UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

OFFICE OF CHEMICAL SAFETY AND POLLUTION PRE VENT ION



### MEMORAND UM

Date:

Subject:

From:

Through:

To: 12-D ece mber-20 13

Flutolanil. Petition for Amendments to Section 3 Uses of Flutolanil on 

### Brassica ( Co le) Leafy Vegetables (Crop Group 5), Turnip Greens, Pean uts, and Rice. Summary of Ana lytical Chemistr y a nd Residue D ata.

PC C ode : 128975 Decision No.: 480092 Petitio n No.: NA Risk Assess ment Type: NA TXRNo.: NA MRID No.: See Below DP Barcode: D4 1 3582 Registration No. : 71 711-28 Regulatory Action: Section 3 Registration CaseNo.: NA CAS No.: 66332-96-5 40 CFR : § 180.484

Nancy Dodd

, Chemist

### :;/'~**~/ ~**  Risk Assessment Branch III v/ Healt h Effects Division ( 750 9P)

Steve Funk, Senior Ch emist 

# J !

. Q

. Risk Assessment Branch III

### i~ Health Effec ts Di vision (7509P

Wi lliam Cutchin/Eri n Malone, RM#20 Registrat ion Division (7505P)

Page 1 of36Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 2 of 36 Table of Contents

1.0 Executive Summary ............................................................................................................ 4

2.0 Regulatory Recommendations ............................................................................................ 7

2.1 Data Deficiencies/Data Needs .......................................................................................... 7

2.2 Tolerance Considerations ................................................................................................. 7

2.2.1 Enforcement Analytical Method ............................................................................... 7

2.2.2 Recommended Tolerances ........................................................................................ 8

2.2.3 Revisions to Petitione d-For Tolerances .................................................................... 8

2.2.4 International Harmonization ..................................................................................... 9

3.0 Introduction .................................................................................................................. ....... 9

3.1 Chemical Identity ............................................................................................................. 9

3.2 Physical/Chemical Characteristics ................................................................................. 10

3.3 Pesticide Use Pattern/Direct ions for Use (860.1200) ..................................................... 11

4.0 Metabolite/Degradate Residue Profile .............................................................................. 14

4.1 Nature of the Residue ..................................................................................................... 14

4.1.1 Summary of Plant Metabolism (860.1300) ............................................................. 14

4.1.2 Summary of Livestock Metabolism (860.1300) ..................................................... 14

4.1.3 Summary of Confined Rotational Crops (860.l850) ............................................... 15

4.1.4 Summary of Metabolites and Degradates ............................................................... 15

4.2 Comparison of Metabolic Pathways .............................................................................. 15

4.3 Residues of Concern Summary and Rationale ............................................................... 16

5.0 Residue Profile ............................................................................................................... ... 16

5.1 Residue Analytical Methods (860.1340) ........................................................................ 16

5.1.1 Data Collection Methods ........................................................................................ 16

5.1.2 Multi-Residue Methods (860.1360) ........................................................................ 17

5.1.3 Tolerance Enforcement Methods ............................................................................ 17

5.1.4 Submittal of Analytical Reference Standards (860.1650) ...................................... 18

5.2 Storage Stability (860.1380) .......................................................................................... 19

5.3 Residue Data .................................................................................................................. 20

5.3.1 Crop Field Trials (860.1500) .................................................................................. 20

5.3.2 Field Rotational Crops (860.1900) ......................................................................... 24

5.3.3 Processed Food and Feed (860.1520) ..................................................................... 25

5.3.4 Meat, Milk, Poultry and Eggs (860.1480) .............................................................. 25Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 3 of 36 5.3.5 Food Handling (860.1460) ...................................................................................... 27

5.3.6 Water, Fish, and Irrigated Crops (860.1400) .......................................................... 27

5.4 Food Residue Profile ...................................................................................................... 27

6.0 Tolerance Derivation ........................................................................................................ 2 8 Appendix A. Chemical Names and Structures ............................................................................ 31 Appendix B. Field Trial Geographic Distribution ....................................................................... 33 Appendix C. International Residue Limits Table ........................................................................ 34 Appendix D. OECD MRL Calculat ion Procedure Inputs/Outputs .............................................. 35Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 4 of 36 1.0 Executive Summary

Introduction . Flutolanil [ N -[3-(1-methylethoxy)phenyl]-2-(tri fluoromethyl)benzamide] is a systemic benzanilide fungicide with preventative and curative actions.

Permanent tolerances have been established under 40 CFR §180.484(a) for residues of flutolanil, including its metabolites and degr adates, in or on cotton, peanuts, potatoes, rice, soybeans, turnip greens, the Brassica leafy vegetables crop group 5, and lives tock commodities. Tolerances for indirect or inadvertent residues have been established under 40 CFR §180.484(d) for wheat commodities. Compliance with the tolerance le vels is to be determined by measuring only flutolanil and its metabolites converted to 2- (trifluoromethyl)benzoic acid and calculated as flutolanil.

Proposed Use . Nichino America, Inc. has proposed 1) adding a banded application to the existing broadcast use for peanuts on the susp ension concentrate (SC) label; 2) adding the Brassica (cole) leafy vegetables crop gr oup and turnip greens to the SC label using dry flowable (DF) residue data; 3) slightly modifyi ng the established SC use rate on rice.

Nature of the Residue

Plants. The nature of the residue in plan ts is adequately understood based on acceptable metabolism studies submitted previously on rice, cucumber leaves, and peanuts. The parent compound and metabolites containing the common moiety, 2-(trifluoromethyl)benzanilide, are the residues of concern which need to be includ ed in the tolerance expression and dietary risk assessment. The enforcement method convert s parent and metabolite s containing the common moiety 2-(trifluoromethyl)benzanilide to 2-(trifluoromethyl)benzoic acid.

Livestock. The nature of the residue in livestock is adequately understood based on acceptable metabolism studies in goats and poultry. The parent compound and metabolites containing the common moiety, 2-(trifluoromethyl)benzanilide, are the residues of concern which need to be included in the tolerance expression and dietar y risk assessment. The enforcement method converts parent and metabolites containing the common moiety 2-(trifluor omethyl)benzanilide to 2-(trifluoromethyl)benzoic acid.

Rotational Crops. The nature of the residue in rotational crop commodities is adequately understood based on an acceptable confined rota tional crop study with lettuce, radish, and oat/sorghum conducted with [U- 14 C-aminophenoxy]flutolanil. The residues of concern for the tolerance expression and dietary risk assessm ent for rotational crops are flutolanil and metabolites containing the common moiety, 2-(tri fluoromethyl)benzanilide, which is converted by the enforcement method to 2- (trifluoromethyl)benzoic acid.

Enforcement Methods : Adequate enforcement methods ar e available. A gas chromatographymass spectrometry (GC/MS) enforcement method ( AU/95R/04) analyzes the flutolanil residues of concern in plants and livestock commodities fo r the tolerance expression and risk assessment. The method is available in MRID 44526201, entitled Validation of an Analytical Method for Residues of Flutolanil in Milk, Peanuts, and Rice . The method has undergone a successfulFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 5 of 36 independent validation with pea nut nutmeat and hay, rice grain, milk, eggs, beef muscle, and beef fat. The AU/95R/04 analytical method dete rmines all metabolites co nverted to the common moiety 2-(trifluoromethy l)benzoic acid (2-TFBA), including flutolanil, M-2, M-3, M-4, and M-7. (For chemical names and structures, refer to Appendix A.) The limits of quantitation (LOQs) are 0.05 ppm for whole milk and livestock tissues and 0.2 ppm for rice and peanut matrices. Radiovalidation was conducted on peanut vines, hulls, and nutmeats using a similar GC/MS common moiety method (AU/01/94). A confirmato ry method is required because the method AU/95R/04 is a common moiety method. Nich ino America submitted a liquid chromatographytandem mass spectrometry (LC/MS/MS) method (XAM-65), which is acceptable as a confirmatory enforcement method. Method XAM-65 separately determines residues of flutolanil and its major metabolite, M-4.

Multiresidue Methods . The requirements for multiresidue methods testing have been met. The multiresidue test results were forwarded to FDA.

Crop Field Trials

Brassica (cole) leafy vegetables and turnip greens: The available residue data are adequate to support addition of the proposed uses on Brassica (cole) leafy vegetables and turnip greens to the SC label. The residue data on Brassica were obtained using a DF formulation. The proposed formulation is a suspension concentrate (SC) formul ation. Data can be translated from DF to SC formulations since the PHI is longer th an 7 days [Organization for Economic Cooperation and Development ( OECD ) Guideline for the Testing of Chemicals, Crop Field Trial , September 7, 2009]. Residues in the Brassica leafy vegetables are ge nerally less than the LOQ (<0.05 ppm). However, since detectable re sidues were found in one mustard green sample, HED recommends that the established tole rances of 0.1 ppm on turnip greens and the Brassica leafy vegetables crop group 5 be increased to 0.20 ppm.

Peanuts: The available residue da ta are adequate to add banded a pplication to the SC label. The proposed use rate is the same maximum seasonal ra te as the registered broadcast rate with a longer PHI (90 days instead of 40 days). The av ailable residue data from the wettable powder (WP) and water-dispersible pow der (WG/WDG) formulations can be translated to the SC formulation since the PHI is l onger than 7 days. The geograp hic representation including band and broadcast applications is adequate. Adequa te storage stability data are available. The established tolerance (40 CFR §180. 484) of 0.5 ppm on peanut is adequate. Based on the OECD tolerance calculation procedures , the 15.0 ppm established tolera nce on peanut hay should be increased to 20.0 ppm.

Rice: Use of the Flutolanil 40 SC formul ation on rice was previously reviewed and recommended (D379515, A. Acierto, 10/8/10). HED ha s no objection to the minor rate change proposed for rice on the Flutolanil 40 SC label, i.e., to change th e lowest application rate from 11.8 to 12.0 fl oz/A (0.35-0.36 lb ai/A). The minor label revision does not require any additional residue data review. The established toleran ce (40 CFR §180. 484) of 7.0 ppm on rice grain is adequate.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 6 of 36 Processing Studies : Adequate processing stud ies are available for pea nuts and rice. Residues concentrate in peanut meal (2x) and rice bran (1 .4x) but do not concentrat e in refined peanut oil or polished rice. There are no proc essed commodities associated with Brassica (cole) leafy vegetables or turnip greens.

