Pyra cl ostrobin Human Hea lth Ri sk Asse ssment DP# : 37 8282



### U NITED STATES ENV IRONME NTAL PRO TECTION AGENCY WASHINGTON , D.C
. 20460
OF FICE O F C H [ MICAL SAnTI ' A:" D P OLLl 'TI O " PR[\,}:NT IO:"

M EMORANDUM Date : 5 /27/10 S U BJECT : Pyraclostrobi n. Human Health Ri sk A ssessment fo r th e Decre ase i n Ap plicat ion Volume and Increase in Soybean Forage and Hay T o lerance s . P C Code: 099100 D ecision No .: 4 16999 Pe tit io n Nos .: 9F7569 Ri sk Asse s smen t Ty pe: N/A TXR No.: N /A MR lD No .: 4 7774701 -02 D P B arc ode: 37 8282 Re gistrati on No. : 7969-186 , 7969 -28 9 Reg ulat ory Act ion: Sec tion 3 Regi stra tion Ca se N o . : N/A CAS No .: 17 5013-18-0 4 0 C FR: 1 8 0
. 58 2 V er.Apr.08 F ROM : W
. Cutchin , A cting Senior Branch S cie ntist
. \.:..- Il 

# t' J", { (i f , 

# l-: ,J Alternative Ri sk Integrati on and A sses sment ( ARIA) Team Ri sk I ntegratio n, Minor U se and E mergency Re spon se Branch ( RIMUERB) Re gi stration Div ision ( RD; 750 5P ) T H ROUGH : P. Deschamp, B ranch C hief Ri sk As sess ment B ranch 

### III (RAB 

### I He alth Effec t s Div ision (H ED; 

### 75 9 TO : 

### T
. Ki shiS
. Hill , 

### RM # 22 '/ Fungicide Branch RD 

### (7 505P) ARIAIRIM UERB o f RD o f the Office o f Pe sticide Program s (O PP) i s charged with e stimatin g the ri sk t o human health from expo sure to pe sticides
. RD o f O PP has reque s ted th at ARIA evalua te h azard and expo sure data and co nduct die tary, occupational , re sident ial and aggregate expo sure a ssessme nts, as n eeded, to e st imate the ri sk to h uman health tha t 

### w ill re sult fro m pr opo sed an d c urrently regi s tered use s of the act ive ingredient pyraclostrobin
. Th e ove ra ll ri sk ass essment, di etary ri sk ass es s ment, and re sidu e c hemistry a ssess ment we re prov ided b y W
. Cutc hin.

Page I o f 3Pyr aclo strobin H uman H ealth R i sk A ssessment D P# : 378 282 This d ocument will o nly ad dres s th e differen ces in th e h uman he alth ri sk ass essment f rom th e last as sess ment. The re mainder o f the o riginal ass ess m ent rem ain s un changed (P P# 9F 7 528 , OP Num. : 362855 , W
. C u tch in , 1 111 8 /

09 ). 

### Executive S umm ary B ASF requests the i ncrease in tol erance s for th e c ombi ned re sidu e s of th e fun gicide pyraclo stro bin (c arbamic acid, [ 2 -[[[ I -(4-chloro phenyl) -1 H- py raz ol

- Syl]oxyJmethyl]phenyl]methoxy-, m ethyl e ster) an d it s desmethoxy m etabolite ( me thyl

-N

- [[[I-(4

- c h lo rophenyl)pyraz o l-3

- yl] oxy ]-0 -tolyl] c arbamate ) , ex pres s ed as parent co mpound, inio n the fo llowing c ommoditie s : Soybean, f o ra ge 1 1 .0 ppm Soybean , h ay 1 4 .0 ppm Co ncurrently, BASF wis he s to am end the re gistration o f Headline ® Fungicide (E PA Reg
. No
. 7969

- 186) an d H cad line ® S C Fungicide (E PA R eg . No
. 7 969

- 1289) to permit ae rial application at s pray vo lumes down to 1 ga llon per acr e (G PA)
. B oth He adline ® , an EC fo nn ulation., an d H eadline ® SC
. a so l ub le co ncentrate f ormulation , co ntain 2 3
. 6 % a i ( 2 .09 I b ai/g al ) of pyraclo s trobin
. Th e p roposed u se i s two a pplication s at th e maximum seaso nal rate of 0
. 2 Ib ai/A. The application may be made u s ing ground or aeria l equipm ent. The propo sed pr eharvest interval s ( PH I) range to the begi nning o f fl owering s tage ( 25%) at 2 1 days
. Die tary ( Food & Dr inking Water ) Exposure A sses sment A RIA has determ ined th at the residue c hemi stry d ataba se i s adequa te to s uppo rt the propo sed c hange in u se p attern an d in creases in the s o ybean f orage an d h ay to lerance s. Soybean f orage and ha y are not hum an foo d it ems, and the i ncrease s in hay and forage tolerance s do not require a n increase in exi sting meat, milk
. poultry and e gg tolerances (PP # 9 F7590, OP N um. : 37 1 252, 

## w . C utc h in, 5/26/l0)
. Envi ronmenta l Fate and Effects D ivi sion's (EFED) pre v iou s dr i nking water as sessmen t w as b ased o n th e exi st in g re g i stered u se of aerial ap pli cation o n turf and ornamentals repre senting the h ighest applicati on rate a t 0 .5 I b s a i /a cre with 6 m aximum s easonal appl ica tio ns at 1 4 d ay interval s. EFEO be li eved th at the aeria l u se o f pyraclostrobin o n turf an d ornamentals w ould po se th e upper -b ound c oncentration s in s urf ac e an d ground wa te r s i nce s pray d rift i ncreases an d app lication e fficiency d ecreases in an aeri al applica ti o n techn ique ( DP N um : 362852 , R
. M iller ; 10 114 /09)
. The refore , the propo sed u s c o n soybean s w il l no t re sult i o a h igher exposure to pyraclo s trobin in drinkin g wa ter . S ince there i s n o in crease in d ietary ( food 

### + dri nking w at er) exposure to pyraclos trobin, a re as se ssm ent of the l ast dietary ri sk analysis ( PP# 9F7528, DP Num
. : 3 69379, W
. C utchin , 10 /3 0 /

09) is no t required
. R es ide ntial Expo sure N o new res idential use s of p p-ac1 o strob in are proposed i n thi s petition
. A p roduct con taining pyraclostrobi n (i.e ., In s i gnia ) i s re gis tered f or application to re sid entia l tur f gra ss and recreational s ites and w as included in th e l ast human health ri sk asse ss ment.
Pa g e2 0f 3Pyrac1ostJob in Aggregat e R isk Human H ealth Ri sk A ssessment DP # ; 37 8282

In acc o rdance with the F QPA. A RIA mu st c on sider and aggre gate ( add) pe sticide expo sure s and ri sks from three ma jor so urces : food
. drinki ng wa ter, and re s idential expo sure s . S ince the re are no change s i n the expec ted expo sure s fro m the three m ajor so urces , the re is n o chan ge in the h uman hea lth ris k asse ssment for c hildren and adul t s, wh i c h w as fou nd no t to reach a l evel of co ncern to the Age ncy (PP# 9 F7528, DP N um . : 362855 , W
. C utchin, 1 1/18/ 09)
. Oc cupa tional Exposure The p revi ous oc cupatio n al ri sk ass essm ent con sidered expo sure to work er s from ground and a erial f oliar applications o f pyraclo strobin u sing m ore app lications and at a higher tota l application rate than the pro posed use s. O ccupational pesticide handlers m ay experien ce s hortand intermedi ate -term e xposure to pyracl ostr obin
. The e xpo sure f or mixer /l oaders w orkers w as determined as the wor st-case sc enario. Derm a l e xposure ri sks were determined to n ot be of concern to the A gency provided m ixe r /l oade rs u s e pro tective g lo ves as s pec i fied on the product label. Inh alation exp osure ri sks we re al so de te rmined to n ot be o f c o n ce rn to th e Agency if m ixer / lo a der s s upport appro xi mately 600 a c res treated pe r day o r i f they u s e a du st/ mist filte ring r e sp irator wh ile s upporting ae rial application s of 1 200 A treated/day
. It i s a l so po ss ible fo r agri cultural wo rkers to h ave p os t-applicatio n expo s ure t o p e s ticide re sidu e s d uring the c o u rse of typical agr icultura l activi tie s . T he mos t c on servative estimate ( i
. e., highe st exp osure /ri sk) of po s t-applicatio n expo sure re sulted i n expo sure ri s ks th at did n o t exceed th e A gency ' s level of c o ncern ( DP N um: 36692 7, M
. D ow , 7/23 /09)
. S ince the pr evious oc cupational ri sk as sessment w as condu cted with a total ap plicatio n rate higher than the proposed use s o n so ybeans and expo sure ri sk s did n ot exceed th e Age nc y's level o f concern , the oc cupational ri sk from the propo sed use s wi ll al so n ot exceed th e Age nc y's level o f concern . Recommendation T here are no human h ealth co n side ration s th a t wou ld p reclude g ranting th e re que sted u ses of pyraclo strob in o n s oybean
. AR IA recommend s for increase s in the fo llowing tole rance s: S oybean, f orage II ppm S oybean, ha y 14 ppm No te to PM : It is recommend ed that the tolerance expre ssion f or 40 C FR 

### § 18 0.474(aXI ) be c hanged to : " To lerance s are e stab li shed for re s idue s o f th e fun gicide pyraclo strobin , i ncluding i t s metabo lite s and degradat es, i n or on the c ommodit ies in the t able below
. C o m p l iance with the tolerance level s s pecified below i s to b e determined by mea s uring o n ly the sum of pyraclo strobin (c arbamic acid, [ 2-[[[ 1- ( 4- chl o rophenyl) -1 H -pyrazo l- 3 -yl]oxy ] methyl]phenyl]methox y-, m ethyl e ste r) and it s desmethoxy met abolite ( methy l-N-[[[ I-(4 -ch loropheny1)- lH -pyrazo l-3- yl ]oxy]methyl]phenylcarbamate) , calcu lated a s the s toichiometr i c equiva lent o f pyraclostr obin, in or o n th e comm od ity ."

Pa ge 3 of3Pyraclo strobin Summary of A na lytical Chem i stry and R esidue Data D P #: 37 125 2


### UNITED STAT ES ENVIR ONMENTAL PROTECTION AGENCY WASHINGTON , D .C. 20460 o rnce O F O!UII CAL SAFETl · A:'IiD POLL L'T10S P RE\"E :\TlO:'li



### TO: F ROM: P C Code : 099100 Inc ision No .: 41 6999 Pe tition No s . : 9F 7590 R isk Ass essment Type: N / A TX R No .: N / A Y1 RID No
. : 4777 470 1.{}2 MEM ORANDUM Date : 5 /26/ 10 SUB JE CT: Py raclostrobin: Pet ition for the Dec rease in A pplication Vo l ume and I ncrea s e in Soybean Forage and Ha y To lerances
. S ummary o f An alytical Che mistry and Res idue Data
. D P Ba rcode: 37125 2 Re g istrati on !II o.: 7 969 .\ 86 , 7 969·289 Re gulat ory A ction: Sect ion 3 Regi strati on Case :"'"0.: N / A CAS No
. : 1 75013 -18 -0 40 e FR: 1 8 0 .582 

## / "i:-L ' VeT.Apr
. 08
, -' 1. ( / ' : 1

4

- -**'lc** W
. Cutc hin
. Act ing Se nior B ranch Scienti st /
. -(- tL-
..... . A lternative R isk Integration and A ssess ment (A RIA ) Team Ri sk Integration, M inor Use an d Emergency Response B ranch (RIMUE RB) Reg i s tration D ivision ( RD ; 7505P) T H ROU GH: L Che ng, Ph
. D,. Se nior C hemis t 

# (J1l f)fJ t -**~f-** Ri sk A s s essment Branch III ( RABII 

# {Yt4 Health Effec ts Divi sion ( HED; 75 09 T
. Kishf S
. Hi ll. RM # 2 2 / F ungicide Branch RD (7505P)
A ction R equested The registrant n otified the Agency that over -tolerance re sidues h ave been f ound in so ybean forage an d hay samp les while generating bridgi ng data at 3 l ocation s ( in a 2008 s tudy) to s uppo rt reducing the app lication s pray vo lume
. 

