Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY 

WASHINGTON, D.C. 20460 

MEMORANDUM 

Date: March 30, 2016 

OFFICE OF CHEMICAL SAFETY 

AND POLLUTION PREVENTION 

SUBJECT: Cyprodioil. Petition Proposing a New Tolerance for the Use of Cyprodinil in/on 

Tree Nuts Crop Group 14-12; except almond. except pistachios. Summary of 

Analytical Chemistry and Residue Data. 

PC Code: 288202 

Decision No.: 497939 

Petition No.: 4F8333 

Risk Assessment Type: NA 

TXR No.: NA 

MRJD No.: 49470601 , 49470602, & 49470603 

DP Barcode: 0425723 

Registration Nos.: I 00-811 & I 00-1317 

Regu la tory Action : Secrion 3 

Ca se No.: 7025 

CAS No.: 121552-61-2 

FROM: Thurston G. Morton, Chemist 

41#1ZtRisk Assessment Branch 4 

Health Effects Division (7509P) 

THROUGH: Elissa Reaves, PhD, Branch Chief 

Risk Assessment Branch 4 

Health Effects Division (7509P) 

TO: Marcel Howard 

Fungicide Branch 

Registration Division (7505P) 

Page 1of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

Executive Summary 

Cyprodinil is an anilino-pyrimidine fungicide used to control various plant diseases on a wide 

variety of fruit, nut, vegetable and herb crops. Under PP#4E8273, Syngenta is requesting the 

establishment of tolerances for residues of cyprodinil [ 4-cyclopropyl-6-methyl-N-phenyl-2-

pyrimidinarnin] in/on the following raw agricultural commodities: 

Nut. Tree, Group 14-1 2; except almond. except pistachio ........... 0.04 ppm 

In conjunctio n with PP# 4F8333, Syngenta is requesting a Section 3 registration for Inspire Super 

TM Fungicide (EPA Reg. No. 100-1317), a 2.09 lb ai/gallon emulsion oil in water (EW) 

formulation to tree nuts. In support of this new use, Syngenta has submitted new magnitude of 

the residue data for cyprodinil. 

This product (EPA Reg. No. 100-1317) addressed herein contains a second active ingredient 

(difenoconazole). The subject review addresses the proposed use and supporting data for 

cyprodioil only. 

The nature of cyprodinil residues in plants is understood based on adequate metabolism studies 

on apple, peach, potato, tomato, and wheat. Only residues of parent cyprodini l need to be 

included in the tolerance expression and considered for risk assessment for plant commodities. 

The nature of cyprodinil residues in ruminants is also understood based on an adequate goat 

metabolism study. The residues of concern in ruminants are cyprodinil and its hydroxy lated 

metabolite CGA-304075 (free and conjugated). No poultry metabolism study is available, but 

HED has concluded that none is required. There are no new livestock feed stuffs associated with 

the proposed new uses of cyprodinil. 

Adequate HPLC/UV methods (Methods AG-631 and AG-631 B) are available for enforcing 

tolerances of cyprodinil in/on plant commodities. The limits of quantitation (LOQ) for the plant 

methods range from 0.0 I to 0.065 ppm depending on the commodity. An adequate LC/MS 

method (GRMO I 0.01 A) is also available for enforcing tolerances of cyprodinil residues in 

livestock commodities. The method LOQ for this method is 0.02 ppm for the combined residues 

of cyprodinil and its metabolite CGA-304075 (free and conjugated), expressed as parent. 

Syngenta has submitted a high performance liquid chromatography method with tandem mass 

spectrometry detection (LC/MS/MS), method GRMOl 0.02A, for anal ysis of residues of 

cyprodinjl in/on a variety of crops inc luding tree nuts. The method is a modified version of 

method REM 141.0 I , the original enforcement method for cyprodinil. A complete method 

description (MRID 49470602) and supporting method validation data (MRID 49470601) have 

been submitted. The method was used for analysis of residues of cyprodinil in the tree nut crop 

field lrial studies submitted under the current action (refer to 49470603.der; B.7.6.1.1 ). Because 

the method monitors multiple ion transitions for determination of cyprodinil, no confirmatory 

procedures are needed. An Independent Laboratory Validation (ILV) of the method was not 

submitted. Provided the method is not proposed for enforcement, no ILV is necessary. No 

radiovalidation data have been submitted for method GRMO 10.02A. The extraction procedures 

used for this method are the same as those used for the established enforcement methodology, for 

Page 2of 17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

which radiovalidation data were previously submitted and reviewed (refer to DP#s 233561 , etc., 

2/20/98, G. Kramer); therefore, no additional data are required. The LC/MS/MS method 

GRM010.02A was adequately validated for determining residues of cyprodinil in crops including 

tree nuts. The validated LOQ is 0.0 I ppm. A confimrntory method is not required because the 

method monitors two ion transitions. 

In tree nuts harvested at a PHI of 13-14 days following the last of four foliar broadcast 

applications of a 2.09 lb ai/gal EW formulation at a total rate of 1.30-1 .34 lb ai/ A, individual 

sample (and per-trial average) residues of cyprodinil were <0.010-0.0408 (<O.OI0-<0.0254) ppm 

in/on pecan (nutmeat), <0.010-0.0146 (<0.010-0.0131) 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 

cyprodinil generally declined in/on almond nutmeat and hulls with increasing PHI. 

The Organization for Economic Cooperation and Development (OECD) tolerance calculation 

procedures were used to determine appropriate tolerance level. A tolerance level of 0.04 ppm for 

nut, tree, group 14-12; except almond, except pistachiq in accordance with ·'Reviewer's Guide and 

Summary of HED Chem SAC Approvals for Amending Crop Group/Subgroups [ 40 CFR 180.41] 

and Commodity Definitions [40 CFR 180. l(h)]" (B. Schneider, 6/ 14/06). 

No Codex, Canadian, or Mexican MRLs are established in/on tree nut commodities other than 

pistachio and almond. 

Regulatory Recommendations and Residue Chemistry Deficiencies 

HED has examined the residue chemistry database for cyprodinil. With regards to cyprodinil for 

PP#4E8333, pending submission of a revised Section F (see requirements under Proposed 

Tolerances), there are no residue chemistry issues that would preclude granting amended 

registrations for Inspire Super r" Fungicide (EPA Reg. No. I 00-13 I 7) to expand currently 

registered foliar uses for nut, tree, group 14- 12, except almond and pistachio or establishment of 

tolerances for residues of cyprodinil only in/on the following commodities: 

Nut, tree, group 14-I 2, except almond and pistachio ............... 0.04 ppm 

A human health risk assessment is forthcoming. 

Notes to PM: 

Tolerance should be revised, as needed, to reflect the correct commodity definitions as specified 

in Table 8. 

Background 

Cyprodinil is an anilino-pyrimidine fungicide used to control various plant diseases on a wide 

variety of fruit, nut, vegetable and herb crops. Tolerances for residues of cyprodinil have been 

established in/on a variety of crop commodities at levels ranging from 0.02-170 ppm [40 CFR 

Page 3of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

§ 180.532]. Tolerances have also been established at 0.02 ppm for cyprodinil residues in meat 

byproducts of cattle, goats, horses, and sheep. No tolerance is established for poultry byproducts. 

The chemical structure, nomenclature, and physicochemical properties of the technkal grade of 

cyprodinil are presented in Tables 1 and 2. 

Table I. Cyprodinil Nomenclature. 

Compound 

H 

UNyN~ 

N ~ 

CH3 

Common name Cyprodinil 

Company experimental name CGA2 194 17 

IUPAC name (4-cyclopropyl-6-methyl-pyrimidin-2-yl)-phenyl-amine 

CAS name 2-ovrimidinamine. 4-evclopropyl-6-mcthvl-N-phenvlCAS registry number 121 552-61-2 

End-use product (EP) 75% water-dispersible granule fonnulation (Vangard® WG Fungicide: EPA Reg. No. 

100-828): a multiple active ingredient (MAI) end-use product (Inspire Super"' Fungicide: 

EPA Reg. No. I 00-1 3 17) fonnulated as an emulsion [oi l) in water (EW). containing 8.4% 

difcnoconazole and 24.1 % cvorodinil 

Table 2. Physicochemica l Properties of Technica l Grad e ofCypr odinil. 