Storage Stability : Adequate storage stability data are avai lable to support the storage intervals of the field trial residue samples for Brassica (cole) leafy vegetables and turnip greens, peanuts, and rice. The data show that resi dues of flutolanil and M-4 are st able under frozen storage for the storage durations of the samples.

Meat, Milk, Poultry, and Eggs : Tolerances are established fo r residues of flutolanil and its metabolites converted to 2-TFBA in ruminant (ca ttle, goat, horse, and sheep) commodities at 0.05 ppm for milk, 0.10 ppm for fa t, 1.00 ppm for kidney, 2.00 ppm for liver, and 0.05 ppm for meat and meat byproducts, and in poultry commoditi es at 0.05 ppm for egg, fat, meat, and meat byproducts. Feeding studies are available on la ctating cows and laying hens. Based on the feeding studies and the maximum reasonably ba lanced diets for livestock, the established livestock tolerances are adequate.

Rotational Crops : Rotational crop restrictions and inadve rtent residue tolerances have been established on the Flutolanil 40SC label [E PA Reg. No. 71711-28] based on the available confined and field accumulation studies.

Since Brassica (cole) leafy vegetables and turnip greens are being registered on the 40SC label, the rotational crop restrictions for the Flutolanil 40SC [71711-28] label should be amended to include Brassica (cole) leafy vegetables and turnip greens under the 0- day rotational crop restriction interval.

International Tolerances . The tolerance expression in the US is flutolanil, N -(3-(1- methylethoxy)phenyl)-2-(trifluoromethyl)benzamid e, and its metabolites converted to 2- (trifluoromethyl)benzoic acid and calculated as flutolanil. The Codex tolerance expression for plant commodities is flutolanil. The Codex to lerance expression for livestock commodities is flutolanil and its transformation products contai ning the 2-trifluromethyl-benzoic acid moiety, expressed as flutolanil. Thus, the US tolerance expression harmonizes with Codex for livestock commodities but not for plants. There are no Canadian tolerances for flutolanil.

There are no Codex, Canadian, or Mexican maximu m residue limits (MRLs) for peanuts, turnip greens, or the Brassica (cole) leafy vegetables. Codex MRLs are establis hed on rice grain, bran, and straw. Codex and US tolerance levels are the same for rice bran and rice straw. Codex and US tolerance levels for rice grain are different, i.e., 7.0 ppm in the US versus 2 for husked rice grain and 1 for polished rice grain in Codex.

A risk assessment is to be provided.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 7 of 36 2.0 Regulatory Recommendations

Provided the following deficiencies are addre ssed, HED has no objection to the proposed amendments to the Brassica (cole) leafy vegetable group 5, turn ip greens, peanuts, and rice. These amendments will 1) add Brassica (cole) leafy vegetables and turnip greens to the Flutolanil 40 SC label; 2) add band ed application to peanuts to the Flutolanil 40 SC label; and 3) revise the lowest application rate on rice on the Flutolanil 40 SC label from 11.8 to 12.0 fl oz/A.

2.1 Data Deficiencies/Data Needs

Data gaps that need to be addressed prior to a tolerance being established/registration allowed

860.1200 Directions for Use

Since Brassica (cole) leafy vegetables and turnip greens are being registered on the SC label, the rotational crop restric tions for the Flutolanil 40SC label (71711-28) should be amended to include Brassica (cole) leafy vegetables and turnip greens under the 0-day crop restriction interval.

860.1550 Proposed Tolerances

Tolerances are established [ 40 CFR §180. 484(a)] on rice straw a nd hulls. Tolerances on these commodities are no longer required ( Table 1 Feedstuffs , June 2008) and should be removed.

Tolerances are established [40 CFR §180.484(a) ] at 0.1 ppm on turnip greens and the Brassica (cole) leafy vegetables. These tole rances should be increased to 0.20 ppm.

Based on the Organization for Economic Coope ration and Development (OECD) tolerance calculation procedures, the establ ished tolerance of 15.0 ppm on pe anut hay is not adequate; a tolerance of 20.0 ppm should be proposed for peanut hay.

860.1650 Submittal of Analytical Reference Standards

Analytical reference standards for M-2, M-3, M- 4, and M-7 must be sent to the EPA National Pesticide Standards Repository.

2.2 Tolerance Considerations

2.2.1 Enforcement Analytical Method

Adequate enforcement methods are availabl e. A gas chromatography-mass spectrometry (GC/MS) enforcement method (AU/95R/04) analyzes th e flutolanil residues of concern in plants and livestock commodities for the tolerance expression and risk assessment. The method is available in MRID 44526201, entitled Validation of an Analytical Method for Residues of Flutolanil in Milk, Peanuts, and Rice . The method has undergone a successful independentFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 8 of 36 validation with nutmeat, peanut and hay, rice grai n, milk, eggs, beef muscle, and beef fat. The AU/95R/04 analytical method determines all me tabolites converted to the common moiety 2- (trifluoromethyl)benzoic acid (2-TFBA), incl uding flutolanil, M-2, M-3, M-4, and M-7. The limits of quantitation (LOQs) are 0.05 ppm for w hole milk and livestock tissues and 0.2 ppm for rice and peanut matrices. Radiovalidation was conducted on peanut vines, hulls, and nutmeats using a similar GC/MS common moiety method ( AU/01/94). A confirmatory method is required because the method AU/95R/04 is a common moiety method. Nichino America submitted a liquid chromatography-tandem mass spectrometr y (LC/MS/MS) method (XAM-65), which is acceptable as a confirmatory enforcement meth od. Method XAM-65 separately determines residues of flutolanil and its major metabolite, M-4.

2.2.2 Recommended Tolerances

The residue definition (toleran ce expression) in 40 CFR §180.484 has been revised per the S. Knizner memo dated 5/27/09.

Table 2.2.2. Tolerance Summary for Flutolanil. Commodity Established Tolerance (ppm) HED-Recommended Tolerance (ppm) Comments ( correct commodity definition ) Peanut 0.5 0.5 Peanut, hay 15.0 20.0 Peanut, meal 1.0 1.0 Rice, bran 10.0 10.0 Rice, grain 7.0 7.0 Rice, hulls 25.0 Remove Rice, straw 10.0 Remove Turnip, greens 0.1 0.20 Vegetable, brassica, leafy, group 5 0.1 0.20

2.2.3 Revisions to Petitioned-For Tolerances

No tolerance revisions were proposed with the proposed amendments.

Tolerances are established [ 40 CFR §180.484(a)] on rice straw and hulls. Tolerances on these commodities are no longer required ( Table 1 Feedstuffs , June 2008) and should be removed.

Based on the OECD tolerance calcu lation procedure on peanut hay, the established tolerance of 15.0 ppm for peanut hay should be increased to 20.0 ppm.

The tolerance of 0.1 ppm on turnip greens and the Brassica (cole) leafy vege table group 5 should be increased to 0.20 ppm since detectable residue s of parent were found in one field trial on mustard greens.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 9 of 36 2.2.4 International Harmonization

An International Residue Limits (IRL) table is attached (Appendix C).

The US tolerance expression for plant and livest ock commodities is flutolanil and its metabolites converted to 2-(trifluoromethyl)benzoic acid and calculated as flutolanil. The Codex tolerance expression is flutolanil for plants. For animal commodities, the Codex tolerance expression is flutolanil and its transformation products contai ning the 2-(trifluoromethyl )benzoic acid moiety. Thus, the US tolerance expression harmonizes with the Codex tolerance e xpression for livestock commodities but not for plants.

There are no Codex, Canadian, or Mexican MR Ls for peanuts, turnip greens, or the Brassica (cole) leafy vegetables. Codex MRLs are established on rice grain, bran, a nd straw. Codex and US tolerance levels are the same for rice bran an d rice straw. Codex and US tolerance levels for rice grain are different, i.e., 7.0 ppm in the US ve rsus 2 for husked rice grain and 1 for polished rice grain in Codex.

2.3 Label Recommendations

Since Brassica (cole) leafy vegetables and turnip greens are being registered on the SC label, the rotational crop restric tions for the Flutolanil 40SC (EPA Reg. No. 71711-28) label should be amended to include Brassica (cole) leafy vegetables and tu rnip greens under the 0-day crop restriction interval.

3.0 Introduction

Flutolanil, N -[3-(1-methylethoxy)phenyl]-2-(trifluor omethyl)benzamide, is a systemic benzanilide fungicide with both preventative and curative acti ons. Its mode of action is inhibition of mitochondrial resp iration by inhibition of the en zyme succinate dehydrogenase.

3.1 Chemical Identity

The nomenclature of flutolanil is summarized in Table 3.1, and the physicochemical properties are summarized in Table 3.2. The chemical names and structures of flutolanil and its transformation products are presented in Appendix A.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 10 of 36 Table 3.1. Flutolanil Nomenclature

. Compound

Common name flutolanil Company experimental name N/A
IUPAC name α , α , α -trifluoro-3’-isopropoxy- o -toluanilide
CAS name N -[3-(1-methylethoxy)phenyl]-2-(trifluoromethyl)benzamide
CAS # 66332-96-5 End-use product (EP) Flutolanil SC (a suspension concentrate containing 3.8 lb ai/gal; EPA Reg. No. 71711-28) Moncut® 70-DF (a 70% dry flowable formulation; EPA Reg. No. 10163-301)
Chemical structure of common moiety determined by enforcement method

2-(trifluoromethyl)benzoic acid (2-TFBA)

3.2 Physical/Chemical Characteristics

The physicochemical properties are summarized in Table 3.2. The chemical names and structures of flutolanil and its meta bolites are presented in Appendix A.

