Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 1 of 28 UNITED STATES ENVIRONMENTA L PROTECTION AG ENCY WA SHINGTON, D.C. 20460 OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION MEMORANDUM Date: 09 - FEB - 2011 Subject: Pyrasulfo tole . Section 3 Request for Use on Sorghum and Grass Grown for

Seed . Summary

of Analy tical Chemistry

and Residue Data. PC Code: 000692 DP Barcode: D 375391 Decision No.: 425581 Registration No. : 264 - 1023 Petition No.: 9F7680 Regulatory Action: Section 3 Re gistration Risk Assessment Type: NA Case No.: 7272 T XR No.: None CAS No.: 365400 - 11 - 9 MRID No.: 47815001 and 47815002 40 CFR: 180.631 From: Jennifer R. Tyler, Chemist

Risk Assessment Branch (RAB1) Health Effects D ivision (HED) (7509P ) Through: George F. Kramer, Ph.D., Senior Chemist

RAB1/HED (7509P ) To: Bethan y Benbow/Joanne Miller , RM Team 23

R egistration Division (RD) (7505P ) Baye r CropSciences has submitted a petition for the use of the active ingredient (ai) py rasulfotole ((5 - hydroxy- 1,3 - dimethyl - 1 H - py razol - 4 - yl )[2 - (methylsulfonyl) - 4 - (trifluorometh yl )phen yl ]methanone) on sorghum and grass grown for seed . Baye r has requested the establishment of permanent tolerance s for pyrasulfotole and its metabolite , 5 - hydrox y- 3 - methyl - 1 H

- py razol - 4 - yl ) [ 2 - (methylsulfonyl) - 4 - ( trifluoromethyl )phenyl] methanone , in or on the following raw agricultural commodities (RACs): Sorghum, grain 0.8 ppm Sorghum, forage 1.2 ppm Sorghum, stover 0.35 ppm Grass, forage 10 ppm Grass, hay 2.5 ppm In addition, Bayer has requested permanent tolerances for p yr asulfotole pyrasulfotole ((5 - hydrox y- 1,3 - dimethyl - 1 H - py razol - 4 - yl )[2 - (methylsulfonyl) - 4 - (trifluorometh yl )phen yl ]methanone) i n or on the following commodities:Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 2 of 28 Milk 0.01 ppm Hog, liver 8 ppm Cattle, meat 0.04 ppm Hog, meat byproducts 2 ppm Cattle, fat 0.04 ppm Sheep, meat 0.04 ppm Cattle, liver 8 ppm Sheep, fat 0.04 ppm Cattle, meat byproducts 2 ppm Sheep, liver 8 ppm Goat, meat 0.04 ppm Sheep, meat byproducts 2 ppm Goat, fat 0.04 ppm Horse, meat 0.04 ppm Goat, liver 8 ppm Horse, fat 0.04 ppm Goat, meat byproducts 2 ppm Horse, liver 8 ppm Hog, meat 0.04 ppm Horse, meat byproducts 2 ppm Hog, fat 0.04 ppm Executive Summary Py rasulfotole is a postemergence dicot herbicide currentl y registered for use on small cereal grains, i n cluding wheat, barley , oat, rye , and triticale. Py rasulfotole will be formulated as Huskie TM Herbicide, an emulsifiable concentrate (EC) comprised of 37.5 g/L of py rasulfotole, bromoxy

nil (present as the mixed heptanoate and octanoate esters), and the safener mefenp yr - diethyl for use on grain sorghum and grass grown for seed . The EC formulation is being proposed for two ground or foliar application s per season to the above crops at rate s of 0.073 - 0.078 lb py rasulfotole/A . HED notes that t his document p ertains to the ai pyrasulfotole only. The use directions provided by the petitioner are adequ ate to allow evaluation of the residue data relative to the proposed uses on grain sorghum and grass grown for seed, with the exception of instructions for the use of adjuvants and the proposed application type/equipment or spray volume for grass grown for seed. The submitted magnitude of the residue studies were performed without the use of adjuvants. Therefore, the label should be amended to prohibit the use of adjuvants on grain sorghum and grass grown for seed. Inaddition, the available magnitude of residue data support broadcast foliar spray applications, and a spray volume of 10 - 24 gal/A. The proposed label should be revised to specify instructions of application equipment and spray volume for grass grown for seed. The nature of the p yr asulfotole residues sorghum and grass is understood based on previousl y submitted and reviewed metabolism studies on wheat (Memo, J. Tyler, 6/8/07; D333412) . The metabolism of py

rasulfotole in spring wheat involves the demethyl ation and subsequent glucos yl ation of the parent compound, yielding py rasulfotole - desmeth yl - O - glucoside. There was also cleavage of the complete p yrazole moiety resulting in the p yr asulfotole - benzoic acid metabolite. Based on the results of the wheat metabolism studies, parent and py rasulfot ole desmethyl are the residues of concern for tolerances and risk assessment purposes (Memo, J. Tyler et al. , 06 / 08 /07; D328640). An y future uses on other crops, such as leafy vegetables, or legumes, may

require the submission of additional metabolism dat a. The nature of the p yr asulfotole residues in lives tock is understood based on previously submitted and reviewed lactating goat and laying hen metabolism studies (Memo, J. Tyler, 6/8/07; D333412) . The goat study indicates that the metabolism of py rasulf otole in lactating goats involved either N

- demethylation of py

rasulfotole to form py

rasulfotole - desmethyl, or oxidation of py rasulfotole to form py

rasulfotole - hydrox ym ethyl. The hen study indicates that thePy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 3 of 28 metabolism of py

rasulfotole in laying hens invol ved the N - demeth yl ation of py

rasulfotole to yi eld the p yr asulfotole - desmethyl metabolite. The residues of concern in livestock for tolerance and risk assessment purposes are parent and the desmethyl metabolite (Memo, J. Tyler, 06 / 08 /07; D328640). An adequate high - performance liquid chromatography ( HP LC )/mass spectrometry (MS)/MS method ( Method AI - 001 - P04 - 02 ) is available for collecting data on residues of py rasu lfotole and its metabolite py

rasulfotole - desmeth yl in/on plant commodities. The limit of quant itation (LOQ) is 0.010 ppm for each analy te. A similar method, Method AI - 001 - P04 - 0 1, which is also the proposed enforcement method for plant commodities, has been adequately radio validated and undergone a successful independent laboratory v ali dation (ILV) trial. M ethod AI - 001 - P04 - 01 was forwarded to the Analy tical Chemistry

Branch of the Biological & Economics Analy sis Division (ACB/BEAD ) for a petition method validation ( PMV ; Memo, J . Tyler, 1/30/07; D 335558). ACB reviewed the proposed enforcement metho d data without a laboratory validation, but recommended the petitioner provide information for a second MS/MS ion transition to provide a confirmation of anal yt e identities (Memo, C. Stafford, 6/7/07; D335559). In response, the compan y submitted Bayer Method AI - 001 - P04 - 02 , which includes the requested information for a second MS/MS ion transition. HED reviewed this method, and determined it suitable for determination of py rasulfotole and pyrasulfotole - desmeth ylin crop matrices (Memo, G. Kramer, 12/18/09; D367796). A HPL C - MS/MS method (Method AI - 004 - A05 - 01 ) for collecting data on py rasulfotole in livestock t issues, including milk, matrices was previously submitted and reviewed b y HED (Memo, J. Tyler, 06/08/07; D333412) . However, based on the results of the livestock metabolism studies, the residues of concern in livestock are p yr asulfotole and py rasulfotole desmethyl for tolerance and risk assessment purposes (Memo, J. Tyler et al., 6/8 /07; D328640). Therefore, HED requested the petitioner submit a rumin ant anal yt ical enforcement method to determine residues of p yr asulfotole and p yrasulfotole - desmeth ylas well as adequate radiovalidation and ILV data. In response, the company submitted a new HPL C - MS/MS (Method AI - 006 - A08 - 01) for collecting p yr asulfotole and py rasulfotole - desmethyl in livestock tissues and milk , as well as ILV data. HED reviewed these submissions; and, based on validation data provided by the petitioner and the successful ILV, determined that Method AI 006 - A08 - 01 is suitable as an enforce ment method for livestock commodities as defined in Standard Operating Procedure (SOP) No. ACB - 019 (9/15/08) (Memo, G. Kramer, 12/18/09; D367796). HED also de termined that radiovalidation data are not necessary as the extraction procedures are identical t o the previous version of the method (for which adequate extraction efficiency data were provided). Py rasulfotole and the metabolite py rasulfotole - desmethyl were subjected to anal ys is by selected Protocols of the Food and Drug Administration (FDA) Pestici de Anal yt ical Manual, Volume I (PAM I), third edition. The results indicate that p yrasulfotole is partiall y recovered through Protocol B, and completely recovered through Protocol C module DG - 17. Py rasulfotole desmethyl was not recovered through any of the Protocols. The report has been forwarded to FDA for inclusion in PAM I(Memo , J. Tyler , 1/30/07 ; D335562). No storage stability

data were submitted in conjunction with the proposed uses. The available storage stability

data are acceptable and indicate that residues of p yr asulfotole and py rasulfotole benzoic acid are stable in soy bean seed and wheat matrices for up to 11 months, and residues of py rasulfotole - desmeth yldecline in wheat forage and hay (ca. 0.12 % per day) in frozen storage.Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 4 of 28 The storage stability data support the sample storage intervals and conditions in the submitted crop field trials. C orrections to residues of py rasulfo tole due to in - storage dissipation are not necessary , but residues of py rasulfotole - desmethyl in sorghum forage and stover, and grass forage and hay will require correctio ns for in - storage dissipation. The results of the cattle feeding study are adequate for purposes of this action . HED assumed the transfer of p yrasulfotole - desmethyl from plant to livestock to be equi valent to that of the parent py rasulfotole based on the similar structure . For any new uses which significantly increase the maximum reasonable dietary burden (MRDB) of the metabolite, the petitioner may be requ ired to submit a feeding study with py ra su lf otole - desmethyl . Based on the MRDB for dairy cattle (45 ppm), the actual dose levels in the feeding study are equivalent to 0. 067x, 0.2x, and 0.67x the MRDB for dairy cattle. Based on the res idues at the 0.67x feeding level , the current tolerances of 0.0 2 ppm for meat of cattle, goat, horse and sheep are adequate to support the proposed uses. However, tolerances should be established for residues of p yr asulfotole and py rasulfotole - desmethyl in/on milk at 0.03 ppm; fat of cattle, goat, horse and sheep at 0.03 ppm; liver of cattle, goat, horse, and sheep at 3.0 ppm; and meat by products, except liver, of cattle , goat, horse, and sheep at 0.70 ppm. A revised Section F should be submitted to include the above tolerances , as well as correct commodity definitio ns and tolerance expression for livestock commodities. Based upon a MRDB of 0.56 ppm for hogs, there is no reasonable expectation of finding quantifiable residues of py rasulfotole and py

