Page 1 of 30 UNITED STA

TES ENVIRONMENTA L PROTECTION AGENCY WASHINGTON, D.C. 20460OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION MEMORANDUM Date : October 12 , 2010 SUBJECT: Fomesafen Sodium . Petition for the Establishment of Toleranc es and Registration

of New Uses on Pepper and Potato , and Response to Data Gaps for Conditional Registration based on Submission of a Confined Rotational Crop Metabolism Study . Summary

of Analy tical Chemistry and Residue Data . PC Code: 123802 DP Barc ode s : D373544 and D382067 Decision No.: 426814 Registration No. : 100 - 993 Petition No s : 9F7563 (potato) , 9F7667 (pepper) Regulatory Action: Amended Section 3 Risk Assessment Type: NA Case No.: NA T XR No.: NA CAS No.: 72178 - 02 - 0 MRID No.: See MRID Summary Table 40 CFR: § 180. 433 FROM: Alexandra L aMay , Biologist

Christine Olinger, Chemist Risk Assessment Branch VI I Health Effects Division (7509P) THROUGH: Michael S. Metzger, Chief

Risk Assessment Branch VI I H ealth Effects Division (7509P) TO: Michael Walsh , PM Team 23

Herbicide Branch Registration Division (7505P) MRID Sum ma ry Table MRID No. Study Type Com me nts 4 7941402 860.1500 Pepper Crop Field Trials New DER; 47941402.de1 .doc

860.1380 Pepper Storage Stability Study New DER; 47941402.de2.doc 47937602 860.1850 Confined Rotation al Crop Study New DER; 47937602.de r .docFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 2 of 30 Executive Summary Fomesafen sodium is a contact broadleaf herbicide in the diphenyl ether chemical class. The herbicide acts through inhibition of the enzy me protoporphy

rinogen oxidase (PPO) in plants. The active ingredient was originally registered on 09/11/ 1987 by Zeneca Ag Products and was transferred to Sy

ngenta Crop Protection, Inc . on 02/23/2001. Fomesafen is currently registered for use on the crops cotton, dry beans, snap beans, and soy beans. It is applied to treat various broadleaf weeds, annual grasses, perennial weeds and sedges. Sy ngenta has proposed, in PP#9F7563 and PP# 9F7 667 , the establishment of permanent tolerances for residues of fomesafen in/on the following raw agricultural commodities: Potato ................................ ................................ ................................ ....... 0.025 ppm Pepper ................................ ................................ ................................ ...... 0.025 ppm Insupport of the proposed tolerances and new crop uses , Sy ngenta has submitted a magnitude of the residue study

on pepper and a confined rotational crop metabolism study . Sy ngenta has previously

submitted a magnitude of the residue study on potatoes (also described in DP barcode D365199 and D3661 1 6 , 1/21/2010, C. Olinger) . This Summary Document addresses the adequacy of the submitted residue chemistry data in support of the proposed new uses on peppers as well as the adequacy

of the submitted residue chemistry of the confined rotation crop metabolism study . On peppers , Reflex® Herbicide is propo sed for one broadcast preplant non - incorporated preemergence application up to 7 days prior to transplanting pepper seedlings at a maximum rate of 0.375 lb ae/A and a 60 - day preharvest interval ( PHI ) . On potatoes, Reflex® Herbicide is proposed for one bro adcast preemergence application after planting but before potato emergence at a maximum rate of 0.25 lb ae/A and a 70 - day PHI . HED generally

recommends that three metabolism studies on diverse crops when a pesticide is to be used on several different comm odities. Itwas previously concluded that the three previouslysubmitted metabolism studies on tomatoes, soy beans and cotton were not sufficiently diverse to define the natur e of the residue in all crops. S ince no data on a root crop had been provided th at can be translated to the p roposed use on potatoes , a potato metabolism study , in which both the root and tops/foliage were analy zed, was required to support the proposed use on potatoes (D365199 and D366116 , 1/21/2010, C. Olinger) . Sy ngenta has submitt ed a confined rotational crop metabolism study

as part of the current submission, which HED has determined is adequate and is acceptable to use to determine the nature of the residue in potato. The residue of concern in plants is fomesafen . The re are no livestock feedstuffs associated with the proposed use on peppers ( PP# 9F7667 ) . The only livestock feedstuffs associated with the proposed uses in PP#9F7563 are potato culls and processed waste. The nature of the residue in ruminants is adequately understoo d. At this time no tolerances have been established on any livestock commodity

in association with the existing uses of fomesafen. There is no reasonable expectation of finite residues in livestock. Therefore, no livestock feeding studies are required t o support the proposed/registered uses of fomesafenFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 3 of 30 sodium. Sy

ngenta should note that if additional uses are proposed in the future which result in an increase in the dietary

burden s , livestock feeding studies may be required. Adequate residue analy

tica l methods are available for the purpose of tolerance enforcement. Sy ngenta s ubmitted a new high performance liquid chromatography method with tandem mass spectrometry

detection ( LC /MS/MS ) method (GRM045.01A) as an enforcement method . The method uses extr action procedures similar to previous methods, SPE cleanup procedures, and the final determination step by L C/MS/MS for analy sis of fomesafen residues. The validated limit of quantitation (L OQ) of the method is 0.02 ppm. Method GRM045.01A was adequately validated at fortification levels of 0.02 ppm and 0.2 ppm in snap beans, pinto beans (dry bean), corn oil, cotton, undelinted seed and gin by products, and soy

bean forage, hay , and aspirated grain fractions. Methods for the determination of fomesafen resid ues of concern in livestock commodities are not required at this time. The requirements for multiresidue method testing data for fomesafen are fulfilled. FDA multiresidue methods are not suitable for determining residues of fomesafen. Samples of raw and processed commodities of potatoes, which were collected from the magnitude of the residue studies, were analy zed for residues of fomesafen using a LC/MS/MS based on a liquid chromatography with ultraviolet detection ( HPL C/UV ) method (GAM - RM 001/86). The method was adequately validated during concurrent analysis of samples. The lowest level of method validation (LLM V) was 0.025 ppm. Samples of raw commodities of pepper, which were collected from the magnitude of the residue studies, were analy zed for residues of fomesafen using a H PL C /MS/MS method (TMR0626B)

. Th e method was adequately validated during concurrent analysis of samples. The lowest level of method validation (LLM V) was 0.025 ppm. Analy tical standards for fomesafen are currently availabl e in the EPA National Pesticide Standards Repository . Adequate storage stability data are available to support the storage conditions and durations of samples collected from the magnitude of the residue studies on potato and pepper . The submitted field trial data for fomesafen on peppers and potatoes are acceptable and support the proposed uses. An adequate number of trials were conducted in the appropriate geographic regions at ~1x the maximum proposed rate using Reflex® Herbicide, and the appropriate samples were collected from each test around the proposed PHI . All treated samples bore residues below the LLM V (<0.025 ppm). Based on these data, HED recommends a tolerance of 0.025 ppm for residues of fomesafen in/on peppers and potatoes . The results of submitted potato processing studies show that residues of fomesafen were each below the LLM V (<0.025 ppm) in/on the respective RACs following application of Reflex® Herbicide at 1x. Since the studies involved processing of RACs bearing nonquantifiable residues, no measurable processing factors can be calculated. Although, the Agency would have preferred the use of exaggerated rates in the conduct of the processing studies to y ield RACs with quantifiable residues , HED will not require additional proces sing data at this time .Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 4 of 30 Sy ngenta has submitted a new confined rotational crop study reflecting separate application of CP - and NP - label fomesafen at the maximum seasonal application rate to rotatable crops , incl uding wheat, soy

bean, potato, spinach, radis h and carrot . This has been completed and reviewed by

the Agency , and it has been determined that the nature of the residue in rotational crops is adequately

understood. This confined rotational crop data satisfies the data gap of the conditional registr ations of previous assessment (D365199 and D366116). There is now data to support rotation to other crops beyond those commodities that are currently registere d and proposed as primary crops. All plant back intervals ( PBI s ) for rotational crops on the draft label are acceptable , including a 4 month PB I for wheat (and similar commodities), a 10 month PBI for corn, peanuts, peas, rice, and seed corn and an 18 month PBIfor alfalfa, sunflowers, sugar beets and sorghum . No Codex, Canadian, or Mexican MRL s have been established for residues of fomesafen in/on potato or pepper ; therefore, there are no issues with international harmonization raised by this action . Canadian MRL s have been established for residues of fomesafen in/on dry beans, lima beans, snap beans, and soy beans at 0.05 ppm, and a Mexican MRL of 0.05 mg/kg has been established for residues of fomesafen in/on soy beans. Regulatory Recommendations HED has examined the residue chemistry database for fomesafen sodium. T h e deficiency pertaining to directions for use the submission of a confined rotational crop study has been resolved; there are no residue chemistry issues that would preclude granting the petitioner’s request to amend the Reflex® Herbicide label for the pur pose of add ing the requested use on potatoes and peppers . HED recommends a registration for this herbicide on the crops requested and/or the revision of 40 CFR §180.433 for the establishment of tolerances for residues of fomesafen as follows: Potato ................................ ................................ ................................ ....... 0.02 5 ppm Pepper , bell ................................ ................................ ............................. 0.025 ppm Pepper, non - bell ................................ ................................ ...................... 0.025 ppm Also, the data gaps pertaining to the conditional registration on tomatoes , dry bean, snap bean, and cotton has been resolved based on submission of adequate confined rotational crop metabolism dat a . The registrant’s most recent Reflex® Herbicide label reflects regional use of fomesafen on peppers . H owever, the residue chemistry data submitted in support of this action are of sufficient geographic representation to support full U.S. registration; therefore, HED recommends that these tolerances be listed in the general section of 40 CFR § 180.433. Tolerances for fomesafen residues are listed in 40 CFR §180.433. Currently , the single established tolerance is expressed in terms of “sodium salt of fo mesafen, 5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] -N - (methylsulfonyl) - 2 - nitrobenzamide.” HED has determined that the residue of concern for tolerance expression is fomesafen. Therefore, the established toleranceFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 5 of 30 expression should be revised to be expressed in terms of fomesafen, by removing the phrase “sodium salt of” from 40 CFR §180.433(a). Note to PM: According to HED’s Interim Guidance on Tolerance Expressions (5/27/09, S. Knizner), the tolerance expression for fomesafen should be revised to state: “T olerances are established for residues of fomesafen, including i t s 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