Table 3.2. Physicochemical Properties of the Technical Grade Flutolanil.
Parameter Value Reference Molecular weight (g/mole) 323.3 Melting point/range 100.4-103.8 °C DP#s 190584 and 190586, 3/24/94, J. Garbus; MRID 42606601

MRID 40342904 pH 5.69 Density (g/cm 3 ) 1.325 @ 20-25 °C Water solubility 6.53 mg/L at 20 °C Solvent solubility (g/L) at 20 °C Acetone 1440 Methanol 232 n-Hexane 0.9 Toluene 57 Ethyl acetate 675 Vapor pressure 4.87 x 10 -8 mm Hg at 25 °C Dissociation constant, pK a Not applicable N H O CH 3

CH 3

O

CF 3

O

CF 3 OHFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 11 of 36 Table 3.2. Physicochemical Properties of the Technical Grade Flutolanil.
Parameter Value Reference Octanol/water partition coefficient, Log(K O W ) log P OW = 3.74

UV/visible absorption spectrum Not available

3.3 Pesticide Use Pattern/Directions for Use (860.1200)

Brassica (Cole) Leafy Vegetable Crop Group 5 and Turnip Greens: The Brassica (cole) leafy vegetable crop group 5 and turnip greens are re gistered by Gowan Company on the Moncut® 70- DF label [EPA Reg. No. 10163-301] but not on th e Nichino America Flutolanil 40SC Fungicide label (EPA Reg. No. 71711-28). The registered and proposed uses on Brassica (cole) leafy vegetables and turnip greens (as shown in Ta ble 3.3 below) are for one ground application at planting or at transplanting as an in-furrow or dir ected spray at the base of transplants at the rate of 0.77 lb ai/A. The proposed PHI on the SC labe l is 45 days. No PHI is specified on the DF label, but the use is very early season on both labels.

Peanuts: Peanuts are already registered on th e Flutolanil 40SC Fungicide label (EPA Reg. No. 71711-28) for broadcast use at a maximum of 64.0 fl oz per acre (1.9 lb ai/A) per crop cycle with a 40-day preharvest interval (PHI). The proposed label amendment is to add banded application at a maximum rate of 64.0 fl oz per acre with a 90-day PHI as described in Table 3 below. The peanut use will be added to the Convoy Fungi cide label. (Convoy Fungicide has the same registration number and is the same fo rmulation as Flutolanil 40SC Fungicide.)

Rice: Rice is already regist ered on the Flutolanil 40SC Fungi cide label (EPA Reg. No. 71711- 28). The proposal is to revise th e application rates slig htly (i.e., to revise the rates of 11.8-33.0 fl oz/A and 11.8 to 16.5 fl oz/A on the established label to 12.0 to 33.0 fl oz/A and 12.0 to 16.5 fl oz/A, respectively, on the proposed label). The rice use will be added to the Convoy Fungicide label.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 12 of 36 Table 3.3. Summary of Proposed Directions for Use of Flutolanil.
Applic. Timing, Type, and Equip. Formulation [EPA Reg. No.] Applic. Rate (lb ai/A) Max. No. Applic.

Per Season Max. Seasonal Applic. Rate

(lb ai/A) PHI (days) Use Directions and Limitations**

Brassica (Cole) Leafy Vegetables (Crop Group 5) and Turnip Greens (Proposed) (Broccoli; broccoli, Chinese (gai lon); broccoli raab (rapini); Brussels sprouts; cabbage; cabbage, Chinese (bok choy); cabbage, Chinese (napa); cabbage, Chinese mustard (gai choy); cauliflower; cavalo 12roccoli; collards; kale; kohlrabi; mizuna; mustard greens; mustard spinach; rape greens) At planting or transplanting; In-furrow or directed spray at the base of transplants; Ground equipment Flutolanil 40SC [71711- 28]* 26.0 fl oz/A (0.77 lb ai/A) 1 (implied) 26.0 fl oz/A (0.77 lb ai/A) 45 Apply to the row at planting, as an in-furrow or directed spray at the base of transplants. If transplanted, apply in a narrow band directed at plant bases immediately after transplanting in 30-50 gals/A. Use a minimum of 3 gals. of spray volume per acre. If applied as a soil drench at planting, observe a 45-day PHI.

Brassica (Cole) Leafy Vegetables (Crop Gr oup 5) and Turnip Greens (Registered) At planting or transplanting; In-furrow or directed spray at the base of transplants; Ground equipment Moncut® 70-DF [10163-

301] 1.1 lb/A (0.77 lb

ai/A) 1 (implied) 1.1 lb/A (0.77 lb

ai/A) Not Stated Make one application to therow at planting, as an infurrow or directed spray at the base of transplants. Apply in a minimum of 3 gallons of spray per acre. Do not use oil as carrier or add other additives to the finished spray. Use is prohibited in some areas of Arkansas and NY state. Peanuts (Proposed) Postemergence; Band application; Ground equipment Flutolanil 40SC [71711- 28]*

Convoy® Fungicide [71711- 28]* 48.0-64.0 fl oz/A (1.4-1.9 lb ai/A) broadcast equivalent not stated 64.0 fl oz/A (1.9 lb ai/A) 90 For ground application, apply in a minimum of 20 gals broadcast equivalent of water per acre. Apply in a band over the row within 40-60 days after planting but only after the entire crop has emerged.

Peanuts (Registered) Postemergence; Broadcast application; Ground or aerial equipment Flutolanil 40SC [71711- 28] 20.0-32.0 fl oz/A ( 0.59 – 0.95 lb ai/A)

or 10.0-16.0 64.0 fl oz/A (1.9 lb ai/A) 40 Apply in a minimum of 10 gal water per acre by ground or 5 gals water per acre by air. Begin applications approximately 45-60 days after planting.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 13 of 36 fl oz/A ( 0.30 – 0.48 lb ai/A) Make sequential applications at 21-30 day intervals at the higher rate or at 10-14 day intervals at the lower rate. Rice (Proposed) Postemergence; Broadcast; Ground or aerial equipment Flutolanil 40SC [71711- 28]*

Convoy® Fungicide [71711- 28]* 12.0-33.0 fl oz/A (0.36-0.98 lb ai/A) 1 33.0 fl oz/A (0.98 lb ai/A) 30 Apply in a minimum of 10 gal of water/A by ground or 5 gal/A by air. Apply 7-14 days after panicle differentiation. If applied at the lower rate, follow with a second application 10-14 days after the first. Do not apply within 30 days prior to harvest, or beyond 75% heading development stage, whichever occurs first. Flooded fields may be used by aquaculture of crayfish only following rice harvest. 12.0-16.5 fl oz/A (0.36-0.49 lb ai/A) 2

Rice (Registered) Postemergence; Broadcast; Ground or aerial equipment Flutolanil 40SC [71711- 28]* 11.8-33.0 fl oz/A (0.35-0.98 lb ai/A) 1 33.0 fl oz/A (0.98 lb ai/A) 30 Apply in a minimum of 10 gal of water/A by ground or 5 gal/A by air. Apply 7-14 days after panicle differentiation. If applied at the lower rate, follow with a second application 10-14 days after the first. Do not apply within 30 days prior to harvest, or beyond 75% heading development stage, whichever occurs first. Flooded fields may be used by aquaculture of crayfish only following rice harvest. 11.8-16.5 fl oz/A (0.35-0.49 lb ai/A) 2

*Formulations: Flutolanil 40SC Fungicide, also called Convoy® Fungicide, is a suspension concentrate which contains 3.8 lb ai/gal. Moncut® 70-DF is a dry flowable containing 70.0% ai. ** Rotational Crops: Rotational crop restrictions on the established 40SC label are not being changed. Plantback restrictions on the established SC label are 0 days for cotton, peanuts, potatoes, rice, and soybeans; 30 days for wheat; 150 days for leafy vegetables and small grain crops other than wheat; 240 days for corn and sorghum; and 365 days for all other
crops. Rotational crop restrictions on the established 70-DF label are 0 days for cotton, peanut s, potatoes, rice, soybeans, and turnip greens, and Brassica (cole) leafy vegetables; 30 days for wheat; 150 days for leafy vegetables and small grain crops other than wheat; 240 days for corn and sorghum; and 365 days for all other crops. The 70-DF is not for use on peanuts and rice in CA.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 14 of 36 Conclusions

.

Brassica (cole) leafy vegetables and tu rnip greens: The proposed use directions are adequate to allow evaluation of the residue data relative to the proposed use.

Since Brassic a (cole) leafy vegetables a nd turnip greens are being regi stered on the SC label, the rotational crop restric tions for the Flutolanil 40SC (EPA Reg. No. 71711-28) label should be amended to include Brassica (cole) leafy vegetables and tu rnip greens under the 0-day crop restriction interval.

Peanuts: The proposed band use directions for pe anuts are adequate to allow evaluation of the residue data relative to the proposed use.

Rice: HED has no objection to the minor rate change proposed for ri ce, i.e., to change the lowest application rate from 11.8 to 12.0 fl oz /A. No additional data are needed.

4.0 Metabolite/Degradate Residue Profile

4.1 Nature of the Residue Metabolism Assessment Review Committee (MARC) Memo, No DP Barcode, M. Xue, 1/6/00 Memo to the MARC, D261391, M. Xue, 12/10/99 Residue Chemistry Memo DP# D364462, S. Funk, 1/25/10 Risk Assessment Document DP# D370200, K. Rury, 10/13/10

4.1.1 Summary of Plant Metabolism (860.1300)

The nature of the residue in plants is ade quately understood based on acceptable metabolism studies submitted previously on rice, cucumber leaves, and peanuts. When fluopicolide is metabolized, the amide linkage between the tw o aromatic rings remains intact; metabolism occurs at the more highly activated ami nophenyl ring. Flutolanil is metabolized via O

deisopropylation, hydroxylation, and methylation to yield N -(3'-hydroxyphenyl)-2- (trifluoromethyl)benzamide (M-4) and N -(4'-hydroxy-3'-methoxy)phenyl-2- (trifluoromethyl)benzamide (M-7). Most of th e metabolites are found bound or conjugated. The major identified components in plants were parent and metabolite M-4. The parent compound and metabolites containing the common moiety, 2-(t rifluoromethyl)benzanilide, are the residues of concern which need to be included in the tolerance expression and dietary risk assessment. The enforcement method converts parent a nd metabolites containing the common moiety 2- (trifluoromethyl)benzanilide to 2- (trifluoromethyl)benzoic acid.

