Page 1 of 15 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY WASHINGTON, D.C. 20460 OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION MEMORANDUM Date : 23 - JAN - 2014 Subject : Saflufenacil in/on Rice and Crayfish. Summary of Analytical Chemistry and

Residue Data . PC Code: 118203 DP Barcodes: D407976 & D409043 Decision Nos.: 472866 & 473447 Registration No: 7969 - 278 Petition No.: 2F8129 Regulatory Action: Sec. 3 Registration Risk Assessment Type: NA Case No.: 7277 T XR No.: NA CAS No.: 372137 - 35 - 4 MRID Nos.: 48945803, 4894580304, 49004101, & 49004102 40 CFR: §180.649 From : George F. Kramer, Ph.D., Senior Chemist

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

RAB1 , HED (7509P) To : Kathryn Montague/Bethany Benbow, PM Team 23

Registration Division (RD; 7505P) Executive Summary Saflufenacil (BAS 800 H) is a broad - spectrum herbicide developed by BASF. It belongs to the herbicide mode - of

- action Group 14 (cell membrane disruptors). Saflufenacil acts through the inhibition of protoporphyrinogen oxidase (PPO), resulting in cell membrane damage and subsequent plant death. Sharpen ® Powered by Kixor Herbicide (EPA Reg. No. 7969 - 278), a 2.85 lb ai/gal suspension - concentrate (SC) formulation, is currently registered for use on legume vegetables (Crop Group 06), the foliage of legume vegetables (Crop Group 07), cereal grains (Crop Group 15, pre - plant/pre - emergence application only), the forage, fodder, and straw of cereal grain s (Crop Group 16, pre - plant/pre - emergence application only), cotton, and sunflower. BASF has submitted a proposal to allow post - emergence application of saflufenacil to rice and to permit crayfish and fish to be grown in the treated rice fields. Shar pen ® is proposed for up to two spray applications with a total maximum application rate of 0.135 lb ai/A, with a maximum of 0.045 lb ai/A applied post - emergence between the 2 - leaf stage and internode elongation. Applications may be made using ground or ae rial equipment, and use of an adjuvant is required.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 2 of 15 BASF has petitioned for the establishment of permanent tolerances under 40 CFR §180.649(a)(1) for saflufenacil, including its metabolites and degradates, in or on the raw agricultural commodities (RACs) listed below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of saflufenacil, 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2 H ) - pyrimidinyl] - 4 - fluoro - N - [[methyl(1 - methylethyl)amino]sul fonyl]benzamide, and its metabolites N - [2 - chloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro - 1(2 H ) - pyrimidinyl) - 4 - fluorobenzoyl] - N ' - isopropylsulfamide and N - [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl]amino}carbonyl)phenyl]urea, calculated as the sto ichiometric equivalent of saflufenacil in/on the following plant commodities:

Grain, cereal, forage, fodder and straw group 16 (except rice straw) 0.1 ppm Rice, straw 0.30 ppm BASF has also petitioned for the establishment of permanent tolerances under 40 CFR §180.649(a)(2) for saflufenacil, including its metabolites and degradates, in or on the agricultural commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only saflufenacil, 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2 H

) - pyrimidinyl] - 4 - fluoro - N - [[methyl(1 - methylethyl)amino]sulfonyl]benzamide, in/on the following commodit ies :