fomesafen [5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] -N - (methylsulfonyl) - 2 - nitrobenzamide].” The current tolerances listed in 40 CFR § 180.433 for fomesafen in soy beans, dry

beans, and snap (succulent) beans are 0.05 ppm. HED continues to recommend for the reduction of the followin g tolerances, as described in a previous memo (D. Davis, DP No. D325801, 4/25/06): dry beans and snap (succulent) beans should be reduced to 0.025 ppm and the tolerance on soy beans should be reduced to 0.02 ppm. Note that the lower tolerance values were used in the dietary risk assessment. A human health risk assessment is forthcoming. Residue Chemistry Deficiencies Deficiencies - Tomato Petition ( 9F7563) All data gaps previously

identified by

HED ( DP# 365199 and 366116, 1/21/2010, C. Olinger) as a co ndition of registration under the petitions cited above have now been adequately fulfilled . The data gap of confined accumulation in crops identified in HED (DP# 365199 and 366116, 1/21/2010, C. Olinger) as a condition of registration for the use on tomat oes has now been adequately

fulfilled. There is now data to support rotation to other crops beyond those commodities currently registered and prim ary

crops. The data supports a 4 month rotational interval to small grains; a 10 month rotational interval to corn, peanuts, peas, rice and seed corn ; and an 18 month rotational interval to alfalfa, sunflowers, sugar beets, and sorghum .Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 6 of 30 Remaining Deficiencies

– PP#s 1E6228 (Dry Bean), 9F5068 (Cotton), and 6E4653 (Snap Bean) The data gap of the requirement for confined rotational crop data previously identified by HED ( DP# 365199 and 366116, 1/21/2010, C. Olinger) as a condition of registration under the petitions cited above have now been adequately fulfilled . There still remains the deficiency pertaini ng to storage stability listed below. 860.1380 Storage Stability

· The registrant intends to submit a final storage stability report, including analy ses at 18 and 24 months. When this study is submitted the registrant should ensure that the dates doc umented in the report should reflect the actual storage intervals, and not the proposed intervals, as there was some discrepancy in the interim report. Background The chemical name and structure of fomesafen sodium and fomesafen are listed below in Table 1. The phy sicochemical properties of fomesafen are listed in Table 2; data pertaining to the phy sicochemical properties of fomesafen sodium are not available. T able 1. Test Compound Nom enclature. Compound F 3 C

Cl O N O 2

O N S C H 3 O O Na+

Common name Fomesafen Sodium Company expe rimental name Not provided. IUPAC name 5 - (2 - chloro - α,α,α - trifluoro - p - tolyloxy) - N - methylsulfonyl - 2 - nitrobenzamide, sodium salt CAS name 5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] - N - (methylsulfonyl) - 2 - nitro - benzamide, sodium salt CAS registry number 108731 - 70 - 0 Compound F 3 C

Cl O N O 2

O N H S C H 3 O O

Common name Fomesafen Company experimental name Not provided. IUPAC name 5 - (2 - chloro - α,α,α - trifluoro - p - tolyloxy) - N - methylsulfonyl - 2 - nitrobenzamide CAS name 5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] - N - (methylsulfonyl) - 2 - nitrobenzamide CAS registry number 72178 - 02 - 0 End - use pro duct (EP) Reflex® Herbicide, 2 lb ae/gal SL ; EPA Reg . No . 100 - 993Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 7 of 30 T able 2. P hysicochemical Properties of Fom esafen. Parameter Value Reference Melting point/range 220 - 221  C HED Memo, 9/3/82, W. Anthony pH 8.2 (94% TGAI) CSF (EPA Reg. No. 100 - 1017; 1 0/13/00) Density 1.28 g/cm3 at 20  C HED Memo, 9/10/86, C. Trichilo Water solubility at 25 °C 600 g/L at pH 7 <10 ppm at pH 1 - 2 50 mg/L HED Memo, 9/3/82, W. Anthony HED Memo, 9/10/86, C. Trichilo Solvent solubility g/L Acetone 300 Cyclohexanone 150 Methanol 25 Hexane 0.5 Xylene 1.9 HED Memo, 9/10/86, C. Trichilo

Vapor pressure <7.5 x 10 - 7 mm Hg at 50  C The Pesticide Manual 1 Dissociation constant, pK a 2.7 at 20  C Octanol/water partition coefficient, Log(KOW) Log KOW = 2.9 at pH 1 UV/visible absorption spectrum Not available 1 The Pesticide Manual, A World Compendium, The British Crop Protecti on Council ( toxnet.nlm.nih.gov). 860.1200 Directions for Use The end - use product relevant to the pepper petition ( PP#9F7667 ) and potato petition ( PP#9F7563 ) is Reflex® Herbicide (EPA Reg. No. 100 - 993), a soluble concentrate liquid (SL) formulation conta ining 22.8% sodium salt of fomesafen as the active ingredient (equivalent to 2 lb ae/gal of fomesafen). Reflex® is a selective herbicide which may be applied preplant surface, preemergence, and/or postemergence for control or partial control of broadleaf weeds, grasses, and sedges in registered crops cotton, dry beans, snap beans, and soy beans. In support of the proposed use on peppers , the petitioner submitted a draft label for Reflex® Herbicide dated 4 /22 /20 10 . A s ummary

of the proposed use directions for potatoes and peppers is presented in Table 3 A . Table 3A . Summary of Proposed Use Directions of Reflex® Herbicide (EPA Reg. No. 100 - 993 ; 2 lb ae/gal)

on Potato es and Peppers . Applic. Timing, Type, and Equip. Applic. Rate (lb a e /A) Max. No.

Applic. p er Season Max.

Seasonal Applic. Rate (lb a e /A) PHI

(days) Use Directions and LimitationsFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 8 of 30 Table 3A . Summary of Proposed Use Directions of Reflex® Herbicide (EPA Reg. No. 100 - 993 ; 2 lb ae/gal)

on Potato es and Peppers . Applic. Timing, Type, and Equip. Applic. Rate (lb a e /A) Max. No.

Applic. p er Season Max.

Seasonal Applic. Rate (lb a e /A) PHI

(days) Use Directions and Limitations Peppers (Transplanted ) Broadcast pre plant non incorporated pre emergence application up to 7 days prior to transplanting peppers Ground/Aerial/Center pivot irrigation 0.25 - 0.375 1 0.375 60 Refer to Syngenta’s Regional Use Map for Reflex® 1 ( summarized in the ‘General Use Directions’ below) for determination of maximum use rate that may be applied in each geographic region. Do not apply to any field in Regions 2, 3, 4, or 5 more than once every two years. Potato

Broadcast preemergence application after planting but before potato emergence Ground/Aerial/Center pivot irrigation 0.25 1 0.25 70 Refer to Syngenta’s Regional Use Map for Reflex® 1 (summarized in the ‘Genera l Use Directions’ below) for determination of maximum use rate that may be applied in each geographic region. Do not apply to any field in Regions 2, 3, 4, or 5 more than once every two years. Do not apply to sweet potatoes or yams. Do not apply as a pr eplant incorporated application as crop injury may occur. Do not apply to emerged potato plants or severe crop injury will occur. 1 The draft label specifies five use regions with specific seasonal maximum application rates. The rates range with the la bel use Region 1 having the highest seasonal application rate reflects application at 0.375 lb ae/A each year and label use Region 5 with the lowest seasonal application rate reflects application of up to 0.1875 lb ae/A in alternate years . Details of the seasonal maximums for all label use Regions are presented below under “General Use Directions”. General U se D irections Sy ngenta’s regional use map for Reflex® : The draft label specifies that product may only be use d in the eastern half of the U.S . Sy ng enta’s r egional u se m ap for Reflex® is subdivided into the following five regions: Region 1: Reflex® may

be applied at a maximum of 0.375 lb ae/A per year in Region 1 per year which includes the following states or portion of states: AL , AR, FL, GA, LA, MS, MO (counties of Bollinger, Butler, Cape Girardeu, Dunklin, Madison, Mississippi, New Madri d , Pemiscot, Perry , Ripley , Scott , Stoddard, and Way ne), NC, OK (East of U.S. Highway 75 and East of Indian Nation Parkway ), SC, TN, and TX (includes area East o f U.S. Highway 77 to State Road 239 including all of Calhoun County ). Region 2: Reflex® may

be applied at a maximum of 0.375 lb ae/A in alternate years in Region 2 which includes the following states or portion of states: DE, KY, MD, VA, WV, and South o fFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 9 of 30 Interstate 70 in the following states: IL, I N, and OH and all areas South of the Interstate 80 to the intersection of U.S. Highway 15 and East of U.S. Highway 15 and U.S. Highway

