethods Samples of raw agricultural commodities (RACS) and processed commodities were anal yz ed for residues of sulfentrazone and its metabolites DMS and HMS using a modified L C /MS/MS anal ytical method from study number P - 3171 titled “Magnitude of the Residue of Sulfentrazone in/on Field Corn as a Rotated Crop Following Soybeans Treated with Authority Herbicide: Re -Sulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 7 of 13 An alysis of Selected Trials using Revised Methodology .” Briefl y, homogenized samples were refluxed with acetone:0.25N HCl (3:1, v:v) for 1 hour followed b y filtration and concentration, then refluxed a second time with 1N HCI for 2 hours to free all conjugated anal yt es of concern and to completely convert sulfentrazone - 3 - carboxlic acid (SCA) to DMS. The method quantifies residues of SCA as DMS and calculates SCA residues b y a molecular weight - conversion factor (1.118). SCA is a metabolism intermediate in f ormation of DMS. After filtration, the aqueous solution was brought to volume with water and anal yz ed b y LC /MS/MS. Residues of the metabolites were not determined in parent equivalents. The LOQ, determined as the lowest level of method validation (LLMV) , was 0.025 - 0.05 ppm for all anal yt es in all matrices; the experimental LOD was 0.005 - 0.02 ppm. The data - collection methods described above are adequate based on acceptable method validation and concurrent recovery data. **860.1360 Multiresidue Methods** MRM data for sulfentrazone and HMS were previously submitted and forwarded to FDA (Memo, 2/7/95, G. Kramer). Neither compound was recovered b y 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 using Section 302 (Luke Method; Protocol D) is available. **860.1380 Storage Stability** IR - 4 conducted concurrent storage stability studies with the apple field trials. The results indicate that residues of sulfentrazone, DMS, and HMS are stable under frozen storage conditions in/on apple for up to 743 days (24.4 months) . Samples were stored frozen (<0 °C at the processing facility

and anal ytical laboratory) from harvest/processing to anal ys is for 761 day s (25 months) for apple (RAC), 783 day s (25.8 months) for juice, and 748 days (24.6 months) for wet pomace. Conclusions: The available storage stability d ata for sulfentrazone are adequate to support the storage conditions and durations of samples from the submitted crop field trials and processing studies. There are no storage stability issues and no corrections for storage stability need be applied to th e field trial and processing studies. **860.1480 Meat, Milk, Poultry, and Eggs** HED previousl y determined that, based on the established sulfentrazone tolerances for so ybean and cereal grain commodities and the results of the livestock metabolism studies, conventional feeding studies are not required. Wet apple pomace is the only significant new feedstuff for livestock (ruminants only) . As n o quantifiable residues were found in apples treated at an exaggerated rate (5X) and tolerances are established fo r feed items at higher levels than the recommended tolerance for the combinedSulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 8 of 13 residues of sulfentrazone, DMS, and HMS of 0.15 ppm for apple (e.g., 0.50 ppm for wheat forage ) , the proposed new use on apples is not expected to increase the livestock dietary burdens . **860.1500 Crop Field Trials** DER Reference List 49124501 .der 1 .doc x IR - 4 has submitted field trial data for sulfentrazone on apple. Twelve field trials were conducted in the United States during the 2009 growing season in the North American Free Trade Agreement (NAFTA) Growing Zones 1 (NY; 2 trials), 2 (NJ and NC; 2 trials), 5 (MI ; 2 trials), 9 (CO; 1 trial), 10 (CA; 1 trial), and 11 (ID and WA; 4 trials). Each trial consisted of one untreated plot and one treated plot. At each trial locati on, the treated plot received a single soil broadcast or banded application of Spartan® 4F Herbicide made to each side of the orchard row at 0.360 - 0.393 lb ai/A (1X). Applications were made using ground equipment in spray

