
--------------------------------------------------------------------------------

      UNITED STATES ENVIRONMENTAL PROTECTION AGENCY
                            WASHINGTON, D.C.  20460

                                                                      OFFICE OF
                                                            CHEMICAL SAFETY AND
	                                                                                                  POLLUTION PREVENTION
MEMORANDUM

Date:		04-AUG-2011

Subject:	Saflufenacil in/on Imported Coffee, Banana, and Mango.  Summary of Analytical Chemistry and Residue Data.

PC Code:  118203
DP Barcode:  D390922
Decision No.:  442242
Registration No:  NA
Petition No.:  0E7806
Regulatory Action:  Tolerances With No U.S. Registration
Risk Assessment Type:  NA
Case No.:  NA
TXR No.:  NA
CAS No.:  372137-35-4
MRID Nos.:  482398-01 thru -07
40 CFR:  §180.649

From:		George F. Kramer, Ph.D., Senior Chemist
		Risk Assessment Branch 1 (RAB1)
		Health Effects Division (HED) (7509P)

Through:		Dana M. Vogel, Branch Chief
		RAB1/HED (7509P)

To:	       Kathryn Montague/Susan Stanton, 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[(TM)] 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), the forage, fodder, and straw of cereal grains (Crop Group 16), cotton, and sunflower.  

BASF has submitted a proposal to establish tolerances for saflufenacil in/on imported coffee, banana, and mango (PP#0E7806).  The tolerance petition on these crops is the result of the use of Heat[(R)], a 70% water-dispersible granule (WDG) formulation, in Central and South America.  

Heat[(R)] is proposed for up to three foliar spray applications directed to the base of the plants with a total maximum application rate of 0.131 lb ai/A, and use of an adjuvant is required.  Preharvest intervals (PHIs) of 7-30 days are proposed.

BASF has petitioned for the establishment of permanent tolerances for "saflufenacil, including its metabolites and degradates, in or on the imported 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(2H)-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(2H)-pyrimidinyl)-4-fluorobenzoyl]-N'-isopropylsulfamide and N-[4-chloro-2-fluoro-5-({[(isopropylamino)sulfonyl]amino}carbonyl)phenyl]urea, calculated as the stoichiometric equivalent of saflufenacil" in/on the following raw agricultural commodities (RACs):

Coffee, green bean
0.03 ppm
Banana, whole fruit
0.03 ppm
Mango, fruit
0.03 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) determined that residues of concern for the tolerance expression and risk assessment consist of saflufenacil, M800H11, and M800H35 (Memo, B. Daiss, 1/6/09; D359645).  This conclusion was translated to perennial crops (i.e., tree fruits and tree nuts) where saflufenacil application is directed to the weeds on the orchard floor (Memo, G. Kramer, 7/22/09; D349938).  As the proposed use on coffee, banana, and mango is also directed to weeds at the base of the plants, HED concludes that the residues of concern for the tolerance expression and risk assessment also consist of saflufenacil, M800H11, and M800H35 for these crops.

The nature of the residue in livestock is adequately understood based on acceptable metabolism studies conducted on lactating goats and laying hens.  There are no livestock feedstuffs associated with the proposed uses; therefore, no changes in the existing tolerances for livestock commodities are needed.

The petitioner has submitted two liquid chromatography/mass spectroscopy/mass spectroscopy (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 M800H35 in 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 the various studies associated with the current petition.  HED has determined that Method D0603/02 is a suitable enforcement method for plant commodities as defined in Standard Operating Procedure (SOP) No. ACB-019 (9/15/08).  

The submitted magnitude of the residue data for coffee, banana, and mango are adequate.  There are also adequate storage stability data to validate the storage conditions and intervals of samples collected from the field trials.  Quantifiable residues were not found in coffee RAC samples (green beans) even after application of saflufenacil at exaggerated rates (~3X); therefore, analysis of coffee processed fractions (roasted beans, instant coffee) was not necessary and separate tolerances for processed fractions are not required.