Fish - freshwater finfish 0.01 ppm Fish - shellfish, crustacean 0.01 ppm The previously - submitted metabolism data for corn, soybean, and tomato were adequate to elucidate the nature of the residue in plants resulting from pre - plant/pre - emergence application. The HED Residues of Concern Knowledgebase Subcommittee (ROCKS) determ ined that residues of concern for the tolerance expression and risk assessment consist of saflufenacil, M800H11, and M800H35 (Memo, B. Daiss, 1/6/09; D 359645 ). Subsequently, the petitioner submitted a rice metabolism study following post - emergence foliar application of saflufenacil. The combined residues of saflufenacil, M800H11, and M800H35 (the current residues of concern for the tolerance expression and risk assessment) in rice forage were 71 - 89% of the total radioactive residue (TRR). The only other major metabolite was M800H02, which accounted for 4 - 16% of the TRR in forage. In rice grain, the combined residues of saflufenacil and all metabolites was <10% of the TRR (≤0.01 ppm). HED thus concludes that current tolerance expression adequately accoun ts for the residues of concern following post - emergence foliar application to rice. Additional metabolism data may be required to support foliar application to non - grass crops. The nature of the residue in livestock is adequately understood based on acc eptable metabolism studies conducted on lactating goats and laying hens. Rice straw is not a regulated commodity. Rice grain is thus the only livestock feedstuff associated with the proposed use. As the existing tolerance for residues in/on rice grain ( as a member of cereal grains Crop Group 15) is unaffected by the proposed new use pattern, no changes in the existing tolerances for livestock commodities are needed. The petitioner has submitted two liquid chromatography/mass spectroscopy/mass spectrosco py (LC - MS/MS) analytical methods for the determination of residues of the parent and its metabolites in/on plant and livestock commodities. BASF Method D0603/02 was developed for determination of residues of saflufenacil and its metabolites M800H11 and M8 00H35 inSaflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 3 of 15 different plant matrices using LC - MS/MS. The limit of quantitation (LOQ) was 0.01 ppm for each analyte in food matrices (human consumption) and 0.025 ppm for each analyte in feed matrices (livestock consumption). This method was used as the data - collection method in the analysis of samples for residues of concern from rice studies submitted with the current petition (studies included adequate method validation data). BASF analytical Method No. L0073/01 is the current enforcement method for deter mination of saflufenacil in livestock matrices using LC MS/MS. Samples of crayfish were analyzed with a simplified version of this method which omitted the clean - up step. The method was adequate for data collection based on acceptable method validation a nd concurrent recovery data. Apparent residues of saflufenacil were below the LOQ in/on all samples of untreated water and crayfish. BASF Method L0073/01 is thus suitable as an enforcement method for crayfish. The actual analysis dates of the samples fr om the submitted magnitude of residue study in freshwater crayfish were not provided. Based on the sample collection dates and the final report date, the estimated storage duration for frozen samples is <125 days. No supporting storage stability data wer e submitted. Sample analysis dates are required to determine the duration of storage. Ruminant storage stability data are available which show that saflufenacil is stable for up to 35 days in ruminant matrices (47128015.der.doc). These data can be translated to crayfish. However, if crayfish samples were stored for more than 35 days, then storage stability data may be required for saflufenacil in crayfish. Provided issues related to storage stability are resolved, the submitted magnitude of saflufenacil residue study in f reshwater crayfish will support the proposed tolerance for residues in/on fish - shellfish, crustacean . In addition, the crayfish magnitude of saflufenacil residue data can be translated to support the proposed tolerance for residues in/on fish - freshwater f infish . The submitted rice field trial data are adequate to fulfill data requirements. Following two broadcast applications of the 342 g ai/L SC formulation of saflufenacil at 0.131 - 0.139 lb ai/A, combined residues (and per - trial averages) of saflufena cil, M800H11, and M800H35 in/on rice grain harvested at a 54 - to 103 - day PHI were all <LOQ (<0.03 ppm). The available data will thus support the proposed use pattern. Since the existing tolerance of 0.03 ppm for residues in/on rice grain (as a member of cereal grains Crop Group 15) is supported by the residue data reflecting the post - emergent use pattern, no changes in the existing tolerances for Crop Group 15 are needed. However, a tolerance is not required for rice straw since it is not a regulated com modity. A revised Section F is requested (see below). The submitted rice processing data are adequate to fulfill data requirements. As the residues in the RAC were <LOQ after treatment at a 5X rate, a separate tolerance for hulls and bran will not be re quired. The previously submitted confined and field rotational crop data are adequate to satisfy data requirements for application rates up to 0.137 lb ai/A (1X). The available data indicate that residues of saflufenacil and its metabolites M800H11 and M 800H35 were each <LOQ in/on all rotational crop matrices at a 120 - day PBI. These data support the labeled rotational crop restriction of 4 months for all non - labeled crops. Regulatory Recommendations and Residue Chemistry Deficiencies Pending submission of a rev ised Section F (see requirements under Proposed Tolerances) and issues related to storage stability in crayfish are resolved (see requirements under StorageSaflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 4 of 15 Stability), there are no residue chemistry issues that wou ld preclude granting the following permanent tolerances for residues of saflufenacil under 40 CFR §180.649(a)(2): Fish - freshwater finfish 0.01 Fish - shellfish, crustacean 0.01 860.1380 Storage Stability Actual analysis dates of the samples from the submitted magnitude of residue study in freshwater crayfish were not provided. No supporting storage stability data were submitted. Sample analysis dates are required to determine the duration of storage. Ruminant storage stability data are availab le which show that saflufenacil is stable for up to 35 days in ruminant matrices (47128015.der.doc). These data can be translated to crayfish. However, if crayfish samples were stored for more than 3 5 days, then storage stability data may be required for saflufenacil in crayfish. 860.1550 Proposed Tolerances The petitioner is requested to submit a revised Section F specifying the tolerances summarized above and in Table 7. A human - health risk assessment is forthcoming in a separate document (DP# 405506 ). Background Saflufenacil is a broad - spectrum herbicide developed by BASF. It belongs to the herbicide mode - of - action Group 14 (cell membrane disruptors). Saflufenacil acts through the inhibition of PPO, resulting in cell membrane damage and subseque nt plant death. Susceptible weeds develop symptoms within hours of application under active growing conditions. Plant death occurs within 3 - 5 days depending upon growing conditions. The chemical structure and nomenclature of saflufenacil and its metabol ites M800H11 and M800H35, and the physicochemical properties of the technical grade of saflufenacil are presented in Tables 1 and 2. Table 1. Saflufenacil and Metabolite Nomenclature. Chemical Structure

