Cyprodi nil Summary of Analytical Chemistry and Residue Data DP # : 425723 

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



### MEMORANDUM
Da te: March 30, 

### 20 1 6 OFFICE O F CHEMICAL SAF E TY AND POLLUTION PREVENTION



### SU BJ EC T: Cy prodioil. P etitio n Proposing a New Tolerance for th e Use of Cyprodinil in/on Tree Nuts Crop Gro up 14-12 ; except a lm ond
. except pistachios. 

### Summary of 

### Ana ly tical C he mi s t ry a nd R es idu e Data. PC Co d e: 288202 Dec is io n No .: 497939 P e ti t io n No.: 4F8333 Ri s k A ssess m e n t T y p e: NA TXR No.: NA MRJ D No.: 49470601 , 49470602, & 49470603 DP Barco d e: 0425723 Re g is tr atio n Nos. : I00-811 & I 00-1317 R egu la tory Ac tion : Secrion 3 C a se No. : 7025 CA S No.: 121552-61-2 

### FR OM : 

# 4 1#1Z tT hurston G. Mort on, Chem ist Ri sk Assessment Branch 4 H ea lth Effects Div i sion (7509P) 

### THROUGH: Eli ssa Rea ves , PhD , Branch Chief Risk Assessment Branch 4 Health Effects Div is ion (7509 P )


### TO: Marcel H oward F un g icide B ran ch Registration Di visio n (7505P)

P age 1of17Cyprodinil Summary of Ana l ytica l Chemistry and R es idue Data DP # : 425723 

### Exec uti ve S umma ry Cyprodinil i s an anilino-pyrimidine fungicide u sed to control various plant diseas es on a wide variety of fruit , nut , vegetable and herb crops. U nder PP #4E8 2 73 , Syngenta is requ estin g the establishment of tolerances for re s idu es of cyprodini l [4-cyclopropy l- 6-met h yl-N-pheny l-2

- pyrimidinarnin] i n/o n th e following raw agricultural commodities: N ut. Tree , G ro up 14-1 2; except al mond. except pistac hi o ........... 0.04 ppm In conjuncti o n with PP# 4F8 333 , Syngenta i s requ es tin g a Section 3 reg istration fo r In s pire Super
TM Fungicide (EPA Reg. No. 100-1317) , a 2.09 lb a i / gall o n emulsion oi l in water (EW) fo rmul ation to tre e nut s. In s upport of this n ew u se , Syngenta has submitted ne w m ag nitude of the re s idue data for cyprodinil. 

### T hi s produ c t (E P A R eg. No. 100-1 317) addressed herein contain s a second active in g redi en t (difenoconazole). T h e s ubj ect review ad dre sses the propo se d u se a nd s upportin g data for cyprodioil only. The nature of cyprodinil res idu es in plants is und e r stood based o n ad e quate m e tab o lism studie s on apple, p eac h , p o tato , tomato , and wheat. Only res idue s of parent cyprodini l n eed to b e includ ed in the t o leranc e express ion a nd considered for risk assessment for plant commod i ties. The natur e o f cyp ro dinil res idu es in ruminants is also understo o d ba se d on a n adequate goat metabolism s tudy. The r es idu es of concern in ruminant s are cyprodinil and it s hydroxylated metabo lite CGA

- 304 075 (free a nd conjugated). No poultry metaboli s m study is available, but HED has concluded that none is required. There are no new li ves tock feed s tuff s asso ciated w ith the proposed new u ses of cyprodinil. Adequate HPLC / U V method s (Meth o d s AG-631 and AG-631 B) are availabl e for e nforcing tolerances of cyprodinil i n/o n plant commodities. The limits of quantitation (L OQ) fo r the pl a nt methods ran ge from 0.0 

### I to 0.065 ppm dep e ndin g o n the commodity. An adeq uat e LC/MS m e th o d ( GRMO I 0.01 A) i s al so av ail able for enfo rci ng tolerances of cyprodinil re s idu es in live s tock commodities. The m e thod LOQ for thi s method is 0.02 ppm for the comb in ed r es idu es of cyprodinil and it s m e t a bolite CGA-304 075 (free and conjugated), ex pre sse d a s p a rent. Syngenta h as s ubmitted a high per fo rmanc e liquid chromatography method w ith t a ndem mass s pectrometry detection (LC/MS/MS) , method GRMOl 0.02A, for anal ys i s of res idu es of cy prod injl in/o n a variety of crops in c ludin g tree nut s . Th e method i s a modifi e d ve rsion of method 

### REM 141.0 

### I , th e o ri g in al enforcement m e thod for cyprodinil. A complete method d escription 

### (M RID 49470602) and s upportin g m ethod va lidati on data 

### ( MRID 49470601) ha ve been s ubmitte d. Th e m e thod was u se d for analysis of resi due s of cyprodinil in th e tree nut crop field lrial st udie s s ubmitted under th e current action (refer to 4947060 3. der ; B.7.6.1.1 ). Becau se the m ethod monitor s multipl e io n tran sition s for determination of c y prodinil , no confirm atory proce dure s are ne e d e d
. An I nd e pend e nt Laboratory Validation ( IL V) of th e method was not s ubmitted. Provid ed th e method is not prop osed fo r e n force m e nt , no ILV is nece ssary . No radiovalidation data hav e been s ubmitted for method GRMO 10.0 2A. The extract ion procedure s used fo r this meth od are the same as th ose used fo r the es tabli s he d enforcement m e thod o logy , for Page 2of 17Cyprodinil S umm ary of Anal ytical Chem istry and R esidue Data DP # : 4 25723 

### which radio validation data we re previo u s ly submitted and r ev iewed (refer to DP# s 233561 , e tc . , 2/ 20/ 98, G. Kramer); the refore , no additi o nal data are req uired. Th e LC/M S /M S m et hod GRM010.02A was ad eq uately va lidated for det e rmining res idu es of cyprodi nil in crops in c ludin g tree nuts. The validated LOQ is 0.0 I ppm. A confimrntory method is no t required because the method monito rs two io n transitions. In tree nuts harvested at a PHI of 13

- 14 days following the last of four foliar broad cast appli cation s of a 2 .0 9 lb a i / ga l E W formulation at a total rate of 1 .30 -1 .34 lb ai/ A , individual sample (and p e r-trial average) r es idues of cyprodin il we re < 0.010-0.0408 ( < O.OI0- < 0 .0 254) ppm in/o n pecan ( nutmeat) , < 0
. 0 1 0-0.0 14 6 ( < 0.0 1 0-0.0131) ppm in/on almond ( nutmeat), and 0
. 707

- 6.46 (0. 707- 5.48) ppm in/on a lm ond ( hull s)
. In the one r es idu e decl in e trial , re s idu es of cyprodini l generally d e clined in/on almond nutm eat and hulls w ith increa s ing PHI. T h e Organization for Ec onomic Coo p e ration and De ve lopme nt (OEC D ) tolerance ca lculati o n procedures were u sed t o determine appropriate to leranc e level. A toleranc e leve l of 0.04 ppm for nut, tree, group 14-12 ; exce pt a lm o nd , except pistachiq in accord ance with · ' Reviewer ' s Guid e and Summary of HED Che m SAC A ppro va ls fo r Am e ndin g Crop Group/ Subgroups [ 40 CFR 1 80.41] and Co mmodi ty D efinitio n s [40 CF R 180. l (h)]" ( B. Schneider , 6/ 1 4/ 06). No Codex, Canadian , or M ex ican MRLs are established i n/on tree nut commoditie s other than pistachio and a lmond
. 

### Regulatory Recommendations and Re s idue C hemistry Deficiencies HED has exami n ed the residu e chemi s try datab ase fo r cyp rodinil. With r eg ards t o cy prodinil for PP#4 E83 33 , p e nding s ubmi ssion of a revise d Sect ion F (see requirement s under Proposed Tolerances) , there are no residue chem istry issues that would precl ude granting amended registration s for In spire S up er r" 

### Fungicide (E PA R eg . No. I 00-13 I 7) to ex pand c urre ntl y registe red foliar use s for nut , tree , gro up 1 4- 12 , e xce pt a lm o nd and p is tachi o or establ i s hment of tolerances for re s idue s of cyprodini l on ly in/on the fo ll owing commod ities: Nut , tree , gro up 14- I 2, except almond and pi s tachio
.. .......... . .. 0.04 ppm A human h eal th ri s k assessment is forth co min g. 

### Notes to PM: Tolerance should be revised , as needed , to reflec t th e correct commodity definitio n s as specified in Table 8. 

### Backgro und Cyprodinil i s an anilino -p yrimidine fun g icide u sed to co ntrol vario u s plant diseases on a wide variety of fruit , nut , vege table and herb cro p s. To l erances fo r res idu es of cyp rodinil have b een estab li s hed in/o n a variety of cro p commoditie s at leve ls rang ing from 0.02-170 ppm [40 CF R
Page 3of17Cy prodinil Summary of Analytica l C hem istry and R esi du e Data D P #: 425723 

### § 180
. 5 32 ]. Tol e ranc es have also been es tabli s hed at 0.02 ppm for cyp rodinil re s idu es in m eat byproducts of cattle, goats , horses, and s heep. No tol e rance is establ is he d 

### for poultry byproduct s. Th e chemical s tructure , nomenclature , and ph ys ico c he mical properties of the technkal g r ade of cyprodinil are prese nted 

### in Tables 

### 1 and 

### 2
.

Tab le I. Cy prod inil No m enc l ature . Co mpoun d H

# UNyN~ N**~** CH 3 Co mmon nam e Cyp rod inil Company experim en tal nam e CGA2 1 94 1 7 IU PAC name ( 4-c ycloprop yl-6

- meth yl- p yrimidin

- 2

- y l)-phen y l-amine CAS n ame 2

- ovrim idin ami ne . 4-e vc l opropyl

- 6-mct h vl-N-p h envlCAS regi s try number 121 552 -61-2 End

- use product (EP) 75% water-dispersible granule fonnula t ion (Vangard ® WG Fungicide: EPA Reg. No. 1 00-828): a mu ltipl e active ingredient (MA I) end -u se product ( In sp ire Super"' Fungicide: EPA R eg. No. I00 -1 3 17) fo nnul ate d as an e mul s io n [oi l) in water (EW). conta inin g 8.4% difcnoconazole and 24.1 % cvorodinil
Tab le 2. Ph ys i coc h e mic a l Properties of Tec hnic a l Gra d e ofCyp r o dinil. Parameter Value Reference Meltin g poi nt/ran ge 75
. 9 