Parameter Value Reference 

Melting point/range 75.9 °c DP#s 345970 and 345 182. W. 

pH 9.5 al 25 °c ( 1% aqueous dispersion) Cutchin. 6/4/08 

Density 1.21 g/cm3 at 20 °c 

Water solubility {mg/L at 25 C) pH 7.6 16 

pH 5 20 

pll 7 13 

pll 9 15 

olvent solubility (g/L at 25 C) ethanol 160 

acetone 610 

toluene 460 

n-octanol 160 

n-hexanc 30 

Vapor pressure 3.8 x 10·<> mm Hg at 25 °c 

Dissociation constant. pK, 4.44 at 20 °c 

Octanol/water partition coefficient. Log(Kow) 3.9 at pH 5 

at 25 C 4.0 at pll 7 

4.0 at pit 9 

UV/visible absorpiion spectrum 29.200 l/mol·crn at 270.8 nm (neutral} 

(molar absorption coefficients for the 29.200 l/mol·cm a1 25 1.6 nm (acidic) 

absorbance maximum) 29.200 l/mol·cm at 3 16.8 nm (acidic) 

28.400 l/mol·cm at 270.8 nm (basic) 

Page 4of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

860.1200 Directions for Use 

Table 3. Summary of Proposed Directions for Use of Cyprodin il 

Applic. Timing, Fonnulation Applic. Max. No. Max. Seasonal PHI Use Directions and Type, and [EPA Reg. Rate Applic. Applic. Rate (days) Limitations Equip. No.] (lb ai/A) per Season (lb ai/A) 

Tree Nuts 

Inspire Super 

A minimum retreatment 

Broadcast foliar interval (RT!) of 14-21 

Ground & 2.09 lb/gal 0.33 4 implied 1.3 14 days is proposed. Do not EW Aerial [I 00-1 3 17] apply more than 2 

applications by air. 

Conclusions. The proposed use directions are sufficient to allow for evaluation of the available 

residue data. 

860.1300 Nature of the Residue - Plants 

DP# 2 19794, G. Kramer, 2/13/96 

DP# 2331 82, G. Kramer, 2/20/98 

MARC Decision Memo, DP# 243198, G. Kramer, 3/ 11 /98 

The nature of the residue in plants is adequately understood based on acceptable metabolism 

studies on apple, peach, potato, tomato, and wheat. These studies indicated that cyprodinil is 

metabolized primarily by hydroxylation followed by sugar conjugation. Cleavage of the amino 

bridge, opening of the pyrimidine ring, opening of the cyclopropyl ring and formation of 

thiolactic acid conjugates are minor pathways. Incorporation into starch was observed in potato 

tubers and wheat grain. The MARC reviewed these studies and determined that the residue of 

concern, for purposes of tolerance enforcement and risk assessment, is cyprodinil. 

860.1300 Nature of the Residue - Livestock 

DP# 233182, G. Kramer, 2/20/98 

MARC Decision Memo, DP# 243198, G. Kramer, 3/ 11 /98 

DP# 345970 and 345 182, G. Kramer, 6/4/08 

DP# 362486, J. Stokes, 9115109 

The nature of the residue in ruminants is adequately understood based on acceptable lactating 

goat metabolism studies using (

14C-phenyl] and [14C-pyrimidinyl] cyprodinil. The metabolism of 

cyprodinil in ruminants proceed predominantly via hydroxylation followed by conjugation with 

sulfuric and glucuronic acid. Breakdown of the pyrimidinyl ring was seen only in the liver and 

resulted in Metabolite L l. Cleavage of the amino bridge between the phenyl and the pyrimidinyl 

Page 5of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP# : 425723 

rings was only a minor reaction as indicated by the small amounts of CGA 249287 found in the 

liver and kidneys of goats dosed with (1 4

C-pyrimidinyl]cyprodinil. 

HED originally concluded there were no cyprodinil metabolites of toxicological or regulatory 

concern in ruminant milk and tissues based on the dietary burden associated with the registered 

cyprodinil uses 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 livestock 

dietary burden, then a new cyprodinil feeding study would be required in which residues of 

cyprodinil and CGA 304075 (both free and conjugated) are determined. ARIA subsequently has 

concluded that the residues of concern for both risk assessment and the tolerance definition 

should include the combined residues of cyprodinil and metabolite CGA-304075 (free and 

conjugated), expressed in parent equivalents. 

A poultry metabolism for cyprodinil has not been submitted and none has been requested since 

the potential dietary exposure of poultry to cyprodinil residues is extremely low (estimated at 

0.005 ppm based on canola meal consumption). There is no reasonable expectation 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 study. 

Summa r y of Meta bolites and Degradates to be included in the Risk Assessment a nd Tolerance Ex pression 

fo r Cvorodinil 

Matrix Risk Assessment 

Plants cyprodinil 

Livestock cyprodinil and CGA-304075 

Water cyprodinil and CGA 249287 

860.1340 Residue Analytical Methods 

MRID #s: 4947060 I, 49470602, 

Tolerance Expression 

cvorodinil 

cyprodinil and CGA-304075 

NA 

Enforcemenr methods. Adequate HPLC/UV methods with column switching (Syngenta Methods 

AG-631 and AG-631 B) are available for enforcing tolerances of cyprodinil on plant 

commodities. The LOQs for these methods range from 0.01 to 0.065 ppm depending on the 

plant commodities. Method AG-63 1 B also contains procedures for confirmatory analysis by 

GC/NPD. 

An adequate HPLC/MS method (GRMOlO.OlA) is also available for enforcing tolerances in 

livestock commodities. This method determines residues of both parent and the metabolite 

CGA-304075 (free and conjugated), expressed as parent. The LOQ is 0.01 ppm for each analyte 

for a combined LOQ of 0.02 ppm. 

Data collection methods. Syngenta has 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~ including tree nuts. The method is a 

modified version of method REM141.01 , the original enforcement method for cyprodinil. A 

complete method description (MRJD 49470602) and supporting method validation data (MRJD 

49470601) have been submitted. The method was used for analysis of residues of cyprodinil in 

the tree nut crop field trial studies submitted 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 6of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

no confirmatory procedures are needed. An Independent Laboratory Validation (ILV) of the 

method was not submitted. Provided the method is not proposed for enforcement, no lL V is 

necessary. No radiovalidation data have been submitted for method GRM010.02A. The 

extraction procedures used for this method are the same as those used for the established 

enforcement methodology, for which radiovalidation data were previously submitted and 

reviewed (refer to DP#s 233561, etc., 2/20/98, G. Kramer); therefore, no additional data are 

required. The LC/MS/MS method GRMO l 0.02A was adequately validated for determining 

residues of cyprodinil in crops including tree nuts. The validated LOQ is 0.01 ppm. A 

confirmatory method is not required because the method monitors two ion transitions. 

Conclusions. The LC/MS/MS method GRM010.02A was adequately validated for determining 

residues of cyprodinil in crops including tree nuts. The validated LOQ is 0.01 ppm. A 

confirmatory method is not required because the method monitors two ion transitions. 

860.1360 Multiresidue Methods 

G. Kramer, 11/2811995 

Data are available depicting the recovery of cyprodinil and its metabolite CGA-232449 through 

FDA Multiresidue method testing protocols (C through E). Acceptable recoveries were obtained 

for cyprodinil in apple fortified at 0.50 ppm using Protocol D. These data were forwarded to 

FDA. 

860.1380 Storage Stability 

0233182. G. Kramer. 02/20/98 

0288706, T. Bloem .7124/03 

The maximum storage interval for samples between harvest and extraction was 298 days (9.8 

months) for pecan (nutmeat) and almond (nutmeat and hulls). Samples were analyzed within 14 

days of extraction. The petitioner indicated that storage stability data were available for tree nuts 

(Syngenta Study No. T003062-07); however, these data do not appear to have been reviewed by 

the agency. Acceptable storage stability data are available indicating that residues of cyprodinil 

are stable during frozen storage for up to 2 years in/on a variety of crops including wheat ear and 

stalk (DP#s 233561, etc., 2/20/98, G. Kramer). These data are acceptable to support storage 

conditions and durations of samples from the submitted field trials. 

860.1400 Water, Fish, and Irrigated Crops 

The proposed uses are not relevant to this guideline. 

860.1460 Food Handling 

The proposed uses are not relevant to this guideline. 

