Page 1 of 31 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460 OFFICE OF CHEMICA L SA FETY A ND POLLUTION PREVENTION MEMORANDUM Date: January 4 , 2011 SUBJECT: Fluazifop - P - Butyl. Amended Section 3 Registration R equest to Add New Uses on

Bananas, Citrus, Grapes, and Sugar B eet s. Summary of Analy tical Chemistry

and Residue Data. PC Code: 122809 DP Barcode: 385205 Decision No.: 42 133 4 Registration No. : 100 - 1001 Petition No.: 9 F7624 Regulatory Action: New Us e Registration Risk Assessment Type: NA Case No.: 2285 T XR No.: NA CAS No.: 79241 - 46 - 6 MRID No.: Summary Table Provided Below 40 CFR: 180. 411 FROM: Peter Savoia, Chemist

Risk Assessment Branch V Health Effects Division (7509P) THRU: William H. Do novan, Ph.D., Chemist

Risk Assessment Branch V Health Effects Division (7509P) TO: Kathry

n Montague/Michael Walsh, RM 23 Herbicide Branch Registration Division (7505P) MRID Sum ma ry Table MRID No. Study Type Com me nts 47874601 860.1500 (banana) 4 7874601.der.doc 47874602 860.1500 (citrus) 47874602.der.doc 47874603 860.1500 ( sugar beet ) 47874603.der.doc 47874604 860.1500 (grapes) 47874604.der.doc 47874605 860.1520 (grapes) 47874605.der.doc 47874606 860.1520 ( sugar beet ) 47874606.der.doc This memorandum revises the August 31, 2010 version (D38001 7) by refini ng the recommended fluazifop - P - butyl tolerance level for the dried pulp citrus processed commodity . The initial m emor andum was prepared by Versar, reviewed by

the Health Effects Division (HED) , and revised as needed for correctness, language and to reflect current Office of Pes ticide Programs (OPP) policies.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 2 of 31 Prior actions made to develop the fluazifop - P - butyl herbicide active ingredient (ai) have identified a number of studies that are r equired for completing data gaps. Inaccordance, a number of Data Call - In (DCI ) submissions have been provided by the registrant in order to satisfy these database requirements. These studies are as follows: • Carrot and endive nature of residue studies , test guideline 860.1300. • Ruminant and poultry nature of residue studies, test guideline 860.1300. • Radiovalidation study

made for the tolerance enforcement method proposed for analy zing plants, test guideline 860.1340. • Method validation study made for the tolerance enforcement method proposed for analy zing poultry , eggs and livestock, test guideline 860.1340. • Cattle and poultry

feeding studies, test guideline 860.1480. • Confined rotational crop study , test guideline 860. 1850. An assessment of these studies is currently in progress and will be addressed in a separate memorandum in due course. Should the results of the studies submitted in response to the registration DCI

impact the conclusions reached in the present doc ument , appropriate changes will be made at that time. No further discussion of these in review studies will be included in this memorandum. Executive Summary Fluazifop - P - butyl [(

R ) - 2 - (4 - ((5 - (trifluoromethyl) - 2 - py ridinyl)oxy

)phenoxy )propanoic acid, butyl ester] is a selective herbicide registered for postemergence control of perennial and annual grass weeds. It is the resolved isomer (R enantiomer) of fluazifop - butyl [( R,S ) - 2 - (4 - ((5 - (trifluoromethyl) - 2 - py ridinyl)oxy

)phenoxy ) propanoic acid, butyl ester]. After application fluazifop - P - butyl is rapidly hydroly zed to fluazifop acid (R enantiomer) where it accumulates in the meristems of grass weeds working to interrupt lipid sy nthesis in susceptible plants . Fluaz ifop - P - butyl end - use products are registered in the United States to Sy ngenta Crop Protection, Inc. under the trade names Fusilade ® , Fusion ® , Oramec ® , Tornado ® , and Ty phoon ®

. Th is herbicide active ingredient is the resolved isomer (R enantiomer) of flu azifop - butyl (PC code 122805) which has since been cancelled resulting in only fluazifop - P - butyl to be supported for re registration. The Residue Chemistry Chapter of the Fluazifop - P - Butyl TRED ( referred to herein as the Residue Chap ter) was issued on August 17, 2005 (DP No. 319907, S. L. Kinard, 0 8/17/2005). It provided the Residue Chemistry Assessments that went into the “Report on FQPA Tolerance Reassessment Progress and Interim Risk Management Decisions (TRE D) for fluazifop - P - butyl.” Inthe current petition, Sy ngenta Crop Protection, Inc. requests the establishment of permanent tolerances for the residues of fluazifop - P - butyl in/on the following crop and processed commodities:

Banana ................................ ................................ ................ 0.01 ppm Citrus (whole fruit) ................................ ............................ 0.05 ppm Citrus (dried pulp) ................................ .............................. 0.40 ppm Citrus (oil) ................................ ................................ .......... 0.05 ppm Citrus (juice) ................................ ................................ ...... 0.05 ppm Grapes ................................ ................................ ................ 0.01 ppmF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 3 of 31 Sugar beet (root) ................................ ................................ . 0.25 ppm Sugar beet (top) ................................ ................................ .... 1.5 ppm Sugar beet (dried pulp) ................................ ......................... 1.0 ppm Sugar beet (molasses) ................................ ........................... 3.5 ppm The end - use product relevant for this petition request is Fusilade® DX Herbicide (EPA Reg. No. 100 - 1070), an e mulsifiable c oncentrate formulation containing 24.5% ai of fluazifop - P - butyl (equivalent to 2 lb ai/gal). The petitioner wishes to amend the product label for Fusilade® DX Herbici de to add new uses on banana, citrus, grapes, and sugar beets. Fusilade® DX Herbicide is proposed for multiple foliar or vineyard/orchard floor applications at maximum seasonal rates of 1.125 lb ai/A for bananas, grapes, and citrus and 0 .75 lb ai/A for s u gar beets . Applications are to be made with an adjuvant using ground or aerial equipment. The proposed P re - H arvest Inter vals (PHI s ) for the requested new uses range from 0 day s on treatments made to bananas up to 90 day s for sugar beet applications . F lu azifop - butyl isomers are L ist B chemicals with parent and fluazifop - acid (free and conjugated) regulated for tolerance expression as the residues of concern used to determine misuse (DP No. D319907, S. L . Kinard, 08/17/20 05). It s registered uses include dry beans, carrot, cotton, endive (escarole) , macadamia nut, onion, peanut, pecan, soy bean, spinach, stone fruit, and sweet potato . It also carries tolerances with regional registrations on asparagus, coffee, pepper, and rhubarb along with being regist ered for use on lawns as a weed control application. Tolerances are established under 40 CFR §180.411(a) for residues of the herbicide fluazifop - P - butyl which include both the free and conjugated forms of its resolved isomer expressed as fluazifop. There are no Section 18 emergency exemptions in effect but fluazifop - P - butyl tolerances are likewise established under 40 CFR §180.411(c) which carry

regional restrictions expressed as fluazifop. The nature of the residue in both plants and livestock cannot yet be described as adequately understood. For the current action, an acceptable soy bean metabolism study

is available, and the soy bean metabolism study

will also support the proposed uses on the other crops addressed herein. T he Metabolism Assessment Review C ommittee (MARC) concluded that the residues of concern for tolerance expression for plants and animals are parent and fluazifop - acid (free and conjugated) since they are adequate to determine misuse . The MARC also concluded that the residues of concern in plants for risk assessment are parent, fluazifop - acid (free and conjugated), 5 - trifluoromethyl - 2 - py ridone, and 2 - (4 - hydroxy phenoxy ) propionic acid (free and conjugated). The residues of concern in animals for risk assessment are parent and fluazifop - acid (free and conjugated) (DP No. D 298939, S. L. Kinard, 6/22/20 04). There are adequate residue analy tical methods listed in PAM I I for tolerance enforcement and data collection. For the enforcement of tolerances for fluazifop - P - butyl residues of concern, a High Performance Liquid Chromatography /Ultra - Violet Spectrometry (HPL C/UV) method is available for crop commodities. In conjunction, HPL C/UV and Gas Chromatography /Mass Spectrometry (GC/MS) methods are available for milk and animal commodities. The stated quantitation limits are 0.02 - 0.05 ppm for crop commodities, 0.01 ppm for milk, and 0.02 ppm for animal tissues. In addition, the FDA PESTDATA database dated 11/01 (PAM Volume I , Appendix I ) indicates that fluazifop - butyl (only

) is completely

recovered using Multiresidue Methods Sections 302 (Luke Method; Protocol D) and 303 (Mills, Onley , and Gaither Method; Protocol E, nonfatty food).F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 4 of 31 To support this petition , the field trial samples were analy zed for residues of total fluazif op ( fluazifop - P - butyl, fluazifop free and conjugated) using either a GC/MS or Fluorine - 19 Nuclear Magnetic Resonance ( 19 F NMR) protocol. These procedures provide a total determination by hydroly zing the fluazifop ester or acid conjugates and then derivati z ing them to form the fluazifop methyl ester for quantitation with r esidues being reported as fluazifop . The protocols are adequate for data collection based up on acceptable method validation and concurrent method recoveries. The current petition request s the es tablishment of tolerances on dried pulp citrus and sugar beet top s, commodities which have been considered livestock feedstuffs. Following revision of the Table 1 Feedstuffs in 2008, sugar beet tops w ere removed as being a significant feed item , and thus it no longer contributes to the dietary burden of cattle. The potential contribution of citrus dried pulp to the livestock dietary

burden was considered by assuming a concentration factor of 13x and comparing the resulting residue contribution to that of soy bean hulls, the current roughage component in the dietary burden calculation. Since soy bean hulls has a higher to lerance than the recommended tolerance level of dried pulp citrus, the current tolerances on meat, milk, poultry , and eggs are con sidered adequate and should remain unchanged. This conclusion should be re - examined upon receipt of the requested processing study