### Exec utive S u mmary BASF requests th e increase in tolerances for the co mbined residue s of the f ungicide P age I of27Pyr aclo strobin S um mary o f Ana lytical C hem is try an d R esidue Data DP# : 37 1252 pyraclostrobin (car bamic a cid, [2-[[[1- ( 4-chl oroph en yl)-IH- pyr azol-3- yl]oxy]methyl]phenyl]methoxy- , methyl es ter) and it s d esmethoxy m etabolite ( methyl-N-[[[I-(4- chl orophenyl)pyrazol-3-yl]oxy]-0-tolyl] carbamate ), expr essed as par ent co mpound , ini on the foll owing co mmodities: S oybean , f orage II .O ppm Soy bean, hay 14 .0 ppm C oncurrently, BASF wi shes to amend t he r egistration o f H eadline ® Fun gicide ( EPA Reg . No. 7 969-186) and H eadline® SC Fungicide ( EPA Reg. No
. 79 69-1289) t o p ermit aerial application at s pray vo lumes down to 1 gallon p er ac re (GPA). B oth Headline ®, an EC f ormulati on, an d H eadline® SC , a so luble co ncentrate f ormulation , c ontain 2 3 .6 % a i (2. 09 lb ai/ga l) of p yraclo strob in
. The pr oposed u se i s tw o a pplication at th e maximum s easonal r ate o f 0 .2 lb ai/ A. The appli c ation m ay be mad e u sing ground o r ae rial eq uipment. T he p roposed preharv est interval s ( PHI) ran ge to th e be ginning o f flowering s tage (2 5%). The ove r-tolerance r esidue s had b een d iscussed in a C hemSAC meet ing. Re sidue data in soy bean f orage an d hay s howed co mparable re sidues o f par ent and its m etabolite w hen th e fung icide ( BAS 5 00 0 0 F F ungicide) w as a pplied, at th e label rat e, in s prays applied at 2 0 g allons per ac re (G PA), 2 G PA , or 1 G PA u sing a gr ound application device
. Acc ording to th e re gistrant, th e trial param eters u sed i n these brid ging s tudies we re s imilar to tho se co nducted to o btain the ori ginal regis tration on soybean (i n a 20 02 s tudy)
. C hemSAC (5 / 13/ 09) n oted th at the form ulation ( 20% BAS 5 00 F WG) u s ed in th e o riginal field trial s a lso co ntained ano ther active i ng re dient th at m ay r aise re sidue c onc entrati ons o f pyraclostrobin, as we ll a s a " non-silicone s pray ad ju vant," at an un specified co ncentration
. T he 20 08 trial s w ere d escribed as c ontaini ng 0
. 5 ptiA o fa c rop o il co ncentrate . C hemSAC determin ed th at p rovided th at ther e are i nsignificant differ ences in the type o f a djuvants u sed, and i n the c oncentrations o f th ese a djuvants in the s prays , b etween th e 2 002 and 2008 s tudy, no fi eld t rials in a ddition to th e 3 brid ging s tudies are n eeded. Th e SAC al so co ncluded that n ew soy bean f orage and h ay data can b e c ombined w ith th e o riginal data to d erive new tolerance s f or the se 2 s oybean co mmodities ; w hile th e n ew see d d ata do n ot s upport an incr ease in th e seed to lerance
. T he SAC a lso re commended that th e re gi strant pro vide a dditional information t o s upp o rt th e ass umption that the a djuvant i s not affec ting th ese result s. The SAC furth er c oncluded tha t the s pray vo lume b y gr ound applications i s not a fa ctor th at affects r esidue l evels i n s oyb ean seed, f orage , an d h ay . Pyracl ostrobin [c arbam ic aci d , [2-[[[1-(1-( 4- chlorophenyl )-IH-p yrazol- 3- yl] o xy] methyl] ph enyl] m ethoxy- , meth yl es ter] bel ongs to th e s trobilurin cl ass of fun gicides. S trobilurins are syn thetic an alogs o f a natural ant ifungal s ubstance wh ich inhibit s s p o re germination, m ycelial growth, and s porulation o f th e fung i c ausing di seases s uch as f ruit rot i n s trawberry , earl y leaf rot in peanut s, lat e b light in p estachios, ru st di s eases in soy bean s, pr e- and p ost fruit rot o f pom e and s tone fruit s . Th e fun gicide is curr ently registered to BASF Co rporation (B ASF) for u se on a v ariety o f field , vegetable, fru it, and n ut crop s. It i s f ormul ated as w ater-dispersible granule s ( WDG) or an e mulsifiable co ncentrate (EC) and i s typi cally appl ied as f oliar appli cations u sing gro und o r aer ial e quipment at maximum se asonal r ates of 0 .3-3.0 lb ailA. T he 2 0% WDG f ormulation is al so re gistered f or u se as a see d treatment o n s ome cr ops. P age 2 o f27Pyr aclostrobin S ummary o f Anal ytical Che mistry an d Re s idue D ata DP#: 37 1252
Pyracl o strobin t o leran ce s h ave been estab li shed in 4 0 C FR § 1 80
. 582
. To leran ces f or p lant c omm oditie s ar e li sted in 4 0 C FR § 180 .582 ( a) ( I) and ar e ex p resse d in t e rms o f the c omb ined re sidue s of th e fungi cide pyr aclo strobin ( car bam ic ac id, [2 -[[[ 1- (4 -chl orophenyl ) -IH

- pyrazol

- S
. yl] oxy ]methyl]phenyl]methoxy - , methy l e ster) and its de smethoxy metabolit e (methyl N -[[ [1 -(4- chl oroph enyl) -IH -p yrazol- 3-yl]ox y]methyl]phen yl carb ama te), e xpre s sed as parent c ompound
. Th e e stabli shed t oler ance s fo r plant comm odities ran ge fro m 0 .02 p pm in/o n w heat grain t o 29 ppm i n/on l eafy v egetable s. ex cept 

### Bras sica
. T oleran ce s fo r l ive st ock co mmodi ties ar e li sted i n 4 0 CF R § 1 80 .5 82 ( a)(2) an d are ex pressed i n term s of the co mbine d residues of the fun gi cide p yraclo strobin an d its met a boli tes c onvertibl e to 1 -( 4 -chlo rophenyl ) - lH

- pyrazol

- 3-o1and 1

- ( 4-c hloro-2- hydro xyphenyl)- 1 H-p yraz ol- 3-0 1, e xpressed as p arent co mpo und
. Th e e stabl i shed t oleran ces for li vestock co mmodi ties rang e from 0
. 1 t o 1
. 5 p pm ; n o t olerance s are e stabli she d f or po ultry c o mmoditi es . The H ED M etabo li s m A sses sment Re vi ew Co mmi ttee ( MA RC) me mo h as d et ermined that f or purpo ses of t oler ance an d d ietary ri sk ass ess ments. t he re sidu es of co ncern in plant and rotati onal c rop co mm odities include pyra clos trob in and metabolit e B F 500

- 3
. The re sidues o f co ncern i n li vestock co mmodi ties in clude pyraclo strobin an d it s m eta bolit es co nvertible to 1

- (4

- c hlorophe nylj- l H-pyrazo l-j- ol ( BF 500-5 ) and 1 -( 4-chl o r o- 2

- h y dr ox yphen y l ) - IH-pyr az ol- 3

- 01 ( BF 5 00 -8 )
. There ar e a dequate re sidue ana lytical me th ods f or to leran ce enf orcem ent . The an a lyti ca l method s fo r plant c ommodi tie s are l iquid chromatogr aphy with tan dem m ass s pectroscopy l m ass spe ctro scopy dete ctor ( LCIMSIMS) and high pre ssure liquid chr omato graphy with ultravio let de tecto r ( HPLC IU V), which both measure pyracl o strobin and i t s de smethox y metabo lite
. The analytical meth ods fo r live stock commodi tie s, g as chrom at ography with ma ss s pectroscopy detector (GCIM S) and 

### L C /MSIMS, convert pyraclo strobin and re lated metabo lite s to chloro pheny lpyrazo lol ( BF 500 -5) and h ydroxylated chl orop heny lpyrazol ol ( BF 500 -8) i n goat s and c h loropheny lpyrazo lol (BF 50 0-5) and h ydroxylated c hloro ph eny lpyrazo lol (BF 5 00-9) in p ou ltry
. HED concluded that th e s e methods are s u itab le a s e nforcement methods
. Sample s o fr aw agricultural and processed commoditie s fr om the current petiti on s were analyzed f or pyrac lostr obin re sidue s o f concern u sing an adequate L CIMSIMS meth od (BASF Method D 9908, v e r . II), which is s imilar t o the prop osed enf orcement meth od
. The meth od was ad equate ly va lidated i n c onjunction with the field trial anal yses . T ota l re sidues o f pyraclostrob i n and B F 5 00·3 are expre ssed as pyraclostrob in equi va lents
. Fo r ea c h analyte, the v alidated m ethod li mit o f quantitati on ( LOQ) is 0 .02 ppm . The meth od i s a dequate f or data c o ll ect ion. The requirem ents fo r mult iresidue m e thods te stin g data ar e fu lfilled
. Pyraclostrobin w as s ucc essfu lly ev aluated t hrough s everal o f th e FDA prot ocols (co mple te r eco very through p rotocols D an d E), whil e recovery of metaboli te BF 5 00 -3 w as un succes s ful i n al l protoc ols
. There are ad equate s torage stability da ta fr om pre viou s p yra clostrobi n petitions. There are n o co rrec tion s whi ch ne ed t o be a pplied si nce p yraclostrobin re sidues of conc ern w ere fo und to be reaso nably s ta ble o v e r a wid e rang e of co mmodi tie s un der froze n s torage co n ditio ns fo r 1 9-25 Page 3 of27Pyraclo strobin Summary of Analytica l Chemistry and Re sidue Data DP #; 3 71252 months
. The se data may be translated in the current petition to validate sample storage condition s and duration s. Adequate cattle and poultry feeding studies are a vailable to support the livestock dietary burden s resulting from the proposed uses . The onl y so ybean commoditie s which will have higher tolerance s than those u sed in the last e stimate of livestock diet s are soybean forage and hay. Since s oybean forage and hay are considered feed stuff s only for dairy cattle , there are no change s in the previou s di ets for b eef cattl e, poultry and swine, and therefore no changes in the as sociated live stock tolerances are required
. The current pyraclo strobin tolerances for livestock commoditie s wer e e stablished based on re sults from the dairy cattle feeding s tudy and the Agency 's previou sly e stimated dietary burden s for pyraclostrobin re sidues. Ba sed on the updated dairy cattle dietary expo sure level s and the residue data from the dairy cattle feeding s tudy, the exi sting pyraclostrobin tol erance for milk at 0.1 ppm i s adequate and will not need to be changed as a re sult of the proposed use s in thi s petition
. The petitioner ha s pro vided adequat e bridgin g residue data reflecting the maximum proposed us e pattern ofpyraclostrobin inion s oybean forage and ha y. The combined residue s ofpyraclo strobin and it s metabolite BF 5 00-3 did not exceed the propo sed tolerance lev els of 11 .0 ppm and 14.0 inion s oybean forage and hay, re spectively
. Re sidue data in s oybean forage and hay s howed comparable residues o f parent and its metabolite w hen the fungicide wa s applied , at the label