Page 7of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data 

860.1480 Meat, Milk, Poultry, and Eggs 

DP#s 345970 and 345182, W. Cutchin, 6/4/08 

DP# 362484, J. Stokes, 9/ 15/09 

DP#. 378920, B. Cropp-Kohilligian, 10/27/ 10 

DP# : 425723 

Adequate cattle feeding studies are available for cyprodinil, and tolerances for cyprodinil 

residues in livestock commodities were assessed in conjunction with petitions for tolerances on 

various plant commodities. Using the Agency's most recent guidance on constructing reasonably 

balanced livestock diets the maximum reasonably dietary burdens (MRDBs) of livestock for 

cyprodinil 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. Based on these MDBs, tolerances for residues of cyprodinil 

and free and conjugated CGA-304075, expressed in parent equivalents, were required on meat 

byproducts of cattle, goats, horses, and sheep at 0.02 ppm (LOQ). 

Previously, 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 using almond hull in place of wet apple pomace. The dietary contribution 

from the almond hulls alone did not increase the total dietary burden. However, this proposed 

amended use on almonds was withdrawn and the increased tolerance for almond hulls did not 

occur. 

Conclusions. The proposed new uses do not contain any additional livestock feed stuffs other 

than those previously registered, therefore, HED has determined that the currently established 

0.02 ppm tolerance levels for meat byproducts of cattle, goats, horses, and sheep are adequate. 

860.1500 Crop Field Trials 

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 

applications of a 2.09 lb ai/gal EW formulation at a total rate of 1.30-1.34 lb ai/ A, individual 

sample (and per-trial average) residues of cyprodinil were <0.010-0.0408 (<0.010-<0.0254) ppm 

in/on pecan (nutmeat), <0.010-0.0146 (<0.010-0.0131) 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 cyprodinil generally declined in/on almond nutmeat 

and hulls with increasing PHI. 

Summa ry of Residues from Tree Nut Field Trials with Cyprodinil. 

Crop Matrix Total PHI n ' Residues {ppm) 

Application (days) Min. 2 Max.2 L/\FT3 llAFT3 Mcdian3 Mean3 SD3 

Rate 

(lb ai/A) 

Pecan nutmeat 1.30-1.32 13-14 5 <0.0 10 0.0408 <0.0 10 <0.0254 0.0104 0.0 133 0.00676 

Almond nutmeat 1.31-1.34 14 4 <0.0 10 0.0 146 <0.0 10 0.0131 0.0 105 0.0 11 0 0.00 144 

Almond hulls 14 4 0.707 6.46 0.707 5.48 3.00 3.0.t 2.03 

1 n = number of field tnals. 

Page 8of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

2 Values based on total number of samples. 3 Values based on per-trial averages. LAFT = lowest average field trial, HAFT = highest average field trial, SD= standard 

deviation. For computation of the LAFT, I IAFT, median. mean. and standard deviation. values <LOQ were assumed to be at the 

LOQ (0.010 ppm). 

Conclusion: The data adequately support the requested tol erances and proposed use pattern. 

860.1520 Processed Food and Feed 

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 almond. 

860.1650 Submittal of Analytical Reference Standards 

Analytical standards for cyprodinil (expiration date 7/30/2018) and CGA-304075 (expiration 

date 8/3112016) are currently available in the EPA National Pesticide Standards Repository 

(email communication with T. Cole, ACB, 04/08/2015). 

860.1850/1900 Confined and Field Accumulation in Rotational Crops 

DP# D257898, S. Levy, 21812000 

DP# D3 26346, W. Wassell, 10/ 18/2006 

Adequate confined and limited field rotational crop studies are available and were conducted at 

2.2x and 1.5x the current maximum use rate for rotated crops (1.3 lb ai/A). On the basis of these 

studies, the HED requested a field rotational crop study which also monitored for residues of 

CGA-232449, NOA-422054, CGA-249287, and CGA-263208. 

In the subsequent field accumulation study, cyprodinil (WDG) was applied to mustard greens at 

four test sites in CA (2 tests) and NY (2 tests) as four broadcast foliar applications at 0.328 lb 

ai/A/application at 7-day retreatment intervals for a total of 1.31 lb ai/A (Ix rate). The primary 

mustard greens crop was destroyed and removed 7 days after the final application, and rotational 

crops of wheat, lettuce and garden beets were 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 

each test at the appropriate stage of maturity. All samples were analyzed for residues of parent 

and each metabolite (CGA-232449, NOA-422054, CGA-249287, and CGA-263208) using an 

adequate HPLC/MS method (Method 2213-01 ), which has a validated LOQ of0.05 ppm for 

parent and each metabolite. 

As residues of parent and each metabolite were <LOQ in/on all lettuce, garden beet and wheat 

RAC samples, HED concluded that rotational crop tolerances are not currently required. 

860.1550 Proposed Tolerances 

The Agency has determined that the residue of concern in plant commodities for the tolerance 

expression is only cyprodinil. Tolerances have been established for residues of cyprodinil in/on 

Page 9of 17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

a variety of crop commodities, at levels ranging from 0.02 ppm in/on almond to 340 ppm in 

citrus oil (40CFR§180.532(a)]. Tolerances have also been established at 0.02 ppm for 

cyprodinil and its metabolite CGA-304075 residues in meat byproducts of cattle, goats, horses 

and sheep. 

Table 8. Tolerance Summary for Cyprodinil 

Commodity Established/Proposed Recommended Comments; Correct Commodity 

Tolerance (ppm) Tolerance (ppm) Definition 

Tolerances Proposed Under PP#4F8333 

Nut, tree, group 14-12; 0.04 0.04 Nut, tree, group 14-12, except almond 

except almond. except and pistachio 

pistachio 

References 

DP Numbers: 

Subject: 

From: 

To: 

Dated: 

MRJD(s): 

DP Numbers: 

Subject: 

From: 

To: 

Dated: 

MRJD(s): 

DP Numbers: 

Subject: 

From: 

To: 

Dated: 

MRID(s): 

378920 

Cyprodinil. Cyprodinil. Amended Use and Amended Tolerance Petition for Pome Fruit. 

Summary of Analytical Chemistry and Residue Data. 

B. Cropp-Kohlligian 

L. Jones 

I 0/27/10 

47644301 

362486 

Cyprodinil. Petition for Tolerance on Canola Seed Imported from Canada. Summary of 

Analytical Chemistry and Residue Data. 

J. Stokes 

L. Jones 

09/ 15/09 

47644301 

345970 and 345182 

Cyprodinil. Section 3 Requests for Uses on Tomato, Avocado, Herbs, Root Vegetables, Leaves of 

Root and Tuber Vegetables, Lemon, Lime, Cucurbits, Kiwifruit, Green and Dry Bulb Onions, and 

Strawberries. Registrant's Response to Conditional Registration on Carrots and Brassica 

Vegetables and Livestock Feeding Study. Summary of Analytical Chemistry and Residue Data. 

W. Cutchin 

W. Cutchin/B. Madden 

06104108 

4716110 1-47161107 and 47169305-47169311 

Page 10 of l 7 
Cyprodinil 

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 Revised Label, Field 

Accumulation in Rotational Crops, Storage Stability, and Analytical Methods Data Requested as 

Conditions of Registration. 

W. Wassell 

L. Jones/M. Waller 

I 0/ 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 Leafy Greens Crop 

Subgroup, Head and Stem Brassica Crop Subgroup, and Turnip Greens (ID#- 2£06485); Carrot 

(ID# - 2E0646 I); and Herb Crop Subgroup (IO# - 3 E06529). Summary of Residue Chem is try 

Data. 

T. Bloem 

R. Forrest 

07/24/03 

45682401 , 45721502, 45726101,45726102, 45795301 , 45795302, and45839801 

257898 

PP# 8£05012. Cyprodinil in/on Strawberries and Bulb Vegetables (Crop Group 3). Evaluation of 

Residue Data and Analytical Methods. 

S. Levy 

R. Forrest/S. Brothers 

02108100 

446 15602, 4461560 I, 448673 12, 448673 14 

243198 

Cyprodinil. HED Metabolism Assessment Review Committee Meeting 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, 

A Imonds and Grapes. Evaluation of Residue Data and Analytical Methods. 