rasulfotole - desmeth ylin hog muscle and fat ; thus , the current tolerances of 0.02 ppm are adequate. There is reasonable expectation of residues of py rasulfotole and py

rasulfotole - desmeth ylin hog liver and kidney . Therefore, the following tolerances for residues of py rasulfotole and py

rasulfotole - desmeth ylare necessary : hog, meat by products, except liver at 0.05 ppm; and hog, liver at 0.30 ppm. A revised Section F should be submitted to include the above tolerances , as well as correct commodity definitions and tolerance expression for livestock commodities. The results of the poultry feeding study are inadequate to determine the need for poultry tolerances as only

residues of py

rasulfotole - benzoic acid were measured in the study . However , the results of the poultry

metabolism studies can be used to determine the need f or a new poultry feeding study and/or poul try tolerances. Based on the MRDB of 0.52 ppm for poultry , the phenyl - labeled (8.6 ppm) and py razole - labeled (10.5 ppm) poultry metaboli sm studies were conducted at 16x and 20x the MRDB for poultry , respectivel y. Based on the results of the poultry metabolism study, there is no reasonable expectation of finding quantifiable residues of py rasulfotole and py

rasulfotole - desmeth ylin eggs and po ultry muscle and fat ; thus, the current tolerances of 0.02 ppm for residue s of p yr asulfotole and py rasulfotole - desmethyl in fat, meat, and meat b yproducts of poultry are adequate . There is reasonable expectation of residues of py rasulfotole and py

rasulfotole - desmeth ylin poultry meat by products. Therefore, a tolerance of 0.20 ppm for residues of py rasulfotole and py

rasulfotole desmethyl in poultry by products is necessary . A revised Section F should be submitted to include the above tolerances and correct tolerance expression for livestock commodities.Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 5 of 28 The available grain sorghum and grass residue data are classified as scientifically acceptable for determination of the magnitude of residue for and the metabolite py rasulfotole - desmeth ylwhen treated with the end use products Huskie TM Herbicide. As the number and geographical representation of the grain sorghum and grass trials are appropriate , the residue data are adequate to support the proposed uses. The grain sorghum crop field trial data support a maximum se asonal application rate of 0.078 pound (lb) ai/acre (A) (~1x the maximum proposed application rate) on sorghum forage, grain, and stover [preharvest interval ( PHI ) of 5 - 7 day s for forage, 60 day s for grain and stover] . With these use patterns, total residues of p yrasulfotole and pyrasulfotole - desmethyl are not expected t o exceed 0.902 ppm (forage, 7 - day PHI), 0.325 ppm (grain), and 0.420 ppm (stover). Using the North American Free Trade Agreement (NAFTA ) Maximum Residue L imit ( MRL) /Tolerance Harmonization Workgrou p methodology

for forage, grain , and stover ; the available grain sorghum crop field trial data indicate that the appropriate tolerances for residues of py rasulfotole and py rasulfotole - desmethyl in/on grain sorghum commodities are 1.5 ppm for sorghum, grain, forage; 0.70 ppm for sorghum, grain, grain; and 0.80 ppm for sorghum, grain, stover . Section F of the petition should be revised to include the aforementioned HED - recommended tolerances and the correct commodity definitions for grain sorghum RACs. The grass crop field trial data support a maximum seasonal app lication rate of 0.076 - 0.091 lb ai/A (~1x the maximum proposed application rate) on grass forage and hay (PHIof 7 day s for forage , and 30 day s hay). With these use patterns, total py rasulfotole and py

rasulfotole desmethyl residue levels are not expected to exceed 6.52 ppm (forage, 7 - day PHI ) and 2.31 ppm (hay). Using the NAFTA MRL/Tolerance Harmonization Workgrou p methodology for forage (7 - day PHI) and hay , the available grass crop field trial data indicate that the appropriate tolerances for residues of py rasulfotole and py

ra sulfotole - desmeth ylin/on grass commodities are 25 ppm for grass, forage; and 3 .5 ppm for grass, hay . Section F of the petition should be revised to include the aforementioned HED - recommended tolerances . No rotational crop data were submitted in conjunction with the proposed uses. Adequate confined and field rotational crop data have been submitted by the petitioner and reviewed b y HED in conjunction with PP#6F7509 (Memo, J. Tyler, 6/8 /07; D366490). The results of the submitted co nfined and limited field rotational crop studies together are adequate to determine appropriate plantback intervals ( PBI s ) for rotational crops. In addition, HED approved a requested to revise the Crop Rotation Guidelines on the currently approved Huskie TM Herbicide (EPA Reg. No. 264 - 1023) . The submitted confined and limited field trial data support the proposed PBIs . HED Conclusion/Recommendations Provided 1) Section B is revised to include a prohibition on the use of adjuvants on grain sorghum and gra ss grown for seed and instructions of application equipment and spray volume for grass grown for seed; 2) Section F is revised to the HED - recommended tolerances , as well as correct commodity

definitions and tolerance expression s ; and 3) anal yt ical referenc e standards for p yrasulfotole - desmethyl and labeled internal standards are submitted to the EPA National Pesticide Standards Repository , the residue chemistry database supports the establishment of an un conditio nal registration and permanent tolerances as listed below.Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 6 of 28 Tolerances are established for residues of the herbicide py rasulfotole, including its metabolites and degradates, in or on the commodities in the table below . Compliance with the tolerance levels specified below is to be determined b y measuring onl y the sum of pyrasulfotole ((5 - hydrox y- 1,3 - dimethyl - 1 H - py razol - 4 - yl )[2 - (methylsulfonyl) - 4 - (trifluorometh yl )phen yl ]methanone) and its desmethyl metabolite (5 - hydroxy- 3 - methyl - 1 Hpy razol - 4 - yl )[2 - (methylsulfonyl) - 4 - (trifluoromethyl)phenyl]methanone), calculated as the stoichiometric equivalent of py rasulfotole, in or on the following commodities: Sorghum, grain, grain 0.70 ppm Hog, fat * 0.02 ppm Sorghum, grain, forage 1.5 ppm Hog, liver 0.30 ppm Sorghum, grain, stover 0.80 ppm Hog, meat byproducts, except liver 0.05 ppm Grass, forage 25 ppm Sheep, meat * 0.02 ppm Grass, hay 3.5 ppm Sheep, fat 0.03 ppm Milk 0.03 ppm Sheep, liver 3.0 ppm Cattle, meat* 0.02 ppm Sheep, meat byproducts, except liver 0.70 ppm Cattle, fat 0.03 ppm Horse, meat* 0.02 ppm Cattle, liver 3.0 ppm Horse, fat 0.03 ppm Cattle, meat byproducts, except liver 0.70 ppm Horse, liver 3.0 ppm Goat, meat* 0.02 ppm Horse, meat byproducts, except liver 0.70 ppm Goat, fat 0.03 ppm Poultry, meat* 0.02 ppm Goat, liver 3.0 ppm Poultry, fat* 0.02 ppm Goat, meat byproducts, except liver 1.0 ppm Poultry, meat byproducts 0.20 ppm Hog, meat* 0.02 ppm Eggs* 0.02 ppm * The recommended tolerances for these commodities are at the same level as the current tolerances under 40 CFR 180.631. A human - health risk assessment will be prepared as a separate document. Background Py rasulfotole is a postemergence dicot herbicide currentl y registered for use on small cereal grains, including wheat, barley , oat and triticale . Py rasulfotole is an effective inhibitor of the enzy me 4 - hydroxy

phen ylpy ruvate dioxygenase (HPPDase) and consequently blocks the pathway of pren yl quinone bios ynthesis in plants. The end - use products are applied to the target weeds and act primarily

through leaf uptake and translocatio n to the target site. The first sy mptoms appear three to five day s after application. Bleaching and discoloration appear initially and sy mptoms progress to tissue necrosis and plant death within two weeks. Huskie TM Herbicide is an EC mixture containing py rasulfotole , bromox ynil, and mefenp yr - diethyl safener. The nomenclature and phy sicoche mical properties of p yr asulfotole are presented below in Tables 1 and 2.Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 7 of 28 Table 1. Test Compound and Metabolite Nom enclature. Compound Chemical Structure

Common name P yrasulfotole Company Experimental name AE 0317309 IUPAC name 5 - hydroxy- 1,3 - dimethylpyrazol - 4 - yl 2 - mesyl - 4 - (trifluoromethyl)phenyl ketone CAS name (5 - hydroxy- 1,3 - dimethyl - 1 H - pyrazol - 4 - yl)[2 - (methylsulfonyl) - 4 - (trifluoromethyl)phenyl]methanone CAS # 365400 - 11 - 9 End -use products (EP s ) AE 0317309 SE06 Herbicide and AE 0317309 +Bromo Herbicide Compound Chemical Structure O S

F 3 C O O

N N

H O H Common name Py rasulfotole - desmethyl Company Experimental name AE 1073910 CAS name (5 - hydroxy- 1 H - py razol - 4 - yl)[2 - mesyl - 4 - (trif luoromethyl)phenyl]methanone Table 2. Physicochemical Properties of the Technical Grade Test Compound . Parameter Value Reference Melting point Pure: 201°C No boiling point, decomposition starts at 245°C