. rate , in s prays applied at 20 , 2 , or I GPA u sing a ground application device. S amples were

anal yzed u sing an adequat e analytical method, and are s upported by the available s torage s tability data
. The number and location s offield trial s are in accordance with O PPI S G uideline 860.1500 , ChemSAC recomm endations, and the conducted field trial s reflect the maximum proposed foliar use patt ern. The field trial data for all s oybean forage and hay reflecting the proposed application rate w ere analyzed and the re sults s upport the propo sed tolerance s for s oybean forag e and hay. The adju vant data indicate that mo stly paraffin and fatty oil s were used in the s ubmitted s tudies for which adjuvant data are available. The studie s which did not li st a s pecific adjuvant had residue data for pyraclostrobin which were essentially id entical to the other s tudies. ARIA has determined that there are insignificant differences in the effect s, ifnot type, of the adju vants us ed in the spray s, between the 2 002 and 20 08 s tudy; th erefore, th e no a dditional fi eld tri als are needed
. ARI A recommend s f or th e propo sed soybean forage and hay tolerances and the proposed use o f pyracl ostrobin. N o s oybean s eed residue data were collected at the label rate. Data obtained in thi s s tudy wer e at 2X the label rate indicated low levels ofpyrac1o strobin re sidues (LOQ- 0 .08 ppm) . No change in the s oybean s eed tolerance i s required from the proposed use . The re sults of the s ubmitted field trial data indicate that there i s no increas e requir ed on s oybean s eed. Based on the field trial data and the previou sly s ubmitted s oybean proce ssing study, tolerance s for s oybean m eal and refined oil are not required
. Analytical reference s tandards for pyraclo strobin and its regulated metabolite s are available at the E PA Na tional Pesticide Standards Repository
. Page 4 of 27Pyr aclostrobin Swnmary of An alytical Ch em i stry an d Residue D ata DP #; 37 1252 

### Regulatory Recommend ation s and Re sidue C hemistry Deficienci es To s uppo rt the ae rial use, BASF h as su bmitted p reli minary model genera ted deposit ion p rofile for a erial applica tion to c ompare with th e ground depo si ti on . H owever . detai led inp ut and output d ata fo r the m odel s i mu l ations as well as applicati on specificati ons ( i. e . nozzle s types, operating pressure an d boom he ight ) f or gro und e quipment were needed to verify the residue bridging data for a erial app lication ( DP # s 370130, 370133, R
. Mille r, F
. Kh an, 1 1 /1 8 /

09 )
. The resolution of th ese d eficiencies w ere m ade a co ndition of regi s tration fo r th e low vo lume application of pryra clostrobin to c om and wh eat ( DP Barc ode s: 36 8042, 36 8086, M
. Neg u ss ie , 1 1 11 0 /

09)
. Th e re so lut ion o f the se d eficiencies w ou ld al so a ffect the rec ommen dation s of the pre sent petit ion ; however , new data hav e b een s ubmitted b y the p etitioner and hav e b een e xamine d b y Environmental F ate and E ffects Di v isi on (EFE D) and f ound to be ad equate (e

- mail, 

### B. Ande rson, 5

/ 2 6110 ). ARIA recommend s f or regis tration for the r eque st ed uses o f pyracl o str obi n o n soy beans. Th ere are no re sidue c hemistry i ssues that wo uld preclud e g ranting regi strat i on f or th e re quested label c hange t o a llow ae rial applicat io n o f p yraclostrobin w ith sp ray vo lume as low as 1 G PA t o s oybeans and in creases in the followi ng toleran ce s : Soybean, fora g e 11 ppm So ybean, h ay 14 ppm Sinc e the re are no in crease s in any hum an food item o r increas e i n pyracl ostrobin application ra te. an u pdated h uman h ealth ri s k asses smen t is not required
. No te to PM : I t i s rec omm ended tha t th e tolerance ex pre ss ion fo r 4 0 C FR 

### § 180 .474(a)( I) be c h anges to : " Tolerances ar e e stablished f or re sidues o f the f ungicide pyr ad ostrobin, including its met abolites an d d egradates, in o r o n t he co mmodities in th e t able bel ow . Co mp li ance with th e tolerance level s s p eci fi e d be l ow i s to be d eterm in ed by me asur ing on ly th e s um o f p yracl o strobin ( carbamic a cid , [ 2-[[[ 1-( 4- chlor o phenyl )- 1H -pyrazo l-3-yl] oxy ]methyl]phe nyl]methox y- , me th yl e s ter) and it s de smethoxy metabo lit e ( methyl-N -[[[ I -( 4

- ch lorophenyl)

- 1H

pyrazo l-3-yl] oxy]meth yl]phen ylcarbam ate), c alculated as the s toichiometric eq uivalent ofpyraclostrobin, i n o r o n the comm odity
. " 

### Background Pyraclostrobi n belo ngs to th e s t robi luri n class of fungici des
. S trobi lurins are synthetic an alogs of a n atural an tifungal s ub s tance which inhibits s pore germi nation and m ycelial gro wth an d s po ru lation of the fungu s on the leaf s urface
. The chem ical s tructure and n omenclature of pyraclo strobin are pre sented i n Tabl e I
. The physic och emical p ropertie s of th e technical grade of p yraclostrobin are pre sented in Tab le 2
. 

# I T ABLE I. Te st Co mpound Nomenclature
.

Page 5 o f2 7Pyra clos trobi n S umm ary of Ana lyt ical Ch e m i s try and R esidue D ata DP #: 3 71252 TABL E 1
. Tes t C omn o u nd N om e n cla ture. Compoun d



### o '" 

# c

, --O-<:1 /Oy "--...OCH , H

,C 0 C ommon nam e P ac lostrobin**Co ~e** **ri mental**  name B AS 5 00 F IUP AC name methyl N - { 2-[ 1- ( 4

- chlorophenyl) -1 H

- pyrazol -3-ylo xymeth yljphenyl }(N-melhoxy) carbamate CAS name meth I 2

- I- a-chloro h en I -I H- azol -3

- I ox vlmet h 'H nh cn v l l me thoxv c arbama te C AS re i st numbe r 1750 13- 1 8

- 0 End

- use pr oducts (E P ) Headline® Fu ng ic ide , EP A Reg. N o. 79 69

- 186 ; H ea d li ne® SC Fungicide , E PA Reg. No
. 7 969

- 289

Prod uct C hemist ry data w e re revie wed by the Registration DI VISIon (D P # 2 698 4 8 and O P# 27 41 91, 5 / 3 / 0 I , 5 / 15 /01, an d 6n101 , S
. M alak )
. B A S F ' D ocument Number
. TAB LE 2
. P twSicoc he m ic al**Pr ~e** **rl** o f T ec h nica l Grad e Pv ractostro bin
. Param eter Value R eferences (M Rl m M

eltine point/ranee 6 3
. 7

_ 65.2 °C 45 11 82 13 p H N ot aoo licable O ensi 1 .367 a/e rn 4 511 82 14 W ater s olubili at 2 0"C 1. 9 ± 0 .17 m deionize d water . o H 5 .8 45 118 233 Solve nt so lubility n-he ptane : ( 0.37 gl IOOm L) ; 2- pro panol (3 .0 45 11 8228 gl IOOm L ) ; l

- octanol ( 2.42 gi l OOmL) ; o live oil ( 2.80 gl IOOmIL); methanol ( 10.0 8 gl IOO mL) ; > 5 0 gi l OO mL in acetone , et hyl acetate , acet on itrile, O C M and to lue ne . V, r ressu re 2 .6 x 10

- 10 h Pa at 20 °C 45 1182 14 D issociatio n c onstant, p K
. N one ( no di ssociable m oieties }**ctan ol** **:'~ ater**  parti tion coefficien t, 3 .990 mean log P , ... ; ( Po
... is 97 72) 45 118 2 15 L o "(Kow a t room t emperature U V I visib l e absorpt ion s pectrum Th e stru ctura l i dentity o f B AS 500 F was 1 996/10955 c onfirmed b y N M R and M S s pectra. UV mo lecular ex tincti o n (e [ I m or' cm · I ]) : 2.5x 10 4 at 2 05 nm ; 2. 4 x I 0 4 at 275 nm
. I


### 8 60.1200 D irections f or Use
T ABL E 3 . S u m ma r v o f Pro o se d/R es is t ered U se P a ll e rn s o f rec los rrobln
. Ap plic
. Ti min g, Form u latio n App lic
. M a x . M ax. PH I U s e D irect ion s and Lim i tat i o n s T yp e , a nd [ E PA Re g. Ra te N o . S ea so n al ( days )

E q u ip
. N o.) (lb a i/A) App l ic
. A pp lic
. p " R ate Se aso n ( Ib a vA) Soy bean B ro a dcast fo liar H eadline7 0 .10 -0
. 20 2 0.4 0 2 1 Mi n. appLv el. I GPA spray; Fungi c ide Grou nd or ae rial [ 7969 -18 6] Resistance manage ment Option B : T o H eadline 7 SC limit the potent ial f or de velopment o f Fung icide resistance, do not make more than two aeolication s of H e adline or othe r 

### Page 6 of 27Pyra clostrobin Summary of An alytical C hemistry and Residue Data DP #: 37 1252 TABLE 3. Summarv of Prooosed'Rem stered Use Patterns of Pvraclostrobin. A pplic
. T iming, Fo rmulation A pplic
. M ax . Ma x . PHI Use Dir ections and Limit ations Type , and [E PA Reg . Ra te No. S easona l ( days)

Eq uip
. N o . ] (lb ai/ A) App lic
. Applic
. pe< R ate S eason 

## I II b ai/A\ [7969 -289J strobilur in fun gicide pe r seaso n. App licatio ns may begin pr ior to disease deve lopment and c ontinue on a 7

- t o 14

- day interva l. 