Regulatory Recommendations and Residue Chemistry Deficiencies

Pending submission of a revised Section F (see requirements under Proposed Tolerances), there are no residue chemistry issues that would preclude granting permanent tolerances for residues of saflufenacil on the requested crops.  The submitted data support:  "Tolerances are established for residues of the herbicide saflufenacil, including its metabolites and degradates, in or on the commodities in the table below.  Compliance with the tolerance levels specified below is to be determined by measuring only the sum of saflufenacil (2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-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(2H)-pyrimidinyl)-4-fluorobenzoyl]-N'-isopropylsulfamide and N-[4-chloro-2-fluoro-5-({[(isopropylamino)sulfonyl]amino}carbonyl)phenyl]urea, calculated as the stoichiometric equivalent of saflufenacil, in or on the following commodities."

Coffee, green bean
                                   0.03 ppm
Banana
                                   0.03 ppm
Mango
                                   0.03 ppm

Note to RD:  These tolerances should include a footnote stating "No U.S. registrations as of [date of FR notice]."

860.1550 Proposed Tolerances

   * The petitioner is requested to submit a revised Section F specifying the revised definitions summarized above.

A human-health risk assessment is forthcoming in a separate document (DP# 384602).


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 subsequent 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 metabolites 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(2H)-pyrimidinyl)benzoyl]-N-isopropyl-N-methylsulfamide
CAS name
2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide
CAS registry number
372137-35-4
End-use product (EP)
Sharpen[(TM)] 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(2H)-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 (pKa)
4.41
Octanol/water partition coefficient
Mean Log Pow = 2.6 (Pow = 368.3)
UV/visible absorption spectrum
wavelength maximum:  λmax = 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 a draft Brazilian label for the 70% WDG formulation (Heat[(R)]), which is representative of the Central and South American labels.  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.  
Table 3.  Summary of Proposed End-Use Product.
Trade Name
                                   Reg. No.
                             ai (% of formulation)
                               Formulation Type
                                 Target Crops
                                 Target Pests
                                  Label Date
Heat[(R)]
                                      NA
                                      70
                                      WDG
                           coffee, banana, and mango
                                Broadleaf weeds
                          Draft label submitted 11/10

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
                           Coffee, Banana, and Mango
                           Ground directed to weeds
                                   Heat[(R)]
                                  0.022-0.044
                                       3
                                     0.131
                                  7 (coffee)
                            15 (mango) 30 (banana) 
Applications are to be made in 16-43 gal/acre
Note:  A non-ionic adjuvant system is required for optimum activity.

Conclusions:  The submitted use directions for Heat[(R)] are adequate to allow evaluation of the residue data relative to the proposed uses.  


860.1300 Nature of the Residue - Plants

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 pathway of saflufenacil were N-demethylation at 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 determined that residues of concern for the tolerance expression and risk assessment consist of saflufenacil, M800H11, and M800H35 (Memo, B. Daiss, 1/6/09; D359645).  This conclusion was translated to perennial crops (i.e., tree fruits and tree nuts) where saflufenacil application is directed to the weeds on the orchard floor (Memo, G. Kramer, 7/22/09; D349938).  As the proposed use on coffee, banana, and mango is also directed to weeds at the base of the plants, HED concludes that the residues of concern for the tolerance expression and risk assessment also consist of saflufenacil, M800H11, and M800H35 for these crops.


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.  There are no livestock feedstuffs associated with the proposed uses; therefore, no changes in the existing tolerances for livestock commodities are needed.


860.1340 Residue 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 M800H35 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 saflufenacil, 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 detection (LOD) was reported to be 3X the standard deviation (SD) at the LOQ for each analyte (0.002-0.003 ppm).

Recovery samples, prepared at levels of LOQ and 10X LOQ in each matrix, were generally within the acceptable range of 70-120%.  