for citrus. The submitted field trial data for bananas are adequate . The field trials were conducted according to th e proposed use rate and PHI . The maximum residues of total fluazifop were less than the 0.01 ppm L imit of Q uantitation (L OQ) in/on bananas harvested 0 day s after the last of three broadcast applications . For this application program, treatments were made using the 2 lb/gal E mulsifiable C oncentrate (EC) formulation applied at ≈ 1x the proposed seasonal use rate to the soil. Based on the LOQ, the best estimate for a tolerance for bananas is 0.01 ppm . The submitted field trial data for citrus are adequate . The field trials were conducted according to the proposed use rate and PHI . The maximum residues of total fluazifop were less than the 0.03 ppm LOQ in/on citrus harvested 12 - 14 day s after the last of three broadcast applications . For this application pr ogram, treatments were made to the orchard soil beneath the trees using the 2 lb/gal EC formulation applied at ≈ 1x to 2x the proposed seasonal use rate. Based on the LOQ, the best estimate for a tolerance for citrus is 0.03 ppm . The submitted field trial data for grapes are adequate . The field trials were conducted according to the proposed use rate and PHI . Th e maximum residues of total fluazifop were less than the 0.01 ppm LOQ in/on grapes harvested 49 - 50 day s after the last of three broadcast applications . For this application program, treatments were made to the vineyard floor beneath the grape vines using the 2 lb/gal EC formulation applied at ≈ 1x the proposed seasonal use rate. Based on the LOQ, the best estimate for a tolerance for grapes is 0.01 ppm .F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 5 of 31 The submitted field trial data for sugar beets are adequate having been appropriately made according to the proposed use rate and PHI . For this test program , both sugar beet tops and the roots were quantitated for determining the magnitude of the residue. The maximum residues of total fluazifop were 1.45 ppm in/on sugar beet tops and 0.23 ppm in/on sugar beet roots harvested 89 - 90 day s after the last of three broadcast foliar applications. Treatments were all made using the 2 lb/gal EC formulation applied at ≈1x the proposed seasonal use rate. The residue data for sugar beet root s were entered into the Agency ’s tolerance spreadsheet as specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determine an appropriate toleranc e level. The spreadsheet provides a best estimate of a tolerance at 0.25 ppm for the sugar beet roots. With regard s to sugar beet tops, no tolerance is needed for this commodity since it is no longer considered a significant feed item. The submitted sug ar beet and grape processing studies are acceptable. For sugar beets, total fluazifop residues concentrated in dried pulp (processing factor of 3.9x) and molasses (14x) but do not appear to concentrate in refined sugar (0.36x). For grapes, total fluazifo p residues do not appear to concentrate in raisins or juice ( <1x). Th i s data along with the sugar beet root HAFT (0.22 ppm), indicate that a tolerance is needed for fluazifop - P - butyl residues of concern in sugar beet dried pulp at 1.0 ppm and molasses at 3. 5 ppm. No tolerances are needed for the sugar beet refined sugar or the grape processed commodities. As was previously

concluded by

the Agency

(DEB No. 6343, M. J. Bradley , 08/15/1990) , the submitted citrus processing study is not acceptable . Given th e age of the original submission, the petitioner should provide a new study . While the processing study is conducted, tolerances for citrus processed commodities should be set based on maximum theoretical concentration factors for the appropriate fraction s: 2x for juice and 1000x for oil. These factors along with the citrus HAFT of 0.03 ppm, indicate that fluazifop - P - butyl tolerance levels for citrus juice and oil should be 0.06 and 30.0 ppm , respectively . With regard to dried pulp citrus, there is no theoretical concentration factor determined for this processed commodity . However, in a recent chlorantraniliprole review , an examination of 27 pesticides having dried pulp citrus tolerances was made to determine a practical maximum concentration factor (D P No. D361791, D. Rate, 01/08/2010). This review found concentration factors range between 2 - 13x for dried pulp citrus . Therefore, using the practical maximum concentration factor of 13x for fluazifop along with the citrus HAFT of 0.03 ppm, a resulting t olerance of 0.40 ppm should be set for dried pulp citrus . Regulatory Recommendations and Residue Chemistry Deficiencies Provided the petitioner submits a revised Section F, HED concludes that the residue chemistry database supp ort s a conditional registration and establishment of permanent tolerances for the proposed new uses of fluazifop - P - butyl. Tolerances are to be established for residues of the herbicide fluazifop - P - butyl, including its metabolites and degradates, in or on the commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only

the sum of fluazifop - P - butyl, butyl(R) - 2 - [4 - [[5 - (trifluoromethyl) - 2 - py ridinyl]oxy]phenoxy]propanoate, and the free and conjugated form s of the resolved isomer of fluazifop, (R) - 2 - [4 - [[5 - (trifluoromethyl) - 2 - py ridinyl]oxy]phenoxy]propanoic acid, calculated as the stoichiometric equivalent of fluazifop, in or on the commodity .F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 6 of 31 Banana ................................ ................................ ................ 0.01 ppm Fruit, c itrus , group 10 - 10 ................................ ................... 0.03 ppm Citrus, oil ................................ ................................ ........... 30.0 ppm Citrus, dried pulp ................................ ............................... 0. 40 ppm Citrus, juice ................................ ................................ ........ 0.06 ppm Grape ................................ ................................ .................. 0.01 ppm Sugar , beet , root ................................ ................................ . 0.25 ppm Sugar , beet , dried pulp ................................ ......................... 1.0 ppm Sugar , beet , molasses ................................ ........................... 3.5 ppm An unconditional registration may be appropriate upon determination of the adequacy of a n ew citrus processing study ( see requirements under Processed Food and Feed). A revised human - health risk assessment which includes these new crop uses is forthcoming in a separate document (D385178) . 860.1520 Processe d Food and Feed As was previously

co ncluded by

the Agency

(DEB No. 6343, M. J. Bradley , 08/15/1990), the submitted citrus processing study is not acceptable . Given the age of the original submission, the petitioner should provide a new study . 860.1550 Proposed Tolerances The proposed tole rances should be revised to reflect the recommended tolerance levels and correct commodity

definitions as specified in Table 8 . Background Fluazifop - P - butyl [(

R ) - 2 - (4 - ((5 - (trifluoromethyl) - 2 - py ridinyl)oxy

)phenoxy )propanoic acid, butyl ester] is a selec tive herbicide used for the post - emergence control of perennial and annual grass weeds. It is the resolved isomer (R enantiomer) of fluazifop - butyl (PC code 122805) which has since been cancelled resulting in only fluazifop - P - butyl to be supported for re - registration. The fluazifop butyl isomers are L ist B chemicals with parent and fluazifop - acid (free and conjugated) regulated for tolerance expression as the residues of concern used to determine misuse (DP No. D319907, S. L . Kinard, 08/17/2005). T he Phase 4 Reviews for fluazifop - butyl and fluazifop - P - butyl were completed on 02/26/1991. The subsequent Phase 5 review of these studies has also been completed. This includes the Residue Chemistry Science Assessments with respect to the Report on FQPA Tolerance Reassessment Progress and Interim Risk Management Decisions (TRED) for fluazifop - P - butyl issued on 08/17/2005. For review, the chemical structure and nomenclature of fluazifop - P - butyl, including its free aci d fluazifop - P a s well as the phy sicochemical properties of the technical grade of fluazifop P - butyl are presented below in Tables 1 and 2.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 7 of 31 Table 1. Fluazifop - P - butyl Nomenclature. Compound

N F 3 C O O H C H 3 O O C 4 H 9 ( n )

Common name Fluazifop - P - butyl Company experimental name Not available. IUPAC name Butyl (2 R ) - 2 - (4 - {[5 - (trifluoromethyl)pyridin - 2 - yl]oxy}phenoxy)propanoate CAS name (R ) - 2 - (4 - ((5 - (trifluoromethyl) - 2 - pyridinyl)oxy)pheno xy)propanoic acid, butyl ester CAS registry number 79241 - 46 - 6 End - use product (EP) Fusilade® DX (2 lb/gal EC; EPA Reg. No. 100 - 1070) Compound

N F 3 C O O H O O H C H 3

Common name Fluazifop - P (free acid) Chemical name (R ) - 2 - (4 - [5 - (trifluoromethyl - 2 - pyridinyl)oxy]phenoxy)propionic acid Table2. Physicochemical Properties of Fluazifop - P - butyl. Parameter Value Reference 1 Melting point/range Decomposes at 210 oC 164 oC at 0.02 mm Hg 2002 Farm Chemicals Handbook RCB No. 1674, 2/3/87, L. Cheng pH Not dispersible in w ater RCB No. 1674, 2/3/87, L. Cheng Density 1.22 g/cc (PAI) and 1.20 g/cc (T) at 20 oC RCB No. 809, 6/3/86, L. Cheng Water solubility 1 mg/L RCB No. 1674, 2/3/87, L. Cheng Solvent solubility Soluble in most organic solvents >500 g/L in acetone, dichlor om ethane, ethyl acetate, hexane, methanol, toluene, and xylene 2002 Farm Chemicals Handbook RCB No. 1674, 2/3/87, L. Cheng Vapor pressure 3 x 10 - 8 KPa at 20 oC RCB No. 809, 6/3/86, L. Cheng Dissociation constant, pK a - 3.1 (by calculation) RCB No. 809, 6/3/86, L. Cheng Octanol/water partition coefficient, Log(K OW ) 4.5 at 20 oC RCB No. 809, 6/3/86, L. Che ng UV/visible absorption spectrum Not available 1 DP No. D 348246, D. Soderberg , 09/16/2008F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 8 of 31 860.1200 Directions for Use A summary

of the proposed/amended use patterns for bananas, citrus, grapes and sugar beets is presented in Table 3. The information presented in Table 3 was obtained from a specimen label provided by

Sy ngenta for the Fusilade® DX Herbicide (EPA Reg. No. 100 - 1070). Table 3. Summary of Directions for Use of Fluazifop - P - butyl. Commodity Trade