4.1.2 Summary of Livestock Metabolism (860.1300)

The nature of the residue in livestock is adequately understood based on acceptable metabolism studies in goats and poultry. As with plants, the amide linkage between the two aromatic rings remains intact; metabolism occurs at the more highly activated aminophenyl ring. The specific metabolites identified as residues of concern are M-2 ( N -[4'-hydroxy-3'-(1- methylethoxy)phenyl]-2-(trifluoromet hyl)benzamide), M-4, and M-7 in livestock tissues, and the glucuronide/sulfate conjugates of M-4 in milk. The parent co mpound and metabolites containing the common moiety, 2-(trifluoromet hyl)benzanilide, are the residues of concern which need to beFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 15 of 36 included in the tolerance expression and dietar y risk assessment. The enforcement method converts parent and metabolites containing the common moiety 2-(trifluor omethyl)benzanilide to 2-(trifluoromethyl)benzoic acid.

4.1.3 Summary of Confined Rotational Crops (860.l850)

The nature of the residue in rotational crop co mmodities is adequately understood based on an acceptable confined rotati onal crop study with lettuce, radis h, and oat/sorghum conducted with [U- 14 C-aminophenoxy]flutolanil. The major residue components were flutolanil and metabolites M-4 and M-5 ( N -[3',4'-(dihydroxy)phenyl]-2- (trifluoromethyl)benzamid e). The residues of concern for the tolerance expression and dietary ri sk assessment for rotational crops are flutolanil and metabolites containing the common moiety, 2-(trifluoromethyl)benzanilide, which is converted by the enforcement method to 2-(trifluoromethyl)benzoic acid.

The total radioactive residues (TRR) were 0.01-0. 04 ppm in all raw agricultural commodities (RACs) of mature crops at the 366 DAT (days after treatment) plantb ack interval. Residue levels were highest at the 30 DAT interval and decl ined by 90% or more by the 366 DAT interval.

4.1.4 Summary of Metabolites and Degradates

Refer to the summary table in Appendix A.

4.2 Comparison of Metabolic Pathways

Metabolism Assessment Review Committee (MARC) Memo, No DP Barcode No., M. Xue, 1/6/00 Memo to the MARC, D261391, M. Xue, 12/10/99 EFED Drinking Water Memo DP# D414000, E. Malone, 12/12/13

Metabolism of flutolanil in primary plants, rotatio nal crops, and livestock is similar in that the amide linkage between the two aromatic rings re mains intact; metabolism occurs at the more highly activated aminophenyl ring to form compounds containing the common moiety, 2- (trifluoromethyl)benzanilide. Parent is the majo r residue in water; no major (>10%) degradation products were identified in envi ronmental fate studies.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 16 of 36 4.3 Residues of Concern Summary and Rationale Metabolism Assessment Review Committee (MARC) Memo, no DP Barcode No., M. Xue, 1/6/00 Memo to the MARC, D261391, M. Xue, 12/10/99 Residue Chemistry Memo DP# D364462, S. Funk, 1/25/10 Risk Assessment Document DP# D370200, K. Rury, 10/13/10 40 CFR §180.484

Table 4.3. Summary of Metabolites and Degradates to be included in the Risk Assessment and Tolerance Expression*

Matrix Residues included in Risk Assessment Residues included in Tolerance Expression

Plants Primary Crop flutolanil and metabolites converted to 2-(trifluoromethyl)benzoic acid flutolanil and metabolites converted to 2-(trifluoromethyl)benzoic acid Rotational Crop

Livestock Ruminant flutolanil and metabolites converted to 2-(trifluoromethyl)benzoic acid flutolanil and metabolites converted to 2-(trifluoromethyl)benzoic acid Poultry

Drinking Water flutolanil (parent) Not Applicable

5.0 Residue Profile

5.1 Residue Analytical Methods (860.1340)

5.1.1 Data Collection Methods Flutolanil Risk Assessment Document D370200, K. Rury, 10/13/10 Residue Chemistry Memo DP#335050, F. Fort, 11/26/07 Residue Chemistry Memo DP#364462, S. Funk, 01/25/10 Residue Chemistry Memo, DP#371493, A. Acierto, 5/12/10
The data collection methods for peanuts were GC/MS methods which determined residues of flutolanil and its major metabolites after transf ormation to 2-(trifluoromethyl)benzoic acid (2- TFBA). The methods were found adequate for data collection based on accep table recovery data.

The data collection method for cabbage, mustar d greens, and broccoli was the (LC/MS/MS method XAM-65, with minor modification. Nich ino America submitted the LC/MS/MS method XAM-65 as a data collection method for cabbage , mustard greens, and broccoli and proposed that it replace the AU/95R/04 enforcem ent method. The method is entitled LC/MS Determination of Flutolanil and its Metabo lite (M-4) in Cotton Seed and Corn Grains . Method XAM-65 separately determines residues of flut olanil and its major metabolite, M-4. The proposed XAM-65 method was not found acceptable as a data collec tion method and not suitable as a replacement for the enforcement method because it may not determine the flutolanil residues of concern for the tolerance e xpression and dietary risk assess ment. The AU/95R/04 analytical method would be expected to determine higher re sidues of flutolanil-deri ved residues, since it determines all metabolites converted to 2-TF BA (including M-2, M-3, and M-7 in addition toFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 17 of 36 flutolanil and M-4 (F. Fort, DP#335050, 11/26/ 07). Method XAM-65 is acceptable as a confirmatory enforcement method (S. Funk, DP#364462, 01/25/10).

Although residues from the field trials on Brassica (cole) leafy vegetables (crop group 5) and turnip greens were determined by a data collect ion method that in general might understate the residue by measuring only flutolanil and its metabolite M-4, in the case of the data set for these crops HED believes the tolerances are adequate. Th e use is at-plant/at-transplant to the soil and is therefore very similar to the conditions of a rotational crop tria l. A confined rotational crop study indicated that residues de termined by the enforcement me thod (common moiety method) in lettuce, a crop similar to the Brassica (cole) leafy vegetables, we re 0.08 ppm. This is in agreement with the results of the subject field tria ls, where the combined re sidue of flutolanil and metabolite M-4 were <0.1 ppm.

Conclusion s: An adequate GC/MS data collectio n method is available based on adequate recovery data. Although the LC/MS/MS method might genera lly understate the residue by measuring only flutolanil and its metabolite M-4, the method together with the rotational crop data are adequate to su pport the tolerances on Brassica (cole) leafy vegetables (crop group 5) and turnip greens.

5.1.2 Multi-Residue Methods (860.1360) Residue Chemistry Memo DP# D190584, J. Garbus, 3/24/94 Residue Chemistry Memo DP# D364462, S. Funk, 1/25/10

Adequate multiresidue method testing data for flutolanil and metabolite M-4 were submitted in conjunction with the previous peti tions on rice. Both analytes were tested using Protocol I (corresponding to current Protocols C, E, and F) and Protocol III (correspo nding to Protocol D). Because neither flutolanil nor metabolite M- 4 was recovered through the Florisil column, no further testing was conducted under Protocol I. Under Protocol III (a.k.a. D), recoveries at fortifications levels of 0.05 ppm and 0.5 ppm we re 90.2% and 90.9%, respec tively, for flutolanil and 68.4% and 88.2%, respectively, for M-4. Neithe r analyte was recovered from spiked rice samples at 0.05 ppm. The multiresidue test results were forwarded to FDA.

Conclusions . The requirements for multiresidue me thods testing have been met. The multiresidue test results were forwarded to FDA.

5.1.3 Tolerance Enforcement Methods Flutolanil Scoping Document for Registratio n Review, D349580, M. Ottley, 8/7/08 Flutolanil Risk Assessment Document D370200, K. Rury, 10/13/10 Residue Chemistry Memo DP#335050, F. Fort, 11/26/07 Residue Chemistry Memo DP#364462, S. Funk, 01/25/10 Residue Chemistry Memo, DP#371493, A. Acierto, 5/12/10

Enforcement Methods for Plants and Livestock Commodities :

A GC/MS enforcement method (AU/95R/04) orig inally submitted by AgroEvo USA Company is available. The method is av ailable in MR ID 44526201, entitled Validation of an Analytical Method for Residues of Flutolan il in Milk, Peanuts, and Rice . The method determines allFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 18 of 36 metabolites converted to the common moiety 2-(trifluoromethyl)benzoic acid (2-TFBA), including flutolanil, M-2, M-3, M-4, and M-7.

Briefly, residues of flutolanil and its metabolite s are extracted from rice and peanut commodities by blending with acetone. Residues in peanut nutm eat and meal are extracted into acetonitrile by blending with acetone followed by ACN:water (80: 20). Residues in fat are extracted into acetonitrile by blending the sample with equal pa rts of ACN and hexane. The solvent extracts are cleaned up and hydrolyzed to 2-(trifluoro methyl)benzoic acid (2 -TFBA). The acid is methylated with methyl iodide. The methyl ester of 2-(trifluoromethyl)ben zoic acid is quantified by GC/MS. The limits of quantitation (LOQs) are 0.05 ppm for whole milk and livestock tissues and 0.2 ppm for rice and peanut matrices.

The method was found adequate for data collect ion based on acceptable r ecovery data. The method has undergone a successful independent la boratory validation with peanut nutmeat and hay, rice grain, milk, eggs, beef muscle, and b eef fat. Radiovalidation was conducted on peanut vines, hulls, and nutmeats using a similar GC /MS common moiety met hod (AU/01/94). Method AU/95R/04 determines the flutolan il residues of concern for the tolerance expression and risk assessment. However, it was noted that a confir matory method is required because the method is a common moiety method. Method XAM-65 is acceptable as a confirmatory enforcement method (S. Funk, DP#364462, 01/25/10).