522 in PA. Region 3: Reflex® may

be applied at a maximum of 0.313 lb ae/A in alternate years in Region 3 which includes the following states or portion of states: CT, IA, ME, MA, M O (all counties except those listed in Region 1), NH, NJ, NY, PA (all areas except those listed in Region 2), RI , VT, and WI(South of U.S. Highway 18 between Prairie Du Chien and Madison, and South of Interstate 94 between Madison and Milwaukee), and North of Interstate 70 in the following states: I N, IL, and OH. Region 4: Reflex® may

be applied at a maximum of 0.25 lb ae/A in alternate years in Region 4 which includes the following states or portion of states: KS ( all counties East of or intersected by U.S. Highway

281), MI(Southern Peninsula), MN (all areas South of Interstate 94), NE (all counties East of or intersected by U.S. Highway

281), and WI(all areas, except those in Region 3, South of Interstate 94 from MN state line to Eau Claire and South of U.S. Highway from Eau Claire to Green Bay

plus Barron, Chippewa, Clark, Door, Dunn, Eau Claire, Kewaunee, Marathon, Menominee, Oconto, Polk, Shawano, and St. Croix counties. The following counties are excluded: Adams, Marquette, Portage, Waupaca, Waushara, and Wood). ND (all areas East of Interstate 29 from Fargo South to the S D state line). SD (all areas East of Interstate 29 from the ND s tate line to Watertown, all areas East of Highway 81 from Watertown to Madison and all areas East and South of State Road 34 and U.S. Highway 281 to the NE state line. Region 5: Reflex® may

be applied at a maximum of 0.1875 lb ae/A in alternate years in Region 5 which includes the following states or portion of states: ND (all areas East of the U.S. Highway 281 except those areas in Region 4), SD (all areas East of the U.S. Highway 281 except those areas in Region 4), and MN (all areas South of the U.S. Highway 2 except those areas in Region 4). Spray additives : The draft label specifies that spray additives cleared for use on growing crops under 40 CFR §180.1001 may be used in the spray

mixture. A nonionic surfactant (NI S), crop oil concentrates (COC) , or other adjuvant s may be used for postemergence applications only . Since the proposed uses on potatoes and peppers are either preemergence or pretransplant, the use of surfactants is ty

pically not needed when Reflex® is applied to these crops , as the l abel states adjuvants are not needed for preplant surface or preemergence applications unless Reflex® is being used in a burndown on emerged weeds. Application equipment : Ground applications are to be made in a minimum of 10 gal/A, and aerial applicati ons are to be made in a minimum of 5 gal/A. Applications are not to be made through any

ty pe of irrigation equipment except center pivot sy stems. Reflex® alone or in tank mixture with other herbicides on the label, which are registered for center pivot a pplication, may be applied in irrigation water preemergence (after planting but before weeds or crop emerge) at label - recommended rates. Tank mixtures with other products registered for use on potatoes and peppers : The draft label provides mixing procedures for tank mixes but does not specify specific tank mix partners for potatoes and peppers . The use directions state that, for tank mix combinations, the recommendations, restrictions, and limitations for all products must be followed and that theFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 10 of 30 most r estrictive labeling is to apply . For preemergence application in potatoes, Reflex® may be tank mixed with other pesticide products registered for use in this way and timing in potatoes. For preplant non - incorporated preemergence applications prior to transplanting peppers , Reflex® may also be tank mixed with other pesticide products registered for use in this way and timing in peppers . Rotational crop plantback intervals : The draft label specifies that the rotational crops listed in Table 3B may

be pl anted after applying Reflex® at recommended rates. Table 3B. Rotational Crop Plantback Intervals Listed on the Reflex® Herbicide. Crop To Be Planted Minimum Rotation Interval ( Days or Months After Last Reflex®

Application) Cotton, dry beans, peppers, p otatoes, snap bean, soybeans, and transplanted tomatoes 0 Small grains such as wheat, barley, and rye 4 mo nths Corn 1 , peanuts, peas, rice, seed corn 10 mo nths To avoid crop injury, do not plant alfalfa, sunflow ers, sugar beet, sorghum 2 , or any crop wi thin 18 mo nths Do not graze rotated small grain crops or harvest forage or straw for livestock. 1 Use a 12 month minimum rotation interval for popcorn in the states of OH, KY, IL, IN, IA, and Region 4 when applied at rates of 0.25 lb ae/A or more. Use 18 mo nth minimum rotation for sweet corn in the states of CT, ME, MA, NH, NY, RI, VT, and Region 5. 2 Sorghum may be planted back after 10 months in Region 1. Conclusions . The available draft label for Reflex® Herbicide is adequate to allow evaluation of residue data relative to the proposed use on potatoes and peppers . The available draft label and available d ata are adequate to evaluate rotation to other crops beyond those commodities that are currently registered and proposed as primary crops . 860.1 300 Nature of the Residue - Plants DER Reference: 47473901.der.doc (tomato) DER Reference: 44754706.der.w pd (cotton) DER Reference: 45313001.der.w pd (soybean) Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis Residue Chemistry Memo DP#365199 and 366 116 , 1/21/2010, C. Olinger Currently adequate tomato, soy

bean, and cotton metabolism studies are available for fomesafen , but no metabolism studies are available for a root crop . Ina meeting with HED in 2008, the registrant proposed substituting the res ults of a confined rotational crop study for the root/tuber metabolism study , since the use is early season, is used in manner similar to the applications employed in a rotational study , and the use is not likely to result in detectable residues. However, the confined study had not been submitted when HED had reviewed the petition on potatoes ( DP#365199 and 366116, 1/21/2010, C. Olinger). Sy ngenta has since submitted a confined rotational crop metabolism study for the rotational crops of wheat, soy bean, p otato, spinach, radish, and carrot (see section 860.1850) . No new metabolites of concern relevant to root/tuber vegetables were identified in the study . HED has concluded this study is adequate toFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 11 of 30 support the tolerance in/on potatoes. The residue of con cern in/on potatoes and peppers is fomesafen. 860.1300 Nature of the Residue - Livestock MRID 00110508 (PP#2G2745, 1/28/83, A. Rathman, and PP#4F2997, 9/25/94, A. Smith) MRID 00135635 (PP#4F2997, 9/25/84, A. Smith) Residue C hemistry Memo DP# 325801, 4/25 /06, D. Davis Residue Chemistry Memo DP#365199 and 366116 , 1/21/2010, C. Olinger Sy ngenta submitted a goat metabolism study in conjunction with the temporary tolerance petition for soy beans (PP#2G2745). A single goat was dosed with [nitrophenyl 14 C]fomes afen at 0.1 ppm in the diet for 7 day s; the goat was sacrificed 16 hours after the final dose. The dosing level corresponds to ~2x and 5x the maximum theoretical dietary burden s to beef and dairy cattle , respectively . TRR reached a maximum in milk of 0.0 008 ppm on Day 3. TRR were 0.003 ppm in liver, 0.004 ppm in kidney , <0.003 ppm in meat, and <0.005 ppm in fat. Approximately 70% of the dosed radioactivity was excreted. No residue characterization was conducted because of low radioactivity

levels. A goat metabolism study

was reviewed in conjunction with the soy bean permanent tolerance petition (PP#4F2997). A single goat was dosed with [nitrophenyl 14 C]fomesafen at 10.3 ppm in the diet for 3 consecutive days; the goat was sacrificed 4 hours after the final dose. The dosing level corresponds to ~ 184 x and 468 x the maximum theoretical dietary burdens to beef and dairy cattle, respectively . TRR were 0.20 ppm in liver, 0.28 ppm in kidney , 0.009 ppm in meat, 0.006 ppm in fat, and 0.014 ppm in milk. Appro ximately 47% of the dosed radioactivity was excreted. Fomesafen was not found in any milk, tissue, or excreta sample. The identified metabolites were 5 - (2 - chloro - α,α,α - trifluoro - p - tolyloxy ) - N - methylsulfonylanthranilamide (compound XV) and 5 - (2 - chloro - α,α ,α - trifluoro - p - tolyloxy ) anthranilic acid (compound V). Compound XV was found at 10% TRR in liver and 20.9% TRR in kidney , and compound V was found at 34.5% TRR in liver and 33.9% TRR in kidney . Conclusions . The available livestock metabolism data are adequate to satisfy data requirements. The significant components of the animal residues are fomesafen and its metabolites 5 - (2 - chloro α,α,α - trifluoro - p - tolyloxy ) anthranilic acid (compound V) and 5 - (2 - chloro - α,α,α - trifluoro - p tolyloxy ) - N - methylsulfonylanthranilamide (compound XV). Based on the residue levels in goat matrices following dosing at to ~ 184 x and 468 x the maximum theoretical dietary burdens to beef and dairy cattle, respectively , HED concludes that the proposed/registered uses of fomesafen o n cotton, dry and snap beans, soy