## °c DP#s 345970 and 345 18 2
. W. pH 9.5 al 25 

### °c ( 1% aqueous di spe rsion) C utchin. 6/ 4/ 08 Density 1.21 g/c m 3 at 20 

### ° c W a ter so lubili ty {mg/L at 25 C) p H 7.6 16 pH 5 20 pll 7 13 pll 9 1 5 olvent so lubility (g/L at 25 C) ethanol 160 aceto ne 610 t ol uen e 460 n-octanol 1 60 n-hexanc 30 Vapor pre ss ure 3.8 x 1 0· <> mm Hg at 25 

## ° c Dissociation constant. pK, 4.44 at 20 

### °c Octanol/water partition coefficient. Lo g(Kow) 3.9 at pH 5 at 25 C 4.0 at pll 7 4.0 at p it 9 UV/v i s ible absorpiion s pectrum 29.200 l / mol·crn at 270.8 nm (neutra l } (mo lar absorpt ion coeffic i e nt s for th e 29.200 l / mo l ·c m a 1 25 1 .6 nm (ac idi c) absorbance maximum) 29.200 l / mo l ·cm at 3 1 6. 8 nm (ac idic) 28.400 l / mol·cm at 270.8 nm (basic)



### P age 4of17Cyprodinil Summary of Anal ytical Chemistry and Residu e Data DP # : 425723



### 860.1200 Dir ectio n s for Use T ab l e 3. S ummary o f Prop ose d D irectio n s for Use o f C y p ro din il Applic. Timing , Fonnulation Applic. Max. No. Max
. Seas onal PHI Use Direction s and Type , and [EPA Reg. Rate Applic. Applic. Rate (day s) Limitation s Equip. No.] (lb ai/A) per Seaso n ( lb ai/ A) Tree Nuts In spire Supe r A minimum r e treatme nt Broadcast foliar interval (RT ! ) of 14-21 Ground & 2
.09 lb / gal 0.33 4 impli ed 1.3 14 days i s proposed. Do not EW Aeria l [I 00-1 3 17] apply more than 2 applicati ons by a ir
. 

### Conclusions. The propo s ed u se directions are sufficient to allow for evaluat ion of the available residue data. 

### 860.1300 Nature of the Re s idu e - Plants DP # 2 19794, G. Kramer , 2/13 / 96 DP # 2331 8 2, G. Kramer, 2 /20/ 98 MAR C Decision Memo , DP # 243198, G. Kr amer , 3/ 11 /98 

### The nature of the residue in plants is ad eq uately understood base d on acc e ptable me tabo l is m s tudie s on app le, peach , potato , tomato , and wheat. The se st udi es indicated that cy prodinil is metabolized primarily by hydroxylation followed by sugar conju gation. C leavage of the amino bridg e, openi n g of the pyrimidine rin g, opening of the cyc lopropyl rin g an d formation of thiol ac tic acid co nju gates are minor pathways . Incorporation into s tarch was observed in p o tato tubers and wheat grain. The MARC rev i ewed th ese studi es and de termined that the residue of concern , for purposes of tolerance enforce ment and risk assess me nt , is cyprodinil. 

### 860.1300 Nature of the Re s idu e - Live sto ck DP # 233182, G. Kramer , 2/20/98 MARC Decision Me mo , DP# 243198 , G. Kram e r, 3/ 11 /98 DP # 34597 0 and 345 182 , G. Kram er , 6 /4 /08 DP # 362486, J. Stokes, 9 1 15 1 09 

### The nature of the re s idu e in ruminants i s adequately und e rstood based on acceptable lactatin g goat metaboli sm studies usin g ( 14 

### C-phenyl] and [ 14

### C-pyrimidinyl] cyprodinil. Th e metaboli s m of cyprodinil in ruminant s procee d predominantly v ia hydroxy lation followed b y conjugation with su lfuri c and gl ucuron ic ac i d. Breakdown of th e pyrimid inyl ring was seen on ly in the li ver and re s ult ed in Metabolite L l. Cleavage of the amin o brid ge between the phen y l and th e pyrimidiny l Page 5o f17Cyprodinil Summary of Analytica l Chem istry and Res idue Data DP # : 425723 

### rings was only a minor reaction as indi cated by the sma ll amounts of CGA 249287 found in the liver and kidneys of goats dosed with 

## (1 4 

### C-pyr imidi n yl ] cyprodin il. H ED originally concluded there we r e no cyprodi nil metabolites of toxicological or regulatory concern in ruminant milk and tissues based on the dietary burden assoc iated with the registered cyprodinil use s at that time (362486 , J. 

### Stokes , 09/ 15 / 09 ; 378920 , B. Cropp-Kohlligian , 10

/ 27 / 10). However , HED noted that if future uses significantly increase the potential liv estock dietary burden, then a n ew cyprodinil feeding study wou l d be required in w hi c h res idue s of cyprodinil and CGA 304075 (both free and conjugated) are determined. ARIA subsequently has concluded that the re sidues of concern for both ri sk ass ess ment and the tolerance definition should include the combined res idues of cyprodinil and m etabo lite CGA-304075 (free and conjugated) , exp ressed in parent equ ivalents. A poultry metabolism for cyprodinil ha s not been submitted and none ha s been requested si nce t h e potential dietary exposure of poultry to cyprodinil re s idues is extremely low ( e stimated at 0.005 ppm ba sed on canola mea l consumption). There is no reasonable expec tation of finite residues in poultry and egg . However , if future crops are added that substantially increase the poultry dietary burden, then HED may require a s tudy. S u mm a r y of M e t a b o li te s and D egra d ates to be includ ed in the R is k A ssess m ent a n d Tolera n ce Ex press i o n fo r Cvo r o din il M atrix Ri s k Assess m e nt Pl ant s cyprodinil Live s tock c y prodinil and CGA-304075 Water c y prodinil and CGA 249287 

### 860. 1 3 40 Residue Ana ly tica l Methods MRID #s : 4947060 I , 49470602 , Tolerance Ex pr ess i o n cvorodinil cy prodinil and C GA-304075 NA



### Enforcemenr methods
. Adequate HPLC/UV methods with column switchi ng (Synge nta Methods AG

- 631 and AG

- 631 B) are available for enforcing tolerances of cyprodi nil on plant commodities. The LOQs for these me thod s r ange from 0.01 to 0.065 ppm depending on the plant commodities. Method AG-63 1B also contains procedures for confirmatory analysis by GC/NPD
. An adequate HPLC/ MS method (GRMOlO.OlA) is also avai lable for enforcing tolerances in li vestock commodities. This method determines residu es of both parent and the metabolite CGA-304075 (free and conjugated), exp ressed as parent. The LOQ is 0.01 ppm for eac h analyte for a combined LOQ of 0
. 02 ppm. 

### Data collection methods. Syngenta ha s submitted a high performance liquid chromatography method with tandem mass spectrometry detection (LC /MS/MS) , method GRMO 10.02A. for analysis of residues of cyprodinil inion a variety of**cro~** 

### includin g tree nuts. The method is a modified version of method REM 1 41.01 , the origi nal enforcement method for cyprodinil. A complete method description ( MRJD 49470602) and supporting method validation data (MRJD 4947060 1) have bee n s ubmi tted
. The method was used for ana lysis of residues of cyprodinil in the tree nut crop field trial studies s ubmitted under the current action (refer to 49470603.der ; B.7 .6. l .1). Because the method monitors multiple ion transitions for determination of cyprodinil , Page 6of17Cyprodinil Summary of Analytical Chemistry and Residue Data DP #: 425723


### no confirmatory proc edures are needed. An 

### Ind epe ndent Laboratory Validation ( ILV) of the method was not submitted. Provided the method is not proposed for enforcement , no l L V is nece ssary . No radiovalidation data hav e been submitted for method GRM010
. 02 A. The extraction procedures used for this meth od are th e same as those u se d for the established enforcement methodo l ogy, for whic h rad iovalidation data were prev io u s ly s ub m itted and reviewe d (refer to DP #s 233561, etc., 2/20/ 98, G. Kramer); there fore, no additional data are required. Th e LC/MS/MS m et hod GRMO l 

### 0.02A was adequately va l idated for determining residu es of cyprod i ni l in crops in cludi n g tree nuts. The va li dated 

### LOQ is 0.01 ppm. A confirmatory method is not req uired bec ause the method monitors two ion transition s. 

### Conclusions
. The LC / MS/MS method G RM 0 10.02A was adequately validated for determining residu es of cyprodinil in crops includin g tree nut s. The validated 

### LOQ is 0.01 ppm. A confirmatory method i s not required b eca use the method monitors two ion transitions. 

### 860
. 1360 M ultires idu e Method s G. Kramer, 11/2811995 

### D ata are available depicting the recovery of cyprodinil and its metabolite CGA

- 232449 through F D A Multiresidue method te st ing protocols (C through E)
. 

### Acce ptable recoveries were obta i ned for cyprodinil in app le fort ified at 0.50 ppm u s i ng Protocol D. These data we r e forwarded to F D A. 

### 860 .13 80 S tora ge S tabili ty 0233182. G. Kramer. 02/ 20/ 98 0288706 , T. Blo e m .7 124/ 03 

### The maximum s torage interval for samples betwee n harv es t and extraction was 298 days (9.8 months) for pecan (nu tm eat) and almond ( nutm eat and hull s)
. Samples were anal yzed within 14 days of extraction. The petitione r i ndicated that sto rage s tab ili ty data were availab le for tree nuts (Syngenta Study No. T00306 2-07); howeve r , these data do not appear to h ave been revie wed b y the agency. Acce ptabl e s torage sta bility data are avai lable indicating that residue s of cyprodinil are stab le during frozen storage for up to 2 years in/o n a variety of c r ops including wheat ear and sta lk (D P #s 23356 1 , etc., 2/ 20/ 98 , G. Kramer). These data are acceptable to s upport s torage conditions and durations of samples from the submitted fi eld trial s . 

### 860.1400 Water , Fi s h , a nd I r ri ga t ed C rop s The proposed uses are not relevant to th is g uideline. 

### 8 60
. 14 6 0 Fo o d Handlin g The proposed uses are not rel evant to thi s guideline.

P age 7of17Cyprodinil Summary of Analytica l Chemistry and Residue Data 

### 860.1480 Meat , M il k, Po u ltry, a n d Eggs D P#s 345970 and 345182, W. Cu tchin , 6 /4/ 08 DP # 362484 , J. Stokes, 9/ 15 / 09 DP #. 378920, B. Crop p-Kohilligian , 10 /27/ 10 DP # : 425723



### Adequate cattle fee din g stud ie s are available for cyprodinil , and tolerances for cyprodini l residues in li vestock commodities were assessed in conjunction with petitions for tolerances on various plant commodities. Usi ng th e Agency's most recent guidance on constructing reaso nabl y balanced livestock diets the maximum reasonably dietary burdens (MRDBs) of li vestock for cyprodi ni l residues were calculated to be 0.88 ppm for beef cattle , 1.2 ppm for dairy cattle , and 0.005 ppm for poultry and swine. Ba sed on these MDBs, to lerances for residues of cyprod i nil and free and conjugated CGA-304075 , expressed in parent equivalents, were required on meat byproducts of cattle, goats, h orses, and sheep at 0.02 ppm (LO Q). Previous ly, HED recalculated the dietary burden using almond hull in place of wet apple pomace. Based on the proposed modified use pattern of cyprodinil on almond and consequently a proposed increase in the established almond hull 8.0 ppm tolerance to 20 ppm , HED recalculated the dietary burden usin g almond hull in place of wet apple pomace. The dietary contribution from the almond hulls alone did not increase the total d ietary burden. However, this proposed amended u se on a lmond s was w ithdrawn and the increased tolerance for almond hulls did not occur . 