Conclusions : Adequate enforcement methods are av ailable. A GC/MS enforcement method (AU/95R/04) analyzes the flutolan il residues of concern in plants and livestock commodities for the tolerance expression and risk assessmen t. The method is available in MRID 44526201, entitled Validation of an Analytical Method for Residues of Flutol anil in Milk, Peanuts, and Rice . The method has undergone a successful inde pendent validation with peanut nutmeat and hay, rice grain, milk, eggs, beef muscle, and beef fat. The AU/95R /04 analytical method determines all metabolites converted to the co mmon moiety 2-(trifluorom ethyl)benzoic acid (2- TFBA), including flutolanil, M-2, M-3, M-4, and M-7. The LOQs are 0.05 ppm for whole milk and livestock tissues and 0.2 ppm for rice and pe anut matrices. Radiovalidation was conducted on peanut vines, hulls, and nutmeats usi ng a similar GC/MS common moiety method (AU/01/94). A confirmatory method is requir ed because the method AU/95R/04 is a common moiety method. Nichino America submitted an LC/MS/MS method (XAM-65), which is acceptable as a confirmatory enforcement meth od. Method XAM-65 separately determines residues of flutolanil and its major metabolite, M-4.

5.1.4 Submittal of Analytical Reference Standards (860.1650)

Analytical reference standards for flutolanil, the common moiety 2-(trifluoromethyl)benzoic acid, M-2, M-3, M-4, and M-7 must be kept availa ble at the EPA National Pesticide Standards Repository. The only flutolanil st andards that are in stock are flutolanil and the common moiety 2-(trifluoromethyl)benzoic acid (e-mail from Theresa Cole, Analytical Chemistry Branch, 1/9/14).

When new standards are submitted, they should be sent to the Analytical Chemistry Lab, which is located at Fort Meade, to the attention of either Theresa Cole or Thuy Nguyen at the followingFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 19 of 36 address:

USEPA National Pesticide Standards Repository/Analytical Chemistry Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755-5350

The full 9 digit zip code is mandatory or the mail will be returned to you.

5.2 Storage Stability (860.1380) Residue Chemistry Memo DP# D267657, W. Wassell, 8/2/00 (Rice grain and straw) Residue Chemistry Memo DP# D213567, J. Garbus, 5/4/95 (Peanut) Residue Chemistry Memo DP# D335050, F. Fort, 11/26/07 (Rice and Peanut) Residue Chemistry Memo DP# D371493, A. Acierto, 5/12/10 ( Brassica l eafy vegetables)

Brassica (cole) leafy vegetables and turnip greens : Adequate storage stability data were previously submitted for flutolanil and its me tabolite M-4 in/on cabbage, mustard greens, and broccoli. The data indicate that residues of flutolanil and its metabolite M-4 converted to the common moiety, 2-TFBA, are stable in frozen st orage up to 297 days in cabbage, 519 days in mustard greens, and 569 days in broccoli.

Peanuts: Adequate storage stability data were previously submitted for flutolanil and its metabolite M-4 in/on peanut commodities. The data indicate that residues of flutolanil and its metabolite M-4 converted to the common moiet y, 2-TFBA, are stable in frozen storage (temperature not specified) for up to 3 years in/on peanut nutmeat, oil, hulls.

Rice: Adequate storage stability data were prev iously submitted for flutolanil and its metabolite M-4 in/on rice commodities. The data indicate that residues of flutolanil and its metabolite M-4 converted to the common moiet y, 2-TFBA, are stable in frozen storage (-20 °C) for up to ~31 months in/on rice grain and straw.

Table 5.2. Summary of Storage Conditions and Durations of Samples from Crop Field Trials. Matrix [MRID] Storage Temperature (°C) Actual Storage Duration (days) Interval of Demonstrated Storage Stability Broccoli [47832603] -4 to -22 o C 357 to 564 569 days Cabbage [47832601] -29 to -10 oC 48 to 293 297 days Mustard greens [[47832602] -4 to -22 o C 299 to 511 519 days Peanuts [42742004] frozen 904 – nutmeat 916 - hay 3 years in/on nutmeat, oil, and hulls Peanuts [43175801] frozen 407 – nutmeat and hay Rice [48092301] -20 ± 5°C 32-84 days 1 (1.1-2.8 months) ~ 31 months in/on rice grain and straw (MRID 44526202)

1 Interval from harvest to extraction for analysis. Ex tracts were stored up to 1 day prior to analysis.

Conclusions : Adequate storage stability data are avai lable to support the stor age intervals of the field trial residue samples for Brassica (cole) leafy vegetables and turnip greens, peanuts, andFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 20 of 36 rice. The data show that resi dues of flutolanil and M-4 are st able under frozen storage for the storage durations of the samples.

5.3 Residue Data

5.3.1 Crop Field Trials (860.1500)

Brassica (Cole) Leafy Vegetable Group 5 and Turnip Greens Residue Chemistry Memo DP# D371493, A. Acierto, 5/12/10 Residue Chemistry Memo DP# D381713, S. Funk, 9/7/10 Risk Assessment Document DP# D370200, K. Rury, 10/13/10
Field trial residue data were previously reviewed for broccoli (MRID 47832603), cabbage (MRID 47832601), and mustard greens (MRID 47832602). Moncut 70-DF (source: Gowan Company; EPA Reg. No. 10163-301) was applied in al l trials. The representative crops for the Brassica (cole) leafy vegetable group 5 are broccoli or cauliflower, cabbage, and mustard greens. The residue data were summa rized in D371493 (A. Acierto, 5/ 12/10) as shown in Table 5.3.1.1 below. Adequate storage stability data and analytical methods are available to support the recommended tolerances on the Brassica (cole) leafy vegetables and turnip greens (D371493, A. Acierto, 5/12/10 and D381713, S. Funk, 9/7/10).

The residue data on Brassica were obtained using a DF form ulation. The proposed formulation is a suspension concentrate (SC) formulation. Data can be translated from DF to SC formulations since the PHI is longer than 7 days ( OECD Guideline for the Testing of Chemicals, Crop Field Trial , September 7, 2009).

The available residue data are adequate to suppo rt tolerances of 0.20 ppm on turnip greens and the Brassica leafy vegetables crop group 5.

TABLE 5.3.1. 1. Summary of Residue Data on Cabbage, Mustard Greens, and Broccoli from Field Trials with Flutolanil (Moncut 70-DF).

Crop Matrix Analyte Applic. Rate

(lb ai/A) PHI (days) Residue Levels (ppm) †
n* Min. † Max. † LAFT* HAFT * Median* Mean* SD*

Broccoli Flutolanil 0.411 – 0.775 54 - 106 11 < 0.05 < 0.05 < 0.05 <0.05 < 0.05 < 0.05 NA
M-4 11 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 NA
Total 11 <0.10 <0 .10 <0.10 <0.10 <0.10 <0.10 NA Cabbage Flutolanil 0.72 – 0.788 62 - 138 9 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 NA 2

M-4 9 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 NA
Total 9 <0.10 <0.10 <0.10 <0.10 <0.10 <0.10 NA
Mustard Greens Flutolanil 0.195– 0.784 31 - 63 10 < 0.05 0.06 < 0.05 0.06 < 0.05 0.051 0.003
M-4 10 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 < 0.05 NA
Total 10 <0.10 <0.11 <0.10 <0.11 <0.10 <0.10 0.003

† Values based on total number of samples. Each field trial had two reported residue values. * Values based on per-trial averages. LAFT = Lowest Average Field Trial, HAFT = Highest Average Field Trial, SD = Standard Deviation. For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ. NA = not applicable.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 21 of 36 The residue data in Table 5.3.1.2 were include d in the OECD tolerance calculator for Brassica (cole) leafy vegetables.

Table 5.3.1.2. Summary of Residues from Field Trials with Flutolanil
Crop Matrix Analyte Applic. Rate (lb ai/acre) PHI (days) n * Residues (ppm)

Min. † Max. † LAFT * HAFT * Median * Mean * SD *
BRASSICA (COLE) LEAFY VEGETABLES. Proposed Use = 0.77 lb ai/acre total application rate, 45-day PHI.

Broccoli parent + M-4 0.411- 0.775 54-106 11 <0.10 <0.10 <0.10 <0.10 <0.10 <0.10 NA

Cabbage parent + M-4 0.72-0.788 62-138 9 <0.10 <0.10 <0.10 <0.10 <0.10 <0.10 NA

Mustard Greens parent + M-4 0.195- 0.784 31-63 10 <0.10 <0.11 <0.10 <0.11 <0.10 <0.10 0.003

† Values based on total number of samples. * Values based on per-trial averages. LAFT = Lowest Average Field Trial, HAFT = Highest Average Field Trial, SD = Standard Deviation. For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ.

Peanuts Residue Chemistry Memo DP# D190879, G. F. Kramer, 1/12/94 Residue Chemistry Memo DP# D213567, J. Garbus, 5/4/95
Field trial data were previously submitted on pea nuts reflecting band and broa dcast applications.

Nichino America, Inc. has cited field trial data reflecting band applications (MRID 42742004; DP# D190879, G. F. Kramer, 1/12/94) to support th e proposed label revision. Eight field trials in Region 2 (VA, GA, AL; two trials each) and Region 6 (OK; two trials) reflected one band application of Flutolanil 50 WP (a wettable powder formulation) at rates of 2.2 -9.0 lb ai/A with PHIs of 40-41 days (Table 5.3.1.3 below). The residues were determined by a GC/MS method which transformed flutolanil and its metabolites to 2-TFBA. The method was adequate for data collection based on adequate concurrent recove ries. Although the reported LOQ was 0.05 ppm, adequate recoveries were not reported at 0.05 ppm . Adequate concurrent recoveries (within approx. 70% and approx 120%) were reported at a fortification le vel of 0.2 ppm for nutmeats and hulls. The samples were stored frozen (-20°C). The maximum storage interval was 904 days for nutmeats and 916 days for hay.

Six field trials in Region 2 (AL, NC, GA), Region 6 (OK, TX) and Region 8 (TX) (MRID 43175801; DP# D213567, J. Garbus, 5/4/95) are also available reflecting broadcast application of Moncut® 70 WG (a water disper sible granular formulation) with ground equipment at rates of 1.9-2.1 lb ai/A and PHIs of 39-41 days (Table 5.3. 1.4 below). The residues were determined by a GC/MS method which transformed flutolanil and its metabolites to 2-TFBA. The method was adequate for data collection based on adequate concurrent recoveries. The LOQ for peanut nutmeat and hay was 0.05 ppm, the lowest level of method validation. The samples were stored frozen (-20°C). The maximum storage in terval for nutmeats and hay was 407 days.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 22 of 36 The previously submitted broadcast and bande d residue data on peanuts are from WG/WDG (water-dispersible granule) and WP (wettable powd er) formulations. Data can be translated from WG/WDG and WP formulations to the SC (suspens ion concentrate) formulations since the PHI is longer than 7 days ( OECD Guideline for the Testing of Chemicals, Crop Field Trial

, September 7, 2009).