MRID 46801701 pH at 22.9°C 3.03 Density 1.53 Water solubility (g/L at 20  C) 2.3 4.2 69.1 49.0 pH 3.0 (distilled water) pH 3.9 (buffer pH 4.0) pH 5.4 (buffer pH 7.0)* pH 5.2 (buffer pH 9.0)* * exceeded buffer capacity Solvent solubility (g/L at 20  C) Ethanol n - Hexane Tolune Dichloromethane Ac etone Ethyl acetate Dimethyl sulfoxide 21.6 0.038 6.86 120 - 150 89.2 37.2 ≥ 600 Vapo r pressure at 20  C 2.7 X 10 - 7 Pa Dissociation constant (pKa) 4.2 n - octanol - water partition coefficient Log(KOW) at 23°C 0.276

- 1.362

- 1.580 pH 4.0 pH 7.0 pH 9.0 UV/visible absorption spectrum  ma x= 264, 241, 216 nm in water, 0.1M HCl, 0. 1M NaOH respectively. N N F 3 C O

S O

H O OPy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 8 of 28 860.1200 Directions for Use Py rasulfotole will be formulated as Huskie TM Herbicide, an EC formulation containing 0.31 lb ai/gal py rasulfotole, bromoxy

nil (present as the mixed heptanoate and octanoate esters), and the safener mef

enp yr - diethyl for use on grain sorghum and grass grown for seed . The following rotational crop restrictions are listed on the proposed label: 1 month for wheat, barley, oats, rye and triticale; 4 months for alfalfa, millet, sorghum (grain), and so yb eans; and 9 months for canola, canary seed, chickpeas, corn, dry beans, flax, field peas, green beans, green peas, lentils (for all states except 18 months in MN, MT, ND, and SD), mustards, potatoes, safflower, sunflowers, and sugar beets. Where not specified, the label requires a field bioassay be conducted in order to determine if crop can be successfully rotated with py

rasulfotole. A minimum 30 - day

PBI is required for all crops. Table 3 is a summary of the proposed use patterns. Table 3. Summary of Prop osed Use Patterns. Crops Product

(EPA Reg. No.) Application

Timing; Type; and Equip. #

App. Application

Rate (lb ai/A) RTI 1

(days) PHI 1

(days) Restrictions Per app. Per season S orghum HuskieTM

Herbicide (EPA Reg. No. 264 - 1023) Cr op application

–

apply between 3 - leaf stage of growth up to 12 inches . Ground equipment as a foliar spray . 2 0.0 3 9 0.07 8 11 Forage

– 7 days; grains or stover

– 60 days Apply in 10 - 15

gal of water

/A .

Grass gro wn for seed HuskieTM

Herbicide (EPA Reg. No. 264 - 1023) Crop application

–

apply to actively growing grass between 3 - leaf stage up to 12 inches. 2 0.0 36 0. 073 30 forage

– 7 days ; hay

– 30 days

1 RTI = retreatment interval; PHI = preharvest interval ; NA = n ot applicable. HED Conclusions : The use directions provided by the petitioner are adequate to allow evaluation of the residue data relative to the proposed uses on grain sorghum and grass grown for seed , with the exceptio n of instructions for the use of adjuvants and the proposed application ty pe/equipment or spray

volume for grass grown for seed. The submitted magnitude of residue studies were performed without the use of adjuvants. Therefore, the label should be amended to prohibit the use of adjuvant s on grain sorghum and grass grown for seed. In addition, the available magnitude of residue data support broadcast foliar spray applications, and a spray volume of 10 - 24 gal/A. The proposed label should be revised to specify instructions of application equipment and spray volume for grass grown for seed. 860.1300 Nature of the Residue - Plant s Data concerning the metabolism of py rasulfotole in spring wheat were submitted and reviewed in conjunction with PP #6F7509 (Memo, J. Tyler, 6/8/07; D333412). A total of three studies were submitted, including a phenyl - labeled study (MRID 46801749), a py

razole - labeled study (MRID 46801748), and a phenyl - labeled study comparing the nature of the residue in spring wheat with and without the safener (MRID 46801801). The available wheat meta bolism studies are adequate , and indicate that the metabolism of py rasulfotole in spring wheat involves thePy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 9 of 28 demethylation and subsequent glucos yl ation of the parent compound, yielding py rasulfotole desmethyl - O - glucoside. There wa s also cleavage of the complete py razole moiety

resulting in the py rasulfotole - benzoic acid metabolite as detected by the phenyl - label study and polar fraction (p1) formed from the p yr azole - label study . Fraction p1 was characterized as being natural or in corporated into the matrix. Based on the results of the wheat metabolism studies, parent and py rasulfotole - desmeth ylare the residue s of concern for tolerances and risk assessment purposes (Memo, J. Tyler et al. , 06 / 08 /07; D328640) . T his conclusion appli es to the use of py rasulfotole on grain sorghum and grass grown for seed. However, any future uses on other crops, such as leafy v egetables, or legumes , may require the submission of additional metabolism data. 860.1300 Nature of the Residue - Livestock Data concerning the metabolism of py rasulfotole in ruminants (lactating goat) and poultry ( laying hen) were submitted and reviewed in conjunction with PP #6F7509 (Memo, J. Tyler, 6/8/07; D333412). The nature of the p yr asulfotole residues in livestock is understood based on the acceptable phenyl - and py razole - labeled lactating goat and laying hen metabolism studies. The goat study

indicates that the metabolism of pyrasulfotole in lactating goats involved either N - demethylation of py

rasulfotole to form py

r asulfotole - desmeth yl , or oxidation of py rasulfotole to form py

rasulfotole - hy drox ym eth yl . The hen study indicates that the metabolism of py rasulfotole in laying hens involved the N - demethylation of p yr asulfotole to yield the py rasulfotole - desmeth ylmetabol ite. T he resi dues of concern in livestock for tolerance and risk assessment purposes are parent and the desmethyl metabol ite (Memo, J. Tyler, 06/08 /07; D328640 ). 860.1340 Residue Analytical Method – Plants In the grain sorghum and grass grown for seed magnitude of residue studies, residues of py rasulfotole and its metabolite py rasulfotole - desmethyl quantitated using Bayer Method AI 001 - P04 - 01, an L C - MS/MS using the stable isotopically labeled analy

tes as internal standards. The lowest limit of method v alidation ( LLM V ) for each anal yt e was 0.01 ppm in all matrices. The method is acceptable based on concurrent recoveries. All residues were reported in parent equivalents. Baye r Method AI - 001 - P04 - 01, an HPL C - MS/MS method, has been adequately radiovalidat ed and has undergone a successful ILV trial. The proposed method was forwarded to ACB/BEAD for a PM V (Memo, J. Tyler, 1/30/07; D 335558). ACB reviewed the proposed enforcement method data without a laboratory validation , but recommended the petitioner pro vide information for a second MS/MS ion transition to provide a confirmation of anal yt e identities (Memo, C. Stafford, 6/7/07; D335559). In response, the compan y submitted Baye r Method AI 001 - P04 - 02 (MRID 47806401) , which includes the requested informatio n for a second MS/MS ion transition. HED reviewed this method, and determined it suitable for determination of py rasulfotole and py

rasulfotole - desmeth ylin crop matrices (Memo, G. Kramer, 12/18/09; D367796) .Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 10 of 28 860.1340 Residue Analytical Method – Livesto ck A HPL C - MS/MS method (Method AI - 004 - A05 - 01 ) for c ollecting data on py rasu lfotole in livestock tissues, including milk, matrices was previously submitted and reviewed b y HED (Memo, J. Tyler, 06/08/07; D333412) . However, based on the results of the lives tock metabolism studies, the residues of concern in livestock are p yr asulfotole and py rasulfotole desmethyl for tolerance and risk assessment purposes (Memo, J. Tyler et al ., 6/8 /07; D328640). Therefore, HED requested the petitioner submit a ruminant anal yt ical enforcement method to determine residues of p yr asulfotole and p yrasulfotole - desmeth yl as well as adequate radiovalidation and ILV data . In response, the company submitted a new HPL C - MS/MS (Method AI - 006 - A08 - 01) for collecting p yr asulfotole and py ra sulfotole - desmethyl in livestock tissues and milk (MRID 47860002), as well as ILV data (MRID 47860003). HED reviewed these submissions; and, based on validation data provided b y the petitioner and the successful ILV, determined that Method AI - 006 - A08 - 01 i s suitable as an enforcement method for livestock commodities as defined in SOP No. ACB - 019 (9/15/08) (Memo, G. Kramer, 12/ 18/09; D367796). HED also determined that radiovalidation data are not necessary as the extraction procedures are identical to the p revious version of the method (for which adequate extraction efficiency data were provided) . 860.1360 Multiresidue Methods ( MRM) Baye r CropS cience previously submitted adequate MRM recovery data for py

rasulfotole and the metabolite py

rasulfotole - desmethylthrough FDA Protocols A through E (Memo, J. Tyler, 06/08/07; D328640). Pyrasulfotole and the metabolite py rasulfotole - desmethyl were subjected to analy sis by

selected P rotocols of the FDA PAM I , third edition. Py rasulfotole and py rasulfotole - desmeth yl were tested according to Protocols A, B, and C of the FDA PAM I testing procedures. The results of the MRM analysis indicate that py rasulfotole is partially recovered through Protocol B, and completel y recovered through Protocol C module DG - 17. Py rasulf otole - desmeth ylwas not recovered through any of the Protocols. The report has been forwarded to FDA for inclusion in PAM I(Memo , J. Tyler , 1/30/07 ; D335562). 860.1380 Storage Stability No storage stability

data were submitted in conjunction with the proposed uses . The results of a study to determine freezer storage stability of py rasulfotole, py

rasulfotole - desmethyl, and py rasulfotole - benzoic acid in soy bean and wheat matrices have been submitted and reviewed by HED (Memo, J. Tyler, 06/08/07; D32864 0) . The data are acceptable and indicate that residues of py rasulfotole and py

rasulfotole - benzoic acid are stable in soy bean seed and wheat matrices for up to 11 months, and residues of p yrasulfotole - desmethyl decline in wheat forage and hay (ca. 0.12 % pe r day) in frozen storage. The storage stability data support the sample storage intervals and conditions in the submitted crop field trials. Sorghum : Inthe grain sorghum magnitude of residue studies, the maximum frozen storage interval from sampling to extraction of py rasulfotole was 398 day s for forage and 309 day s for grain and stover. For sorghum forage, some samples from the crop field trial were stored for approximately