Common name Saflufenacil Company experimental name BAS 800 H (synonyms: AC 433 379, BASF Reg. No. 4054449) IUPAC name N ' - [2 - chloro - 4 - fluoro - 5 - (3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro - 1(2 H ) - pyrimidinyl)benzoyl] - N

- isopropyl - N

- methylsulfamide CAS name 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - di oxo - 4 - (trifluoromethyl) - 1(2 H ) - pyrimidinyl] - 4 - fluoro - N - [[methyl(1 - methylethyl)amino]sulfonyl]benzamide CAS registry number 372137 - 35 - 4Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 5 of 15 Table 1. Saflufenacil and Metabolite Nomenclature. End - use product (EP) Sharpen ® Powered by Kixor Herbicide (EPA Reg. No. 7969 - 278 ) ( 2.85 lb ai/gal SC formulation) Chemical Structure

Common name M800H11 Chemical name N - [2 - chloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro - 1(2 H ) - pyrimidinyl) - 4 - fluorobenzoyl] - N

' - isopropylsulfamide Chemical Structure

Common name M800H35 Chemical name N - [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl]amino}carbonyl)phenyl]urea Table 2. Physicochemical Properties of Technical Grade Saflufenacil. Parameter Value Melting point Average = 189.9 ° C, peak max = 193.4 ° C pH 4.43 of 1% solution at 25 ° C Bulk Density (ambient temp.) 0.661 kg/L (free fall), 0.736 kg/L (packed) Water solubility (20 °C) in g/100 mL: 0.0025 in water (pH = 5); 0.0014 in pH 4 buffer; 0.21 in pH 7 buffer; not determined due to degradation in pH 9 buffer Solvent solubility (20 ° C) in g/100 mL: 19.4 acetonitrile; 24.4 dichloromethane; 55.4 N,N - dimethylformamide; 27.5 acetone; 6.55 ethyl acetate; 36.2 tetrahydrofuran; 35.0 butyrolactone; 2.98 methanol; 0.25 isopropyl alcohol; 0.23 toluene; <0.01 1 - octanol; <0.005 n - heptane Vapor pressure at 20/25 °C 20 °C = 4.5 x 10 - 15 Pa 25 °C = 2.0 x 10 - 15 Pa Dissociation constant (pK a ) 4.41 Octanol/water partition coefficient Mean Log P ow = 2.6 (P ow = 368.3) UV/visible absorption spectrum wavelength maximum: λ max = 271.6 nm extinction coefficient: ε = 9709 L/mol - cm Reference : BASF Registration Document Number (DocID) 2005/1026464. 860.1200 Directions for Use BASF has submitted draft labels dated 12/17/12 for the 2.85 lb ai/gal SC formulation (Sharpen ® Powered by Kixor Herbicide (EPA Reg. No. 7969 - 278). Information pertaining to the proposed end - use product is listed in Table 3. A summary of the proposed use patterns is detailed in Table 4.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 6 of 15 Table 3. Summary of Proposed End - Use Product. Trade Name Reg.

No. ai (% o f formulation) Formulation

Type Target Crop Target Pests Label Date Sharpen ® Powered by Kixor Herbicide 7969 -

278 29.74 SC Rice Broadleaf weeds Draft label

submitted 12/17/12 Table 4. Summary of Directions for Use of Saflufenacil. Applic. Timing, Type, and Equip. Formulation App. rate (lb ai/acre) Max. No.

App. per Season Max. Seasonal

App. Rate (lb ai/acre) PHI

(days) Use Directions and Limitations Rice

Ground, Air Sharpen ®

Powered by Kixor Herbicide 0.0 45 - 0. 090 2 0.135 - - A maximum of 0.045 lb ai/A applied post - emergence between the 2 - leaf stage and internode elongation.

- Minimum retreatment interval (RTI) = 14 days.

- May be applied to fields used for crayfish and fish production.

- May not be applied to fields used for mollusc production.

- Flood water from treated fields must be held at least 7 days prior to release. Note: A crop - oil concentrate is required for optimum activity. Table 5. Rotational Crop PBIs for Saflufenacil (from Master Label, no changes proposed). Crop PBI (months) Application rate (lb ai/acre) 0.0225 0.045 0.067 0.089 0.112 0.134 Corn 0 0 0 0 0 0 Corn, sweet 0.5 1 2 3 4 4 Sorghum 0 0 0 0 1 1 Small Grains 0 0 0 0 3 3 Chickpea, Field pea, Edible pea 0 0 3 3 6 6 Lentil 1 2 3 4 6 9 Soybean 1 2 3 4 6 9 Cotton 1.5 3 4 6 6 9 Other Crops 4 5 6 7 8 9 Conclusions: The submitted use directions for Sharpen ® are adequate to allow evaluation of the residue data relative to the proposed uses. 860.1300 Nature of the Residue - Plants DER Reference List 48849001.der.doc The previously - submitted metabolism data for corn, soybean, and tomato were adequate to elucidate the nature of the residue in plants resulting from pre - plant/pre - emergence application. The main reactions involved in the metabolic pathwa y of saflufenacil were N - demethylation atSaflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 7 of 15 the uracil ring, stepwise degradation ( N - dealkylation) of the N