G. Kramer 

M. Wallcr/T. Ellwanger 

02120198 

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 - Cyprodinil and Propiconazole in or on Stone Fruit. Evaluation 

of Residue Data and Analytical Methods. 

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 

11128195 

43709050 

Page 11 of 17 
Cyprodinil Summary of Analytica l Chemistry and Residue Data 

Attachments: 

Appendix I - International Tolerances 

Appendix IT - Tolerance Assessment Calculations 

F. DOCUMENT TRACKING 

R.01: E. Reaves 3/30/ 16 

Petition Number: 4F8333 

DP#: 425723 

PC Code: 288202 

Template VcrsionScptcmber 2005 

Page 12of17 

DP#: 425723 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

Appendix I. International Tolerances 

Cyprodinil (PC Code 288202: ) 

Summary of US and International Tolerances and Maximum Residue Limits 

Residue Definition: 

us Canada Mexico2 Codex 

40 CFR 180.532: 4-cyclopropyl-6-methyl- Cyprodinil 

N-phenyl-2- The residue is 

Plant: Cyprodinil (4-cyclopropyl-6-methyl-N- pyrimidinamine fat soluble. 

phenyl-2-pyrimidinamine). 

Commodity' Tolerance (ppm) /Maximum Residue limit kf!.) 

us Canada Mexico2 Codex 

Nut, rree, group 14-12; except almor d0.04 

except pistachio 

Completed: 

1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and 

not those proposed by the applicant. 

2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes. 

Page 13of 17 
Cyprodinil Summary of Analytical Chemistry and Residue Data DP#: 425723 

Appendix II. Tolerance Assessment Calculations. 

For each of the crops listed below, the OECD MRL Calculator User Guide (SOP), along with the 

tolerance spreadsheet, was used for calculating recommended tolerances. As specified in the 

SOP, the tolerance calculation is in the region of the 95111 percentile of the underlying residue 

distribution, and is more likely to overestimate rather than underestimate the 95111 percentile. The 

rounding procedures specified in the SOP were also used. The OECD tolerance spreadsheet does 

not require the use of maximum-likelihood estimation (MLE) procedures for values <LOQ. 

Using the OECD MRL Calculator, the recommended tolerances are 0.04 ppm for Nut, tree, group 

14-1 2; except almond, except pistachio 

Page 14of17 
Cyprodinil Summary of Analytical Chemistry and Residue Data 

Cyprodinil 

Tree Nuts - Pecan 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 resi due 

Median residue 

Mean 

Standard deviation (SD) 

Correction factor for censoring (CF) 

Proposed MRL estimate 

- Hi ghest residue 

- Mean + 4 SD 

- CF x 3 Me an 

Unrounded MRL 

Rounded MRL 

~igh uncerta~~ty of MRL estimate . 

[Small dataset] 

Resi dues (mg/ kg) n 

< 0 . 01 2 

0 . 0104 1 

0 . 0109 1 

0 . 0254 1 

Page 15of17 

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#: 425723 
Cyprodinil Summary of Analytical Chemistry and Residue 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 esti mate 

- Hi ghest residue 

- Mean + 4 SD 

- CF x 3 Mean 

Unrounded MRL 

Rounded MRL 

High uncertainty of MRL estimate . 

[Small dataset] 

Residues (mg/kg) n 

< 0 . 01 2 

0 . 011 1 

0 . 013 1 

Page 16of 17 

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#: 425723 
Cyprodinil Summary of Analytical Chemistry and Residue 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 

High uncertainty o f MRL est i mate . 

[Smal.i. dataset] 

Residues (mg/kg) n 

0 . 707 1 

2 . 28 1 

3 . 72 1 

5 . 48 1 

Page 17of17 

4 

0% 

4 

0 . 707 

5 . 48 0 

3 . 000 

3 . 047 

2 . 036 

1 . 000 

5 . 480 

11 . 191 

9 . 140 

11 . 191 

15 

DP#: 425723 
Volume 3 

AnnexB 

Cyprodinil 

B.S METHODS OF ANALYSIS 

B.5.2 ANALYTICAL METHODS FOR THE DETERMINATION OF RESIDUES 

(ALL COMPONENTS INCLUDED IN THE RESIDUE DEFINITION PROPOSED) 
Cyprod inil [PC Code 288202]/Syngenta Crop Protection, LLC [CGA2 l 94 l 7] 

Note: This Data Evaluation Record (DER) was originally prepared under contract by Versar. Inc. (6850 Versar Center. 

Springfield. VA 22 15 1; submitted 4/ 10/ 15). The DER has been reviewed by HED and revised to renect current Office of 

Pesticide Programs (OPP) policies. 

Table B.5.2-1. Overview of the Ana lytical Methods for the Determination of Cyprodinil Residues. 

Data Matrix Analytcs 

Requirement 

Enforcement Plant Cyprodinil 

Method- Plant commodities 

Commodities 

Data-Gathering Pome and stone. Cyprodinil 

Method - Plant fruits. tree nuts. 

Commodities grape 

Brassica Cyprodinil 

vegetables. 

carrot, tomato. 

avocado, parsley, 

radish. lemon. 

kiwifruit 

Cucurbit Cyprodinil 

vegetables. 

lettuce 

Spinach. pepper. Cyprodinil 

lemon 

Celery Cyprodinil 

Crops and tree Cyprodinil 

nuts 

ILVof 

Enforcement 

Method- Plant 

Commodities 

Radiovalidation Apple leaves. Cyprodinil 

of Methods - tomato 

Plant 

Commodities 

Enforcement Livestock Cyprodinil and 

Method- commodities CGA-304075 

Livestock 

Commodities 

Data-Gathering Ruminant milk Cyprodinil and 

Method- and tissues CGA-304075 

Livestock 

Commodities 

ILV of 

Enforcement 

MethodLivestock 

Commodities 

Radiovalidation 

of Methods -

Livestock 

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- 43709052 

63 1A. 

AG63 I B: fonnerly 

REM141.01) 

llPLC!UV 0.0 1-0.05 MR IDs 43908445. 

(AG-631) 44186417.43737603. 

44186420.43908444. 

44 1864 18 

HP LC/UV 0.01-0.05 MRI Os 47 1693 10- 11. 

(AG-6318) 47161101-07. 47417703 

llPLC!MS 0.01 

(22 13-01) 

LC 1 IS!M 0.0 1-0.02 MRIDs 48437401 -03. 

(AG63 1B: 4847850 1 

modified) 

LC!MS!MS 0.05 

(AG-5978) 

LC!MS/MS 0.0 1 Study No. TK002 I 500 

(GRMO I0.02A) MRIDs 49470601. 

49470602 

PMRA #Not available 

Not available 

REM 141.0 N/ J\ MRID 43908440 

llPLC/MS 0.0 1 MRI Os 44382601, 

(GRMO IO.O IA) 43709052.47169305 

HPLC!UV 0.01 MRIO 43908443 

(AG-635) 

HPLC/M 0.0 1 MRIO 47169309 

(GRMOJO.O IA) 

Not available 

ot available 

Page 2 of7 
Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 l 94 l 7] 

Table B.5.2-1. Overview of t he Ana lytical Methods fo r the Determination of Cyprodinil Residu es. 

Data Matrix Analytes Method Type Limit of Quantitation Reference 

Requirement (ppm) 

Multiresidue Apple Cyprodinil and its FDA-Pesticide 0.50 MRID 43709050 

Method Testing metabolite CGA- Analytical 

232449 Methods MultiResidue testing 

program 

Table B.5.2-2. Chemical Structures of Ana lytes Addressed by Methods fo r the Ana lysis of Cyprodinil. 

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) 

HPLCIUV: 

(AG-635) 

Common name: Cyprodinil 

Syngenta code: CGA219417 

Chemical name: 2-

pyrimidinamine. 4-cyclopropyl-6-

methyl-.\'-phenylCommon name: 

CGA-304075 

Chemical name: 4-[(4-cyclopropyl6-methyl-2-2-pyrimidinyl)amino]-

phenol 

B.S.2.1 Ana lytical Methods for Plant Matrices (Annex IIA 4.3, Annex IIIA 5.3) 

B.5.2.1.1 

Not applicable 

B.5.2.1.2 

Document ID: 

Report: 

Guidelines: 

Post-Registration Method (Enforcement) 

Pre-Registr ation Method (Data-Gathering) 

MRlD Nos. 49470601 and 494 70602 

PMRA No. Not available 

49470601 Lin, K. (20 11 ) Cyprodinil. Validation of Analytical Method 

GRM010.02A for the Determination of Residues of Cyprodinil in Crops 

and Tree Nuts by LC-MS/MS. Final Report. Report No. TK0021500. 