### Co nclusion. The s ubmitted u se dire ctions are s ufficie n t to allow evaluation o f th e avail able residue d ata relativ e to the proposed u sc. 8 60.1300 Na ture of the Residue
. Plants H ED MAR C , DP # 27 8044, L. Che ng, 10 /

9 1

0 I PP #OF6139 , DP # 269668 , L. C heng, 1 112 8/ 01 The nature of the residue in plant s i s adequat ely under stood ba sed o n acceptab le metaboli sm s tudies c onduct ed o n grape, potato, and wheat. The me taboli sm of pyracl ostrobin i s s imilar in the three c rops investigated. Pyraclo strobin and it s desmethoxy metab olite (B F 500

- 3) are the ma jor re sidues in crop matri ces includi ng l ivestock feed s; trypt ophan w as found to be the major residue in potato tuber and w h eat grain wh en c arbon- 14 wa s introduced in the tolyl ring (via the s hikimic acid pathway). The major de gradation r eactions are the remov al o ft he rnethox y group from th e carbamate nitrogen and breakage o f the e th er bond
. Th e HED MARC h a s determined that for th e tol erance and ri sk a ssessment, the termina l r esidues o f concern in plant s co nsist of pyraclo strobin and it s meta bolite BF 500

- 3. 860 .1300 Na ture of t he Res i du e - Li vestock H ED MA RC, DP # 27 8044 , L . Che ng, 10 /9

/01 PP # OF6139, DP # 2 69668, L. C heng , 1 1 128 /0 1 The nature o f the re sidue in liv estock is adequatel y u nder stood bas ed on acceptable rum inant and pou ltry metaboli sm s tudies. In 

### g oat, the major residues ar e pyraclo strobin and BF 5 00 -3 in mu scle and fat ; pyracl ostrobin, BF 5 00-3, and B F 5 00

- 5 and it s s ulfate co njugate i n mi lk ; pyraclo strobin, B F 50 0

- 3 , and BF 500 -5 and it s s u lf ate c onjugate , and hydr oxy lat ed de smethoxy m etabolite ( 500M67) in kidn ey; and metabolite s hydro ly zed to B F 50 0

- 5 and it s h ydroxylated c ompound (BF 500-8) in l iv e r. In 

### pou ltry, th e ma jor re sidues are pyracl o strobin and B F 5 00

- 3 in egg s; pyraclostrobio , B F 5 00-3, and h y droxylated B F 500- 3 ( 500M64) in fat ; and the g lucuronic acid c onjugate of hydroxylated BF 5 00-3 (500M 32) in liver . Radioactive residues w ere below detection in mu scle. The main degradati on reactions in li vestock c onsist o f demeth oxy lation , hydroxylation, and c onjugati on, and bre aking o f the ether bond
. Th e HED MARC h as determined that for th e tolerance and ri sk ass essmen t, the residues o f co ncern in livestock commodi ties c onsist o f pyraclostrob in an d it s m et abolites co nvertib le to 1

- (4

-chlorophenyl)

- lH

- pyrazol-3 -01 (BF 5 00-5) and 1 -(4 -chloro-2-hydroxyphenyl )-lH-pyrazol-3-0 1 Pag e 7 o f 27Pyr ac1 ostrobin ( BF 50 0-8). Sum mary of Analytica l Ch emistry and Res id ue Dat a DP #: 371252

860.1340 Residue Analytical Methods PP#OF6139 , DP # 269668 , L. Cheng , 1 1 /28/0 1 P P#O F6139 , D P# 269 850, L. Cheng, 11/ 8 /00 P lant Co mmodities E

nf

o rcement : T wo ad equate meth ods a re av ailable for en for cement purp oses fo r residues o f p yraclostrob in and the metabolite SF 5 00-3 in/on plan t co mmodities: an LCIMSIMS method ( BASF Method D 9908) an d an H PLCIUV meth od ( Method D 9904)
. Th e v alidated m ethod LOQ f or b oth p yraclostrobin an d S F 50 0-3 i s 0 .0 2 ppm in all tested plant matric es, f or a combin ed LOQ o f 0.04 ppm. A dequate ind ependent m ethod va lidation and radio validation data w ere s ubmitted for b oth methods an d f orward ed to AC SIBEAD for a petiti on me thod v alidation
. D ata Collection : Re sidues o f pyraclostrobin an d it s des methoxy meta bolite SF 5 00-3 in soy bean RACs w ere determined u sing S ASF Anal ytical Method 0 9908 ( version II ). Bri efly, residues were e xtracted by s haking wi th methan ol:water : 2N H CI (7 0:25:5; v :v: v); methanol:water (7 0:30, v:v) and c entrifuged. R esidues w ere th en p artitioned with c yclohexane and I N H CL saturated w ith NaCl, conc entrated to dryn ess, and re-dissolved in bu ffered me thanol :water (80 :20, v:v). The fin al chrom atographic an alysis o f re sidues w as determ ined b y L CIMSIMS. To tal residues of pyra clostrobin and SF 500- 3 are e xpre ssed a s p yraclostrobin e quivalents. Fo r e ach analyt e, th e v alidated method LOQ i s 0 .02 ppm . There we re acceptable co ncurrent method recovery data
. Livestock C ommoditi es Enforce ment: Two tolerance e nforcement method s w ere propo sed f or ruminant c ommodities : HP LCIUV method 4 39 /0 and M ethod 4 46, c onsisting of GCIMS m ethod 44 6/0 and LCIMSIMS m ethod 44 6/1. Th e HPL CIUV method d etermines re sidue s of pyracl o strobin p er se. Me thod 446 ha s a hydroly sis s t ep, and d etermines residues o f pyraclostrobin an d it s metabolites as S F 5 00-5 and BF 5 00-8. Th e va lidated m ethod L OQ s f or BF 5 00-5 typ e re sidues, in parent e quivalent s, are 0 .01 ppm f or m ilk and 0 .05 ppm for ti ssues, and the va lidated L OQ s fo r S F 5 00- 8 typ e re sidues , in parent equi valents , are 0 .01 ppm fo r milk , and 0 .05 ppm fo r ti ssues. Indep endent m ethod va lidation dat a for th e HP LC IU V and LCIMSIMS m ethods are acceptable
. Radiovalidation data s ubmitted for th e G CIM S and L CIMSIMS methods are a dequate for li ver and milk , and mar ginal f or mu scle. Method 44 6 h a s be en f orwarded to ACSIBEA D f or p etition method va lidation
. H ED co ncluded th at M ethod 446 i s s uitable as an e nf orcement meth od. Th e p etitioner had bee n requ ested to modi fy th e prop osed enf orcement method to includ e an y modification s made b y th e EP A lab oratory during th e Ag ency laboratory v alidation s hould the y be requested
. An e nforcement method f or poult ry wa s re viewed in PP #OF0 6139. Ho wever , tolerance s for p oultry egg and ti ssues h ave no t b een es tablished and are not required for th e purp ose o f th ese pe titions. Conclusi on. Th ere are ad equate residue anal ytical method s f or tolerance enfor cement and dat a co llection
. 860.1360 Multir es idue Me t hods
Page 8 o f 27Pyraclostro bin S umm ary of An al ytical C hem istry a nd Residue Data DP #: 371 252 PP #OF6 139, DP # 269668 , L. C heng, 1112 8 / 0 1 Pyraclostrobi n was succe ssfu lly eval uated through severa l of the FDA p rotocol s , wh ile recovery of BF 500 -3 was un successfu l in all protoco l s . Pyraclostrob in was c omple tely recovered thro ugh Pro tocol D ( in grape) and E ( in grape) , an d p artially recove red th rough Protocol F (in peanut)
. Metabo lite SF 500 -3 h ad poor peak. s hape and inadequa te s e ns it i v ity w ith Protoc ol C col umns , and th ere fore , was not further ana lyzed und er Protocol D
. E , and F
. The resu lt s of the multiresidue te sting for pyrac1ostrob in were forwarded to FDA on 1/4 /02 for t he purpo se of up dating the P esticide Ana lytical Manua l, Vo lume I (PAM I ). 860.1380 Storage Stability PP #OF6139, DP # 2 6966 8 , L. C heng , 11128 / 0 1 T he s torage interval from co llection to ext raction ranged fro m 131 -197 day s ( 4.3-6.5 mont hs) for s oybean RAC samp les i n th e s ubm itte d s tudy
. Adequate s torage stability data are availab le i ndicating t hat pyraclostrobin and metabo lite BF 500 -3 are reasonably sta ble at 5- 1 O °C in fortified s amples of grape juice (ju ice s), sugar beet tops (leafy vege tabl es), s ugar beet roots (root crop), to matoe s (fruit/fru iting vege table ), wheat grain (non -oily gra in), and wheat s traw (dry fee d) for up to 25 mo nths, an d in fort ified samp le s of p eanut n utmeat s (oi l seed) an d peanut o il for up to 19 month s. The storage interval s and co ndition s for sample s collected from the magni tude of th e residue and proce ssing s tu dies di scussed in this docume nt are p re sented b elow i n Table 4. TABLE 4
. S umm ary of Stor age Conditions and Intervals of Samples f rom C r o p Field Trials
. Matr ix MRID Stora ge Ac tua l S to r age Interval of Demon strat ed T empe r ature ( "'C) Duratio n (Mo nths ) Sto rage Stability (months) S weet/S our C h erry 47470201

- 10 5
. 7 19-2 5 Peach 4 .9 Plum 3 .8 S or sh um Foraae 47470 20 3

- 5 5 .3 1 9-25 S orghum G rain 8.2 So rzhum Sto ver 5 .3 C offee 4 747 0204 5- 20 4
. 1 19 -2 5 C offee ( Green be an , C leaned gr ee n b ean , Roa sted bean s, Dr ied 47470202 < - 5 < 1 m onth 1 9-2 5 spent gr ounds , Li quor extra ct , and In s tan t coffee )
. 

### Conclusion. T he storage co ndition s and durat ion s of samp le s are s upported by ade quate s torage s tab ility data availab le indicating that pyraclostrob in an d BF 500 -3 are stable i n frozen represe ntative p lant matrices for the d uration of t he s ubmitted s tudy
. 

### 860. 1400 Water , F ish, and Irrigated Crops Thi s guideline require ment i s not relevant to the c urrent pet ition s as th ere are no aquatic use s Page 90f27Pyra clostrob in S ummary of Analytica l Chemi stry and Re sidue Dat a DP# : 37 1252 b eing propo sed for pyraclo strobin
. 860 .1 460 F ood Ha nd li ng Thi s g uideline requireme nt is not relevan t to the current petition s as ther e are no f ood-handling u se s b eing propo sed for pyraclo strobin
. 8 60.1480 Meat, M ilk, P o ultry, a nd Eggs PP# s 8 F7385, 8F7390 , and 8E7 394 , DP# 35 9 194, M
. Ne gus sie, 4/02/ 09 Li vestock dietarY burden s The poten tial for tran sf er ofpyraclostrobin re sidues o f concern to me at, milk , poultry , and e ggs e xists becau se the re are s everal li ve s to c k feedstuffs (e .g., s oybean forage , seed , and forage ) that are as sociated with th e propo sed u se in th e curr ent petition
. The on ly soy bean c ommodities whic h will ha ve h igher to lerance s than those u sed i n th e last e stimate of l ive s tock di ets are forag e and hay . Si nce s oybean hay and forag e are c onsidered feed stuff s on ly for dairy c att le (Revisions of Fe eds tuff s in Table I of OPPTS T est G uideline 860 .1000 and G uidance o n Co nstructing Maximum Reasonab ly Balanced D iets ( MRBD), 6/ 30/08), there are no changes in the pre vious d i ets for beef c attle , poultry and sw ine, and th erefore no c hange s in the ass ociated li ve s tock tolerance s f or tho se commoditi es are required
. Th e reque sted chan ge in to lerance level s for s oybean h ay and forag e o n ly a ffect th e di et for d airy cattle
. The live stock dietary burd ens of pyraclo strobin are pre sented in Tab l e 5 , and reflect the mo st re cent guidance from HED c oncern ing re visio n s of feed stuff p ercentage s in O PPTS 860 .1000 Table I and c onstruction MRBD s. T he last MRBD o fpyraclostro bin w as c alcul ated b ased on th e a ddition of so rghum grain , s orghum forage , and s org h um s tover r esulted in a dietary burden e stima ted at 9.5 ppm for dairy c att le
. Replacing tho se so rghum item s with the s imilar s oybean c ommodities, re su lt s in an e stimated MRBD of 13 .7 ppm. The current pyraclo strobin to leran ces for live stock c ommoditie s w ere e stablished b ased on r esults from the dai ry c att le feeding s tudy and the A gen cy's e stima ted dietary burde n s f or pyraclos trobin re sidues, wh ich wer e orig iua lly calcu lated t o b e 3 5.4 ppm for dairy cattl e (PP # s 8F7 385, 8F 7390, and 8E7 394, DP # 3 59 1 94 , M
. Neg ussie, 4/0 2/0 9).