Adequate geographic representati on has been provided (Table B, Appendix B.) Table B includes both band and broadcast field trials (MRIDs 42742004 and 43175801).

Adequate storage stability data are availabl e to support the field tr ials in MRIDs 42742004 and 43175801. Flutolanil and its metabolites are stable for 3 years in peanut meat, oil, and hulls (MRID 43175802).

The raw agricultural commodities (RACs) of peanut are nutmeat and hay. The shell is removed from nuts before analysis for residues.

Table 5.3.1.3. Field Trial Residue Data for Flutolanil 50 WP in/on Peanut RACs from One Band Application (MRID 42742004; D190879, G. F. Kramer, 1/12/94).
RAC Location (County, State) Bandwidth (inches) Use Rate (lb ai/A) PHI* (days) Residues (ppm) Hay Suffolk, VA (Region 2) 10 7.0 41 25.32 20 3.5 41 7.68 Seminole, GA (Region 2) 9 2.2 40 1.62 18 2.2 40 2.81 Houston, AL (Region 2) 9 2.2 40 1.54 18 2.2 40 3.99 Caddo, OK (Region 6) 9 9.0 40 4.00 18 4.1 40 6.24 Nutmeats Suffolk, VA (Region 2) 10 7.0 41 0.19 20 3.5 41 0.12 Seminole, GA (Region 2) 9 2.2 40 <0.05

18 2.2 40 <0.05 Houston, AL (Region 2) 9 2.2 40 0.06 18 2.2 40 0.11 Caddo, OK (Region 6) 9 9.0 40 0.14

18 4.1 40 0.37 *from treatment to digging

Table 5.3.1.4. Field Trial Residue Data for Flutolanil (Moncut 70 WG) in/on Peanut RACs from One Broadcast Application (MRID 43175801; D213567, J. Garbus, 5/4/95). RAC Location (County, State) Use Rate (lb ai/A) PHI* (days) Residues (ppm)

Hay Waller, TX (Region 6) 2.1 40 8.48

Collingsworth, TX (Region 8) 2.0 39 3.34

Houston, AL (Region 2) 2.1 40 4.77

Halifax, NC 1.9 41 9.33Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 23 of 36 (Region 2) Macon, GA (Region 2) 2.1 41 6.14

Caddo, OK (Region 6) 2 40 12.89

Nutmeats Waller, TX (Region 6) 2.1 40 0.24

Collingsworth, TX (Region 8) 2.0 39 0.12

Houston, AL (Region 2) 2.1 40 0.15

Halifax, NC (Region 2) 1.9 41 0.17

Macon, GA (Region 2) 2.1 41 0.11

Caddo, OK (Region 6) 2 40 0.10

* from treatment to digging

The residue data in Table 5.3.1.5 were included in the OECD tolerance cal culator for peanuts.

Table 5.3.1.5.. Summary of Residues from Field Trials with Flutolanil
Crop Matrix Analyte Applic. Rate (lb ai/acre) PHI (days) n * Residues (ppm)

Min. * Max. * LAFT * HAFT * Median * Mean * SD *
PEANUTS Proposed Use = 1.9 lb ai/acr e total application rate, 90-day PHI.
hay 2- TFBA 1 1.9-2.2 39-41 10 1.54 12.89 1.54 12.89 4.38 5.49 3.7

nutmeat 2- TFBA 1 1.9-2.2 39-41 10 0.05 0.24 0.05 0.24 0.11 0.12 0.059

* Values based on per-trial averages; one residue value was reported for each field trial. LAFT = Lowest Average Field Trial, HAFT = Highest Average Field Trial, SD = Standard Deviation. For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ.

1 The analytical method determines all metabolites converted to the common moie ty 2-(trifluoromethyl)benzoic acid (2-TFBA), including flutolanil (M-1), M-2, M-3, M-4, and M-7. Residues are expressed as flutolanil equivalents.

Conclusions

.

Brassica (cole) leafy vegetables and turnip greens: The available residue data are adequate to support addition of the proposed uses on Brassica (cole) leafy vegetables and turnip greens to the SC label. The residue data on Brassica were obtained using a DF formulation. The proposed formulation is a suspension concentrate (SC) formul ation. Data can be translated from DF to SC formulations since the PHI is longer than 7 days ( OECD Guideline for the Testing of Chemicals, Crop Field Trial , September 7, 2009). Residues in the Brassica leafy vegetables are generally less than the LOQ (<0.05 ppm). However, since detectable residues were found in one mustard green sample, HED recommends that the establishe d tolerances of 0.1 ppm on turnip greens and the Brassica leafy vegetables crop group 5 be increased to 0.20 ppm.

Peanuts: The available residue da ta are adequate to add band app lication to the SC label. The proposed use rate is the same maximum seasonal ra te as the registered broadcast rate with a longer PHI (90 days instead of 40 days). The available residue data from the WP and WG/WDG formulations can be translated to the SC formul ation since the PHI is longer than 7 days. TheFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 24 of 36 geographic representation includ ing band and broadcast applicati ons is adequate. Adequate storage stability data are available. The es tablished tolerance (40 CFR §180.484) of 0.5 ppm on peanut is adequate. Based on the OECD tolerance calculation pr ocedures, the 15.0 ppm established tolerance on peanut hay s hould be increased to 20.0 ppm.

Rice: Use of the Flutolanil 40 SC formul ation on rice was previously reviewed and recommended (D379515, A. Acierto, 10/8/10). HED ha s no objection to the minor rate change proposed for rice on the Flutolanil 40 SC label, i.e., to change th e lowest application rate from 11.8 to 12.0 fl oz/A (0.35 to 0.36 lb ai/A). The minor label revisi on (discussed under the Proposed Use Section above) doe s not require any additional residue data review. The established tolerance (40 CFR §180.484) of 7.0 ppm on rice grain is adequate.

5.3.2 Field Rotational Crops (860.1900) Metabolism Assessment Review Committee (MARC) Memo, No DP Barcode No., M. Xue, 1/6/00 Residue Chemistry Memo DP# D364462, S. Funk, 1/25/10
Field rotational crop studies were previously submitted and reviewed for winter wheat, corn, soybeans, and cotton planted 2, 3, or 4 months (wheat) or 8-10 months (corn, cotton, and soybean) following the harvest of flutolanil-treat ed peanuts. In addition, field rotational crop studies were submitted and reviewed for soybean and grain sorghum following the harvest of flutolanil-treated rice.

More recently, Nichino America, Inc. has submitte d the results of a fiel d rotational crop study on corn and cotton. For this latter study, samples of corn and cotton ma trices were stored frozen for 7.5-8 years from harvest to analysis. HED concl uded that the field rotational study on corn and cotton is unacceptable because no st orage stability data are available which demonstrate that residues of flutolanil and M-4 are stable in corn forage, fodder a nd grain and cotton seed stored frozen for up to 8 years and because the analyt ical method did not determine the residue of

concern.

A field rotational crop study was also reported on soybeans and wheat co ncurrently with the above study on corn and cotton. Crops were pl anted 29-36 days followi ng application of the 70% WDG formulation at 2.0 lb ai/A (1x the maximu m registered seasonal rate for any crop) to bare soil. Detectable flutolan il-derived residues were found in all crop samples of soybean and wheat except wheat grain, wher e residues were <0.05 ppm.

Rotational crop restrictions are included on the esta blished 40SC label. Pl antback restrictions on the established 40SC label are 0 days for cotton, peanuts, potatoes, rice, and soybeans; 30 days for wheat; 150 days for leafy vegetables and sm all grain crops other than wheat; 240 days for corn and sorghum; and 365 days for all other crops.

Rotational crop restrictions on the established 70-DF label are 0 days for cotton, peanuts, potatoes, rice, soybeans, and turnip greens, and Brassica (cole) leafy vegetables; 30 days for wheat; 150 days for leafy vegetables and small gr ain crops other than wheat; 240 days for corn and sorghum; and 365 days for all other crops. Th e 70-DF is not for use on peanuts and rice in CA.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 25 of 36 Conclusions . Rotational crop restrictions and ina dvertent residue tole rances have been established on the Flutolanil 40SC label (E PA Reg. No. 71711-28) based on the available confined and field accumulation studies.

Since Brassica (cole) leafy vegetables and turnip green s are being registered on the 40SC label, the rotational crop restrictions for the Flutolanil 40SC label (EPA Reg. No. 71711-28) should be amended to include Brassica (cole) leafy vegetables and turnip greens under the 0-day rotational crop restriction interval.

5.3.3 Processed Food and Feed (860.1520) Residue Chemistry Memo DP# D213567, J. Garbus, 5/4/95 Residue Chemistry Memo DP# D201704, J. Garbus, 5/9/94 Residue Chemistry Memo DP# D226667, M. Xue, 2/1/00

Brassica (cole) leafy vegetables and turnip greens: There are no processed commodities associated with Brassica leafy vegetables or turnip greens.

Peanut: The processed commodities for peanut are meal and refined oil. The processing factor for peanuts to meal is 2x (D213567, J. Garbus, 5/ 4/95). The establishe d tolerance of 1.0 ppm for peanut meal is adequate. Residues do not concentrate in refined oil (D190879, G. F. Kramer, 1/12/94).

Rice: The processed commodities for rice are po lished rice and bran. Residues concentrate 1.4x in rice bran but do not concentrate in polis hed rice (DP# D201704, J. Garbus, 5/9/94; DP# D226667, M. Xue, 2/1/00). The established tolerance (40 CFR §180.484) of 10 ppm on rice bran is adequate.

Conclusion : Adequate processing studies are ava ilable for peanuts and rice. Residues concentrate in peanut meal (2x) and rice bran (1 .4x) but do not concentrat e in refined peanut oil or polished rice. There are no proc essed commodities associated with Brassica (cole) leafy vegetables or turnip greens.