Name (EPA Reg. N o.) Application

Timing, Ty pe, and Equipment Application

Rate (lb ai/A) Maximum

Number Applications per Season Maximum

Seasonal Application Rate (lb ai/A) PHI

(days) Use

Directions and Limitations Bananas Fusilade®

DX (100 - 1070) Ground and

aerial 0.375 3 1 .125 0 days RTI: 30 days Citrus Ground and aerial 0.375 3 1.125 1 4 days RTI: 21 days Grapes Ground and aerial 0.375 3 1.125 50 days RTI: 14 days Sugar beet Ground and aerial 0.375 2 0.75 90 days RTI: 14 days Do not enter or allow

worker entry into treated areas during the restricted entry interval (REI) of 12 hours following application. The general label use directions specify that: (1) adjuvants (crop oil concentrate, non - ionic surfactant, or other approved adjuvants) plus liquid nitrogen fer tilizer may

be used on soy

beans; (2) ground and aerial applications are to be made in a minimum of 5 gal/A; (3) for chemigation (sprinkler irrigation), adjuvants are not to be used in the manner described for use in conventional applications or applied with a sy stem connected to a public water sy stem; and (4) the restricted - entry interval is 12 hours. Rotational grass crops such as corn, sorghum and cereals are not to be planted within 60 days of last application. Conclusions : The label directions are ad equate to allow evaluation of the residue data relative to the proposed use. There are no aerial application restrictions specified on the label. For the banana, citrus , and grape field trials that were conducted, treatment was made to the orchard/vineyard floor below the plant canopy which is not an aerial application method. 860.1300 Nature of the Residue - Plants Residue Chemistry Memo, DP No. D 319907, 0 8/17/20 05, S. L. Kinard (TRED Residue Chemistry Chapter) HED MARC Decision Memo, DP No. D 298939, 0 6/22/20 04, S. L. Kinard The Fluazifop - P - Butyl Residue Chapter of the TRED (DP No. 319907 , S. L . Kinard, 08/17/2005 ) concluded that the nature of the residue in soy beans is adequately

understood. No new plant metabolism studies for the proposed new use cr ops were submitted as part of the current petition. T he MARC has determined that for tolerance expression, parent and fluazifop - acid (free and conjugated) are the residues of concern since they are adequate to determine misuse. The MARC also concluded th at the residues of concern in plants for risk assessment are parent, fluazifop - acid (free and conjugated), 5 - trifluoromethyl - 2 - py ridone, and 2 - (4 - hydroxy phenoxy ) propionic acid (free and conjugated).F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 9 of 31 860.1300 Nature of the Residue - Livestock Th e MARC has concluded that for tolerance expression and risk assessment, parent and fluazifop acid (free and conjugated) are the residues of concern since they are adequate to determine misuse . 860.1340 Residue Analytical Methods Residue C hemistry Memo, DP No. D 319907, 0 8/17/20 05, S. L. Kinard (TRED Residue Chemistry Chapter) Enforcement methods For the enforcement of tolerances for fluazifop - P - butyl residues of concern, PAM Vol. I I lists two methods, Method Ifor an imal tissues and milk and Method I I for oily and non - oily

crops. The stated detection limits are 0.02 - 0.05 ppm for crops, 0.01 ppm for milk, and 0.02 ppm for animal tissues. In Method I , samples (except fat) are extracted with acetonitrile/acetone/hexane , which separates residues of fluazifop and fluazifop - butyl (found in the acetonitrile/acetone layer) from residues of fluazifop lipophilic conjugates (found in the hexane layer). Fluazifop and fluazifop - butyl are determined in milk using an HPL C/UV instr umental technique. In tissue samples, fluazifop - butyl is converted to fluazifop via hydroly sis, and then its residues are methylated using diazomethane, and determined by

GC/MS. Fluazifop lipophilic conjugates (for both milk and tissue samples) are clean ed up by f

lorisil chromatography , hydroly zed to fluazifop, and determined by HPL C/UV. For fat, samples are extracted with chloroform/methanol at reflux (2 hours) and residues of fluazifop, fluazifop - butyl, and lipophilic conjugates are hydroly zed to fluaz ifop, methylated, and determined by GC/MS. For Method I I, residues of fluazifop - butyl, fluazifop, and any ester or acid conjugates are extracted from crop samples using acetonitrile and hydrochloric acid. Residues are then hydroly zed to fluazifop and cle aned up using a coagulation procedure, solvent partitioning, and silica column chromatography

for determination by

HPL C/UV. Residues may be confirmed by

GC/MS following methylation with diazomethane. Consequently , n either of the enforcement methods disti nguishes the optical isomers of fluazifop - butyl or fluazifop. Data collection methods Samples collected from the crop field trial and processing studies were analy zed for residues of fluazifop using either a GC/MS method or a 19 F NM R method . The GC/MS methods used were Method 45820 - M - 1 by

Zeneca (bananas in MRID No. 47874 6 01 ) and Method RR 91 - 014B by Zeneca (grapes in MRID Nos. 47874 6 04 & 47874 6 05 , sugar beet in MRID Nos. 47874 6 03 & 47874 6 06 , and citrus in MRID No. 47874 6 02 ) . The 1 9 F NMR method used was based on Plant Protection Division Analy tical Method no. 83 and was employed for analy zing a portion of the citrus studies that were provided (citrus in MRID Nos. 41373705 & 41373706 ) . Inall, these methods are based on the protocol s listed in PAM Vol. I I, Method I I . These procedures work by hydroly zing the target analy

tes (fluazifop - P - butyl, fluazifop, and any ester or acid conjugates) to a common moiety (fluazifop acid) for quantitation with r esidues being reported as fluazifop eq uivalents.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 10 of 31 For the GC/MS method used on bananas, residues are extracted from crop samples using a mixture of acetonitrile and dilute acid, hydroly zed to fluazifop using hydrochloric acid, and cleaned up on a silica SPE cartridge. Residues are derivatized to form the methyl ester of fluazifop prior to GC/MS quantitation. Inregard to the GC/MS method used on grapes, sugar beet and citrus, residues are extracted from crop samples using a mixture of acetonitrile and dilute acid. Residues are then hydr oly zed to fluazifop using hydrochloric acid, and cleaned up by solvent partitioning and adsorption chromatography . Residues are derivatized to form the methyl ester derivative of fluazifop prior to GC/MS quantitation. For the 19 F NMR method used on citru s, residues are extracted from crop samples using a mixture of acetonitrile and concentrated hydrochloric acid, hydroly zed to fluazifop using hydrochloric acid, and cleaned up by solvent partitioning. Residues are derivatized to form the methyl ester of f luazifop prior to 19 F NMR quantitation. Adequate method verification analy ses were made prior to the determination of the field samples using fluazifop - P - butyl and fluazifop - P fortified sugar beet tops (0.01 and 10 ppm), sugar beet roots (0.01 and 1.0 p pm), and grapes (0.01 and 1.0 ppm). Inaddition, acceptable concurrent method recoveries were obtained for fluazifop - P - butyl from fortified samples of bananas at 0.01 and 0.5 ppm, sugar beet root, dried pulp, and refined sugar at 0.01 and 1.0 ppm, sugar b eet tops at 0.01 and 10 .0 ppm, and grapes, grape juice and raisins at 0.01 and 1.0 ppm. For sugar beet molasses, acceptable concurrent method recoveries were obtained for fluazifop - P - butyl from samples fortified at 0.01 and 10 .0 ppm . H owever, the average concurrent recovery for sugar beet molasses was slightly below the generally acceptable range of 70 to 120% at the 15 .0 ppm fortification level. Similarly , for citrus study MRID No. 47874 6 02 , acceptable concurrent method recoveries were obtained for fluazifop - P butyl from samples fortified at 0.01 ppm . H owever, average concurrent recovery was slightly

below the generally

acceptable range of 70 to 120% for the citrus samples analy zed at the 1.0 ppm. For citrus studies MRID Nos. 41373705 and 41373706 , acc eptable concurrent method recoveries were obtained for fluazifop - P - butyl from samples fortified at 0.05 ppm (whole fruit and processed commodities) and 1 .0 ppm (whole fruit only ). The fortification levels are adequate to bracket expected residue levels of total fluazifop in banana, citrus, grape, and sugar beet matrices, except for the processed citrus commodities in which residues for chopped peel, dried pulp, molasses, and oil were higher than the fortification level. Conclusions : The existing GC/MS en forcement method s, or the modified versions, are adequate for collecting data on residues of fluazifop - P - butyl and fluazifop in/on banana, citrus, grape, and sugar beet commodities. The method will be adequate for tolerance enforcement purposes for these commodities. 860.1360 Multiresidue Methods Residue Chemistry Memo, DP No. D 319907, 0 8/17/20 05, S. L. Kinard (TRED Residue Chemistry Chapter) The FDA PESTDATA database dated 11/01 (PAM Volume I , Appendix I ) indicates that fluazifo p butyl is completely

recovered using Multiresidue Methods Sections 302 (Luke Method; Protocol D) and 303 (Mills, Onley , and Gaither Method; Protocol E, nonfatty food); recovery

using Section 304 (Mills Method; Protocol F, fatty food) is variable.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 11 of 31 860.138 0 Storage Stability 48412503.der.doc D. Soderberg Storage Stability of Residues of various crops and Processed Fractions Stored for up to 18 Month in Deep Freeze Storage stability

data have been reviewed in conjunction with earlier actions undertaken fo r fluazifop P - butyl which indicate that its residues are stable in a number of crop commodities. As such, its st ability has been investigated in a wide variety of frozen crop commodities and documented in several prior reports generated by Sy ngenta. Thes e reports demonstrate that residues of fluazifop are stable in/on soy

beans, sugar beets, green beans, strawberries, oilseed rape, coffee, cauliflower, onions, potatoes, peanuts, macadamia nuts, tomatoes, endive, and celery for durations of 3 to 28 months ( DP No. D 348246 , D. Soderberg , 0 9/16/ 20 08). Given the results obtained from the se prior studies , this data is adequate in directly supporting or can be translated to corroborate the sample storage intervals incurred in th ese field trials. Although no data were provided to substantiate the holding times that were incurred for many

of the processed commodities tested, none are needed since these analyses were made within thirty