### Conclusions. The proposed new uses do not contain any additional livestock feed stuff s other than those previously r eg istered , therefore , H E D has determined that the currently established 0
. 02 ppm to lerance levels for meat byproducts of cattle , goats , horses , and sheep are adequate. 

### 860.1500 C rop F ie ld Trial s MRJD #s 49470603 

### The results from the field trials are summarized below. In tree nuts harvested at a PHI of 13-14 days following the last of four foliar broadcast app l ications of a 2
. 09 lb ai/ gal EW formulation at a total rate of 1.30-1.34 lb a i/ A , ind i vidual sample (and per-trial average) res idue s of c y prodinil were < 0.010-0.0408 (<0. 010- < 0.0254) ppm in/o n pecan (nutmeat), < 0.010-0.0146 ( < 0.010-0.0131) ppm in/on a lmond (nutmeat), and 0.707- 6.46 (0.707-5.48) ppm in/on a lmond (hu lls ). In the one residu e decline trial , residues of cyprod i ni l ge nerally decl ined in / on almond nutmeat and hull s with increasin g PHI.

S u mm a r y of R es id u es from Tree Nut Fi e ld Tria ls wit h Cyp r od in i l
. C rop M atri x Total PHI n ' Re sidues { ppm ) Application (days) Min. 2 Max. 2 L/\FT3 llAFT3 Mcdian 3 Mean 3 SD 3 Rate ( lb ai /A) Pecan nutm eat 1.3 0-1.32 1 3 -14 5 < 0.0 1 0 0.0408 < 0.0 10 < 0.0254 0.0 104 0.0 13 3 0.00676 Almond nutmeat 1.31-1.34 14 4 < 0.0 1 0 0.0 1 46 < 0.0 1 0 0
. 0131 0.0 1 05 0.0 11 0 0.00 1 44 Almond hull s 14 4 0
. 707 6.46 0.707 5.48 3.00 3.0 .t 2. 03 1 n = number of field tnal s . 

### Page 8of17Cyprodinil Summary of Analytical Che mistry and Residue Data DP # : 425723
2 Valu es b as ed o n to tal numb er o f s ample s. 3 Values based on per-trial averages. LAFT = lowe st average field trial , HAFT = highest average field trial, S D = standard deviation. For compu t ation of the LAFT, I I AFT, median. mean. and standard deviation. values < LOQ were a s sumed to be at the LOQ (0 .010 ppm ). 

### Conclusion: The data adequately support the reque ste d tol eranc es and proposed u se pattern. 

### 860.1520 Proces se d Foo d and Fe ed None of the new uses have processed commodities that require a processing study. 

### 860.1550 Harmonization with Codex No Codex, Canadian, or Mexican MRLs are established in/on tree nut commodities other than pistachio and a lm ond. 

### 860 .1 650 Submittal of Analytical Reference Standards Analytical standard s for cyprodin il (expiration date 7 / 30 / 2018) and CGA-304075 (expiration date 8/ 3112016) are currently avai lable in the EPA National Pe stic ide Standards Repository (email communication with T. Co le , ACB, 04/ 08 /2015). 

### 860.1850/1900 Confined and F ield Accumu lation in Rotational Crops DP# D257898 , S. Levy, 2 1 81

2000 DP # D3 2 6346 , W. Wassell , 10 / 18/ 2006 

### A d equate confined and limited fi e ld rotational crop studies are available and were con duct ed at 2
. 2x and 1.5x the current maximum use rate for rotated crops (1.3 lb ai/A). On the basis of these stud ies , the HED requested a field rotational crop stud y which also monitored for residues of CGA-232449 , NOA -4 22054 , CGA -24 9287, and CGA-263208
. In the subsequent field accumu lat ion study , cyprodinil (WDG) was applied to mustard greens at four test si tes in CA (2 tests) and NY (2 tests) as four broadcast foliar applications at 0
. 328 lb ai/A/applicat ion at 7-day retreatment intervals for a total of 1.31 lb ai / A (Ix rate). The primary mustard greens crop was destroyed and re mo ved 7 days after the final application, and rotational crops of wheat , lettuc e and garden beet s we re planted at PBis of27 to 32 days. Samples of lettuce. garden beet roots and tops, and wheat forage, hay , straw and grain were collected from eac h test at the appropriate stage of maturity. All sampl es were analyzed for res idues of parent and each metabolite (CGA-232449, NOA-422054 , CGA-249287 , and CGA-263208) using an adequat e HPLC/MS method (Method 2213 -01 ) , which has a validat ed LOQ of0.05 ppm for parent and each metab o lite. As residues of parent and each metabolite were < LO Q in/on all lettuce , garden beet and wheat RAC sample s , HED concluded that rotational crop tolerances are not currently required. 

### 860.1550 Proposed To lerance s The Agency has determined that the residue of concern in plant commod i ties for the tolerance expression is only cyprodinil. Tolerances have been established for residues of cyprodini l in/on Page 9of 17Cyprodinil Summary of Analytical Chemistry and R esidue Data DP # : 425723


### a variety of crop com mod it ies, at leve ls rang in g fro m 0.02 pp m i n/o n almo nd to 340 pp m in citrus oil (40CFR§180.532(a)]. Tole rances have also been es tab li shed at 0.02 pp m for cyprodi ni l and its me tabolite CGA

- 304075 res idues in meat byproduc t s of cattl e, goats, h orses and s heep.

T a bl e 8. T o leran ce S umm a r y for Cy pr odini l Co mmodity Es tablished / Propo se d Recomm ended Comments; Co rrect Commodity Tolerance (ppm) Tolerance ( ppm) Defini tion T o ler a n ces Pr o p os ed U nd e r PP#4F8 3 33 Nut, tree , g roup 14-12 ; 0.04 0
.04 Nut, tree, g roup 14-12, excep t almond except almond
. except andpistachio pi s tachio


### Reference s DP Numbers: Subject: From: To: Date d: MRJD(s): DP N umb ers: Subject: From: To: Dated: MRJD(s): DP Numbers: Subject:

From: To: Dated: MRID (s): 378920 Cyp rodini l. Cyprod ini l. Amended Use and Amended To lera n ce Petition for Pome F ru it. S ummary o f Analytical C he mi stry and Re si due Data
. B. Cropp-Kohlligian L. Jone s I0/ 27/ 10 47644301 3624 86 Cy prodinil. Petition for Tol era nce on Canola Seed Imported from Canada. Summary of Ana l ytical Chem istry and R e s idue Data. J. S toke s L. Jone s 09/ 15 / 09 47644301 3 45970 and 345182 Cyp rodinil. Section 3 Requ ests for Uses on Tomato , Avocado , H e rb s, Root Vegetables, Leaves of Root and Tuber Vegetables , Lemon, Lime, C ucurbits, Kiwifruit , Green and Dry Bulb Onions, and Strawberries. R egistrant's Response to Condit io na l R egistrat ion on Carrots and Brass ica Vegetables and Livestock Feeding Study. Summary o f Analytical Chemistry and Re s idu e Data
. W
. Cutchin W. Cutchin/B. Madden 06 1 04 1 08 4716110 1-47161107 and 47169305-47169311



### Page 10 of l 7Cyprodinil DP Number: Subject:
From: To: Dated: MRIO(s): DP Number: Subject:

From: To: Dated: MRID(s): OP Number: Subject: From: To: Dated: MRlD(s): DP Numbers: Subject: From: To: Dated: MRJD(s): DP Numbers : Subject: From: To: Dated: MRIO(s):
DP umber: Subject: From: To: Dated: MRJD( s): OP Number: Subject: From: To: Dated: MRJO(s): Summary of Analytical Chemistry and Residue Data DP # : 425723 326346 Regisrration: I 00-953; PP # 8E05012; Cyprodinil on Onions. Review of R evised Label , Field Accumulation in Rotational Crops, Storage S tabili ty , and Analytical Methods Data Requested as Conditions of R egis tration. W. Wassell L. Jones/M. Waller I0/ 18/ 06 46078901,46078903,46 165901 288706 , 288708
. 288710, and 288773 Cyprodinil (PC Code 288202). Section 3 Registration for Application of Cyprodinil to Lychee, Longan, Spanish Lime, Rambutan, and Pulasan (IO #

- 2E06447); Brassica L eafy Greens C r op Subgroup, Head and Stem Bra ss ica Crop Subgroup, and Turnip Greens (ID #

- 2£06485); Carrot (ID #

- 2E0646 I); and Herb Crop Subgroup ( IO #

- 3E06529). Summary of Re sidue Chem is try Data. T. Bloem R. Forrest 07 /24/ 03 45682401 , 45721502 , 45726101,45726102 , 45795301 , 45795302 , and45839801 257898 PP # 8£05012. Cyprod inil in/on Strawberries and Bulb Vegetables (Crop Group 3). Evaluation of Residue Data and Analytical Methods. S. Levy R. Forrest/S. Brothers 02 1 08 1 00 446 15602 , 4461560 I, 448673 12 , 448673 14 243198 Cyprodinil. HED Metabolism Assessment Review Committee Meeti ng of02/I0/ 98. G. Kramer HEO MARC Members 03 / 11 / 98 None 233561,233562.233928 , 233182 , 239674 , and236086 PP# 6F04656. New Chemical- Cyprodinil (i.e., Vangard ®) in / on Stone Fruit , Pome Fruit , AIm ond s and Grapes. Evaluation of Re si du e Data and Analytical Methods. G. Kramer M. Wallcr/T. Ellwanger 02 1 20 1 98 4418640 I , 44186404 and 44186410 thru 44186420; 43908402 , 43908403 and 43908438 thru 43908445; 4438260 I ; and 4427540 I and 44275402 219794 PP # s 5G04553. New Chemical

- Cy prodinil and Propiconazole in or on Stone Fruit. Evaluation of Re s idue Data and Ana l ytical Method s. G. Kramer C. Welch / K. Whitby 02/ 13 / 96 4370900 I through 43709004, 43709048 through 43709055, and 43737603

one Multiresidue Method Testing Data for Cyprodinil and CGA-232449 G. Kramer 8. McMahon, FDA 11 1 28 1 95 43709050 

