### UN IT E D S TA TES ENV IRO NMEN T AL PROTECTION AGENCY WAS HI NGTON, D.C. 20460

MEMORAND U M Date : 05-NOV-2015 OFFI CE OF C HEMI CA L S AFETY AN D POLL U TIO N PREVE N TI ON

ubje ct : Sa fluf enac il i nio n Pomegranat e. S umma ry o f Analytical C h e mi s try and R es idu e D a ta . P C Co d e : l 18 203 DP B arco dc: D422467 D ec i s ion N o . : 493885 Re g i s tration No
. : 7969

- 2 76 Petition No.: 4F8305 R eg ulatory Action: Sec. 3 Registration Ri s k Assess m e nt Ty pe : NA Case No.: NA TXR No
. : NA CAS No.: 372137-35-4 MRJD No.: 49434201 40 C FR: §180.649 

### F r o m : George 

### F. Kramer, Ph.D. , Senior

# Che**mi ~~**  Risk Assess m e nt Branch 1 (RAB 1) H ea lth Effects Di v ision (HED) (7509 P ) 

### T hro u g h : ldeliz Negr6 n- E ncamaci6n, Chemis t 

# '!1f:t "-._/,_/ 'j, /-. · , Mohsen Sahafeyan, Chemi st .. 1-a· 

## /z J- ,. . 

# /i,.,

-**I** .c:" Sc ien ce Adv isory Council for Chemistry (ChemSAC) / 

# /,1 HED (7509P) And Charles W
. S mith Ill , Bran c h C hi e f 

# C**~** RAB I , HED (7509 P) To : Kathryn Montague/Bethany Benb ow, PM Team 23 Registration Divis ion (RD ; 7505P) Exec uti ve S umm ary SaOufenac il (BAS 800 H ) is a broad

- spectrum herbicide developed by BASF. 

### It belongs to the herbicide mode-of-action Group 14 (ce ll m e mbr a ne d i srup t o rs)
. Safl uf e n acil ac t s through the inh i bition of protoporphy r inogen oxidase ( PP O). result ing in ce ll m emb ra n e damage and s ub s eque nt plant death. BASF bas su bmitted 

### a p roposa l for a n ew use of**Treev ix** **~** Powered by Kixor1c. He rbi c id e (EPA Reg. No. 7969

- 276. a 70% a i water-dispers i ble gra nul e (WG)) on pomegranate, dir ected at the base of th e tree trunks while targeting eme rged broad leaf weed s. BASF has peti tioned for the estab li shment of permanen t to le ran ces und e r 40 CF R §I 80.649(a)( I ) for sa fluf e n ac il, including it s m e tabolites and d eg rada tes, in or o n the raw ag ri c u ltura l com m od i ty ( RAC) li sted b e low. Co mpli a nce with th e t o le ran ce leve ls s pecified Pa ge I of9Satlufenacil Summary of Analytical Chemistry and Resi due Data D P# 422467 be low is to be determined by measuring only the sum of saflufenaci l , 2

- chlo ro-5-[3,6

- dihydro-3- methyl- 2,6-d i oxo - 4

- (trifl uoromethy l) -1 (2H)-pyr imidiny l]-4-tluoro-N-[[ meth yl( 1

- methy J e th y l)amino] sulfonyl]benzamide, and its metabolite s N-[2-chloro-5- (2 , 6-dioxo-4- (t

rifluorometbyl)-3,6-dih ydro- l (2H)

- pyrimidinyl)

- 4-fluo robenzoyl]

- N'- isopropy lsu lfamide and N

- [4-ch loro-2-fluoro-5-( { [ ( isopropy lamino)sulfonyl]amino }carbonyl)ph enyl]urea, calculated as the stoichiometric equivalent of sa flufen acil in/on the following plant commodity: 

## I Pom egranate 0.03 ppm The previously-submitted metabo li sm data for com, soybean , and tomato were adequate to eluc id ate th e nature of the residue in plants resulting from pre-plant/pre-emergence application. Th e HED R esidues of Concern Knowledgebase Subcommittee (ROCKS) determined that residues o f concern for the tolerance expression and risk assessment co n s i st of saflufenaci l , M800HJ 1 , and M800H 35 (Memo, B
. Dai ss, 06-JAN

-2009 ; 0359645). Thi s conclusion was translated to perennia l crops ( i .e. , tree fruits and tree nuts) w h ere sa tlufenaci l app li cation is directed to the weeds on the orchard floor (Memo, G. Kramer , 22

- JUL-2009 ; 0349938). As the proposed use o n pomegranate 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 saflufenac il , M800H1 I , and M800H35 for thi s crop . The nature of the residue in l ivestock is adequately under s tood based on accep table metabo.li sm studies conducted on lactating goats and lay in g hens. Th e re are no livestock feedstuffs associated with the proposed use; therefore. no changes in the existing tolerances fo r li vestock commodities are needed. The pet i tioner previously s ubmitted liqu id c hromatography/ mass spect roscopy/ mass spectroscopy (LC -M S /MS) ana lytica l enfo rcement method s for t h e determination of res id ues of the parent and its metab oli tes. BASF Method 00603 / 02 was developed for determi n ation of re sidues of saflufenaci l and its metabolites M800Hl 1 and M800H35 in diffe rent plant matrice s usin g LC-MS / MS. The limit of quantitation ( LOQ ) was 0.01 ppm for each analyte in food matric es (human consumption) and 0.025 ppm for each analyte in feed matrices ( li vestock consumpti on). A revis ed ve rsion (Method 00603 / 04) of th e current enforcement method was used for th e crop fie ld trials. The method was adeq u ate for data co ll ection based on acceptab le method va l idation and co ncurren t recovery data. The subm itted magninrd e of the re sidue data for pomegranate are adequa te. There are also adequate storage stabi li ty data to vali date the storage conditions and intervals of samples collected from the field tri als. Quantifiabl e res i dues were not found in any RAC sample. There are no regu lated processed commodities associated with pomegranate. No Codex , Canadian, or Mexican maximum residue limits (MRLs) have been estab li shed for saflufe na cil on pomegranate. Therefore , hannonization of MRLs and U
. S. tolerances is not an issu e at this time. This me morandum was rev iewe d by two peer r ev iewers of the ChemSAC, per C hemSAC Standard Operating Proce dures (SOPs). Regulatory Recommendation s and R es idue C hemistry De fi cie ncie s There are no residue chemistry issues that would preclude gran ting the fo ll ow in g permanent Page 2 of9Saflu fe nacil Summary of Anal ytical Chemistry and Re s idue Data DP # 422467 