Unpublished study prepared by Syngenta Crop Protection, LLC. 66 p. 

49470602 Lin, K. and Manuli, M. (20 11 ) Cyprodinil. Analytical Method 

for the Determination of Residues ofCyprodinil in Crops and Tree Nuts 

by LC-MS/MS. Method. Report Nos. GRMO I 0.02A, TK002 l 500. 

Unpublished study prepared by Syngenta Crop Protection, LLC. 36 p. 

EPA OCSPP Harmonized Test Guideline 860.1340 Residue Analytical 

Method {August 1996) 

PMRA Regulatory Directive DIR98-02 - Residue Chemistry Guidelines, 

EPA MRID #s: 4947060 1 and 49470602 

PMRA #of document: Not avai lable Page3of7 
Cyprodinil [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 Compliance: No deviations from regulatory requirements were reported which would 

have an impact on the validity of the study. 

Acceptability: The study is considered scientifically acceptable. The acceptability of this 

study for regulatory purposes is addressed in the fort coming U.S. EPA 

Residue Chemistry Summary Doc t, D 3. 

Evaluator: Thurston G. Morton, Chemist 

Registration Action Branch 4 

Health Effects Division (HED) (7509P) 

EXECUTIVE SUMMARY 

Syngenta has submitted a high 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 version of 

method REM141.01, the original enforcement method for cyprodinil. A complete method 

description (MRlD 49470602) and supporting method validation data (MRID 49470601) have 

been submitted. The method was used for analysis of residues of cyprodinil in the tree nut crop 

field trial studies submitted under the current action (refer to 49470603.der; B.7.6. 1.1). 

Briefly, samples are extracted with methanol:water (80:20, v:v) for 1 hour. For tree nuts only, 

the extract is 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 HLB solid phase extraction (SPE) cartridge. Residues are eluted with 0.1 % 

ammonium acetate:acetonitrile (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 (mlz 226 --> 93 

for quantitation and rn/z 226 --> 77 for confirmation). 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 (signal:noise >3: I) was reported to be 0.1 pg. 

The method was adequately validated for the quantitation and confirmation ion transitions using 

samples of almond nutmeat and hulls, apple, tomato, and wheat forage, hay, and grain fortified 

with cyprodinil at 0.0 l and 0.1 ppm. Recoveries were generally within the acceptable range of 

70-120%. 

Because the method monitors multiple ion transitions for determination of cyprodinil, no 

confirmatory procedures are needed. 

An Independent Laboratory Validation (IL V) of the method was not submitted. Provided the 

method is not proposed for enforcement, no IL V is necessary. 

No radiovalidation data 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 

EPA MRlD #s: 49470601and49470602 

PMRA # of document: Not available Page 4 of7 
Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 l 9417) 

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

DP#s 233561, etc., 2/20/98, G. Kramer); therefore, no additional data are required. 

I. Principle of the Method: GRM010.02A 

Ta ble B.5.2. 1.2- 1. Summary Para meters fo r the Pre-Registration Ana lytical Method Used for the Analysis 

of Cyprodinil Residues in Crops a nd T ree Nuts. 

Method ID GRMO I0.02A 

Analytc(s) Cyprodinil 

Extraction solvent Wld Briefly. samples are extracted with methanol:water (80:20. v:v) for I hour. For tree nuts only, the 

technique extract is then acidified to pl I 2-3 with the addition of concentrated I !Cl. For all crops. the extract 

is centrifuged then liltcrcd. 

Clean-up strategics An aliquot of the extract is combined with 0. 1% ammonium acetate and applied to a Waters HLB 

SPE cartridge. Residues are eluted with 0.1 % ammonium acetate: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. 

Instrument and Detector LC/MS/MS using a Supelco Ascent is® Express Cs column and a gradient mobile phase of water 

and methanol with MS/MS detection using multiple reaction monitoring (MRM) operated in the 

positive ion mode. The followi ng ion transitions are monitored for determination of cyprodinil: 

m/: 226 -+ 93 for quantitation and m/: 226 - 77 for confinnation 

Standardization method External standardiz.ation using calibration standards to generate a five-point calibration curve over 

the range of 0.01-0.20 ng/mL. 

Stability of std solutions Stability of standard solutions was not reported. Final extracts in 0. 1% ammonium acetate:ACN 

(70:30. v:v) were stable when stored refrigerated (-4 °C) for at least 6-12 days. 

Retention times 4.7 minutes. 

II. Specificity 

The LC/MS/MS method is highly selective for both the quantitation and confirmation of 

cyprodinil. Analysis of control samples resulted in no significant signals at the expected 

retention times of the analytes. The petitioner submitted data indicating that no interference was 

observed at >30% LOQ at or near the retention time of cyprodinil in any of the untreated crop 

components. 

Unan1biguous identification is ensured by monitoring two MS/MS transitions: 

Cyprodinil m/z 226-+ 93 (quantitation) 

m/z 226 -+ 77 (confirmation) 

Because the method monitors multiple ion transitions for the determination of residues of 

cyprodinil, no confirmatory procedures are needed. 

III. Linearity 

The linearity of detector response was evaluated using solvent standard solutions. Calibration 

curves were calculated by linear regression analysis. For the equation which describes the 

detector response as a function of the standard concentration, calibration curves resulting from 

the injection of a minimum of five standards over the concentration range of 0.01-0.20 ng/mL 

demonstrated linearity with coefficients of determination (r2) of at least 0.9992. 

EPA MRJD #s: 4947060 1 and 49470602 

PMRA # of document: Not available Page 5 of7 
Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 I 94 l 7) 

IV. Accuracy (Recovery) and Precision (Repeatability) 

Radiovalidation. No radiovalidation data have been submitted for method GRMOI0.02A. The 

extraction procedures used for this method are the same as those used for the established 

enforcement methodology, for which radiovalidation data were previously submitted and 

reviewed (refer to DP#s 233561 , etc., 2/20/98, G. Kramer); therefore, no additional data are 

required. 

Table B.5.2.1.2-2. Radiovalidation of the Pre-Registration Analytical Method for Plant Matrices 

Matrix I Analytc I Extraction Method I Radioactive Residues (ppm) I Extraction Efficiency(%) 

Not applicable 

Method validation. The method was adequately validated for the quantitation and confirmation 

ion transitions using samples of almond nutmeat and hulls, apple, tomato, and wheat forage, hay, 

and grain fortified with cyprodinil at 0.0 1 and 1.0 ppm. Recoveries were generally within the 

acceptable range of 70-120%. Mean recoveries (and relative standard deviations) for cyprodinil 

following fortification at 0.0 l and 0.1 ppm, respectively, in all matrices were: 73-86% ( 1.8-

8.4%) and 80-88% (2.0-11 %) for the quantitation transition and 79-88% (2.8-8.0%) and 78-86% 

(1.8- 12%) for the confirmation transition. 

Repeatability data were generated from five samples fortified at the LOQ and five samples 

fortified at lOx LOQ for each matrix. The relative standard deviations (RSDs) obtained for each 

fortification level were S l2%. Recovery and repeatability data are presented in Table B.5.2. 1.2-

3, below. 

Table B.5.2.1.2-3. Accuracy and Precision Data for Method GRM010.02A. 

Analytc Matrix Fortification 

Level (ppm) 

Cy prod in ii Almond 0.01 

m'.: 226-93 nutmeat 0.10 

(quantitation) Almond hulls 0.01 

0.10 

Apple 0.01 

0.10 

Tomato 0.01 

o. 10 

Wheat forage 0.01 

0. 10 

Wheat hay 0.01 

0.10 

Wheat grain 0.01 

0. 10 

EPA MRlD #s: 49470601 and 49470602 

PMRA # of document: Not available 

Concurrent Recovery (%) 

Individual 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 

RSD 

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 1-85 7. I 

72-86 7.5 

Page 6 of7 
Cyprodinil [PC Code 288202]/Syngenta Crop Protection, LLC [CGA2 I 94 J 7) 

T a ble B.5.2. 1.2-3. Accuracy and Precision Data for Method GRMOI0.02A. 