beans , potatoes, peppers and tomatoes result in a 40 CFR §180.6(a)(3) situation for livestock commodities; i.e., there is no reasonable expectation of finite residues in livestock commodities. T here are no poultry and swin e feedstuffs associated with the proposed uses.Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 12 of 30 860.1340 Residue Analytical Methods MRIDs 47761903 and 47761904 ( Enforcement method GRM045.01A; DP# 365199 and 366116, 1/21/2010, C. Olinger) Plant commodities Enforcement methods Sy ngenta Crop Protectio n has previously submitted descriptions and validation data for the enforcement method, Method GRM045.01A, which is entitled “Fomesafen Analy tical Method for the Determination of Residues of Fomesafen in Crop Commodities by L C - MS/MS.” This high performanc e liquid chromatography with tandem mass spectrometry detection (L C/MS/MS) method is based on previously submitted gas chromatography with nitrogen phosphorus detection (GC/NPD) methods (refer to DP# 325801, D. Davis, 4/25/06) developed by Zeneca AG. This method is the updated version for previous Zeneca AG data - gathering methods (TMR08055B, TMR0879B, TMR0800B, and TMR0881B). Method GRM045.01A uses extraction procedures modified from the previous GC/NPD methods. Inthe revised method, fomesafen residue s are extracted with 1% hydrochloric acid in acetonitrile . An aliquot is subjected to an SPE cleanup and analy zed using L C/MS/MS. A second ion transition may be monitored for confirmation. The validated LOQ is 0.02 ppm for fomesafen in each matrix. Rep resentative spectra and linearity data were submitted demonstrating adequate sensitivity . Method GRM045.01A has been adequately validated at fortification levels of 0.02 ppm and 0.2 ppm in snap beans, pinto beans (dry bean), corn oil, cotton, undelinted s eed and gin by products, and soy

bean forage , hay , and aspirated grain fractions . This method is adequate for enforcement purposes. Data - collection methods Samples of raw and processed commo dities of potatoes , which were collected from the magnitude of th e residue study , were analy zed for residues of fomesafen using a high performance liquid chromatography method with tandem mass spectrometry detection based on an HPL C/UV method (GAM - RM - 001/86). The method was adequately validated during concurrent analy s is of samples. The lowest level of method of validation (LLM V) was 0.025 ppm for each matrix. Samples of raw pepper, which were collected from the magnitude of the residue study, were analy zed for residues of fomesafen using an ultra performance liquid chromatography method with quadrupole mass spectrometry detection (TMR0626B) based on a GC/NPD method . This method is similar to the enforcement method; this method has a similar extraction method (fomesafen residues are extracted with 1% hydrochloric aci d in acetonitrile ), no SPE cleanup step , a similar analy sis method (done by HPL C /MS/MS), and a different confirmation ion . The method validation percent recovery ranged from 83 - 118%, which is within 70 - 120%. The method was adequately

validated during con current analy sis of samples , with percent r e covery ranging from 84 - 117% . The LLM V was 0.025 ppm for peppers.Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 13 of 30 Livestock commodities Because there are no established or proposed tolerances for livestock commodities, an enforcement method for livestock commodities is not required . 860.1360 Multiresidue Methods DER Reference List : 47761901.der.doc Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis HED ( DP# 325801 ) previously required the submission of multiresidue method testing data for fomesafen. In response, the petitioner submitted MRID 4776190 1 . The s ubmission has been reviewed by

HED , and the Executive Summary of the study

DER is reproduced below. Sy ngenta Crop Protection has submitted multiresidue testing data for fomesafen (free acid) followi ng testing and analy sis according to FDA Multiresidue Test Guidelines in PAM Vol. I (1/94). The Decision Tree for MRM Testing found in the Multiresidue Protocols was followed in determining the response patterns. Fomesafen (free acid) was tested through Protocols A, B, and C. Protocols D, E, and F were not tested as no residues were detected using Protocol C. The compound was not tested under Protocol G because it is not a substituted urea. Fomesafen does not have an N - methylcarbamate structure and d id not produce a response on the fluorescence detector under Protocol A. In Protocol B testing, methylated fomesafen was not recovered from Florisil; therefore, no additional work was performed under Protocol B. Fomesafen (free acid) did not produce a re sponse under Protocol C, using gas chromatography with either the nitrogen phosphorus or the electron capture detector (GC/NPD or GC/ECD). Therefore, it was not tested using Protocol D, E, or F. Conclusions : These data indicate that FDA multiresidue methods are not suitable for determining residues of fomesafen. The submitted data will be forwarded to U.S. FDA for further evaluation. 860.1380 Storage Stability DER Reference : 47 761902 .der.doc (c orn, soybean, cotton, and w heat matrices storage stabilit y data) DER Reference : 4 7473903.de1.doc (potato tuber concurrent storage stability data) DER Reference : 4 7473903.de2.doc (potato processed commodities concurrent storage stability data) DER Reference : 4 7473902.de1.doc (tomato fruit concurrent storage st ability data) DER Reference : 4 7473902.de2.doc (tomato processed commodities concurrent storage stability data) DER Reference: 47941402.de2.doc (pepper fruit concurrent storage stability data) Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis Residue C hemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger Sample storage duration and conditions The storage durations and conditions of potato samples from the submitted magnitude of the residue and processing studies are presented in Table 4 ; the st orage durations and conditions of pepper samples from the submitted magnitude of the residue study are presented in Table 4 .Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 14 of 30 Table 4 also includes the storage conditions and durations o f samples from the crop field trial , processing, and field rotational crop studies which were submitted to support previous petitions (PP#s 1E6228, 9F5068, 6E4653 , and 9F7563 ). Table 4 . Summary of Storage Conditions and Durations of Sam ples fromCrop Field Trial, Processing, and

Field Rotational Crop Studies. Matrix Sto rage

Tem perature (°C) Actual Storage

Duration Interval of Demonstrated Storage Stability Samples from Previous Petitions (PP#s 1E6228, 9F5068, and 6E4653)

reviewed under DP# 325801, 4/25/06, D. Davis Cotton Field Trials (MRID 44754701) Cotton gin bypro ducts ~ - 18 232 - 324 days (7.6 - 10.7 months) Storage stability data indicate that r esidues of

fomesafen appear to be erratic in/on cotton gin byproducts , but overall show general stability ; corrected stored recoveries w ere 69% at 2.5 mo nths, 80% at 3.2 months , 142% at 8.8 mo nths, and 68% at 14.6 months. Soybean Processing Study (MRID 45093601) Soybean hulls - 20 294 days (9.7 months) Storage stability data indicate that r esidues of

fomesafen appear to be relatively stable in/on soybean hulls s tored frozen at - 31 to - 3 oC for up to ~15 months. Soybean refined oil 288 days (9.5 months) Storage stability data indicate that r esidues of

fomesafen appear to be relatively stable in/on soybean oil for up to ~9 months but increased to a recovery of 149% by ~15 months . Field Rotational Crop Study (MRID 00158936) 1 Corn forage - 20 235 - 272 days (7.7 - 8.9 months) Storage stability data indicate that r esidues of

fomesafen appear to be relatively stable in/on corn K+CWHR, forage, and stover, and w heat forage and straw s tore d frozen at - 31 to - 3 oC for up to ~15 months. Corn cob 178 - 223 days (5.8 - 7.3 months) Corn fodder 178 - 223 days (5.8 - 7.3 months) Wheat forage 361 - 388 days (11.9 - 12.7 months) Wheat straw 289 - 339 days (9.5 - 11.1 months) Field Rotational Crop Study (MRID 45268501) Field corn, forage < - 10 280 - 316 days (9.2 - 10.4 months) Storage stability data indicate that r esidues of

fomesafen appear to be relatively stable in/on corn forage and stover, and w heat forage and straw s tored frozen at - 31 to - 3 oC for up to ~15 months. Field corn, stover 239 - 279 days (7.9 - 9.2 months) Sorghum, forage 232 - 289 days (7.6 - 9.5 months) Sorghum, stover 182 - 273 days (6.0 - 9.0 months) Samples from Previous Petition (PP#9F7563) reviewed under DP# 365199 and 366116, 1/21/201 0, C. Olinger Potato Field Trials and Processing Study (MRID 47473903)Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 15 of 30 Table 4 . Summary of Storage Conditions and Durations of Sam ples fromCrop Field Trial, Processing, and