All data are based on Table 1 Feedstuffs (June 2008). a revision of f eedstuffs data f ou nd In Table 1(180.1000 OPPTS Tes t GUide lines)
. Residue TA BLE 5
. Ca lculation of M axim um R easonably B alanced D ietar y B urdens ( MR BDs) of P y ra clostrobin R esid ues fo r Li vestock. I F

eedstuff Typ e % 01)' % D iet To lerance (p pm) D ietary C ontribution M atter ( ppm) D airy C att le R 45%, CC 45% , P C 10 % L egume, hay ( cowpea) R 30 5 25 4
. 16 Barley, grain C C 88 20 0.4 0 .0 91 Co tton, undelinted s eed P C 90 10 0 .3 0 .033 Soyb ean , f orage R 35 20 1 1 6 .29 Soyb ean , h ay R 89 20 1 4 3.15 Sorghum , grai n, grai n CC 86 25 0
. 6 0. 15 TOTAL BURDEN 

# -- -- 10 0 -- 1 3.7 

## , Page 10 of27Pyr aclo s trob in Su mm ary o f A nalytical Ch emi stry an d Res idue Data DP #; 37 125 2 levels for bee f an d d airy are corr ected f or moistu re co ntent a nd are d etermined by fo rmula : tolerance I %D M x % in d iet. R: rou ghag e; CC: c arbohydrate co ncentrate; P C: p rotein co ncentrate. Typ ical co mpos itions of d ai ly ratio ns for t h e ani mals of c hoice f or T ab le I da ta follow: H igh vo lume m il k- producing lactating d airy cows hav e a d aily ration o f 45 % R, 4 04 5 % CC , an d 10 -15 % P c. Live stock feeding s tudies M AR C, PP # OF6 13 9 , DP # 2 7 8044 , L. C heng, 10 / 9

/01 PP #OF6139 , DP # 2 69668 , L
. Ch e ng, 1 1128 / 01 The HED M ARC di scu ssed the metaboli sm ofpyraclostrobin in livestock o n S eptember 20 , 2001 and has concluded that th e r e s idue s o f c oncern in liv estock co mmoditie s c onsist o f pyraclo str obin and it s me tabolites hydrolyzable t o BF 500-5 and BF 50 0-8 ( MARC, PP #OF6139, DP # 27 8044 , L. C h e n g, 10 / 9/01). Th e previou sl y s ubmitt e d dai ry cattl e f eeding data are adequate f or th e purpo s e o f e s tablishing tolerance s for pyraclo strobin re si due s. D airy cow s wer e orall y do sed twice daily f or 28 c onsecutive day s w ith pyrac1o strobin at dose le vels equi valent t o 8
. 8 ppm , 2 7.2 ppm ( mid do s e) , an d 89.6 ppm (high do se)
. The maximum co mbined re sidues o f pyraclostrobin and it s metabolites h ydrolyzable to BF 500-5 and B F 50 0-8 wer e < 0.0 2 -<0
. 02 3 5 ppm ( mid d os e) and < 0 .0 2-0.1 7 5 ppm (high do se) i n w hole milk, < 0 .0 2 ppm (mid do se) and 0 .03 93-0 .10 2 ppm (high dose) in s kim milk , and < 0.02-< 0. 05 6 1 ppm (mid d o se ) and 0 .131-0.2 58 ppm (high d ose) in milk fa t. Th ese data and the theoreti cal dietary burd en ofpyrac1o strobin for dairy c attle at 3 5.4 ppm at that time w ere u sed to e s tablish a tolerance o f 0 .1 ppm in milk ( PP #OF 6139 , D P# 2 69668, L. C heng, 11 /28/01)
. Conclusion. Th e o nly s oybean commoditi es w hich wi ll have hi gher tolerances th an tho se u sed in th e la st e s timate o fl ivestock diet s ar e f orage and h ay. S ince s oybean hay and forage are c onsidered fee d s tuffs o nly for dairy cattle , there ar e n o c hang es in th e pr evious di ets for bee f cattl e , poultry and s w ine, and th erefore no chang e s i n the ass ociated li vestock tol eran ce s are required . The c urrent pyracl o strob in tolerance s f or livestock co mmo ditie s w ere e s tabli s h e d b ased o n re sult s f rom the dairy c attle f eedin g s tudy and th e Age ncy' s es timated d ietary burd en s f or pyr aclo str obin re sidu e s , which were ori ginally c alculated t o be 3 5 .4 ppm for dai ry c attle
. B ased o n the upd ated dairy c attle dietary e xpo s ure l evel s and th e r e sidu e data f rom the dairy c attle f eeding s tudy , the ex is ting pyracl o strob in toleranc e for milk at 0 .1 ppm i s adequate and will n ot ne ed to be c hanged as a r esult o f th e propo sed u ses in th i s p etition
. 86 0 .1 500 C r o p F ield T r ial s The registrant h as s ub mitted data in the f orm o f 3 s ide-by- s ide residue fi eld tri al s on soybean forag e and ha y to s upport reduced s pray v olume s applications down to I G PA , whi ch will include aerial application s. The C h e m S A C p reviou sly re viewed prel iminary data fr om th e se s tudie s an d i ndicated that pro vided there are in signifi cant d iff erence s i n th e type o f adjuvant s use d and in the co ncentration s o f th e s e adjuvant s in th e s pray s, between the 2 002 and 2 008 s tudy, no additional fi eld trial s are needed
. Th e S AC a lso co ncluded th at ne w s oybean fora ge and ha y data can be combined wi th th e orig inal data to d erive n ew tolerance s f or f orage and hay, whil e includ ed s e e d data do not s upport an in crease in th e s oyb e an s ee d tol erance ( C hemSAC 5/ 13/ 09) , Pa ge II o f 27Pyr aclo strobin 

### Soybean Field Tri al s Su mm ary o f An alytical Che mistry an d R e sidue Da ta DP #: 3 7 1252

MRI D 4 7774 701 , M. N egussie, 3 / 16/10 

### BASF h as s ubmitted s upplemental field trial data f or pyraclo strobin (BAS 500 F ) on soybean. A total o f thr ee 

### soybean tria l s were co nducted in E PA R egion 5 (I L, 2 -tri als; lA , I-trial) durin g th e 20 08 gr owing s eason. A t each t es t lo cation , an untr eated plot (c ontrol) and three tr eated pl ot

s were establis hed . Th e treat ed plot s r eceiv ed tw o f oliar b ro adcas t a pplication s o f pyraclo strobin (2 lb ai / gal EC ( emul sifiable c oncentrate ); B ASF formulati on cod e, B AS 500 O OF ) at 0.1 9-0.21 lb 

### ai lA (0 .213

- 0 .2 35 kg ailh a) , with a 7 -8 d ay retreatment interval (RTI) , to taling a s e aso nal rate o f O.3 9-0Al lb 

### ai

/A ( 0.437-0.460 kg ailha). A pplications were initiat ed wh en th e soybean plants wer e a t th e be ginning of fl owerin g ( BBCH 6 0)
. A t o ne s ite (R050891) , t wo a dditional bro adcast 

### applic ations o f pyr acl o strobin were mad e t o the treated plot s at 0 .18-0 .21 lb ai /A ( 0.202 - 0 . 235 kg ailh a) w ith a 7 -day RTI , total ing in a s e a so na l rate ofO .80 -0 .811b 

### ai l A ( 0.90-0.91 kg a ilha). The 

### third appli cation at thi s s it e was made 42 day s afte r second appli cation at ad vanced pod filling gr owth s tag e ( BB CH 77) and th e f ourth applic ation wa s m ade at growth s tage B BCH 79 , 21 day s 

### prior t o harvest o f mature seed. E ach plot wa s tre ated using wa ter so l utions at eith er 1 9 -21 ga llA (O PA) , 2 O PA, and 1 O PA u sing ground equipment and includ e s the u se o f a c rop o il 

### concentrate ( COC ). Samples o f s oyb ean fora ge were harve sted a t be ginni ng p od de vel opment , 1 2-15 da ys after th e second applicati on (DASA ) and so ybean hay s amples were harve sted 20-21 O ASA and allowed to dry f or 5- 6 day s. Seed sample s we re harve sted a t ma turit y, 21 d ays after the l ast appli cation (OALA) ; only for th e tr eatm ent s with four ap plications. The r esidu es of p yraclo strobin a nd it s N -des metho xy metabol ite , 500M07 , pr evious ly designated B F 50 0-3 ) i n/on s oybean raw a gricultural c ommodity ( RAC ) s ampl es (f orage , hay, an d s ee d) 

### were quantitat ed using a LC /M S/MS method , BASF analyti cal meth od number 0 9908 (Version II)
. The val idated LO Q w as 0 .0 2 ppm f or e ach an alyte , f or a co mbined L OQ of 0 .04 ppm . 

### A cceptable con current method r ecov erydat a f or so ybean RAC samples wer e obtained f or ea ch an alyt e. Th e method L OD f or eac h anal yt e in/on so ybean 

## RA e s ampl es was 0 .004 ppm . Th e r e sults f rom the se ana ly

ses i ndicate that combined r esidues o f p yraclo strobin were 2 .6-10.5 ppm (20 O PA l, 1.8-10 .1 ppm ( 2 O PAl , and 1.8-9 .8 ppm (l O PAl in/ on treated soybean fo rage 

### sampl es, each harve sted 12-1 5 D ASA . Co mbined re sidues ofpyr aclo str obin were 5 .9-11.4 ppm (20 OPAl , 3. 6 - 14 .5 ppm (2 O PA l , an d 3. 9-10
. 0 ppm (l O PA l in/ on s oybe an hay s amples, e ach 

### har vested 2 0-21 D ASA. Combined re sidues o f pyraclo strobin were < 0. 05 and < 0.08 ppm (20 O P A l, < 0.04 ppm ( 2 an d I O PAl , i n/on s oybean s eed s amples , e ach harve sted 2 1 d ay s aft er th e 

### f ourth a pplication (2X th e prop osed appli cation ra te) . T he re sidues o f pyraclo strobin between th e v ari ous applicati on spr ay volumes wer e comparable on all soybean RACs. T ABLE 6. S ummary of Residue Data f rom C rop Field T rials with P vractostr ob t n . C

om modity T ota l PH I A n alyte R esidu e L evels Applic . day , co m

R

ate GPA n ' M in Max HAFT Med ian M , an St d. Ib ai/A 

# , Dev . Pag e 12 o f 27Pyraclo strobin Summary of Ana lytical Ch emistrya nd Re sidue Da ta DP #: 37 1252 TABLE 6. S ummary of Res idue Data from C rop Field T rials w ith Pvr aclostrobm. Commo dity Total PHI Ana lyte R e si due Lev e l s A ppli c. day s oom Rate GPA 