(30) day s of production. A summary of the storage durations and conditions of th e samples from the crop field trials and processing studies provided to support this petition are presented below in Table 4 for review . Table 4. Summary of Storage Conditions and Intervals of Samples from Crop Field Trials. Matrix MRID Storage Te mp erature (°C) 1 Actual Storage Duration2 Interval of Demonstrated Storage Stability Banana 47874 6 01 ≤ - 20 217 to 282 days (7.2 to 9.4 months) None. Up to 28 months in a

variety of crops at - 20oC ± 10oC. Citrus 47874 6 02 < 0 24 to 71 days (0.77 to 2.4 months) None. Up to 28 months in a

variety of crops at - 20oC ± 10oC. 41373705 < - 18 456 to 686 days (16 to 25 months) Citrus (for processing) 41373706 < - 18 589 days (21 mo nths ) Citrus, dried pulp 41373706 < - 18 591 days (21 mo nths ) Citrus, oil 41373706 < - 18 654 days ( 2 3 mo nths ) Citrus, juice 41373706 < - 18 592 days ( 2 1 mo nths ) Grapes 47874 6 04 < 0 8 to 45 days (0.25 - 1.5 months) None. Up to 28 months in a

variety of crops at - 20oC ± 10oC. Grapes (for processing) 47874 6 05 < 0 36 days (1.2 months) Grap e, juice 47874 6 05 < 0 29 days (1.0 months) None. S torage stability data is not required because the samples we re extracted/analyzed within approximately 30 days from processing . 3 Grape, raisins 47874 6 05 < 0 43 days (1.4 months) Sugar beet , top 47874 6 03 < 0 9 - 75 days (0.25 - 2.5 months) None. Up to 28 months in a

variety of crops at - 20oC ± 10oC. Sugar beet , root 47874 6 03 < 0 9 - 75 days (0.25 - 2.5 months) 12 months in sugar beet root

(MRID No. 00157193). Sugar beet , root (for processing) 47874 6 06 < 0 48 days (1.6 months) Sugar beet , refined sugar 47874 6 06 < 0 53 days (1.8 months) None. S torage stability data is not required because the samples wereF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 12 of 31 Table 4. Summary of Storage Conditions and Intervals of Samples from Crop Field Trials. Matrix MRID Storage Te mp erature (°C) 1 Actual Storage Duration2 Interval of Demonstrated Storage Stability Sugar beet , dried pulp 47874 6 06 < 0 48 days (1.6 months) extracted/analyzed within approximately 30 days from processing . 4 Sugar beet , mo lasses 47874 6 06 < 0 48 to 51 days (1.6 to 1.7 months) 1 For all crops except bananas, storage temperature at the analytical facility was <0 o C prior to homogen iz ation and then ≤ - 15 o C until analysis. 2 Actual storage duration is from harvest to extraction. 3 For grapes, the storage duration betw een processing and extraction was 33 days for grapes, 26 days for grape juice, and 30 days for raisins. 4 For sugar beet s, the stora ge duration betw een processing and extraction was 28 to 31 days for molasses, 32 days for sugar beet roots, 32 to 33 days for dry pulp, and 33 days for refined sugar. Conclusions : The petitioner included a summary of the storage stability

data in each o f the field trial submissions. Submitted storage stability data demonstrate that total residues of fluazifop - P w ere stable in/on various crops and processed commodities . Data specifically for grapes, grape juice, raisins, citrus, citrus dried pulp, citru s oil, citrus juice, sugar beet tops, sugar beet dried pulp, sugar beet refined sugar, and sugar beet molasses are not available. For the grape and sugar beet processed commodities, storage stability data are not required because the samples were analy zed within approximately

30 day s of processing. For the other Raw Agricultural Commodities (RACs) , stability studies are available or existing data for other similar crops can be translated to substantiate the storage durations that were incurred. As such, the re are adequate stability data available to support the sample storage conditions and durations incurred for all of the RACs pursuant to this petition. For the most part, the storage stability studies which are noted were generally conducted at - 20oC whereas a majority of the samples were stored at <0oC prior to homogenization and then at ≤ - 15oC until analy sis at the laboratory (except bananas which were stored at the laboratory at < - 20oC). 860.1400 Water, Fish, and Irrigated Crops For the purpose of this summary , this guideline require ment is not relevant to this evaluation since Fluazifop - P - butyl has no registered or proposed uses on water or aquatic food and feed crops. 860.1460 Food Handling For the purpose of this summary , this guideline require ment is not relevant to this evaluation since Fluazifop - P - butyl has no food - handling uses which are being proposed. 860.1480 Meat, Milk, Poultry, and Eggs Residue Chemistry Memo, DP No. D 348246 , 0 9 /1 6 /20 0 8 , D. Soderberg ( PP#7F7289 Residue Chemistry Chapter) Inevaluating the data pro vided to support this petition, the establishment of tolerance limits will be recommended for several RACs commonly recognized for use as livestock feedstuffs. This would include establish ing tolerance limits for citrus dried pulp and sugar beet tops whic h are requested in part with this action . The maximum theoretical dietary burdens to livestock were previously evaluated in the prior residue chemistry chapter prepared to support pending uses on dry beans and peanuts (DP No. D348246, D. Soderberg, 09/16/ 2008). The resulting theoretical dietary burdens ofF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 13 of 31 fluazifop - P - butyl to livestock were put forward with the updated version of Table 1 (Table 1 Feedstuffs June 2008) and are presented below in Table 5 for review. Table 5. Calculation of Dietary Burden s of Fluazifop - P - butyl Residues to Livestock. Feedstuff Ty pe 1 % Dry Matter2 % Diet2 Recommended Tolerance (ppm) Dietary Contribution

(ppm) 3 Beef Cattle Soybean, hulls R 90 20 2.5 0.555 Untreated CC CC NA 65 NA 0 Soybean, meal PC 92 15 2.5 0.408 TOTAL BURDEN -- -- -- 0.963 Dairy Cattle Soybean, hulls R 90 15 2.5 0.417 Untreated R R NA 30 NA 0 Carrot, culls CC 12 10 2.0 1.667 Untreated CC CC NA 35 NA 0 Soybean, seed PC 89 15 2.5 0.421 TOTAL BURDEN -- -- -- 2.505 Poultry Untreated CC CC NA 75 NA 0 Soybean, meal PC -- 25 2.5 0.625 TOTAL BURDEN -- -- -- 0.625 Swine Untreated CC CC NA 85 NA 0 Soybean, meal PC -- 15 2.5 0.375 TOTAL BURDEN -- -- 0.375 1 R: Roughage; CC: Carbohydrate concentrate; PC: Protein concentrate. 2 OPPTS 860.10 00 Table 1 Feedstuffs (June 2008). 3 Contribution = ([tolerance /% DM] X % diet) for beef and dairy cattle; contribution = ([tolerance] X % diet) for poultry and swine. 4 N/A: Not applicable. Tolerances/uses of Fluazifop - P - butyl have not been regist ered or proposed for this feedstuff. These calculations are considered tentative because plant and animal metabolism studies remain outstanding and additional field trials are required for some crops. It was also noted that there are label restrictions against the grazing or harvesting of peanut hay as well as soy bean forage and hay which are appropriate according to Table 1 of 860.1000. Inall, the addition of the use on peanut d id not affect the theoretical dietary burden of fluazifop residues to live stock. Soy beans were found to have a larger impact and these matrices were incorporated into the previous dietary burden calculations. The effect of use on cowpea forage and hay along with residues on the soy bean aspirated grain fractions will be evaluat ed after these data have been submitted. Prior calculated dietary burden maximums of fluazifop - P - butyl were reported to beef/dairy cattle at 4.49 ppm, 1.00 ppm to poultry , and 0.70 ppm to swine. These differ significantly from the updated values presente d in Table 5 due to the current calculations being based on a “reasonably balanced” diet and the reduction in the diet percentage for carrot culls. Nonetheless, in assessing the new uses pursuant to this petition, sugar beet tops are no longer a c ontrib utor to the dietary

burden of cattle because when updating the Table 1 Feedstuffs it wasF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 14 of 31 removed as being a significant feed item. A lthough in the assessment of prior actions sugar beet tops would have comprised a large portion of the beef and dairy cattl e diet , it is no longer a factor for consideration in the calculation of dietary burden. With regard s to dried pulp citrus , the tolerance of this livestock feed item is being set based on a practical maximum concentration factor of 13 x . In comparing the recommended tolerance level of 0. 40 ppm for this commodity to the 2.5 ppm tolerance level of soy

bean hulls ( roughage component) now in the dietary burden calculation , no increase in the dietary burden to livestock results . Hence, the prior calculation s fo r secondary transfer of fluazifop - P butyl residues to meat, milk, poultry , and eggs remain current. Conclusions : No change in the tolerances of meat, milk, poultry , and eggs is needed at this time. 860.1500 Magnitude of the Residue in Crops DER Refe rences: 47874601.der.doc (banana) 47874602.der.doc (citrus) R062698.tif (MRID 41373705 ) (citrus) 47874603.der.doc ( sugar beet ) 47874604.der.doc (grape) Sy ngenta Crop Protection has submitted field trial data for fluazifop - P - butyl on bananas , citrus, grapes , and sugar beet s . A summary of the residue data is presented in Table 6. Table 6. Summary of Residue Data from Crop Field Trials with Fluazifop - P - Butyl. Crop matrix Total Applic.