- methyl - N

- isopropyl group, hydrolytic cleavage of the uracil ring generating a urea side chain, and hydroxylation of the phenyl ring. The HED ROCKS de termined that residues of concern for the tolerance expression and risk assessment consist of saflufenacil, M800H11, and M800H35 (Memo, B. Daiss, 1/6/09; D 359645 ). The metabolic pathway of radiolabeled saflufenacil in soybean following a late season post - emergence treatment follows the same initial pathways, but is not as extensive. No new metabolites were observed following post - emergence treatment; however, an additional major metabolite (M800H02), that is not included in the tolerance expression, was o bserved in soybean seed. As the structure of M800H02 is closely related to the parent compound and it is the precursor of the regulated metabolite M800H11, HED concluded that M800H02 is a residue of concern for risk - assessment purposes in seed crops follo wing post - emergence treatment. BASF Corporation has submitted a study investigating the metabolism of uniformly phenyl ring labeled [phenyl - U 14 C]saflufenacil (PH label) and pyrimidine ring - labeled [uracil - 4 - 14 C]saflufenacil (UR label) following early pos t - emerg ence foliar application to rice. The radiolabeled test substances were applied to rice plants (BBCH growth stages 22 - 24) grown in growth chambers as a single broadcast foliar spray at a nominal rate of 0.089 lb ai/A (2X the proposed post - emergence use rate). See Memo, G. Kramer, 4/2/13 ( D405746 ) for the review of this study. Metabolism of saflufenacil in rice (Figure 1, copied without alteration from MRID 48849001) proceeds mainly via N - dealkylation reactions at two sites of the molecule and less extensively by hydrolysis of the uracil ring or by side chain hydroxylation. N - d emethylation on the uracil ring yields metabolite M800H02, while N - demethylation at the sulfonamide side chain yields metabolites M800H01 and M800H03. Metabolites M800H10 and M800H11 are formed by demethylation at both sites, and M800H11 is metabolized to M800H09 by a second N dealkylation step or to M800H35 by hydrolysis of the uracil ring followed by degradation of the side chain or by direct degradation of the uracil ring. M800H35 may also be formed from M800H02 by initial hydrolytic cleavage of the ur acil moiety to form M800H39 and subsequent N - demethylation of this metabolite. Cleavage of the uracil ring generates a carbon chain fragment which leads to formation of M800H29 (trifluoroacetic acid), while another hydrolysis product of the uracil ring is the methyl ester M800H41 which was identified as an artifact of the work - up procedures (most likely resulting from nucleophilic attack of methanol in methanolic storage and work - up procedures). Further degradation products of the uracil ring are M800H07 and M800H39, and hydroxylation of the sulfonamide side chain generates M800H40. Metabolism in grain is extensive, as demonstrated by incorporation of radioactivity into carbohydrates in both the PH - and UR - labeled matrices.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 8 of 15 Figure 1. Proposed Metabolic Pathway for Saflufenacil in Rice.