13 months, which is 2 months longer than the storage duration used in the wheat storage stability

study . However, it is unlikely that a 13 - month storage stability study within thePy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 11 of 28 same cereal grain crop group would differ significantly from the currentl y available 11 - month wheat study. Residues of the metabolite, p yrasulfotole - des methyl, were stable in wheat grain. Py rasulfotole desmethyl residues were found to decline in wheat forage and hay at approximately

0.12 % per day . Therefore, py rasulfotole - desmeth ylresidue values in grain sorghum forage samples were corrected for 46.3% decline based on wheat forage data and py rasulfotole - desmeth ylresidue values in grain sorghum stover were corrected for 46.5% d ecline based on wheat hay

data. Grass : Inthe grass magnitude of residue study , the maximum frozen storage interval from sampl ing to extraction prior to analy sis of py rasulfotole was 349 day s for grass forage and 312 day s for grass hay . It should be noted that some grass forage samples were stored for approximately

2 weeks longer than the length of the storage stability wheat study . However, it is unlikely that storage stability

study extended by

2 weeks would differ significantly from the currentl y available 11 - month wheat study . Residues of the metabolite, py rasulfotole - desmeth yl , however, were found to decline in wheat forag e and wheat hay at approximately

0.12 % per day . Therefore, p yr asulfotole - desmethyl residue values in grass forage samples were corrected for 46.3% decline based on wheat forage data and p yrasulfotole - desmeth ylresidue values in grass hay were corrected for 46.5% decline based on wheat hay data. 860.1480 Meat, Milk, Poultry, and Eggs Table 4 . Calculation of MRDB of Cattle for Pyrasulfotole. Feed Commodity Feedstuff Type 1 % Dry Matter 2 % Diet 2 Proposed or Recommended Tolerances (ppm) MRDB (ppm) 3 Beef/Da iry Cattle (R=15/45% ; CC=80/45% ; PC=5/10% ) Barley grain CC 88 35/0 0.02 0.0080/0 Aspirated grain fractions CC 85 5/0 0.40 0.023/0 Sorghum grain CC 86 40/45 0.70 0.33/0.37 Sorghum forage R 35 15/0 1.5 0.64/0 Grass forage R 25 0/45 25 0/45 Untreated PC NA 5/10 NA - 0 - Total 1.0/4 5 Poultry (CC=75 - 80%; PC=20 - 25% ) Sorghum grain CC - 75 0.70 0.52 Oat grain CC - 5 0.08 0.004 Untreated PC - 20 NA - 0 - Total 0.52 Hogs (CC=80 - 85%; PC=15 - 20%) Sorghum grain CC - 80 0.70 0.56 Wheat milled byproducts CC - 5 0.02 0.0005 Untreated PC - 15 NA - 0 - Total 0.56 1 CC = c arbohydrate concentrate; R = roughage ; PC = p rotein concentrate. 2 Table 1 (860.1000 OPPTS Test Guidelines; June 2008 Revisions of Livestock Diets Percents Reasonable Balanced Diets. 3 Contributio n = [tolerance /% DM (if cattle)] X % diet. Ruminants : No ruminant feeding study was submitted with the subject petition. Permanent tolerances have been establishe d for residues of p yrasulfotole and its metabolite py rasulfotole desmethyl in/on the follo wing livestock commodities: fat and meat of cattle, goats, hogs, horses and sheep at 0.02 ppm; liver of cattle, goats, hogs, horses and sheep at 0.35 ppm; meat by products, except liver, of cattle, goats, hogs, horses and sheep at 0.06 ppm; and milk at 0.0 1 ppm (Memo, J. Tyler, 06/08/07; D328640 ). The results of a ruminant feeding study was submitted and reviewed by HED in the 06/08/07 memo. From the results of that study , HEDPy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 12 of 28 estimated the MRDB using HED - recommended py rasulfotole tolerances. HED calculated that the total dietary

burden from the worst - case diet calculated for dairy cattle was approximately 0.39 ppm and consisted of 20% wheat hay (dietary burden = 0.18 ppm), 25% wheat forage (dietary burden = 0.20 ppm), 45% barley grain (dietary

burden = 0 .01 ppm), 10% untreated. The total dietary

burden from the worst case diet for beef cattle was approximately 0.18 ppm and consisted of 15% wheat forage (dietary burden = 0.14 ppm), 50% barley grain (dietary

burden = 0.01 ppm), 25% wheat grain (dietary burden = 0.006 ppm); 5% aspirated grain fractions (dietary burden = 0.02 ppm); and 5% untreated. Based on these results, and in order to harmonize with PMRA, the aforementioned tolerances were established. The ruminant feed items associated with the subject petition are sorghum grain, forage, and stover; and grass forage and hay . HED recalculated the MRDB for beef and dairy cattle to include these new uses (see Table 4 ). The results of a dairy cattle feeding study

for p yr asulfotole have been submitted and reviewed b y HED (Memo, J. Tyler, 6/8/07; D333412). Based on the results of the livestock metabolism studies, the residues of concern in livestock are py rasulfotole and py

rasulfotole - desmeth ylfor tolerance and risk assessment purposes ( Memo, J. Tyler, 0 6/08/07; D328640 ). However, onl y p yrasulfotole was anal yz ed for in the available dairy cattle feeding study . HED previously assumed the transfer of py rasulfotole - desmeth ylfrom plants to livestock to be equivalent to that of the parent p yr asulfotole base d on the structure similarity and concluded that the available dairy cattle feeding study was thus adequate for tolerance - setting purposes . As the doses used in the dairy cattle feeding study

still bracket the MRDB and p yr asulfotole - desmeth ylcomprised on ly ~15% of the total residue, HED concludes that this feeding study is still adequate for tolerance - setting purposes . However, for an y new uses which significantl y increase the MRDB of p yrasulfotole - desmeth yl , the petitioner may be required to submit a fe eding study in with the desmethyl metabolite. In that study, dosing was conducted at 0 (control), 3, 9, or 30 ppm/day in the feed (dry weight basis); these levels were at 0.067x, 0.2x, and 0.67 x the MRDB to dairy cattle. The 0.67x feeding level is closes t to the actual feeding level of 1x; therefore, it will be used to determined appropriate tolerance s for ruminant commodities (see Table 5 ) . T able 5 . Determination of Appropriate Tolerance for Ruminant Commodities. Matrix Feeding Level

(ppm/day) [exagge ration ] 1 Residues (ppm)

Max Residues in Feeding Study Residues When

Extrapolated to 1x Recommended

Tolerance (ppm) Milk 30 [ 0. 67x] 0.0134 0. 0 200 0.03 Milk Fat 30 [0.67x] 0.0085 0. 0 1 27 0.02 Fat 30 [0.67x] 0.0143 0.0213 0.03 Kidney 30 [0.67x] 0.4144 0.618 0.70 Liver 30 [0.67x] 1.939 2.89 3.0 Muscle 30 [0.67x] 0.0039 0.00582 0.02 1 From previously reviewed lactating dairy cattle feeding study (46801824.der.doc; Memo, J. Tyler, 6/8/07; D333412). R esidues of py

rasu lfotole were ≤ 0.0134 ppm in milk and≤0.0085 (<LOQ) in milk fat , resulting in residues of 0. 0200 ppm and 0.0127 ppm, respectively , when extrapolated to 1x. Residues of py rasulfotole in were ≤ 0.0010 ppm ( <LOQ) muscle and ≤0.0062 ppm (<LOQ) in fat , resulting in residues of 0. 00582 ppm and 0.0213 ppm, respectively , when extrapolated to 1x . Residues of py rasulfotole were ≤1.939 ppm in liver and ≤0.4144 ppm in kidney , resulting in residues of 2.89 ppm and 0.618 ppm, respectivel y, when extrapolated to 1x . Based on these res idues, the c urrent tolerances of 0.02 ppm for meat of cattle, goat, horse and sheep are adequate to support thePy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 13 of 28 proposed uses. However, tolerances should be established for residues of py rasulfotole and py rasulfotole - desmeth ylin/on milk at 0 .03 pp m ; fat o f cattle, goat, horse and sheep at 0.03 ppm; liver of cattle, goat, horse, and sheep at 3.0 ppm; and meat by products, except liver, of cattle , goat, horse, and sheep at 0.70 ppm. A revised Section F should be submitted to include the above tolerances , as well as correct commodity definitions and tolerance expression . Based upon a MRDB of 0.56 ppm for hogs, the 3 - ppm feeding level in the ruminant feeding study is equivalent to 5.3x the MRDB for hogs. At the 5.3x feeding level, the maximum py rasulfotole r esidues were 0.0010 ppm in muscle, 0.2224 ppm in kidney , 1.230 ppm in liver, and 0.0062 ppm in fat. Residues at the 1x feeding level would be 0.00019 ppm in muscle, 0.042 ppm in kidney , 0.23 ppm in liver, and 0.0012 ppm in fat. There is no reasonable exp ectation of finding quantifiable residues of p yrasulfotole and pyrasulfotole - desmeth ylin hog muscle and fat ; thus , the current tolerances of 0.02 ppm are adequate. There is reasonable expectation of residues of p yr asulfotole and py rasulfotole - desmethyl i n hog liver and kidney . Therefore, the following tolerances for residues of p yrasulfotole and py rasulfotole - desmethyl are necessary : hog, meat by

products, except liver at 0.05 ppm ; and hog, liver at 0.30 ppm . A revised Section F should be submitted to i nclude the above tolerances , as well as correct commodity definitions and tolerance expression . Poultry : No poultry

feeding study

was submitted with the subject petition. Permanent tolerances have been previously established for residues of py rasulfotol e per se in/on meat, fat and meat b yproducts of poultry at 0.02 ppm; and egg at 0.02 ppm (Memo, J. Tyler, 06/08/07; D328640 ). The calculated MRDB for poultry was approximately