Field Rotational Crop Studies. Matrix Sto rage

Tem perature (°C) Actual Storage

Duration Interval of Demonstrated Storage Stability Potato tuber - 40 to - 6 316 - 399 days (10.4 - 13.1 months) Concurrent storage stability data indicate that

r esidues of fomesafen appear to be relatively stable for u

p to 420 days in/on fr ozen potato tuber , 311 days in potato flakes , 308 days in potato chips , and 307 days in wet potato peel. Potato, tuber (RAC) - 40 to - 6 308 days (10.1 months) Potato, flakes 299 days (9.8 months) Potato, chips 298 days (9.8 months) Potato, w et pee l 293 days (9.6 months) Tomato Field Trials and Processing Study (MRID 47473902) Tomato fruit - 40 to - 5 211 - 302 days (6.9 - 9.9 months) Concurrent storage stability data indicate that

r esidues of fomesafen appear to be relatively stable for up to 319 day s in/on tomato fruit and 236 days in tomato paste and puree. Tomato, fruit (RAC) - 40 to - 5 241 days (7.9 months) Tomato, paste 229 days (7.5 months) Tomato, puree 229 days (7.5 months) Samples from Current Petition ( PP# 9F7667 ) Pepper Field Trials (MRID 47941402 ) Pepper fruit - 29 to - 15 458 days (15.1 months) Concurrent storage stability data indicate that

residues of fomesafen appear to be relatively stable for up to 458 days in/on pepper fruit. 1 For the field rotational crop study reported in MRID 00158936, the dates of sample analysis were not provided. The maximum storage interval for each sample, based on the study completion date, was calculated by the study reviewer. Storage stability

data S torage stability data were concurrently gener ated with the potato field and processing studies. For each crop, control samples of the respective matrices were fortified with fomesafen at ~0.25 ppm and placed in storage under the same frozen conditions as the treated samples. No zero - day analy ses we re conducted on the fortified samples placed into storage. Rather, triplicate stored samples were analy

zed along with a control sample and freshly fortified samples at an interval reflecting the maximum storage intervals from the field and processing stud ies . Average corrected recovery

ranges of f

omesafen were: 7 8 - 9 0 % in potato tubers after 420 day s, 7 9 - 99 % in potato flakes after 311 day s, 72 - 7 7% in potato chips after 308 day s, and 71 - 8 1 % in potato wet peel after 30 7 day s . Although no 0 - day analy sis was conducted, the data indicate that f omesafen is stable under frozen storage conditions at the maximum intervals tested . These data indicate that no corrections of residues need to be applied to the study results . Storage stability

data were concurrently generated with the pepper field study . Control samples were fortified with fomesafen at ~0.25 ppm and places in storage under the same frozen storage conditions as the treated samples. Triplicate stored samples were analy zed along with a controlFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 16 of 30 sample and freshly

fortified sample at an interval reflecting the maximum storage intervals from the field study . R ecovery ranges of fomesafen were 92 - 119% in pepper fruit after 458 day s. These data indicate that fomesafen is stable under frozen storage conditio ns at the maximum interval tested. These data indicate that no corrections of residues need to be applied to the study results. 860.1400 Water, Fish, and Irrigated Crops There are no proposed uses that are relevant to this guideline topic . 860.1460 Foo d Handling There are no proposed uses that are relevant to this guideline topic. 860.1480 Meat, Milk, Poultry, and Eggs The re are no livestock feedstuffs associated with the proposed use on peppers ( PP# 9F7667 ) . The only livestock feedstuffs associate d with the proposed uses in PP#9F7563 are potato culls and processed waste. The dietary burdens of fomesafen to beef and dairy cattle resulting from the proposed use on potato and the registered use s on cotton, dry and snap beans, and soy

bean, are present ed in Table 5 . The dietary burdens were calculated according to the Agency guidance on constructing maximum reasonably balanced diets (June 30, 2008) and used the proposed and existing tolerances for feedstuffs. The calculated dietary burdens are 0.05 4 p pm for beef cattle and 0.0 19 ppm for dairy

cattle. There are no poultry and swine feedstuffs associated with the proposed uses.Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 17 of 30 Table 5 . Livestock Dietary Burdens for Fom esafen. Feedstuff Feedstuff Ty pe 1 % Dry Matter 2 % Diet 2 Estimated Tolerance Dietary Contribution (ppm) 3 Beef Cattle Cotton hulls R 90 10 0.025 ppm 0.003 R not registered 4 R -- 5 -- -- Potato processed wa ste CC 15 30 0.025 ppm for potato 0.050 CC not registered/ reasonable 4 CC -- 50 -- -- Soybean, meal 5 PC 92 5 0.02 ppm 0.00 1 TOTAL BURDEN 100 0.05 4 Dairy Cattle R not registered R -- 45 -- -- Potato processed wa ste CC 15 10 0.025 ppm for potato 0.017 CC not registered4 CC -- 35 -- -- Soybean, meal 5 PC 92 10 0.02 ppm 0.002 TOTAL BURDEN 100 0.0 19 1 R = Roughag e; CC = Carbohydrate concentrate ; and PC = Protein concentrate . 2 Table 1 Feedstuffs ( June 200 8 ). 3 Contribution = (tolerance /% DM x % in diet) for beef and dairy cattle. 4 Although fomesafen is registered for other feedstuffs not listed in the dietary burden, only the feedstuffs which will result in the maximum dietary contribution were included. The calculation follows the guidance on constructing maximum reasonably balanced diets (June 30, 2008). 5 Currently, soybean tolerance is established at 0. 05 ppm . HED has since recommended that the tolerance on soybean be reduced to 0.02 ppm (D. Davis, DP No. D325801, 4/25/06). HED continues to recommend that these tolerances be updated. A ruminant feeding study was not submitted and is not needed for the purpose of this petition. HED concludes that the registered uses of fomesafen on cotton, dry and snap beans, and soy

bean and the proposed use of fomesafen on potato result in a 40 CFR §180.6(a)(3) situation for livestock commodities; there is no reasonab le expectation of finite residues in livestock. Therefore, no livestock feeding studies are required to support the proposed/registered uses of fomesafen sodium. Sy

ngenta should note that if additional uses are proposed in the future which result in an i ncrease in the dietary burden, livestock feeding studies may be required.Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 18 of 30 860.1500 Crop Field Trials DER Reference List 47473903.de1 (Potato) Residue Chemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger 47941402.der ( Pepper) A summary

of th e reviewed crop field trial data for potato and pepper is presented in Table 6 . T able 6 . S ummary of Residue Data fromCrop Field Trials with Fom esafen . Commodity Total Applic.

Rate (lb a e /A) PHI

(days) Residue Levels (ppm)

n Min. Max. HAFT 1 Median (STMdR) Mean

(STMR) Std. Dev. Potato (Proposed use = One preemergence application after planting but before crop emergence at 0.25 lb ae/A; 70 - day PHI) Potato tubers 0.237 - 0.263 70 - 141 26 <0.025 <0.025 <0.025 0.025 0.025 --- Pepper (Proposed use = On e preplant non - incorporated preemergence application up to 7 days prior to transplanting of peppers at 0.375 lb ae/A; 60 day PHI ) Pepper fruit 0.362 - 0.3 85 59 - 121 26 <0.025 <0.025 <0.025 0.025 0.025 -- - 1 HAFT = Highest Average Field Trial. Potato Sy ngenta Crop Protection has submitted field trial data for fomesafen on potatoes. Thirteen trials were conducted in the United States in Zones 1 (NY; 1 trial), 2 (MD, NC and NJ; 3 trials), 3 (FL ; 1 trial), 5 (MI

and WI ; 2 trials), 8 (CO ; 2 trials), and 11 (ID and WA; 4 trials) during the 2006 growing season . At each test location, a single preemergence application of Reflex® Herbicide (EPA Reg. No. 100 - 993) was made to potatoes at 0.237 to 0.263 lb a e (acid equivalents) /A. Reflex® Her bicide is a soluble concentrate liquid formulation containing 22.8% sodium salt of fomesafen as the active ingredient (equivalent to 2 lb ae/gal of fomesafen). Applications were made using ground equipment in spray

volumes of 16 - 36 gal/A without an adjuvant. Samples of mature potatoes were collected at a PHI

of 70 - 141 day s. Additional samples were collected from one trial to conduct a processed food and feed study ; refer to the 860.1520 DER for MRID 47473903 for the study details and results. Samples of potatoes were analy zed for residues of fomesafen using a LC/MS/MS method based on an HPL C/UV method (GAM - RM - 001/86), entitled “The Determination of PP021 in Soy beans

– A High Performance Liquid Chromatographic Method,” which is an enforcement method for f omesafen. The method was adequate for data collection based on adequate concurrent recovery data. The LLMV was 0.025 ppm for potato. The maximum storage duration of potatoes from harvest to analysis was 399 day s (13.1 months) for analy sis of fomesafen. Sample storage conditions and durations are supported by concurrent storage stability

data. However, zero - day data were not provided with the storage stability study . The petitioner is reminded that storage stability studies should alway s include a zero - day sampling interval to ensure that the samples were fortified properly [see OPPTSFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 19 of 30 860.1380(d)(6)(i)]. Residues of fomesafen were less than the LLM V (<0.025 ppm) in/on potatoes harvested 70 - 141 day s following a single pre - emergence application of the 2 lb ae/gal SL formulation of fomesafen at a total rate of 0.237 - 0.263 lb ae/A. Pepper Sy ngenta Crop Protection has submitted field trial data for fomesafen on peppers . Thirteen crop trials were conducted in the United States . Nine trials were conducted on bell peppers in Zones 2 (NJ, NC, and MD, 3 trials), 3 (FL; 1 trial), 5 ( MIand OH ; 2 trials ), 6 (TX; 1 trial) and 10 (CA, 2 trials), and four trials were conducted on non - bell cultivars (chili peppers) in Region 3 (FL , 1 trial), 6 (TX, 1 trial), 5 (MI , 1 trial), and 10 (NM, 1 trial) during the 2006 growing season. At each test location, a single broadcast application to soil surface of Reflex® Herbicide (EPA Reg. No. 100 - 993) was made prior to transplanting peppers at a rate of 0 .3 62 to 0. 385 lb a e /A. Reflex® Herbicide is a SL formulation containing 22.8% sodium salt of fomesafen as the active ingredient (equivalent to 2 lb ae/gal of fomesafen). Applications were made using ground equipment in spray