### tolerances for residues of saflufenacil and its metabolites under 40 CFR 

### § l 80.649(a)(l ): 

## I Pomegranate 0.03 ppm 

### A human health risk assessm e nt will be prepared as a separate document (DP# 426933). 

### Background Saflufenacil is a broad-spectrum herbicide developed by BASF. It 

### belongs to the herbicide mod e -of-action Group 14 (cell membrane disruptors). Saflufenacil acts through the inhibition of PPO , resulting in c e ll membrane damage and subsequent plant death. Susceptible weeds develop s ymptoms 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 saflu fe nacil and its me tabolites M800Hl 1 and M800H35, and the physicochemical properties of the technical grade of saflufenacil are presented in Tables 1 and 2.

Table 1. Safl u fenaci l and Metabolite Nomenc lature. Che mi cal S tru ct ure

Co mm o n na me Com pany expe rim e nta l nam e IUPAC n ame CAS name CAS r eg istry numbe r End -u se prod u c t (E P) Chem i ca l St ru c ture

Common n ame C h em i ca l name Chem i ca l St ru c ture

Commo n na m e Sa fluf e nacil F F F F C l 0

B AS 80 0 1-J (sy n onyms: AC 43 3 37 9, B AS F R eg. No
. 405444 9) N -[2- c hloro-4- fluoro-5- (3 -meth y 1-2 , 6-d ioxo-4- (tri fl uo rom eth yI )-3 , 6-d ih yd ro- I (2H)

- py rim id i
. n y l ) be nzoy I ]-N-i s opropy 1-N-m e th yl s uI f amid e 2- c h l o ro-5-[3 ,6

- dih y dro-3-m e th y 1-2 , 6-d ioxo -4

- (tri fl uoromcthy I )- 1 ( 2/1 ) -py ri midi ny l)-4- tluoro -N- [[m e th y l ( 1

- m ethy l eth y l ) amin o ] s ul fon y l]b e nzamid e 372 137

- 3 5-4 S harp e n ® Powe r ed by Ki xor'° H e rbi c i de (EPA R eg. No
. 7 969-2 7 8 ) (2.8 5 lb ai/ga l SC formulation )

M800 Hl I F F F F**~** 0 C l 

# I H 0 H

### N......._**~/ ~**  I I 

### o o e rr,

N-[2 -chlo ro -5- (2, 6-di oxo - 4

- (t ri fl uoro m et

hy l )-3,6 -dih y dro- I (2 /-f)-py rimidin y l)-4- flu o ro be nzoy l)- N' -i so pro p y l sul famid e 

# ft

# F~I C l HOH**~ ~**  N........_ ll / NY CH3 H , N N S

- H II 0 0 C H 3 M8 00 H3 5 Page 3 of9Saflufenacil Summary of Analytical Chemistry and Residue Data DP# 422467 T ab le l. Saflufenacil and M e tabol i te No m e nc l ature. Chem ical name N

- r4

- chloro

- 2

- nuoro-5-( {L(isopropylamino )s ulfon y l lwnin o }carbonyl)phenyl)urca Tab l e 2. Phy sic ochemical Prop e rt i es of Tec h n i cal Gra d e Saflufenac il. Param ete r Va lue Melting point Average = 189.9 °C
. peak max = 193.4 °C pl-I 4.43 of I % so luti on at 25 °C Bulk Density (ambient 0.661 k g/L (free fall). 0.736 kg/L ( packed ) temp.} 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 bufTer: not dctcnnined due 10 degradation in pH 9 buffer Solvent solubility (20 °C) in g/ 100 mL: 19.4 acetoni1rile: 24.4 dichloromcthane: 55.4 N,N

-dimethy lformamide: 27.5 acetone: 6.55 ethyl acetate: 36.2 tetrahydrofuran: 35.0 bu1yrolactone: 2.98 methanol: 0.25 iso propyl alcohol: 0.23 l o lu ene: < 0.0 I 1 -oc tanol: <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 Di ssocia tion constant (oK.) 4.41 Octanol/water partition Mean Log P ow = 2.6 ( Pow = 368.3) coefficient UV/ visible absorption wavelength maximum: ''''"" = 271.6 nm spectrum extinction coefficient : t "" 9709 L / mol-cm Reference: BASF Registration Document Number ( DoclD ) 2005/1026464. 

### 860.12 00 D i rectio n s fo r Use BASF has submitted a draft s upplemental labe l for ofTreev ix® Powered by Kixo r ® Herbicide (E PA Reg
. No. 7969-276). Information per taining to the proposed e nd -use product is li sted in Tab le 3. A s ummary of th e proposed use patterns is detailed in Tab le 4. Table 3. S umma!"' o f Proposed End-Use P r o d u c t . Reg. ai (%of Formulation Target Trade Name No. formulation) Type Target Crop P ests Label Date Treevix 00 P owered 7969- 70 WG Pomegranate Broad leaf Draft lab el by Kixor® 276 weeds submitted H erb icide AUG-2014 Table 4. S ummary of Dir ec tion s for Use of Sa flufcna c il. Applie. Timing. EPA Max Single la. x Seasonal Type. and Reg. App
. Rate (lb Max. # Apps App. Rate (lb RTI Piii Use Directions and Equip. No. ai/ A) per year ai / A) (days) (days) Limitations Pom eg ranate Post, 7969- 1. 0 

### n. oz/A 4 4 .0 n. oz/A 2 1 0 The fourth application mu st Di rected to 276 (0.044 lb ail A) (0. 176 lb ailA) be made during tree Orchard donnancy. Floor 

### Conclusions: The submitted use direction s fo r Treev i x ® Powered by Kixor® Herbicide are adequate to allow evaluation of the resi d ue data relative to the proposed use.