0.058 ppm and consisted of 70% oat grain (dietary

burden = 0.056 ppm), 10% wheat milled by products (dietary

burden = 0.002 ppm), 5% barley , and 10% untreated. Based on these results, the aforementioned tolerances were established. The only poultry feed item associated with the subject petition is sorghum grain. HED recalculated th e MRDB for poultry to in clude this new use (see Table 4 ). The results of a poultry feeding study

for py rasulfotole have been submitted and reviewed by HED (Memo, J. Tyler, 6/8/07; D333412). The results of the study are inadequate to determine the need fo r poultry tolerances as only

residues of py

rasulfotole - benzoic acid were measured in the study . However, because the poultry metabolism studies were conducted for 14 day s, the results of the these studies can be used to determine the need for a new poultry feeding study and/or poultry tolerances. Based on the MRDB of 0.52 ppm for poultry , the phen yl - labeled (8.6 ppm) and py razole - labeled (10.5 ppm) poultry metabolism studies were conducted at 16x and 20 x the MRDB for poultry , respectively . In the phen yl - labeled study , total residues of py rasulfotole and py

rasulfotole - desmeth ylwere 0.037 ppm in muscle, 0.065 ppm in fat, and 1.557 ppm in liver. Residues of py rasulfotole and py rasulfotole - desmeth ylat a 1x feeding leve l would be 0.0023 ppm in muscle, 0.006 4 ppm in fat, and 0.0 97 ppm in liver. In the p yr azole - labeled study , total residues of py rasulfotole and py rasulfotole - desmeth ylwere 0.018 ppm in muscle, 0.014 ppm in fat, and 1.277 ppm in liver. Residues of py

rasulfotole and py

rasulfotole - desmethyl at a 1 x feeding level would be 0.00 090 ppm in muscle, 0.0007 0 ppm in fat, and 0.0 64 ppm in liver. Inboth radiolabeled studies, as the total extractable residues in eggs were < 0.01 ppm; the samples were not analyzed further for identification purposes. Bas ed on the results of the poultry metabolism study , there is no reasonable expectation of finding quantifiable residues of py rasulfotole and py

rasulfotole desmethyl in eg gs and poultry muscle and fat. Thus, the established tolerances of 0.02 ppm forPy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 14 of 28 residu es of p yr asulfotole and py rasulfotole - desmethyl in fat, meat, and meat by products of poultry are adequate . There is reasonable expectation of residues of py rasulfotole and py rasulfotole - desmeth ylin poultry meat b yproducts. Therefore, a tolerance of 0.20 ppm for residues of p yr asulfotole and py rasulfotole desmethyl in poultry by products is necessary . A revised Section F should be submitted to include the above tolerances and correct tolerance expression. 860.1500 Crop Field Trials 47815001.der.doc ( gr ass grown for seed ) ; Memo, T. Goodlow, 8/17/10, D380769 47815002.der.doc ( grain sorghum) ; Memo, T. Goodlow, 8/17/10, D380769 Grain Sorghum Table 6 . Summary of Residue Data from Crop Field Trials with Pyrasulfotole. Matrix Total Applic.

Rate (lb a.i./A) PHI 1 (days) Residue Levels 2,3 (ppm) N Min. Max. HAFT 4 Median Mean Std. Dev. Pyrasulfotole Sorghum Forage 0.077 - 0.080 (~1x) 0 24 1.097 5.741 5.080 2.167 2.286 1.062

5 to 8 24 0.014 0.462 0.454 0.069 0.133 0.145 ECH ( 32 to 82) 28 <0.01 0.124 0.123 <0.01 0.026 0.034 Sorghum Grain 56 to 60 24 <0.01 0.151 0.143 0.028 0.041 0.037 Sorghum Stover 56 to 60 24 <0.01 0.035 0.030 0.011 0.015 0.007 Pyrasulfotole - des methyl Sorghum Forage 0.077 - 0.080 (~1x) 0 24 0.029 0.346 0.343 0.137 0.164 0.266

5 to 8 24 0.074 0.499 0.479 0.199 0.231 0.359 ECH ( 32 to 82) 28 <0.01 0.380 0.371 0.050 0.108 0.236 Sorghum Grain 56 to 60 24 <0.01 0.185 0.180 0.056 0.076 0.058 Sorghum Stover 56 to 60 24 <0.01 0.390 0.351 0.129 0.152 0.098 Total Pyrasulfotole Sorghum Forage 0.077 - 0.080 (~1x) 0 24 1.184 6.021 5.356 2.419 2.449 1.10

5 to 8 24 0.097 0.902 0.881 0.300 0.364 0.241 ECH ( 32 to 82) 28 <0.02 0.504 0.494 0.043 0.135 0.160 Sorghum Grain 56 to 60 24 <0.02 0.325 0.322 0.089 0.117 0.092 Sorghum S tover 56 to 60 24 <0.02 0.420 0.383 0.142 0.166 0.103 1 ECH = e arliest commercial harvest 2 LLMV = 0.01 ppm for each analyte . LOD for pyrasulfotole = 0.0009 ppm for forage, 0.0019 ppm for grain, 0.0033 ppm for stover. LOD for py

rasulfotole - desmethyl = 0.0011 ppm for forage, 0.0025 ppm for grain, and 0.0014 ppm for stover. Residues in parentheses are between the LOD and LLMV. 3 Total (ppm) = s um of py rasulfotole (ppm) and pyrasulfotole - desmethyl (ppm). LLMV (0.01 ppm) was used when values were <LLMV. 4 HAFT = h ighest - average f ield trial . Baye r CropScience has submitted field trial data for the product Huskie TM H erbicide on grain sorghum . Twelve trials were conducted in the United States during the 2008 growing season. The trials encompassed NAFTA Growing Zones 2 (1 trial in GA ) , 4 (1 trial in MS), 5 (1 trial each in IN, IA, OH, MN), 6 (1 trial each in OK, TX ), 7 (1 trial in ND), and 8 (l trial each in CO, OK, TX). Each site consisted of one control plot and two treatment plots, with one treatment plot for sampling forage and one for sampling grain and stover. The treatment plots each received two applicatio ns of the formulated product at a target rate of 0.039 lb py rasulfotole/A/ application ( 1x the maximum proposed single application rate ). Actual total application ratesPy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 15 of 28 ranged from 0.077 to 0.080 lb ai/A/season (1x the maximum proposed seasonal rate) . Th e retreatment interval ( RTI ) ranged from 11 to 16 day s and the spray volumes ranged from 12 to 20 gal/A. An adjuvant was not used in the spray applications . Sorghum forage samples were collected at target PHIs of 0 and 7 day s and also at earliest commerc ial harvest (ECH) (BBCH 81, beginning of ripening, to BBCH 87, hard dough), which corresponded to PHI s of 32 to 82 day s. Sorghum grain and stover samples were collected at a target PHI of 60 day s. A residue decline trial was also conducted at one site, in which forage samples were collected at PHIs of 0, 1, 3, 7, 10, and 14 day s with additional samples collected at five intervals before, at, and after earliest commercial harvest (ECH - 14, ECH - 7, ECH, ECH+7, and ECH+14 day s; actual PHIs were 18, 25, 32, 39 , and 46 day s) . Grain and stover samples were collected at five intervals corresponding to target PHI s of 47, 53, 60, 67, and 74 day s. After two applications of Huskie TM Herbicide to grain sorghum at a total rate of 0.077 to 0.080 lb ai/A (~1x the maximum proposed seasonal rate) for py rasulfotole, residues of total py rasulfotole (sum of py

rasulfotole and py

rasulfotole - desmeth yl) in the forage samples ranged from 1.18 ppm to 6.02 ppm at a PHIof 0 day s, from 0.097 ppm to 0.902 ppm at a PHI of 5 to 8 day s, and from <LLMV (0.02 ppm) to 0.504 ppm at ECH (PHIof 32 to 82 day s). Residues in grain and stover samples collected at a PHI of 56 to 60 day s from plots treated at a to tal rate of 0.077 to 0.080 lb ai/A ranged from below the LLMV (0.02 ppm) to 0.325 ppm and from <0.02 to 0.420 ppm, respectivel y. Residue decline data showed that residues of p yrasulfoto le, py rasulfotole - desmethyl de creased with time in/on grain sorghum earl y forage . The residues also generall y decreased with time in/on sorghum forage collected around earliest commercial harvest (ECH - 14 day to ECH +14 day), however, a spike in residues was observed at the ECH - 7 day interval . In/on sorghum stover, the residues increased with time . In/on sorghum grain, residues of pyrasulfotole and py rasulfotole - desmeth yldecreased with time. HED Conclusions: The submitted grain sorghum residue data are classified as scientificall y acceptable for determination of the magnitude of residue of p yrasulfotole and pyrasulfotole desmethyl in grain sorghum. As the number and geographical representation of the trials are the same as the number and geographical locations recommended in OPPTS Guideline 860.1500, the residue data are adequate to support the proposed uses. The submitted field trial data reflect the use of Huskie TM Herbicide on grain sorghum . In the trials, two applications of Huskie TM Herbicide were applied to each treatment plot at a total seasonal rate of 0. 078 lb py rasulfotole/A/season (1x the proposed rate). Forage samples were collected at a target 0 - and 7 - day PHIs, as well as at ECH (PHI of 32 to 82 day s). Grain and stover samples were co llected at a target 60 - day PHI . A residue decline trial was also conducted at one site, in which forage samples were collected at PHI s of 0, 3, 7, 10, and 14 day s with a dditional samples collected at five intervals of ECH - 14, ECH - 7, ECH, ECH+7, and ECH+14 day s (actual PHI s were 18, 25, 32, 39, and 46 days) . Grain and stover samples were collected at five intervals corresponding to target PHIs of 47, 53, 60, 67, and 74 days . Based on concurrent recoveries, acceptable analy tical methods were used. Adequate storage stability data are available; however, residues of p yrasulfotole - desmethyl were found to decline in wheat forage and hay at approximately 0.12 % per day . Theref ore, py rasulfotole - desmethyl residue values in grain sorghum forage samples were corrected for 46.3% decline based on wheat forage data and py rasulfotole - desmeth ylresidue values in grain sorghum stover were corrected for 46.5% decline based on wheat hay

d ata.Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 16 of 28 With the use pattern in this study , total residues of py rasulfotole in/on grain sorghum forage are not expected to exceed 6.02 ppm (0 - day PHI), 0.902 ppm (7 - day

PHI), or 0.504 ppm (ECH). In/ on sorghum grain and stover (60 - day PHI ), total residues o f p yr asulfotole is not expected to exceed 0.325 ppm or 0.420 ppm, respectivel y. Using the NAFTA MRL/Tolerance Harmonization Workgroup methodology for forage (7 - day