### Page 11 of 17C y prod inil Summary of An a l y tic a l Ch e mi s try and Re s idu e Data


### Att ac hm e n t s : Ap pe ndi x I

- Inte rn at ional To lerances A pp e ndi x 

### IT

- T ol e rance Assess ment Calculati o n s 

### F . DO CU ME N T TRA C KIN G R.0 1 : E . R ea v e s 3 / 30 / 1 6 Peti t ion Nu m ber: 4F8333 DP # : 425723 PC Co d e : 2 88 2 0 2 Templat e Vcrsi o n Sc pt c mber 2005



### Page 12o f17 DP# : 425723Cyprodinil Summary of Analytical C hemi stry and Re s idu e Data DP # : 425723 

### Appendix I. International To l e rance s Cy prodin il 

### (PC Code 288202: ) Summary of US a n d International T olerances and Maximum Re s idue Limits R esidue Definition: 

## us Canada Mexico 2 Codex 40 CFR 180.53 2: 4 -c yclopropy l- 6-methyl

- Cyprodini l N-phen y l-2- The res idue is Plant : Cy prodinil (4 -cyclop r opyl

-6-m eth y l

-N

- py rimidinamin e fat so luble. phen y l- 2 -py rimidinamine ). Comm od ity ' Toleran ce (ppm) / Maximum R es idue limit**kf!.)** 

## us Canada M ex ic o 2 Codex Nut, r r ee, group 14-12; except almor d0.04 e xc ept pi s tachio

Comp leted: 1 Includ es only commo diti es of interes t for thi s acti on. T o le ranc e va lues should be the HED re commen dati ons and not tho se propo sed by the ap plicant. 2 Me x ico adopts US toleran ces and/or Co dex MRL s for it s ex port purposes.



### Page 1 3of 1 7Cyprodini l Summary of Analytica l Chemistry and R esidue Data DP # : 425723 

### A pp e ndix II. Tol e ran c e Assess m e nt Ca lcul a ti on s. For each of the crops listed below , the 

### OECD MRL Calculator User Guide (S OP) , alo n g with the to lerance s preads h ee t , was u sed for calculating r ecommended to le rance s . As specified in the SO P , the tolerance calcu l ation is in the reg ion of the 95 111 

### percentile of the underly in g res idue distribution , and is more like ly to overestimate rather than undere stimate the 95 111 

### pe rcentil e. The rounding procedures spec ifi ed in the SOP were also u sed. The OECD tolerance sp readsheet does not require the use of maximum-likelihood es tim a tion ( MLE) procedures fo r va lu es < LOQ. Usi ng the O EC D MRL Calc u lato r, th e reco mm e nded tol e ranc es are 0.04 pp m for N ut, tree , gro up 

### 1 4 -1 2; except a lm ond , except pi s tachio

Page 14of17Cy pro d inil S umm ary of An al y tic a l C h emi stry and R es idu e Data Cyprodinil Tree Nuts

- Pecan Nutmeat 

## us 1.3 lb ai/A; 14 day PHI Total number of data ( n ) Percentage of censored data N

umber of non-censored data Lowest residue Highest res i due Median residue Mean Standard deviation (SD) Correction factor fo r censoring ( CF ) Proposed MRL estimate

- H i ghest residue

- Mean + 4 SD

- CF x 3 M e an Unrounded MRL Rounded MRL**~igh uncerta~~ty**  of MRL estimate
. [Small dataset]
Res i dues (mg / kg) n 

### < 0
. 01 2 0
. 0104 1 0
. 0109 1 0
. 0254 1



### P age 1 5o f17 5 40%

3 0
. 010 0
. 025 0
. 010 0
. 013 0
. 007 0
. 733

0
. 025 0
. 040 0
. 029 0
. 040 0.04 DP # : 42 5 723C yprodinil Summ ary of An a l ytical Ch e mi stry a nd R es idu e Data Cyprodinil Tree Nuts

- Almond nutmeat 

### us 1.3 lb ai/A; 14 day PHI Total number of data (n) Percentage of censored data Number of non-censored data Lowest residue Highest residue Median residue Mean Standard deviation (SD) Correction factor for censoring (CF) Proposed MRL est i mate - H i ghest residue

- Mean + 4 SD

- CF x 3 Mean Unr o unded MRL Rounded MRL

High uncertainty of MRL estimate
. [Small dataset]
Residues (mg/kg) n < 0
. 01 2 0
. 011 1 0
. 013 1



### Page 1 6of 1 7 4 50 %

2 0
. 010 0
. 013 0
. 011 0
. 011 0
. 001 0
. 667

0
. 013 0
. 017 0
. 022 0
. 022 0.03 DP# : 42 572 3Cy prodinil Summary of Anal ytical Chemistry and R es idu e Data Cyprodinil Tree Nuts

- Almond Hulls 

### us 1.3 lb ai/A; 14 day PHI Total number of data (n) Percentage of censored data Number of non-censored data Lowest residue Highest residue Median residue Mean Standard deviation (SD) Correction factor for censoring (CF) Proposed MRL estimate

- Highest residue

- Mean + 4 SD

- CF x 3 Mean Unrounded MRL Rounded MRL

Hi gh uncertainty o f 

### MRL es t i m ate . [Smal.i. dataset]
Residues (mg/kg) n 0
. 707 1 2
. 28 1 3
. 72 1 5
. 4 8 1



### Page 17of17 4 0% 4 0
. 707 5
. 48 0 3
. 000 3
. 047 2
. 036 1
. 000

5
. 4 8 0 11
. 191 9
. 140 11
. 19 1 15 DP #: 425723

# Volume 3 AnnexB



# Cyprodinil

B.S M ET HOD S O F ANALYS I S
B.5.2 ANALYTICAL METHODS FOR THE DETE RMINATION OF RESIDUES (ALL COM PO NENTS I NCLU DE D I N THE RE S ID UE DEFI NIT IO N PROPO SE D)Cyprod inil [P C Code 288202]/Syngenta Crop Protecti o n , LLC [CGA2 l 94 l 7] Note: This Data Eva luation Record (DER) was originally prepared under contract by Versar. In c. (68 50 Versar Center. Sprin gfie ld. VA 22 1 5 1 ; submitted 4/ 10 / 1 5). T he DER h as been reviewed by HED and revised t o renect current Office of Pesticide Programs (O PP ) policies.

Table B.5.2-1. Overview o f t h e A n a lyt ical M ethod s for the De termination of Cyprodinil R esid ue s. Data Matrix Ana l ytcs Requirement Enforceme n t Plant Cyprodinil Met hod- Plant commodi tie s Commodities
Data-Gatherin g Pome and s tone. Cyprodinil Method

- Pl ant fruits. tree nuts. Commodities grape Bras sica Cyprodinil vegetables. carrot, tomato. avocado, parsley,

radish. lemon. kiwifruit Cucurbit Cyprodinil vegetables.

lettuce Spinach. pepper. Cyprodinil lemon Celery Cyprodinil C rops and tree Cy prodinil nuts
ILVof Enforcement Method

- Plant Commodities R adiovalidation Apple leaves. Cyprodinil of Methods

- tomato Plant Commodit ies Enforcemen t Lives tock Cy prodinil and Method- commodities CGA -304075 Livestock Co mm od iti es Data-Gatherin g Ruminant milk Cy prodinil and Method- and tissues CGA-304075 Livestock Commodi ti es ILV of EnforcementMethodLive s tock Commodities Radi ovali dation of Methods

- Lives tock Commodities EPA MRlD #s: 49470601and49470602 PMRA # of document: Not available Method Type Limit of Quantitation Reference ( ppm ) llPLC ! UV 0.0 1- 0.05 MRIDs 4438260 1. (AG

- 63 1
. J\G- 4 3709052 63 1 A. AG63 I B: fonnerly REM141.01)

llPLC ! UV 0.0 1-0 .05 MR ID s 43908445
. (AG

-631) 4418 6 417.43737603. 44186420 .4 3908444
. 44 1 864 1 8 HPLC/ UV 0.0 1- 0.05 MRIOs 47 1 693 1 0- 11. (AG

- 6318) 47161101-07. 47417703

llPL C!MS 0.01 (22 1 3-0 1 ) LC 1 IS !M 0.0 1-0.02 MRIDs 484374 01 -03. (AG63 1B: 4847850 1 modified) LC ! MS ! MS 0.05 (AG

- 5978) LC!MS / M S 0.0 1 Study No. TK002 I 500 (G RMO I 0.02A) MRIDs 49470601. 494 70602 PMRA #Not available No t avai lab l e

REM 1 41.0 N/J\ MRID 43908440

ll PLC/ MS 0.0 1 MR IOs 44382601, (GRMO IO .O IA) 43709052.47169305

HPLC ! UV 0
. 01 MRIO 43908443 (AG

-635) HPLC/ M 0.0 1 MRIO 47169309 (G RMOJO .O I A) Not avai l able

ot available

Page 2 of7Cyprodi nil [ PC Code 2 88202) /Sy ngenta C rop Protection , L LC [CGA2 l 94 l 7] T ab le B .5.2- 1. Ove r v iew of t he A n a l y ti ca l M e th o d s fo r th e Dete rm i n at ion o f Cy pr od inil R es idu es. Data Matrix Ana l ytes Meth od Type Limit of Quantitation Reference Requirement (ppm) Multiresidue Apple Cy prodinil and its FDA-Pes ti cide 0.50 MRID 43709050 Method Testing metabolite CGA

- Analytical 232449 Methods MultiResidue test in g program T ab le B .5.2-2. C h e mi ca l Structur es o f A na l ytes Ad d resse d by Meth o d s fo r t h e A n a lys is of Cy pro dinil. Method ID Chemical Name Chemical Structure HPLCIUV: AG

- 63 I. AG-63 I A. AG-631 B HPLC/MS: 2213

- 01 LC/MS/MS: AG-5978 AG

- 631 B modified GRMO I0.02A HPLCIMS: (GRMOIO.O IA) HPL CIUV: (AG

- 635) Commo n name: Cyprodinil S y n ge nta code: CGA219417 C h emica l na me: 2

- pyrimidinamine. 4-cyclopropy l- 6

- methyl-
.\ '

- phenylCommo n name : CGA-304075 C h e mica l n a me: 4 -[ (4-cyclopropyl6

- meth y l-2

- 2-py rimidinyl)ami no]- phen ol 

### B.S
. 2
. 1 A n a ly ti ca l Meth o d s for P la n t Matrices (A nn ex II A 4.3, A nn ex III A 5
. 3) 

### B
. 5.2
. 1. 1 Not app li cab l e 

### B.5. 2 .1.2 Doc um e n t ID : R e p o rt:

G uid e li nes: Post-Reg is t ra ti on Me th o d (E n force m e nt )