5.3.4 Meat, Milk, Poultry and Eggs (860.1480) Residue Chemistry Memo DP# D226667, M. Xue, 2/1/00 Residue Chemistry Memo DP# D364462, S. Funk, 1/25/10

Acceptable feeding studies with dairy cattle and poultry were previously reviewed. No detectable residues of flutolanil and its meta bolites M-2, M-4, or M-7 were found in the whole milk, cream, skim milk, muscle, and fat of dairy cows sacrificed after dosing for 28 days at 29.4 (2.9x), 85.0 (8.5x), and 286 ppm (29x) in the feed. Detectable re sidues were found in liver at 0.05, 0.06, and 0.21 ppm at the 29.4, 85.0, and 286 ppm feeding levels and in kidney at 0.06, 0.15, and 0.82 ppm at the 29.4, 85.0, and 286 ppm feeding levels.

A feeding study on laying hens is available in wh ich hens were dosed with flutolanil for 28 days at levels of 1.29 (0.80x), 3.87 (2.4x), and 12.9 ppm ( 8.0x) in the diet. Eggs were collected throughout the feeding study. Sample s of tissue (liver, breast musc le, thigh muscle, fat, skin) and egg (white, yolk) were analyzed by GC/MS for flutolanil (M-1) and its major metabolites,Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 26 of 36 M-2, M-4, and M-7. Except for one residue of 0.12 ppm in liver at the hi ghest feeding level, no detectable residues of parent or any metabolite were found.

Livestock dietary burdens are ca lculated in Table 5.3.4 below.

Table 5.3.4. Calculation of Dietary Burdens of Flutolanil Residues to Livestock.

Feedstuff Type 1 % Dry Matter 2 % Diet 2 Recommended Tolerance (ppm) Dietary Contribution (ppm) 3

Beef Cattle Cotton, cotton gin byproducts R 90 5/0 0.20 0.00

Cotton, meal PC 89 5 0.20 0.00 Cotton, hulls R 90 5/0 0.20 0.011 Soybean forage R 35 15/25 8.00 3.42 Rice, grain CC 88 20 7.00 1.59 Soybean, meal PC 92 15/5 0.20 0.011
TOTAL BURDEN -- -- 55 -- 5.03 Dairy Cattle Cotton, undelinted seed PC 88 10 0.20 0.023 Cotton, meal PC 89 10/0 0.20 0.00 Soybean forage R 35 25 8.00 5.71 Soybean hay R 30 5 2.5 0.42 Peanut hay R 85 15 12.89 (HAFT) 2.27 Rice, grain CC 88 20 7.00 1.59 Soybean, meal PC 92 15/0 0.20 0.00
TOTAL BURDEN -- -- 75 -- 10.01 Poultry Cotton, meal PC 89 20/5 0.20 0.011 Rice, grain CC 88 20 7.00 1.40 Peanut, meal PC 85 20 1.00 0.20
TOTAL BURDEN -- -- 45 -- 1.61
Swine Cotton, meal PC 89 15/0 0.20 0.00 Rice, grain CC 88 20 7.00 1.40 Wheat, milled byproducts CC 88 50 0.20 0.10 Peanut, meal PC 85 15 1.00 0.15 Soybean, meal PC 92 5/0 0.20 0.00
TOTAL BURDEN -- -- 85 -- 1.65

1 R: Roughage; CC: Carbohydrate concentrate; PC: Protein concentrate.

2 OPPTS 860.1000 Table 1 Feedstuffs (06/30/2008). First entry is maximum for the particular commodity; second entry is assigned per the total for maximum reasonably based diet.

3 Contribution = ([tolerance /% DM] X % diet) for beef and dairy cattle; contribution = ([tolerance] X % diet) for poultry and swine.

Conclusions. Tolerances are established for residues of flutolanil and its metabolites converted to 2-TFBA in ruminant (cattle, goat, horse, and sheep) commodities at 0.05 ppm for milk, 0.10Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 27 of 36 ppm for fat, 1.00 ppm for kidne y, 2.00 ppm for liver, and 0.0 5 ppm for meat and meat byproducts, and in poultry commodities at 0.05 ppm for egg, fat, meat, and meat byproducts. Feeding studies are available on lactating cows and laying hens. Based on the feeding studies and the maximum reasonably balanced diets for li vestock, the established livestock tolerances are adequate.

5.3.5 Food Handling (860.1460)

There are no proposed uses that are relevant to this guideline topic.

5.3.6 Water, Fish, and Irrigated Crops (860.1400)

There are no proposed uses that are relevant to this guideline topic.

5.4 Food Residue Profile

Crop Field Trials

Brassica (cole) leafy vegetables and turnip greens: The available residue data are adequate to support addition of the proposed uses on Brassica (cole) leafy vegetables and turnip greens to the SC label. The residue data on Brassica were obtained using a DF formulation. The proposed formulation is a suspension concentrate (SC) formul ation. Data can be translated from DF to SC formulations since the PHI is longer than 7 days ( OECD Guideline for the Testing of Chemicals, Crop Field Trial , September 7, 2009). Residues in the Brassica leafy vegetables are generally less than the LOQ (<0.05 ppm). However, since detectable residues were found in one mustard green sample, HED recommends that the establishe d tolerances of 0.1 ppm on turnip greens and the Brassica leafy vegetables crop group 5 be increased to 0.20 ppm.

Peanuts: The available residue da ta are adequate to add band app lication to the SC label. The proposed use rate is the same maximum seasonal ra te as the registered broadcast rate with a longer PHI (90 days instead of 40 days). The available residue data from the WP and WG/WDG formulations can be translated to the SC formul ation since the PHI is longer than 7 days. The geographic representation includ ing band and broadcast applicati ons is adequate. Adequate storage stability data are available. The es tablished tolerances (40 CFR §180.484) of 0.5 ppm on peanut is adequate. Based on the OECD tolerance calculation pr ocedures, the 15.0 ppm established tolerance on peanut hay s hould be increased to 20.0 ppm.

Rice: Use of the Flutolanil 40 SC formul ation on rice was previously reviewed and recommended (D379515, A. Acierto, 10/8/10). HED ha s no objection to the minor rate change proposed for rice on the Flutolanil 40 SC label, i.e., to change th e lowest application rate from 11.8 to 12.0 fl oz/A (0.35 to 0.36 lb ai/A). The minor label revisi on (discussed under the Proposed Use Section above) doe s not require any additional residue data review. The established tolerance (40 CFR §180.484) of 7.0 ppm on rice grain is adequate.

Processing Studies : Adequate processing stud ies are available for pea nuts and rice. Residues concentrate in peanut meal (2x) and rice bran (1 .4x) but do not concentrat e in refined peanut oilFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 28 of 36 or polished rice. There are no proc essed commodities associated with Brassica (cole) leafy vegetables or turnip greens.

Storage Stability : Adequate storage stability data are avai lable to support the storage intervals of the field trial residue samples for Brassica (cole) leafy vegetables and turnip greens, peanuts, and rice. The data show that resi dues of flutolanil and M-4 are st able under frozen storage for the storage durations of the samples.

Meat, Milk, Poultry, and Eggs : Tolerances are established fo r residues of flutolanil and its metabolites converted to 2-TFBA in ruminant (ca ttle, goat, horse, and sheep) commodities at 0.05 ppm for milk, 0.10 ppm for fa t, 1.00 ppm for kidney, 2.00 ppm for liver, and 0.05 ppm for meat and meat byproducts, and in poultry commoditi es at 0.05 ppm for egg, fat, meat, and meat byproducts. Feeding studies are available on la ctating cows and laying hens. Based on the feeding studies and the maximum reasonably ba lanced diets for livestock, the established livestock tolerances are adequate.

Rotational Crops : Rotational crop restrictions and inadve rtent residue tolerances have been established on the Flutolanil 40SC label (E PA Reg. No. 71711-28) based on the available confined and field accumulation studies.

Since Brassica (cole) leafy vegetables and turnip greens are being registered on the 40SC label, the rotational crop restrictions for the Flutolanil 40SC label (EPA Reg. No. 71711-28) should be amended to include Brassica (cole) leafy vegetables and turn ip greens under the 0-day rotational crop restriction interval.

6.0 Tolerance Derivation

No new tolerances were proposed; however, so me tolerance revisions are recommended for plant commodities. No tolerance change s are needed for livestock commodities.

Peanut Nutmeat and Hay (MRIDs 42742004 and 43175801) The Office of Economic Cooperation and De velopment (OECD) tolerance calculation procedures were used for calculating the recomm ended tolerance for the residues of flutolanil on peanut nutmeat and hay. The statistical goal of th e tolerance calculation procedures is to produce a maximum residue limit (MRL) pr oposal in the region of the 95 th percentile of the underlying residues distribution.

The dataset used to determine a tolerance for fl utolanil on peanut nutmeat and hay consisted of data from ten field trials repres enting one band or broadcast app lication at the rate of 1.9-2.2 lb ai/A/season with a 39 to 41-day PHI (MRIDs 42742004 and 43175801). Using the OECD tolerance calculation procedures, the recommen ded tolerances are 0.4 ppm for nutmeats and 20 ppm for hay. HED concludes that the establis hed tolerance of 15.0 ppm on peanut hay should be increased to 20.0 ppm. The established toleran ce of 0.5 ppm on peanut is adequate. The calculator inputs are incl uded in Appendix D.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 29 of 36 Brassica (Cole) Leafy Vegetables and Turnip Greens The OECD calculator was not used on the Brassica leafy vegetables because most of the residues were <LOQ. Tolerances are estab lished in 40 CFR §180.484(a) at 0.1 ppm on turnip greens and the Brassica leafy vegetables crop group 5. The tolerances for turnip, greens and Vegetable, brassica, leafy, group 5 should be revised to 0.20 ppm si nce one field trial contained a quantifiable residue of parent.

Rice The residue data on rice were not reevaluated using the OECD calculator because the proposed label change is minor. The established tolera nces on rice bran and grain are adequate. However, tolerances were established [40 CFR §180. 484(a)] on rice st raw and hulls but tolerances on these commodities are no longer required ( Table 1 Feedstuffs , June 2008). The established tolerances on ri ce straw and hulls should be removed from 40 CFR §180.484(a).