Page 4 of9Saflufenacil Summary ofAnalytical Chemistry and Residue Data DP # 422467 

### 860.1300 Nature of the Residue - Plants Reference List: Memo , G. Kramer, 24-JUN

- 2014; 0414003 

### The previously submitted metabolism data for corn, soybean , and tomato were adequate to elucidate the nature of the residue in p l ants resulting from pre-plant/pre-emergence application. T he HED Residues of Concern Knowledgebase Subcommittee (ROCKS) determined that residues of concern for the tolerance expression and risk assessment consist of satlufenacil, M800Hl 1 , and M800H35 (Memo, B. Daiss , 06-JAN-2009; D359645). This conclusion was translated to perennial crops (i.e., tree fruits and tree nuts) where saflufenacil applicati on i s directed to the weeds on th e orchard floor (Memo, G. Kramer, 22-JUL-2009; D349938). As the proposed use on pomegranate is also directed to weeds at the base of the plants , HED concludes that the residues of concern for the tolerance express i on and risk assessment also consist of sa

flufenacil , M800Hl 1 , and M800H35 for this crop. 860.1300 Nature of the Residue - Livestock The nature of the residue in livestock is adequately understood bas ed on acceptab le metabolism studies conducted on lactating goats and laying hens. There are no livestock feedstuffs associated w ith the propose d use ; therefore , no changes in the existing tolerances for livestock commodities are needed.
860.1340 Residue Analytical Methods Reference List: Memo , G
. Kramer , 24-JUN-2014; 0414003 

### BASF Method D0603 / 02 is the current enforcement method for determination of residues of satl ufenacil and its metabolites M800Hl 1 

### and M800H35 in different plant matrices. Residues of saflufenaci l and its metabolites M800Hl 1 and M800H35 were extracted with me t hanol:water (70:30; v:v). The methanol extract was evaporated and recon sti tuted in methano l: water (50:50; v : v) for LC-MS/MS analysis
. Two transitions per analyte were monitored for the quantitation and confirmation of saflufenacil, M800H 11 and M800H35. The re s idues of each analyte were expressed as parent equivalents using a molecular weight conversion factor (1.0 for safl ufenacil , 1.06 for M800Hl 1 , 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). A revised vers ion (Method D0603 / 04) of the current enforcement method was used for the crop field trials. Method D0603 / 04 has been revised from the established enforcement method, Method 00603 / 02 , to add ins tructions for determination of metabo lite M800H02 (N-[2-chloro5

- (2, 6-di oxo-4-( trifl uoromethyl)-3 ,6 -dihydro

- l 

### (2H)-pyrimidi n y 1)-4-fl uorobenzoyl ]-N -isopropy 1- N

- meth ylsul famide)
. A complete method descrip t ion and method validation data for Method D0603 / 04 were included in MRJD # 49312401. In support of the revised method , BASF has also submitted the results of an IL V of the method (MRJD# 49118203). Method D0603 / 04 is adequate for data collection in the submitted field trials based on acceptable concurrent recovery data. Recoveries were generally within the acceptab le range of 70-120 %. As the dataacquisition method i s essentiall y identical to the enforcement method with regards to the residues o f concern and it was successfu ll y validated, H ED concludes that an adequate enforcement Page 5 of9Saflufenacil Summary ofAnalytical Chemi s try and Residue Dara DP# 422467 

### method is available to enforce a tolerance for residues of saflufenac il in pomegranate. 

### 860.1360 Multiresidue Methods (MRM) 

### Sa flufenacil and it s me tabolites M800Hl I 

### and M800H35 were screened through the MRM described in the United States Food and Dru g Admjnistration (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 M800Hl 1 and M800H35. Since the analytes are not N-methyl-carbarnates, naturally fluorescent or substituted urea derivatives, the tests using Protocol A and G were not performed.


### 860.1380 Storage Stability The field residue samples were stored frozen a maximum of33 days (1. l months) from harvest to extraction. All samples were analyzed within 1 day of ex'tract ion. Adequa t e storage stability data are available in/on various cro p commodit ies (com (grain , forage, stove r ); soybean (seed , fo rage , hay); orange (fruit , pulp , juice, oil); radish (root); grape (raisin); and garbanzo bean (seed)] indicating that residues of saflufenac il , M800Hl 1 , and M800H35 are stable in/on alJ tested commodities during frozen storage for up t o 548 days (M RID No. 47523801). These data a re acceptable to s upp o rt the s torage conditions and durations of sampl es from the submitte d field trials for residues of safl ufenacil , M800H 11 , and M800H35.


### 860.1480 Meat, Milk, Poultry , and Eggs There are no livestock feedstuffs associated with lhe proposed use; therefore , no c hange s in the existing tolerances for li vestock commodities are needed.


### 860.1500 Crop Field Trials DER Reference List 4943420 I .der.docx 

### Four field trials were conducted in the United States during the 2013 growi ng season in the North American Free Trade Agreement (NAFTA) Growing Zone I 0 (CA). Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated plot received four banded ground applications of a 70% WG formu lation of saflufenaciJ (BAS 800 OlH). 

### The app li cations were mad e to the ground of th e pom egranate orchard (beneath the trees and/or i.n areas between row s) at 0.0433-0.0466 lb ai/A/application, for a total seasonal rate of 0.177-0. I 82 lb ai/A (lX). The first application was made in February during wi.nter dormancy (prior to spring bud break or onset of flowering) fol l owed by three applications made at fruiting. Retreatrnent intervals (RTis) were 189-201 days between the first and second applications and 20-21 days between the second, trurd , and fourth applications. App li cation s we re made using ground equipment in spray volumes of

- 15-37 gal / A. A methylated seed oil (MSO) was added to the spray mixture for each of the applications. Samples of pomegranate were harvested at a O

### day PHI. Page 6 of9Sanufenac il S ummary ofAnal yt i ca l Chemistry and Residue Data DP# 422467 

### Fo ll ow in g four banded gro und applications of the 70% WO fo m1ul a ti o n of s aflufenaci l at a total seaso nal rate of0 .1 77 -0.18 2 l b ai/A , combined residues (and per-tria l averages) ofsaflufenacil, M800H l l , and M800H35 were below the LOQ (<0.03 ppm ) in/on a ll san1p les of pomegranat e harvested at a 0-day PHI (Table 5)
. Re si du e decline was not investigated. Residues of M800H 11 and M800H35 were not converted to parent equivale nt s because they were <LOQ.