volumes of 19 - 35 gal/A without an adjuvant. Pepper fruit samples were harvested at commercial maturity , 59 to 121 day s after treatment, 56 to 115 day s after transplanting. Samples of raw pepper were analy zed for residues of fomesafen using an ultra performance liquid chromatography method with mass spectrometry detection (TMR0626B) based on a GC/NPD method. The method was adequately validated during concurrent analysis of samples. The LLMV was 0.025 ppm for pepper. The maximum storage duration of pepper from harvest to analy sis wa s 398 day s ( 13 .1 months) for analy sis of fomesafen . Sample storage conditions and durations are supported by concurrent storage stability

data. Residues of fomesafen were less than the LLM V (<0.025 ppm) in/on peppers harvested 59 - 121 day s following a s ingle pre - transplant application of the 2 lb ae/gal SL formulation of fomesafen at a total rate of 0.3 62 - 0.3 85 lb ae/A. Conclusions . The submitted field trials for potatoes are acceptable and support the proposed uses, as the potato metabolism data gap h as been satisfied with the submitted confined rotational crop metabolism study . An adequate number of trials were conducted in the appropriate geographic regions at ~1x the maximum proposed rate using Reflex® Herbicide, and the appropriate samples were co llected from each test around the proposed PHI . The confined rotational crop metabolism study does not identify

any additional residues of concern, and thus the field trial data are adequate. Based on these data, HED recommends a tolerance of 0.025 ppm f or residues of fomesafen in/on potatoes. The submitted field trial data for fomesafen on peppers are acceptable and support the proposed uses. An adequate number of trials were conducted in the appropriate geographic regions at ~1x the maximum propos ed r ate using Reflex® Herbicide , and the appropriate samples wereFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 20 of 30 collected from each test around the proposed PHI . All treated samples bore residues below the LLM V (<0.025 ppm). Based on these data, HED recommends a tolerance of 0.025 ppm for residues of fo mesafen in/on bell and non - bell peppers . 860.1520 Processed Food and Feed DER Reference List 47473903.de2 (Potato) Residue Chemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger T he observed processing factors reported for potatoes , resulting fr om treatment at 1x, are presented in Table 7 . Table 7 . Summary of Observed Processing Factors for Fom esafen in Potatoes Following Treatm ent at 1x .

RAC Processed Commodity Processing Factor Potato , tuber Flakes NC 1 Chips NC We t peel NC 1 NC = Not calculated. The processing factor could not be calculated bec ause residues were below the LLMV (<0.025 ppm) in both the RAC and the processed fraction s. Potato Sy ngenta Crop Protection submitted magnitude of the residue data for f omesafen on the processed commodities of potatoes. Samples used for processing were generated from two potato field trial conducted in ID (Zone 11) during the 2006 growing season. The test formulation used in the trial was Reflex® Herbicide (EPA Reg. No. 100 - 993), a SLformulation containing 22.8% sodium salt of fomesafen as the active ingredient (equivalent to 2 lb ae/gal of fomesafen). Potatoes were harvested 130 day s following a single preemergence application of a 2 lb ae/gal SL formulation of fomesa fen at 0.256 lb ae/A (~ 3 x field application rate). Application was made using ground equipment in a spray volume of 20 gal/A without an adjuvant. The potatoes were processed into potato flakes, chips and wet peel. Samples of potatoes and potato processe d commodities were analy zed for residues of fomesafen using a high performance liquid chromatography method with tandem mass spectrometry detection (L C/MS/MS) based on an HPL C/UV method (GAM - RM - 001/86), entitled “The Determination of PP021 in Soy beans

– A High Performance Liquid Chromatographic Method,” which is an enforcement method for fomesafen. The method was adequate for data collection based on adequate concurrent recovery data. The lowest level of method of validation (LLM V) was 0.025 ppm for potat o tuber and processed commodities flakes, chips, and wet peel. The maximum storage duration of the processing study samples were 308 day s ( 10.1 months) from harvest to analy sis for potatoes (RAC) and 299 day s (9.8 months), 298 day s (9.8 months), and 293 d ay s (9.6 months) from processing to analy sis for potato flakes, chips and wet peel, respectively . Sample storage conditions and durations are supported by concurrent storage stability data. However, zero - day data were not provided with the storage stabil ity study . The petitioner is reminded that storage stability studies should alway s include a zero - day sampling interval to establish the residue levels present at the time samples are placed into storage [see OPPTS 860.1380(d)(6)(i)].Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 21 of 30 Residues of fomesaf

en were less than the LLMV (<0.025 ppm) in/on the potato tuber (RAC) and potato processed commodities. Therefore, concentration factors could not be calculated. The petitioner is reminded that samples used in processing studies should contain field - treat ed quantifiable residues so that concentration factors can be determined. Field treatment of the processing samples should have been done at exaggerated application rates to ensure that the samples were fortified properly [see OPPTS 860.1 520 ( c )( 2 ) ] . Acco rding to Tables 2 and 3 of OPPTS 860.1520, the theoretical concentration factors for potato processed fraction are 4.0x for processed waste (wet peel) and 4.7x for flakes/granules. Conclusions . The results of submitted potato processing study show that residues of fomesafen were each below the LLMV (<0.025 ppm) in/on the respective RACs following application of Reflex® Herbicide at ~ 1x . Following processing of RACs bearing nonquantifiable residues , no measurable processing factors can be calculated bec ause the processed commodities of potatoes also bore residues below the LLM V (<0.025 ppm). The Agency would have preferred the use of exaggerated rates in the conduct of the processing studies to y ield RACs with quantifiable residues ; the registrant provi ded no justification for conducting the study at only a 1x rate . Since the proposed use is for preemergence application and all RAC samples from the current potato field trials show residues below the LLM V and the residue data cover all significant growin g regions for the crop requested as delineated in OPPTS 860.1500, for the purpose of this petition only , HED recommends a waiver f or the conduct of new potato processing studies at exaggerated rates . The submitted processing study for potatoes is adequate , as the potato metabolism data gap has been satisfied with the submitted confined rotational crop metabolism study . The confined rotational crop metabolism study does not identify

any additional residues of concern, and thus the potato processing study is adequate. 860.1650 Submittal of Analytical Reference Standards Analy tical standards for fomesafen are currently available in the EPA National Pesticide Standards Repository (personal communication with Theresa Cole , 9 /20/10 ). T he standard has an expiration date of August 2012 . Analy tical reference standards of fomesafen must be supplied and supplies replenished as requested by

the Repository . The reference standards should be sent to the Analy tical Chemistry Lab, which is loc ated at Fort Meade, to the attention of either Theresa Cole or Thuy Nguyen at the following address: USEPA National Pesticide Standards Repository /Analy tical 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.)Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 22 of 30 860.1850 Confined Accumulation in Rotational Crops Reference List: 47937602.der.doc Sy ngenta has submitted a co nfined rotational crop study with [trifluo ro methylphenyl - U 14 C] fomesafen (TMP label; specific activity 55.8 μCi/mg ) and [nitrophenyl - U 14 C] fomesafen (NP label; specific activity 56.2 μCi/mg ). Each radiolabeled test substance was formulated as SLand applied as a single bare - ground spray in plots in Madera, CA at a rate of 0.375 lb ae/A ( 1x the maximum proposed seasonal rate for any rotatable crop). Rotational crops (wheat, soy bean, potato, spinach, radish and carrot) were planted 90/91, 224 and 270 days after soil treatment, after which the total radioactive residues (TRR) of the crops w as quantified. Phy totoxicity necessitated usage of the following rotational crops and plant back intervals (PBI): 90 day PBI for wheat (forage, hay , straw, grain) as the small grain; 91 day PBIfor soy

beans (forage, hay , seeds) as a leafy

vegetable and po tatoes (foliage, roots) as a root vegetable; 224 day PBIfor wheat (forage, hay , straw, grain), radish (foliage, root), and spinach (immature, mature); 270 PHI for wheat (forage, hay , straw, grain), carrot (foliage, root), and spinach (immature, mature). Raw agricultural commodities (RACs) were harvested at appropriate intervals for analysis. TRR accumulated at ≥0.01 ppm in all rotational crop matrices planted in the 90/91, 224 and 270 day PBI s, except for radish roots. The majority

of radioactivity was extracted from rotational crop matrices using ACN/water. In some cases, additional extract ions were necessary to remove radiolabel from the PES. Ty pically the PES was extracted further with ACN:0.5 M KOH, 6 M HCl, 72% sulfuric acid , 24% KOH, and 80% dioxane in 0.05 M HCl . Total radioactive residues (TRR) in RACs were determined by combustio n and may

be found in Table 8. TRR in extracts were determined by liquid scintillation counting (L SC). Fomesafen and its metabolites were quantified and determined by liquid chromatography with ultraviolet detection ( LC /UV ) , liquid chromatography- mass s pectrometry ( LC /MS ) and nuclear magnetic resonance (NMR) . I dentification was confirmed by thin - layer chromatography ( TLC ) . Total radioactive residues (TRR, ppm) were highest in all commodities at the 90/91 day PBIand decreased at the longer PBI s of 224 and 270 day s. The TRR in the 224 and 270 day s PBI samples were generally

comparable. Residues in the wheat commodities were highest in the 90 days PBIsamples with fomesafen the highest residue , ranging from 0.01 ppm in grain to 0.329 ppm in the hay . T he other major residue s found in wheat were trifluoroacetic acid (TFAA ) conjugates in forage, hay and straw (0.019