Rate (lb ai/A) PHI

(days) Residue Levels (ppm) N M in. Max. HAFT 1 Median Mean Std. Dev. Bananas (proposed use = 1.125 lb ai/A total application rate, 0 - day PHI) Banana, bagged 1.125 0 10 <0.01 <0.01 <0.01 <0.01 <0.01 N/A Banana, unbagged 1.125 0 10 <0.01 <0.01 <0.01 <0.01 <0.01 N/A Citrus (proposed use = 1.125 lb ai/A total application rate, 14 - day PHI) Orange 1.10

– 1.15 12 - 14 14 <0.01 2 <0.01 <0.01 <0.01 <0.01 N/A

1.5 14 5 <0.03 3 <0.03 <0.03 <0.03 <0.03 N/A 2.25 14 5 <0.03 <0.03 <0.03 <0.03 <0.03 N/A Lemon 1.5 14 5 <0.03 <0.03 <0.03 <0.03 <0.03 N/A

2.25 14 5 <0.03 <0.03 <0.03 <0.03 <0.03 N/A Grapefruit 1.1 4 12 - 14 2 <0.01 <0.01 <0.01 <0.01 <0.01 N/A

1.5 14 5 <0.03 <0.03 <0.03 <0.03 <0.03 N/A 2.25 14 5 <0.03 <0.03 <0.03 <0.03 <0.03 N/A Grapes (proposed use = 1.125 lb ai/A total application r ate, 50 - day PHI) Grapes 1.11

– 1.16 49 - 50 24 <0.01 <0.01 <0.01 <0.01 <0.01 N/A Sugar beet s (proposed use = 0.75 lb ai/A total application rate, 90 - day PHI) Sugar beet , top 0.747 - 0.764 89 - 90 24 0.02 1.45 1.01 0.390 0.425 0.277 Sugar beet , root 0.747 - 0.7 64 89 - 90 24 <0.01 0.23 0.215 0.070 0.080 0.051 1 HAFT = Highest average field trial result. 2 LOQ of the GC/MS method used for the quantitation of the sample results noted. 3 LOQ of the 19 F NMR method used for the quantitation of the sample results not ed.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 15 of 31 Banana (MRID No. 47 874601 ) F ive field trials were conducted in/on bagged and unbagged bananas in the United States during the 1999 growing season. The trials were conducted in Zone 3 (1 trial in Florida) and Zone 13 ( 4 trials in Hawaii ). For each trial, three applications of the 2 lb/gal EC formulation of fluazifop - P - butyl were made at a target rate of 0.375 lbs fluazifop - p - butyl/acre for a total seasonal rate of 1.125 lb a.i./acre . All applications were made in spray volumes of 17 to 29 gal/A (GP A) using ground - based equipment. An adjuvant was added to the spray mixture for all applications (non - ionic surfactant or crop oil concentrate). Each test site consisted of a control and treated plot for both bagged and unbagged bananas . Applications we re made by broadcast spray

to the soil at 60, 30, and 0 day s prior to normal harvest. Banana whole fruit samples were collected at the normal harvest which was immediately fo llowing the last application ( PHI of 0 day s ). Residues of fluazifop - p - butyl, f luazifop, and conjugate esters in bananas were determined as total fluazifop using ABC method 45820 - M - 1. This method is a modification of the Zeneca method entitled “Determination of Total Fluazifop in Crops by Gas Chromatography .” The LOQ for total fluazifop residues was set at 0.01 ppm. The method was adequate for data collection based on concurrent method recoveries. Sample storage conditions and durations incurred for this study which support this action are reported in Table 4. No storage stabil ity data have been submitted for bananas specifically . Nonetheless, the stability of fluazifop - P - butyl has been investigated in a wide variety of frozen crop commodities and documented in several prior reports generated by the registrant. These reports s how residues are stable in/on soy

beans, sugar beets, green beans, strawberries, oilseed rape, coffee, cauliflower, onions, potatoes, peanuts, macadamia nuts, tomatoes, endive, and celery for durations of 3 to 28 months. Following three applications of flu azifop - p - butyl at a seasonal target application rate of 1.125 lbs ai/A, residue level s (reported as total fluazifop) were below the L OQ (0.01 ppm) in all bagged and unbagged samples of whole bananas (PHIof 0 day s). Conclusions : The submitted residue data for bananas are adequate in fulfill ing these data requirements. The number and locations of the field trials are in accordance with OPPTS Guideline 860.1500 for bananas . The trials were made to appropriately reflect the proposed maximum seasonal use pattern. Adequate stability data available for other similar crops can be translated to substantiate the storage conditions and durations that were incurred. Based on the LOQ, the best estimate for a tolerance for bananas is 0.01 ppm . Citrus (MRID No. 41373705) A total of fifteen field trials were conducted in the United States during the 1986 growing season in/on oranges (n=5), grapefruit (n=5), and lemons (n=5). For oranges, 5 trials were conducted in Zone 3 ( Florida). For the grapefruit and lemons , 2 trials were conducted in Zone 3 (Florida), 1 trial in Zone 6 (Texas), and 2 trials in Zone 10 (1 trial in California and 1 trial in Arizona). For each trial, two treat ed test plots were established. One plot received three applications of the 2 lb/ga l EC formulation of fluazifop - P - butyl at a target rate of 0. 5 lbs fluazifop - p - butyl/acre fo r a total seasonal rate of 1.5 lb ai/acre. The other plot received three applications of the 2 lb/gal EC formulation of fluazifop - P - butyl at a target rate of 0. 75 l bs fluazifop - P - butyl/acre fo r a total seasonal rate of 2.25 lbF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 16 of 31 ai/acre. The three applications were made at approximate 21 day re - treatment intervals using ground equipment that directed the spray to the ground beneath the trees. C itrus fruit were harves ted 14 d ay s after the last application . The analy tical method used for data collection was I CIPlant Protection Method 82. The method performed extraction with acetonitrile:concentrated HCl to convert residue s to fluazifop . The procedure employed simi lar clean - up steps as those specified in PAM I I method, but final determination using this protocol is made by 19 F NMR analy sis . Residues in citrus were reported as total fluazifop. The LOQ for total fl uazifop residues was set at 0.03 ppm. This method i s adequate for data collection based upon acceptable concurrent recovery data from oranges, grapefruit, and lemons fortified at 0.05 ppm and 1.0 ppm. Sample storage conditions and durations incurred for this study which support this action are reported i n Table 4. Samples of citrus fruit were analy zed within 25 months of harvest. No storage stability data have been submitted for citrus specifically . Nonetheless, the stability of fluazifop - P - butyl has been investigated in a wide variety of frozen crop c ommodities and documented in several prior reports generated by

the registrant. These reports show residues are stable in/on soy beans, sugar beets, green beans, strawberries, oilseed rape, coffee, cauliflower, onions, potatoes, peanuts, macadamia nuts, to matoes, endive, and celery for durations of 3 to 28 months. Following th e applications of fluazifop - p - butyl at a seasonal target application rate of 1. 5 lbs ai/A and at 2.25 lb ai/A , fluazifop - p - butyl residues (reported as total flu azifop) were below the L OQ (0.0 3 ppm) in oranges, grapefruit and lemon (PHI14 day s). Citrus (MRID No. 47874602 ) A total of eight field trials were conducted in the United States during the 2000 growing season in/on oranges (n=7) and grapefruit (n=1). For oranges, 3 trials w ere conducted in Zone 3 ( Florida) , 1 trial in Zone 6 (Texas), and 3 trials in Zone 10 (1 trial in Arizona; 2 trials in California) . For grapefruit, 1 trial was conducted in Zone 3 (Florida). For each trial, three applications of the 2 lb/gal EC formulati on of fluazifop - P - butyl were made at a target rate of 0.375 lbs fluazifop - P - butyl/acre for a total seasonal rate of 1.125 lb ai/acre. Each test site consisted of a untreated control and treated test plot s . The three applications were made by broadcast sp ray

to the orchard soil beneath the trees, 19 to 21 day s apart and citrus fruit were harvested 12 to 14 day s after the last application ( PHIof 12 to 14 day s ) . Applications were made using ground equipment in 19 to 26 gal/A spray volumes with an adjuvant (non - ionic surfactant or crop oil concentrate). Residues of fluazifop - P - butyl and fluazifop - P were extracted by hydroly zing the ester or acid conjugates to fluazifop which are then derivatized to the methyl ester and analy zed by GC/MS. Residues in citrus were reported as total fluazifop. The LOQ for total fluazifop residues was set at 0.01 ppm. This method is adequate for data collection based upon acceptable method validation recovery data in grapes at the 0.01 ppm and 1.0 ppm fortification levels and concurrent recovery data in citrus at the 0.01 ppm fortification level. The average concurrent recovery at the 1.0 ppm fortification level was only 68.4% which is slightly

outside the generally

acceptable range of 70 to 120% . H owever, this is not a conce rn because the 0.01 ppm fortification level more accurately reflects the residue levels in the RAC samples than does the 1.0 ppm fortification level. The samples were stored frozen from collection through analy sis with the storage conditions andF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 17 of 31 durations incurred for this study being reported in Table 4 . The maximum storage interval from sampling to extraction was 71 day s (2.4 months). All sample extracts were analy zed within 1 day

of extraction. No storage stability data have been submitted for citrus specifically . Nonetheless, the stability of fluazifop - P - butyl has been investigated in a wide variety of frozen crop commodities and documented in several prior reports generated by the registrant. These reports show residues are stable in/on soy

beans, sugar beets, green beans, strawberries, oilseed rape, coffee, cauliflower, onions, potatoes, peanuts, macadamia nuts, tomatoes, endive, and celery for durations of 3 to 28 months. Following 3 treatments of fluazifop - p - butyl at the seasonal application rat e of 1.125 lbs ai/A, residue s (reported as total fluazifop) were below the 0.01 ppm LOQ in oranges and grapefruit (12 - 14 day PHI ). Conclusions : By

combining the 1986 and 2000 trials, the submitted data are adequate in fulfill ing the test guideline requirements for citrus . The number and locations of the fie ld trials follow OPPTS Guideline 860.1500 for citrus fruit crop group 10 (12 orange , 6 grapefruit & 5 lemon trials) . The y generally reflect the proposed maximum seasonal use pattern, although the trials made in 1986 (MRID No. 41373705) were performed at a 1.3 x and 2 x greater rate . Adequate stability data available for other similar crops can be translated to substantiate the storage conditions and durations that were incurred. Based on the LOQ, a 0.03 ppm tolerance is estimated for citrus and a revised section F should be submitted specifying this recommend limit . Grapes (MRID No. 47874604) Twelve field trials were conducted on grapes during the 2000 growing season, encompassing Zone 1 (2 trials in NY), 10 (8 trials in CA), and 11 (1 trial in OR and 1 trial in WA). Separate untreated control and treated test plots wer e e stablished at each trial site. At each test location, three b roadcast spray applications of the 2 lb/gal E C formulation of flu azifop - P - butyl were made to the vineyard floor beneath the grape vines at a target application rate of 0.375 lb ai/A/application, for a total target seasonal rate of 1.125 lb ai/A. Applications were made 12 to 15 day s apart in spray volumes of 10 to 30 ga l/A at 9 trial sites and 8 to 10 gal/A at 3 trial sites. Adjuvants (non - ionic surfactant or crop oil concentrate) were used at all the sites and the grapes subsequently harvested at a PHI of 49 - 50 day s. Samples of grapes were analy zed for total fluazi fop residues (fluazifop - P - butyl, fluazifop free and conjugated) using a GC/MS protocol. This procedure is a common moiety method which hydroly