Tab le S. S umm a r y of R es i dues fr om Pomegranate Fi e ld Trial s with Sa nuf e oac il. Total Residues (ppm) Application Rate Pl-11 C rop Matrix Analytt: (lb ai/A) (days) nl Min. 2**Max .~**  Ll\FT3 l-LAFT 3 Median 3 Mean 3 SD' Pomegranate Sanufenaci l 0. 177

-0.182 0 4 <0.0 1 <0.0 1 < 0.01 < 0.0 1 0.0 1 0.0 1 N I A M800 111 l 4 <0.0 1 <0.0 1 < 0.0 1 < 0.0 1 0.01 0.0 1 N I A M800H35 4 <0.0 1 <0.01 < 0.01 <0.0 1 0.01 0
. 0 1 N I A Co mbined Res i dues4 4 <0.03 <0.03 < 0.03 <0
. 03 0
. 03 O.Q3 N I A 1 n = number of fi e ld trials
.**~** Va lu e s based o n total numb e r of sample s . 3 Va l ue s based on per-tria l averages. LAFT =lowest average lield tri al , l IAFT = hig hcs 1 ave rage field trial. SD = standard deviation. For comp ut a tion of the LAFT. HAFT. median, mean , and s tandard deviation. va lu es < LOQ are assumed to be at the LOQ (0.0 I ppm). N / A 

### = not applicable. 4 Combined re s idue s of sa llufenacil. M800H 11 , and M8001

-135
. 

### Conclusio ns: The s ubm itted res idue data are adequate to fu lfill data requirements for pomegranate. The number and locations of the cro p field trials are 

### in general acco rdance with OCS PP G uid eline 860.1500 (Table 6). T he ava ilabl e da ta w ill s upp ort the proposed u se pattern.

Table 6. Tria l N umb e r s an d Geogra p h i cal Locatio n s . o. NAFT A Growing Zone Crop Trials I 2 3 4 5 6 7 8 9 10 11 12 Total P

omegra nate Sub. 4 4 R cq. 1 3 or2 1 As per Table I of 860.1500 for pomegranate, 1hree trial s with a minimum of 6 srunp lc s or 1wo trial s with a minimum of 8 samples arc required. Geographic distribution is not s pecified for crops requiring $3 !rial s: however . per Tab l e 6 of 860
. 1500. Zone I0 accou ni s for 99% of U.S. pomegranate production
. 

### The resid ue data for pomegranate s were not entered into th e Organi zat ion for Eco nomic Coope r a ti o n and D eve lopm e nt (OECD) MRL ( maximw11 resid ue li mit) Ca lculato r as a ll of the residues we re < LOQ. The r e commended tol e rance for th e combined r es idue s of satlufenac il and its m etabo li tes M800Hl 1 and M800H35 , expre ssed as parent eq ui vale nts , is 0.03 ppm for pomeg ranate.


### 860
. 1520 Processed F ood and Feed There are no regu lated processed commodities assoc iated with pomegranate.

Pa ge7of9Satlufenacil Summary of Analytica l Chemistry and Residue Data DP# 422467 

### 860.1650 Submitta l of Analytical Reference Standards Analytical standards of saflufenaci l (expiration date: 511114), M800Hl l (metabolite 5303307 ; expiration date : 7 / 1/14) , and M800H35 (metabolite 5303308; expirati on date: 7/1 / 14) are currently availab l e in the National P esticide Standards Repository [source: personal communication with T. Co l e of ACL/BEAD , 3 / 6/14]. The registrant subsequen tly recertified the lots in the repos itory and submitted updated Certificates of Analysis for saflufenacil (expiration date: 2 / 1/18).


### 860.1850 / 860
. 1900 Confined/Field Accumulation in Rotational Crops Rotationa l crop studies are not germane to this petition as pomegranates are not rotated with other crops. 

### 860
. 1550 Proposed Tolerances BASF has petitioned for the establishment of permanent tolerances 40 CFR §I 80
. 649(a)( 1) for saflufenaci l , including its metabolites and degradates, in or on the agricu ltural commodity 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 -di oxo-4-(trifluoromet hy l )

- 1(2ff)-pyrimi dinyl]-4-fluoro- N

- [[ methyl(l-methylethyl)amino]su l fony l] benzamide, and it s metabolites N -[2-chloro-5-(2 ,6-dioxo-4-( trifluoromethy l )-3 ,6-dihydro-1 (2ff)

-pyrirnidinyl)-4- fl uoro benzoy l]-N

- isopropylsulfamide and N-[4

- c hl oro-2-fluoro

- 5- ( { [ (i sopropylarnino)sulfony l] amino} carbony l)pheny l]urea , calculated as the stoichiometric equivalent of saflufenac il inion the following plant commodity:

Ta b l e 7. Toler a nce**umm ~**  for Sa fluf e n ac il. Proposed HED-Recommended Cor rect Commodity Conunod ity To lerance (nnm) Tolerance (ppm) Definition/Comments Pom e !rranate 0.03 0.03 

### HED i s not recommending for any revision to the pet itioned-for tolerance (see Table 7): No Codex, Canadian , or Mexican MRLs hav e been estab lished for saflufenacil on pomegranate.**Therefore ~**  

### harmonization of MRLs and U.S. tolerances is not an issue at this time.



### List of Attachments Attachm ent I. International Residue Lim it Status (IRLS) sheet.

cc: G
. Kramer (RAB I ) ROI: RABI Chemists (5 / 6/ 15) G.F. Kramer: SI 0957:PY-S: ( 703)305-5079:7509P : RAB I Page 8 of9Saflufenaci l S ummary of Analytical Chemistry and Residue Data DP # 422467 Attac hm ent 1. IRL S Sheet. 