Pre-Re gi s t r ati on M eth od (D a t a-Gath erin g) MRlD Nos. 49470601 and 494 70602 PMRA No. Not avai lable 4 9 470601 Lin, K. (20 11 ) Cyprodin il. Vali da t i on of Analyti cal Method GRM010.02A fo r the D e t e rmin a tion of Residues of Cy prodinil in Crops and Tree N uts by LC

- MS/MS. F inal R e port. Report N o. TK0021500. U npubli s hed s tud y prepared by Syn ge nta Crop Protection , LLC. 66 p. 49470602 Lin , K
. and Manuli , M. (20 11 ) Cyprodini l. Analytical Me th od for the Determination of Residu es ofC y prodinil in Crops and Tree N ut s by LC-MS / MS. Method. R eport Nos. GRMO I 0.02A , T K002 l 500. Unp ubli s h e d study prepared by Syngenta Crop Pro tec ti on, LLC. 36 p. EPA OCSPP Harmoni zed T est Guidelin e 860 .13 40 Residue Analytica l Me th od {A ugu st 1996) PMRA Regulatory Dir ec tiv e D IR98-0 2

- R es idue Che mi s try Guidelines ,
EPA M RID #s : 4947060 1 and 49470602 PMRA #o f document: Not avai labl e Page3of7Cyprodinil [PC Code 288202) /Syngenta Crop Protection , LLC [CGA2194 l 7} 

### Section 3

- Residue Analytical Method EU SANCO 825 / 00/rev. 7 ( 17/ 3/ 04) OECD Guidance Document on Pesticide Residue Analytical Methods GLP C ompliance: 

### No deviations from regul atory requirements were reported which would have an impact on the validity of the study. Acce ptab ility: 

### The study is considered scientifi cally acceptable. The acceptability of this st

ud y for regulatory purposes is addressed in the fort coming U
. S. EPA Residue Chemistry Summary D oc t , D 3. Eva luator: 

### Thurston G. Morton, Chemist Registration Action Bran ch 4 Health Effects Division ( HED) (7509 P)
EXECUT I VE SUMMARY 

### Syngenta ha s s ubmitted a hi g h performance liquid chromatography method with tandem mass spectrometry detection (LC/ MS/ MS) , method GRM010.02A, for analysis ofresidues of cyprodinil in/on a variety of crops including tree nuts. The method is a modified vers ion of method REM141.01, the original e nfor cement method fo r cyprodinil. A complete method description (M RlD 49470602) and supporting method validation data (M RID 49470601) have been submitted. The method was used for analysis of residues of cyprodinil in the tree nut crop field trial s tudi es submitted under the current action (refer to 49470603.der; B.7. 6. 1.1). Briefly, samples are extracted w ith methanol:water (80:20 , v:v) for 1 hour. For tree nuts on ly, the ex tract i s then acidified to pH 2-3 with the addition of concentrated HCl. For all crops, the extract is centrifuged then filtered , and an aliquot is combined with 0.1 % ammonium acetate and applied to a Waters H LB solid phase extraction (SPE) cartridge. Residues are eluted with 0.1 % ammonium acetate:acetoni trile (ACN; 40:60, v:v). The eluate is diluted with 0.1 % ammonium acetate and further diluted with 0.1 % ammonium acetate:ACN (70:30 , v:v) as needed for analysis by LC/MS/MS. The method monitors two ion transitions for cyprodinil 

### (m lz 226 --> 

### 93 for quantitation and 

### rn /

z 226 --> 

### 77 for confi rm ation). The limit of quantitation (LOQ; determined as the lowest level of method validation, LLMV) is 0.01 ppm. The limit of detection as determined by the lowest standard injection (s i gnal:n oise >3: I ) was reported to be 0.1 pg. The method was adequately validated for the quant it ation and confirmat ion ion transitions using samp les of almond nutmeat and hulls, apple, tomato, and wheat forage , hay, and grain fortified with cyprod inil at 0.0 l and 0.1 ppm. Recoveries were ge nerally within th e acceptable range of 70-120%
. Becau se the method monitors multiple ion transitions for determination of cyprodinil, no confirmatory procedures are needed. An Ind ependent Laboratory Validation (ILV) of the method was not submitted. Provided the method i s not proposed for enforcement, no 

### IL V is necessary. No radiovalidation d ata have been submitted for method GRMO l 0.02A. The extraction procedures used for this method are the same as those used for the established enforcement E PA MRlD # s: 49470601and49470602 PMRA # of document: Not availabl e Pag e 4 of7Cyprod inil [PC Co de 288202) /Synge nt a C rop Protection , LLC [CGA2 l 9417) 

### methodology, for which radiovalidation data were previously submitted and reviewed (refer to 

### DP #s 23356 1 , e tc ., 2/ 20/ 98, G
. Kram er); th e refore, no additional data are req u i red
. I. 

### Prin ci pl e o f th e Meth od : G RM010
. 02 A

T a bl e B.5.2. 1.2- 1. S umm ary Pa r a m e t ers fo r th e Pr e- R eg is t r at i on A n a ly ti ca l M e th od Use d for t h e Analys is o f C y pro d inil Re s id u e s in C r o p s a n d T r ee N u t s . Method ID GRMO I 0.02A Anal y tc( s) Cy prodinil Extraction solvent Wld Briefl y . sa mples are ex t racted with methanol:water (80:20. v:v) for I hour. For tree nuts o nl y, the technique extract i s th en acidified to pl I 2-3 wi th the addition of concentrated I ! Cl. For all c r ops. the extract is centrifu ge d then liltcrcd. Clean -u p strateg i cs An aliqu ot of the extract is combined with 0. 1 % ammonium acetate and applied to a Waters HLB SPE cartridge. R esidues are eluted with 0. 1 % ammonium acetate:ACN ( 4 0:60, v:v). The eluate is dil ut ed with 0. 1 % ammonium ace tate and further diluted with 0. 1% ammonium ace tate:ACN (70:30, v:v) as need ed for analysi s by L C

/MS/ MS. In strum e nt and Detector L C/MS/MS us ing a Supelco Ascentis® Ex pre ss C s column and a grad ient m ob ile phase of water and meth a no l with M S/MS detection us in g multiple reaction monitoring ( MRM ) operated in th e posit ive ion mode. The followi ng i o n tran s ition s are m onito r ed for determin atio n of cyprodini l: m

/: 226 -+ 93 for quantitation and m /: 226

- 77 for confinnation Standardizati on m e thod Ex ternal standardiz.ati on us in g calibra ti on standards to ge nerate a five -p oint calibration curve over the ran ge of 0.0 1- 0.20 ng/ mL. Stabi lity o f s td so lution s Stab ility o f s t andard so luti on s wa s not report ed. Final ex tract s i n 0. 1 % ammonium acetat e:ACN (70: 30. v:v) were stable when s tored refri gera ted (-4 ° C) fo r at le ast 6 -12 days. Reten tion tim es 4.7 minut es. 

### II
. Spec ifici ty The LC/MS/ MS meth od is hi g h l y se lective for both the qu antitati o n and confirmation of cyprodinil. Ana l ysis of contro l sampl es resulted in no significant s ignals at the ex pecte d retention tim es of the analytes. The petitioner subm itted data indicating tha t no interference was observed at > 30% LOQ at or nea r the re te nt ion t ime o f cyprod inil in any of the untreated crop components. U nan1b iguous id e ntific ation is e n s ured b y monitoring two MS/MS transitions : Cyprodinil 

### m /

z 226-+ 93 ( qu antitation ) 

### m

/z 226 -+ 77 (confirmation) Becau se the m e thod monitors multipl e ion tran s itions for the determination of residues of cyprodinil, no co nfirm a tory procedure s are nee d e d
. 

### III. Li n ea ri ty The linearity of detect o r respon se w a s eva luated using solvent s tandard solution s. Calibration c u rves were calculated b y line ar regression analysis. F or the eq u ati o n w hi c h de scr ib es th e det ec to r re spo n se as a function of the s tandard concentration , calibration curves resulting from the inj ec tion of a minimum of five s tand ards ove r the concentration range o f 0
. 01-0.20 ng/ mL demon s trated linearity w ith coefficient s of determination 

### (r2) of at lea st 0.9992.

EPA MRJD #s: 4947060 1 a nd 49470602 PMRA # of d ocument: Not avai lable Pa ge 5 of7Cyprodinil [PC Code 288202 ) / Syngenta Crop Protection, LLC [C GA2 I94 l 7) 

### IV. Accuracy (Recovery) and P r ecision (Repeatability) Radi ovalidati o n. No ra dio va lidation data ha ve been s ubmitted for method GRMOI0 .02A. The extraction procedure s used fo r this m e thod are the same as tho se u se d for the estab li shed enforc e ment method o logy, for which ra diovalidation data were prev iou s ly s ubmitte d and re v iewe d (re f e r to DP#s 233561 , etc. , 2/ 20/ 98 , G
. Kram er); therefo re , no a ddition a l data are required. Tab l e B.5.2.1.2

- 2. Radi ova lidation o f the Pre- Regi s tration An a ly tical Method for Plant Matri ces Ma tri x 

## I An a l ytc 

### I Ex t ract ion Method 

### I Radioactive Residue s (ppm) 

### I Extraction Efficiency(%) Not app licable 

### Method va li dation
. The method was adequate ly valid ated for th e quantitation and co nfirm ation ion trans ition s u s in g sam ple s of almond nutm eat and hull s, appl e, tomato , and wheat fora ge, ha y, and grai n fo rtified wit h cyprodinil at 0.0 1 and 1. 0 ppm . Recov eries we re genera ll y w ithin the acc e ptab l e range of 70- 120 %
. Mean re coverie s (and r e lative standard dev iations) for cyprodinil following fortification at 0.0 l and 0.1 ppm, re s p ec tivel y, 

### in all matrices w e re : 73-86% ( 1 .8- 8.4 %) and 80-88% (2.0 -11 %) fo r the quantitation tran s i t io n and 79

- 88% (2.8 -8.0 %) and 78 -86 % (1.8- 12%) fo r the confi rmati on tran s iti on. Rep eatab ility data we re ge nerate d from five samp le s fortified at the LOQ an d fi ve samp les fortifi e d at lOx LOQ for each matrix. The relati ve standard deviations ( RSDs) obtained for each fortification leve l we re S l2 %. Recov e r y and repeatability data ar e pre se nte d in Table B.5 .2. 1.2- 3 , below. Tabl e B.5.2.1.2-3. Acc ur acy a nd Precision Data for Method GRM0 10 .02A. Analytc Matrix Forti fication Level (ppm) Cy prod in ii Almond 0.0 1 m'.: 226-93 nutmeat 0.10 (quan t itation) Almond hulls 0.0 1 0.10 Apple 0.0 1 0.10 Tomato 0.0 1 