### n ' Min Mox HA FT Median Mean Std. I b ai/A z Dev . Fora ge 0 .39

- 1 2-15 Pyraclostro bin 20 6 2.26 8 .57 8
. 3 3 3 .0 1 4 .5 4 2
. 96 0 .4 1 500M0 7 0 .33 2 .01 1. 98 0.46 0.9 3 0 .8 1 Total 2
. 60 1 0 .5 0 1 0
. 3 0 3 .45 5 .47 3 .76 

### I Pvraclo srrobin Pyraclostrobi n 2 6 1.54 8 .2 2 7 .82 2.59 4 .00 3.0 0 5 00M07 0.2 1 1.89 1.84 0.46 0 . 84 0 .79

Tot al 1.80 10. 10 9 .65 3. 0 5 4 .85 3
. 77 

### I Pyrac lostrob in Pyrac1o strob in 1 6 1. 60 7 .95 7 . 54 2
. 63 3 .9 5 2. 84 500M 07 0.2 0 1.88 1.76 0 .46 0 .82 0 .74

To tal 1. 80 9.80 9 .30 3 . 10 4 .77 3 .5 8 

### I Pvraclostrob in H

ay 0 .39

- 2 0-2 1 Pyraclo strobin 2 0 6 4 .96 9 .5 2 8 .6 3 7 .3 4 7.03 1. 69 0 .41 500M0 7 0
. 89 1. 8 3 1. 73 1. 23 1. 28 0 .3 8 Total 5 .90 1 1.40 1 0.40 8 .60 8 .3 5 2 .0 6 I Pvr aclo strob in Pyraclo stro bin 2 6 3.13 1 1.40 10.56 4 .26 6 .06 3
. 56 5 00M0 7 0.5 1 3 .06 2 .66 0 .89 1.3 6 1.06 To t al 3 .60 14.5 0 13. 25 5 . 05 7.42 4 .64 

### I Pvrac1ostro bin P

yrac1o strobin 1 6 3
. 3 7 7 .90 7 .85 5.26 5.5 1 2. 06

50 0M07 0 .55 2 .14 1. 98 1.16 1.23 0 .65 Tota l 3
. 90 10. 0 9 .80 6 .40 6
. 72 2. 69 P

vraclostro bin Seed 0 .80

- 2 1 Pyraclostrobin 2 0 2 0
. 03 0 .06 0
. 05 0 .05 0 .05 

### Nl A 0 .8 1 500M0 7 < 0.02 < 0. 02 < 0. 02 < 0 .02 < 0.02 

### Nl A Total 0
. 05 0
. 08 0 .07 0 .07 0 . 07 N /A 

## I Pvraclostrob in Pyrac lostr obin 2 2 <0 .02 <0 .02 < 0.0 2 < 0. 02 < 0.02 

### Nl A 500M07 <0 .0 2 <0 .02 < 0 .02 < 0. 02 < 0 .02 

### N / A Tota l <0 .04 < 0 .04 <0 .04 < 0.04 <0.04 

### N/ A 

### I Pvrac lo str obin Pyracl o stro bin 1 2 < 0.02 < 0. 02 <0 .02 <0.0 2 <0.02 N /A 500M0 7 < 0. 02 < 0.02 < 0.02 <0.02 < 0.02 

### Nl A Total < 0.04 < 0.04 < 0 . 04 < 0.04 < 0.04 N /A 

### I Pvraclo str obin n nu mb er o f individ u al s pec i me n s 2 HAFT = H igh est A ver age F iel

d Tr ia l b

ased on comb ined res i du es ' N

/ A = N ot a pp

li

cab l e 

### Fie ld Trial A dj uvant s MRJD47774702 

### Page 13 of27Pyra clostro bin Summary of A na lytical Che mis try and Re si due Data DP# : 37 1252 Th e reg i s trant h as s ubm itted a data s ummary a lar ge part o f w h ic h wa s on soyb ean se ed s. Th e seed data indicate th at w hether usi ng the do me st ically registered pr oducts, Head line Fungicide [7969- 186] o r H eadline SC Fun gicide [79 69-289 ] w ith an adj uvant a dded to the 

### tank mix o r fo reign p roducts, e.g ., BAS 5 00 OOF, wh ich in clude several d ifferen t adj uva nts d irectly in th e form ulation, very l ittl e p yraclostrobin i s f ou n d u s ing th e l abel use p attern « LOQ ; 0. 04)
. Su mmations o f t he submi tted soy bean f orage an d h ay adj uvant d ata i s pre s ented i n Ta b le 7, below. The d ata i ndicate that m o stl y para ffin a nd fatty o i ls we re u sed in th e s ub mitt e d s tu di es fo r w hich a djuvant da ta ar e ava i lable. N o d i ffere n ces i n residue d ata ar e apparent b etween th e s tud i es w hich d id not li st a speci fic adjuvant and th ose th at d id re s idue data for pyra clostrobin w hich were es sentia lly i dentical to th e o t he r s tud ies. TABL.E 7
. Summary o f Adjuvan t Use wi th For age and Hay Resi due Dat a. Ad juvant Amo unt Rate App Soy bean S oy b ean Ad ded Ad ded Vo l. Forag e Hay ( co mpo sition) ( % ) (n UA ) (GPA' (nn ";' Inn ';" 200 2 Tria ls AdSpray 0 .5 NR 3 9 2 .78,3.25 0 .87, 1.11 ( alkylary lp olya lkoxylated I elvco ls and d erivatives) 0. 5 NR 2 3 3 .8 1,3. 87 2.1 3,2.15

Penetra tor P lu s ( non -ionic s urf actan t s in 0 .5 NR 30 1. 7 9 ,1 .40 1.0 1,1. 04 par affin oil and bu ffering agent s) Agr i-Dex 0.5 NR 25 0 .84,0 .96 1.76 , 0
. 05 (n on -io nic s urf actan ts in p araffin oil and b uffering 0 .5 N R 2 5 2.71 ,3.37 1.2 3, 1.28 ag en t s) Act ivator 9 0 ( alc oho l ethoxy lates and 0
. 5 NR 20 1 .64 , 1.54 6.1 3,5.95 fattv a c ids) Pref e rence 0.5 NR 25 1.47 ,0.74 2 .39,2.39 ( alk yl pheno l e thoxylate, so dium so ya fatty acid s , 0 .5 NR 25 2 .2 1, 1. 59 2.5 0,2.63 a nd ld s ooroovl alco hol) Aqu agene ( alky l ary lpolyoxy-et bl yene 0 .5 NR 3 5 1.09 ,1. 08 2. 67,2.63 et her , i s opropanol , and f attv acids) Loc ally Availa b le 0 .5 NR 3 4 3 .06,2.25 1.1 7,0.91 ( " not e xac tly s pe cified?" ) 0.5 NR 3 0 1.38 , 1.89 2.1 0,2.15 0
. 5 N R 28 0 .78, 1.02 1.04 , 0.86 0.5 NR 20 2 .55, 1.56 2.3 4,3.7 8 0 .5 N R 30 1.74 , 1.79 2 .78 ,2 .36 0 .5 NR 3 0 2 .69,3.50 3. 47,2
. 84 0 .5 N R 3 2 1 .52, 1 .40 2.28 ,2.39 0 .5 NR 3 0 2 .22 , 1.91 2.42 ,2 .19 2 008 T ria l s R-way N R 0 .3 20 10
. 51,10 .1 1 1.3 5, 9
. 3 6 ( p ara ffin oil and NR 0 .5 2 10 .11,9.21 14.46, 1 1.97 s urfactan ts) N R 0.5 1 9 .8 3,8.77 9 .60 ,10.04 H e lena C rop Oil N R 0 .5 20 3 .3 5,3
. 59 8 .35 ,8 .78 P age 1 4 of27Pyra c lo s trob in S ummary o f Ana lytica l Ch e mistry and Re s idue D ata DP #: 3 7 1252 TABLE 7
. Summa of Adjuvant U se wi th Fo ra ee a nd Hav R esid ue D ata. A djuvant A moun t Rat e A p p S oybea n So ybe an A dded A dded V o l. Fora g e Ha y (c omposition) ( % ) ( o vA ) IO PA) ( 0 0 ';; ) ( DO ';' ) ( para ff in oil , po lyo l fatty 

### NR 0 .5 2 3
. 03 ,3
. 0 5 4
. 32 ,5 .8 5 acid e st ers , a nd p o lyetho x y lat e d 

### NR 0
. 58 I 2.71,3 .4 6 5
. 50 , 7.32**de ri** **ati ~)**  Prime O il 

### N R 0 .5 2 0 2
. 66 ,2 .59 6
. 1 8 ,5. 8 7 ( P a raffin o il and p o lyo l f atty a cid e sters , a nd 

### N R 0 .5 2 1.8 6 , 1. 75 4
. 31,3 .64 p o l yet hoxyl ated**ivative** 

### N R 0
. 5 1 1
. 80, 2
. 00 4 .05 , 3.93 Avg 3
. 0 3 4
. 03 Max 10 .5 1 1 4 .46 M in 0
. 74 0
. 0 5 S tdDev 2. 6 0 3. 2 9 N R

- n ot r ep orted 

### * D irect q uote fro m M RID 4 7774702
Co nclus ion. Th e petiti oner has pro vided adequate brid gi ng re sidue data reflecting the maximum propo sed u se pattern o f pyrac lo s trobin i n/on soy bean forag e and hay . The comb ined residue s of pyr aclo strobin and it s m etabolite BF 500- 3 did not exc eed th e pr opo s ed t olerance l eve l s o f 1 1 .0 ppm and 1 4 .0 i n/on s o ybean forag e and h ay , re spectively , f ollowi n g tw o app l ications o f th e 2
. 0 Ib

/gal E C formu l ation. The combined residues of pyra c l ostrobin were 1.8 -10 .5 ppm u sing 1 -20 O PA application vo lume in/o n tr eated s o yb e an f orage s ampl es , harv e st ed at 1 2- 1 5 PHI. C ombined re sidu e s of p yraclostrobin w e re 3 .6 -14 .5 ppm u sing 1

- 20 GP A appli cation vo lume in/on s o yb e an ha y s ample s, harv ested at 20 -21 PHI. Re sidue da ta in soy bean f orage an d hay s howed c omparab le residue s o f par ent an d its m etabolite w hen th e fung icide ( BAS 5 00 0 0 F Fungicide) w as appli ed, at the label rate , in s p rays app lied at 20 , 2 , or 1 G PA u sing a ground app licati o n device. S amp les we re analy zed u sin g an adequate anal ytical m e thod , and ar e s upporte d by th e availab le s tora g e s tab ility data
. The numb er and loca tion s of fie ld tr i als are in accordance with O PPTS G uideline 86 0.1500 , C hemSAC r ecommendations , and th e co nducted field tri als r eflect th e maximum propo sed f oliar u se patt ern . Th e field tri al data f or a ll s oybe an f orage and hay r eflecting the prop osed app l ication rat e ( s ubmitted here and pr eviou s ly s ubmitte d in M RID 4 5903602) were e ntered i nto th e Ag enc y ' s tol eran ce s preadsheet as s pecified by th e Gu ida nce fo r S etti ng P es ticide T o l eran c es Ba sed o n Fi eld T ria l D ata SOP to determine an appropriate to leran ce level ; s ee A pp e ndi x II
. Th e to lerance s preads he et re commends f or th e prop o s ed tolerance s o f 11 .0 ppm and 14
. 0 ppm for s oy bean f orage and h ay , re spectively
. N o soybean see d re sidue dat a wer e c o llect ed at th e lab e l rate . D ata o btained i n thi s s tudy w ere at 2X the l abel rate i ndicat ed low level s o f p yraclo strobin re sidue s (LOQ

- 0 .08 ppm ). N o c hange in the soy bean s eed tolerance i s required fro m the propo sed u se . Th e adjuvant data i ndi c ate that mo stly par affin and f atty o il s w ere u sed in th e s ubmitted s tudie s for w hich adju vant data are availab le
. T he s tudi es whic h d id n ot li st a s pecific adju vant h ad r e sidu e data f or pyr aclostrobin w hich w ere e ssentia lly identical t o the o ther s tudie s. A RIA co nclude s th at there are i ns ign i fic an t dif ference s in the ef fe ct s , i f n ot type , o ft he adju vant s u sed 

### Page 1 5 of 27Pyraclo strobin Su mmary of An alytical C hemistry an d R esidue Data DP # : 37 1252 in th e s prays, bet ween the 200 2 and 2008 s tudies; ther efore , th e no additional field trial s are n eeded. A RIA rec omm ends f or th e proposed s oybean fora ge and ha y tol erances and the pr oposed u se of p yraclostr obin
. 