### International Residue Limits Status 

## s fl 

## u

a u enac il (I 18 20" D J; ate o f 

## R equest: 4/ 24/2015) S umm ary of U
. S. an d lntemationa J Tolerances and Max imum Residue Limits R es idue Definilion: U.S. Canada Mexico 2 Co dex 40 CF R 1 80.649: 2-chloro-5-[3 , 6-dihydro-3-methyl- Saflufenacil Plant: s aflufenacil , inc ludin g its 2,6-dioxo-4-(tri fluoromethyl )

- Th e re s idu e metabolites and degrada tes , sum of I(2H) -py rimidin yl)

-4-fluoro-N- i s not fat s aflufenacil , 2

-chloro

- 5

- (3,6- [[ methyl{I

- so lu b le d ihydro-3-methyl-2 , 6-d ioxo-4- methy lethyl)arn ino]su I fonyl)benzam (rrifluoromethyl)-1 (2H)- ide , including the metabolites N'-{2

- pyrim id in yl]-4- flu oro-N- chloro-4-fl uoro-5-[ 1 , 2 , 3 , 6- [[met h y l( I

- tetrahydro-2 , 6-dioxo-4- met hy l ethy l) am ino Jsu I fonyl)benza (trifl uorome th y l ) py rimidin

- 1- mide , and its metabolites N-[2- y l]benzoy l }-N-isopropyl su lfam ide chloro-5-(2 , 6-dioxo-4- and N-[4-chloro- 2-fluoro-5- (trifluoromethy l )-3 ,6-dihydro- ( {[(isopropylamino )sulfonyl] I ( 2 H)-py rimidin y l)-4- amino} carbony l )phenyl]urea fluorob e nzoyl]- N

is opr o p y l

s ulfamide and N -[4- Livestock: 2

- chloro-5-[3,6-dih ydrochloro- 2 -fluoro-5- 3-methy l-2,6-dioxo-4- ( { [( iso prop y lamino )s ul fonyl]amino (trifluoromethyl ) -1 ( 2H)- } carbon y l) phenyl]urea , calculated py rimidin y l)-4-tluoro- N -[[methyl( Ias th e s toichiometric equivalent of methylethyl ) amino ]sulfony l]benzam sa flufena cil ide Comnwdity 1 Tolerance (ppm)/ Maximum Residu e Limit (mg /kg) U.S. Canada Mexico 2 Codex Pome g ranate 0.03

Co mpl eted: M. Negussie; 04 / 24/ 15 1 Include s only commodities of interest for this action. T olerance values s hould be the HED recommendations and not tho se propo sed by the applicant. 2 Me xico adopts U.S
. tolerances and/or Codex MRLs for its expon purpo s e s .

Page 9 of9Satlufenac il/ PC Co de 118203 /Jnterre gio nal Re searc h Project No. 4 B .7.6 R es idu es Re s ulting 

### from Sup e rvi s ed T rial s (A nn ex H A 6 .3 ; Ann ex I IT A 8 . 3) B . 7 . 6.1 R es idu es in Ta rge t C rops B.7 . 6. l.J P o m egra nat e

Re p ort:

G uid e lin es :

GL P Co mpli an ce: Acce pta bili ty:
Eva lu ato r :

otc : Thi s DER was originall y prepared under contract by Versar. I nc. (6850 Versar Center
. Sp ringfield, VA 22 151 ; submitted 3 / 6

/ 15). The DER has been r e viewed by HE D and r ev i sed to reflect current Office of P esticide Pr ograms ( OPP ) policies. EXECUTIVE 

### SUMMARY Th e Inte rreg ional Re search Projec t N u mbe r 4 (IR-4) has s ubm itted fie ld trial d ata for satlufe n ac il o n pomegranate. Four fi e ld trials were conducted in the U nited States during the 2013 growing seaso n in th e North A merican Free Trade Agreement (NA.FT A) Growing Zone 10 (CA)
. Each trial co n s isted of one untreated p l ot and one tre ate d pl o t. A t each trial lo ca tion , the treated plot received four banded gro und application s of a 70% water-di spers ibl e g ranu le (W O) formu lation of satlufe n ac i l (BAS 800 

### OIH). Th e a ppli cation s we re made t o the groun d of th e pomegranate orc hard (be neat h the tree s and/or in areas between rows) al 0.0433 -0.0466 lb a i/Nap plication , fo r a total seasonal rat e of 0.17 7 -0.18 2 lb ai/A. The fir st application w as made in February during win t er dormancy (prior to spring bud break or o n set of flowering) followed b y thre e appl ications made at fruiting. Retreatme nt interva ls (RT i s) were 189-201 days betwe e n the fi rs t and seco nd applications and 20-2 l da ys between the seco nd , third , and fourth app lic atio n s. App lic ations were made u s ing ground equipment in sp ray volumes of

- 15-37 ga l / A. A m ethy late d see d oil (MSO) was added to th e s pr ay mixture for each of the applications. Sampl es of p o m egranate were harvested at a 0-day pre harves t in t erval ( PH I )
.

Pa e I of7 MRID # 4943420 ISatlufenacil/PC Code 118203 / Interregional Research Project No. 4 All samples were maintained frozen at the testing facilities , during shipping to the laboratory, and were stored frozen until analysis
. The field re sidue samples were stored frozen for a maximum of 33 days (1.1 months) from harvest to extraction. All samples were analyzed within l day of extraction. Adeq uate storage stabil ity data are avai lable ( DP#3 49938 , 7/22/ 09 , G
. Kramer) indicating that residues of saflufenaci l and its metabolites M800Hl 1 and M800H35 are stab le during frozen storage for up to 548 days in /o n vario u s crop commodities including: com (grain, forage, stover); soybean (seed, forage , hay); orange (fruit , pulp , juice , oil); radish (root); grape (ra is in); and garbanzo bean (seed). These data are acceptable to support the storage conditions and durations of samples from the submitted field trials. Samples were analyzed for residues of safl u fenaci l and metabolites M800H 11 and M800H35 using a high-performance liquid chromatography method w ith tandem mass-spectrometry detection (LC/MS/MS), Method 00603 / 04 , which is essentially identical to the enforcement analytical method for saflufenaci l in plants. Acceptab le co ncurrent recoveries were reported for samples ofpomegranate fortified with each analyte at 0.01-1.0 ppm , thus validating the method
. The limit of quantitation (LOQ; determined as the lowest level of method validation , LLMV) was 0.01 ppm for each analyte, for a combined LOQ of 0
. 03 ppm (metabolite residues not expressed in parent equivalents). The fortifi cation l evels used in concurrent method recovery were adequate to bracket expected residue levels. Recoveries and residues in treated samples were not corrected for residues in controls. Following four banded ground app li cations of the 70% WG formulation of saflufenacil at a total seasona l rate of 0.177-0.182 lb a i /A, combined residues (and per-trial averages) of saflufenaci l , M800Hl 1, and M800H35 were below the LOQ ( <0.03 ppm) inion a ll samples of pomegranate harvested at a 0

- day PHI. Residue decline was not investigated. Residues of M800H 11 and M800H35 were not converted to parent equival ents because they were < LOQ
. I. 