volumes of 11 - 40 gal/A without an adjuvant. Samples of mature apples were harvested at a PHI of 13 - 15 day s. In samples harvested at a 13 - to 15 - day PHI following a single soil broadcast or banded application of the 4 lb ai/gal SC formulation at a total seasonal rate of 0.360 - 0.393 lb ai/A, residues of sulfentrazone and metabolites DMS and HMS were each below the L OQ (<0.05 ppm) in/on all samples of apples. Combined residues of sulfentrazone, DMS, and HMS (and per- trial averages) were <0.15 (<0.15) ppm. No residue - decline data were su bmitted; however, these data are not required because residues were non - quantifiable in/on all samples at the earliest harvest time. Conclusions : The submitted residue data are adequate to fulfill data requirements apples . The number and locations of th e crop field trials are in accordance with OPPTS Guideline 860.1500 (Table 5 ). The available data will support the proposed use pattern. **TABLE 5**  **. Trial Numbers and Geographical Locations** . NAFTA Growing Zones Apple Submitted Requested 1 Canada U.S. 1 2 -- 4/3 2 2 2

-- 2/1 5 2 -- 3/2 9 1 -- 1/1 10 1 -- 1/1 11 4 -- 5/4 Total 12 16/12 1 As per OCSPP 860.1500, Tables 1 and 5 for apple. The second number reflects a 25% reduction in the number of field trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application results in no quantifiable residues. 2 The Zone 2 trial conducted in NJ was located near the border of Zone 1. As all residues were <LOQ, the recommended tolerance for the combined residues of sulfentrazone, DMS, and HMS is 0.15 ppm for apple .Sulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 9 of 13 **860.1520 Processed Food and Feed**  DER Reference List 49124501 .der2 .doc x IR - 4 has submitted a processing study with sulfentrazone on apple. In one apple trial conducted in NY during the 2009 growing season, a treated plot received a single soil - banded application of Spartan ® 4F Herbicide made to each side of the orchard row at a rate of 1.919 lb ai/A (~5X). Applications were made using ground equipment in spray volumes of 25.6 gal/A without an adjuvant. Samples of mature apples were harvested at a PHI of 15 day s and proces sed into pasteurized juice and wet pomace using simulated commercial procedures. Processing was conducted b y A.C.D.S. Research, Inc. (North Rose, NY). Adequate descriptions were provided of the processing procedures, including material balance summaries. In samples harvested at a 15 - day PHI following a single soil - banded application of the 4 lb ai/gal SC formulation at a total seasonal rates of 1.919 lb ai/A, residues of sulfentrazone and metabolites DMS and HMS were each below the LOQ (<0.05 ppm) in/on all samples of apples (RAC), juice, and wet pomace. Processing factors could not be calculated because residues were below the LOQ in both the RAC and processed commodities. Conclusions : These data indicate that significant concentration of sulfentrazon e residues are unlikely to occur in the processed fractions of apples ; therefore, separate tolerances are not required for apple processed commodities. **860.1650 Submittal of Analytical Reference Standards** Analy tical standards for s ulfentrazone ( expiration date 7/1/15 ) and its metabolites DMS (expiration date 8/1/17) and HMS (expiration date 8/31/18) are currentl y available at the EPA National Pesticide Standards Repository (personal communication with Theresa Cole , 4 /2 1 / 1 4 ) . However, as the existing stocks are depleted, the Repository has requested that the registrant provide additional amounts of sulfentrazone (5 g) and HMS (3 g). They should be sent to the Analy tical Chemistry

L ab, which is located at Fort Meade , to the att ention of either Theresa Cole or Thuy Nygen at the following address: USEPA National Pesticide Standards Repository /Anal ytical Chemistry

Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755 - 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** As apple trees are not rotated, rotational crop issues are not relevant to the current petition.Sulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 10 of 13 **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). Sul fentrazone tolerances are currentl y established 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 “combined residues of the free and conjugated forms of sulfentrazone, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of sulfentrazone ( N - [2,4 - dichloro - 5 - [4 - (difluoromethyl ) - 4,5 - dihydro - 3 - methyl - 5 - oxo - 1 H - 1,2,4 - triazol - 1 - yl ]phenyl]methanesulfonamide) 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 - 1 - 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 )methanesulfonamide, calculated as the stoichiometric equivalent of sul fentrazone in or on the following commodities.” N o Codex, Canadian, or Mexican MRL s have been established for sulfentrazone on the subject crop . Therefore, harmonization of MRL s and U.S. tolerances is not an issue at this time . An International Residue Li mit s form is appended to this Summary Document. A tolerance summary

for sulfentrazone is presented in Table 6 . **Table 6**  **. Toler ance Summary for Sulfentrazone.**  Commodity Proposed Tolerance (ppm) HED Recommended Tolerance (ppm) Correct Commodity