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 metabolites 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 be unsuitable for determination of residues of saflufenacil and its metabolites M800H11 and M800H35.  Since the analytes 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

Storage stability data have been submitted for residues of saflufenacil and its metabolites M800H11 and M800H35 in/on various crop commodities [corn (grain, forage, 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 storage for up to 548 days (MRID No. 47523801).  There are no unresolved storage stability issues, and no corrections need to be applied to the various magnitude of the residue studies.  


860.1500 Crop Field Trials

Banana

DER Reference List	48239801.der.doc
			48239802.der.doc
			48239803.der.doc

MRID No. 48239801:  BASF Corporation has submitted field trial data for saflufenacil on banana.  Two banana field trials were conducted during the 2008 growing season in Brazil.  Each trial location consisted of one untreated and one treated plot.  Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A (1X) directed to the base of the plants, with a 30-day retreatment interval (RTI), for a total application rate of 0.131 lb ai/A (1X).  The applications were made using ground equipment with 21 gallons per acre (GPA) spray volumes.  An adjuvant (surfactant, Dash[(R)]) was included in the spray mixture.  Samples of mature bananas were harvested at a 30-day PHI.  

The results from these trials on banana show that after three applications of saflufenacil at 0.044 lb ai/A (0.049kg ai/ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in banana samples harvested at a 30-day PHI.  Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm.

MRID No. 48239802:  BASF Corporation has submitted field trial data for saflufenacil on banana.  Two banana field trials were conducted during the 2010 growing season in Brazil.  Each trial location consisted of one untreated and one treated plot.  Each treated plot received five applications of the 70% WDG formulation of saflufenacil at 0.0667 lb ai/A (1.5X) directed to the base of the plants, with a 3-week RTI, for a total application rate of 0.333 lb ai/A (2.5X).  The applications were made using ground equipment with 21 GPA spray volumes.  An adjuvant (surfactant, Dash[(R)]) was included in the spray mixture.  Samples of mature bananas were harvested at 0- and 1-day PHIs.  

The results from these trials on banana show that after five applications of saflufenacil at 0.0667 lb ai/A (0.0749 kg ai/ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in banana samples harvested at 0- and 1-day PHIs.  Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm.

MRID No. 48239803:  BASF Corporation has submitted field trial data for saflufenacil on banana.  A total of 10 field trials were conducted on bananas during the 2008 growing season in Costa Rica (2 trials), Colombia (1 trial), Ecuador (3 trials), Guatemala, (1 trial), Honduras (2 trials), and Panama (1 trial).

Each trial location consisted of one untreated and one treated plot.  Each treated plot received five applications of the 70% WDG formulation of saflufenacil directed to the base of the plants at 0.064-0.071 lb ai/A (1.5X-1.6X), with 11- to 28-day retreatment intervals (RTIs), for a total application rate of 0.33-0.35 lb ai/A/season (2.8X-3.0X).  The applications were made using ground equipment with approximately 20-23 GPA spray volumes.  An adjuvant [crop-oil concentrate (COC)] was included in the spray mixture, together with ammonium sulfate (AMS) fertilizer.  Duplicate samples of commercially mature banana were harvested at a 0- or 1-day PHI.

The results from these trials on banana show that after five applications of saflufenacil directed to the base of the plants at 0.067 lb ai/A/application (0.075 kg ai/ha/application), for a total seasonal rate of 0.33 lb ai/A (0.375 kg ai/ha), maximum saflufenacil, M800H11, and M800H35 residues were <LOQ (<0.01 ppm each) in/on banana whole fruit samples harvested at a 0-day PHI (n=20) or 1-day PHI (n=20).  Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm at the 0- and 1-day PHIs.