/\nalyte Matrix Fortification Concurrent Recovery (%) 

Level (ppm) Individual Mean Range 

Cyprodini l Almond 0.01 88. 88. 81. 83. 86 85 8 1-88 

Ill= 226-> 77 nutmeat 0. 10 9 1. 87. 81. 8-L 88 86 8 1-91 

(confirmation) Almond hulls 0.01 76.82. 75.80,84 79 75-84 

0. 10 83. 84. 8 1, 74. 79 80 74-84 

Apple 0.01 88. 80.89.87. 84 86 80-89 

0. 10 9 1. 87. 75, 76. 99 86 75-99 

Tomato 0.01 86,87,92. 86. 88 88 86-92 

0.10 91, 78. 8 1. 89. 80 84 78-91 

Wheat forage 0.01 85.96.83.82. 78 85 78-96 

0. 10 87.90.88. 80.87 86 80-90 

Wheat hay 0.01 78, 8.t. 77. 80. 82 80 77-84 

0. 10 87.84, 88, 87. 86 86 84-88 

Wheat grain 0.0 1 84.82. 75. 84. 73 80 73-84 

0. 10 79.83. 76.80. 71 78 71-83 

V. Limit of Quantitation 

T a ble B.5.2.1.2-4. Summary of Detection a nd Qua ntitation Limits for Method G RM010.02A. 

/\nalyte I LOD (ppm)1 I 

Cyprodin 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. defined as the lowest level of method validation: LLMV). 

VI. Conclusions 

LOQ (ppm)2 

0.01 

RSD 

(%) 

3.7 

.t.4 

4.8 

4.9 

4.3 

12 

2.8 

6.9 

8.0 

4.4 

3.6 

1.8 

6.6 

5.8 

The LC/MS/MS method GRMO I 0.02A was adequately validated for determining residues of 

cyprodinil in crops including tree nuts. The validated LOQ is 0.0 1 ppm. A confirmatory method 

is not required because the method monitors two ion transitions. 

B.5.2.2 

Not applicable 

B.5.2.3. 

Not applicable 

Analytical Methods for Foodstuff of Animal Origin (Livestock 

Matrices; Annex HA 4.3, Annex IHA 5.3) 

Multiresidue Methods 

EPA MRJ D #s: 4947060 1 and 49470602 

PMRA #of document: Not available Page 7 of 7 
Cyprodinil [PC Code 288202]/Syngenta Crop Protection, LLC [CGA2 l 9417] 

B.7.6 Residues Resulting from Supervised Trials 

(Annex IIA 6.3; Annex IHA 8.3) 

B.7.6.1 Residues in Target Crops 

B.7.6.1.1 Tree Nuts 

Document ID: MRID No. 49470603 

PMRA No. Not available 

Report: Mazlo. J. (2013) Difenoconazole/Cyprodinil EW (Al600lA) - Magnitude 

of the Residues of Cyprodinil in or on Almonds and Pecans as 

Representative Commodities ofTree Nuts, Group 14. USA 2012. Final 

Report. Report Numbers: TKO l 08966 and 68387. Unpublished study 

prepared by Syngenta Crop Protection, LLC. 128 p. 

Guidelines: EPA OCSPP Harmonized Test Guideline 860.1500 Crop Field Trials 

(August 1996) 

PMRA Regulatory Directive DIR98-02- Residue Chemistry Guideli nes, 

Section 9 - Crop Field Trials 

PMRA Regulatory Directive 0 IR20 I 0-05 - Revisions to the Residue 

Chemistry Crop Field Trial Requirements 

OECD Guideline 509 Crop Field Trial (September 2009) 

GLP Compliance: No deviations from regulatory requirements were reported which would 

have an impact on the validity of the study. 

Acceptability: The study is considered scientifically acceptable. The acceptability of this 

study for regulatory purposes is addressed in the forthcoming U.S. EPA 

Residue Chemistry Summary Do~ct D 5723. 

Evaluator: Thurston G. Morton, Chemist 

Registration Action Branch 4 

Health Effects Division (HED) (7509P) 

Note: This Data Evaluation Record (DER) was originally prepared under contract by Vcrsar, Inc. (6850 Vcrsar Center. 

Springfield, VA 22151 ; submit1ed 4/ 10/15). The DER has been reviewed by 1-!ED and revised to reflect current Oftice of 

Pesticide Programs (OPP) policies. 

EXECUTIVE SUMMARY 

Syngenta Crop Protection has submitted field trial data for cyprodinil on tree nuts. Five pecan 

field trials were conducted in the United States during the 2011 growing season in the North 

American Free Trade Agreement (NAFT A) Growing Zones 2 (GA; 2 trials), 4 (LA; 1 trial), 6 

(OK; l trial), 8 (OK; I trial), and four almond trials were conducted in Zone 10 (CA; 4 trials). 

The above field trial count excludes one CA almond field trial which the petitioner excluded 

from the study because the seasonal application rate exceeded the target rate. This trial is not 

addressed further herein. 

Each trial site consisted of one untreated plot and one treated plot reflecting four foliar broadcast 

applications made with the 2.09 lb ai/gal oil in water emulsion (EW) formulation of cyprodinil 

(Inspire Super® Fungicide), a multiple active ingredient (MAI) formulation which also contains 

EPA MRID #: 49470603 

PMRA # of document: Not available 

Page I of8 
Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2194 I 7] 

difenoconazole at 0.73 lb ai/gal. Data and information pertaining to difenoconazole are not 

addressed further herein. Applications were made at a rate of 0.317-0.338 lb ai/A/application at 

retreatment intervals (RTis) of 12-15 days using ground equipment in spray volumes of 69-208 

gal/ A for a total application rate of 1.30-1.34 lb ai/ A. A nonionic surfactant (NIS) or crop oil 

concentrate (COC) was added to the spray mixture for each application. Samples of pecan 

(nutmeat) and almond (nutmeat and hulls) were harvested at preharvest intervals (PHls) of 13-14 

days. Additional almond (nutmeat and hull) samples were collected from one trial at PHis of 0, 

5, 9, and 19 days to generate residue decli ne data. 

Samples were maintained frozen at the testing facilities, during shipping, and were stored frozen 

at the analytical laboratory until analysis. The maximum storage interval for samples between 

harvest and extraction was 298 days (9.8 months) for pecan (nutmeat) and almond (nutmeat and 

hulls). Samples were analyzed within 14 days of extraction. The petitioner indicated that 

storage stability data were available for tree nuts (Syngenta Study No. T003062-07); however, 

these data do not appear to have been reviewed by the agency. Acceptable storage stability data 

are available indicating that residues of cyprodinil are stable during frozen storage for up to 2 

years in/on a variety of crops including wheat ear and stalk (DP#s 233561, etc., 2/20/98, G. 

Kramer). These data are acceptable to support storage conditions and durations of samples from 

the submitted field trials. 

Samples were analyzed for residues of cyprodinil using high performance liquid chromatography 

with tandem mass spectrometric detection (LC/MS/MS) using method GRMOO 10.02A, with 

minor modifications. Acceptable method validation and concurrent recoveries were reported for 

samples fortified with cyprodinil at 0.01-10 ppm, thus validating the method. The limit of 

quantitation (LOQ; determined as the lowest level of method validation, LLMV) was 0.0 l 0 ppm. 

The fortification levels used in concurrent method recovery were adequate to bracket expected 

residue levels. Concurrent recoveries were corrected for apparent residues in controls (residues 

in controls were below the LOQ); residues in the treated samples were not corrected for apparent 

residues in controls. 

In tree nuts harvested at a PHI of 13-14 days following the last of four foliar broadcast 

applications of a 2.09 lb ai/gal EW formulation at a total rate of 1.30-1.34 lb ai/ A, individual 

sample (and per-trial average) residues of cyprodinil were <0.010-0.0408 (<0.0 I0-<0.0254) ppm 

in/on pecan (nutmeat), <0.010-0.0146 (<0.010-0.0131) 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 cyprodinil generally declined in/on almond nutmeat 

and hulls with increasing PHI. 