– 0.064 ppm). At the later PBI intervals of 224 day s and 270 day s, fomesafen decreased in grain, forage, hay

and straw. The TFAA conjugates also had the highest residues at the 90 day PBI , 0.035, 0.064 and 0.047 ppm being the maximum residues in the forage, hay and straw, respectively . No other major residue was found in these commodities. Three different root crops were used, potatoes at the 91 day PBI , radish at the 224 day PBIand carrots at the 270 day

PBI . The residues in the tubers or roots were low across all three crops (TRR < 0.01 ppm). The residue was made up of fomesafen, R290493 and TFAA conjugates. Residues in the potato, r adish and carrot foliage tops were higher, with the major residueFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 23 of 30 comprised of fomesafen and TFAA conjugates. For potato, radish and carrot foliage, the highest fomesafen residues were 0.005, 0.011, and 0.017, respectively , and highest TF AA conjugate resi dues 0.013, 0.023, and 0.017 ppm TRR, respectively . R290493 found in potato foliage at 25.9% TRR as well, at 0.007 ppm TRR. S oy beans were planted at the 91 day PBI , and spinach at the 224 day and 270 day

PBI . The highest residues were found in the 91 day PBIsoy bean forage and hay . The major components of the residue in the soy

bean forage and hay

were a TFAA conjugate (0.035

– 0.136 ppm) , a R052850 lipid conjugate (0.02

– 0.061 ppm) , and R290493 (0.015 - 0.016 ppm) . Residues of fomesafen were low (less than or equal to 0.003 ppm) or not detected in the soy bean forage, hay or seed. The only

residue detected in soy

bean seed was 0.005 ppm TFAA conjugate. Lower residues were found in the immature and mature spinach at the 224 and 270 day PBI , with the maj or residue components being fomesafen and TFAA conjugate. The maximum TRR of fomesafen in spinach was 0.015 ppm and the maximum TRR of TFAA conjugate was 0.023 ppm. R290493 was found in 224 day PBIimmature spinach at >10% TRR, but at only 0.002 ppm TRR. The major components taken up in rotated crops are fomesafen and TFAA conjugates. R052850 lipid conjugate reached 0.061 ppm and was unique to soy bean forage and hay

(although Peak 9 in 90 day PBITMP - label wheat straw may correspond to R052850). The up take results in low residues of fomesafen or TFAA conjugates, except for fomesafen found in the wheat hay and straw at up to 0.329 ppm. The dates of application, harvest, combustion, extraction and analysis were reported. No storage stability determination was reported as processing, extraction and analy sis did not exceed 4 - 6 months from harvest. Based on the submitted confined rotation crop study , the petitioner described the metabolic pathway of fomesafen. Fomesafen is cleaved at the bipheny l eth er linkage (probably glutathione - mediated) to TMP moiety 2 - chlor - 4 - trifluoromethylphenol (not observed) and Cy s conjugate R290493. 2 - chloro - 4 - trifluoromethylphenol is further rapidly converted to either TFAA conjugates (A and B) and/or R052850 lipid conju gate (in soy bean foliage RACs). Formation of TFAA conjugates reflects opening/extensive oxidation of the phenyl ring. TABLE 8 . Total Radioactive Residues (TRRs) in Rotational Crops .

Matrix Plant - back interval (days) NP Label TMP Label ppm ppm Whe at Forage 90 0.141 0.180 224 0.038 0.034 270 0.027 0.039 Wheat Hay 90 0.515 0.526 224 0.075 0.074 270 0.100 0.113 Wheat Straw 90 0.823 0.864 224 0.239 0.115 270 0.139 0.107 Wheat Grain 90 0.027 0.024 224 0.009 0.006 270 0.009 0.012Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 24 of 30 TABLE 8 . Total Radioactive Residues (TRRs) in Rotational Crops .

Matrix Plant - back interval (days) NP Label TMP Label ppm ppm Soyb ean Forage 91 0.058 0.142 Soybean Hay 91 0.169 0.364 Soybean Seeds 91 0.013 0.025 Potato Foliage 91 0.027 0.061 Potato Root 91 0.008 0.008 Spinach, Immature 224 0.019 0.024 270 0.024 0.040 Spinach, Mature 224 0.015 0.025 270 0.013 0.029 Radish F oliage 224 0.014 0.031 Radish Roots 224 0.005 0.009 Carrot Foliage 270 0.068 0.087 Carrot Roots 270 0.004 0.010 Table 9 . Sum ma ry of Major Residues Found in Fom esafen Confined Rotational Crop Study Analyte Residues Found - %TRR (Label Position in Pa rentheses) Fomesafen Wheat Forage (NP) 90/224/270 1

– 65.2/68.4/70.4 Wheat Forage (TMP) 90/224/270

–

36.1/11.8/35.9 Wheat Hay (NP) 90/224/270

– 63.9/50.7/48.0 Wheat Hay (TMP) 90/224/270

– 51.9/14.9/21.2 Wheat Straw (NP) 90/224/270

– 30.4/38.1/43.2 Wh eat Straw (TMP) 90/224/270

– 35.3/24.3/34.6 Wheat Grain (NP) 90/224/270

– 44.4/33.3/33.3 Wheat Grain (TMP) 90/224/270

– 25/16.7/16.7 Potato Foliage (NP) 91 day

– 18.5 Potato Foliage (TMP) 91 day

– 6.6 Potato Root (NP) 91 day

– 25.0 Potato Root (TMP) 91 day

– 25.0 Imma ture Spinach (NP) 224/270

– 57.9/62.5 Imma ture Spinach (TMP) 224/270 day

– 4.2/ 32.5 Mature Spinach (NP) 224 /270

– 60.0/53.8 Mature Spinach (TMP) 224/270 day

– 4.0/20.7 Radish Foliage (NP) 224 day

– 78.6 Radish Foliage (TMP) 224 day – 19.4 Radish Root (TMP) 224 day

– 44.4 Carrot Foliage (NP) 270 day

– 30.9 Carrot Foliage (TMP) 270 day

– 19.5 Carrot Root (NP) 270 day

– 25.0 Carrot Root (TMP) 270 day

– 10.0 Soybean Forage (NP) 91 day

– 3.4 Soybean Forage (TMP) 91 day

– 0.7 Soybean Hay (NP) 91 day

– 1.8 R052850 Conjugate Soybean Forage (TMP) 91 day

– 14.1 (0.02 ppm)

Soybean Hay (TMP) 91 day

– 16.8(0.061 ppm) Wheat Straw (TMP) 90/224/270

– 3.6/ND/ND (<0.031 ppm) TFAA Conjugates Wheat Forage (TMP) 90/22 4/270

– 20/73.5/51.3

Wheat Hay (TMP) 90/224/270

– 12.6/64.9/45.1 Wheat Straw (TMP) 90/224/270

– 9.9/28.7/17.8 Wheat Grain (TMP) 90/224/270

– ND/33.3/33.3 Soybean Forage (TMP) 91 day

– 26.0 Soybean Hay (TMP) 91 day

– 37.4 Potato Foliage (TMP) 91 day

– 37.7 Potato Root (TMP) 91 day

– 50 .0 Imma ture Spinach (TMP) 224/270

– 79.2/52.5 Mature Spinach (TMP) 224/270

– 92.0/55.2 Radish Foliage (TMP) 270 day

– 74.2 Radish Root (TMP) 270 day

– 33.3 Carrot Foliage (TMP) 270 day

– 19.5 Carrot Root (TMP) 270 day

–40.0 Soybean Seed (TMP) 91 day

– 2 0.0Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 25 of 30 Table 9 . Sum ma ry of Major Residues Found in Fom esafen Confined Rotational Crop Study Analyte Residues Found - %TRR (Label Position in Pa rentheses) R290493 2 - amino - 3 - (3

– methanesulfonyla mino - carbonyl - 4 - nitro phenylsulfany1) - propionic acid Soybean Forage (NP) 91 day

– 27.6

Potato Foliage (NP) 91 day

– 25.9 Potato Root (NP) 91 day

– 12.5 Imma ture Spinach (NP) 224 day

– 10.5 Wheat Forage (NP) 9 0/224/270

– 1.4/2.6/3.7 Wheat Straw (NP) 90/224/270

– ND/3.3/2.2 Soybean Hay (NP) 91 day

– 8.9 Imma ture Spinach (NP) 270 day

– 4.2 Mature Spinach (NP) 270 day

– 7.7 Radish Foliage (NP) 224 day

– 7.1 1 These values refer to the plant - back interval. In days NP = nitrophenyl label . TMP = trifluoromethylphenyl label. The major components in rotated crops are fomesafen, trifluoroacetic acid (TFAA) conjugates, R052850 conjugates, and R290493. The highest residues found of fomesafen were in wheat hay , fora ge and straw at levels up to 0.329 ppm for fomesafen; TFAA conjugates were found at levels up to 0.064 ppm in wheat commodities. The highest residues found of TFAA conjugates were in soy bean hay at levels up to 0.136 ppm. The highest residues found of R0 52850 lipid conjugate and R290493 were in soy bean forage and hay

at levels up to 0.061 ppm for R052850 lipid conjugate and 0.016 ppm for R290493. Conclusions . The submitted confined rotational crop data are adequate to satisfy data requirements. The stu dy

appears to have adequately delineated the nature of the residue in rotational crops. The metabolism of fomesafen appears to proceed in rotational crops via similar mechanisms and to be more extensive than that observed in primary crops. TFAA conjugate metabolites were identified in rotational crops that were not identified in primary crops. HED has determined that the residue of concern for the tolerance expression in rotation crops is fomesafen per se . HED has also determined that the residue of con cern for the risk assessment in rotational crops is fomesafen. The submitted confined study indicated the potential for quantifiable fomesafen residues in rotated crop commodities at 90/91, 224 and 270 day plantback intervals. 860.1900 Field Accumulation in Rotational Crops Reference List: 47761905 (No DER generated)