### o. 1 0 Wheat forage 0.01 0. 1 0 Wheat hay 0.01 0.10 Wheat gra in 0.0 1 0. 1 0

EPA MRlD #s: 49470601 and 49470602 PMRA # of document: Not available Concurrent Recovery (%) Individua l Mean 84.82.85.83. 77 82 93. 88. 72. 83. 89 85 76. 69. 73. 72. 77 73 87.94, 78. 79. 76 83 90.86. 82.86. 86 86 88. 86. 70. 71. 87 80 83, 82. 83. 86. 83 83 81. 83. 81. 94. 86 85 81. 98. 83. 82. 82 85 94.85,87. 84. 9 1 88 79.80,83,80, 79 80 79.82.83.82.83 82 76, 80. 83. 85. 7 I 79 86. 86, 77. 8 I
. 72 80 R SD Range (%) 77-85 3.8 72-93 9.5 69-77 4.4 76-94 9.1 82-90 3.3 70-88 11 82-86 1.8 8 1- 94 6.4 81-98 8.4 84-94 4 .8 79-83 2.0 79 -83 2.0 7 1-8 5 7. I 72 -8 6 7 .5

Pa ge 6 of7Cy pro dinil [PC C od e 2 882 0 2 ] / S y n ge nta C rop Pro tection , LL C [C G A2 I94 J 7 )
T a ble B .5.2. 1.2-3
. Ac curac y and Pr e cision Dat a for Meth o d GRMOI0 .0 2A. /\nalyte Mat rix Fortifica t ion Concurrent R ecovery (%) Leve l ( ppm ) I nd iv id ua l Mea n Ra nge Cyp rod ini l A lmo nd 0. 0 1 8 8
. 88
. 8 1
. 83. 86 85 8 1-8 8 Ill= 226-> 77 nutmeat 0. 1 0 9 1. 87. 8 1. 8 -L 88 86 8 1-91 (confirmation) Al m o nd h ull s 0.0 1 76.82. 75.80,84 7 9 75 -8 4 0. 10 8 3. 84
. 8 1 , 7 4
. 79 8 0 7 4-84 App le 0.0 1 8 8
. 80.89 .8 7. 8 4 86 80

- 89 0. 1 0 9 1. 87. 7 5 , 76. 99 86 75

- 99 Tomato 0.0 1 86,87,92. 86. 88 88 86

- 92 0
. 1 0 9 1 , 7 8
. 8 1. 89
. 8 0 84 78- 9 1 Wh eat forage 0.0 1 8 5.96.83 .8 2. 78 85 78-96 0. 1 0 87.90.88
. 80.87 86 80

- 90 Wheat hay 0.0 1 78 , 8 .t . 77. 8 0. 82 80 77

- 84 0. 10 8 7.8 4 , 88 , 8 7. 8 6 86 8 4-88 Wh ea t g rai n 0.0 1 8 4.82. 75 . 8 4. 73 80 73

- 84 0. 10 79.83. 76.80. 7 1 78 7 1-83 

### V. Limit of Q u antitation

T a b le B
. 5 .2. 1. 2 -4. Summ ary o f D e t ection a nd Qu a ntitati o n Limit s for Method G RM010
. 02A
. /\ na lyte 

## I LO D ( ppm ) 1 

### I Cy pro d in il 

## I 0. 1 pg 

### I 1 LOO= limit of detection. determined based on the lowest standard injection with signal:noise > 3: I
. 2 LOQ =limit of quantitation. defi n ed as th e lowest level of met hod va l idat i on: LLMV). 

### VI. Conclusions LOQ ( ppm ) 2 0.0 1 R SD (%) 3.7 .t .4 4 .8 4 .9 4.3 1 2 2.8 6. 9 8.0 4.4 3.6 1.8 6.6 5.8



### Th e L C /MS / MS meth o d GRM O I 0.0 2 A was adequ a t e ly v al idate d for d e te rm inin g r es idue s of cy pro di n il i n c ro p s i nc ludin g tree nut s . T he vali da t e d 

### L OQ i s 0.0 1 ppm. A confi rmato ry m e thod i s not required becau se the m e tho d mo n ito rs two io n trans it io n s . 

### B.5.2.2
No t appli c abl e 

### B.5.2.3. N ot appli c abl e 

### Analytical Method s for Foodstuff of Anima l Origi n (Livestock Matrice s; Annex HA 4.3 , Annex IHA 5
. 3)

Multiresidue Method s

E PA M RJ D # s: 4947060 1 a nd 494 7 0602 PMRA #of doc um e nt: No t av ail a bl e P age 7 of 7Cyprodinil [PC Code 28 8202] / Syngenta Crop Protec tion , LLC [CGA2 l 9417] 

### B.7.6 Residues R es ulting from S up erv i se d Trials (A nn ex II A 6 . 3; Annex IHA 8.3) B.7.6.1 Residues in Ta r ge t C rop s B.7.6.1.1 Tree N uts Document ID : MRID No. 49470603 PMRA No. Not available Report: Mazlo. 

### J. (2 013) Dif e noconazole/ Cyprodinil EW (Al600lA)

- Magnitude of the Re s idues of Cy prodinil in or on Almonds and Pecan s as Representative Commodities ofTree Nuts, Group 14. USA 2012
. Final Report. Report Numbers: TKO l 08966 and 68387. Unp ubli shed stud y prepar ed by Syngenta Crop P rotection, LLC. 128 p. G uid e lin es: EP A OCS PP Harmonized Test Guideline 860
. 1500 Crop Field Trials (Augu st 1996) PMRA Regulatory Directive DIR 98-02- Residue Chemistry Guide li nes , Section 9

- Crop Fie ld Trials PMRA Reg ulatory Directive 

### 0 IR2 0 I 0-05

- R ev is ions to the Residue Chemi s try Crop Fie ld Trial Require ments OECD Guideline 509 Crop Field Trial (September 2009) GLP Comp lianc e: No deviations from regulatory requirements were reported which would have an impact on th e validity of the study. Acce pta bili ty: The st ud y is considered scientifically acceptable. The acceptabil ity of this study for regulatory purposes i s a ddressed in the forthcoming U.S. EPA Re sidue C he mi stry Summary

### Do~ct D 5723. Eva lu ator: Thurston G. Morton , Chemist Regi stration Action Branch 4 Health E ffects Di v is ion (HED) (7509P) Note : T hi s Data Eva lu ation R eco rd (D E R) was originall y prepared und e r co ntract by Vcrsar, In c. (6850 Vcrsa r Cen ter. Springfie l d, VA 22151 ; s ubmit1ed 4 / 1

0/15). The DER has been reviewed by 1-! ED and r ev ised to reflect current Oftice of Pe sticide Programs (OP P) policies. 

### EXECUTIVE SUMMARY Syngenta Crop Protection ha s s ubmitted field trial data for cyprodinil on tree nut s. Five pecan field trial s we re conducted in the U nited States during the 2011 growing season i n th e No rth American Free Trade Agreement (NAFT A) Growing Zo nes 2 ( GA ; 2 trials) , 4 (LA; 1 trial) , 6 (OK ; l trial) , 8 (OK; I trial) , and four almond trials were conduc t ed in Zone 10 (CA; 4 trials). Th e above field trial count ex cludes one CA almond field trial which the petition e r excluded from the study because the seaso nal application rate exceeded the targ et rate. Thi s trial is not a ddresse d furth e r herein. Eac h trial site consisted of one untreated plot and one treated plot reflecting four foliar broadcast applications mad e with the 2.09 lb ai/gal oil in water emulsion (EW) formulat ion of cyp rodinil (Inspire Supe r® Fungicide), a multiple ac ti ve ingredi e nt (MAI) formulation which also contains EPA MR I D # : 49470603 PMRA # of document: Not availabl e Page I of8Cyprodinil [PC Co de 288202) /Syngenta Crop Protec tion , LLC [CGA2194 I7] 

### difenoconazole at 0.73 lb ai / gal. Data and information pertaini ng to dife noco nazole are not addressed further herein. Applications were made at a rate of 0.317-0.338 lb ai / A/ap plicati on at re treat me nt intervals ( RT i s) of 12-15 day s using grou nd eq uipm ent in spray volumes of 69-208 gal / A for a total app li cati o n rate of 1 .30- 1 .34 lb ai / A. A nonionic surfac tan t (N IS) or crop oi l concentrate (COC) was added to the spray mixture for eac h application. Samples of pecan (nutmeat) and al mond ( nutmeat and hulls) we re harvested at pre harve st intervals ( PHl s) of 13-14 day s. Additional a lm ond ( nu tmeat and hull) samples were co ll ected from one trial at PHis of 0, 5, 9 , and 19 day s to ge nerate residue dec li ne data. Samples were maintained frozen at the testing facilities , during s hipping , and were sto red frozen at the analytical laboratory until analysis
. The maximum s torage interval for samp le s between h arves t and extrac ti on was 298 days (9.8 months) for pecan (nutmeat) and alm ond ( nutm eat and hull s)
. Samples were ana lyzed with in 14 days of extract io n . Th e petitioner indicated that storage stability data were available for tree nuts (Sy nge nta Study No. T003062-07); howeve r, these data do not appear to have been reviewed by the agency. Acceptable storage stabi li ty data are avai l able indicating th at residues of cyprod inil are s table during frozen storage for up to 2 years in/o n a variety of crops includin g w heat ear and s ta lk (DP#s 23356 1 , e t c., 2/20/ 98 , G. Kra mer). These data are acc eptab l e to s upport storage co ndition s and durations of samp les fro m the submitted field trials. Samp l es we re a na lyzed fo r residues of cyprodinil using high p erformanc e liquid c hrom atograp hy w i th tandem ma ss spectro metric detection (LC/MS/MS) using method 

### GRMOO 10.02A, with m i nor modificati ons. Acceptabl e method validat ion and concurrent recoveries were reported for samp les fortified with cy prodinil at 0.01-10 ppm , th us va li datin g th e method. The limit of quantitation (LOQ; determin ed as the l owest leve l of met ho d validat io n , LL MV) was 0
. 0 l 0 ppm . Th e fort ific ation levels used in concurre n t metho d recove ry were adeq uate to bracket expecte d residue level s. Concurr e nt recoveries were corrected for apparent r esi dues in co n tro l s (residues in contro ls we re below the LOQ); residu es in the treated sample s were not corrected for appare n t residues in controls. In tree nut s h arvested at a PHI of 13-14 days fo ll owing the l ast of four foliar broadcast applications of a 2.09 lb ai/ga l EW formulation at a total rate of 1.30-1.34 lb ai / A , individ u al sample (and per-trial average) re sidues of cyprodinil were < 0.010-0.0408 (<0.0 I0- < 0
. 0254) ppm i n/o n pecan (n utm eat), < 0.010-0.0 1 46 ( < 0.0 1 0-0.0 1 31) pp m in/on a lm ond (n ut meat), and 0.707- 6.46 (0.707-5.48) pp m in/ o n a lmo nd (h ull s). In the one resid ue decl in e trial. residues of cypro dinil generall y declined in/on almond nutm eat and hulls with increas in g PHI. I. 