Conclusions : The previously - submitted metabolism data for corn, soybean, and tomato were adequate to elucidate the nature of the residue in plants resulting from pre - plant/pre - emergence application. Subsequently, the petitioner submitted a rice metabolism study following post emergence foliar application of saflufenacil. The combined residues of saflufenacil, M800H11, and M800H35 (the current residues of concern for the tolerance expression and risk assessment) in ri ce forage were 71 - 89% of the total radioactive residue (TRR). The only other major metabolite was M800H02, which accounted for 4 - 16% of the TRR in forage. In rice grain, the combined residues of saflufenacil and all metabolites was <10% of the TRR (≤0.01 ppm). HED thus concludes that current tolerance expression adequately accounts for the residues of concern following post - emergence foliar application to rice. Additional metabolism data may be required to support foliar application to non - grass crops.Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 9 of 15 860.1300 Nature of the Residue - Livestock/ 860.1480 Meat, Milk, Poultry, and Eggs The nature of the residue in livestock is adequately understood based on acceptable metabolism studies conducted on lactating goats and laying hens. The HED ROCKS determ ined that saflufenacil per se is the only residue of concern for the tolerance expression and risk assessment (Memo, B. Daiss, 1/6/09; D 359645 ). Rice straw is not a regulated commodity. Rice grain is thus the only livestock feedstuff associated with the proposed use. As the existing tolerance for residues in/on rice grain (as a member of cereal grains Crop Group 15) is unaffected by the proposed new use pattern, no changes in the existing tolerances for livestock commodities are needed. 860.1340 Residu e Analytical Methods BASF Method D0603/02 is the current enforcement method for determination of residues of saflufenacil and its metabolites M800H11 and M800H35 in different plant matrices. Residues of saflufenacil and its metabolites M800H11 and M800H3 5 were extracted with methanol:water (70:30; v:v). The methanol extract was evaporated and reconstituted in methanol:water (50:50; v:v) for LC - MS/MS analysis. Two transitions per analyte were monitored for the quantitation and confirmation of saflufenaci l, M800H11 and M800H35. The residues of each analyte were expressed as parent equivalents using a molecular weight conversion factor (1.0 for saflufenacil, 1.06 for M800H11, and 1.42 for M800H35). The LOQ was 0.01 ppm for each analyte. The limit of dete ction (LOD) was reported to be 3X the standard deviation (SD) at the LOQ for each analyte (0.002 - 0.003 ppm). The method was adequate for data collection in the rice field trials based on acceptable concurrent recovery data. Recoveries were within the acc eptable range of 70 - 120%. BASF analytical Method No. L0073/01 is the current enforcement method for determination of saflufenacil in livestock matrices using LC - MS/MS. Livestock tissue samples including bovine liver, kidney, fat, muscle, whole milk, skimmed milk, cream, and hen’s egg were extracted with acetonitrile. The acetonitrile extract was cleaned - up by liquid/liquid partition using dichloromethane and water. The dichloromethane phase was evaporated and reconstituted in methanol:water (50:50; v:v) for LC - MS/MS analysis. Two transition ions were monitored (m/z of 501 to 459 and 501 to 349) for saflufenacil and either of the transitions can be used for quantitation purposes. The LOQ and LOD of the method are 0.01 ppm and 0.000084 ppm, respectiv ely. Samples of crayfish were analyzed with a simplified version of this method which omitted the clean - up step. For method validation, crayfish tissue samples were fortified with saflufenacil at 0.01 and 1.0 ppm. The method was adequate for data collec tion based on acceptable method validation and concurrent recovery data. Apparent residues of saflufenacil were below the LOQ in/on all samples of untreated water and crayfish. BASF Method L0073/01 is thus suitable as an enforcement method for crayfish. 860.1360 Multiresidue Methods (MRM) Saflufenacil and its metabolites M800H11 and M800H35 were screened through the MRM described in the United States Food and Drug Administration (FDA) Pesticide Analytical Manual, Vol. I (PAM I). Saflufenacil and the m etabolites were tested using procedures outlined in Protocols B, C, D, E, and F of the MRM. All Protocols B, C, D, E, and F were found to beSaflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 10 of 15 unsuitable for determination of residues of saflufenacil and its metabolites M800H11 and M800H35. Since the analy tes are not N - methyl - carbamates, naturally fluorescent or substituted urea derivatives, the tests using Protocol A and G were not performed. 860.1380 Storage Stability Rice: Samples were stored frozen (frozen at trial sites; - 10 °C at BASF; ~ - 26 °C at analytical laboratory) from collection to extraction for 243 - 328 days (8.0 - 10.8 months) for rice grain. All samples were analyzed within 1 day of extraction. Adequate storage stability data are available in/on various crop commodities [corn (grain, fora ge, stover); soybean (seed, forage, hay); orange (fruit, pulp, juice, oil); radish (root); grape (raisin); and garbanzo bean (seed)] indicating that residues of saflufenacil, M800H11, and M800H35 are stable in/on all tested commodities during frozen storag e for up to 548 days (MRID No. 47523801). These data are acceptable to support the storage conditions and durations of samples from the submitted field trials. Crayfish: Actual analysis dates of the samples from the submitted magnitude of residue study in freshwater crayfish were not provided. Based on the sample collection dates and the final report date, the estimated storage duration for frozen samples is <125 days. No supporting storage stability data were submitted. Sample analysis dates are required to determine the duration of storage. Ruminant storage stability data are available which show that saflufenacil is stable for up to 35 days in ruminant matrices (47128015.der.doc). These data can be transla ted to crayfish. However, if crayfish samples were stored for more than 3 5 days, then storage stability data may be required for saflufenacil in crayfish. 860.1400 Water, Fish, and Irrigated Crops Justification to Waive the Data Requirement for Metab olism Studies in Fish (Memo G. Kramer, 4/5/12; D396260) . ChemSAC Decision (3/21/12 meeting): Guideline 860.1400 requires fish metabolism data in a predator or bottom - feeder species. In lieu of this study, BASF is requesting that HED accept the results o f bioaccumulation study in bluegill sunfish conducted for EFED. Since the concentration of saflufenacil in the edible tissue of the fish was only 0.35 ppb at the high - dose level (10 ug/L), this request is reasonable. However, since we have not received a proposed label, granting the waiver should be contingent upon 10 ug/L representing the 1X or an exaggerated use rate. The petitioner should note that this waiver applies only to fish metabolism studies; a field accumulation study in molluscs will still b e required to support the registration of the use of saflufenacil in aquatic systems. DER Reference List 49004101.der.doc BASF Corporation has submitted a study investigating the magnitude and potential for bioaccumulation of saflufenacil residues in fre shwater crayfish exposed to floodwater for up to 28 consecutive days following application of saflufenacil to rice. The test substance was formulated as a 342 g ai/L SC and applied to rice grown in an aquatic tank containing silt loam soil. One pre - eme rgence application was made to the soil prior to flooding at 0.089 lb ai/A and one post - emergence application was made to the plant canopy 7 days after flooding (depth of 10 cm) at 0.045 lb ai/A, for a total of 0.13 lb ai/A (1X).Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 11 of 15 Applications were made at a 54 - day re - treatment interval (RTI) using ground equipment. Ammonium sulfate and methylated seed oil was added to the spray solutions. Crayfish were added to the tanks one day after the last application. Samples of water and crayfish were collected 1 hour (0 day) and 1, 3, 7, 14, 21, and 28 days after the introduction of crayfish to the tank. Following application of saflufenacil to rice at 0.13 lb ai /A (1X), residues of saflufenacil in water ranged from 0.0057 - 0.0199 ppm during the 28 - day exposure period; time - weighted mean measured concentrations ranged from 0.0130 - 0.0185 ppm. Maximum residues were observed on Sample Day 7. In crayfish tissue, resi dues of saflufenacil were below the LOQ (<0.01 ppm) in all samples. The calculated crayfish bioconcentration factor (BCF) values ranged from <0.26 - <0.37. Conclusions : The ChemSAC requested a field accumulation study in molluscs. However, as the Sharp en ® label prohibits production of molluscs and permits crustacean production, the submitted magnitude of saflufenacil residue study in freshwater crayfish is appropriate for this proposed use. Additionally, residues of saflufenacil in water following appl ication to rice at 0.13 lb ai/A (1X) exceeded 10 ug/L, the concentration upon which granting the waiver for fish metabolism data was contingent. The proposed tolerance for residues of saflufenacil in fish is required as the Sharpen ® label specifically all ows for application to fields used for commercial fish production. Water and Irrigated Crops: Flood water from treated fields must be held at least 7 days prior to release. Following application of saflufenacil to rice at 0.13 lb ai/A (1X), residues of saflufenacil in water were 0.0199 ppm 7 days after the last application. The most recent HED risk assessment assumed estimated drinking water concentrations of 0.180 ppm (acute) and 0.173 ppm (chronic; see Memo, G. Kramer, et al ., 4/19/11; D 380636 ). As t he estimated drinking water concentrations are significantly higher than residues in water 7 days following application of saflufenacil to rice and there is low potential for bioaccumulation , HED is not concerned with residues in water and irrigated crops. 860.1500 Crop Field Trials DER Reference List 48945803.der.doc BASF Crop Protection has submitted field trial data for saflufenacil on rice reflecting residues of saflufenacil and metabolites on rice grain and straw. Rice straw is no longer consider ed to be a regulated livestock feedstuff; therefore, only the data for grain are presented herein. Sixteen field trials were conducted in the U.S. during the 2011 growing season in the North American Free Trade Agreement (NAFTA) Growing Zones 4 (AR, LA, a nd MO; 11 trials), 5 (MO; 1 trial), 6 (TX; 2 trials), and 10 (CA; 2 trials). Eight trials were conducted by one Principal Field Investigator (PFI) in Zones 4 and 6, and four trials were conducted by another PFI, also in Zones 4 and 6. Because residues in grain were below the LOQ in/on samples from all trials, except one trial which experienced unusual growing conditions (see below), HED has concluded that trial independence is not an issue for this study. Each trial consisted of one untreated plot and on e treated plot. At each trial location, the treated plot received two broadcast applications of a 342 g ai/L SC formulation of saflufenacil (BAS 800 04 H ). The first application was made at the time of rice seeding ( preplant/pre - flood for water -Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 12 of 15 seeded ri ce [CA trials] and preemergence in dry - seeded rice) at 0.087 - 0.095 lb ai/A (98 - 106 g ai/ha) followed by a second application made after flooding to rice at the internode elongation growth stage at 0.043 - 0.046 lb ai/A (48 - 52 g ai/ha), for a total seasonal r ate of 0.131 - 0.139 lb ai/A (1X) . Applications were made at 39 - to 71 - day RTIs using ground equipment in spray volumes of 17 - 21 gal/A (159 - 195 L/ha). A methylated seed oil (MSO) and ammonia sulfate (AMS) were added to the spray mixture for each of the app lications. Samples of rice grain and straw were harvested at 54 - to 103 - day preharvest intervals (PHIs). At the Yuba City, CA trial site (RCN R110020), winds lodged the rice treated plot following draining of the rice paddy, and rain refilled the rice pa ddy so the rice was on the ground and under water for approximately 10 days prior to harvest. At harvest, the rice was cut and allowed to dry on the bank for a few hours, then threshed. This is not typical agronomic or commercial practice. Residues from this trial were significantly higher than the other 15 trials and were not included. Following two broadcast applications of the 342 g ai/L SC formulation of saflufenacil at 0.131 - 0.139 lb ai/A, combined residues (and per - trial averages) of saflufenaci l, M800H11, and M800H35 in/on rice grain harvested at a 54 - to 103 - day PHI were all <LOQ (<0.03 ppm). Residue decline data were not submitted; however, none are required because the pesticide is applied before the edible portion of the crop has formed. C onclusions : The submitted field trial data are adequate to fulfill data requirements. The number and locations of the trials are in accordance with OCSPP Guideline 860.1500 (Table 6). The available data will thus support the proposed use pattern. Table 6. Trial Numbers and Geographical Locations . NAFTA Growing Zones Rice Submitted Requested 1 Canada U.S. 4 11 -- 11/7 5 1 -- 1/1 6 2 -- 2/2 10 2 -- 2/2 Total 16 16/12 1 As per Table 5 of OCSPP 860.1500 for rice. The second number reflects a 25% reduction in the number of trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application results in no quantifiable res idues. 860.1520 Processed Food and Feed DER Reference List 48945804.der.doc BASF Crop Protection has submitted a processing study for saflufenacil on rice. In two crop field trials conducted in CA and MO in 2011, one untreated and three treated plots were established at exaggerated rates [Treatment Plots 2, 3, and 4 corresponding to 1X, 3X, or 5X the seasonal field application rate for saflufenacil] . Since rice from Treatment Plot 4 (5X) survived, samples from the Treatment Plots 2 and 3 were not fur ther examined. At both trial locations, Treatment Plot 4 received two broadcast applications of a 342 g ai/L SC formulation of saflufenacil (BAS 800 04 H ). The first application was made at the time of rice seeding ( preplant/pre - flood for water - seeded ri ce [CA trial] and preemergence in dry - seeded rice [MO trial]) at 0.450 - 0.457 lb ai/A (504 - 512 g ai/ha) followed by a second application made afterSaflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 13 of 15 flooding to rice at the internode elongation growth stage at 0.220 - 0.223 lb ai/A (247 - 250 g ai/ha), for a tot al seasonal rate of 0.670 - 0.679 lb ai/A ( 5X ). Applications were made at 49 - to 60 - day RTIs using ground equipment in spray volumes of 17.2 - 20.0 gal/A (161 - 187 L/ha) and included a MSO and AMS at both trial sites. Samples of rice grain were harvested at m aturity [PHIs of 84 - 103 days]. Rice grain samples were stored at GLP Technologies (Navasota, TX) and held until analysis of the RAC samples. Following two broadcast applications of the 342 g ai/L SC formulation of saflufenacil at a rate of 0.670 - 679 lb ai/A (751 - 761 g ai/ha), combined residues (and per - trial averages) of saflufenacil, M800H11, and M800H35 in/on rice grain harvested at a 84 - to 103 - day PHI were all <LOQ (<0.03 ppm). As the RAC grain samples were found to contain no residues greater than the LOQ, processing was not performed on the bulk samples. Processing factors were thus not calculated in this study. T he maximum theoretical concentration factors for rice are 5.0X for hulls and 7.7X for bran (based separation of components; OCSPP 860.1520, Table 3). Conclusions: The submitted rice processing data are adequate to fulfill data requirements. As the residues in the RAC were <LOQ after treatment at a 5X rate, a separa te tolerance for hulls and bran will not be required. 860.1650 Submittal of Analytical Reference Standards Analytical standards of saflufenacil (expiration date: 5/1/14), M800H11 (metabolite 5303307; expiration date: 7/1/14), and M800H35 (metabolite 5303308; expiration date: 7/1/14) are currently available in the National Pesticide Standards Repository [source: personal communication with T. Cole of ACL/BEAD, 4/2/13]. 860.1850/860.1900 Confined/Field Accumulation in Rotation al Crops The previously submitted confined and field rotational crop data are adequate to satisfy data requirements for application rates up to 0.137 lb ai/A (1X). The available data indicate that residues of saflufenacil and its metabolites M800H11 and M800H35 were each <LOQ in/on all rotational crop matrices at a 120 - day PBI. These data support the labeled rotational crop restriction of 4 months for all non - labeled crops. Unless the petitioner requests PBIs shorter than 120 days, no additional data ar e required, and tolerances for inadvertent residues in/on rotational crops need not be established in conjunction with the currently proposed uses. 860.1550 Proposed Tolerances BASF has petitioned for the establishment of permanent tolerances 40 CFR §18 0.649(a)(1) for saflufenacil, including its metabolites and degradates, in or on the agricultural commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of saflufenacil, 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2 H ) - pyrimidinyl] - 4 - fluoro - N - [[methyl(1 - methylethyl)amino]sulfonyl]benzamide, and its metabolites N