### MATERIALS AND METHODS A. MATERIALS

Table B.7
. 6.1.1-1. Nomenclature for Saflufenacil and Metabolites oflnterest. Chemical Structure F Cl 0**~** CH, 

# I H 0 

### I :::::-.....

### N'-..~/NYCH, 

## I N

# N~O II f 0 0 CH, F 

### I F CH, Common name Saflufenacil Company experimental name BAS 800 H (sy nonyms: AC 433 379. BASF Reg. No. 4054449) lUPAC name N' -[2-ch loro-4-lluoro-5

- (3 -meth y l-2 , 6-dioxo-4-( trifl uoromethy I )-3 ,6-d ihydro-1 (2/-/)

- pyrimidinyl)benzoyl]-N-isopropyl-N-methylsulfamide CAS name 2-ch Joro-5-(3 , 6-dihydro-3

- methyl

-2 , 6-d ioxo-4-( tri fl uorometh y 1)- 1 (211)

- pyrim id iny I ]-4- fluoro-N-[[ methy I( 1-methylethy I )amino]su lfon y l] benzam id e CAS registry numb er 372137

- 35-4 E nd

- use product (E P) Sharpen® Powered by Kixo r® Herbicide (EPA Re g. No. 7969-278) {2
. 85 lb ai / gal SC formulation)

Pa e 2 of7 MRJD# 4943420 ISafl uf enac il/ P C Co de 118 203/ln terreg ional Resear c h Pro j ec t No. 4 T a bl e B. 7.6. 1.1

- 1. No m e ncl at u re for Safluf enacil and Metabolite s oflnterest. Chemical Structure

Common name M800Hl I F F F 0 F H 0 H

### ,~_......Nye~ 

### II o o**c~**

Chemical name N -[

2

- ch lo r o - 5- (2.6 -d ioxo-4- ( tri n uoromcthy 1 )-3 .6-d ihydro- I (2 H)

-pyri midi ny I )-4- tl uorobcnzoy l]- N' -isopropy l s u

I famide C hemic a l Struc tur..: F

Common name M800H35 Chemical name N -f

4

-chloro-2-n uoro - 5-( { f(

i sop r opy lam ino )su I fony 

### !lam ino} carbony l)pheny I] urea 

### B. Study Des ig n 1. 

### Test Procedure Four re s idue trials in/on p omegranate wer e co ndu c ted wi th a 70% WG fo rmul at ion of saflufenaci l (BAS 8 00 OIH) during the 2013 growing season. Field trial locations by NAF TA growin g zo ne a r e summ a ri ze d in Table B
. 7 .6.J. l

- 2
. T h e tria ls sepa rate d by <2 0 mil es have been assessed for ind e pe nd e n ce as d eta iled in the table be l ow. Beca u se the ge o gra phic area suitable for pomeg ranate cu lti va tion in th e U
. S
. is limi ted, HED h as co n c lud e d that these trials may be conside re d se parate trial s for purpos e s of 860.1500 data req uire me nt s.

I ndependen t Trial Determination' Crop Trial Nos.**fferences~** Decision Pomegranate 13- CA02 & 13-CA03 Sarne location and varietv Separate Timing: 7- to 8-day olT-sct in application and harvest Sprav volume:

- 15 GPA vs. - 33 GPA *No other dilTercnces in criteria 1 All assessments are based on the replicate trial guidance presented in draft memo 568

_ Criteria for I ndependence ofTrials 04 /2312013 (EPA and PMRA). ? The petitioner indicated that the CA02 & CA03 trials were differentiated by separate s pray solutions prepared, > 25% dilTerence between s pray rate s, different fcnilizers within spray mix (an1 m onium sulfa te vs. urea ammonium nitrate). and backpack sprayer vs. tractor-mounted s pray equipment being used at the same location.

Pa oe 3 of7 MRJO # 4943420 ISanufenacil/ P C Co d e 118203 / lnterregiona l Re searc h Proj ect No. 4 Table B. 7 .6.1.1-2
. Trial N umb ers and Geographica l Location s . No. NAFTA Gro win g Zone Crop Trials I 2 3 4 5 6 7 8 9 1 0 II 12 Total Po me grana te Sub. 4 4 Rcq
. 1 3 or2 1 As per Table I o f 860
. 1500 for pomegranate. three trials w ith a minimum of 6 samples or tw o trial s with a minimum of 8 sa mple s are req uired
. Geographic distribution is not s pecified for crops requirin g 9 trial s: howc\'er. per Table 6 of 860.150 0
. Zone I0 accounts for 99% of U.S
. pomegranate production. Locations and detailed use patterns for the trials are provided in Table B.7.6.1.1-3.

Tab le B .7.6. 1.1 -3. Stud y Use Pattern. Location: Ci ty. Rate per Reirealment S tai e; Year End-u se Method of Appl i cation: Timing Volume /\pplication (Trial ID) Product 1 of /\pp lic alio n (gal/A) (lb ai / A) Parlier. CA: 70%WG I. Banded to the ground: 1 5.2 0
. 0439 2013 dormant (13-CA02) 2. Banded to the ground: fruiting 14 .9 0.044 1 3. Banded lo the ground: fruiting 15 .0 0.0446 4. Banded to the ground: fruiting 15.0 0.0446 Parlier. CA : 70 % WG I
. Banded to the g r ound: 30.5 0.0 44 6 201 3 dormant ( 1 3-C/\03) 2. Banded to the ground: fruitin g 32.6 0.0 -1 53 3. Banded to the ground: fruiting 31.8 0.0444 4
. Banded to the ground: fruiting 33.0 0.0465 Da vis. CA: 70%WG I. Banded 1 0 the ground: 32.0 0.0 -138 2013 dormant ( 13- CA0 4 ) 2. Banded to the ground: fruiting 35.8 0.0449 3. Banded to the ground: fmiting 37.I 0.0465 4. Banded to the ground: fmitin g 37.2 0.0466 Yuba C ity . C A: 70%\VG I. Banded 10 ll1e ground ; 16.8 0
. 0433 2013 dormant ( 1 3-C/\05) 2. Banded to the g round: fruiting 17 .6 0.0453 3. Banded to the ground; fruiting 17.6 0.0453 4. Banded to the ground : fruiting 17.2 0.0443 1 70% WG formulation ofsaflufcnacil (BAS 800 01 H: Trcevix Powered by Kixor Herbicide). 2 M SO 