TABLE 5.  Summary of Residue Data from Crop Field Trials with Banana (MRID#s 48239801 thru -03).
Commodity
                         Total Applic. Rate (lb ai/A)
                                  [kg ai/ha]
                                  PHI (days)
                                    Analyte
                            Residue Levels (ppm)[1]




                                       n
                                     Min.
                                     Max.
                                    HAFT[2]
                                    Median
                                     Mean
                                   Std. Dev.
      Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate, 30-Day PHI
Banana
                                   0.33-0.35
                                 [0.372-0.392]
                                       0
                                 Saflufenacil
                                      22
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H11
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H35
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                  Combined[3]
                                       
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                       -
Banana
                                   0.33-0.35
                                 [0.372-0.392]
                                       1
                                 Saflufenacil
                                      22
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H11
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H35
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                  Combined[3]
                                       
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                       -
Banana
                                     0.131
                                    [0.147]
                                      30
                                 Saflufenacil
                                       2
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H11
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H35
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                  Combined[3]
                                       
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                       -
[1]  For calculation of the HAFT, median, mean, and standard deviation, residue values of <0.01 ppm (<LOQ) were considered to be 0.01 ppm (LOQ).
[2]  HAFT = highest-average field trial.
[3]  Combined residues of saflufenacil (parent + M800H11 + M800H35).

Conclusions:  The submitted residue data are adequate to fulfill data requirements for bananas imported from Central/South America.  Even though all major exporting countries were not represented (Table 6), HED will not require additional data as all residues were <LOQ, even at ~3X exaggerated use rate.  Also, HED generally requires residue data for both bagged and unbagged bananas.  The fruit in these trials were "grown and maintained according to typical agricultural practices for each region," which HED interprets to mean bagged.  As saflufenacil is not applied directly to the plants and there is no evidence of systemic activity in fruit/tree crops, additional data on un-bagged bananas will not be required.  The available data will thus support the proposed use pattern.

TABLE 6.  Trial Numbers and Geographical Locations.
Country
                                    Banana
                                       
                                   Submitted
                                 Requested[1]
                                       
                                       
                                     U.S.
Brazil
                                       4
                                       
Columbia
                                       1
                                       2
Costa Rica
                                       2
                                       3
Ecuador
                                       3
                                       3
Guatemala
                                       1
                                       0
Honduras
                                       2
                                       2
Mexico
                                       0
                                       2
Panama
                                       1
                                       0
Total
                                      14
                                      12
[1]  The requested number and geographic distribution of field trials for bananas, according to the NAFTA Guidance Document on Data Requirements for Tolerances on Imported Commodities in the United States and Canada, 12/05.

The residue data for bananas were not entered into the OECD MRL Calculator as all of the residues were <LOQ.  The recommended tolerance for the combined residues of saflufenacil and its metabolites M800H11 and M800H35, expressed as parent equivalents, is 0.03 ppm for banana. 

Coffee

DER Reference List	48239804.der.doc
			48239805.der.doc

MRID No. 48239804:  BASF Corporation has submitted field trial data for saflufenacil on coffee.  Three coffee field trials were conducted during the 2008 growing season in Brazil.  Each trial location consisted of one untreated and one treated plot.  Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A (1X) directed to the base of the plants, with a 4-week RTI, for a total application rate of 0.131 lb ai/A (1X).  The applications were made using ground equipment with 21 GPA spray volumes.  An adjuvant (surfactant, Dash[(R)]) was included in the spray mixture.  Samples of mature coffee beans were harvested at a 7-day PHI.  

The results from these trials on coffee show that after three applications of saflufenacil at 0.044 lb ai/A (0.049 kg ai/ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in coffee samples harvested at a 7-day PHI.  Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm.

MRID No. 48239805:  BASF Corporation has submitted field trial data for saflufenacil on coffee.  Five coffee field trials were conducted during the 2008 growing season in Costa Rica (2 trials), Colombia (2 trials), and Mexico (1 trial).  Each trial location consisted of one untreated and one treated plot.  Each treated plot received four applications of the 70% WDG formulation of saflufenacil at 0.087-0.092 lb ai/A (2.0-2.1X) directed to the base of the plants, with 8- to 35-day RTIs, for a total application rate of 0.35-0.36 lb ai/A (2.7X).  The applications were made using ground equipment with 21-22 GPA spray volumes.  An adjuvant (COC) was included in the spray mixture.  Samples of mature coffee beans were harvested at 0-day or 1-day PHIs.  