I. MATERIALS AND METHODS 

A. MATERIALS 

Table B.7.6.1.1 - 1. Nomenclature for Cyprod inil 

Common name Cyprodinil 

Id entity 2-pyrimidinamine. 4-cyclopropyl-6 -mc1hyl-.V-phenylCAS no. 121552-61-2 

EPA MR.JD #: 49470603 

PM RA # of document: Not available 

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Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 I 94 I 7) 

Table B.7.6.1.J-l. Nomenclature for Cyprodinil 

Company experimental name ICGA2 194 17 

Other synonyms (if a1>plicable) I Not applicable 

H ()NYN" 

N _,,,-:::. 

CH3 

B. Study Design 

1. Test Procedure 

Five residue trials were conducted on pecans and four residue trials were conducted on almonds 

in the United States reflecting foliar broadcast applications of the 2.09 lb ai/gal EW formulation 

(Inspire Super® Fungicide) of cyprodinil during the 20 11 growing season. Field trial locations 

by NAFTA growing zone are summarized in Table B.7.6.1.1-2. 

Table B.7.6.1.1 -2. T ria l Numbers a nd Geographica l Locations. 

Crop No. NAFTA Growing Zone Total Trials I 2 3 4 5 6 7 8 9 10 11 12 

Almonds Sub. 4 4 

Rcq.1 5 5 

Pecans Sub. 2 I I I 5 

Req. 1 2 I I I 5 1 As per OCSPP 860.1500, Tables 2 and 5 for almond and pecan as representative commodities of the tree nut group. 

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

Table B.7.6.1.1-3. Study Use Pattern. 

Location: City, End-use Method of Application: Volume Rate per Retreaunent Total Rate Surfactant/ 

State: Year (Trial Product1 Timing of Application (gal/A) Application Interval (lb ai/A) Adjuvant2 

ID) (lb ai/A) (days) 

Pecan trials 

Chula. GA: 2011 2.09 lb I. Foliar broadcast: BBCH 80 207.75 0.323 -- 1.31 NIS 

(TK0059529-0 I) ai/gal 2. Foliar broadcast: BBCl-1 80 135.50 0.330 13 NIS 

3. Foliar broadcast: BBCI I 81 137.69 0.327 15 NIS 

4. Foliar broadcast: BBCl-1 85 130.66 0.329 13 NIS 

Pineview. GA: 2.09 lb I. Foliar broadcast: BBCl-I 80 136.40 0.331 -- 1.32 coc 

20 11 ai/gal 2. Foliar broadcast: BBCH 83 127.3 1 0.329 15 coc 

(TK0059529-02) 3. Foliar broadcast: BBCH 85 128.99 0.331 13 coc 

4. Foliar broadcast: BBCH 85 123.43 0.333 14 coc 

EPA MR.ID #: 49470603 

PMR.A # of document: Not available 

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Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 I 94 17) 

Table B.7.6.1.1-3. Study Use Pattern. 

Location: City, End-use Method of Application; Volume 

State: Year (Trial Product' Timing o f Application (gal/A) 

ID) 

Alexandria. LA: 2.09 lb I. Foliar broadcast: BBCH 85 70.80 

20 11 ai/gal (hard dough) 

(TK0059529-03) 2. foliar broadcast: BBCI I 85-88 79.87 

(approximately 10% beginning 

shuck split) 

3. Foliar broadcast: BBCH 85-88 80.89 

(approximately 25% beginning 

shuck split) 

4. Foliar broadcast: BBCI I 93 83.46 

(progressive shuck split) 

Madill. OK: 2011 2.09 lb I. foliar broadcast: BBCll 80 76.97 

(TK0059529-04) ai/gal 2. Foliar broadcast: BBCH 85 73.5 1 

3. Foliar broadcast: BBCH 89 69. 13 

4. Foliar broadcast: BBCH 93 74.32 

Altus. OK; 2011 2.09 lb 1. Foliar broadcast: 13BCH 79 132.83 

(TK0059529-05) ai/gal 2. Foliar broadcast: BBCI I 85 135.58 

3. Foliar broadcast: BBC! I 89 133.04 

4. Fol iar broadcast: BBCH 93 135. 14 

Almond trials 

Strathmore. CA: 2.09 lb I. Foliar broadcast; BBCI I 79 

20 11 ai/gal (fruit at full size) 

(TK0059529-07) 2. Foliar broadcast: BBCI I 79 

(fruit at 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 

(TK0059529-08) ai/gal 2. Foliar broadcast: not spccilicd 

3. Foliar broadcast: not specified 

4. Foliar broadcast: not specified 

Dinuba. CA: 2.09 lb I. Foliar broadcast: BBCH 79 

20 11 ai/gal (fruit at full size) 

(TK0059529-09) 2. Foliar broadcast: BBCI I 79 

(fruit at full size) 

3. Foliar broadcast: BBCH 79 

(fruit at full size) 

4. Foliar broadcast: BBCH 79 

(fruit at full size) 

Madera, CA: 2.09 lb I. Foliar broadcast: BBCH 79 

2011 ai/gal (pre-hull split) 

(TK0059529- I 0) 2. Fo liar broadcast: BBCI I 79 

(pre-hull split) 

3. Foliar broadcast: BBCH 8 1 

(hull split) 

4. Foliar broadcast: BBCH 81 

(drying hull) . . 1 A 2.09 lb ai/gal EW fonnulauon (Inspire Super® fung1c1de) . 2 NIS = onionic surfactant: COC = Crop oil concentrate. 

EPA MRID #: 49470603 

PMRA #of document: Not available 

7 1.37 

7 1.36 

72.76 

72.77 

149.52 

149.47 

149.58 

149.20 

154.58 

184.26 

204.87 

205.62 

82.72 

81.77 

8 1.5 1 

81.14 

Rate per 

Application 

(lb ai//\) 

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 

0.330 

0.330 

0.33 1 

0.330 

0.33 1 

0.33 1 

0.33 1 

0.330 

0.328 

0.327 

0.329 

0.329 

0.338 

0.334 

0.333 

0.33 1 

Rctrcatmcnt Total Rate Surfactant/ 

Interval (lb ai/A) Adjuvant2 

(days) 

-- 1.32 N IS 

14 IS 

14 I IS 

14 N IS 

-- 1.30 coc 

14 coc 

14 coc 

15 coc -- 1.30 NIS 

14 N IS 

15 NIS 

12 NIS 

-- 1.32 NIS 

14 NIS 

14 IS 

14 IS 

-- 1.32 coc 

14 coc 

14 coc 

14 coc -- 1.31 NIS 

14 IS 

14 11S 

14 r1s 

-- 1.34 coc 

14 coc 

14 coc 

14 coc 

Page 4 of 8 
Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 I 9417) 

Pecans and almonds were grown and maintained according to typical agricultural practices. 

Irrigation was used to supplement rainfall at Trials 01, 03, and 07-10. No unusual weather 

conditions were reported to have adversely affected crop growth or yields during the study. 

Sample Handling and Preparation 

Single untreated and duplicate treated samples of pecan (nutmeat) and almond (nutmeat and 

hulls) were collected at each trial. Samples were harvested at PHls of 13-14 days. Additional 

almond (nutmeat and hull) samples were collected from one trial at PHis of 0, 5, 9, and 19 days 

to generate residue decline data. Samples were placed in frozen storage ( <-10 °C) at the field 

sites. Samples were shipped frozen via freezer truck or overnight courier within 0-38 days of 

harvest to the analytical laboratory, Syngenta Crop Protection, LLC (Greensboro, NC). At the 

analytical laboratory, samples were homogenized in the presence of dry ice and were stored 

frozen (-20 °C) until extraction for analysis. 

2. Description of Analytical Procedures 

Samples were analyzed for residues of cyprodinil by LC/MS/MS method GRM 0010.02A with 

minor modifications. A complete description of the method, including details of minor 

modifications, was included in the submission. Modifications included the following: minor 

materials and instrument changes; removal of acidification step with HCl to adjust pH; and 

following elution residues were diluted with 0.1 % ammonium acetate:ACN (90: 10, v:v). A 

complete description and method validation data for this method are currently under review 

under DP# 425723 (refer to 49470601.der in Section B.5.2). 

Briefly, samples of were extracted with methanol:water (80:20, v:v) for 1 hour. The extract was 

centrifuged then filtered, and an aliquot was combined with 0.1 % ammonium acetate and applied 

to a Waters HLB solid phase extraction (SPE) 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) for analysis by LC/MS/MS. 