### = me th y lated seed oi l. In terva l (days)



## -- 201 2 1 20



## -- 201 21 21



### -- 197 2 1 20



## -- 1 89 21 20 Total Rate (lb ai/ A)

0. 177

0.18 1

0.182

0.178 Surfactant/ Adjuvant2

MSO

MSO

MSO

MSO

Pomegranates were grown and maintain ed according to typica l agric ultural practices
. Irri gation was used to supp lement rainfall as needed at all trial s ites. No w1Usua l weather condition s were reported durin g the study
. 

### Sa mple Handlin g a n d P r eparation Duplicate control and treated samp l es of pomegranate s were harvested on th e day of the final applica ti on after the spray had dried (0

- day PHI ). The pomegranates were quartered and eithe r one quarter or opposite quarters were retained as samples. Samples were placed in frozen storage at the field s ites within

- 2.75 hours of collection and were shipped frozen within 5 -1 6 days of co ll ect ion by overnight carrier on dry ice to the analytica l labo ratory, BASF Crop Protection (Research Triangle Park, NC) fo r residue analys is. Samples were maintained frozen (

- -8 ° C) at the ana lytical laboratory prior to homogenization and analysis. In preparation for anal ys i s , samp les were ground in the presence of dry ic e.

Paoe 4 of7 MRID # 49434201Saflufenacil / PC Co d e 118203/lnterreg io n al Research Project No. 4 

### 2. D es crip t ion of A n a ly tic a l Procedures Sa mple s were analyzed for res idues of saflufenacil and its metabo l ites M800 H 11 and M800H35 using LC/MS / MS , Met h od D 0603 / 04 , which is essen ti ally identical to the enforcement analytical meth od for s aOufenacil in plants , Method D0603 / 02 , tha t was previously reviewed by the Agency ( DP# 349938, 7 / 22/ 09 , G. Kramer). A comp lete de sc ription of the me thod was included in th e s ubmi ss ion. Briefly, residues of saflufenacil , M80 0H l 1 , and M800 H 35 were extracted with methanol:water (70 : 30; v:v). An 

### a l iquot of the extract was concentrated , and re s idues in 

### the aqueous re m ainder we re acidified with 0.1 M trifluoroacetic acid (TFA) and then part it ioned with eth y l acetate:cyclohexane (70:30; v : v). An 

### ali quot of the organic ph ase was evaporated an d reconst i tuted in me th anol:water (50:5 0 ; v:v) fo r LC/ MS / MS ana lysis. The LOQ, dete nn in ed as the LLMV, was 0
. 0 1 ppm for each an a lyte in pomegranates, for a combined LOQ of 0.03 ppm (metabolite resid ues not expressed in parent equivalen t s)
. T h e petitioner stated that th e li mit of de tection (LOD) was 20% of the LOQ (0.002 pp m) per analyte. II
. RESU LT S 

### AN D DI SCU SSION Method perfo rmance was evaluated by use of concurrent re cove ry s am pl es. Samp l es of untreated pomegTanates were fortified with satlufenacil , M800Hl I , and M800H35 at 0
. 01 and 1.0 ppm eac h. Recoveries were generally within the acceptable range of 70-120 %; the refor e , the me thod was considered valid for the analysis of saflufenacil , M800H 11 , and M800H35 residues in pome g ranat es (Table B.7.6.1.1-4). The fortificat io n leve ls bracketed the measured res idues
. Co ncurrent r ecove ries we re not corrected for apparent residu es in controls. Th e de tecto r response was lin ear (coefficient of determ i nat ion, 

### r2 2: 0.9813) with in the range of 0.025-0.50 ng/ mL. Represe ntati ve c hromatograms of contro l samples, fort i fied sam p les, and treated s amp les we re provided
. The co n tro l c h ro matograms genera ll y had no peaks of inte rest above th e c hromatographic backgroun d. Th e fort ifie d sam p le c hromatograms co ntai ne d o nl y th e analyte of in terest , an d peaks we re symm etrica l a nd we ll defi ned. Appare nt resid u es in co n tro ls we r e below the LOQ in/on al l samples
. T he repo rted res id ue va lu es were not corrected fo r apparent re s id ues in controls
. Res i d ues ofM800 H l 1 and M800 H 35 were not conve rte d t o pare nt e qu i valents because al l res idu es were nonquantifiable.

Tab le B
. 7.6. 1.1

- 4
. S umm a ry o f Pro cedur al/Co n c urre nt Recoveries o f Sa flu fe nac il a nd i ts Me ta bolit es M 8 00H 11 a nd M 8 00H3 5 fr o m P o megra n a te. Fortification Sample M atri x Anal y te Level (ppm) Size (n) Rccovc:rie s 1 ( % ) Po megr-.matc Saflufcnacil 0.0 1-1. 0 2 M800Hl I 0.0 1-1. 0 2 M800H35 0.01 -1. 0 2 1 Concurrent rccovt:rie s wt:re not corrected fo r apparent residues in control s . 2 Standard deviation i s not calcula ted for sample sizes < 3. 90
. 90 92.93 68: 100 Mean ± Std. Dev. 2 (%) 90 93 84


### The fi e ld re s idue samples were stored frozen a maximum of 33 day s ( 1.1 months) from harvest to extract ion (Table B
. 7
. 6
. 1.1

- 5)
. A ll 

### samp les we re ana l yzed w ith i n I day of extractio n. Ad eq uate storage stab ili ty data are avai lab le ( DP #3 49938 , 7 / 22 / 09 , G. Kramer) in dicatin g that res idu es of saflufenacil and it s metabo l ites M80 0Hl l and M800H35 are stab le during froze n
Paoe 5 of7 MRID # 49434201Saflufenacil / PC Code 1 18203 / ln terreg iona l Resear ch Project No. 4 

### s torage for u p to 548 days i n/on vario u s crop commodities includ in g : corn (grain , forage, s tover); soybean (seed, fo rage, hay); orange (fruit, pu lp, j ui ce, o il ); radi s h (root); grape (rai s in); and garbanzo bean (seed)
. T hese d ata a r e acceptable to support the s torage conditions an d d u rations of samples from t he subm itted fie l d trials.