zes any ester or acid conjugates and treats the resulting extract to form the methyl ester of fluazifop so that a total determination can be made. This method is adequate for data collection based upon acceptable method validation and concurrent method recoveries. The validated L OQ was 0.01 ppm for grapes . Sample storage conditions and durations incurred for this study which support this action are reported in Table 4. Samples were stored frozen for a maximum duration of 45 day s (1.5 months) from harvest to analy sis. Samples from all but three sites were extracted within one month of harvest. All sample extract s were analy zed within 1 day

of extraction. No storage stability data have been submitted for grapes specifically . Nonetheless, the stability of fluazifop - P - butyl has been investigated in a wide variety

of frozen crop commodities and documented in severa l prior reports generated by the registrant. These reports show residues are stable in/on soy beans, sugar beets, green beans, strawberries, oilseed rape, coffee, cauliflower, onions, potatoes, peanuts, macadamia nuts, tomatoes, endive, and celery

for durations of 3 to 28 months. Alternately , stability data are not required forF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 18 of 31 samples that are stored frozen for less than 30 day s, which includes the majority of the samples in this study . As such, the available st ability data support the sample storage dur ations/conditions incurred for the crop field trials made on grapes. Residues of total fluazifop were <L OQ (0 . 01 ppm) in/on grapes harvested 49 to 50 day s after the last of three vineyard floor applications of the 2 lb/gal EC formulation at a total rate o f 1.11 to 1.16 lb ai/A/season. Conclusions . The submitted residue data for grapes are adequate in fulfill ing these data requirements . The trials were made to appropriately reflect the proposed maximum seasonal use pattern. Adequate stability data ava ilable for other similar crops can be translated to substantiate the storage conditions and durations that were incurred. Based on the LOQ, the best estimate for a tolerance for grapes is 0.01 ppm . Sugar beet (MRID No. 47874603) Twelve field trials were conducted on sugar beet s during the 2000 growing season, encompassing Zone s 5 (2 trials in MN, 2 trials in ND, and 1 trial in WI ), 7 (1 trial in NE), 8 (1 trial in KS), 9 (1 trial in MT), 10 (2 trials in CA), and 11 (1 trial in ID and 1 trial in WA). Sep arate untreated control and treated test plots were established at each trial site. At each test location, two foliar b roadcast spray applications of the 2 lb/gal E C formulation of fluazifop - P - butyl were made to sugar beet s at a target application rate of 0.375 lb ai/A/application, for a total target seasonal rate of 0.75 lb ai/A. Applications were made at 12 - to 14 - day retreatment interval s in spray volumes of 10 to 30 gal/A at 9 trial sites and 8 to 10 gal/A at the other 3 trial sites. Adjuvants (non - io nic surfactant or crop oil concentrate) were used at all sites and the sugar beet s subsequently harvested at a PHIof 89 to 90 day s. Samples of sugar beet tops and roots were analy zed for total fluazifop residues (fluazifop - P - butyl, fluazifop free and c onjugated) using a GC/MS protocol. This procedure is a common moiety method which hydroly

zes any ester or acid conjugates and treats the resulting extract to form the methyl ester of fluazifop so that a total determination can be made. This method is ade quate for data collection based upon acceptable method validation and concurrent method recoveries. The LOQ was 0.01 ppm for sugar beet tops and roots. Sample storage conditions and durations incurred for this study which support this action are report ed in Table 4. Samples were stored frozen for a maximum of 75 day s (2.5 months) from harvest to analy sis. All sample extracts were analy zed within 2 day s of extraction. The available storage stability data demonstrate that residues of fluazifop are gene rally stable in/on sugar beet roots stored frozen for up to 12 months (MRID No. 00157193) . Storage stability data are also available which demonstrate that residues of fluazifop are stable in/on a wide variety of other crop matrices for 3 to 28 months. T he available storage data support the sample storage durations/conditions incurred for the crop field trials made on sugar beet tops and roots. For the application program tested, samples were harvested 89 to 90 day s after the last of two broadcast foliar applications made with the 2 lb/gal EC formulation at total rates of 0.747 - 0.764 lb ai/A/season. Inaccordance, m aximum residues of total fluazifop were found to be 1.45 ppm in/on sugar beet tops and at 0.2 3 ppm for the roots.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 19 of 31 Conclusions . The submitte d residue data for sugar beet s are adequate in fulfill ing these data requirements. The trials were made to appropriately reflect the proposed maximum seasonal use pattern. Adequate stability data are available for this RAC to substantiate the storage con ditions and durations that were incurred. The residue data for sugar beet s were entered into the Agency ’s tolerance spreadsheet as specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determine an appropriate toleran ce level ( Appendix I ) . The spreadsheet provides a best estimate of a tolerance at 0.25 ppm for sugar beet roots. Inregard to sugar beet tops, no tolerance will be required for this commodity since it is no longer considered to be a significant food or f eed item. A revised Section F should therefore be submitted to include only the HED - recommended tolerance of 0.25 ppm for residues in/on sugar beet roots. 860.1520 Processed Food and Feed DER References: R062698.tif (MRID No. 41373705 ) (citrus) 4 7874605.der.doc (grapes) 47874606.der.doc ( sugar beet s) Sy ngenta Crop Protection has submitted processing studies for fluazifop - P - butyl on citrus, grapes, and sugar beet s. A summary of the processing factors is presented below in Table 7 for review . Table 7. Summary of Processing Factors for Fluazifop - P - Butyl. RAC Processed Commodity Processing Factor Grapes Raisins ≤1x Juice ≤1x Sugar beet s Refined Sugar 0.36x Dried Pulp 3.9x Molasses 14x Citrus (MRID No. 41373705) Ina single citrus (orange) trial conducted in FL during the 1986 growing season using the 2 lb/gal EC formulation of fluazifop - P - butyl . For this test program, three applications were made at the nominal rate of 3.75 lb ai/A/application, for a total s easonal rate of 11.25 lb ai/A (10x the maximum proposed seasonal rate for citrus). Applications were made at 21 day intervals using ground equipment, with the spray directed to the ground beneath and around the trees. Samples of oranges were harvested 14 day s after the last application and processed into chopped peel, dried pulp, molasses, juice, and oil. The analy tical method used for data collection was I CIPlant Protection Method 82. The method performed extraction with acetonitrile:concentrated HCl to convert residues to fluazifop. The procedure employed similar clean - up steps as those specified in PAM I I method, but final determination using this protocol is made by 19 F NMR analy sis. Residues in citrus are reported as total fluazifop. The LOQ for total fl uazifop residues was set at 0.03 ppm. This method is adequate for d ata collection based upon acceptable concurrent recoveries from the matrices fortified at 0.05 ppm. Sample storage conditions and durations incurred for this study which support this action are reported in Table 4.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 20 of 31 Samples of citrus fruit were analy zed within 25 months of harvest. No storage stability data have been submitted for citrus specifically . Nonetheless, the stability of fluazifop - P - butyl has been investigated in a w ide variety of frozen crop commodities and documented in several prior reports generated by

the registrant. These reports show residues are stable in/on soy beans, sugar beets, green beans, strawberries, oilseed rape, coffee, cauliflower, onions, potatoes, peanuts, macadamia nuts, tomatoes, endive, and celery for durations of 3 to 28 months. Total fluazifop residues were <L OQ (0.03 ppm) in/on the whole oranges treated with fluazifop - P butyl at a total of 11.25 lb ai/A. Following processing of the whole o ranges, total fluazifop residues were 1.7 ppm in chopped peel, 2.6 ppm in dried pulp, 0.09 ppm in molasses and oil, and <L OQ (0.03 ppm) in juice. Based on th ese data, processing factors would be 87x in dried pulp, 3x in oil, and <1x in juice. However, th e Petitioner states that processing factor in dried pulp i s unreasonable considering that oranges contain about 86% water. Therefore, the Petitioner calculated processing factors by assuming that the residue in the whole oranges was 0.65 ppm, as calculate d from the total residue found in the processed commodities and the weight of the starting oranges. The resulting reported processing factors were 4x for dried pulp, 2.6x for peel, 1.7x for molasses, and 0.14x for oil. Conclusions : EPA previously conclu ded that proposed tolerances in citrus fruit and dried citrus cannot be determined (DEB No. 6343, M. J. Bradley , 08/15/1990) . Rather then attempting to upgrade these results, it would be prudent for the petitioner to provide a new study given the age of this data submission. To satisfy

the establishment of tolerances for the citrus processed commodities, the theoretical concentration factors are therefore used for setting the pertinent limits on juice (2x) and oil (1000x). These factors along with the ci trus HAFT of 0.03 ppm, determine that an appropriate fluazifop - P - butyl tolerance for citrus juice would be 0.06 ppm and 30.0 ppm for the oil fraction. In regard to citrus dried pulp, there is no theoretical concentration factor determined for this process ed commodity . Nonetheless, in a recent action made for chlorantraniliprole, a snap - shot of 27 pesticides having citrus dried pulp limits was made to determine a practical maximum concentration factor for this processed commodity (DP No. D361791, D. Rate, 01/08/2010). This determination found that concentration factors range between 2 - 13x for the citrus dried pulp tolerances which were examined. Therefore, using the maximum concentration factor of 13x for fluazifop along with the citrus HAFT of 0.03 ppm , a resulting tolerance of 0.40 ppm should be set for the citrus dried pulp processed commodity . Grapes (MRID No. 47874605 ) A single field trial was conducted during the 2000 growing season on grapes , encompassing Zone 1 0 (1 trial in CA). Separate untr eated control and treated test plots were established at the trial site. Three b roadcast spray

applications of the 2 lb/gal EC formulation of fluazifop - P - butyl were made to the vineyard floor beneath the grape vines to conduct this trial. Treatments were made at a target application rate of 1.875 lb ai/A/application, with a 14 - day retreatment interval (RTI), for a total target seasonal rate of 5.6 3 lb ai/A (5 x the maximum application rate). Grapes were harvested 50 day s after final treatment. The grape RACs were processed into grape juice and raisins. Samples of the grape RAC and its processed commodities were analy zed for total fluazifop residues (fluazifop - P - butyl, fluazifop free and conjugated) using a GC/MS protocol. This procedure is aF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 21 of 31 common moie ty