### MATERIALS AND METHODS A. MAT E RIALS

T a bl e B
. 7
. 6.1.1

- 1. Nomenc l atur e for C y p rod inil C omm o n n a m e Cy prod inil Id e ntity 2-py rimidinamine. 4-cyclopropyl

-6

- mc1hy l- .V

- pheny lCAS n o. 121552-61-2 EPA MR.JD #: 49470603 PM RA # of document: Not available Page 2 of8Cyprodini l [PC Code 288202) / Synge nta Crop Protection, LLC [CGA2 I94 I 7) Tab le B.7.6.1.J-l. Nomenclature for Cyprodinil Compa ny expe rim en t a l name I CGA2 1 94 17 Other sy no ny m s ( if a 1 >p licab le) 

### INo t app li cab l e H 

# ()NYN"
N _,,,-:::. C H 3 

### B. Study De sig n 1. 

### Test P r oced u re Five res idue trial s were co nducted on pecan s and four res idue trial s were conducted on almond s in the U nited States re fl ec ting foliar broadcas t applications of the 2.09 lb ai / ga l EW formulation ( In s pire Super® Fun g icid e) of cyprodinil durin g th e 20 11 growing season . F ie ld trial locations 

### by NAFTA growing zo ne a re s ummarized in Table B.7.6.1.1-2. Table B
. 7
. 6 .1.1 -2. T ri a l N um b e r s a n d Geograp hi ca l Lo catio n s. Crop No. NAFTA Growing Zone Total Trials I 2 3 4 5 6 7 8 9 10 11 12 A lm onds S u b. 4 4 Rcq
. 1 5 5 Pecan s Sub. 2 I I I 5 Req. 1 2 I I I 5 1 As per OCS PP 860.15 00, Tables 2 and 5 for almond and pecan as rep r esentative commoditie s of the tree nut group. 

### Locations and detailed u se patterns for the trials are provided in Table B.7.6.1.1-3.

Tab l e B.7.6.1.1-3
. S tud y Use P attern. Location: City, End -u se Method of Application: Vo lum e Rate per R etr

eaunent Total R ate Surfactant/ S tate : Year (T rial Product 1 Timing of Application (gal/A) Application I nterval ( lb ai/ A) Adjuvant 2 ID ) ( lb ai /A) (days) Pecan trial s Chula. GA: 2011 2.09 lb I
. Foliar broadcast: BB C H 80 207.75 0.323 

## -- 1.31 N IS (T K 0059529

-0 I ) ai/gal 2. Fo liar broadcast: BBCl

-1 80 135.50 0.330 13 N IS 3. Foliar broadcast: BBC I I 81 137.69 0.327 15 NIS 4. Fo liar broadcast: BBCl

-1 85 130.66 0.329 13 NIS Pineview. GA: 2.09 l b I
. Fo li ar broadcast: BB C l-I 80 136.40 0.331 

## -- 1.32 

## coc 20 11 ai /g a l 2. Foliar broadcast: BBCH 83 1 27.3 1 0
. 329 15 

## coc (TK0059529

-02) 3. Foliar broadcast: BBCH 85 128.99 0.331 13 

## coc 4. Fo liar broadcast: BBCH 85 123 .43 0.333 14 

## coc

EPA MR.ID # : 4947060 3 PMR.A # of document: Not ava ilabl e Page 3 of8Cyp r o d inil [ PC Code 288202 )/ Synge nt a Crop P rotection, LLC [CGA2 I 94 17) Table B.7.6.1.1-3. St ud y Use P atte rn . Loca ti o n: C ity, End

- use M ethod of Appli ca t ion; Vo lume S ta te: Y ea r (T ri a l P rod uc t ' Timin g o f Appli cat io n (gal/A) ID ) A l

exandr i a . LA: 2.09 lb I
. Fo li ar broa dcast: BBC H 85 70.80 20 11 ai/gal (hard dough) (TK0059529

- 03) 2. foliar broadcast: BBCI I 85

- 88 79.87 (approximate l y 10% beginning s huck split) 3. Foliar broadcast: BBC H 85

- 88 80.89 (approximately 25% beginning shuck split) 4. Fo li a r b r oad cast: B BC I I 93 83.46 (p rog ress ive s hu ck sp l it) M ad ill
. O K : 2011 2.09 l b I. fo lia r broa dc as t : BB C ll 80 76.97 (TK00 5 9 52 9

- 04) ai/ ga l 2. Fo li ar broa dcast: B BC H 85 73.5 1 3. Foliar broadcast: BBC H 89 69. 1 3 4. Foliar broadcast : B B CH 93 74.32 Altus
. OK; 20 11 2.09 lb 1
. Foliar broadcast: 13BCH 79 1 32.83 (TK0059529

- 05) ai /gal 2. Foliar broadcast: BBC I I 85 1 35.58 3. Foliar broadcast : BBC! I 89 1 33.04 4. Fol iar broadcast: BBC H 93 1 35. 1 4 A l

mond trials S t rathm o r e . CA: 2.09 l b I
. Fo li ar broa dcast ; BB C I I 79 20 11 ai/ga l ( fruit at f ull s ize) (T K 0059 529- 07) 2. Fo li ar broa dcast: BBC I I 79 (fru it a t full size) 3. Foliar broadcast : BBCI I 79 (fruit at full size) 4. Foliar broadcast: BBC! I 89 (fruit at full size) Chico. CA: 20 11 2.09 lb I. Foliar broadcast: not spcci lied (TK0059529

- 0 8 ) ai / gal 2. Fo li ar broad cast: no t spccilicd 3. Fo li ar broadcast: no t specified 4
. Fo lia r broa dcast : no t spec ified Di nu ba
. CA : 2.09 lb I
. Fo li a r broa dcas t : B B C H 79 20 11 ai /gal (fru i t at f ull size) (TK0059 52 9

- 09) 2. Foliar broadcast: BBC I I 79 (fruit at full size) 3. Foliar broadcast: BBCH 79 (fruit at full size) 4. Fol i ar broadcast: B BCH 79 (fruit at full size) Ma dera, C A : 2.09 l b I
. Fo li ar b road cast : B B C H 79 2 011 a i / ga l (p re- hull s plit ) (T K 005 9529- I0) 2. F o li ar broa dc ast: BB C I I 79 (pre

- h ull sp li t) 3. Foliar broadcast: BBC H 8 1 (hull split) 4
. Foliar broadcast: BBCH 81 (drying hull)

. . 1 A 2.09 lb a i/ga l EW fonnulauon (Inspire Supe r® fung1c1de)
. 2 NIS = onionic surfactant: COC = Crop oil concentrate.

E PA MRID # : 4 9 470 6 0 3 PMRA #o f do c um e nt : Not ava il a bl e 7 1. 37 7 1 .36 72.76 72.77 149.52 149.47 14 9.5 8 14 9.20 1 54.58 1 84.26 204.87 205.62 82.72 8 1 .77 8 1 .5 1 81.14 R ate p er Applic ati o n

(lb a i / /\) 0.333 0
. 327
0.331
0
. 33 1 0.330 0.3 17 0
. 323 0.327 0.331 0.322 0.328 0
. 323 0. 3 30 0.330 0.33 1 0.330 0.33 1 0.33 1 0
. 33 1 0. 33 0 0.3 28 0.327 0.329 0.329 0
. 338 0. 3 34 0.333 0.33 1 Rc trcatmcn t Tot al R ate S u rfac tant/ Int erva l ( lb ai/A) Ad ju vant 2 ( d ays)



### -- 1.3 2 N IS 1 4 I S
14 I IS
14 N IS



## -- 1.3 0 

## coc 14 

## coc 1 4 

## coc 1 5 

## coc

-- 1.30 N I S 1 4 N IS 15 N IS 1 2 N I S



## - - 1.3 2 N I S 14 N I S 1 4 I S 14 IS



## -- 1.32 

## coc 14 

## coc 14 

## coc 14 

## coc



# -- 1.31 N I S 1 4 IS 1 4 1 1S 1 4 r1s



## -- 1. 3 4 

## coc 14 

## coc 14 

## coc 14 

## coc

P age 4 of 8Cyprodinil [PC Code 288202) /Syngenta C rop Protection , LLC [CGA2 I 9417) 

### Pecan s and a lmo nd s were grow n and maint a ined accord in g to typical agricultural practices. Irri gatio n was used to supp l eme nt rainfall at Trial s 01, 03 , and 07-10. No unusua l weather conditions were reported to have adversely affected crop growth or yields during the study. Sa mp l e Handling and Preparation S in gle untreated and duplicate treate d samples of pecan (nutmeat) a nd a lm ond (nutmeat and hulls) were collected at each trial. Samples we r e harvested at PHls of 13-14 days. Additional almond ( nutmeat and hull ) samples were co ll ec ted from one trial at PHis of 0, 5 , 9, and 19 days to generate residue decline data. Samples were placed in fro ze n sto rage ( < -10 ° C) at the fie ld sites. Samples were shipped frozen v ia free ze r truck or overnight courier within 0

- 38 days of harvest to the analytical l aboratory, Syngenta Crop Protection , LLC (Greensboro, NC). At the analytical laboratory, samp les were homogen ized in the prese nce of dry i ce a nd were stored frozen (-20 ° C) until extraction for analysis. 2 . De s cription of A naly tic a l Procedure s Samples were analyzed for residues of cyprodinil by LC/MS/MS method GRM 00 1 0.02A with minor mod ificat ions. A complete description of the method , including detai ls of minor modifications , was inc luded in the s ubmi ssion. Modifications included the following: m inor materials and instrument changes; removal of acidification step with HC l to adjust pH; and following elution residues were d i luted w ith 0.1 % ammonium ace tate:ACN (90 : 10 , v:v)
. A complete d esc ription and method val idati on data for this method are currently under review under DP# 425723 (refer to 49470601.der in Section B.5. 2). Briefly , samp les of were extra cted with methanol:water (80:20, v:v) for 1 hour. The extract was centrifuged then filtered , and an aliquot was combined with 0.1 % ammon i um acetate and applied to a Water s H LB solid phase extraction (S P E) cartridge. Residues were eluted with 0.1 % ammonium acetate:acetonitrile (ACN; 40:60, v:v)
. The eluate was diluted with 0.1 

### % ammoniwn acetate:ACN (90: 10 , v:v) fo r analysis by LC/ MS/MS. The LOQ (determined as the lowest lev e l of method validati on ; LLMV) was 0.010 ppm . The LO D (l imit of detection) was not reported. 