- [2 - chloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro - 1(2 H ) - pyrimidinyl) - 4 - fluorobenzoyl] - N ' - isopropylsulfamide and N - [4 - chloro - 2 - fluoro - 5 -Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 14 of 15 ({[(isopropylamino)sulfonyl]amino}carbonyl)phenyl]urea, calculated as the stoichiometric equivalent of saflufenacil in/on the following plant commodities:

Grain, cereal, forage, fodder and straw group 16 (ex cept rice straw) 0.1 ppm Rice, straw 0.30 ppm However, these tolerances are not required as rice straw is not a regulated commodity. Since the existing tolerance of 0.03 ppm for residues in/on rice grain (as a member of cereal grains Crop Group 15) is supported by the residue data reflecting the post - emergent use pattern, no changes in the existing tolerances for Crop Group 15 are needed. BASF has also petitioned for the establishment of permanent tolerances 40 CFR §180.649(a)(2) for saflufenacil, incl uding its metabolites and degradates, in or on the agricultural commodities listed below. Compliance with the tolerance levels specified below is to be determined by measuring only saflufenacil, 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethy l) - 1(2 H ) - pyrimidinyl] - 4 - fluoro - N - [[methyl(1 - methylethyl)amino]sulfonyl]benzamide, in/on the following commodit ies :