Definition/Comments **Establish under 40 CFR §180.498(a)(2):** Apple 0.15 0.15 **References** DP#: 389972 Subject: Sulfentrazone. Section 3 Registration Request to Add New Uses on Rhubarb,

Turnips, Sunflower Subgroup 20B, Succulent Cowpea, Lima Bean, Vegetable Soy bean, Wheat, Citrus Fruit Crop Group 10 - 10, Low - Growing Berry Crop Group 13 - 07, Tree Nut Crop Group 14, Clover, Alfalfa, and Pistachios. Summary of Anal ytical Chemistry

and Residue Data. From: G. Kramer To: K. Montague/B. Madden Dated: 5/9 / 12 MRID(s): 483973 - 02 thru - 09, 485148 - 01 thru - 03 DP#: 288712 Subject: Sulfentrazone

– Briefing Memorandum for Meeting of Metabolism Assessment

Review CommitteeSulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 11 of 13 From: G. Kramer To: Y. Donovan Dated: 3/6/03 MRID(s): None 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 Anal ytical Chemistry

and Residue Data. From: G. Kramer To: D. Morgan/J. Mi ller 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 Anal yt ical 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 So ybeans. Results

of Petition Method Validation (PMV). From: G. Kramer To: S. Robbins/K. Boyle Date d: 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 Metabolism 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 Testing of sulfentrazone and 3 - hydroxy methyl sulfentrazone. From: G. Kramer To: H. Hundley Dated: 2/7/95Sulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 12 of 13 MRID(s): 43345416 **Attachments:** Appendix I - International Residue Limit Sheet.

**DOCUMENT TRACKING** RDI : RAB1 Chemistry

Team: 0 4 /23 /20 1 4 Petition # : 3E8202 DP# s : 415626 PC Code: 129081 Template Version September 2005Sulfentrazone Summary of Analytical Chemistry and Residue Data DP# 415626

Page 13 of 13 

### Appendix I. **International Tolerances** International Residue Limits **Sulfentrazone** 

### ( 129081 ; 4/1 5 /201 4 ) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : U.S. Canada Mexico 2 Codex 40 CFR 180.498: (2) sum of sulfentrazone (N - [2,4 - dichloro - 5 - [4 - (difluoromethyl) - 4,5 - dihydro - 3 - methyl - 5 - oxo - 1 H - 1,2,4 - triazol 1 - yl]phenyl]methanesulfonamide) and its metabolites HMS (N

- (2,4 - dichloro - 5 - (4 - (difluoromethyl) - 4,5 - dihydro - 3 - hydroxymethyl - 5 - oxo - 1 H - 1,2,4 - triazol - 1 - yl)phenyl)methanesulfonamide) and DMS (N - (2,4 - dichloro - 5 - (4 - (difluoromethyl) - 4,5 - dihydro - 5 - oxo - 1 H1,2,4 - triazol - 1 - yl)phenyl)methanesulfonamide, calculated as the stoi chiometric equivalent of sulfentrazone Plants (except dry soybeans): N - [2,4 - dichloro - 5 - [4 - (difluoromethyl) - 4,5 - dihydro - 3 - methyl - 5 - oxo - 1 H - 1,2,4 - triazol - 1 - yl] -phenyl]methanesulfonamide, including the metabolites N - [2,4 - dichloro - 5 - [4 - (difluoromethyl) - 4,5 - dihydro - 3 - hydroxymethyl - 5 - oxo 1 H - 1,2,4 - triazol - 1 - yl]phenyl]methanesulfonamide and N - [2,4 - dichloro - 5 - 4 - (difluoromethyl) - 4,5 - dihydro - 5 - oxo - 1 H - 1,2,4 - triazol - 1 - yl]phenyl]methanesulfonamide None

Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) U.S. Canada Mexico 2 Codex Apple 0.15

Com pleted: M. Negussie; 04/16/2014 1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and not those proposed by the applicant. 2 Mexico adopts U.S. tolerances and/or Codex MRLs for its export purposes.