method which hydroly

zes any ester or acid conjugates and treats the resulting extract to form the methyl ester of fluazifop so that a total determination can be made. This method is adequate for data collection based upon acceptable method validation a nd concurrent method recoveries. The LOQ was 0.01 ppm for all grape matrices. Sample storage conditions and durations incurred for this study which support this action are reported in Table 4. Samples were stored frozen from harvest to extraction for up to 36 day s (1.2 months) for grapes, 29 day s (1 month) for grape juice, and 43 day s (1.4 months) for raisins. The storage duration between processing and extraction was 33 day s for grapes, 26 day s for grape juice, and 30 day s for raisins. Samples were analy zed within 0 - 2 day s of extraction . No storage stability data have been submitted for grapes specifically . Nonetheless, the stability of fluazifop - P - butyl has been investigated in a wide variety

of frozen crop commodities and documented in several pri or reports generated by the registrant. These reports show residues are stable in/on soy beans, sugar beets, green beans, strawberries, oilseed rape, coffee, cauliflower, onions, potatoes, peanuts, macadamia nuts, tomatoes, endive, and celery

for durations of 3 to 28 months. Total fluazifop residues were found to be <L OQ (0.01 ppm) in/on the grape RAC harvested 50 day s after the last of three treatments made at a 5 x seasonal application rate (5.64 lb ai/A/season). Total fluazifop residues were also found to be <L OQ (0.01 ppm) in/on the grape juice and raisin processed grape fractions. As such, the observed processing factors for grape juice and raisins are less than the theoretical concentration factor of 4.7x for raisins (based on the loss of water on pr ocessing grapes into raisins ; OPPTS 860.1520, Table 1) and 1.2x for grape juice (based on separation of components; OPPTS 860.1520, Table 3). Conclusions : The grape p rocessing data are adequate in fulfilling these data requirements. The se data indicate that total fluazifop residues do not appear to concentrate in raisins or grape juice. As a result, n o tolerance is therefore needed for raisins or grape juice. Sugar beet s (MRID No. 47874606) A single field trial was conducted on sugar beet s during the 2000 growing season, encompassing Zone 11 (1 trial in WA). Separate untreated control and treated test plots were established at the trial site. Two foliar b roadcast spray applications using the 2 lb/gal EC formulation of fluazifop - P - butyl were made to sugar beet s to conduct this trial. Treatments were made at a target application rate of 1.875 lb ai/A/application, with a 14 - day RTI , for a total target seasonal rate of 3.75 lb ai/A (5 x the maximum application rate). Sugar beet s were harvested 90 day s a fter final treatment. The sugar beet RAC was processed into refined sugar, dry pulp and molasses. Samples of the sugar beet RAC and its processed commodities were analy zed for total fluazifop residues (fluazifop - P - butyl, fluazifop free and conjugated) us ing a GC/MS protocol. This procedure is a common moiety

method which hydroly

zes any ester or acid conjugates and treats the resulting extract to form the methyl ester of fluazifop so that a total determination can be made. This method is adequate for dat a collection based upon acceptable method validation and concurrent method recoveries. The validated LOQ was 0.01 ppm for all sugar beet matrices. Sample storage conditions and durations incurred for this study which support this action are reported in Table 4. Samples were stored frozen from harvest to extraction for 48 day s (1.6 months) for sugarF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 22 of 31 beet roots, and dry

pulp, 48 to 51 day s (1.6 to 1.7 months) for molasses, and 53 day s (1.8 months) for refined sugar. The storage duration between processi ng and extraction was 28 to 31 day s for molasses, 32 day s for sugar beet roots , 32 to 33 day s for dry pulp, and 33 day s for refined sugar. Samples were analy

zed on the day

of extraction. Storage stability data demonstrate that residues of fluazifop are ge nerally

stable in/on sugar beet roots stored frozen for up to 12 months (MRID No. 00157193) . Although no s torage stability studies are available for the sugar beet processed fractions of sugar beet s, no data are required since extract ion/analy sis occurred within approximately 30 day s from processing. Average total fluazifop residues were found to be 0.86 ppm in/on the sugar beet RAC (root) harvested 90 day s after the last of two broadcast foliar treatments made at a 5x seasonal application rate (3.79 lb ai/A/season). Inprocessed sugar beet fractions, average total fluazifop residues were found to be 0.31 ppm in refined sugar, 3.35 ppm in the dry pulp, and 1 2 ppm in molasses. A comparison of the residues in the RAC with those in each processed fraction resulted in concentration factors of 0.36x for refined sugar, 3.9x for dry pulp, and 14x for molasses. These concentration factors are consistent with the theoretical concentration factor of 12.5x for sugar (based on separation of components; OPPTS 860.15 20, Table 3) and the maximum observed concentration factor of 20x (OPPTS 860.1520, Table 4) for dry pulp and molasses. Conclusions : The sugar beet processing data are adequate in fulfilling these data requirements. The se data indicate that total fluazif op residues do not appear to concentrate in sugar beet refined sugar, but may

concentrate in sugar beet dried pulp and sugar beet molasses. Based on the sugar beet root HAFT (0.22 ppm) and the average processing factor for dried pulp (3.9x) and molasses ( 14x), expected residues in these fractions are 0.86 ppm and 3. 1 ppm , respectively . L ikewise, n o tolerance is needed for the sugar beet refined sugar processed commodity . As a result , the proposed tolerances of 1.0 ppm in dried pulp and 3.5 ppm for molass es are adequate for these sugar beet processed commodities. 860.1650 Submittal of Analytical Reference Standards Analy tical standards for fluazifop - P - butyl and fluazifop - P ( resolved (R) isomer of fluazifop acid) are currently availa ble in the EPA National Pesticide Standards Repository . The fluazifop - P - butyl standard expires 1/1/2011 . Analy tical reference standard s must be replenished as requested by the Repository . The reference standards should be sent to the Analy tical Chemistr

y Lab, which is located 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.)F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 23 of 31 860.1850 /860.1900 Confined and Field Accumulation in Rotational Crops The following plantback restriction exists on the product label (EPA Reg. No. 100 - 1070): a 60 - day plant back interval for rotational crops such as corn, sorghum, and cereals. Th is plantback interval is also appropriate for sugar beet. 860.1550 Proposed Tolerances Ina meeting on March 3, 2004, the MARC concluded that for tolerance e xpression, parent and fluazifop - acid (free and conjugated) are the residues of concern since they are adequate to determine misuse (DP No. D298939, S. L . Kinard, 06/22/2004). An acceptable soy bean metabolism study

is available along with new studies made to a root crop and leafy vegetable which are currently undergoing Agency

review. Inaccordance, t olerances are established under 40 CFR §180.411(a)(1) and (c)(1) for residues of fluazifop - butyl, including free and conjugated fluazifop, expressed as fluazi fop . F or fluazifop - P - butyl , including free and conjugated fluazifop (R isomer), tolerances are likewise established under 40 CFR §180.411(a)(2) and (c)(2) with residues e xpressed as fluazifop . It s registered uses include dry beans, carrot, cotton, endive (escarole) , macadamia nut, onion, peanut, pecan, soy

bean, spinach, stone fruit, and sweet potato . It also carries tolerances with regional registrations on asparagus, coffee, pepper, and rhubarb along with being registered for use on lawns as a weed control application. For this action , field trials on bananas, citrus, grapes, and sugar beet s along with corresponding studies made on the pertinent processed commodities were submitted to support this petition request. Inevaluating the field trials provid ed by the registrant , these studies were found to be adequate in satisfying these residue chemistry data requirements. Inregard to the banana, grape, and citrus RACs, residues levels in all of the treated samples analy zed were found to be below the LOQ o f the test method. As such, the proposed tolerance of 0.01 ppm specified by the registrant for bananas and grapes is acceptable. Following this approach a revised tolerance of 0.03 ppm for citrus based upon the corresponding LOQ of the test method is the refore recommended instead of the 0.05 ppm level proposed by

the registrant. Total fluazifop residues in/on sugar beet RACs were found to be readily quantifiable at levels greater then the L OQ of the test method. Inaccordance, the Agency ’s Guidance for Setting Pesticide Tolerances Based on Field Trial Data was utilized for determining appropriate tolerance levels for sugar beet roots ( Appendix I ) . Based on these calculations, the proposed sugar beet tolerance of 0.25 in roots is adequate . Inevaluating of the corresponding processing study data that were provided, it can be concluded that no additional tolerances are needed for grape juice and raisins as well as sugar beet refined sugar. However , residues of fluazifop were found to concentrate in sugar beet dry pulp (3.9x) and sugar beet molasses (14x). Based on the sugar beet root HAFT of 0.22 ppm and the processing factor s calculated for dried pulp and molasses, expected residues in these fractions are 0.86 ppm and 3. 1 ppm , r espectively . As a result , the tolerances of 1.0 ppm in dried pulp and 3.5 ppm for molasses proposed by

the registrant are adequate for these sugar beet processed commodities. For the citrus processed commodities , the p etitioner has also proposed tolerances of 0.40 ppm in dried pulp along with 0.05 ppm in juice and oil. However, EPA previously concluded that proposed tolerances in citrus fruit and dried citrus cannot be determined (DEB No. 6343, M. J. Bradley , 08/15/1990). Rather then attempting to upgrade these results, it wo uld be prudent for the petitioner toF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 24 of 31 provide a new study

given the age of this data submission. To satisfy the establishment of tolerances for the citrus processed commodities, the theoretical concentration factors are therefore used for setting the perti nent limits on juice (2x) and oil (1000x). These factors along with the citrus HAFT of 0.03 ppm, determine that an appropriate fluazifop - P - butyl tolerance for citrus juice would be 0.06 ppm and 30.0 ppm for the oil fraction. In regard to citrus dried pulp, there is no theoretical concentration factor determined for this processed commodity . Using a practical maximum concentration factor of 13x as identified in a recent chlorantraniliprole action , along with the citrus HAFT of 0.03 ppm, a fluazifop - P - butyl tolerance of 0.40 ppm for citrus, dried pulp is appropriate. The current petition requests the establishment of tolerances on dried pulp citrus and sugar beet tops, commodities which have been considered livestock feedstuffs. Following revision of the Table 1 Feedstuffs in 2008, sugar beet tops were removed as being a significant feed item, and thus it no longer contributes to the dietary burden of cattle. The potential contribution of citrus dried pulp to the livestock dietary

burden was considered b y assuming a concentration factor of 13x and comparing the resulting residue contribution to that of soy bean hulls, the current roughage component in the dietary burden calculation. Since soy bean hulls has a higher tolerance than the recommended tolerance level of dried pulp citrus, the current tolerances on meat, milk, poultry , and eggs are considered adequate and should remain unchanged. This conclusion should be re - examined upon receipt of the requested processing study

for citrus. The establish ed tolerances for livestock commodities are 0.05 ppm for total fluazifop residues in milk and the meat and meat by products of cattle, goat, hog, horse, and sheep, and fat, meat and meat by products of poultry . These levels remain appropriate . T he availab le residue data provided for fluazifop - P - butyl are adequate to support the establishment of new permanent tolerance levels recommended for the RACs proposed in this action . There are no Codex, Canadian or Mexican established M aximum R esidue L imits (MRL s) for residues of fluazifop P - butyl in/on bananas, citrus, grapes and sugar beet s. As a result, international harmonization is not an issue for this data evaluation concerning any of these crops. The proposed tolerances should therefore be revised and a ne w Section F submitted to reflect the recommended tolerance levels and correct commodity

definitions specified below in Table 8 . Table 8. Tolerance Summary for Fluazifop - P - butyl. Commodity Established Tolerance (ppm) Proposed