Tab le B. 7 .6
. 1.1-5
. S umm a r y of S t o r age C ondi t ion s . Storage Actual Storage Matrix Temperature (°C) Duration 1 I nterva l of Demon s trated Storage Stability Pomegranate fruit -8 20-33 days Residues of saflufenacil and its metabolite s M800H I I and (0.9

- 1.1 months) M800H35 are s table during frozen storage for up to 548 day s in / on various crop commodities including: corn (grain, forage, stover); s oybean (seed, forage , hay); orange ( fruit, pulp , juice. oil); radi s h (root); grape (raisin); and ga r banzo bean (seed). 2 1 Interval from harvest to extraction. Samples were analyzed w1thm I day of extraction. 2 OP #3 49938 , 7 1 22 1 09, G. Kramer. 

### The res u lt s from the s ub m i tted field tria ls are presente d i n Tables B .7
. 6. 1.1- 6 and B. 7.6. 1. 1

-7. Fo ll owi n g four b anded ground app li ca ti o n s of the 7 0 % WG formu l ation of satlufenaci l at a total seasonal rate of 0 .177 -0.182 lb ai/A, combined resid ues (an d per-tri al averages) of satl ufe n acil, M800 Hl 1 , and M800 H 35 were below the L OQ (<0.03 pp m) in/o n all samp les of p o m egranate harveste d at a 0-day PH I. R esidue decli n e was not i nves t igated. R esid ues of M800H l 1 and M800 H 35 were not converted to parent equivale n ts beca u se th ey were <L O Q.
Ta bl e B
. 7
. 6.1.1

- 6. R es idue Data fr om Pom eg ran a t e Fie l d Trial s w it h S afl u fe n a cil. 1 Location: City. Residues 2 (ppm) [ Average] State; Year (Tr ial Crop Rate PHI Combined ID) Zone Variety Matrix (lb ai / A) (days) Saflufenacil M800H I 1 3 M800H35 3 Residues 4 Parlier, CA; 2013 10 Wonderful Fruit 0.177 0 ND,ND ND,ND ND,ND < 0.03, < 0.03 (13-CA02) [<0.0 1 ] [ <0.0 1 ] [<0.01] [< 0.031 Parlier, CA: 2013 1 0 Wonderfu l Fruit 0. 181 0 ND , ND ND,ND ND , ND <0.03. < 0.03 ( 1 3-CA03) [< 0.01] [ <0
. 0 1 ] [<0.01] [< 0.03] Davis , CA : 2013 1 0 Wonderful Fruit 0. 182 0 ND.ND ND
. ND ND.ND < 0.03. < 0.03 ( 1 3-CA04) [< 0.0 I] [<0.0 1 ] [< 0.01] [ < 0.03] Yuba City. CA; 10 Wonderful Fruit 0. 1 78 0 ND.ND ND.ND ND.ND < 0.03. < 0.03 2013 ( 1 3-CAOS) [ <0.01] [<0.01] [< 0.01] [< 0.03] 1 A 70 % WG formulation of sa flufenacil (BAS 800 0 1 H) was used. 2 ND = not detected (< LOO). The LOO was 0.002 ppm. and the LOQ was 0.0 I ppm for each analyte. Per-trial averages were calcu l ated by the petitioner and assumed LOQ resid ues for samples < LOQ. 3 Re s idues of M800H 11 and M800H35 were not converted to parent equivalents because they were < LOQ. J Combined residues of saflufenaci l , M800H I I , and M800H35 (metabolites are not expressed in parent equivalents).

T ab le B .7 .6.1.1- 7
. S u mmary of R es idu es from P omeg r a n a te F ie l d T ri a l s with Sa fluf e n ac il. Total Residues (ppm) Application Rate PH L Crop Matrix Analyte ( l b ai / A) (days) n' Min. 2 Max. 2 LAFT3 HAFT3 Median 3 Mean 3 SD 3 Pomeg ranate Safl u fenaci I 0.177-0.182 0 4 <0.01 <0.0 1 < 0.01 <0.01 0.0 1 0.01 NIA M800H I I 4 <0.01 < 0.0 1 < 0.01 < 0.01 0.0 1 0.0 1 NIA M800H35 4 <0.01 < 0
. 0 1 <0.01 < 0.01 0.01 0.01 N IA Combined Re s idue s 4 4 <0.03 < 0.03 <0.03 < 0.03 0.03 0.03 NIA 1 n = numb er of field trials. 2 Values based on total numb er of samples
. 3 Values based on per- tr i al averages . LAFT = lowest average field trial. HAFT = highest average fie l d trial. SD = s tandard deviation. For computation of the LAFT, HAFT, median , mean , and standard deviation, values < LOQ arc assumed to be at the LOQ (0.0 I ppm). NIA = not applicable. 4 Combined re s idues of s atlufenaeil, MSOO H 11 , and M800H35.
Pa e 6 of7 MRlD # 4943420 ISaOufenacil/PC Code I 18203 / lnt erregional Research Project No. 4 

### Ill. CONCLUSIONS The submi tted pom egranate fie ld trial data are adequate. Following four banded ground applications of the 70% WG formu lation of sa flufenacil at a tota l seasona l rate of 0 .177-0.1 82 lb ai / A , combined re s idu es (and per-trial averages) of saflufenacil , M800H 

### 11, and M800H35 were below the LOQ ( < 0.03 ppm ) inion all samples of pomegranate harv ested at a 0-day PHI. Residue decline was not investigated. Residues of M800Hl 1 and M800H35 were not converted to parent equ i valents because they were < LOQ. An acceptable method was used for residue quantitation , and adequate storage s tabili ty data are avai labl e to support sample storage durations and conditions for a ll ana lytes. 

### REFERENCES DP# 349938, 7/ 22/ 09 , G. Kramer.

Pa ne 7 of7 MRJ D # 4943420 I