00158936.der.w

pd 45268501.der.w

pd Residue Chemistry Memo DP# 325801, 4/25/06, D. Davis Residue Chemistry Memo DP# 365199 and 366116, 1/21/2010, C. Olinger HED previously summarized (DP# 325801, 4/25/2006, D. Davis) the available field accumulation data for fomesafen. The available data consisted of: (i) MRID 00110509 which was reviewed by

the Environmental Fate and Effects Division (EFED) and was found to contain numerous deficiencies; (ii) MRID 00158936 , a field rotational crop study on field corn and winter wheat; and (iii) MRID 45268501 , a field rotational crop study on field corn and safened sorghum. HED previously concluded that the adequacy of these data cannot be determined unti l the nature of fomesafen residues in rotational crops has been delineated.Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 26 of 30 Sy ngenta has adequately

responded to HED’s concerns and comments regarding the analy tical method (P PRAM No. 66 ) used for the analy sis of fomesafen from a previously submitted fi eld rotational crop study

(MRID 00158936) (See DP barcode D365119 and 366116, C. Olinger, 1/21/2010) . Sy

ngenta has provided detailed information/data concerning: (i) when the fortification of external recoveries were performed; (ii) data to support the r eported LOQ of 0.01 ppm; (iii) data demonstrating that recoveries of the internal standard are linear relative to recoveries of fomesafen; and (iv) information on the identity of matrices fortified to validate the method. This deficiency

is resolved. As for the deficiency

of data concerning the nature of the residue in rotational crops, this data gap has been fulfilled with the submission of the confined rotational crop metabolism study as described above. This data can support rotation to other crops be yo nd those commodities that are currently

registered and proposed as pri mary crops . All plant back intervals (PBI s) for rotational crops on the draft label are acceptable, including a 4 month PBIfor small grains ( wheat and similar commodities), a 10 month PBIfor corn, peanuts , peas, rice, and seed corn, and an 18 month PBIfor alfalfa, sunflowers, sugar beets and sorghum. The submitted confined rotational crop study

is adequate to determine the nature of residues in rotational crops; the residue of conc ern for rotational crops is fomesafen (D373600, A. L aMay , 10 / 12 / 10). 860.1550 Proposed Tolerances/Tolerance Reassessments for Fomesafen Tolerances for fomesafen residues are listed in 40 CFR §180.433. The tolerance expression is in terms of “sodium sal t of fomesafen, 5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] -N - (methylsulfonyl) - 2 - nitrobenzamide.” HED has determined that the residue of concern for tolerance expression is fomesafen. Therefore, the established tolerance expression should be revised to be expressed in terms of fomesafen, by removing the phrase “sodium sal t of” from 40 CFR §180.433(a). Inaccordance with the HED Interim Guidance on Tolerance Expressions (5/27/09, S. Knizner), the tolerance expression for fomesafen should be revised to state: “Tolerances are established for residues of fomesafen, 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

fomesafen [5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] - N - (methylsulfonyl) - 2 - nitrobenzamide].” The available crop field trial data and revised analy tical method will support the prop osed tolerance of 0.025 ppm for pepper and potato . As all residues were below the LLM V (<0.025 ppm) in/on RAC samples treated at 1x, the Agency ’s tolerance spreadsheet was not used for determining the recommended tolerances. The petitioner’s draft label for Reflex® Herbicide reflects regional use of fomesafen on pepper and potato . However, the residue chemistry data submitted in support of this action are of sufficient geographic representation to support full U.S. registration; therefore, HED recommends that th i s tolerances be listed in the general section of 40 CFR §180.433. Note that the commodity term for pepper should be modified as described in table below. No tolerances are required for meat, milk, poultry , and eggs for the purpose of this petition. Sy ngenta should note that if additional uses are proposed in the future which result in an increase i n the dietary

burden, livestock feeding studies and animal tolerances may be required.Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 27 of 30 No Codex, Canadian, or Mexican MRL s have been established for residues of fomesafen in/on potato or pepper . Canadian MRL s have been established for residues of f omesafen in/on dry beans, lima beans, snap beans, and soy beans at 0.05 ppm, and a Mexican MRL of 0.05 mg/kg has been established for residues of fomesafen in/on soy beans. The registrant has advised the Agency that they intend to petition the Canadian gov ernment for revised tolerances to address any potential harmonization issues raised by establishing the new tolerances requested in this action. A summary

of the tolerance reassessment for fomesafen sodium is presented in Table 10 . Table 10 . Toleranc e Sum ma ry for Fom esafen Sodium Commodity Established/Proposed Tolerance (ppm) Recommended

Tolerance (ppm) Comments ; C orrect Commodity D efinition Proposed Tolerance Under PP#9F7563 Potato 0.025 0.025 Proposed Tolerance Under PP#9F7667 Pepper 0.025 0.0 25 Pepper, bell Pepper, non - bellFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 28 of 30 References DP#: 325801 Subject: Fomesafen Sodium. Residue Chemistry Summary

for the HED Human Health Risk Assessment, a Proposal To Amend Use on Soy beans, and Proposals to Add Uses on Cotton, Dry

Bean, and Snap Bean. PP#1E6228, PP#9F5068, and PP#6E4653. From: D. Davis To: J. Stone/J. Miller Dated: 4/25/06 MRIDs: 00158936, 00158937, 40346603, 44754701 - 44754704, 44754706, 44727901,

45093601 - 45093604, 45237101, 45259801, 45268501 - 45268503, 45313001, & 45342601 DP#: 3 651 99 and 366116 Subject: Fomesafen Sodium. Petition for the Establishment of Tolerances and Registration

of New Uses on Potato and Tomato; and Response to Data Gaps for Conditional Registration on Cotton, Dry Bean, and Snap Bean . Summary of Analy tical Chem istry

and Residue Data. PP#1E6228, PP#9F5068, PP#6E4653 , and PP#9F7563 . From: C. Olinger To: D . Kenny

/M. Walsh Dated: 1/21/2010 MRIDs: 47473901, 47473902, 47473903, 47761901, 47761902, 47761903, 47761904, and

47761905. Attachments: Appendix I International Residue L imit Status S heet Appendix I I Chemical Names and Structures of Metabolites I dentifiedFomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 29 of 30 Appendix I International Residue Limit Status Sheet 

## INTERNATIONAL RESIDUE LIMIT STATUS Chemical Name: 5 - [2 - chloro - 4 - (trifluorome thyl)phenoxy] - N - (methylsulfonyl) - 2 - nitrobenzamide Common Name: Fomesafen X Proposed tolerance □ Reevaluated tolerance □ Other Date: 5/27 / 10

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#9F7563 and PP# 9F7667 DP#: D373544 and D382067 Other Identifier: Residue definition (step 8/CXL): N/A Reviewer/Branch: M. Metzger/RAB7 Residue definition: fomesafen per se Crop (s) MRL (mg/kg) Crop(s) Tolerance (ppm) Potato 0.025 Pepper 0.025

Limits for Canada Limits for Mexico □ No Limits X No Limits for the crops requested □ No Limits X No Limits for the crops requested Residue definition: 5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] -N - (methylsulfonyl) - 2 - nitrobenzamide Residue definition: fomesafen Crop(s) MRL (mg/kg) Crop(s) MRL (mg/kg)

Notes/Special Instructions: S.Funk, 5/27/2010 .Fomesafen Sodium Summary of Analytical Chemistry and Residue Data DP#s: D373544 and D382067

Page 30 of 30 Appendix II Chemical Names of Metabolites Identified Identification of Compounds . Common name/code Figure C.3.1 ID No. Chemical name Chemical structure Fomesafen 5 - [2 - chloro - 4 - (trifluoromethyl)phenoxy] - N - (methylsulfonyl) - 2 - nitrobenzamide F 3 C

Cl O N O 2

O N H S C H 3 O O

R052850 3 - chloro - 4 - hydroxybenzoic acid O H Cl C O O H

Cys conjugate of sulfonamide (R290493) 2 - amino - 3 - (3

–methanesulfonylamino carbonyl - 4 - nitro - phenylsulfany1) - propionic acid N O 2

O N H S C H 3 O O S N H 2 O H O R012156 2 - NO 2 - 5 - OH benzoic acid O H C O O H

N O 2

R089135 2 - NH 2 - 5 - OH benzoic acid O H C O O H

N H 2

TFAA Trifluoroacetic Acid O O H F F F