Tolerance (ppm) Recommended

Tolerance (ppm) Comments; Correct Commodity Definition Tolerances Proposed for 40 CFR §180.411(a)(1) Banana -- 0.01 0.01 Citrus -- 0.05 0.03 Fruit, citrus, group 10 - 10 Citrus, oil -- 0.05 30.0 Citrus, dried pulp -- 0.40 0. 40 Citrus, juice -- 0.05 0.06 Grapes -- 0.01 0.01 Beet, sugar, root -- 0.25 0.25 Beet, sugar, top -- 1.5 None Removed from Table 1 Feedstuffs, June 2008 Beet, sugar, dried pulp -- 1.0 1.0 Beet, sugar, molasses -- 3.5 3. 5F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 25 of 31 References DP No.: D 319907 Subject: Fluazifop - P - butyl. REVI SED TRED

– Report on FQPA Tolerance Reassessment

Progress and Interim Risk Management Decisions. Residue Chemistry Considerations. Case No. 2285. From: S. L . Kinard To: D. L ocke Dated: 08/17/2005 MRID Nos.: 00093840 - 1, 00093843, 00093845 , 00137763, 00144014, 00151494, 00157191,

001517193, 40140401, 40241901, 40341601, 40361104, 40361108, 40361111, 40693108, 40725701, 40831303 - 5, 40831307, 40831309 - 10, 41018001, 41373703. DP No.: D298939 Subject: Fluazifop - P - butyl. Report of the Metabol ism Assessment Review Committee. From: S. L . Kinard To: Y. Donovan Dated: 03/17/2004 MRIDs: None DP No.: None Subject: PP#0F3842/FAP#0H5596. Fluazifop - P - butyl on Citrus. Evaluation of Analy tical Methods and Residue Data. MRID Nos. 41373701 - 06. DE B No. 6343. Hed Project No. 0 - 0683. From: M. J. Bradley To: J. Miller Dated: 08/15/1990 MRID Nos.: 41373701 - 41373706. DP No.: D361791 Subject: Chlorantraniliprole. Amended Section 3 Registration Request for Uses on Various

Field, Vegetable, and Fr

uit Crops and Discussion of Future Registration and Tolerance Requests. Summary

of Analy tical Chemistry

and Residue Data. From: D. Rate To: V. Eagle and K. Davis Dated: 01/08/2010 MRID Nos.: 47588201 - 11 and 47588214 - 29F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 26 of 31 DP No.: D348246 Subject: Fluaz ifop - P - Butyl. Section 3 Registration Request to Add New Uses on Beans (Dry ), Peanuts and Soy

beans. Summary

of Analy tical Chemistry

and Residue Data. From: D. Soderberg To: J. Miller Dated: 9/16/2008 MRID Nos.: 47285501 - 05; 46412503

MRID No.: 00157193 Atreya, N. C. and Froggatt, D. A. (1983) Reside Data Report No.

PP009B157 Storage Stability Study ; Sugar beet, Strawberries, Oilseed Rape, Green Beans and Cauliflower. Study Number: PP009BC04. Unpublished study prepared by Imperial Chemical Industries PL C Plant Protection Division. 22 pages. Attachments: International Residue L imit Status sheet Appendix I - Tolerance Assessment Calculations Tem plate Version September 2005F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 27 of 31 

### International Residue Limits

Fluazifop - P - butyl ( 12 2809 ; 08/26/2010) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 Codex 3

40 CFR 180. 411 : Plant/Livestock : butyl(R) - 2 - [4 - [[5 - (trif luoromethyl) - 2 - p yridinyl]oxy]phenoxy]propanoate, and the free and conjugated forms of the resolved isomer of fluazifop, (R) - 2 - [4 - [[5 -

(trif luoromethyl) - 2 - pyridinyl]oxy]phenoxy]propanoic acid, expressed as fluazifop. butyl ( RS ) - 2 - [4 - [[5 - (trifluoromethyl - 2 - py ridinyl]oxy]phenoxy] propanoate (calculated as acid) None

C ommodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex Banana 0 .0 1 None None Fruit, citrus, crop group 10 0.03 Citrus, dried pulp 0. 40 Citrus, juice 0.06 Citrus, oil 30.0 Grapes 0.01 Beet, sugar, root 0.25 Beet, sugar, dried pulp 1.0 Beet, sugar, molasses 3.5

Completed: M. Negussie/08/30/2010 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 US tolerances and/or Codex MRLs for its export purposes. 3 * = absent at the limit of quantitation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed postharvest treated commodity, such as processing of treated stored wheat. (fat) = to be measured on the fat portion of the sample. MRLs indicated as proposed have not been finalized by the CCPR and the CAC.F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 28 of 31 Appendix I Tolerance Assessment Calculations For each of the crop s listed below, the Guidance for Setting Pesticide Tolerances Based on Field Trial Data ( SOP ) , along with the tolerance spreadsheet (January 2008 version) , was used for calculating recomm ended tolerances. Sugar beet , Root The dataset used to establish a tolerance for fl uazifop - P - butyl on sugar beet root consisted of field trial data representing seasonal application rates of 0.747 - 0.764 lb ai/A ( two applications at a target of 0.375 lb ai/A) with a 89 - to 90 - day PHI . As specified by

the Guidance for Sett ing Pesticide Tolerances Based on Field Trial Data SOP, the field trial application rates and PHI s are within 25% of the maximum label application rate and minimum label PHI , respectively . The residue values used to calculate the tolerance are provided in Table I - 2. Samples from 11 of the 12 field trials were above the L OQ (LOQ = 0.01 ppm). Residues l ess than the LOQ were assigned values of 0.01 ppm. The fluazifop - P - butyl - sugar beet root dataset was entered into the tolerance spreadsheet. The result from the approximate Shapiro - Francia test statistic (Figure I - 6) indicated that the assumption of log normality should be rejected. Visual inspection of the lognormal probability plot ( Figure I - 3) provided in the spreadsheet confirmed that the dataset is not lognormal. Since the field trial data for fluazifop - P - butyl on sugar beet roots are not lognormal, the mean plus 3 standard deviations should be selected as the tolerance value. Us ing the rounding procedure as outlined in the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP, the mean plus 3SD rounds to the value 0.25 ppm (Figure I - 4). Therefore, 0.25 ppm is the recommended tolerance level for fluazifop - P - butyl on sugar beet roots .F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 29 of 31 Table I - 1. Residue data used to calculate tolerance for fl uazifop - P - butyl on sugar beet root . Regulator: EPA Chemical: Fluazifop - p - butyl Crop: Sugar beet root PHI: 89 - 90 Days App. Rate: 0.747 - 0.764 Submitter: Syng enta Crop Protection, Inc. Residues LN(Residues) Z - scores 0.06 - 2.81 - 0.48 0.05 - 3.00 - 0.88 0.09 - 2.41 0.48 0.1 - 2.30 0.60 0.08 - 2.53 0.16 0.07 - 2.66 - 0.26 0.05 - 3.00 - 0.73 0.07 - 2.66 - 0.16 0.06 - 2.81 - 0.37 0.07 - 2.66 - 0.05 0.1 - 2. 30 0.73 0.11 - 2.21 0.88 0.01 - 4.61 - 1.95 0.01 - 4.61 - 1.50 0.08 - 2.53 0.26 0.08 - 2.53 0.37 0.02 - 3.91 - 1.24 0.03 - 3.51 - 1.04 0.05 - 3.00 - 0.60 0.07 - 2.66 0.05 0.11 - 2.21 1.04 0.11 - 2.21 1.24 0.2 - 1.61 1.50 0.23 - 1.47 1.95F luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 30 of 31 Figure I - 3. Lognorm al probability plot of fluazifop - P - butyl fi eld trial data for sugar beet root .

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 1.0000 0.5000 0.2500 0.1250 0.0625 0.0313 0.0156 0.0078 y = 0.7436x - 2.7571 R2 = 0.8814Concentrations

Percentiles Log nor ma l P ro

bab il ity

P lotF luazifop - P - butyl Summary of Analytical Chemistry and Residue Data DP No. 385205

Page 31 of 31 Figure I - 4. Tolerance spreadsheet sum ma ry of fluazifop - P - butyl field trial data for sugar beet root .

Regulator: EPA Chemical: Fluazifop - p - butyl Cro p: Sugar beet root PHI: 89 - 90 Days App. Rate: 0.747 - 0.764 Submitter: Syngenta Crop Protection, Inc. n: 24 min: 0.01 max: 0.23 median: 0.07 average: 0.08 95th Percentile 99th Percentile 99.9th Percentile EU Me thod I Normal 0.20 0.20 0.25 (0.20) (0.25) ( -- ) 95/99 Rule 0.25 0.40 0.70 (0.40) (0.80) ( -- ) EU Method II Distribution Free 0.20 Mean+3SD 0.25 UCLMedian95th 0.40 Approximate Shapiro - Francia Normality Test Statistic 0.8814 0.05 >= p - value > 0.01 : Reject lognormality

assumption