The results from these trials on coffee show that after four applications of saflufenacil (70% WDG) directed to the base of the plants targeting 0.087 lb ai/A/application (0.098 kg ai/ha/application), for a total seasonal rate of 0.35 lb ai/A (0.392 kg ai/ha), maximum saflufenacil, M800H11, and M800H35 residues were <LOQ (<0.01 ppm each) in/on coffee green bean samples harvested at a 0-day PHI (n=10) or 1-day PHI (n=10).  Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm at the 0- or 1-day PHI.

TABLE 7.  Summary of Residue Data from Crop Field Trials with Coffee (MRID#s 48239804 and -05).
Commodity
                             Total Rate (lb ai/A)
                                   [g ai/ha]
                                  PHI (days)
                                    Analyte
                            Residue Levels (ppm)[1]




                                       n
                                     Min.
                                     Max.
                                    HAFT[2]
                                    Median
                                     Mean
                                   Std. Dev.
      Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate, 7-Day PHI
Coffee, green bean
                                   0.35-0.36
                                   [392-400]
                                       0
                                 Saflufenacil
                                      10
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H11
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H35
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                  Combined[3]
                                       
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                       -

                                   0.35-0.36
                                   [392-400]
                                       1
                                 Saflufenacil
                                      10
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H11
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H35
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                  Combined[3]
                                       
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                       -
Coffee, green bean
                                     0.131
                                    [0.147]
                                       7
                                 Saflufenacil
                                       3
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H11
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H35
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                  Combined[3]
                                       
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                       -
[1]  For calculation of the HAFT, median, mean, and standard deviation, residue values of <0.01 ppm (<LOQ) were considered to be 0.01 ppm (LOQ).
[2]  HAFT = highest-average field trial.
[3]  Combined residues of saflufenacil (parent + M800H11 + M800H35).

Conclusions:  The submitted residue data are adequate to fulfill data requirements for coffee imported from Central/South America.  Even though all major exporting countries were not represented (Table 8), HED will not require additional data as all residues were <LOQ, even at ~3X exaggerated use rate.  The available data will thus support the proposed use pattern.

TABLE 8.  Trial Numbers and Geographical Locations.
Country
                                    Coffee
                                       
                                   Submitted
                                 Requested[1]
                                       
                                       
                                     U.S.
Brazil
                                       3
                                       1
Columbia
                                       2
                                       1
Costa Rica
                                       2
                                       1
Guatemala
                                       0
                                       1
Indonesia
                                       0
                                       1
Mexico
                                       1
                                       1
Vietnam
                                       0
                                       1
Total
                                       8
                                       7
[1]  The requested number and geographic distribution of field trials for coffee, according to the NAFTA Guidance Document on Data Requirements for Tolerances on Imported Commodities in the United States and Canada, 12/05 and import data (http://www.ers.usda.gov/Data/FoodImports/Data/2011/CoffeeT1.xls and http://www.nationmaster.com/graph/eco_tra_wit_us_us_imp_of_gre_cof-trade-us-imports-green-coffee).  All countries (in which the pesticide is marketed or intended to be marketed) must be represented if the amount that they export to North America represents 5% or more of imports of the subject crop into any of the country in which a tolerance is being sought. 

The residue data for coffee were not entered into the OECD MRL Calculator as all of the residues were <LOQ.  The recommended tolerance for the combined residues of saflufenacil and its metabolites M800H11 and M800H35, expressed as parent equivalents, is 0.03 ppm for coffee, green bean. 