Fish - freshwater finfish 0.01 ppm Fish - shellfish, crustacean Provided issues related to storage stability are resolved, the submitted magnitude of saflufenacil residue study in freshwater crayfish will support the proposed tolerance for residues in/on fish shellfish, crustacean. In addition, the crayfish magnitude of saflufenacil residue data can be translated to support the proposed tolerance for residues in/on fish - freshwater finfish. A summary of the recommended tolerances for the current petition are listed in Table 7. The petitioner should submit a revised Se ction F reflecting the corrected commodity definitions. There are no Canadian or Codex maximum residue limits (MRLs) established for residues of saflufenacil and its metabolites in crayfish or fish. Harmonization is thus not an issue for this petition. Table 7. Tolerance Summary for Saflufenacil. Commodity Proposed Tolerance (ppm) HED - Recommended

Tolerance (ppm) Correct Commodity

Definition/Comments Grain, cereal, forage, fodder and straw group 16 (except rice straw) 0.1 - Not required as rice straw is not a regulated commodity. Rice, straw 0.30 - Fish - freshwater finfish 0.01 0.01 Fish - shellfish, crustacean 0.01 0.01 Attachments: International Residue Limit Status (IRLS) sheet . cc: G. Kramer (RAB1) RDI: RAB1 Chemists (7/10/13) G.F. Kramer:S10957:PY - S:(703)305 - 5079:7509P:RAB1Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 407976

Page 15 of 15 

### IRLS Sheet. Saflufenacil (118203; Date of Request: 07/01/2013) Summary of U.S. and International Tolerances and Maximum Residue Limits Residue Definition : U.S. Canada Mexico 2 Codex 3 40 CFR 180.649: Plant: saflufenacil, including its metabolites and degradates, sum of saflufenacil, 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2 H

) - pyrimidinyl] - 4 - fluoro - N

- [[methyl(1 - methylethyl)amino]sulfonyl]benza mide, and its metabolites N - [2 - chloro - 5 - (2,6 - dioxo - 4 - (trifluoromethyl) - 3,6 - dihydro 1(2 H ) - pyrimidinyl) - 4 - fluorobenzoyl] - N ' - isopropylsulfamide and N - [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl]amino }carbonyl)p henyl]urea, calculated as the stoichiometric equivalent of saflufenacil Livestock: saflufenacil 2 - chloro - 5 - [3,6 - dihydro - 3 - methyl 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2 H ) - pyrimidinyl] - 4 - fluoro - N - [[methyl(1 - methylethyl)amino]sulfonyl]benzam ide, including the met abolites N' - {2 - chloro - 4 - fluoro - 5 - [1,2,3,6 - tetrahydro - 2,6 - dioxo - 4 - (trifluoromethyl)pyrimidin - 1 - yl]benzoyl} - N

- isopropyl sulfamide and N - [4 - chloro - 2 - fluoro - 5 - ({[(isopropylamino)sulfonyl] amino}carbonyl)phenyl]urea Livestock: 2 - chloro - 5 - [3,6 - dihydro 3 - methyl - 2,6 - dioxo - 4 - (trifluoromethyl) - 1(2 H

) - pyrimidinyl] - 4 - fluoro - N

- [[methyl(1 - methylethyl)amino]sulfonyl]benzam ide Saflufenacil The residue is not fat soluble

Commodity 1 Tolerance (ppm)/Maximum Residue Limit (mg/kg) U.S. Canada Mexico 2 Codex 3 Fish - freshwater finfish 0.01 Fish - shellfish, crustacean 0.01 Completed: M. Negussie; 07/03/2013 1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and not those proposed by the applicant. 2 Mexico adopts U.S. tolerances and/or Codex MRLs for its export purposes. 3 * = absent at the limit of quantitation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed postharvest treated commodity, such as processing of treated stored wheat. (fat) = to be measured on the fat portion of the sample. MRLs indicated as proposed have not been finalized by the CCPR and the CAC.