### 860 .1520 Process ed Foo d a nd F eed PP#s 3F658 1 , 2F6431 , 2 E647 3 , 3 E65 48 , 3E6 553 , 3E6774 , and 2 F6139 ; DP # s : 2 8 1 0 4 2, 2 86732 , 2 87729, 28845 9,2 9 0342,2 903 43,2903 6 9.29244 0,293 08 8,2936 84, 2 958 93,2 9817 8 ; L
. C hen g , 7/26/0 4 Th e pr eviously s ubmitted s oybean proc essing s tudy indi cates that the c ombin ed re sidu es of pyr aclostr obin and it s me tabolit e B F 5 00-3 ma y co ncentrate s lightly i n s oybean hull s (1 .3x ave rage proce ss ing factor ) but d o not app ear to c onc entrate in soy bean m eal and refined oil. 

### Conclusion. Th e result s of th e s ubmitted field trial data indicate th at there i s n o in crease required on s oybean s eed
. Ba sed o n the field tri al d ata and th e pr eviously s ubmitted soy bean pr ocessing s tudy , tolerance s f or soy bean m eal and re fined o il are n ot r equired
. 

### 8 60.1650 Su bmi tt al of Ana lytica l R eference S ta nda rds Analytic al s tandards f or pyraclo strobin and it s regul ated m etab olite s ( BF 50 0-3) are c urrently a vailable in the EP A National P e sticide Standard s R epository ( e-mail corre spond ence with T. 

### Co le
. 2/17 /0 9). 860 .1850 Confin ed Acc umulation in R ota tional C rops M ARC, DP # 27 8044, L. Che ng , 10 /9/01 PP #O F6139 , DP # 269668 , L. Che ng, 11/28/0 1 An ad equate co nfined rotati onal c rop s tudy w as reviewed in PP #O F61 39. Th e s tudy s howed th at the metaboli sm o f pyracl o strobin in rotated c rops i s si milar but more e xten s ive than th at in prim ary cr ops . P yraclo strobin und ergoes demethox ylation to yield B F 5 00-3 , foll owed b y further degradation to m edium p olar and p olar me tab olite s , and s ubsequent conjugation r eactions and in c orpo ration into na tural product s. The H ED M ARC h as determin ed th at th e r esidues o f c oncern in rotat ional c rops co nsist o f pyraclo s trobin and m etabolite SF 50 0-3
. 

### 860 .1900 F ield Acc umu lation in Ro ta ti ona l C ro ps PP #OF6139, DP # 2 6966 8 , L
. Cheng, 1 11 28 /01 A limit ed field rotational c rop s tudy w as re viewed in PP #OF6139. The res ults indicate that residues o fpyr a clostrobin and it s metabolite B F 50 0-3 were each le ss than the method L OQ «0.0 2 ppm) i n/on rotational c rop m atrices (radish , ro ot s and tops ; ca bbage , w ith and w ithout vvrapper lea ve s ; and w heat forag e , h ay , and grain) planted 14 day s foll owing the l ast o f s ix se quential f oliar applications to th e pri mary crop, c ucumbers, o f the 2lb /gal EC f ormulation at 0 .19 - 0 .20 lb ai/ A1 appli cation
. Re sidues of pyraclo strobin i n/on o ne s ample o f wheat s traw from th e CA te st s ite we re a t th e L OQ ( 0.02 ppm) , but r e sidu es of pyracl o strobin in/ on a repli cate s ample from th e s ame plot were belo w the L OQ (0 .012 ppm ) fo r an ave rage re sidue o f < 0. 0 2 ppm . Re sidue s o f metabolit e BF 50 0-3 w ere nondet e ctable «0 .02 ppm ) in/on all s amples of whe at s traw . 

### Page 1 6 o f 27Pyra c1o strobin S ummary of A nalytica l Chem istry an d Re sidue Data D P# : 3 71252
Th e registered p yraclo s trobin end-use p roduct labels presently s pecify a 1 4-day pl antback interva l res triction for a ll crops that are not regis tered. 860 .1550 Proposed T olerances T he H ED MAR C (DP # 2780 44 , L. C heng, 10 /9/0 1) h a s de termined th at for p urposes o fto lerance and dietary ri sk as sess ment s, the residue s of co ncern i n p lant and rotationa l c rop commo ditie s i nclude pyraclostrob in and it s des methoxy metabolit e, BF**500** The re s idue s of co ncern in l ive s tock commoditie s include pyraclostrob in and i ts me tabolites convertib le to**1~ (4**  c h lorophenylj

- Ijf -pyrazol-S-ol (BF 500 -5) and 1 -(4-chloro-2 -hydroxyp henyl)-IH-pyrazol-3-ol (BF 500-8). Pyraclo strobin to lerance s for pl ant c o mmod itie s are l i s ted in 40 CFR § 1 80.582 (a) ( I) an d are ex pres se d in term s of th e combined re sidues of the fungicide pyraclo strobin (carbamic acid, [2- [[[ 1-(4-chlorophenyl)-I H- pyrazol -3-yl]oxy]methyl]phenyl] methox y - , methyl es ter) and it s des methoxy metabo l ite (methy l N - [[[ 1-( 4- chlorophenyl)-1H -pyrazol-3-yl]ox y]methyIJp hen y l carbamate) , ex pressed as parent co mpound
. Pyraclos trobin to lerances for livestoc k co mmodi tie s are li sted in 4 0 C FR § 1 80.582 (a) (2) and are ex pre ssed i n term s of th e com bined r esidue s of the fung icide pyraclostrobin and its me tabolit es conve rtible to 1-(4- chlorophenyl)-1 

### H -pyrazol-3-01 and 1 -(4-chloro-2-hydroxyphen yl)- IHpyrazo l- S col, e xpressed as pare nt compo und. The field tria l data for all soybean forage an d h ay reflecting th e propo sed applicatio n rate were e ntered int o the Agency ' s to lerance s preadsheet as s pecified by the G uidance for Setting Pesticide Tolerances Based on Field Trial Data SOP to determin e an approp riate to lerance level. Th e tolerance sp read sheet recommend s for the proposed tolerance s of 1 1 .0 p pm and 1 4 .0 ppm for soybean forage and hay , respectively. There are no Codex MRLs for pyraclostrobin for th e crop commodities di sc ussed i n thi s docwnent
. A s ummary of the recommended tolerances for th e c rop commodities di scusse d in th i s doc ument i s pres ented in Table 6
.

TABL E 6. Tolera nce Summary for Pvraclostrobi n . C ommod ity Propo s ed Recommended Commen ts; Co rrect Co mm od ity Definitio n T olerance ( oom) Tol erance ( ppm) Soybean , foraae 1 1. 0 I I

S oybean
. h ay 1 4.0 14 

### References DP # s: S ubject : 281042 ,286732,287729 ,288 459,290 342,290 343 ,290369 ,2924 40 ,293088 , 29368 4 ,295893,298 178 Pyraclo strobin
. PP #3 F0658 1 , 2F06 4 3 1 , 2E6 47 3, 3 E6548, 3 E6553, 3E 677 4 , and 2F06139
. P etition s for th e e s tabli shment of permanent tole rances to a llow use s on Page 1 7 of27Pyra clostrobin Summary o f Ana lytical Ch emi stry and Re s idue Data DP# : 3 71252

From : To: Date d : 

### MRIDs :

DP #s : Subject :

From : T o: 

### Da ted: MRIDs:

DP # : S ubject:
From : To : Da ted : 

### MRID s : corn (fie ld , s weet , and p op) , hops , mi nt, pome fruits , edi ble-podded l egume vegetables , s ucculent peas , s unflower, Brassica leafy green s, soybeans, s ucculent be ans, broccoli, cabbage, l ettuce (head and leaf) , sp inach, celery , turnip gree n s, and the i mport com modities mango and papaya. App lication for amended Sect ion 

### 3 regi stra tion for ci tru s (re duced PHI). Pet itioner 's re sponse to data deficiencie s identified i n PP #OF06139 regarding s to rage s tabi l ity d ata, dried s helled peas and b eans (red uced PHI) , and use s on dry and s uccu le nt peas. S ummary o f Analytica l C h e mi stry an d Resi due Data. 

### L. 

### Cheng C. Giles-Parker / J. Bazui n 7

/26/0 4 

### 455962 11 ,4 5623406 ,4 5623407, 45623408 ,4 562341 0 ,4 5645801 ,4 564 58 02 , 4564580 3 ,4 5 645804,4 5702901 , 45765401 ,4 583 20 01 ,4 5858801 , 45858802 , 45903601 ,4 5903602 ,4 60339 01- 04,4 60 844 01-04,4 61 091 01 ,4 61 091 02 269668 ,272771,272789 ,27 4095 ,27 4 192 ,27 4471 ,27 4957 ,2758 43, and 278429 PP#OF06139
. Pyraclo st robin on Variou s Crops: Bananas ( import) , Bar ley , Berr ies, Bul b Vegetab les , C itrus Fruit s, Cucur bit Vegetab le s, Dried S helled Pea & Bean ( except Soybean) , Fruiting Vegetables, Gra pe s, G rass, Pean ut, Pi s tachio, Roo t Vege table s (exce pt S ugar Bee t), Rye , S nap Bean s, Stone F ruits , Straw berry , S ugar Beet , Tree Nu t s, T uberous an d Conn V egetab l es , and Wheat. Review of Ana lytical M ethods and Re sid ue Data
. 

### L. 

### C heng C
. G ile s -Parker !J
. Bazuin 11128 /01 

### 4511 842 8-4 511 84-37 , 45 1 1850 1-451 18512 , 4511 8514-4 51 18537 , 4 511 8601- 4 5 11 8625 , 4 51 60501 , 45272801 ,4 5274901 ,4 5321 101 ,4 5367501 ,4 5 3 99401 , a nd 45429 901 27804 4 PP # OF06139. P C C ode 099 100
. P yra c1 o strobin
. Outcome of the H ED Metabo li sm A s sess ment Review C ommittee (MAR C) Meeting Hel d o n 

### Se pt

emb er 20, 2001. L. 