Mango

DER Reference List	48239806.der.doc
			48239807.der.doc

MRID No. 48239806:  BASF Corporation has submitted field trial data for saflufenacil on mango.  Two mango field trials were conducted during the 2008 growing season in Brazil.  Each trial location consisted of one untreated and one treated plot.  Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A (1X) directed to the base of the trees, with a 10-day RTI, for a total application rate of 0.131 lb ai/A (1X).  The applications were made using ground equipment with 21 GPA spray volumes.  An adjuvant (surfactant, Dash[(R)]) was included in the spray mixture.  Samples of mature mango were harvested at a 14- or 15-day PHI.  

The results from these trials on mango show that after three applications of saflufenacil at 0.044 lb ai/A (0.049kg ai/ ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in mango samples harvested at a 14- or 15-day PHI.  Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm.

MRID No. 48239807:  BASF Corporation has submitted field trial data for saflufenacil on mango.  Two mango field trials were conducted during the 2008-2009 growing season in Brazil.  Each trial location consisted of one untreated and one treated plot.  Each treated plot received three applications of the 70% WDG formulation of saflufenacil at 0.044 lb ai/A (1X) directed to the base of the trees, with a 10-day RTI, for a total application rate of 0.131 lb ai/A (1X).  The applications were made using ground equipment with 21 GPA spray volumes.  An adjuvant (surfactant, Dash[(R)]) was included in the spray mixture.  Samples of mature mango were harvested at a 15-day PHI.  

The results from these trials on mango show that after three applications of saflufenacil at 0.044 lb ai/A/application (0.049kg ai/ha), residues of saflufenacil, M800H11, and M800H35 were below the LOQ (<0.01 ppm each) in mango samples harvested at a 15-day PHI.  Therefore, the maximum combined residues of saflufenacil and its metabolites was <0.03 ppm.

TABLE 9.  Summary of Residue Data from Crop Field Trials with Mango.
Commodity
                         Total Applic. Rate (lb ai/A)
                                  [kg ai/ha]
                                  PHI (days)
                                    Analyte
                            Residue Levels (ppm)[1]




                                       n
                                     Min.
                                     Max.
                                    HAFT[2]
                                    Median
                                     Mean
                                   Std. Dev.
      Proposed Use = 0.131 lb ai/acre Max. Seasonal App. Rate, 15-Day PHI
Mango
                                     0.131
                                    [0.147]
                                     14-15
                                 Saflufenacil
                                       4
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H11
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                    M800H35
                                       
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                   <0.01
                                       -

                                       
                                       
                                  Combined[3]
                                       
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                   <0.03
                                       -
[1]  For calculation of the HAFT, median, mean, and standard deviation, residue values of <0.01 ppm (<LOQ) were considered to be 0.01 ppm (LOQ).
[2]  HAFT = highest-average field trial.
[3]  Combined residues of saflufenacil (parent + M800H11 + M800H35).

Conclusions:  The submitted residue data are adequate to fulfill data requirements for mango imported from Central/South America.  Even though all major exporting countries were not represented (Table 10), HED will not require additional data as all residues were <LOQ.  The available data will thus support the proposed use pattern.

TABLE 10.  Trial Numbers and Geographical Locations.
Country
                                     Mango
                                       
                                   Submitted
                                 Requested[1]
                                       
                                       
                                     U.S.
Brazil
                                       4
                                       1
Ecuador
                                       0
                                       1
Mexico
                                       0
                                       1
Peru
                                       0
                                       1
Total
                                       4
                                       4
[1]  The requested number and geographic distribution of field trials for mango, according to the NAFTA Guidance Document on Data Requirements for Tolerances on Imported Commodities in the United States and Canada, 12/05 and import data (Fruit and Tree Nuts Situation and Outlook Yearbook (USDA, 2008)).  All countries (in which the pesticide is marketed or intended to be marketed) must be represented if the amount that they export to North America represents 5% or more of imports of the subject crop into any of the country in which a tolerance is being sought. 

The residue data for mango were not entered into the OECD MRL Calculator as all of the residues were <LOQ.  The recommended tolerance for the combined residues of saflufenacil and its metabolites M800H11 and M800H35, expressed as parent equivalents, is 0.03 ppm for mango. 