PHI ) , grain, and stover, the available grain sorghum crop field trial data indicate that th e appropriate tolerances for residues of py rasulfotole and py

rasulfotole - desmeth ylin/on grain sorghum grain commodities are 1.5 ppm for sorghum, grain, forage; 0.70 ppm for sorghum, grain, grain; and 0.80 ppm for sorghum, grain, stover (see Sectio n 860.15 50 Proposed Tolerances). Section F of the petition should be revised to include the aforementioned HED - recommended tolerances and the correct commodity definitions for grain sorghum RACs. Grass Grown for Seed Table 7 . Summary of Residue Data from Crop Field Trials with Pyrasulfotole. Matrix Total Applic. Rate

(lb a.i./A) PHI

(days) Residue Levels 1,2 (ppm)

N Min. Max. HAFT 3 Median Mean Std. Dev. Pyrasulfotole Grass Forage 0.076 - 0.091 (~1x) 0 24 0.055 6.51 6.39 1.83 2.54 2.11

7 - 11 26 <0.01 6.3 2 6.21 0.079 1.33 2.09 Grass Hay 0.077 - 0.080 (~1x) 28 - 31 24 <0.01 1.71 1.69 0.0183 0.202 0.472 Pyrasulfotole - des methyl Grass Forage 0.076 - 0.091 (~1x) 0 24 0.045 0.631 0.619 0.182 0.234 0.181

7 - 11 26 0.041 0.544 0.512 0.205 0.234 0.146 Grass Hay 0.077 - 0.080 (~1x) 28 - 31 24 <0.01 0.607 0.574 0.112 0.186 0.172 Total Pyrasulfotole Grass Forage 0.076 - 0.091 (~1x) 0 24 0.132 6.77 6.75 2.49 3.14 2.20

7 - 11 26 0.062 6.52 6.40 0.317 1.56 2.09 Grass Hay 0.077 - 0.080 (~1x) 28 - 31 24 <0.02 2.31 2.27 0 .157 0.390 0.611 1 LLMV = 0.01 ppm for each analyte . LOD for pyrasulfotole = 0.00353 ppm for forage and 0.00162 for hay. LOD for pyrasulfotole - desmethyl = 0.00521 ppm for forage and 0.00132 ppm for hay. Residues in parentheses are between the LOD and L LMV. 2 Total (ppm) = s um of py rasulfotole (ppm) and pyrasulfotole - desmethyl (ppm). LLMV (0.05 ppm) was used when values were <LLMV. 3 HAFT = highest - average f ield trial . Baye r CropScience has submitted field trial data for the product Huskie TM Herbicide on grass grown for seed (Bermuda, bluegrass, and fescue). Twelve trials were conducted in the United States and Canada during the 2008 growing season. The trials encompassed NAFTA Growing Zones 1 (1 trial in Atlantic Provinces, Canada) , 2 (1 trial in GA), 3 (1 trial in FL), 4 (1 trial in AR), 5 (1 trial in WI ; 1 trial in NE), 9 (1 trial in ID), 10 (1 trial in CA), 11 (1 trial in ID; 1 trial in WA), and 12 (1 trial in British Columbia, Canada; 1 trial in OR). Each site consisted of one control plot and two treatment plots, with one treatment plot for sampling forage and one for sampling hay . The treatment plots each received two broadcast foliar applications of the formulat ed product at a target rate of 0 .039 lb py rasulfotole/A/application (~1x the maximum proposed single application rate ). Actual total application rates ranged from 0.076 to 0.091 lb ai/A/season (~1x the maximum proposed seasonal application rate) with a 27 - to 30 - day RTI .Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 17 of 28 Spray volumes ranged from 10 to 24 gal/A. An adjuvant was not used in the spray applications. Grass forage samples were collected at target PHI of 0 day s and 7 day s. Grass hay samples were collected at a target PHI of 30 day s. A residue decline trial was also conducted at one site, in which forage samples were collect ed at PHIs of 0, 1, 3, 7, 10, and 14 day s and hay samples were collected at PHIs of 20, 25, 30, 36, and 40 day s. After two applications of Huskie TM Herbicide to grass at a total rate of 0.076 to 0.091 lb ai/A (~1x the maximum proposed seasonal rate) , residues of py rasulfotole in/on the grass forage samples ranged from 0.055 ppm to 6.51 ppm at a PHI of 0 day s and from below the LLMV (<0.01 ppm) to 6. 32 ppm at a PHIof 7 to 11 day s. Residues of py rasulfotole - desmeth yl in/on the grass forage samples ranged from 0.045 ppm to 0.631 ppm at a PHI of 0 day s and from 0.041 ppm to 0.544 ppm at a PHI of 7 to 11 day s. Total py rasulfotole residues in/on the forage samples ranged from 0.132 ppm to 6.77 ppm at a PHIof 0 day s and from 0.062 ppm to 6.52 ppm at a PHI of 7 to 11 day s. P yr asulfotole residues in/on grass hay samples, collected at a PHI of 28 to 31 day s from plots treated with Huskie TM Herbicide a total rate of 0.076 - 0.091 lb ai/A, ranged from below the LLMV to 1.71 ppm. Residues of py rasulfotole - desmethyl in/on the grass hay samples ranged from below the LLMV to 0.607 ppm and total py rasulfotole residues ranged from below the LLMV (<0.02 ppm) to 2.31 ppm. Residue decline data showed that residues of p yrasulfotole and metabolites decreased with time in grass forage and hay . A slight increase in py rasulfotole residues was observed in grass hay between the 30 and 35 day PHI interval. HED Conclusions : The submitted grass residue data are classified as scientifically acceptable for determination of the magnitude of residue of py rasulfotole and py

rasulfotole - desm eth ylin grass grown for seed. The submitted field trial data reflect the use of Huskie TM H erbicide on grass grown for seed . In the trials, two applications of Huskie TM H erbicide was applied to each treatment plot at a total seasonal rate of 0.076 to 0.091 lb ai/A . Forage samples were collected at a target 0 - and 7 - day PHI and hay

sample s were collected at a target 30 - day PHI . Decline trials were also conducted in which sample collection occurred at PHIs of 0, 1, 3, 7, 10 and 14 day s for forage and 20, 25, 30, 35, and 40 day s for hay . Based on concurrent recoveries, accepta ble analy tical methods were used. Storage stability

data from grass, wheat, and/or barley demonstrate that residues of py rasulfotole is stable in grass forage and hay under the storage conditions used in this study ; however, residues of p yr asulfotole - desm eth ylwere found to decline in wheat forage and hay at approximately

0.12 % per day . Therefore, py rasulfotole - desmeth ylresidue values in grass forage samples were corrected for 46.3% decline based on wheat forage data and py rasulfotole desmethyl residue v alues in grass hay samples were corrected for 46.5% decline based on wheat hay data. With the use pattern in this study , total residues of py rasulfotole, are not expected to exceed 6.73 ppm (0 - day

PHI) or 6.52 ppm (7 - day PHI) in/on grass forag e and 2.31 p pm in grass hay (30 - day PHI). Using the NAFTA MRL/Tolerance Harmonization Workgroup methodology for grass forage (7 - day PHI ) and hay , the available grass crop field trial data indicate that the appropriate tolerances for residues of py rasulfotole and py

ra sulfotole - desmeth ylin/on are 25 ppm for grass, forage; and 3.5 ppm for grass, hay (see Section 860.1550 Proposed Tolerances) . Section F of the petition should be revised to include the aforementioned HED - recommended tolerances .Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 18 of 28 In addition, the proposed label does not specify application equipment or a minimum spray volume for application to grass grown for seed. The submitted data support ground foliar applications made in spray volumes of 10 - 24 gal/A. A revised label should be submitted to include th ese use directions. 860.1520 Processed Food and Feed As there are no processed commodities associated with the proposed uses, processing studies are not required. 860.1650 Submittal of Analytical Reference Standards Analy tical reference standards for py rasulfotole have been received b y the EPA National Pesticide Standard Repository for distribution to State and Federal regulatory labs (personal communication between J. Tyler and T. Cole, 9/15/10). However , the Repository has not received reference st andard for the desmethyl metabolite and labeled internal standards. Th ese standards should be sent to the Analy tical Chemistry

L ab to the attention of either The resa Cole or Dallas Wright at the following address: USEPA National Pesticide Standards Repos itory /Anal yt ical Chemistry

Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755 - 5350 The extended zip code must be used or the mail will be returned. 860.1850 and 860.1900 Confined/Field Accumulation in Rotational Crops No rotational crop data were submitted in conjunction with the proposed uses. According to the current guidance, grain sorghum and grass grown for seed are considered to be rotated crops. The following rotational crop restrictions are currently on the proposed label : Wheat, barley , oats, rye and triticale 1 month Alfalfa * , millet, sorghum (grain), and soybeans 4 months Canola, canaryseed, chickpeas, corn, dry beans, flax, field peas, green beans, green peas, lentils ** , mustards, potatoes, safflower, sunflowers, and sugar beets 9 mo nths All other crops 30 days *** * Thorough tillage prior to planting alfalfa and a minimum of 12 inches of rainfall, overhead, furrow or flood irrigation or any combination of these water source totaling 12 inches is required between the time following a Huskie TM Herbicide application and the time of alfalfa seeding. ** Lentils: 9 months for all states except 18 months in MN, MT, ND, and SD. *** Where a crop is not specified, conduct a field bioassay as described in “FIELD BIOASSAY” section of proposed lab el. A dequate confined and field rotational crop data have been submitted by the petitioner and reviewed by