References

A. Acierto, 5/12/10, D371493, Flutolanil: Petition for Establishm ent of Tolerances for Use on Brassica (Cole) Leafy Veget ables Crop Group 5, Turnips and Gins eng. Summary of Analytical Chemistry and Residue Data.

A. Acierto, 10/8/10, D379515, Flutolanil : Label Amendment Request fo r Use of a Flutolanil SC Formulation on Rice. Summary of A nalytical Chemistry and Residue Data.

E. Malone, 12/12/13, D414000, Tier I/II Estimated Drinking Waters Concentrations of Flutolanil for the New Uses on Peanuts (Banded App lications), Brassica Leafy Vegetables (Crop Group 5) Plus Turnip Greens, Turf and Ornamentals for the Product Convoy ® Fungicide, and for Increased the Annual Rate on Turf for the Product ProStar ® 70WP Fungicide (PC Code 128975; DP Barcodes D414000, D414001)

.
F. Fort, 11/26/07, D335050, PP#4F4342/PP#4H5711: Flutolanil (MONCUT 70WG) on Peanut RAC's. Evaluation of Analytical Methods and of Residue Data. MRID Nos. 431758 -00 thru - 12. DP Barcodes D213567 and D213570; CBTS Nos. 15323 and 15324.

G. F. Kramer, 1/12/94, D190879, PP# 3G04214/3H05672. Flutolanil in or on Peanuts. Evaluation of Residue and Anal ytical Data for an EUP and Temporary Tolerances. MRID#s 427420-01 to -05. Barcodes D190879 and D190882. CBTS#s 11818 and 11819.

J. Garbus, 3/24/94, D190584, PP#3G4184/PP#3H5658: New Chemical EUP: Flutolanil (MONCUT 70WG) on Rice RAC's. Evaluation of A nalytical Methods an d of Residue Data. MRID Nos. 426066-01, 426066-03 thru 426066-14, and 426066-19. DP Barcodes D190584 and D190586; CBTS Nos. 11789 and 11790.

J. Garbus, 5/9/94, D201704, PP#3G4184/PP#3H5658: New Chem ical EUP: Flutolanil (MONCUT 70WG) on Rice RAC's. Amendments Pr oposing Revised Sections Band F to Resolve Deficiencies noted in CBTS's Review. DP Barcodes D201704 and D201709; CBTS Nos. 13523 and 13524.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 30 of 36 J. Garbus, 5/4/95, D213567, PP#4F4342/PP#4H5711: Flutolanil (MONCUT 70WG) on Peanut RAC's. Evaluation of Analytical Methods and of Residue Data. MRID Nos. 431758 -00 thru - 12. DP Barcodes D213567 and D213570; CBTS Nos. 15323 and 15324.

K. Rury, 10/13/10, D371200, Flutolanil: Human Health Risk Assessment for Flutolanil on Brassica Leafy Vegetables (Crop Group 5) and Turnip Greens.

M. Ottley, 8/7/08, D349580, Flutolanil. Human Health Assessment Scoping Document in Support of Registration Review.

M. Xue, 12/10/99, D261391, PP# 6F4693 & PP# 4F04380, Flutolanil in/on Potatoes and Rice. Memo to the Metabolism Assessm ent Review Committee (MARC).

M. Xue, 1/6/00, No DP Barcode No., Flutolanil. HED Met abolism Assessment Review Committee (MARC) Meeting Held on 12-16-99. PC Code 128975

.
M. Xue, 2/1/00, D226667, PP#6F04693/PP#6H05749, Flutolanil in/on Potatoes, Potato Processed Commodities, Rice Grain and Rice Stra w. Evaluation of Analytical Methods and Residue Data.

S. Funk, 1/25/10, D364462, Flutolanil. Petition for Exemp tion from the Requirement for a Tolerance for Seed Treatment Use for Sugar B eet Commodities and for the Establishment of Tolerances for Seed Treatment Use for Cotton and Soybean Commodities. Summary of Analytical Chemistry and Residue Data.

S. Funk, 9/7/10, D381713, Flutolanil: Petition for Establis hment of Tolerances for Use on Brassica (Cole) Leafy Vegetables Crop Group 5 and Turnip Greens. Summary of Analytical Chemistry and Residue Data. DP# 381713: Revision of DP# 371493.

W. Wassell, 8/2/00, D267657, PP#6F04693/PP#6H05749, Flutolanil in /on Potatoes and Rice. Review of Storage Stability and Magn itude of Residue Data for Rice.

Attachments Appendix A. Chemical Names and Structures Appendix B. Field Tria l Geographic Distribution Appendix C. International Residue Limits Table Appendix D. OECD MRL Calcul ation Procedure Inputs/OutputsFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 31 of 36 Appendix A. Chemical Names and Structures

TABLE A. Chemical Names and Structu res of Flutolanil and Metabolites. Common name; Company code Chemical name Chemical structure

Flutolanil; M-1 N -[3-(1- methylethoxy)phenyl]-2- (trifluoromethyl)benzamide

M-2 N -[4'-hydroxy-3'-(1- methylethoxy)phenyl]-2- (trifluoromethyl)benzamide

M-3 N -[3'-(2-hydroxy-1- methylethoxy)phenyl]-2- (trifluoromethyl)benzamide

M-4 N -(3'-hydroxyphenyl)-2- (trifluoromethyl)benzamide N H O CH 3

CH 3

O

CF 3

N H O CH 3

CH 3

O

CF 3 OH

N H O CH 3

O

CF 3 OH

N H OH

O

CF 3Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 32 of 36 TABLE A. Chemical Names and Structu res of Flutolanil and Metabolites. Common name; Company code Chemical name Chemical structure

M-5 N -[3',4'-(dihydroxy)phenyl]-2- (trifluoromethyl)benzamide

M-6 N -(3'-methoxy)phenyl-2- (trifluoromethyl)benzamide

M-7 N -(4'-hydroxy-3'- methoxy)phenyl-2- (trifluoromethyl)benzamide

M-11 2-[[3-[2- (trifluoromethyl)benzoyl]- amino]phenoxy]propanoic acid

2-TFBA 2-(trifluoromethyl)benzoic acid N H OH

O

CF 3 OH

N H O

O

CF 3 CH 3

N H O

O

CF 3 CH 3

OH

N H O CH 3

O

CF 3 O

O H

O

CF 3 OHFlutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 33 of 36 Appendix B. Field Trial Geographic Distribution

Table B. Geographic Representation

NAFTA Growing Region Peanut Submitted Requested US

1 1A 2 9 8/5 3 1/1 4 5 5A 5B 6 4 2/2 7 7A 8 1 1/1 9 10 11 12 13 Total 14 12/9Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 34 of 36 Appendix C. International Residue Limits Table



### Flutolanil (128975; 12/12/2013) Table C. Summary of US and Internatio nal Tolerances and Maximum Residue Limits

US Canada Mexico 1 Codex 2 Residue Definition : 40 CFR180.484 (a)

flutolanil, N -(3-(1- methylethoxy)phenyl)-2- (trifluoromethyl)b enzamide, and its metabolites converted to 2- (trifluoromethyl) benzoic acid and calculated as flutolanil. None For plant commodities, flutolanil. For animal commodities, flutolanil and transformation productscontaining the 2-trifluoromethylbenzoic acid moiety, expressed as flutolanil.

Commodity Tolerance (ppm) /Maximum Residue Limit (mg/kg) Commodity US Canada Mexico 1 Codex 2
Peanut 0.5 Peanut, hay 20.0 Peanut, meal 1.0 Rice, bran 10.0 10 (unprocessed)
Rice, grain 7.0 2 husked 1 polished Rice, hulls 25.0 Rice, straw 10.0 10 Turnip, greens 0.20 Vegetable, brassica, leafy, group 5 0.20
Completed: M. Negussie;12/12/2013

1 Mexico adopts US tolerances and/or Codex MRLs for its export purposes.Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 35 of 36 Appendix D. OECD MRL Calculat ion Procedure Inputs/Outputs

Peanut Nutmeat (MRIDs 42742004 and 43175801)

1.9-2.2 lb ai/A/season;39-41 day PHI

**Residues (mg/kg) n** 

< 0.05 2

0.06 1

0.1 1

0.11 2

0.12 1

0.15 1

0.17 1

0.24 1

**F lutolanil** 

**Peanut Nut m**  **e at** 

**U S**  **A 1.9-2.2 lb ai/**  **A /**  **season; 39**

**- 4**  **1 day PHI**

**Total number of data (n)** 10 **Percentage of censored data** 20%
**Number of non- c**  **ensored data** 8
**Lowest residue** 0.050 **Highest residue** 0.240
**Median residue** 0.110

**Mean** 0.116 **Standard deviation (SD)** 0.059 **Correction factor for censoring (CF)** 0.867

**Proposed MRL estimate**

**- Highest residue** 0.240
**- Mean + 4 SD** 0.353
**- CF x 3 Mean** 0.302
**Unrounded MRL** 0.353

**Rounded MRL 0**  **.4**Flutolanil Summary of Analytical Chemistry and Residue Data Barcode D413582

Page 36 of 36 Peanut Hay (MRIDs 42742004 and 43175801)

1.9-2.2 lb ai/A/season;39-41 day PHI

**Residues (mg/kg) n** 

1.54 1

1.62 1

2.81 1

3.34 1

3.99 1

4.77 1

6.14 1

8.48 1

9.33 1

12.89 1

**F lutolanil** 

**P eanut Hay** 

**U S**  **A 1.9-2.2 lb ai/**  **A /**  **season; 39**

**- 4**  **1 day PHI**

**Total number of data (n)** 10 **Percentage of censored data** 0%
**Number of non- c**  **ensored data** 10
**Lowest residue** 1.540 **Highest residue** 12.890
**Median residue** 4.380

**Mean** 5.491 **Standard deviation (SD)** 3.712 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 12.890
**- Mean + 4 SD** 20.340
**- CF x 3 Mean** 16.473
**Unrounded MRL** 20.340

**Rounded MRL 2**  **0**