The LOQ (determined as the lowest level of method validation; LLMV) was 0.010 ppm. The 

LOD (limit of detection) was not reported. 

II. RESULTS AND DISCUSSION 

Method perfonnance was evaluated during method validation and by use of concurrent recovery 

samples. For method validation, samples of untreated almond (nutmeat and hulls) were 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 (nutmeats), 0.01-0.1 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 considered va lid for the analysis of cyprodinil residues in/on tree nut matrices 

(Table B. 7.6.1.1-4). The fortification levels bracketed the measured residues. Concurrent 

recoveries were corrected for apparent residues in controls. 

EPA MRJD #: 49470603 

PMRA # of document: Not available 

Page5of8 
Cyprodinil [PC Code 288202]/Syngenta Crop Protection, LLC [CGA2 I 9417) 

The detector response was linear (coefficient of determination, r2 2;:0.9946) within the range of 

0.02-0.5 ng/mL. Representative chromatograms of control samples, fortified samples, and 

treated samples were provided. The control chromatograms generally had no peaks of interest 

above the chromatographic background. The fortified sample chromatograms contained only the 

analyte of interest, and peaks were symmetrical and well defined. Apparent residues in controls 

were below the LOQ (<0.010 ppm). The reported residue values were not corrected for apparent 

residues in controls. 

Table B. 7.6.J.1 -4. Summary of M e thod Validation and P rocedura l/Concurrent Recoveries of Cyprodinil 

from Tree Nu ts. 

Matrix Fortification Sample size Recoveries1 Mean ± Std. Dev. 

Level (ppm) (n) (%) (%) 

Method validation 

Almond nutmeat 0.01-1.0 6 71-83 75 ± 5.1 

Almond hulls 0.01-1.0 6 74-1 05 85 ± 12 

Concurrent recoveries 

Almond nutmeat 0.01-0.10 ..i 83-97 88 ± 6.7 

Almond hulls 0.0 1-1 0 5 75-89 82 ± 5.8 

Pecan nutmeat 0.01-1.0 4 70-92 8 1 ± 11 

1 Concurrent recoveries were corrected for apparent residues in controls. 

Samples were stored frozen for a maximum of 298 days (9.8 months) from harvest to extraction 

(Table B.7.6.1 .1-5). Samples were analyzed within 14 days of extraction. The petitioner 

indicated that storage stability data were available for tree nuts (Syngenta Study No. T003062-

07); however, these data do not appear to have been reviewed by the agency. Acceptable storage 

stability data are available indicating that residues of cyprodinil are stable during frozen storage 

for up to 2 years in/on a variety of crops including wheat ear and stalk (DP#s 233561 , etc., 

2/20/98, G. Kramer). The available data are adequate to support the storage conditions and 

durations for samples from the submitted crop field trials. 

Table B.7.6.1.1-5. S ummary of Storage Cond itions. 

Matrix Storage Actual Storage Duration ' Interval of Demonstrated Storage Stability 

(RAC) Temperature (°C) 

Pecan nutmeat <-I 0 at the field 288-298 days The petitioner indicated that storage stability data were 

sites: -20 at the (9.5-9.8 months) available for tree nuts (Syngenta Study 1o. T003062-07): 

Almond nutmeat analytical 242-294 days however. these data do not appear to have been reviewed by 

laboratory (8.0-9.7 months) the agency. Acceptable storage stability data are available 

Almond hulls 244-296 days 

indicating that residues of cyprodini l arc stable during frozen 

(8.0-9.7 months) storage for up to 2 years in/on a va riety of crops inc luding 

wheat car and stalk2• 

1 Interval from harvest to extraction. Samples were analyzed within 0-1 4 days of extraction. 2 DP#s 23356 1. etc .. 2/20/98. G. Kramer. 

The results from the submitted field trials are presented in Tables B.7.6.1.1-6 and B.7.6.1.1-7. In 

tree nuts harvested at a PHI of 13-14 days following the last of four foliar broadcast applications 

of a 2.09 lb ai/gal EW formulation at a total rate of 1.30-1.34 lb ai/ A, individual sample (and pertrial average) residues of cyprodinil 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). 

EPA MRID #: 49470603 

PMRA # of document: Not available 

Page 6 of8 
Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 l 94 l 7) 

In the one residue decline trial, residues of cyprodinil generally declined in/on almond nutmeat 

and hulls with increasing PHI. 

Table B.7.6.1.1-6. Resid ue Data from Tree Nuts Field Trials with Cyprodinil.1 

Location: City. Zone Tree Nut/ Matrix Rate PHI Residues2 (ppm) [Average] 

State; Year (Trial Variety (lb ai/A) (days) 

ID) 

Chula, GA; 2011 2 Pecan/ Nutmeat 1.31 14 <0.010, 0.0408 (<0.0254] 

(TK0059529-01) Sumner 

Pineview, GA; 2011 2 Pecan/ Nutmeat 1.32 13 0.0107. <0.010 (<0.0104] 

(TK0059529-02) Dcsireable 

Alexandria, LA: 4 Pecan/ Creek Nutmeat 1.32 13 0.0118, <0.010 [<0.0109] 

201 1 

(TK0059529-03) 

Madill. OK; 2011 6 Pecan/ Nutmeat 1.30 13 <0.0 10, <0.010 [<0.0 10] 

(TK0059529-04) Wichita 

Altus. OK: 2011 8 Pecan/ Nutmeat 1.30 14 <0.010, <0.010 [<0.0 10) 

(TK0059529-05) Wichita 

Strathmore, CA: 10 Almond/ Nutmeat 1.32 14 0.0115, 0.0105 (0.01 10) 

201 1 Carmel Hulls 6.46, 4.49 (5.48] (TK0059529-07) 

Chico. CA; 20 11 10 Almond/ Nutmeat 1.32 14 <0.010. <0.010 [<0.010] 

(TK0059529-08) Price Hulls 0.707, 0.707 (0.707) 

Dinuba, CA: 201 1 10 Almond/ Nutmeat 1.31 14 <0.010, <0.010 [<0.010] 

(TK0059529-09) Carmel Hulls 3.54. 3.89 (3. 72] 

Madera. CA; 2011 10 Almond/Non Nutmeat 1.34 0 0.0238 [0.0238] 

(TK0059529- I 0) Parcil 5 0.0239 (0.0239] 

9 0.0 171 [0.0171] 

14 0.0115, 0.0146 [0.0131] 

19 <0.010 (<0.010) 

Hulls 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] 

1 A 2.09 lb a1/gal EW formulation was used. 

"The LOQ was 0.01 ppm: the LOO was not reported. Per-trial averages were calculated by the study reviewer. 

Table B.7.6.1.1-7. Summary of Residues from Tree Nut Field Trials with Cyprodinil. 

Crop Matrix Total PHI n' Residues (ppm) 

Application (days) Min.2 Max.

2 LAFT3 HAFT3 Median3 Mcan3 SD3 

Rate 

(lb ai/A) 

Pecan nutmeat 1.30-1 .32 13-1 4 5 <0.010 0.0408 <0.0 10 <0.0254 0.0 104 0.0133 0.00676 

Almond nutmeat 1.31-1.34 14 4 <0.010 0.0146 <0.0 10 0.0131 0.0 105 0.0 11 0 0.00 144 

Almond 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 samples. 3 Values based on per-trial averages. LAFT =lowest average field trial, HAFT = highest average fie ld trial, SD = standard 

deviation. For computation of the LAFT, I IAFT. median. mean. and standard deviation, values <LOQ were assumed to be at the 

LOQ (0.010 ppm). 

EPA MRJD #: 49470603 

PMRA # of document: Not available 

Page 7 of8 
Cyprodinil [PC Code 288202)/Syngenta Crop Protection, LLC [CGA2 I 9417) 

lll. CONCLUSIONS 

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 applications of a 2.09 lb ai/gal EW 

formulation at a total rate of 1.30-1.34 lb ai/ A, individual sample (and per-trial average) residues 

of cyprodinil 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 cyprodinil generally declined in/on almond nutmeat 

and hulls with increasing PHI. 

An acceptable method was used for residue quantitation, and adequate storage stability data were 

available to support sample storage durations and conditions. 

REFERENCES 

DP#s 233561, etc., 2/20/98, G. Kramer 

EPA MRJD #: 49470603 

PMRA # of document: Not available 

Page 8 of8