860.1520 Processed Food and Feed

Coffee

BASF requested a waiver for residue data for saflufenacil in/on coffee processed fractions.  HED has previously reviewed processing studies for saflufenacil when applied postemergence-directed under the leaf canopy at the base of fruit tree crops:  apple (MRID 47128229), orange (MRID 47128228), plum (MRID 47128230), and grape (MRID 47128232).  In all of these studies, the individual residues of saflufenacil and its metabolites M800H11 and M800H35 were <LOQ (i.e., 0.01 ppm for each analyte) in/on unwashed RAC samples of apple, orange, plum and grape after application of saflufenacil at exaggerated rates of 2-5X.  Since quantifiable residues were not found in the whole fruit RAC samples, analysis of the processed commodities were not necessary (except for orange- residues in citrus oil were also <LOQ).  A similar conclusion can be reasonably expected for coffee when saflufenacil is applied postemergence-directed beneath the leaf canopy of coffee plants.  Quantifiable residues were not found in coffee RAC samples (green beans) even after application of saflufenacil at exaggerated rates (~3X); therefore, analysis of coffee processed fractions (roasted beans, instant coffee) is not necessary and separate tolerances for processed fractions are not required.


860.1650 Submittal of Analytical Reference Standards

Analytical standards of saflufenacil (expiration date:  2/1/13), M800H11 (expiration date:  7/1/14), and M800H35 (expiration date:  7/1/14) are currently available in the National Pesticide Standards Repository [source:  personal communication with T. Cole of ACL/BEAD, 6/20/11].  


860.1850/860.1900 Confined/Field Accumulation in Rotational Crops

Rotational crop studies are not germane to this petition as coffee, banana, and mango are not rotated with other crops.


860.1550 Proposed Tolerances

A summary of the recommended tolerances for the current petition are listed in Table 11.  The petitioner should submit a revised section 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 coffee, banana, and mango commodities.  Harmonization is thus not an issue for this petition.

Table 11.  Tolerance Summary for Saflufenacil.

Commodity
                           Proposed Tolerance (ppm)
                        HED-Recommended Tolerance (ppm)
Correct Commodity Definition/Comments
Coffee, green bean
                                     0.03
                                     0.03

Banana, whole fruit
                                     0.03
                                     0.03
Banana
Mango, fruit
                                     0.03
                                     0.03
Mango

Note to RD:  These tolerances should include a footnote stating "No U.S. registrations as of [date of FR notice]."





Attachments:
International Residue Limit Status (IRLS) sheet.




















cc:  G. Kramer (RAB1)
RDI:  RAB1 Chemists (7/13/11)
G.F. Kramer:S10957:PY-S:(703)305-5079:7509P:RAB1IRLS Sheet.

              Saflufenacil (118203; Date of Request: 06/20/2011)
Summary of U.S. and International Tolerances and Maximum Residue Limits 
Residue Definition:
U.S.
Canada
Mexico[2]
Codex
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(2H)-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(2H)-pyrimidinyl)-4-fluorobenzoyl]-N'-isopropylsulfamide and N-[4-chloro-2-fluoro-5-({[(isopropylamino)sulfonyl]amino}carbonyl)phenyl]urea, calculated as the stoichiometric equivalent of saflufenacil
Livestock:  saflufenacil
2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide, including the metabolites 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(2H)-pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide

None
Commodity[1]
Tolerance (ppm)/Maximum Residue Limit (mg/kg)

                                     U.S.
                                    Canada
                                   Mexico[2]
                                     Codex
Coffee, green bean
                                     0.03
                                       
                                       
                                       
Banana, whole fruit
                                     0.03
                                       
                                       
                                       
Mango, fruit
                                     0.03
                                       
                                       
                                       

                                       
                                       
                                       
                                       

                                       
                                       
                                       
                                       

                                       
                                       
                                       
                                       
Completed:  M. Negussie; 06/21/2011
[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.