### Cheng Y
. Donovan 10

/09 /01 N one



### Page 1 8 of27Pyraclostrob in Summary of Ana lytical Chemi stry a nd R esidue Data DP #: 371252 

### DP#: 

### S ubjec t: Fro m : T

o: Dated : MRlD s:
DP# : 

### Subject:

Fro m: T o: Da ted : MRl Ds : 2 69850 PP# OF06139
. Pyraclostro bin (BAS 5 00F) in o r on Var iou s C rops . Re que s t for T olerance Metho d Validation (TMV) Trial. L. 

### Cheng F. D
. Griffith , Jr
. 1 1/8/ 00 4 5118505 ,4 5118504 ,4 5118509 ,4 5118510 ,4 5118501 ,4 5 11 8503 ,4 5118507 , 4 5118514 28 1042 ,286732 ,287729,288 459, 2903 42,2903 4 3 ,290369 ,292 44 0,293 088 , 29368 4 ,295893,298178 Pyraclostro bin
. PP#3F0658 1 , 2F06 431 , 2E6 473 , 3E65 48, 3E6553 , 3 E677 4, and 

### 2F06139. Pe titions f or the establishmen t o f permanent to lerance s to a llow uses o n corn (fie ld , sweet, and pop), hops , min t, pome fru its, edible-podded l egume vegetables, su cculent peas, s unflower, Bras sica 

### leafy greens , s oybeans, s ucc ul en t beans , br occoli , ca bbage , lettuce (head and leaf) , spi nach, celery, t urnip gree ns, an d th e import co mmoditie s mango and papaya . Application for amended Section 3 r egistration for citru s (red uced P HI). Pe titioner's r esponse to data deficiencies identified in PP #OF06 139 re garding stor age sta bility data , dried she lled peas an d beans (red uced PH I), and uses o n dry an d succulent peas. Sum mary o f Ana lytical C

hemistry a nd Resid ue Data. L. 

### C he ng 

### Cyn t hia Gile s - Parker 7/26 /0 4 45596 2 11,45623406 ,4 5623407 , 45623408, 45623410,4564580 1,45645802,45645803, 45645804 ,45 70290 1, 457654 01, 458 32001 ,45 858801,4585880 2 ,4590 36 01 ,45903602, 4603390 1-04 ,4608440 1-04,46 109101 ,46109 102 

### Attac hments: A ppendix I - Int ern ational Residue L imit Stat us sheet Appe ndix II . Tolerance A ssess ment Ca lculations

Page 1 9 of27Pyra clostrob in Summary of A na lyt ical Chemi stry and Re sid ue Data DP # : 3 7 1252 

### Appendix I

- International Residue Limits
INTERNATIONAL RES IDUE LI MIT S TATUS Che mical N ame : (carbam ic C ommon Na me : [EJ Propo sed t ole ra nces Date : 5 /10/ 10 acid, [2-[[[ 1- (4- Pyra c1ostrobi n 0 Reeva luated tole rance c h loro ph e n y l)- l H -p yrazo l- 3

- 

### o Ot her y 1

] oxy ] methy 1] pheny I ] m ethox y- , methyl e ste r ) and it s d e s m et hoxy metabo lite (methyl-N-[[[ 1 -( 4

- chl orop heny1)

- l H-pyrazo l- 3

- y I]oxy] meth y l]ph eny lcarbam ate) , e xp ress ed as p arent c o mpou nd C odex S t at u s (Maximum Residue Lim itsl U . S. To leran ces UN o Codex proposal step 6 or above P e tition Numb ers: PP #9F7569

No C odex pro po sal s tep 6 or ab ove f or the crop s O ther I de ntifi e r : reauest ed Re s id ue definit ion ( step 8/CXL): pyrac1ostro b in ReviewerslBranch : W
. Cu t c hin R esi d ue definit ion in PP #8 F7385
. PP #8F7390, and PP #8E7394: Comb ined re s idu es o fpyrac1o strobin and BF 50 0 -3, exnre ssed a s nvra c1 o strobin
. C ro p ( s) MRL (m glkg) Crop ( s) R ecommended To leranc e (pp m) So ybean, forage 1 1.0 S oYbean, hay 1 4 .0



### Page 20 o f27Pyracl os trobin S ummary of Analytica l C hem istry an d Re sid ue D ata DP # : 37 1252 Limi ts f or Canada Li mits fo r Mexico D No Limi ts D No Li mits ...j No L imits f or the cro ps r e q ues te d D No Lim its for the c rops req uested R esidue de finitio n : Re sid ue de fmition : M exico ado pts Co dex and /or fant: m ethyl [ 2 -[[[ 1

- (4 -c hlo ro pheny l)- IH-pyrazol -3- US MRLs/ to ler anc es f or it s e x po rt p urp oses . l]o xy]methy l]pheny 1 ]methoxycarbam ate , includi ng th e metabo l ite [ 2 -[[[ I ( 4 -c hlorophenyl) -I H -p yrazol

- 3-

I ]oxy ] methy l]phenyl]carbam ate ivest ock: m e thyl [2 -[[[ 1-(4-c h loroph e ny l)

- I H -pyrazo l- 3

- I] oxy]methy l]phen yl]methoxycarbamate , in cl uding the metabolit es co nv ert ib le t o 1-(4 -c hlorophe ny l )- 1 H -pyrazo l-

-0 1 and 1

- (4-ch lo ro-2 -h ydro xyph e ny1) -I H-p yr azol

- 3

- o l Croo ( s) M RL (mVklll C roo ts MRL (mVk l!: l

S ,Fun kIM ,Ne us sie, 05 / 1212 010
.



### P age 2 1 o f27Pyracl o strob in S ummary of A nalyt ical C hemistry and Re sidue Data DP # : 3 7 12 5 2 

### Appendi x II. Tolera nce Assessment Calculations The field trial data for all s oybean f orage and hay reflecting the propo sed app l ication rate ( submitted here and pr evious ly s ubmitted in MRID 45 903602) were entered into the Agenc y's to lerance s pread s heet as s pecifi e d by the Guidan ce for Sett ing P esticide Toleranc es B a sed on Fiel d Trial Da ta SO P to dete rmine an appropriat e tolerance leve l ; s ee Appendix II. The to lerance s preadsheet rec onunend s for t he propo sed to lerance s o f 11 .0 ppm and 14 .0 ppm for s oybean f orage and hay , re spectively.
Reaulator : E PA C hemical: p yraclo C ron: SO Y f orae e PHI : 1 2-1 5 day App. Rate : Submitter: Residues 2 .7 8 3. 2 5 0 .8 7 1.1 1 3
. 81 3. 87 1. 39 1. 79 0 .84 0
. 96 2
. 71 3 .3 7 1.3 8 1. 8 9 0. 7 8 1.02 1.5 4 1.64 1.5 6 2 .5 5 1.74 1.7 9 2
. 69 3
. 5 0
. 74 1.47 1. 59 2 .21 

### Pag e 22 of27Pyraclostrobln Summary of Ana lytica l C hem i stry and R e sidu e Data 1 .4 1.57 1.08 1.09 1.

91 2 .22 10 .5 10
. 1 10. 1 9 .2 9 .8 8 .8 3 .3 3
. 6 3 3 .1 2 .7 3 .5 2 .7 2 .6 1.9 1. 8 1.8 2



### Page 23 of27 D P # : 37 1252Pyracl ostrobin S um mary o f A nal ytical C hemis try and Re si due Da t a D P # : 37 1252
Logno rm al P ro b abili t y P lot

• EP A p y r a c l o so y forag e 12

- 15 d.ay y •**67 ~ 7**  •**.8 ~n**  R' •**l5**
11 .0 0 00 

# .'


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. 7 5 0 0 

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### • 

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98 .9**~O** 95 7 0 8 0 2 0 ) 0 

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. 60 7S L**--:' .L** **=-** 

### _ c ,

Re gulator : EPA Chem i ca l: py r a c l o C rop : soy forage

PH I : 1 2 -15 day App
. R ate: S ubm i t te r: n , 52 m i n: 0.74 max : 10 .50 m

edian : 1. 9 6 ave r a ge: 2 .9 7 95 t h P er c ent il e 99 t h P erc e ntil e 99 .9 t h Perc en ti le EO Me thod I 8.0 10 12 Norma l (9 .0 ) ( 11 ) (-- ) 9 5 /99 R u le 8
. 0 12 19 ( 10) (17 ) ( - - ) EO Met h od II 7 .0 Di s t r ib u t i on - Fr e e Mean + 3SD 11 U CLM ed ian 9 5t h 10

Ap proximat e 0.9358 S h a p iro -Fran cia 0.05 > = p-value > 0.0 1 

## , R e j e c t log normality assumptio n N

o rm al it v T es t
Would you like the abo ve values rounded? ( Y or N ) == > y 

### Page 24 o f 27Pyraclo strobin Summary of A nalytical C he

mistry a nd Re sidue Dat a

Reeulator : EPA C hemical: 

### I ovraclo C roo: S OY h ay PHI : 2 1 d av Ann . Rate: Submitter : Residues 0 .8 7 1.1 1 0 .9 1 1.1 7 2 . 13 2
. 15 1.0 1 1.04 0 .05 1.76 1.2 3 1.2 8 2
. 1 2 .15 0 .86 1.04 5. 95 6
. 13 2 .34 3 .7 8 2
. 36 2 .7 8 2 .84 3 .47 2 .39 2.3 9 2 .5 2
. 63 2.2 8 2 .3 9 2. 6 3 2 . 67 2 .1 9 2.42 11.4 

### P age 25 of27 DP #: 37 1252Pyraclo strobin Summary of A nalytical Chem istry and R esidue Da ta DP #: 3 71252 9
. 4 14.5

12 9 .6 10 8.4 8 .8 4 .3 5 .8 5. 5 7.3 6 .2 5.9 4 .3 3 .6 4 3. 9

Logn o rma l P robab ility P l o t

• EP A pyra cl o soy hay 2 1 d.ay y . o . 90 91 x • 1. 0 s

,, '

_ 0.n S5

15 .0 0 0 0
? ,S O O o ) , 1 500
1
. 8 ? SO
0 .n 1 5
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0 , n ..
O
. U12
0 ,0 586 •



## " so 10 80 eo
. 0 3 0 s 0.OH3 L

_ '-' Pue nt l l ..



### Page 26 of27Pyraclostrobin S ummary of Analyt ical C hemistry and Re sidue D ata DP #: 371252

Regu lator : EPA

Chemical : pyrac l o Crop: so y hay

PHI : 21 day App
. Rate: Subm itter: n , 52 min : 0 .05 max : 14. 50 median : 2. 6 3 average : 4. 04 95th Percentile 9 9 th P e r c e nt i l e 99 .9th P e r c en t i l e EU Method. I 10 12 1 5 Norma l ( 11) ( 14 ) ( 

### - - ) 95 /99 Rule 14 30 55 ( 25) ( 4 5 ) (- 

### - ) EU Method I I 12 Distribution-Free Mean+3SD I' UCLMedian 95th 13

Approx ima te 0 .8855 Shapiro-Franc ia p -va lue < = 0 .0 1 : R e ject l o gn or ma li t y ass umpt i on Normality Test
W

o u l d you like the abo ve val ues ro unded? ( Y or N ) == >



### P age 27 of2 7 y