### II. RESULTS AND DIS CUSS IO N Method perfonnance was eva luated d u ring method validation and by use of concu r rent recove r y samples. For method validation, samples of untreated a lmond (nutmeat and hulls) we re fortified with cyprodinil at 0
. 0 I 

### and 1.0 ppm. For concurrent recovery . samples were fortified with cyprodinil at 0.01 -1. 0 ppm for pecan ( nutmeat s), 0.0 1-0.1 ppm for almond ( nutmeats) , and 0.01- 10 ppm for (almond hulls). Recoveries were within the acceptable range of 70- 120%; therefore , the method was co n sidered va lid for the analysis of cyprodinil r esid ues in/on tree nut matrice s (Table B. 7.6
. 1.1-4)
. The fort ification level s bracke ted the measured residues. Conc urrent recoveries were corrected for apparent residue s in contro ls.

E PA MRJD # : 49470603 PM R A # of docum e nt: Not available Page5of8Cyprodinil [PC Co de 288202]/S y ngenta Crop Protection , LLC [CGA2 I 9417) 

### The detector response was li near (coeffici e nt of determination , 

## r2 2;: 0.9946) w ithin the range of 0.02-0.5 ng/ mL. Re pre se nt ative chromatograms of control sa mples , fortified sam ples , and treated s amp les w ere provided. The control c hromatogram s generally had no peaks of interest above th e chromatographic background. Th e fortified sam pl e chromatogram s contained o nl y the analyte of interest, and p eaks were symmetrical and well defined. Apparent resi dues in control s were below the LOQ ( < 0.010 ppm)
. The r eported re sidue val ues we r e not co rre cted for appare n t residues in controls.

Tabl e B. 7.6. J.1 -4. Summar y of M e thod Va l idation and P r ocedura l/Co ncurrent R ecove rie s of Cyprodinil from Tr ee Nu t s. M a tri x Fortification Samp le size Rec overies 1 Mean ± Std
. D ev. Level ( ppm ) (n) (%) (%) Method va li dation Almond nutmeat 0.0 1-1. 0 6 7 1-8 3 75 ± 5.1 Almond hull s 0.01-1.0 6 74 -1 05 85 ± 1 2 Conc urr e nt recoverie s Almond nutm eat 0.0 1 -0.10 ..i 83-97 88 ± 6.7 Almond hull s 0.0 1-1 0 5 75 -89 82 ± 5.8 Pecan nutmeat 0.01-1.0 4 70-92 8 1 ± 11 1 Co n curren t recoveries were corrected for apparent re s idu es in co ntrol s. 

### Samples we r e s tored frozen for a maximum of 29 8 days (9. 8 months) from harvest to extraction (Tab le B.7.6.1 .1- 5). Samples were analyzed within 14 days of extraction. Th e p etitioner indicated that storage stabi lity data were ava ilable for tree nut s (Syngenta St udy No. T003062- 07); however, these data do not appear to have been reviewed by the agenc y. Acceptab le s tora ge stability data are availab le indicating that r esidues of cyp r odini l are s table during frozen s torage for up to 2 ye ars in/on a va ri ety of crops includin g wheat ea r and s talk ( DP #s 233561 , etc ., 2 /20/ 98 , G. Kramer). Th e available d at a are adeq uate to s upport the storage co nditions and durati ons for samp le s from the s ubmitted crop field trial s .

Tab le B.7.6.1.1-5. S u mmary of Storage Cond it i o n s. Matri x Storage Act ual S torage Duration ' I nt e rva l of Demon s trat ed S to rage Stabi li ty ( RA C) Temperature (°C) Pecan nutmeat < -I 0 at the fi e ld 288-298 days The petitioner indicated that s torage s tability data were s ites: - 20 at the ( 9.5-9.8 months) available for tree nuts (Sy ngenta Study 1 o. T003062

- 07): Almond nutmeat analytical 242-294 days however. the s e data do not appear to have been reviewed by laboratory (8.0

-9.7 months) th e agency. Acceptable s torage s tability data are ava il ab le Al mo nd hull s 244-296 da ys indicatin g th at residues of cyprodini l arc s table durin g froze n ( 8 .0

-9.7 mo nth s) s torag e for up to 2 years in / on a va ri e ty of crop s in c lu din g wheat car and s talk2 • 1 Int erva l from ha rve s t to ex trac ti o n . Samp les were a na l yzed within 0 -1 4 day s o f ex t rac ti o n. 2 D P#s 23356 1. etc .. 2/20/ 98. G. Kramer. 

### The results from the s ubmitted field tri a ls are presented in Tables B.7.6.1.1- 6 and B.7.6.1.1-7. In tree nut s harv es ted at a 

### PHI of 13-14 days following the la s t of fou r foliar broadcast application s of a 2.09 lb ai / gal EW fo rmulation at a total rate of 1
. 30 -1. 34 lb ai/ A, individual sam ple (and p ertrial average) residues of cyprodinil were < 0.010-0.0408 ( < 0.010

- < 0.0254) ppm in/on pecan ( nutm eat), < 0.010-0.0146 (< 0.010-0.013 I ) 

### ppm in/on almond ( nutmeat) , and 0.707-6.46 (0
.707- 5.48) ppm in/on almond ( hulls )
.

EPA MRID # : 49470603 PMRA # of document: Not avai l able Page 6 of8Cyprodi nil [P C Code 288202) /Sy ngenta Cro p Protection, LL C [CGA2 l 94 l 7) 

### In the one residu e decl in e trial , residues of cyprod inil generally declined in /on a l mo nd nutmeat and hulls wi th incr easing PHI. Table B.7.6.1.1-6. Re s id ue Data from Tree Nuts F ie ld Tria ls with Cyprodini l. 1 Location: City. Zone Tree Nut/ Matrix R ate PHI Residues 2 (ppm) [Average] State; Year (Trial Variety (lb ai/A) (days) ID) C hul a, GA; 20 11 2 Pecan/ Nu tm eat 1.31 14 <0.0 10, 0.0408 (<0.0254] (TK0059529

- 0 1) Sumner Pineview, GA; 20 11 2 Pecan / Nutmeat 1.32 13 0.0 107. < 0.010 (<0
. 0 104 ] (TK0059529

- 02) Dcsireable Alexandria, LA: 4 P ecan/ Creek Nutmeat 1.32 13 0.0 118 , < 0.0 10 [< 0.0109] 201 1 (TK0059529

- 03) Mad ill
. OK; 20 11 6 Pecan/ Nutmeat 1.30 1 3 < 0.0 1 0, <0.010 [< 0.0 1 0 ] (TK0059529

- 04) Wichita Altus
. OK: 20 11 8 P ecan/ Nutmeat 1.30 14 < 0.010, < 0
. 010 [< 0.0 1 0 ) (TK0059529

- 05) Wichita S trathm ore, CA: 10 Almond/ Nutmeat 1.32 14 0.0 115 , 0.0 105 (0.01 1 0) 201 1 Carmel Hulls 6.46, 4.49 (5 .48] (TK0059529

- 07) Chico. CA; 20 11 10 Al m ond/ Nutmeat 1.32 14 < 0.010. < 0.0 10 [< 0.010] (TK0059529-08) Price Hulls 0.707 , 0.707 (0.707) Dinuba, CA: 201 1 10 Almond / Nutmeat 1.31 14 < 0.0 10, < 0.0 10 [< 0
. 010] (TK0059529-09) Carmel Hulls 3.54. 3.89 ( 3. 72] Madera. CA; 20 11 10 Almond/No n Nutmeat 1.34 0 0.0238 [0.0238] (TK0059529- I 0) Parc il 5 0.0239 (0.0239] 9 0.0 171 [0.0171] 14 0.0 1 15, 0.0146 [0.0 131] 19 < 0.010 ( < 0.0 10) Hu ll s 0 3.43 [3.43] 5 2.30 [2
. 30] 9 2.27 [2
. 27] 14 2. 15, 2.40 (2.28) 19 1.65 [ 1.65] 1A 2.09 lb a1 /gal EW form ul ation was used. "The LOQ was 0.0 1 ppm: th e LOO was not reported. Per-tria l averages were calculated by the stud y reviewer. Tab le B.7.6.1.1-7. S ummar y of Re s idue s from Tree N u t F i e ld Tria ls with Cy prod i n il. Crop Matrix Total PHI n ' Residues (ppm) App lication (days) Min. 2 Max
. 2 LAFT3 HAFT3 Median 3 Mcan 3 SD 3 Rate (lb ai /A) Pecan nutmeat 1. 30 -1 .32 13 -1 4 5 <0
. 0 10 0.0408 < 0.0 1 0 <0.0254 0.0 104 0
. 0 133 0.00676 A l

mond nu tm eat 1.31-1.34 14 4 < 0.0 10 0.0 146 <0.0 1 0 0.0 131 0.0 105 0.0 11 0 0
. 00 1 44 A lmond hulls 14 4 0.707 6.46 0.707 5.48 3.00 3.04 2.03 1 n = number of field trials. 2 Values based on total number of s amp l es . 3 Values based on per-trial averages. LAFT =lowest average field tria l, HAFT = highest average fie l d tri al, SD = standard deviation. For computation of the LAFT, I I AFT. median. mean. and standard deviation, values < LOQ were ass um ed to be at the LOQ (0.010 ppm).

E PA MRJD # : 49470603 PMRA # of do c ument: Not available Pa ge 7 of8C y prodinil [PC Cod e 288202)/ Syngenta Crop Protection , LLC [CGA2 I9417) 

### lll. CONCLUS IO NS The tree nut field trials are considered scientifically acceptable. 

### In tree nuts harvested at a PHI of 13- 14 days following the last of four foliar broadcast app licati ons of a 2.09 lb ai / gal EW formulation at a total rate of 1.30-1.34 lb ai/ A , indi v idu al sample (and per-trial average) residues of cyprodini l were <0.010-0.0408 ( < 0.010

- < 0.0254) ppm in/on pecan (nutmeat), < 0.010-0.0146 ( < 0.010

- 0
. 013 I) ppm in/on almond (nutmeat) , and 0.707-6.46 (0.707-5.48) ppm in/on almond (hulls). 

### In the one residue decline trial , residues of cyprod inil generall y declined in/ on almond nutmeat and hulls with increasing PHI. An 

### acceptab le method was used for residue quantitation , and adequate storage stabi li ty data we re availab le to support sample storage durations and conditions. 

### REFERENCES DP# s 23356 1 , etc. , 2/20/ 98 , G. Kramer

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