HED in conjunction with PP#6 F 7509 (Memo, J. Tyler, 6/8/07 , D 366490 ). ThePy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 19 of 28 results of the submitted confined and limite d field rotational crop studie s together are adequate to determine appropri ate PBIs for rotational crops. In the confined rotational crop study , following application of either phenyl - or p yr azole - labeled py rasulfotole, the TRR in the 122 - day s after treatment (DAT) Swiss chard , turnip tops, and turnip roots were <0.01 (<LOQ). In the limited field rotational crop study , m aximum residue levels of py rasulfotole and pyrasulfotole - desmeth yl were <LOD in all corn and soy bean RACs at PBIs of 114 - 123 day s . Maximum residues levels for p yrasul fotole - benzoic acid were 0.0018 ppm in corn forage, 0.0027 ppm in soy bean forage, 0.0126 ppm in soy

bean hay and <LOD in corn grai n, corn stover and so yb ean seed . However, it was determined that residues of p yrasulfotole - benzoic acid are not of concern for both tolerance and risk assessment purposes (Memo, J. Tyler et al . , 06 / 08 /07; D328640) . In addition, HED approved a requested to revise the Crop Rotation Guidelines on the currently approved Huskie TM Herbici de (EPA Reg. No. 264 - 1023) label as follows: 1) an increased PBI from 7 day s to 1 month for wheat, barley , oats, rye, and triticale; 2) an addition of green beans and green peas to the 9 - month PBI ; and 3) a decreased PBI for alfalfa from 9 months to 4 months. Therefore, the submitted confined and limi ted field trial data support the proposed PBIs . 860.1550 Proposed Tolerances A summary

of the recommended tolerances and the correct commodity definitions for the pro pose d uses are listed in Table 8 . The available crop field trial data on grain sorghum and grass grown for seed are adequate to support the proposed uses of py rasulfotole. For purposes of determining appropriate tolerance levels for the proposed uses, individual py rasulfotole and py

rasulfotole - desmethyl residues were summ ed to yield a to tal residue value. Appropriate tolerances where determined using the methodology

formulated by

the NAFTA MRL/Tolerance Harmonization Workgroup for calculating statistically- based pesticide tolerances for plant commodities base d on field trial residue data . Using the 0.67x data from the adequate cattle feeding study and a calculated MRDB of 45 ppm for p yrasulfotole and p yr asulfotole - desmeth ylresidues in dairy cattle diets, estimated py rasulfotole and p yr asulfotole - desmeth ylresidues in rumin ants at a 1x d ose level are 0.0200 ppm in milk; 0.00127 ppm in milk fat; 0.0213 ppm in fat; 0.00582 ppm in muscle; 2.89 ppm in liver; and 0.618 ppm in kidney . Base d on the quantifiable residues, tolerances should be established for residues of py rasulfotole and py

rasul fotole - desmeth ylin/on milk at 0.03 ppm; fat of cattle, goat, horse and sheep at 0.03 ppm; liver of cattle, goat, horse, and sheep at 3.0 ppm; and meat b yproducts, except liver, of cattle , goat, horse, and sheep at 0.70 ppm. Although, there is no reasonab le expectation of finding quantifiable residues of p yr asulfotole and py rasulfotole desmethyl in muscle of cattle, goat, horse and sheep, the current tolerances for these commodities (established in order to harmonize with PMRA ) are ade quate to support the proposed uses on grain sorghum and grass grown for seed. Using data from the adequate cattle f eeding study and a calculated MRD B of 0.56 ppm py rasulfotole and py

rasulfotole - desmeth ylin hogs, the estimated py rasulfotole and py

rasulfotole desmethyl residue s in hogs were 0.00019 ppm in muscle, 0.042 ppm in kidney , 0.23 ppm in liver , and 0.0012 ppm in fat . There is no reasonable expectation of finding quantifiable residuesPy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 20 of 28 of py rasulfotole an d py

rasulfotole - desmeth ylin muscle and fat; however, the current t olerances of 0.02 ppm (established in order to harmonize with PMRA) are adequate to support the proposed uses on grain sorghum and grass grown for seed. There is reasonable expectation of residues of p yr asulfotole and py rasulfotole - desmethyl in hog liver and kidney . Therefore, the following tolerances for residues of p yrasulfotole and pyrasulfotole desmethyl are necessary : hog, meat by

products, except liver at 0.05 ppm; and hog, liver at 0.30 ppm. U sing the data from the poultry metabolism studies and a calculated MRDB of 0.52 ppm for poultry , the maximum estimated py rasulfotole and py

rasulfotole - desmeth ylresidues in poultry were 0.0023 ppm in muscle, 0.0070 ppm in fat, and 0.097 ppm in liver. A s the total extractable residues in eggs were <0.01 ppm; the samples were not anal yz ed further for identification purposes. Based on the results of the poultry metabolism study , there is no reasonable expectation of finding quantifiable residues of p yr asulfotole and p yrasulfotole - desme thyl in eggs and poultry

mu scle and fat; however , the current tolerances of 0.02 ppm (established in order to harmonize with PMRA ) are adequate to support the proposed uses on grain sorghum and grass grown for seed. There is reasonable expectation of residues of py rasulfotole and p yrasulfotole desmethyl in poultry

meat by products. Therefore, a tolerance of 0.20 ppm for residues of py rasulfotole and py

rasulfotole desmethyl in poultry by products is necessary . The residue chemistry database supports the establishment of the permanent tolerances for the combined residues of py

ra sulfotole and p yrasulfotole - desmeth yl i n/on the RACs and livestock commodities listed in Table 8 . Section F should be revised to include these recommended tolerances as well as the correct tolerance expression for livestock commodities. Table 8 . Tolerance Summary for Pyrasulfotole.

Commodity Current Tolerance (ppm) Proposed

Tolerance (ppm) Recommended

Tolerance (ppm) Comments ( correct commodity definition ) Sorghum, grain - 0.8 0.70 Sorghum, grain, grain Sorghum, forage - 1.2 1.5 Sorghum, grain, forage Sorghum, stover - 0.35 0.80 Sorghum, grain, stover Grass, forage - 10 25 Grass, hay - 2.5 3.5 Milk * 0.01 0.01 0.03 Cattle, meat 0.02 0.04 see current tolerance Cattle, fat * 0.02 0.04 0.03 Cattle, me at byproducts * 0.06 2 0.70 Cattle, meat byproducts, except liver Cattle, liver * 0.35 8 3 .0 Goat, meat 0.02 0.04 see current tolerance Goat, fat * 0.02 0.04 0.03 Goat, meat byproducts * 0.06 2 0.70 Goat, meat byproducts, except liver Goat, liver * 0.35 8 3 .0 Hog, meat 0.02 0.04 see current tolerance Hog, fat 0.02 0.04 see current tolerance Hog, meat byproducts * 0.06 2 0.05 Hog, meat byproducts, except liver Hog, liver * - 8 0.30 Sheep, meat 0.02 0.04 see current tolerance Sheep, fat * 0.02 0.04 0.03 Sheep, meat byproducts * 0.06 2 0.70 Sheep, meat byproducts, except liverPy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 21 of 28 Table 8 . Tolerance Summary for Pyrasulfotole.

Commodity Current Tolerance (ppm) Proposed

Tolerance (ppm) Recommended

Tolerance (ppm) Comments ( correct commodity definition ) Sheep, liver * 0.35 8 3 .0 Horse, meat 0.02 0.04 see current tolerance Horse, fat * 0.02 0.04 0.03 Horse, meat byproducts * 0.06 2 0.70 Horse, meat byproducts, except liver Horse, liver * 0.35 8 3 .0 Poultry, meat 0.02 - see current tolerance Poultry, fat * 0.02 - 0.0 2 Poultry, meat byproducts * 0.02 - 0.20 Eggs 0.02 - see current tolerance * Livestock commodities with tolerances that are not harmonized with PMRA. T he International Residue L imit Status (IRL S) Sheet is attached as Attachment 1. There are no established Mexican or Codex MRL s for the proposed uses. There are Canadian MRL s establis h ed for livestock commodities. However, due to the recommended toleranc es on the proposed uses, there was an increase in MRDB for livestock commodities. This resulted in the need for an increase in tolerances for several livestock commodities (see commodities with asterisk in Table 8). Therefore, harmonization is not possib le at this time. Attachments Attachment 1: IRL S Sheet. Attachment 2: Inputs for calculating statistically- based pesticide tolerances.

cc: J. Tyler (RAB1) RDI: RAB1 Chemists (9 /29/10 ), G. Kramer ( 9 /2 7 / 1 0) J. Tyler: S - 10943: Potomac Yard: (703) 305 - 5564: RAB1Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 22 of 28 Attachment 1. IRLS Sheet. 

### International Residue Limits

Pyrasulfotole (000692; 15 - SEP - 2010) Summary of US and I

nternational Tolerances and Maximum Residue Limits Residue Definition : US Canada Mex ico 2 Codex 40 CFR 180.631: Plant/Livestock: pyrasulfotole and pyrasulfotole desmethyl, (5 - hydroxy - 1,3 - dimethyl - 1 H - pyrazol - 4 - yl)[2 - (methylsulfonyl) - 4 - (trifluoromethyl)phenyl]methanone, and its metabolite, 5 - hydroxy - 3 - methyl - 1 H - pyrazol - 4 - yl) [2 - methylsulfo rnyl) - 4 - (trifluoromethyl)phenyl]methanone (5 - hydroxy- 1,3 - dimethyl - 1 H - pyrazol - 4 - yl)[2 - (methylsulfonyl) - 4 - (trifluoromethyl)phenyl]methanone, including the metabolite (5 - hydroxy- 3 - methyl - 1 H

- py razol - 4 - yl)[2 - (methylsulfonyl) - 4 - (trifluoromethyl)phenyl]methanone None

Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex Sorghum, grain 0.7 Sorghum, forage 1.5 Sorghum, stover 0.8 Grass, forage 10 Grass, hay 3.5 Milk 0.1 0.01 Cattle, meat 0.02 0.02 Cattle, fat 0.02 0.02 Cattle, meat byproducts, except liver 1.0 0.06 Cattle, liver 4.0 0.35 Goat, meat 0.02 0.02 Goat, fat 0.02 0.02 Goat, meat byproducts, except liver 1.0 0.06 Goat, liver 4.0 0.35 Hog, meat 0.02 0.02 Hog, fat 0.02 0.02 H og, meat byproducts, except liver 0.05 Meat byproducts of hogs 0.02 Hog, liver 0.30 Sheep, meat 0.02 0.02 Sheep, fat 0.02 0.02 Sheep, meat byproducts, except liver 1.0 0.06 Sheep, liver 4.0 0.35 Horse, meat 0.02 0.02 Horse, fat 0.02 0 .02 Horse, meat byproducts, except liver 1.0 0.06 Horse, liver 4.0 0.35 Poultry, meat 0.02 0.02 Poultry, fat 0.02 0.02 Poultry, meat byproducts 0.20 0.02 Eggs 0.02 0.02 Completed: M. Negussie; 09/16/2010 1 In cludes only commodities o f 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.Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 23 of 28 Attachment 2. Inputs for calculating statistically - based pe sticide tolerances. Grass Forage – 7 - day PHI Regulator: EPA Chemical: Pyrasulfatole Crop: Grass Forage PHI: 7 days App. Rate: 0.076 - 0.091 lb ai/A Submitter: Residues LN(Residues) Z scores 0.264 - 1.33 - 0.53 0.279 - 1.28 - 0.41 5.6 2 1.73 1.19 4.635 1.53 0.98 1.27 0.24 0.29 1.204 0.19 0.17 0.147 - 1.92 - 0.98 0.133 - 2.02 - 1.19 6.278 1.84 1.45 6.523 1.88 1.91 3.571 1.27 0.67 3.829 1.34 0.81 1.587 0.46 0.41 1.686 0.52 0.53 0.259 - 1.35 - 0.67 0.193 - 1.65 - 0.81 0 .062 - 2.78 - 1.91 0.064 - 2.75 - 1.45 0.311 - 1.17 - 0.17 0.319 - 1.14 0.06 0.304 - 1.19 - 0.29 0.315 - 1.16 - 0.06 Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 7.0000 3.5000 1.7500 0.8750 0.4375 0.2188 0.1094 0.0547 y = 1.5259x - 0.3967 R 2 = 0.9279

PercentilesConcentrations EPA Pyrasulfatole Grass Forage 7 days 0.076 - 0.091 lb ai/APy

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 24 of 28 Reg ulat or: EP A Chemic al: Py rasu lfato le Cr op: Gr ass Forag e PH I: 7 days App . Ra te: 0. 076 - 0.0 91 l b ai/ A Sub mitt er:

n: 22 mi n: 0.0 6 max: 6.5 2 medi an: 0.3 2 avera ge: 1.7 7 95th Per centi le 99th Percentile 99.9 th Pe rcen tile 6. 0 7.0 9. 0 (7. 0) (9.0) (--) 9. 0 25 80 (25) (95 ) (--) 8.0 9.0 1.7 0.92 79 p- valu e > 0.05 : Do not reje ct l ogno rmali ty a ssump tion Appr oxima te Sh apir o-Fra ncia Norm alit y Tes t EU M ethod I Norm al

UC LMe dian9 5th 95 /99 Rule EU Meth od II Dis trib ution -Fre e Me an+ 3SD Grass Hay Regulator: EPA Chemical: Pyrasulfatole Crop: Grass Hay PHI: 29 - 31 days App. Rate: 0.077 - 0.080 lb ai/A Submi tter: Residues LN(Residues) Z scores 0.148 - 1.91 - 0.05 0.166 - 1.80 0.05 0.375 - 0.98 0.60 0.348 - 1.06 0.48 2.315 0.84 1.95 2.217 0.80 1.50 0.141 - 1.96 - 0.16 0.126 - 2.07 - 0.37 0.096 - 2.34 - 0.48 0.067 - 2.70 - 0.73 0.131 - 2.03 - 0.26 0.253 - 1.37 0.37 0.02 - 3.91 - 1.95 0.032 - 3.44 - 1.50 0.068 - 2.69 - 0.60 0.065 - 2.73 - 0.88 0.548 - 0.60 1.04 0.864 - 0.15 1.24 0.045 - 3.10 - 1.24 0.055 - 2.90 - 1.04 0.416 - 0.88 0.73 0.437 - 0.83 0.88 0.207 - 1.58 0.16 0.212 - 1.55 0.26Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 25 of 28 Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 3.0000 1.5000 0.7500 0.3750 0.1875 0.0938 0.0469 0.0234 0.0117 y = 1.2413x - 1.7061 R 2 = 0.9771

PercentilesConcentrations EPA Pyrasulfatole Grass Hay 29-31 days 0.077 - 0.080 lb ai/A

Regulator: EPA Chemical: Pyrasulfatole Crop: Grass Hay PHI: 29-31 days App. Rate: 0.077 - 0.080 lb ai/A Submitter:

n: 24 min: 0.02 max: 2.32 median: 0.16 average: 0.39 95th Percentile 99th Percentile 99.9th Percentile 1.4 1.9 2.5 (1.9) (2.5) (--) 1.4 3.5 8.0 (3.5) (9.0) (--) 0.90 2.5 0.90 0.9771 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD Sorghum Forage Regulator: EPA Chemical: Pyrasulfotole Crop: Sorghum

Forage PHI: 5 - 7 days App. Rate: 0.077 - 0.080 lb ai/A Submitter: Residues LN(Resi dues) Z - scores 0.097 - 2.33 - 1.95 0.11 - 2.21 - 1.50 0.119 - 2.13 - 1.04 0.118 - 2.1 4 - 1.24 0.554 - 0.59 0.73 0.474 - 0.75 0.48 0.159 - 1.84 - 0.73 0.127 - 2.06 - 0.88 0.616 - 0.48 0.88 0.549 - 0.60 0.60 0.349 - 1.05 0.16 0.372 - 0.99 0.37 0.229 - 1.47 - 0.37 0.311 - 1.17 0.05 0.86 - 0.15 1.50 0.902 - 0.10 1.95 0.288 - 1.24 - 0.0 5 0.363 - 1.01 0.26 0.24 - 1.43 - 0.16 0.237 - 1.44 - 0.26 0.637 - 0.45 1.04Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 26 of 28 0.674 - 0.39 1.24 0.17 - 1.77 - 0.60 0.173 - 1.75 - 0.48 Lognormal Probability Plot

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 y = 0.7037x - 1.2318 R 2 = 0.9652

PercentilesConcentrations EPA Pyrasulfatole Sorghum Forage 5-7 days 0.077 - 0.080 lb ai/A

Regulator: EPA Chemical: Pyrasulfatole Crop: Sorghum Forage PHI: 5-7 days App. Rate: 0.077 - 0.080 lb ai/A Submitter:

n: 24 min: 0.10 max: 0.90 median: 0.30 average: 0.36 95th Percentile 99th Percentile 99.9th Percentile 0.80 1.0 1.2 (1.0) (1.2) (--) 1.0 1.5 2.5 (1.5) (3.0) (--) 1.2 1.1 1.6 0.9652 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD Sorghum Grain Regulator: EPA Chemical: Pyrasulfotole Crop: Sorghum Grain PHI: 56 - 60 days App. Rate: 0.077 - 0.080 lb ai/A Submitter: Residues LN(Residues) Z scores 0.02 - 3.91 - 1.95 0.02 - 3.91 - 1.50 0.074 - 2.60 - 0.05 0.07 - 2.66 - 0.16 0.191 - 1.66 0.73 0.234 - 1.45 1.24 0.104 - 2.26 0.05 0.116 - 2.15 0.16 0.0621 - 2.78 - 0.26 0.06 - 2.8 1 - 0.37 0.325 - 1.12 1.95 0.32 - 1.14 1.50 0.218 - 1.52 1.04 0.194 - 1.64 0.88 0.02 - 3.91 - 1.24 0.02 - 3.91 - 1.04 0.0359 - 3.33 - 0.73 0.034 - 3.38 - 0.88Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 27 of 28 0.124 - 2.09 0.37 0.118 - 2.14 0.26 0.177 - 1.73 0.60 0.165 - 1.80 0.48 0.0597 - 2.82 - 0. 48 0.0532 - 2.93 - 0.60 Lognormal Probability Plot

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 y = 0.9096x - 2.4864 R 2 = 0.9516

PercentilesConcentrations EPA Pyrasulfatole Sorghum Grain 56-60 days 0.077 - 0.080 lb ai/A

Regulator: EPA Chemical: Pyrasulfatole Crop: Sorghum Grain PHI: 56-60 days App. Rate: 0.077 - 0.080 lb ai/A Submitter:

n: 24 min: 0.02 max: 0.33 median: 0.09 average: 0.12 95th Percentile 99th Percentile 99.9th Percentile 0.30 0.35 0.45 (0.35) (0.45) (--) 0.40 0.70 1.4 (0.70) (1.5) (--) 0.40 0.40 0.50 0.9516 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD Sorghum Stover Regulator: EPA Chemical: Pyrasulfatole Crop: Sorghum

Stover PHI: 56 - 60 days App. Rate: 0.077 - 0.080 lb ai/A Submitter: Residues LN(Residues) Z scores 0.066 - 2.72 - 0.73 0.072 - 2.63 - 0.60 0.136 - 2.00 - 0.37 0.141 - 1.96 - 0.05 0.148 - 1.91 0.16 0.108 - 2.23 - 0.48 0.269 - 1.31 0.88 0.184 - 1.69 0.26 0.28 - 1.27 1.04 0.42 - 0.87 1.95 0.136 - 2.00 - 0.26 0.057 - 2.86 - 1.50 0.137 - 1.99 - 0.16 0.057 - 2.86 - 1.24Py

rasulfotole Summary of Analytical Chemistry and Residue Data D P# 375391

Page 28 of 28 0.142 - 1.95 0.05 0. 058 - 2.85 - 1.04 0.207 - 1.58 0.48 0.236 - 1.44 0.73 0.02 - 3.91 - 1.95 0.06 - 2.81 - 0.88 0.199 - 1.61 0.37 0.21 - 1.56 0.60 0.346 - 1.06 1.50 0.303 - 1.19 1.24 Lognormal Probability Plot

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 y = 0.7318x - 2.0113 R 2 = 0.9424

PercentilesConcentrations EPA Pyrasulfatole Sorghum Stover 56-60 days 0.077 - 0.080 lb ai/A

Regulator: EPA Chemical: Pyrasulfatole Crop: Sorghum Stover PHI: 56-60 days App. Rate: 0.077 - 0.080 lb ai/A Submitter:

n: 24 min: 0.02 max: 0.42 median: 0.14 average: 0.17 95th Percentile 99th Percentile 99.9th Percentile 0.35 0.45 0.50 (0.45) (0.50) (--) 0.45 0.80 1.3 (0.80) (1.4) (--) 0.50 0.50 0.80 0.9424 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD