### Propiconazol e 122101 Summary of Analytical Chemistry and R esi due Data DP # 400 030



### UNITED STATES ENV I RONMENTAL PROTECTION AGENCY WASHINGTON, 

## D.C. 20460

OFFICE OF CH EMICAL SAFETY AND POLLUTI O N PREVENTION


## MEMORANDUM

Date: 2/27 /13

Subject: Propiconazole. Amended Use on Cereal Grain s. Analytical Me thods and Residue Data.

P C Code : 1 221 0 1 Deci s i on N o.: 46 0659

P e tition No.: 2F7975 Ri sk Ass e ss ment Type: Chemistry TXR No.: NA MRID No. 48681701, 4868170 2, 48681 703
, 48681704, 4868 1 70 7



### Reviewe r:

Through:

To: Thurston G. M o rt o n , Che mi st Risk Ass ess ment Branch 4 Health Effects Division (7509P)

Susan Hwnmel

, Senior Scien t ist Eli ssa Reaves
, PhD, Branch Chie f Ri s k Assessment Branch 4 Heal t h E f fects Di v ision (7509P)

Heath er Garvie Fungicide Branch Regi s tration Division (7505P)

Executive Summary T)P Barco de : D400030 R egis tration No.: 

### I 00-617
, 

### I 00

- 11 7 8, 

### and I 00- 1324 R egulatory Action : Amended S e ction 3 C ase No.: 3125 CAS No.: 60207-90-1 40 CFR: 1 80.434



### Pr o piconazole i s a triazo l e-type fungicide (Gro up 3) that provides broad spect rum disease contr ol

on a variety of c r op s

. Tol erance s inion plant and anima l commodit ies are currently establi s h ed for the combin ed resid ue s of p r opico naz o l e, 1- [[ 2

- ( 2, 4

- di chlorophenyl)-4

- propyl -1
, 3-dioxolan

- 2- yl]methyl)-1 

## H-1

, 2
, 4

- triazole, and its 

### metabo li tes determined as 

### 2
, 4-d i ch loro b enzoic acid (2,4- DCBA) and expressed as parent (40 CFR § 18 0.434]. Tole r an c e s o n p la nt commodities ra nge from 0

. 1 ppm to 40 ppm in/on grass straw , an d toleranc

- es on animal commodities ran ge fr o m 0.05 ppm in milk to 2.0 ppm 

### in liver and ki dney of livestoc k.

Page I of 32

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 2 of 32 Syngenta has submitted a request to amend the us e of propiconazole using Tilt (EPA Reg. No. 100-617), QuiltTM (EPA Reg. No. 100-1178), an d QuiltXcelTM (EPA Reg. No. 100-1324) to cereal grains.

Syngenta is proposing to amend the use pattern by reducing the pre-harvest interval (PHI) to 7 days for forage and hay of cereal grains. In conjunction with the requested amended uses, Syngenta has submitted a petition, PP#2F7975, for the establishment of tolerances for the combined residues of the fungicide propic onazole 1-[[2-(2,4-dichlo rophenyl)-4-propyl-1,3- dioxolan-2-yl]methyl]-1H-1,2,4-triazole and its metabolites determined as 2,4-dichlorobenzoic acid and expressed as parent compound, in or on the following commodities:

Barley, hay ............................................................................ 30 ppm Barley, straw ......................................................................... 20 ppm Barley, grain ............................................................................ 3 ppm Rye, forage .............................................................................. 9 ppm Rye, straw ............................................................................... 9 ppm Oats, forage ............................................................................. 4 ppm Oats, hay ............................................................................... 15 ppm Oats, grain ............................................................................... 3 ppm Wheat, forage ........................................................................ 15 ppm Wheat, hay ............................................................................ 30 ppm Wheat, straw ......................................................................... 20 ppm Grain, aspirated fractions .................................................... 108 ppm

Note: This review only addresses the proposed uses for propiconazole onl y. Related issues for co-ingredient azoxystrobin in Quilt® Xcel Fungicide, (EPA Reg. No. 100-1324) will be discussed in a separate memo.

The Codex Alimentarius Commission has estab lished several maximum residue limits (MRLs) for propiconazole in/on various raw agricultura l commodities. In addition, both Canada and Mexico have established MRLs for propiconazo le in/on various commodities. The Codex and Mexican MRLs are expressed in terms of propiconazole per se . The Canadian MRLs are expressed in terms of combined residues of propiconazole and its metabolites containing the 2,4- DCBA moiety. Codex has an MRLs for straw an d fodder of barley, rye, and wheat along with MRL for barley grain. The U.S. cannot harmonize at this level due to the use pattern registered in the U.S along with the CODEX tolerance expre ssion. Canada has MRLs for barley, grain and oats, grain. The U.S. cannot harmonize at this leve l due to the use pattern registered in the U.S but will be harmonized on the tolerance expression for Canada only.

The data are adequate and support the proposed amended use pattern for propiconazole.

A GC method using flame ioniza tion detection (Method AG-354) is available for determining residues of propiconazole per se in/on plant commodities, and has an LOQ of 0.05 ppm. In addition, Multiresidue Methods Sec tion 302 can also be used to determine parent propiconazole

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 3 of 32 in both plant and animal matrices. The valid ated LOQ for combined residues was 0.05 ppm in all raw and processed commodities.

Samples were analyzed using adequate analytical methods and the sample storage intervals are supported by the available storage stability data. Adequate storage stability data are available indicating that residues of pr opiconazole are stable at ≤ -15 C from 4-39 months in a variety of commodities.

The submitted processing studies are adequate in providing a determination of residue concentration factors for propiconazole in whea t processed commodities. The processing data indicate that propiconazole a nd propiconazole and metabolites may concentrate in AGF, bran, and germ (average processing factors of 36- 90x, 1.6-2.3x, and 1.6-2.0x) but do not concentrate in flour, middlings, and shorts (average processing factors of <0.22-<0.31x, <0.41-0.54x, and <0.46-0.66x, respectively).

Adequate confined rotational crop studies are available indicating that the residues in rotational crops are similar to the primary crops. The c onfined studies also support the 105-day plant-back interval (PBI) currently listed on product labels for crops w ithout direct uses. Currently, propiconazole tolerances for inadvertent residues in/on al falfa forage and hay at 0.1 ppm.

Residue Chemistry Deficiencies

Syngenta has submitted a request to add additional uses of propiconazole using Tilt (EPA Reg. No. 100-617), QuiltTM (EPA Reg. No. 100-1178), and QuiltXcelTM (EPA Reg. No. 100-1324).

C onclusion : No deficiencies were noted in this request that would preclude granting the proposed amended use.

Regulatory Recommendations and Residue Chemistry Deficiencies

HED has examined the residue chemistry database for propiconazole. HED has determined that the current tolerance expression fo r plant and livestock commodities is not appropriate and has recommended that the to lerance expression be revised to HED guidance on tolerance expressions (S. Knizner, 2009)

. We now conclude the tolerance expression should be as follows: Tolerances are established for residues of propiconazole, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance le vels specified below is to be determined by measuring only those propiconazole residues convertible to 2,4- dichlorobenzoic acid (2,4- DCBA), expressed as the stoichiometric equivale nt of propiconazole, in or on the commodity in the table below.

Pending submission of a revised Section F (s ee requirements below), there are no residue chemistry issues that would preclude granting an unconditional registra tion for the requested amended use of propiconazole on sugarcane or establishment of tolerances for residues of propiconazole in/on the following commodities:

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 4 of 32 Barley, grain ......................................................................... 3.0 ppm Rye, forage ........................................................................... 9.0 ppm Oat, forage ............................................................................ 4.0 ppm Oat, hay ................................................................................. 15 ppm Oat, grain.............................................................................. 3.0 ppm Barley, bran .......................................................................... 6.0 ppm Rye, straw ............................................................................. 10 ppm Grain, aspirated fractions .................................................... 110 ppm

A human health risk assessment is forthcoming.

860.1550 Proposed Tolerances

 The proposed tolerances for Grain, aspirated fractions must be increased to 110 ppm. The tolerance for Barley, bran must be incr eased to 6.0 ppm and the existing tolerance for Rye, straw must remain at 10 ppm.

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 5 of 32 Background


### Propiconazole is a triazole-type f ungicide (Group 3) that provides broad spectrum disease control through inhibition of sterol biosynthe sis in fungi. It is registered to Syngenta for the control of fungal diseases on a variety of crops. It is fo rmulated as emulsifiable concentrates under the trade names (EPA Reg. No. 100-617) and Qu iltXcelTM (EPA Reg. No. 100-1324). One formulation also contains a co-ingredient, i.e ., azoxystrobin. However, this memo will only address propiconazole.

Permanent tolerances are currently established for the combined residu es of propiconazole, 1- [[2-(2,4-dichlorophenyl)-4-pr opyl-1,3-dioxolan-2-yl]methyl]-1 H -1,2,4-triazole, and its metabolites determined as 2,4-DCBA and expressed in parent equivalents, at levels ranging from 0.1 ppm on numerous plant commodities to 40 ppm in/on grass straw [40 CFR §180.434(a)]. Permanent tolerances are also established for the combined residues of propiconazole and its metabolites determined as 2,4-DCBA at 0.05 ppm in fat, meat, and meat byproducts (except liver and kidney) of livestock, 2.0 ppm in liver and ki dney of livestock, and at 0.05 ppm in milk; however, no tolerances have been established fo r eggs and poultry commodities. Time-limited tolerances are established for combined propi conazole residues in/ on a variety of plant commodities at level of 2.0 ppm in/on nectarin e and peach and 10 ppm in/on avocado [40 CFR §180.434(b)]. In addition, tolerances with region al restrictions have been established for combined propiconazole residues at 1.0 ppm in/on cranberry and at 0.5 in/on wild rice grain[40 CFR §180.434(c)]. Tolerances with inadvertent residues have been established for combined propiconazole residues at 0.1 ppm in/ on alfalfa forage and alfalfa hay.

Table 1. Nomenclature of Propiconazole
Compound

N N N

O O
Cl Cl

Common name Propiconazole Company experimental names CGA-64250 IUPAC name 1-[2-(2,4_dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1 H -1,2,4_triazole CAS name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1 H -1,2,4-triazole
CAS # 60207-90-1 End-use products/EP 3.6 lb/gal EC (EPA Reg. Nos. 100-617

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 6 of 32

Table 2. Physicochemical Properties of Technical Grade Propiconazole.

Parameter Value Reference Boiling point 120 C at 1.9 Pa, >250 C at 101.325 kPa MRID No. 43698701 pH 4.9 at 25 C (1% aqueous dispersion) MRID No. 43698701 Density 1.289 g/cm 3 at 20 C MRID No. 43698701 Water solubility 0.10 g/L at 20 C MRID No. 41720301

Solvent solubility (temperature not specified) Completely miscible in ethanol, acetone, toluene and n-octanol. hexane = 47 g/L MRID No. 42030201 Vapor pressure 4.2 x 10 -7 mm Hg at 25 C MRID No. 41720301 Dissociation constant (pK a ) 1.09 MRID No. 43698701 Octanol/water partition coefficient Log(K OW ) 3.72 at pH 6.6 and 25 C MRID No. 43698701 UV/visible absorption spectrum ( 8 max, nm) Not available MRID No.: 40583703



### 860.1200 Directions for use

Several current end-use product containing propiconazole that is registered for use on feed/food crops is marketed under the trade names T ilt® Fungicide (EPA Reg. No. 100-617), QuiltTM (EPA Reg. No. 100-1178), and QuiltXcelTM (EPA Reg. No. 100-1324) (See Table 3.).

1. 45 day for animal feed only. 2. 7 day PHI for forage and hay only.



### 860.1300 Nature of the Residue – Plants.

The nature of propiconazole residues in plan ts is adequately u nderstood (DP D329394, Y. Donovan, 6/15/06). These data indi cate that the major metabolic pathway in plants appears to involve hydroxylation of the n-propyl group on th e dioxolane ring of the cis/trans isomers of propiconazole, with subsequent conjugation to sugars. A possibl e alternative pathway involves reductive deketalization of the dioxolane ring and sugar conjugati on of the resulting metabolite. Table 3. Label Directions for Proposed Uses of Propiconazole

Product EPA Reg. No. Use Site Target Application Methods Maximum Application Rate (lb ai/A) PHI (day) REI (hr) Use Directions/ Limitations

Tilt ® Fungicide EC (100- 617) Cereal Grains: Wheat; Barley; Oats; Rye;

Triticale Broadcast Foliar Aerial Chemigation Groundboom 0.056 - 0.113 (2 app. /season) 14

7 (Forage

and Hay) 2 12 hr A minimum
retreatment interval (RTI) of 14 days is proposed.

Quilt Xcel ® Fungicide EC (100- 1324) 0.056-0.112 (2 app. /season) A minimum
retreatment interval (RTI) of 14 days is proposed. Contains azoxystrobin also. Quilt ® Fungicide EC (100- 1178) 0.056 - 0.114 (2 app. /season)

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 7 of 32 The alkyl bridge between the phenyl and tr iazole rings is metabolized and free 1 H -1,2,4-triazole is released. The free triazole is readily conjugated with the am ino acid, serine/alanine, forming triazole aniline which is further metabolized to triazole acetic acid possibly through the intermediate formation of triazole lactic acid.

HED has concluded that the residues of con cern should include propi conazole and all its metabolites containing the 2,4-DCBA moiety, includi ng conjugates for dietary risk assessment of food, as virtually all the residue data have been generated us ing a common moiety method that converts parent and all of the meta bolites of concern to 2,4-DCBA.

The tolerance expression should be am ended to include only propiconazole per se because 1) there are a number of pesticides that have 2,4-DCBA as common metabolite, and an enforcement agency may not be able to determine if residues are due to misuse of propiconazole or the proper use of other pesticides contai ning 2,4-DCBA; 2) propiconazole per se can be detected by FDA multiresidue methods; and 3) inclusion of only parent allows harmonization with the residue definition for the Codex MRLs. However, this will be done at a later time.

860.1300 Nature of the Residue – Livestock.

The nature of propiconazole residues in livesto ck is adequately understood based on acceptable goat and poultry metabolism studies (DP D 329394, Y. Donovan, 6/15/06). The Agency concluded that parent and all metabolites conve rtible to 2,4-DCBA are residues of concern for risk assessment, as the analytical method is a common moiety method th at detects all residues convertible to 2,4-DCBA. However, for tolera nce enforcement purposes, the current tolerance expression should be amended to include only propiconazole per se.
860.1340 Residue Analytical Methods.

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a high performance liquid chromatography met hod with tandem mass spectrometry detection (LC/MS/MS), Morse Laboratories Meth-180. The lim it of quantitation (LOQ; determined as the lowest limit of method validation; LLMV) was 0.01 ppm. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas chromatography with mass select ive detection (GC/MSD), Nova rtis Crop Protection method AG-626. This is a common moiety method in wh ich all residues of c oncern are converted by base hydrolysis and oxidation to 2,4-DCBA, then de termined as the 2,4-DCBA methyl ester, and reported in propiconazole equivalents. The LOQ (determined as the LLMV) was 0.05 ppm. Samples were analyzed for the triazole metabolit es 1,2,4-triazole (T), tria zole alanine (TA), and triazole acetic acid (TAA) using LC/MS/MS, Morse Laboratories Meth-160, Revision #2. The LOQs (determined as the LLMVs) were: 0.01 ppm for T in all matrices, 0.02, 0.06, and 0.01 ppm for TA in rye forage, grain, and straw, respectively, and 0.01 ppm fo r TAA in forage and 0.03 ppm in grain and straw. Th e methods were adequate for da ta collection based on acceptable concurrent recovery data. The fortification levels used in co ncurrent method recovery were adequate to bracket expected resi due levels. Concurrent recoveri es were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 8 of 32 GLN 860.1360: Multiresidue Methods

The FDA PESTDATA database (PAM Volume I, Appendix I) indicates th at propiconazole is completely recovered (>80%) using Multiresi due Methods Section 302. The recovery of propiconazole metabolites CGA-91305, CGA-11 8244, and 1,2,4-triazole is variable using Section 302. Propiconazole and metabo lites CGA-91305, CGA-118244, and 1,2,4-triazole are not recovered using Multiresidue Methods Sections 303 and 304.

860.1380 Storage Stability. ( 48681707.der.doc)



### Samples were stored frozen (<-10 °C at prepara tion facility and <-20 °C at analytical laboratory) from collection to analysis for up to 18 months . Previously submitted storage stability data indicate that weathered residue s of propiconazole and its meta bolites are stable for up to 38 months at -20 oC in/on grass forage and straw (DP# 210742, 3/15/95, M. Rodriguez). In addition, a storage stability study was submitted w ith this petition. Th e study results indicate that residues of propiconazole are stable under frozen storage conditions (-20 ± 5°C) for up to 24 months in/on sugar beet tops a nd root, barley grain, and apple, and for up to 30 months in/on soybean. Storage stability data for the triazole metabolites were not provided in this submission; however, the U.S. Triazole Task Force (USTTF), whos e members include Syngenta Crop Protection, Inc. among others, has submitted a multi-year storage stab ility study for the triazole metabolites in representative crop matrices and processe d commodities (MRID 47606601) which was reviewed by HED and found acceptable (D. Drew, D363016, 1/12/ 12). No additional data will be required for the triazole metabolites.

860.1400 Water, Fish, and Irrigated Crops

This guideline requirement is not releva nt to the proposed use for propiconazole.

860.1460 Food Handling

This guideline requirement is not relevant to the proposed use for propiconazole.

860.1480 Meat, Milk, Poultry, and Eggs

The amended use on cereal grains will change the pr evious dietary burden which is in the table below. However, livestock tolerances will need not be amended.

HED has issued a memo entitled, “Revisions of F eedstuffs in Table 1 of OPPTS Test Guideline 860.1000 and Guidance on Constructing Maximum R easonably Balanced Diets (MRBD)” in June 30, 2008 which includes revised definitions for the Table 1 reference animals, and refinement of feedstuffs avai labilities and percentages fed. The livestock dietary burdens calculated by the revised guidelines are 9.8 ppm for beef and 18.5ppm for dairy cattle, 1.9 ppm for swine and 2.2 ppm for poultry.

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 9 of 32 T able 4. Calculation of Maximum Reasonably Balanced Dietary Burdens of Livestock for Propiconazole Residues.

Feed Commodity % Dry Matter 1 % Diet 1 Current or Recommended Tolerance (ppm) Dietary Contribution (ppm) 2
Beef Cattle Grass, hay [R] 88 15 40 6.8 Corn field, grain [CC] 88 80 0.3 0.27 Aspirated grain fractions [CC] 85 5 110 6.5 Soybean seed [PC] 89 5 2.0 0.11 TOTAL 100 13.7 Dairy Cattle Grass, hay [R} 88 30 40 13.6 Corn, field, stover [R] 83 15 25.0 4.52 Corn, field, grain [CC] 88 45 0.3 0.15 Soybean seed [PC] 89 10 2.0 0.22 TOTAL 100 18.5 Poultry Wheat grain [CC] 89 55 0.5 0.17 Rice, grain [CC] 88 20 7.0 1.4 Soybean, seed [PC] 89 25 2.0 0.50 TOTAL 100 2.1
Swine Corn field, grain [CC] 88 65 0.3 0.20 Rice, grain [CC] 88 20 7.0 1.4 Soybean, seed [PC] 89 15 2.0 0.30 TOTAL 100 1.9

1 Table 1 (OPPTS Guideline 860.1000).
2 Contribution = ([tolerance /% DM] X % diet) for beef and da iry cattle; contribution = ([toler ance] X % diet) for poultry and

swine. NA = not applicable



### .

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 10 of 32 860.1500 Crop Field Trials ( 48681701.der.doc, 48681702.der.doc , 48681703.der.doc, 48681704.der.doc)


### Field trials were submitted supporting the amende d uses for propiconazole. The results from these studies are discussed in the appropriate data evaluation report (D ER) and summarized in the following tables.

TABLE C.4. Summary of Residue Data from Barley Crop Field Trials with Propiconazole. Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Barley Hay Propiconazole 0.2188- 0.2311 7 9 0.436 4.46 0.436 4.19 1.70 1.77 1.25 Propiconazole and Metabolites 9 2.08 13.1 2.08 11.9 4.27 6.13 3.95

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.05 0.210 <0.056 0.197 0.070 0.089 0.045
TAA 9 <0.02 0.065 <0.02 0.061 0.022 0.033 0.017 Propiconazole 14 9 0.157 2.10 0.175 1.72 0.483 0.671 0.509 Propiconazole and Metabolites 9 1.73 6.61 1.78 5.87 2.85 3.53 1.42

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.05 0.184 <0.05 0.180 0.065 0.084 0.047
TAA 9 <0.02 0.077 <0.02 0.077 0.034 0.035 0.017 Barley Grain Propiconazole 0.2213- 0.2290 16-49 9 <0.01 1.30 <0.01 1.12 0.0103 0.170 0.363 Propiconazole and Metabolites 9 <0.05 2.22 <0.05 2.12 0.255 0.468 0.656

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.06 0.274 <0.06 0.247 0.069 0.096 0.061
TAA 9 <0.02 0.118 <0.02 0.107 0.022 0.038 0.029 Barley Straw Propiconazole 16-49 9 0.0770 5.20 0.0821 4.99 0.287 1.50 1.91 Propiconazole and Metabolites 9 0.891 10.3 0.918 10.1 2.90 4.21 3.50

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.01 0.024 <0.01 0.023 0.012 0.015 0.005
TAA 9 <0.01 0.042 <0.01 0.038 0.013 0.019 0.011

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used for any results reported as <LOQ in Table C.3. N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.

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TABLE C.4. Summary of Residue Data from Oa t Crop Field Trials with Propiconazole. Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Oat Forage Propiconazole 0.2156- 0.2290 7 11 0.135 1.26 0.154 1.17 0.818 0.689 0.379 Propiconazole and Metabolites 11 0.431 2.46 0.499 2.31 1.48 1.40 0.584

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 0.0178 0.146 0.0184 0.128 0.0282 0.0423 0.0308
TAA 11 <0.01 0.0344 <0.01 0.0328 0.0100 0.0126 0.007 Propiconazole 14 11 0.0316 0.480 0.0404 0.449 0.262 0.240 0.150 Propiconazole and Metabolites 11 0.303 1.51 0.389 1.39 0.975 0.919 0.378

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 0.0189 0.212 0.0236 0.212 0.0434 0.0554 0.0536
TAA 11 <0.01 0.0433 <0.01 0.0431 0.0117 0.0165 0.0103 Oat Hay Propiconazole 0.2156- 0.2290 7 11 0.110 4.46 0.184 4.26 1.38 1.66 1.34 Propiconazole and Metabolites 11 0.629 8.54 0.798 8.00 3.23 3.47 2.31

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 <0.1 0.334 <0.1 0.325 0.100 0.133 0.0675
TAA 11 <0.01 0.0645 <0.01 0.0633 0.0145 0.0201 0.0160 Propiconazole 14 11 0.0620 2.69 0.0680 1.98 0.540 0.677 0.571 Propiconazole and Metabolites 11 0.559 5.69 0.592 4.41 1.99 2.30 1.25

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 <0.1 0.387 <0.1 0.373 0.100 0.140 0.0824
TAA 11 <0.01 0.110 <0.01 0.107 0.0239 0.0300 0.0276 Oat Grain Propiconazole 0.2188- 0.2331 25-48 11 <0.01 0.386 <0.01 0.368 0.0392 0.100 0.121 Propiconazole and Metabolites 11 0.0630 1.61 0.0649 1.56 0.195 0.440 0.549

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 0.0480 0.362 0.0498 0.353 0.125 0.169 0.108
TAA 11 <0.02 0.117 <0.02 0.115 0.0332 0.0476 0.0326 Oat Straw Propiconazole 25-48 11 0.0172 2.40 0.0191 1.21 0.0894 0.309 0.383 Propiconazole and Metabolites 11 0.291 6.07 0.302 5.10 2.05 2.22 1.45

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 <0.01 0.0438 <0.01 0.0435 0.0161 0.0181 0.0110
TAA 11 <0.01 0.0261 <0.01 0.0247 0.0137 0.0147 0.0052

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used fo r any results reported as <LOQ in Tables C.3.1. and C.3.2 N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.

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TABLE C.4. Summary of Residue Data from Rye Crop Field Trials with Propiconazole.
Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Rye Forage Propiconazole 0.2222- 0.2263 6-8 4 0.895 1.62 0.895 1.52 1.11 1.16 0.263 Propiconazole and Metabolites 4 2.29 3.99 2.37 3.75 2.85 2.95 0.677

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 <0.02 0.0775 <0.02 0.0673 0.0356 0.0396 0.0199
TAA 4 <0.01 0.0263 <0.01 0.0224 0.0101 0.0132 0.006 Propiconazole 13-15 4 0.383 0.955 0.403 0.938 0.459 0.565 0.251 Propiconazole and Metabolites 4 1.25 3.01 1.33 2.97 2.03 2.09 0.763

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 <0.02 0.0945 <0.0207 0.0875 0.0313 0.0427 0.0303
TAA 4 <0.01 0.0272 <0.01 0.0260 0.0115 0.0147 0.0076 Rye Grain Propiconazole 0.2216- 0.2288 34-50 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A Propiconazole and Metabolites 4 <0.05 0.160 <0.05 0.144 0.0729 0.0849 0.0410

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 <0.06 0.615 <0.06 0.565 0.150 0.231 0.228
TAA 4 0.0319 0.141 0.0371 0.131 0.0764 0.0802 0.0389 Rye Straw Propiconazole 34-50 4 0.0384 0.650 0.0428 0.551 0.160 0.228 0.225 Propiconazole and Metabolites 4 0.657 4.94 0.689 4.60 1.27 1.96 1.81

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 0.0277 0.108 0.0299 0.102 0.0705 0.0682 0.0334
TAA 4 <0.03 0.0595 <0.03 0.0580 0.0329 0.0384 0.0133

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used for any results reported as <LOQ in Table C.3. N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 13 of 32

TABLE C.4. Summary of Residue Data from Wh eat Crop Field Trials with Propiconazole. Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev.
Wheat Forage Propiconazole 0.2190- 0.2306 7 15 0.271 4.90 0.271 4.79 1.28 1.44 1.13 Propiconazole and Metabolites 15 1.18 9.00 1.23 8.47 2.16 2.88 1.90

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.01 0.0975 <0.0110 0.0918 0.0193 0.0261 0.0207
TAA 15 <0.01 0.0336 <0.01 0.0324 0.0100 0.0130 0.0063 Propiconazole 14-20 15 0.0606 2.16 0.0813 2.13 0.538 0.611 0.528 Propiconazole and Metabolites 15 0.717 5.85 0.778 5.46 1.35 1.75 1.14

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.01 0.0740 <0.01 0.0735 0.0190 0.0245 0.0159
TAA 15 <0.01 0.0444 <0.01 0.0442 0.0100 0.0148 0.0093 Wheat Hay Propiconazole 0.2190- 0.2306 7 15 0.444 9.82 0.444 9.57 2.01 2.75 2.30 Propiconazole and Metabolites 15 1.98 22.5 1.98 21.6 5.31 7.22 5.01

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 0.0218 0.250 0.0218 0.236 0.0525 0.0688 0.0541
TAA 15 <0.01 0.138 <0.01 0.135 0.0182 0.0300 0.0315 Propiconazole 14-20 15 0.149 5.48 0.156 5.41 0.784 1.24 1.28 Propiconazole and Metabolites 15 1.57 18.7 1.62 17.4 3.65 4.78 4.13

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 0.0158 0.174 0.0166 0.166 0.0409 0.0527 0.0400
TAA 15 <0.01 0.128 <0.0125 0.116 0.0242 0.0331 0.0274
Wheat Grain Propiconazole 0.2140- 0.2308 24-64 15 <0.01 0.0842 <0.01 0.0779 0.0100 0.0153 0.0176 Propiconazole and Metabolites 15 <0.05 0.169 <0.05 0.145 0.0556 0.0705 0.0286

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.02 0.286 <0.02 0.279 0.133 0.135 0.0744
TAA 15 <0.01 0.0720 <0.01 0.0718 0.0209 0.0283 0.0172
Wheat Straw Propiconazole 24-64 15 0.0432 4.36 0.0462 4.04 0.455 1.16 1.41 Propiconazole and Metabolites 15 0.570 13.3 0.597 12.6 2.74 4.50 4.05

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.01 0.0560 <0.01 0.0515 0.0124 0.0162 0.0109
TAA 15 <0.01 0.0510 <0.01 0.0497 0.0177 0.0200 0.0114

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used fo r any results reported as <LOQ in Tables C.3.1. and C.3.2 N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 14 of 32 Conclusions: The submitted field trial data are adequate.

Samples were analyzed for propiconazole as propiconazole and propico nazole and metabolites determined as 2,4-DCBA using acceptable methods . The study is supported by adequate storage stability data for propiconazole determined as propiconazole and as propiconazole and metabolites convertible to 2,4-DCBA; storage stabili ty data for the triazole metabolites have been submitted and found acceptable (D. Drew, D 363016, 1/12/12). No additional data will be required for the triazole metabolites.

860.1520 Processed Food and Feed 48681704.der2.doc


### The submitted wheat processing study is acceptable. The processing data indicate that propiconazole and propiconazole and metabolites may concentr ate in AGF, bran, and germ (average processing factors of 36-90x, 1.6-2.3x, a nd 1.6-2.0x) but do not c oncentrate in flour, middlings, and shorts (average proce ssing factors of <0.22-<0.31x, <0.41-0.54x, and <0.46- 0.66x, respectively).

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 15 of 32

TABLE C.3.1 Residue Data for Propiconazole from Wheat Processing Study with Propiconazole.
RAC Processed Commodity Total Rate (lb ai/A) PHI Residues (ppm) 1 [Average] Processing Factor 2

Propiconazole Propiconazole and metabolites Propiconazole Propiconazole and metabolites Cheneyville, LA; 2009 (E17-9032) Wheat Grain (RAC) 1.109 30 0.0590, 0.0601, 0.0465 [0.0552] 0.255, 0.218, 0.280 [0.251] -- --

AGF 4.49, 4.43 [4.46] 9.05, 10.2 [9.63] 81x 38x Bran 0.0724, 0.0629 [0.0677] 0.519, 0.475 [0.497] 1.2x 2.0x

Flour <0.01, <0.01 [<0.01] <0.05, <0.05 [<0.05] <0.18x <0.20x

Middlings 0.0210, 0.0221 [0.0216] 0.153, 0.157 [0.155] 0.39x 0.62x

Shorts 0.0286, 0.0254 [0.0270] 0.236, 0.241 [0.239] 0.49x 0.95x

Germ 0.0730, 0.0635 [0.0683] 0.370, 0.395 [0.383] 1.2x 1.5x

Carrington, ND; 2009 (C13-9038) Wheat Grain (RAC) 1.109 55 0.0256, 0.0200, 0.0227 [0.0228] 0.214, 0.227, 0.188 [0.210] -- --

AGF 2.28, 2.28 [2.28] 7.41, 6.53 [6.97] 100x 33x Bran 0.0441, 0.0431 [0.0436] 0.507, 0.607 [0.557] 1.9x 2.7x

Flour <0.01, <0.01 [<0.01] <0.05, <0.05 [<0.05] <0.44x <0.24x

Middlings <0.01, <0.01 [<0.01] 0.109, 0.0883 [0.0987] <0.44x 0.47x

Shorts <0.01, <0.01 [<0.01] 0.0764, 0.0807 [0.0786] <0.44x 0.37x

Germ 0.0453, 0.0419 [0.0436] 0.513, 0.514 [0.514] 1.9x 2.4x

Average Wheat Grain (RAC) 1.109 30- 55 -- -- AGF 90x 36x
Bran 1.6x 2.3x
Flour <0.31x <0.22x Middlings <0.41x 0.54x

Shorts <0.46x 0.66x
Germ 1.6x 2.0x

1 The LOQ was 0.01 and 0.05 ppm for propiconazole and propiconazole and metabolites, respectively, in all matrices. Per trial average residues were calculated by the study reviewer using the LOQ for all residues reported as <LOQ.
2 Processing Factor = [Measured residue for analyte in the pro cessed fraction] / [Measured residue for analyte in the grain RAC ].


### Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation at 1.109 lb ai/A, average residues of propiconazole and propiconazole and metabol ites determined as 2,4-DCBA, respectively, were: 0.0228-0.0552 and 0.210-0.251 pp m in/on wheat grain (RAC); 2.28-4.46 and 6.97-9.63 ppm in AGF; 0.0436-0.0677 and 0.497-0.557 ppm in bran; <0.01-0.0216 and 0.0987- 0.155 ppm in middlings; <0.01-0.0270 a nd 0.0786-0.239 ppm in shorts; 0.0436-0.0683 and 0.383-0.514 ppm in germ; and, were below the LOQ in flour. The processing data indicate that propiconazole and propiconazole and metabolites may concentr ate in AGF, bran, and germ

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 16 of 32 (average processing factors of 36-90x, 1.6-2.3x, a nd 1.6-2.0x) but do not c oncentrate in flour, middlings, and shorts (average proce ssing factors of <0.22-<0.31x, <0.41-0.54x, and <0.46- 0.66x, respectively).

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of wheat grain RAC and the processed commodities; therefore, processing factors were not calculated. Average residues of TA a nd TAA, respectively, were: 0.228-0.647 and 0.0413-0.207 ppm in/on wheat grain (RAC); 0.110- 0.570 and 0.0558-0.247 ppm in AGF; 0.568-1.74 and 0.0708-0.331 ppm in bran; <0.05-0.169 and < 0.05-0.263 ppm in flour; 0.111-0.261 and 0.0350- 0.182 ppm in middlings; 0.200-0.304 and 0.0450-0.228 ppm in shorts; and, 0.520-3.41 and 0.0615-0.478 ppm in germ. The processing data indi cate that TA may concentrate in bran and germ (average processing factors of 2.6x a nd 3.8x) but do not concentrate in AGF, flour, middlings, and shorts (average pr ocessing factors of 0.68x, <0.24x, 0.45x, and 0.67x, respectively). The processing data indicate thatTAA may concentrate in AGF, bran, shorts, and germ (average processing factors of 1.3x, 1.7x, 1.1x, and 1.9x) but do not concentrate in flour and middlings (average processing factors of <0.76x and 0.86x, respectively). The observed concentration factors were less than the theoretical concentration factors.

Conclusions: The wheat processing results acquired in the study are adequate for satisfying these data requirements. The processing data i ndicate that propiconazole and propiconazole and metabolites may concentrate in AGF, bran, and ge rm (average processing factors of 36-90x, 1.6- 2.3x, and 1.6-2.0x) but do not concentr ate in flour, middlings, and shorts (average processing factors of <0.22-<0.31x, <0.41-0.54x , and <0.46-0.66x, respectively).

860.1650 Submittal of Analytic al Reference Standards

An analytical reference standard for propiconazole is available at the EPA National Pesticide Standards Repository (personal communi cation Charles Stafford, 6/27/12).

860.1850/860.1900 Confined and Field Accumu lation in Rotational Crops

The nature of the residue in confined ro tational crops is understood (D329394, Y. Donovan, 6/15/06). Based on acceptable st udies previously reviewed by EFED, the metabolism of propiconazole in rotational crops is similar to that in primary crops. Plant-back restrictions have been established for propiconazole products regi stered for use on rotational crops based on the confined rotational crop studies. Labels specify that any food/feed crops not listed on the label

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 17 of 32 should not be planted within 105 days of treatme nt. Tolerances for in advertent residues of propiconazole in/on alfalfa plan ted in rotation with propiconazo le-treated crops have been established at 0.1 ppm for alfalfa forage and hay.

860.1550 Proposed Tolerances

Permanent tolerances are currently established fo r the combined residues of propiconazole and its 2,4-DCBA containing metabolites at levels ranging from 0.1-40 ppm in/on plant commodities [40 CFR §180.434(a)]. Permanent tolerances are al so established for the combined residues of propiconazole and its 2,4-DCBA containing metabo lites at 0.05 ppm in fat, meat, and meat byproducts (except liver and kidney) of livestock, 2.0 ppm in liver and kidney of livestock, and at 0.05 ppm in milk; however, no tolerances ha ve been established for eggs and poultry commodities. However, HED has determined that the current tolerance expression for plant and livestock commodities is not appropriate and has previously recommended that the tolerance expression be revised to include on ly parent. This will not be done at the time of this action.

The Codex Alimentarius Commission has estab lished several maximum residue limits (MRLs) for propiconazole in/on various raw agricultura l commodities. In addition, both Canada and Mexico have established MRLs for propiconazo le in/on various commodities. The Codex and Mexican MRLs are expressed in terms of propiconazole per se . The Canadian MRLs are expressed in terms of combined residues of propiconazole and its metabolites containing the 2,4- DCBA moiety. Codex has an MRLs for straw an d fodder of barley, rye, and wheat along with MRL for barley grain. The U.S. cannot harmonize at this level due to the use pattern registered in the U.S along with the CODEX tolerance expre ssion. Canada has MRLs for barley, grain and oats, grain. The U.S. cannot harmonize at this leve l due to the use pattern registered in the U.S but will be harmonized on the tolerance expression for Canada only.

Adequate crop field trial data reflecting the proposed use patterns were submitted for purposes of establishing tolerances. The Organizati on for Economic Cooperation and Development tolerance calculation procedures were utilized in determining th e appropriate tolerance level for the requested amended use.

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 18 of 32 References

DP Barcode: D329394 Subject: Propiconazole (122101): Reregistra tion Eligibility Deci sion (RED) Document; Revised Residue Chemistry Considerations. From: Y. Donovan To: M. Goodis and C. Scheltema Dated: 6/15/06 MRID(s): None

RDI: T. Morton (2/27/2013); S. Hummel (2/27/2013) & E. Reaves (2/27/2013) Petition Number: 2F7975 DP Barcode(s): 400030 PC Code: 122101

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 19 of 32 Attachment 1: Organization for Economic Coope ration and Development tolerance calculation procedures

Cereal Grain Tolerances Associated with 2F7975

**Total Propiconzole Barley Grain** 

**U S**  **Maturity**

**Total number of data (n)** 9 **Percentage of censored data** 11%
**Number of non-censored data** 8 **Lowest residue** 0.050 **Highest residue** 2.120 **Median residue** 0.255

**Mean** 0.468 **Standard deviation (SD)** 0.656 **Correction factor for censoring (CF)** 0.926

**Proposed MRL estimate**

**- Highest residue** 2.120
**- Mean + 4 SD** 3.092
**- CF x 3 Mean** 1.299
**Unrounded MRL** 3.092

**Rounded MRL 3** 

**Residues (mg/kg) n** 
< 0.05 1

0.059 1

0.066 1
0.132 1
0.255 1
0.379 1
0.471 1
0.677 1
2.12 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 20 of 32 **Total Propiconazole Barley Hay** 

**U S**  **7 day PHI**

**Total number of data (n)** 8 **Percentage of censored data** 0%
**Number of non-censored data** 8 **Lowest residue** 2.560 **Highest residue** 11.900 **Median residue** 5.235

**Mean** 6.631 **Standard deviation (SD)** 3.897 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 11.900
**- Mean + 4 SD** 22.221
**- CF x 3 Mean** 19.894
**Unrounded MRL** 22.221

**Rounded MRL 3**  **0**

**Resi d**  **ues (mg/kg) n** 
2.56 1
2.75 1

3.97 1
4.27 1
6.2 1
10 1
11.4 1
11.9 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 21 of 32 **Total Propiconazole Barley Straw** 

**U S**  **Maturity**

**Total number of data (n)** 9 **Percentage of censored data** 0%
**Number of non-censored data** 9 **Lowest residue** 0.918 **Highest residue** 10.100 **Median residue** 2.900

**Mean** 4.206 **Standard deviation (SD)** 3.499 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 10.100
**- Mean + 4 SD** 18.203
**- CF x 3 Mean** 12.619
**Unrounded MRL** 18.203

**Rounded MRL 2**  **0**

**Residues (mg/kg) n** 
0.918 1
1.47 1

1.61 1
1.96 1
2.9 1
3.59 1

5.75 1
9.56 1
10.1 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 22 of 32 **Total Propiconazole Oats Grain** 

**U S**  **Maturity**

**Total number of data (n)** 12 **Percentage of censored data** 0%
**Number of non-censored data** 12 **Lowest residue** 0.065 **Highest residue** 1.560 **Median residue** 0.218

**Mean** 0.514 **Standard deviation (SD)** 0.543 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 1.560
**- Mean + 4 SD** 2.685
**- CF x 3 Mean** 1.542
**Unrounded MRL** 2.685

**Rounded MRL 3** 

**Residues (mg/kg) n** 
0.065 1
0.088 1

0.153 1
0.182 1
0.195 1
0.214 1
0.221 1
0.261 1
0.842 1
0.915 1
1.47 1
1.56 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 23 of 32 **Total Propiconazole Oats Forage** 

**U S**  **7 day PHI**

**Total number of data (n)** 10 **Percentage of censored data** 0%
**Number of non-censored data** 10 **Lowest residue** 0.499 **Highest residue** 2.310 **Median residue** 1.455

**Mean** 1.338 **Standard deviation (SD)** 0.582 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 2.310
**- Mean + 4 SD** 3.665
**- CF x 3 Mean** 4.013
**Unrounded MRL** 4.013

**Rounded MRL 4** 

**Residues (mg/kg) n** 
0.499 1

0.5 1

0.779 1

1.4 1
1.43 1
1.48 1
1.51 1
1.68 1
1.79 1
2.31 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 24 of 32 **Total Propiconazole Oats Hay** 

**U S**  **7 day PHI**

**Total number of data (n)** 11 **Percentage of censored data** 0%
**Number of non-censored data** 11 **Lowest residue** 0.798 **Highest residue** 7.740 **Median residue** 3.230

**Mean** 3.442 **Standard deviation (SD)** 2.255 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 7.740
**- Mean + 4 SD** 12.462
**- CF x 3 Mean** 10.326
**Unrounded MRL** 12.462

**Rounded MRL 1**  **5**

**Residues (mg/kg) n** 
0.798 1
0.905 1

1.07 1
2.35 1
2.67 1
3.23 1
3.28 1
4.76 1
4.82 1
6.24 1
7.74 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 25 of 32 **Total Propiconazole Rye Forage** 

**U S**  **7 day PHI**

**Total number of data (n)** 3 **Percentage of censored data** 0%
**Number of non-censored data** 3 **Lowest residue** 2.370 **Highest residue** 3.750 **Median residue** 2.410

**Mean** 2.843 **Standard deviation (SD)** 0.785 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 3.750
**- Mean + 4 SD** 5.985
**- CF x 3 Mean** 8.530
**Unrounded MRL** 8.530

**Rounded MRL 9** 

High uncertainty of MRL estimate. [Small dataset]

**Residues (mg/kg) n** 
2.37 1
2.41 1

3.75 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 26 of 32 **Total Propiconazole Rye Straw** 

**U S**  **Maturity**

**Total number of data (n)** 4 **Percentage of censored data** 0%
**Number of non-censored data** 4 **Lowest residue** 0.689 **Highest residue** 4.600 **Median residue** 1.274

**Mean** 1.959 **Standard deviation (SD)** 1.807 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 4.600
**- Mean + 4 SD** 9.187
**- CF x 3 Mean** 5.877

**Unroun d**  **ed MRL** 9.187

**Rounded MRL 1**  **0**

High uncertainty of MRL estimate. [Small dataset]

**Residues (mg/kg) n** 
0.689 1
0.907 1

1.64 1
4.6 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 27 of 32 **Total Propiconazole Wheat Forage** 

**U S**  **7 day PHI**

**Total number of data (n)** 13 **Percentage of censored data** 0%
**Number of non-censored data** 13 **Lowest residue** 1.270 **Highest residue** 8.470 **Median residue** 2.760

**Mean** 3.098 **Standard deviation (SD)** 1.949 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 8.470
**- Mean + 4 SD** 10.896
**- CF x 3 Mean** 9.293
**Unrounded MRL** 10.896

**Rounded MRL 1**  **5**

**Residues (mg/kg) n** 
1.27 1
1.31 1

1.45 1
1.88 1
2.11 1
2.16 1
2.76 1
3.01 1
3.37 1
3.77 1
3.94 1
4.77 1
8.47 1

**Total Propiconazole**

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 28 of 32 **Wheat Hay**

**U S**  **7 day PHI**

**Total number of data (n)** 13 **Percentage of censored data** 0%
**Number of non-censored data** 13 **Lowest residue** 3.380 **Highest residue** 21.600 **Median residue** 6.690

**Mean** 7.938 **Standard deviation (SD)** 5.000 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 21.600
**- Mean + 4 SD** 27.939
**- CF x 3 Mean** 23.813
**Unrounded MRL** 27.939

**Rounded MRL 3**  **0**

**Residues (mg/kg) n** 
3.38 1
3.97 1

4.09 1
4.27 1
4.38 1
5.31 1
6.69 1
7.94 1
9.26 1

10 1
10.5 1
11.8 1
21.6 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 29 of 32 **Total Propiconazole**
**Wheat Straw**

**U S**  **Maturity**

**Total number of data (n)** 15 **Percentage of censored data** 0%
**Number of non-censored data** 15 **Lowest residue** 0.600 **Highest residue** 12.600 **Median residue** 2.740

**Mean** 4.502 **Standard deviation (SD)** 4.049 **Correction factor for censoring (CF)** 1.000

**Proposed MRL estimate**

**- Highest residue** 12.600
**- Mean + 4 SD** 20.696
**- CF x 3 Mean** 13.506
**Unrounded MRL** 20.696

**Rounded MRL 2**  **0**

**Residues (mg/kg) n** 
0.6 1

1 1

1.41 1
1.47 1
1.57 1
1.6 1
1.95 1
2.74 1
3.56 1
5.08 1
5.31 1
7.58 1
8.66 1
12.4 1
12.6 1

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 30 of 32 Attachment 2: 

## International Residue Limits Propiconazole (122101; 10/03/2012) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 Codex 3 40 CFR 180.434:

Plant/Livestock: combined residues of the fungicide 1-[[2-(2,4-dichlorophenyl)-4-propyl1,3-dioxolan-2-yl] methyl]-1H1,2,4-triazole and its metabolites determined as 2,4- dichlorobenzoic acid and expressed as parent compound 1-[[2-(2,4-diclorophenyl)-4- propyl-1,3-dioxolan-2-yl] methyl]-1 H -1,2,4-triazole, including all metabolites containing the 2,4- dichlorophenyl-1-methyl substituted moiety Plant and animal commodities: propiconazole The residue is fat soluble.

Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex 3 Barley, hay 30 Barley, straw 20 2 barley straw and fodder, dry Barley, grain 3 0.05 0.2 Rye, forage 9 Rye, straw 10 2 rye straw and fodder, dry Oats, forage 4 Oats, hay 15 Oats, grain 3 0.05 Wheat, forage 15 Wheat, hay 30 Wheat, straw 20 2 wheat straw and fodder, dry Grain, aspirated grain fractions 110

Completed: M. Negussie; 10/04/2012

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.

3 * = absent at the limit of quantitation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed postharvest treated co mmodity, such as processing of treated stored wheat. (fat) = to be measured on the fat portion of the sample. MRLs indicated as proposed have not been finalized by the CCPR and the CAC.


### Results of supervised trials on crops-JMPR Report 2007

Residue data on parent compound was avai lable for barley, rye, and wheat.

For dietary intake calculation purposes, the Me eting estimated in each case what the STMR and HR would be taking into account all residues convertible to 2,4-DCBA.

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 31 of 32 The Meeting decided (based on the metabolism studies available) to apply a conservative default factor of 3 to food commodities. This woul d convert parent-only residues to total residues convertible to 2,4-DCBA, except when additional da ta were available to make a more realistic assessment. For cereal straw a conversion factor of 10 is applied based on metabolism studies. The Meeting could recommend ma ximum and median residue levels based on the LOQs of the parent compounds because the maize, corn, pi neapple, sugar cane, a nd pecan residues were measured as total residues based on the determin ation of 2,4-DCBA. This also took into account that the total residues were below or at the LOQ in all samples.

Residue trials based on the dete rmination of the parent compound

Cereals

Barley Field trials were performed in France, Germ any and Switzerland applying propiconazole in accordance with the GAP in France (2 × 0.12 kg ai/ha with 42 days PHI). The parent propiconazole residues in barley grains were: < 0.02 (7), 0.02 (4), 0.025, 0.03, 0.03, 0.03, 0.03, 0.03, 0.04, 0.04, 0.05, 0.1, and 0.11 mg/kg.

Based on the GAP in France, the Meeting esti mated a maximum residue level of 0.2 mg/kg, and an STMR of 0.0675 (3 × 0.0225) mg/kg for barley. The Meet ing withdrew its previous recommendation of 0.05 mg/kg for barley.

Rye Two trials were performed with 2 × 0.125 kg ai/ha application rate. Grain samples taken 48–50 days after the second applica tion did not contain detectable parent residues (< 0.01, < 0.02 mg/kg).

Wheat Field trials were performed in France Germa ny and UK applying propiconazole in accordance with the GAP in France (2 × 0.12 kg ai/ha with 42 days PHI). The parent propiconazole residues in wheat grains were below the L OQ (< 0.01, < 0.02 mg/kg) in all samples (12).

As the GAP for wheat rye and triticale are th e same, and in both commodities the residues were below the LOQ, the Meeting decided to combine residues in wheat and rye. The Meeting estimated a maximum residue level of 0.02 mg/kg and an STMR of 0.06 (3 × 0.02) mg/kg for wheat and rye and triticale. The Meeting withdrew its pr evious recommendation of 0.05 mg/kg for wheat and rye.

Residues in animal feed

Trials providing data on residues of parent compound

Barley straw Following applications according to French GAP (2 × 0.125 kg ai/ha with a PHI of 42 days) the

### Propiconazole 122101 Summar y of Analytical Chemistry and Residue Data DP# 400030

Page 32 of 32 residues in barley straw were: 0.03, < 0.04 (4), 0.05, 0.05, 0.07, 0.07, 0.12, 0.14, 0.15, 0.15, 0.22, 0.3, 0.32, 0.36, 0.41, 0.42, 0.68, 0.83, and 0.97 mg/kg.

Wheat straw Following applications according to French GAP (2 × 0.125 kg ai/ha with PHI of 42 days) the residues in wheat straw in ranked order, median underlined, were: < 0.04, < 0.04, < 0.04, 0.06, 0.1, 0.13, 0.15, 0.19, 0.3, 0.3, 0.32, 0.41, 0.43, 0.49, 0.54, 0.58, 0.65, 0.77, 0.8, 0.81, 0.82, and 0.89 mg/kg. The Meeting considered that the residue distribution in barley and wheat straw is the same and combined the two data sets. Residue found, in ranked order were: 0.03, < 0.04 (7), 0.05, 0.05, 0.06, 0.07, 0.07, 0.1, 0.12, 0.13 0.14, 0.15, 0.15, 0.15, 0.19, 0.22, 0.3 (3), 0.32, 0.032, 0.36, 0.41, 0.41, 0.42, 0.43, 0.49, 0.54, 0.58, 0.65, 0.68, 0.77, 0.8, 0.81, 0.82, 0.83, 0.89 and 0.97 mg/kg.

The Meeting estimated a maximum residue level of 2 mg/kg for barley, rye, triticale and wheat straw. For cereal straw a conversion factor of 10 is applied to c onvert to total residue based on metabolism studies. The Meeting estimated a highest residue of 9.7 (10 × 0.97) and an STMR of 2.6 (10 × 0.26) mg/kg for barley, rye, triticale and wheat straw.

### Primary Eval uat or

Approved by ur s ton G. Morton, Che mist

# i)**~** Susan V. Hummel

, Senior Scientist HEDIRABIV (7509P) Date: 2/27113

Date: 2/ 27 

### I 13

Note: This OER was originally prepared under co ntract by Versar, In c

. (6850 Ver s ar Center, Spri ngfi eld. VA 2215 I: submiued 6/27112). The DER has bee n reviewed by the Health Efl""ects Divi sion ( HED) and revised to rdlect current Office of Pesticide Progr ams (OPP) policie s.



### STUDY REPORTS:

48681701 Hampton, M. (201 1) Azoxystrobin/Propiconazole SE (Al5909C)**~Magnitude** 

### of Residue s in o r on Rye: Final Report. Pr oject Number: T0 08507 -08
, TK0003206. Unpublished
stu dy prepared by Syngenta Crop Protection, Carolina Ag Research and Easton Agri-Consulting. 

### 391 p

.

EXECUTIVE SUMMARY:

Syngenta Crop Protection

, LLC. has submitted field trial data for propiconazole on rye. Four field trials were co nduct ed in the Un ited States during the 2009 growing season in the North American Free Trad e Agreement (NAFTA) Growing Zones 2 (S C; 1 trial), 5 (lA; 1 trial), and 7 (ND and NE; 2 trials). The petitioner indicated that a fifth tr ial

, cond uct ed in Zone 5 (IA)
, was not included in the study because it was con ducted with annual rye grass instead of cereal g rai n rye. The submission al so includes data for azoxy st robin. Refer to 4868170 l.del for data pertaining to azoxyst r obin.

Eac h trial consisted of one untr eate d plot and tw o treated plots; separate plots were estab li shed for the harvest of forage and for the harvest of grain and straw. At each trial location, the treated plots received two foliar broadcast applications of a multiple active ingredient (MAl) suspocmul s ion (SE) formulatio n (Quilt XcelTM) cont aini ng 1.02 lb ai/g al propi conazole and 1.18 lb ai / gal azoxystrobin. Applications were targeted at Feekes growth stage 5, a nd 7 days prior to harv est for the forage plots, and at 14 days pr ior to Feekes 10.54
, and Feekes 10.54 for g rai n and
straw plots. Only dat a pertaining to propiconazole are reviewed in this DER; ther efo re, the prod uct will he referred to herein as the 1 .02 lb ai/gal S E formulation. Each treat e d plot received
two applications of propiconazole a t 0.1104-0.1150 lb ai/ Napplication, for a total s easona l ra te

o f 0.2216-0.2288 lb ai l A. Applications were made at 13- to 16 -day retr ea tment intervals (RTis) using ground equipment in spray volumes of2.01-23.37 gal/A. A nonionic surfactant (NIS) was added to the sp ray mixtures for all applications in three trials, and a crop oil concentrate (COC)

wa s added to the spray mixtures in one trial. Samples of forage were harvested from all trials at preharvest interva ls ( PHis ) of6-8 and 13-15 days; grain and straw were harvested at maturity (PHis of 34-50 days ). Additional for age samples were ha

. rvested at PHi s of 0
, 3, 7, and 2 1 days

DP# 400030/MRID No

. 4868170 l 

### Page 1 of 16Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 2 of 16 

### from one trial (in IA) to assess residue decline; additional grain and straw samples were collected 14 and 7 days prior to, and 7 days after, maturity.

Application rates in the submission were reporte d in terms of total lb ai/A for combined application of azoxystrobin a nd propiconazole (refer to pg. 10 of MRID 48681701). Individual application rates for azoxystrobi n and propiconazole were calcul ated by the study reviewer based on the ratio of the active ingr edients in the product: 1.18/ 2.2 for azoxystrobin or 1.02/2.2 for propiconazole.

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a high performance liquid chromatography met hod with tandem mass spectrometry detection (LC/MS/MS), Morse Laboratories Meth-180. The lim it of quantitation (LOQ; determined as the lowest limit of method validation; LLMV) was 0.01 ppm. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas chromatography with mass select ive detection (GC/MSD), Nova rtis Crop Protection method AG-626. This is a common moiety method in wh ich all residues of c oncern are converted by base hydrolysis and oxidation to 2,4-DCBA, then de termined as the 2,4-DCBA methyl ester, and reported in propiconazole equivalents. The LOQ (determined as the LLMV) was 0.05 ppm. Samples were analyzed for the triazole metabolit es 1,2,4-triazole (T), tria zole alanine (TA), and triazole acetic acid (TAA) using LC/MS/MS, Morse Laboratories Meth-160, Revision #2. The LOQs (determined as the LLMVs) were: 0.01 ppm for T in all matrices, 0.02, 0.06, and 0.01 ppm for TA in rye forage, grain, and straw, respectively, and 0.01 ppm fo r TAA in forage and 0.03 ppm in grain and straw. Th e methods were adequate for da ta collection based on acceptable concurrent recovery data. The fortification levels used in co ncurrent method recovery were adequate to bracket expected resi due levels. Concurrent recoveri es were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samp les were stored frozen (<-10 °C at the preparation facility and <-20 °C at the analytical laboratory) from collection to analysis for propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, for 61-91 days (2.0-3.0 months) an d 97-209 days (3.2-6.9 months) for forage, 28-58 days (0.9-1.9 months) and 102-155 days (3.4-5. 1 months) for grain, and 28-58 days (0.9-1.9 months) and 104-159 days (3.4-5.2 months) for straw. Sample storage durations prior to analysis for the triazole metabolites were 59-81 days (1.9-2.7 months) for forage, 23-123 days (0.8-4.0 months) for grain, and 28-124 days (0.9-4.1 months ) for straw. All samples were analyzed within 0-8 days of extraction. Adequate storage stability data are available to support the storage durations and conditions of samples from the submitted field trials.

Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propiconazole at 0.2222-0.2263 lb ai/A, residues (and per trial averages) of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, in/ on forage were: 0.895- 1.62 (0.895-1.52) and 2.29-3.99 (2.37-3.75) ppm at the 6- to 8-day PHI; and 0.383-0.955 (0.403- 0.938) and 1.25-3.01 (1.33-2.97) ppm at the 13- to 15- day PHI. In/on grain and straw harvestedPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 3 of 16 

### at PHIs of 34-50 days following two applic ations at 0.2216-0.2288 lb ai/A, corresponding residues (and per trial aver ages) were: <0.01 and <0.05-0.160 (<0.05-0.144) ppm in/on grain, and 0.0384-0.650 (0.0428-0.551) and 0.657-4.94 ( 0.689-4.60) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of rye forage, grain, and straw. Residues (and per trial averages) of TA and TAA, respectively, in/on forage were <0.02-0.0775 (<0.02-0.0673) a nd <0.01-0.0263 (<0.01-0.0224) ppm at the 6- to 8-day PHI; and <0.02-0.0945 (<0.0207-0.0875) and <0.01-0.0272 (<0.01-0.0260) ppm at the 13- to 15-day PHI. Residues (a nd per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.06-0.615 (<0.06-0.565) an d 0.0319-0.141 (0.0371-0.131) ppm in/on grain; and 0.0277-0.108 (0.0299-0.102) and <0.03-0.0595 (<0.03- 0.0580) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on rye forage and straw. Residues of propiconazole and meta bolites determined as 2,4-DCBA in/on rye grain generally increased with increasing PH I, while residues of propiconazole per se were below the LOQ at all sampling intervals. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals; th erefore, residue decline could not be assessed. Residues of TA in/on rye forage, grain, and stra w generally increased with increasing PHI. Residues of TAA increased with increasing PHI in/on rye grain, but residues of TAA in rye forage and straw were near or below the LOQ at each sampling interval; therefore, residue decline could not be assessed.

STUDY/WAIVER ACCEPTABILITY/ DEFICIENCIES/CLARIFICATIONS :
Under the conditions and parameters used in the study, the field tria l residue data are classified as scientifically acceptable. The acceptability of this study fo r regulatory purposes is addressed in the forthcoming U.S. EPA Residue Chemistry Summary Document [DP# 400030].

COMPLIANCE :
Signed and dated Good Laboratory Practice (GLP), Quality Assurance, a nd Data Confidentiality statements were provided. No deviations fr om regulatory requirement s were reported which would have an impact on the validity of the study.

A. BACKGROUND INFORMATION

Propiconazole is a triazole-type fungicide that provides broad spectrum disease control through inhibition of sterol biosynthesis in fungi. It is registered to Syngenta Crop Protection for the control of fungal diseases on a variety of crops.

The nomenclature of propiconazole , 1,2,4-triazole (T), triazole al anine (TA), and triazole acetic acid (TAA) are summarized in Table A.1, and th e physicochemical properties of propiconazole are summarized in Table A.2.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 4 of 16

TABLE A.1. Nomenclature of Propiconazole and Triazoles. Compound

Common name Propiconazole Company experimental names CGA-64250 IUPAC name 1-[2-(2,4_dichlorophenyl)-4-propyl- 1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole CAS name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1, 3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole
CAS # 60207-90-1

End-use products/EP Suspo-emulsion (SE) formulation (Quilt XcelTM) containing 1. 18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole Compound

Common name 2,4-DCBA Chemical name 2,4-dichlorobenzoic acid Compound

Common name 1,2,4-Triazole (T)
Chemical name 1 H -1,2,4-triazole CAS registry number 288-88-0 Compound

Common name Triazole alanine or triazolylalanine (TA)
Chemical name α -amino-1 H -1,2,4-triazole-1-propanoic acid CAS registry number 114419-45-3 Compound

Common name Triazole acetic acid or triazolylacetic acid (TAA)
Chemical name 1 H -1,2,4-triazole-1-acetic acid N N N

O O
Cl Cl

N H N

N

N N N

O H NH 2

O

N N N

O H OPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 5 of 16

TABLE A.1. Nomenclature of Propiconazole and Triazoles. CAS registry number 28711-29-7

TABLE A.2. Physicochemical Properties of Technical Grade Propiconazole.
Parameter Value Reference Boiling point 120°C at 1.9 Pa, >250°C at 101.325 kPa MRID No.:43698701 pH 4.9 @ 25°C (1% aqueous dispersion) MRID No.:43698701 Density 1.289 g/cm3 typical @ 20°C MRID No.: 43698701 Water solubility (20°C) 0.10 g/L at 20°C MRID No.: 41720301

Solvent solubility (temperature not specified) Completely miscible in ethanol, acetone, toluene and n-octanol. n-hexane = 47 g/L MRID No.: 42030201 Vapor pressure at 25°C 4.2 x 10 -7 mm Hg @ 25°C MRID No.: 41720301 Dissociation constant (pK a ) 1.09 MRID No.: 43698701 Octanol/water partition coefficient Log(K OW ) (25 °C) 3.72 @ pH 6.6 MRID No.: 43698701 UV/visible absorption spectrum ( 8 max, nm) Not available MRID No.: 40583703



### B. EXPERIMENTAL DESIGN

B.1. Study Site Information

Four field trials were conduc ted in the United States duri ng the 2009 growing season in the NAFTA Growing Zones 2 (SC; 1 trial), 5 (IA; 1 trial), and 7 (ND and NE; 2 trials). The petitioner indicated that a fift h trial, conducted in Zone 5 (I A), was not included in the study because it was conducted with annual ryeg rass instead of cereal grain rye.

Each trial consisted of one untreated plot and tw o treated plots; separate plots were established for the harvest of forage and for the harvest of gr ain and straw. At each trial location, the treated plots received two foliar broa dcast applications of a 1.02 lb ai/gal SE formulation of propiconazole (Quilt XcelTM) . Applications were targeted at Feekes growth stage 5, and 7 days prior to harvest for the forage plots, and at 14 days prior to Feekes 10.54, and Feekes 10.54 for grain and straw plots. Each treated plot r eceived two applications of propiconazole at 0.1104- 0.1150 lb ai/A/application, for a to tal seasonal rate of 0.2216-0.2288 lb ai/A. Applications were made at 13- to 16-day RTIs using ground equipment in spray volumes of 2.01-23.37 gal/A. An NIS was added to the spray mixtures for all applic ations in three trials, and a COC was added to the spray mixtures in one trial. Samples of forage were harvested from all trials at PHIs of 6-8 and 13-15 days; grain and straw were harvested at maturity (PHIs of 34-50 days). Additional forage samples were harvested at PHIs of 0, 3, 7, and 21 days from one trial (in IA) to assess residue decline; additional grain and straw samples were collected 14 and 7 days prior to, and 7 days after, maturity.

Maintenance pesticides and fertilizers were us ed as needed to produce a commercial quality crop. Monthly temperature ranges and total monthly precipitation were provided for each trial, as well as the historical averag es. Irrigation was used to supplement rainfall as needed. The petitioner stated that actual te mperature recordings were within average historical values, andPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 6 of 16 

### actual average rainfall was within historical ra infall averages. In trial C33-9105 (NE), the first application to treated plot 2 (for age) was made at Feekes 5-7 (v s. 5) due to sporadic growth caused by the weather. Although va riations in temperature and precipitation were reported, no abnormal weather events were indicated to have adversely impacted crop yields or crop growth and development at the remaining trial sites.

Trial conditions are presented in Table B.1.1. Th e study use pattern is presented in Table B.1.2, and the crop varieties grown are identified in Table C.3.

TABLE B.1.1 Trial Site Conditions

. Trial Identification: City, State; Year (Trial No.) Soil characteristics Type %OM pH CEC (meq/100 g) Elko, SC; 2009 (E11-9101) Loamy sand 1.1 6.8 3.1 Bagley, IA; 2009 (C30-9102) Loam 2.8 7 18.2 Carrington, ND; 2009 (C13-9104) Loam 3.9 7.0 27.2 Grand Island, NE; 2009 (C33-9105) Loam 3.5 7.1 18.2

TABLE B.1.2. Stud y Use Pattern.
Location (City, State; Year) Trial ID EP 1 Plot Application Information Tank Mix/ Adjuvants
4 Method; Timing Volume (gal/A) Rate 2 (lb ai/A) RTI 3 (days) Total Rate 2 (lb ai/A) Elko, SC; 2009 (E11- 9101) 1.02 lb ai/gal SE 2 [Forage] 1. Foliar broadcast; Feekes Stage 5 22.37 0.1112 - 0.2222 NIS

2. Foliar broadcast; BBCH 33 21.88 0.1110 14
3 [Grain and

Straw] 1. Foliar broadcast; Feekes 10.0 21.92 0.1111 -- 0.2216 NIS 2. Foliar broadcast; Feekes Stage 10.54 21.25 0.1104 14

Bagley, IA; 2009 (C30- 9102) 1.02 lb ai/gal SE 2 [Forage] 1. Foliar broadcast; Feekes 5 8.50 0.1127 -- 0.2263 NIS 2. Foliar broadcast; 14 days prior to Feekes 10.54 8.91 0.1136 13

3 [Grain and

Straw] 1. Foliar broadcast; 14 days prior to Feekes 10.54 9.02 0.1150 -- 0.2288 NIS

2. Foliar broadcast; Feekes 10.54 10.15 0.1138 14 Carrington, ND; 2009 (C13-9104) 1.02 lb ai/gal SE 2 [Forage] 1. Foliar broadcast; BBCH 30 2.03 0.1129 -- 0.2247 COC 2. Foliar broadcast; Feekes 8 2.01 0.1117 14
3 [Grain and

Straw] 1. Foliar broadcast; Feekes 10.3 2.01 0.1117 -- 0.2235 COC 2. Foliar broadcast; BBCH 71 2.01 0.1117 13

Grand Island, NE; 2009 (C33-9105) 1.02 lb ai/gal SE 2 [Forage] 1. Foliar broadcast; BBCH 32 19.83 0.1117 -- 0.2235 NIS 2. Foliar broadcast; BBCH 51 20.13 0.1118 14
3 [Grain and

Straw] 1. Foliar broadcast; BBCH 59 20.17 0.1109 -- 0.2229 NIS 2. Foliar broadcast; BBCH 71 20.38 0.1120 16

1 EP = End-use Product; a multiple active ingredient (MAI) sus po-emulsion (SE) formulation (Quilt XcelTM) containing 1.18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 7 of 16 2 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
3 RTI = Retreatment Interval.
4 NIS = non-ionic surfactant. COC = crop oil concentrate.

TABLE B.1.3. Trial Numbers and Geographical Locations

. NAFTA Growing Regions Rye Submitted Requested 1

Canada U.S.
1 -- -- --
1A -- -- --
2 1 -- 1
3 -- -- --
4 -- -- --
5 1 -- 2
5A -- -- --
5B -- -- --
6 -- -- --
7 2 -- 2
7A -- -- --
8 -- -- --
9 -- -- --
10 -- -- --
11 -- -- --
12 -- -- --
13 -- -- --
14 -- -- --
15 -- -- --
16 -- -- --
17 -- -- --
18 -- -- --
19 -- -- --
20 -- -- --
21 -- -- --
Total 4 5

1 As per OCSPP 860.1500, Table 5 for rye.


### B.2. Sample Handling and Preparation

Single control and duplicate treate d samples of forage were harv ested at PHIs of 6-8 and 13-15 days; samples of grain (~3 lb) and straw (~2 lb) were harvested at maturity (34- to 50-day PHIs). Additional forage samples were harvested at PHIs of 0, 3, 7, and 21 days from one trial to assess residue decline; additional grain and straw samples were collected at 14 and 7 days prior to, and 7 days after, maturity. The samples were placed in frozen storage at the field sites (interval between collection and freezing not reported). Al l samples were shipped frozen within 0-56Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 8 of 16 

### days of collection by freezer truc k or overnight courier to the pr eparation facility, Syngenta Crop Protection (Greensboro, NC), where they were maintained frozen (<-10 °C) prior to and following preparation. In preparation for analysis , any adhering soil and inedible portions of rye were removed from the samples by light brushin g. Samples were homogenized by grinding in a Hobart food cutter in the presence of dry ice. Within 5-26 days of receipt at the preparation facility, samples were shipped frozen via FedEx to the analytical laboratory, Morse Laboratories (Sacramento, CA), where they were maintain ed frozen (~ -20 °C) prior to analysis.

B.3. Analytical Methodology

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using LC/MS/MS, Morse Laboratories Meth-180 and for residues of propiconazole and its metabolites convertible to 2,4-DCBA (deter mined as 2,4-DCBA, expressed as propiconazole equivalents) using GC/MSD, Novartis Crop Protection met hod AG-626. Samples were analyzed for the triazole metabolites T, TA, and TAA using LC/MS/MS, Morse Labor atories Meth-160, Revision #2. Complete descriptions of the methods, includ ing minor modifications, were included in the submission.

For determination of residues of propiconazole per se , samples were extracted with methanol:water (80:20, v:v) and filtered. Water and saturated NaCl solution were added to an aliquot of the filtrate, which was then partitioned three times with hexane. The combined hexane extracts were evaporated to dryness, reconstitu ted in acetonitrile:wate r (30:70, v:v), and then analyzed using LC/MS/MS. The LOQ (determined as the LLMV) was 0.01 ppm; the limit of detection (LOD) was not reported.

For determination of residues of propiconazo le and metabolites conve rtible to 2,4-DCBA, samples were refluxed with methanol:ammonium hydroxide (80:20, v:v). An aliquot of the extract was evaporated to dryness. The residues were dissolved in aqueous NaOH and heated in the presence of potassium permanganate for oxidation of propiconazole and metabolites to 2,4- DCBA. The sample was acidified with HCl and pa rtitioned with hexane:eth yl ether (90:10, v:v). The organic phase was evaporated to dryness an d derivatized with diazomethane to form the methyl ester of 2,4-DCBA. The derivatized extract was evaporated to dryness, reconstituted in hexane, and purified using an al umina solid phase extraction (SPE ) cartridge. The sample was reduced to a known volume using nitrogen evaporat ion and then analyzed using GC/MSD. The LOQ (determined as the LLMV) was 0.05 ppm; the LOD was not reported.

For determination of T, TA, and TAA, samples we re extracted with methanol:water (80:20, v:v). Following the addition of Celite, the extracts were vacuum filtered, rinsed, and brought to volume with methanol:water (80:20, v:v). For dete rmination of TAA, an aliquot of the extract was purified by SPE and then derivatized by HC l/butanol esterification. The TA aliquot underwent two derivatizations: an esterificat ion using HCl/butanol and an acylation using heptafluorobutyric anhydride (HFBA). The T al iquot was directly derivatized with dansyl chloride to produce the dansyl derivative of 1,2,4-t riazole and partitioned into ethyl acetate. All metabolite extracts were then evaporated to dr yness, redissolved in acetonitrile:water (30:70,Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 9 of 16 

### v:v), and analyzed using LC/MS/MS detection. The LOQs (determined as the LLMV) were: 0.01 ppm for T in all matrices, 0.02, 0.06, and 0.01 ppm for TA in rye forage, grain, and straw, respectively, and 0.01 ppm for TAA in forage and 0.03 ppm in grain and straw. The LODs were not reported.

The methods were validated in conjunc tion with the field trial samples.

C. RESULTS AND DISCUSSION

Sample storage conditions and durations are report ed in Table C.2. Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samples were stored frozen (<-10 °C at the preparation facility and <- 20 °C at the analytical la boratory) from collection to analysis for propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, for 61-91 days (2.0-3.0 months) and 97-209 days (3.2-6.9 months) for fo rage, 28-58 days (0.9-1.9 months) and 102-155 days (3.4-5.1 months) for gr ain, and 28-58 days (0.9-1.9 mont hs) and 104-159 days (3.4-5.2 months) for straw. Sample storage durations prio r to analysis for the triazole metabolites were 59-81 days (1.9-2.7 months) for forage, 23-123 days (0.8-4.0 months) for grain, and 28-124 days (0.9-4.1 months) for straw. All samples were analyzed within 0-8 days of extraction. Acceptable storage stability data for propiconazo le are available indicat ing that residues of propiconazole and metabolites c onvertible to 2,4-DCBA are stable during frozen storage for up to: 38 months in/on grass forage and straw (DP# 210742, 3/15/95, M. Rodriguez); and for up to 36 months in/on wheat grain (DP# 240856, 2/23/05, T. Morton). In addition, acceptable data have been submitted indicating that residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grai n and 30 months in/on soybean seed (refer to 48681707.der). Acceptable storage stability data for the triazole metabolites are available (DP# 363016, 1/12/12, D. Drew; 47606601.der) indicating that re sidues of T, TA, and TAA are stable during frozen storage in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but decline thereafter. Additional st orage stability data for the triazole metabolites (DP# 388246, 5/28/08, M. Doherty) i ndicate that residues of TAA are stable in/on wheat grain, forage, hay, and straw for up to 13 months, and that residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. These data are adequate to support the storage durations and conditions of samples from the submitted field trials. These data are adequate to support the storage durations and conditi ons of samples from the submitted field trials.

Concurrent method recovery data for the GC/M SD and LC/MS/MS methods are presented in Table C.1. Samples were fortified with propi conazole at 0.01-3.5 ppm for determination of propiconazole per se , and at 0.05-10 ppm for determination of propiconazole and metabolites convertible to 2,4-DCBA. Samples were fortif ied with T, TA, and TAA, respectively, at 0.01- 0.1, 0.01-1.0, and 0.01-0.4 ppm. The methods were adequate for data collection based on acceptable concurrent recovery data. Recoveries were generally within the acceptable range of 70-120%. The fortification levels used in concur rent method recovery were adequate to bracket expected residue levels. Appa rent residues of propiconazole per se and metabolite T were belowPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 10 of 16 

### the LOQ in/on all samples of untreated rye. Quan tifiable apparent residues of propiconazole and metabolites determined as 2,4-DCBA were observe d in/on one sample of untreated forage (0.176 ppm). Quantifiable apparent re sidues of TA were observed in /on four samples of untreated forage (0.0286-0.0456 ppm) and one sample of untreated grain (0.0675 ppm), and quantifiable apparent residues of TAA were observed in/on three samples of untr eated forage (0.0126-0.0234 ppm) and one sample of untreated grain (0.0500 pp m). The petitioner attributed the occurrence of residues of TA and TAA in/on untreated sample s to the widespread use of triazoles and the non-specific nature of the common moiety method of analysis. Concurrent recoveries were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Residue data from the rye field trials are re ported in Tables C.3.1 (p ropiconazole) and C.3.2 (triazole metabolites), and the residue data for rye are summarized in Table C.4. Following two foliar broadcast applications of the 1.02 lb ai/gal SE formul ation of propiconazole at 0.2222- 0.2263 lb ai/A, residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, in/on forage were: 0.895-1.62 (0.895- 1.52) and 2.29-3.99 (2.37- 3.75) ppm at the 6- to 8-day PHI; an d 0.383-0.955 (0.403-0.938) and 1.25-3.01 (1.33-2.97) ppm at the 13- to 15-day PHI. In/on grain and stra w harvested at PHIs of 34-50 days following two applications at 0.2216-0.2288 lb ai /A, corresponding residues (and per trial averages) were: <0.01 and <0.05-0.160 (<0.05-0.144) ppm in/on grain, and 0.0384-0.650 (0.0428-0.551) and 0.657-4.94 (0.689-4.60) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of rye forage, grain, and straw. Residues (and per trial averages) of TA and TAA, respectively, in/on forage were <0.02-0.0775 (<0.02-0.0673) a nd <0.01-0.0263 (<0.01-0.0224) ppm at the 6- to 8-day PHI; and <0.02-0.0945 (<0.0207-0.0875) and <0.01-0.0272 (<0.01-0.0260) ppm at the 13- to 15-day PHI. Residues (a nd per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.06-0.615 (<0.06-0.565) an d 0.0319-0.141 (0.0371-0.131) ppm in/on grain; and 0.0277-0.108 (0.0299-0.102) and <0.03-0.0595 (<0.03- 0.0580) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on rye forage and straw. Residues of propiconazole and meta bolites determined as 2,4-DCBA in/on rye grain generally increased with increasing PH I, while residues of propiconazole per se were below the LOQ at all sampling intervals. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals; th erefore, residue decline could not be assessed. Residues of TA in/on rye forage, grain, and stra w generally increased with increasing PHI. Residues of TAA increased with increasing PHI in/on rye grain, but residues of TAA in rye forage and straw were near or below the LOQ at each sampling interval; therefore, residue decline could not be assessed.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 11 of 16

TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole and the Triazole Metabolites from Rye. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

LC/MS/MS Meth-180 Rye Forage Propiconazole 0.01 3 72, 89, 94 85 ± 12 0.1 3 75, 87, 91 84 ± 8.3
3.5 1 93 93 Rye Grain 0.01 3 106, 104, 97 102 ± 4.7 0.1 3 92, 95, 98 95 ± 3.0 Rye Straw 0.01 3 89, 99, 89 92 ± 5.8 0.1 2 96, 87 92
1.0 1 73 73
GC/MSD method AG-626 Rye Forage Propiconazole and metabolites determined as 2,4- DCBA 0.05 4 78, 91, 108, 95 93 ± 12 0.5 2 86, 87 86
5.0 1 74 74
10 1 80 80 Rye Grain 0.05 2 72, 73 72 0.5 3 80, 96, 65 80 ± 16 Rye Straw 0.05 2 71, 85 78 0.5 2 70, 86 78
5.0 1 90 90
LC/MS/MS Meth-160 Rye Forage T 0.01 3 89, 86, 100 92 ± 7.4 0.1 3 82, 82, 106 90 ± 14 TA 0.02 3 91, 81, 104 92 ± 12 0.2 3 86, 92, 100 93 ± 7.0 TAA 0.01 3 106, 105, 108 106 ± 1.5 0.1 3 104, 112, 108 108 ± 4.0 Rye Grain T 0.01 3 86, 91, 94 90 ± 4.0 0.1 3 80, 83, 103 89 ± 13 TA 0.06 3 99, 73, 73 82 ± 15
0.1 1 91 91 0.6 3 96, 76, 77 83 ± 11
1.0 1 84 84
TAA 0.03 1 102 102 0.04 2 106, 84 95
0.3 1 98 98 0.4 2 95, 86 90 Rye Straw T 0.01 3 81, 79, 81 80 ± 1.2 0.1 3 78, 74, 85 79 ± 5.6
TA 0.01 1 119 119 0.05 3 94, 114, 98 102 ± 11 0.5 3 96, 99, 93 96 ± 3.0 TAA 0.03 3 105, 104, 97 102 ± 4.4 0.3 3 97, 101, 97 98 ± 2.3Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 12 of 16 1 Concurrent recoveries we re corrected for apparent residues in control samples.
2 Standard deviations are calculate d only for fortification levels having ≥ 3 samples.
3 Means and standard deviations were calculated by the petitioner.

TABLE C.2. Summary of Storage Conditions

. Matrix Analyte Storage Temperature (°C) Actual Storage Duration 1 Limit of Demonstrated Storage Stability Propiconazole Forage Propiconazole Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 61-91 days (2.0-3.0 months) Re sidues of propiconazole and metabolites convertible to 2,4- DCBA are stable during frozen storage for up to: 38 months in/on grass forage and straw 2 ; and for up to 36 months in/on wheat grain 3

. Residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/on soybean seed 4

. Propiconazole and Metabolites 97-209 days (3.2-6.9 months)

Grain Propiconazole 28-58 days (0.9-1.9 months) Propiconazole and Metabolites 102-155 days (3.4-5.1 months)

Straw Propiconazole 28-58 days (0.9-1.9 months) Propiconazole and Metabolites 104-159 days (3.4-5.2 months)

Triazole metabolites Forage T Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 59-80 days (1.9-2.6 months) Residues of T, TA, and TAA are stable during frozen storage in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but decline thereafter. 5 Residues of TAA are stable in/on wheat grain, forage, hay, and straw for up to 13 months, and residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. 6 TA 59-80 days (1.9-2.6 months) TAA 59-81 days (1.9-2.7 months) Grain T 26-123 days (0.9-4.0 months) TA 23-122 days (0.8-4.0 months) TAA 27-123 days (0.9-4.0 months) Straw T 28-123 days (0.9-4.0 months) TA 30-124 days (1.0-4.1 months) TAA 28-123 days (0.9-4.0 months)

1 Interval from harvest to analysis. Extract s were stored 0-8 days prior to analysis.
2 DP# 210742, 3/15/95, M. Rodriguez.
3 DP# 240856, 2/23/05, T. Morton.
4 Refer to 48681707.der.
5 DP# 363016, 1/12/12, D. Drew; 47606601.der.
6 DP# 388246, 5/28/08, M. Doherty.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 13 of 16 TABLE C.3.1 Residue Data for Propiconazole fr om Rye Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Winter Rye Variety Commodity Total Rate 1 (lb

ai/A) PHI 2 (days) Residues (ppm) 3 [Average] Propiconazole Propiconazole and Metabolites Elko, SC; 2009 (E11-9101) 2 Wrens Abruzzi Fo rage 0.2222 7 1.13, 1.14 [1.14] 2.52, 2.29 [2.41] 14 0.510, 0.450 [0.480] 1.62, 1.56 [1.59] Grain 0.2216 44 <0.01, <0.01 [<0.01] 0.160, 0.128 [0.144] Straw 44 0.180, 0.229 [0.205] 1.79, 1.48 [1.64] Bagley, IA; 2009 (C30- 9102) 5 Not reported Forage 0.2263 0 2.88 3.31
3 2.48 3.71
7 0.895 3.28
14 0.383, 0.493 [0.438] 2.26, 2.67 [2.47]
21 0.342 1.99
Grain 0.2288 28 <0.01 <0.05
35 <0.01 <0.05
42 <0.01, <0.01 [<0.01] 0.0665, 0.0698 [0.0682]
49 <0.01 0.0751
Straw 28 0.233 1.92
35 0.0822 0.837
42 0.0384, 0.0472 [0.0428] 0.657, 0.720 [0.689]
49 0.0403 0.650 Carrington, ND; 2009 (C13-9104) 5 Rymin Forage 0.2247 6 1.00, 1. 13 [1.07] 2.39, 2.34 [2.37] 15 0.394, 0.411 [0.403] 1.25, 1.40 [1.33] Grain 0.2235 50 <0.01, <0.01 [<0.01] <0.05, <0.05 [<0.05] Straw 50 0.113, 0.115 [0.114] 0.938, 0.876 [0.907] Grand Island, NE; 2009 (C33-9105) 7 Not reported Forage 0.2235 8 1.42, 1.62 [1.52] 3.50, 3.99 [3.75] 13 0.920, 0.955 [0.938] 2.92, 3.01 [2.97] Grain 0.2229 34 <0.01, <0.01 [<0.01] 0.0597, 0.0952 [0.0775] Straw 34 0.452, 0.650 [0.551] 4.26, 4.94 [4.60]

1 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
2 For the decline trial, the target PHIs are bolded

. 3 Residues were determ ined as propiconazole per se (LOQ = 0.01 ppm) and as propiconazole and metabolites convertible to 2,4- DCBA (determined as 2,4-DCBA; LOQ = 0.05 ppm). LODs were not reported. Per trial averages were calculated by the study reviewer using the LOQ for values reported as <LOQ.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 14 of 16 TABLE C.3.2 Residue Data for Triazole Metabolites from Rye Field Trials with Propiconazole. Trial ID (City, State; Year) Zone Winter Rye Variety Commodity Total Rate 1 (lb

ai/A) PHI 2 (days) Residues (ppm) 3 [Average] T TA TAA Elko, SC; 2009 (E11-9101) 2 Wrens Abruzzi Forage 0.2222 7 ND, ND [<0.01] <0.02, <0.02 [<0.02] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0214, <0.02 [<0.0207] <0.01, <0.01 [<0.01] Grain 0.2216 44 <0.01, <0.01 [<0.01] <0.06, <0.06 [<0.06] 0.0795, 0.0850 [0.0823] Straw 44 <0.01, <0.01 [<0.01] 0.0970, 0.106 [0.102] 0.0565, 0.0595 [0.0580] Bagley, IA; 2009 (C30-9102) 5 Not reported Forage 0.2263 0 ND 0.0249 <0.01 3 ND 0.0368 <0.01 7 ND 0.0373 0.0102 14 ND, ND [<0.01] 0.0266, 0.0353 [0.0310] <0.01, <0.01 [<0.01] 21 ND 0.0615 0.0102 Grain 0.2288 28 ND 0.207 0.0625 35 <0.01 0.220 0.0835 42 <0.01, <0.01 [<0.01] 0.184, 0.176 [0.180] 0.0695, 0.0715 [0.0705] 49 <0.01 0.303 0.110 Straw 28 <0.01 0.0243 <0.03 35 <0.01 0.0283 <0.03 42 <0.01, <0.01 [<0.01] 0.0277, 0.0320 [0.0299] <0.03, <0.03 [<0.03] 49 <0.01 0.0294 0.0306 Carrington, ND; 2009 (C13-9104) 5 Rymin Forage 0.2247 6 ND, ND [<0.01] 0.0294, 0.0383 [0.0339] <0.01, <0.01 [<0.01] 15 ND, ND [<0.01] 0.0312, 0.0320 [0.0316] 0.0139, 0.0118 [0.0129] Grain 0.2235 50 <0.01, <0.01 [<0.01] 0.138, 0.100 [0.119] 0.0422, 0.0319 [0.0371] Straw 50 <0.01, <0.01 [<0.01] 0.0620, 0.0408 [0.0514] <0.03, <0.03 [<0.03] Grand Island, NE; 2009 (C33-9105) 7 Not reported Forage 0.2235 8 ND, ND [<0.01] 0.0775, 0.0570 [0.0673] 0.0263, 0.0184 [0.0224] 13 ND, ND [<0.01] 0.0805, 0.0945 [0.0875] 0.0248, 0.0272 [0.0260] Grain 0.2229 34 <0.01, <0.01 [<0.01] 0.515, 0.615 [0.565] 0.120, 0.141 [0.131] Straw 34 <0.01, <0.01 [<0.01] 0.0710, 0.108 [0.0895] 0.0318, 0.0396 [0.0357]
1 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
2 For the decline trial the target PHIs are bolded

. 3 The LOQs were: 0.01 ppm for T in all ma trices, 0.02, 0.06, and 0.01 ppm for TA in rye forage, grain, and straw, respectively, and 0.01 ppm for TAA in forage and 0.03 ppm in grain and straw. The LODs were not reported. ND = not detected, as reported by the petitioner. Per trial averages were calculated by the study reviewer using the LOQ for values reported as <LOQ.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 15 of 16

TABLE C.4. Summary of Residue Data from Rye Crop Field Trials with Propiconazole.
Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Rye Forage Propiconazole 0.2222- 0.2263 6-8 4 0.895 1.62 0.895 1.52 1.11 1.16 0.263 Propiconazole and Metabolites 4 2.29 3.99 2.37 3.75 2.85 2.95 0.677

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 <0.02 0.0775 <0.02 0.0673 0.0356 0.0396 0.0199
TAA 4 <0.01 0.0263 <0.01 0.0224 0.0101 0.0132 0.006 Propiconazole 13-15 4 0.383 0.955 0.403 0.938 0.459 0.565 0.251 Propiconazole and Metabolites 4 1.25 3.01 1.33 2.97 2.03 2.09 0.763

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 <0.02 0.0945 <0.0207 0.0875 0.0313 0.0427 0.0303
TAA 4 <0.01 0.0272 <0.01 0.0260 0.0115 0.0147 0.0076 Rye Grain Propiconazole 0.2216- 0.2288 34-50 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A Propiconazole and Metabolites 4 <0.05 0.160 <0.05 0.144 0.0729 0.0849 0.0410

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 <0.06 0.615 <0.06 0.565 0.150 0.231 0.228
TAA 4 0.0319 0.141 0.0371 0.131 0.0764 0.0802 0.0389 Rye Straw Propiconazole 34-50 4 0.0384 0.650 0.0428 0.551 0.160 0.228 0.225 Propiconazole and Metabolites 4 0.657 4.94 0.689 4.60 1.27 1.96 1.81

T 4 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 4 0.0277 0.108 0.0299 0.102 0.0705 0.0682 0.0334
TAA 4 <0.03 0.0595 <0.03 0.0580 0.0329 0.0384 0.0133

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used for any results reported as <LOQ in Table C.3. N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.



### D. CONCLUSION

The submitted rye field trial data are adequate. Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propi conazole at 0.2222-0.2263 lb ai/A, residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, in/on forage were: 0.895-1.62 (0.895-1.52) and 2.29-3.99 (2.37-3.75) ppm at the 6- to 8-day PHI; and 0.383-0.955 (0.403-0.938) and 1.25-3.01 (1.33-2.97) ppm at the 13- to 15-day PHI. In/on grain and straw harvested at PHIs of 34-50 days following two applications at 0.2216- 0.2288 lb ai/A, corresponding residues (and per trial averages) were : <0.01 and <0.05-0.160 (<0.05-0.144) ppm in/on grain, and 0.0384- 0.650 (0.0428-0.551) and 0.657-4.94 (0.689-4.60) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of rye forage, grain, and straw. Residues (and per trial averages) of TA and TAA, respectively, in/on forage were <0.02-0.0775 (<0.02-0.0673) a nd <0.01-0.0263 (<0.01-0.0224) ppm at the 6-Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Rye

DP# 400030/MRID No. 48681701 Page 16 of 16 

### to 8-day PHI; and <0.02-0.0945 (<0.0207-0.0875) and <0.01-0.0272 (<0.01-0.0260) ppm at the 13- to 15-day PHIs. Residues (and per trial aver ages) of TA and TAA, respectively, in/on grain and straw were: <0.06-0.615 (<0.06-0.565) an d 0.0319-0.141 (0.0371-0.131) ppm in/on grain; and 0.0277-0.108 (0.0299-0.102) and <0.03-0.0595 (<0.03- 0.0580) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on rye forage and straw. Residues of propiconazole and meta bolites determined as 2,4-DCBA in/on rye grain generally increased with increasing PH I, while residues of propiconazole per se were below the LOQ at all sampling intervals. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals; th erefore, residue decline could not be assessed. Residues of TA in/on rye forage, grain, and stra w generally increased with increasing PHI. Residues of TAA increased with increasing PHI in/on rye grain, but residues of TAA in rye forage and straw were near or below the LOQ at each sampling interval; therefore, residue decline could not be assessed.

Acceptable methods were used for residue qua ntitation, and the study is supported by adequate storage stability data.

E. REFERENCES

DP# 210742, 3/15/95, M. Rodriguez. DP# 240856, 2/23/05, T. Morton. DP# 388246, 5/28/08, M. Doherty. DP# 363016, 1/12/12, D. Drew; 47606601.der.

F. DOCUMENT TRACKING

RDI: T. Morton(2/27/2013); S. Hummel (2/27/2013) Petition Number: 2F7975 DP Barcode(s): 400030 PC Code: 122101

Template Version June 2005.**+I** Propi co na z ole/PC Code 122101 /Synge nta Crop Protection

, LL C 

# === I DA CO 7. 4.117.4.2/0PPTS 860.1500 /0 ECD IIA 6.3.1, 6.3.2, 6.3.3 and IliA 8.3.1, 8.3.2
, 8.3 .3 Crop Fie ld Trial/ Residue Decli

- Barley



### Primary Evalu at or

Approved by Thurston G. M o rt o n , Chemist HED / RABIV**75~~P )**  

### IJ

# ~v.**~** Susan V. Hummel, Senior Scientist HED/RABIV (7509P) Date: 2/27/13

Date: 2/27/13

Note: Th is D E R was originally prepared under co ntract by Versar, Inc. (6850 V ersar Center, Springfield, Y A 22 I 5 I ; s ubmitted 6 / 27 /l l )

. The DER has been reviewed by the Health Effects Division (HED ) and revised to reflect current Offi ce of Pesticide Pro gra m s (OP P ) policie s

.



### STUDY 

## REPORTS:

48681702 Hampton, M. (2011) Azoxystrobin!Propiconazole SE ( A15909C)- Magnitude ofthe R esidues in or on Barley: Final Report. Project Number: TK0003212, T 004408 / 08. Unpublished study prepared by Syngenta Crop Protection

, Dragon Run Ag Services

, Inc. and Agvise Research. 487 p.



### EXECUTIVE SUMMARY:

S yng enta Crop Protection

, LLC

. has submitted field trial data for propiconaz ole on barley. Nine field trials were conducted in the United States during the 2009-2010 growin g seasons in the North American Free Trade Agreement (NAFTA) Grow ing Zones 2 (VA ; 1 trial)

, 5 (ND and MN; 2 trials), 7 (SD, NO and NE; 3 trials), 9 (CO; 1 trial), 10 (CA; 1 trial), and 11 (ID; 1 trial). The submission also includes data for azoxystrobin

. Refer to 48681702.d e 1 for data pertaining
t o azoxystrobin.

Each trial consisted of one untreated plot and two treated plots; separate plot s were established for the harvest of hay and for the harvest of grain and straw. At each trial location, the treated plots received two foliar broad cast application s of a multiple active ingredient ( MAl) suspoemulsion (SE) formulation (Quilt XcelTM) containing 1.02 lb ailgal propiconazole and 1.18 lb ai/gal azoxystrobin. Applications were target ed at Feekes growth s tage 5, and 7 days prior to harvest for the hay plots, and at 14 days pri or to Feekes l 0.54, and Feeke s 10 .5 4 for grain and
straw plots. Only data pertaining to propicona zole will be reviewed in this DER; therefore

, th e product will be referred to herein as the 1.0 2 lb ai/gal SE formulation. Each plot was treated at 0.10 84 -0.1160 lb ail A/a pplication, for a total seas onal rate of 0.2188-0 .23 11 lb ai/ A. Applications were made at 12- to 15-day retreatment intervals (RTis) u si ng ground equipment in spray volume s of 1 .95-30.7 5 gal/A. A nonioni c su rfactant (NIS) wa s adde d to the spray mixture for each of the ap plications in eight trials

, and a c rop oil concentrate (COC) was added to the
spray mixture in o ne trial. Samples of hay were harve sted from all trials at preharvest interval s (PHis) of 7 and 14 days; grain and straw s amples were harve sted at maturity (PHis of 16-49 days). Additional hay samples were harve ste d at PHis of 0, 3, 7, and 21 days from one trial (i n NO) to assess re s idue decline; additional grain and straw sample s were collected at 14 and 7

DP# 400030/MRID No

. 48681702 Page 1 of 19Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 2 of 19 

### days prior to, and 7 days afte r, maturity. Hay samples were dried to approximately 10-20% moisture content; drying in tervals were not reported.

Application rates in the submission were reporte d in terms of total lb ai/A for combined application of azoxystrobin a nd propiconazole (refer to pg. 11 of MRID 48681702). Individual application rates for azoxystrobi n and propiconazole were calcul ated by the study reviewer based on the ratio of the active ingr edients in the product: 1.18/ 2.2 for azoxystrobin or 1.02/2.2 for propiconazole.

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a high performance liquid chromatography met hod with tandem mass spectrometry detection (LC/MS/MS), Morse Laboratories Meth-180. The lim it of quantitation (LOQ; determined as the lowest limit of method validation; LLMV) was 0.01 ppm. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas chromatography with mass select ive detection (GC/MSD), Nova rtis Crop Protection method AG-626. This is a common moiety method in wh ich all residues of c oncern are converted by base hydrolysis and oxidation to 2,4-DCBA, then de termined as the 2,4-DCBA methyl ester, and reported in propiconazole equivalents. The LOQ (determined as the LLMV) was 0.05 ppm. Samples were analyzed for the triazole metabolit es 1,2,4-triazole (T), tria zole alanine (TA), and triazole acetic acid (TAA) using LC/MS/MS, Morse Laboratories Meth-160, Revision #2. The LOQs (determined as the LLMVs) were: 0.01 ppm for T in all matrices, 0.05, 0.06, and 0.01 ppm for TA in barley hay, grain, and straw, re spectively, and 0.02 ppm for TAA in hay and grain and 0.01 ppm in straw. The methods were adeq uate for data collection based on acceptable concurrent recovery data. The fortification le vels used in concurrent method recovery were adequate to bracket expected resi due levels. Concurrent recoveri es were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samp les were stored frozen (<-10 °C at the preparation facility and <-20 °C at the analytical laboratory) from collection to analysis for propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, for 72-367 days (2.4-12.1 months ) and 121-546 days (4.0-18.0 months) for hay, 58- 322 days (1.9-10.6 months) and 92-379 days ( 3.0-12.5 months) for grain, and 56-317 days (1.8- 10.4 months) and 101-490 days (3.3-16.1 months) for st raw. Sample storage durations prior to analysis for the triazole metabolites were 80- 388 days (2.6-12.8 months) for hay, 55-336 days (1.8-11.1 months) for grain, and 54-294 days (1.8-9.7 months) for straw. All samples were analyzed within 0-16 days of extraction. Adequate storage stability data are available to support the storage durations and conditions of samples from the submitted field trials.

Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propiconazole at 0.2188-0.2311 lb ai/A, residues (and per trial averages) of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, in/on hay were: 0.436- 4.46 (0.436-4.19) and 2.08-13.1 (2.08-11.9) ppm at the 7-day PHI; and 0.157-2.10 (0.175-1.72) and 1.73-6.61 (1.78-5.87) ppm at the 14-day PHI. In /on grain and straw harvested at PHIs of 16-Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 3 of 19 

### 49 days following two applications at 0.2213- 0.2290 lb ai/A, correspond ing residues (and per trial averages) were: <0.01-1.30 (<0.01-1.12) and <0.05-2.22 (<0.05-2.12) ppm in/on grain, and 0.0770-5.20 (0.0821-4.99) and 0.891-10.3 ( 0.918-10.1) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of barley hay, grain, and straw. Residues (and pe r trial averages) of TA and TAA, respectively, in/on hay were <0.05-0.210 (<0.056-0.197) and <0.02-0.065 (<0.02-0.061) ppm at the 7-day PHI; and <0.05-0.184 (<0.05-0.180) and <0.02-0.077 (<0.02-0.077) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.06-0.274 (<0.06-0.247) and <0.02-0.118 (<0.02- 0.107) ppm in/on grain; and <0.01-0.024 (<0.01-0.023) and <0.01-0.042 (<0.01- 0.038) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on barley hay. Residues of propiconazole and metabolites de termined as 2,4-DCBA in/on grain increased slightly with increasing PHI; residues of propiconazole per se were below the LOQ at all sampling intervals. Residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA in straw were variable, but increased slightly fr om the 33- to the 54- day PHI. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals; therefore, residue decline c ould not be assessed. Residues of TA in/on hay generally decreased with increasing PHI; residues of TAA in creased slightly through the 14-day PHI, but were below the LOQ (<0.02 ppm) at the 21-day PHI. Residues of TA and TAA increased with increasing PHI in/on grain and straw.

STUDY/WAIVER ACCEPTABILITY/ DEFICIENCIES/CLARIFICATIONS :
Under the conditions and parameters used in the study, the field tria l residue data are classified as scientifically acceptable. The acceptability of this study fo r regulatory purposes is addressed in the forthcoming U.S. EPA Residue Chemistry Summary Document [DP# 400030].

COMPLIANCE :
Signed and dated Good Laboratory Practice (GLP), Quality Assurance, a nd Data Confidentiality statements were provided. No deviations fr om regulatory requirement s were reported which would have an impact on the validity of the study.

A. BACKGROUND INFORMATION

Propiconazole is a triazole-type fungicide that provides broad spectrum disease control through inhibition of sterol biosynthesis in fungi. It is registered to Syngenta Crop Protection for the control of fungal diseases on a variety of crops.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 4 of 19 

### The nomenclature of propiconazole , 1,2,4-triazole (T), triazole al anine (TA), and triazole acetic acid (TAA) are summarized in Table A.1, and th e physicochemical properties of propiconazole are summarized in Table A.2.

TABLE A.1. Nomenclature of Propiconazole and Triazoles. Compound

Common name Propiconazole Company experimental names CGA-64250 IUPAC name 1-[2-(2,4_dichlorophenyl)-4-propyl- 1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole CAS name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1, 3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole
CAS # 60207-90-1

End-use products/EP Suspo-emulsion (SE) formulation (Quilt XcelTM) containing 1. 18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole Compound

Common name 2,4-DCBA Chemical name 2,4-dichlorobenzoic acid Compound

Common name 1,2,4-Triazole (T)
Chemical name 1 H -1,2,4-triazole CAS registry number 288-88-0 Compound

Common name Triazole alanine or triazolylalanine (TA)
Chemical name α -amino-1 H -1,2,4-triazole-1-propanoic acid CAS registry number 114419-45-3 N N N

O O
Cl Cl

N H N

N

N N N

O H NH 2

OPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 5 of 19

TABLE A.1. Nomenclature of Propiconazole and Triazoles. Compound

Common name Triazole acetic acid or triazolylacetic acid (TAA)
Chemical name 1 H -1,2,4-triazole-1-acetic acid CAS registry number 28711-29-7

TABLE A.2. Physicochemical Properties of Technical Grade Propiconazole.
Parameter Value Reference Boiling point 120°C at 1.9 Pa, >250°C at 101.325 kPa MRID No.:43698701 pH 4.9 @ 25°C (1% aqueous dispersion) MRID No.:43698701 Density 1.289 g/cm3 typical @ 20°C MRID No.: 43698701 Water solubility (20°C) 0.10 g/L at 20°C MRID No.: 41720301

Solvent solubility (temperature not specified) Completely miscible in ethanol, acetone, toluene and n-octanol. n-hexane = 47 g/L MRID No.: 42030201 Vapor pressure at 25°C 4.2 x 10 -7 mm Hg @ 25°C MRID No.: 41720301 Dissociation constant (pK a ) 1.09 MRID No.: 43698701 Octanol/water partition coefficient Log(K OW ) (25 °C) 3.72 @ pH 6.6 MRID No.: 43698701 UV/visible absorption spectrum ( 8 max, nm) Not available MRID No.: 40583703



### B. EXPERIMENTAL DESIGN

B.1. Study Site Information

Nine field trials were conducted in the Unite d States during the 2009-2010 growing seasons in the NAFTA Growing Zones 2 (VA; 1 trial), 5 ( ND and MN; 2 trials), 7 (SD, ND and NE; 3 trials), 9 (CO; 1 trial), 10 (CA; 1 trial), and 11 (ID; 1 trial).

Each trial consisted of one untreated plot and tw o treated plots; separate plots were established for the harvest of hay and for the harvest of grai n and straw. At each trial location, the treated plots received two foliar broa dcast applications of a 1.02 lb ai/gal SE formulation of propiconazole (Quilt XcelTM) . Applications were targeted at Feekes growth stage 5, and 7 days prior to harvest for the hay plots, and at 14 days prior to Feekes 10.54, and Feekes 10.54 for grain and straw plots. Each treated plot r eceived two applications of propiconazole at 0.1084- 0.1160 lb ai/A/application, for a to tal seasonal rate of 0.2188-0.2311 lb ai/A. Applications were made at 12- to 15-day RTIs using ground equipment in spray volumes of 1.95-30.75 gal/A. An NIS was added to the spray mixture for each of th e applications in eight trials, and a COC was added to the spray mixture in one trial. Samples of hay were harvested from all trials at PHIs of 7 and 14 days; grain and straw samples were ha rvested at maturity (PHIs of 16-49 days). Additional hay samples were harvested at PHIs of 0, 3, 7, and 21 days from one trial (in ND) to assess residue decline; additiona l grain and straw samples were co llected at 14 and 7 days prior to, and 7 days after, maturity. Hay samples were dried to approximately 10-20% moisture content; drying interval s were not reported. N N N

O H OPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 6 of 19 

### Maintenance pesticides and fertilizers were us ed as needed to produce a commercial quality crop. Monthly temperature ranges and total mont hly precipitation were provided for each trial, as well as the historical averag es. Irrigation was used to supplement rainfall as needed. The petitioner stated that actual te mperature recordings were within average historical values, and actual average rainfall was within historical ra infall averages. In trial C33-9066 (NE), cool, wet conditions slowed crop development. As a result, th e first application to tr eated plot 3 (grain and straw) was made between mid-to-late boot, and th e second application was made at the end of heading, rather than at Feekes 10.54. In tria l W15-9070 (ID), the barley matured faster than expected; therefore, the second application to treated plot 3 (grain and straw) was made at Feekes 11.2, soft dough ripening stage, rather than 10.54. Although variations in temperature and precipitation were reported, no abnormal weather events were indicated to have adversely impacted crop yields or crop growth and de velopment at the remaining trial sites.

Trial conditions are presented in Table B.1.1. Th e study use pattern is presented in Table B.1.2, and the crop varieties grown are identified in Table C.3.

TABLE B.1.1 Trial Site Conditions

. Trial Identification: City, State; Year (Trial No.) Soil characteristics Type %OM pH CEC (meq/100 g) Suffolk, VA; 2010 (E07-9061) Sandy loam 1.5 5.7 3.0 Northwood, ND; 2009 (C13-9062) Loam 4.7 6.9 19.8 Geneva, MN; 2009 (C09-9063) Sand y clay loam 3.7 6.3 23.4 Gann Valley, SD; 2009 (C16-9 064) Clay 3.1 7.1 38.9 Carrington, ND; 2009 (C13-9065) Sandy loam 2.7 6.9 24.0 Grand Island, NE; 2009 (C33-9066) Loam 3.54 7.14 18.21 Ault, CO; 2009 (W12-9067) Sandy loam 1.4 7.1 29.7 Porterville, CA; 2010 (W32-9068) Sandy loam 0.8 8.5 9.1 Rupert, ID; 2010 (W15-9070) Loam 1.4 8.1 32.0Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 7 of 19 TABLE B.1.2. Stud y Use Pattern.
Location (City, State; Year) Trial ID EP 1 Plot Application Information Tank Mix/ Adjuvants 4 Method; Timing Volume (gal/A) Rate (lb ai/A) 2 RTI 3 (days) Total Rate (lb ai/A) 2 Suffolk, VA; 2010 (E07-9061) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; Feekes GS 5 11.82 0.1140 -- 0.2280 NIS 2. Foliar broadcast; Feek es GS 5.2 11.89 0.1140 14
3 [Grain and

Straw] 1. Foliar broadcast; BBCH 55 12.37 0.1123 -- 0.2264 NIS 2. Foliar broadcast; BBCH 71 12.59 0.1141 14

Northwood, ND; 2009 (C13-9062) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; BBCH 22 20.14 0.1122 -- 0.2236 NIS 2. Foliar broadcast; BBCH 52 20.06 0.1114 14
3 [Grain and

Straw] 1. Foliar broadcast; BBCH 39 20.15 0.1119 -- 0.2231 NIS 2. Foliar broadcast; BBCH 71 20.01 0.1111 15

Geneva, MN; 2009 (C09-9063) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; Feekes 5 15.87 0.1124 -- 0.2257 NIS 2. Foliar broadcast; Feekes 7 16.39 0.1133 14
3 [Grain and

Straw] 1. Foliar broadcast; Feekes 9 17.85 0.1123 -- 0.2254 NIS 2. Foliar broadcast; Feekes 10.54 18.77 0.1131 15

Gann Valley, SD; 2009 (C16- 9064) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; BBCH 21-31 20.30 0.1104 -- 0.2229 NIS 2. Foliar broadcast; BBCH 43-49 20.34 0.1125 12
3 [Grain and

Straw] 1. Foliar broadcast; BBCH 43-49 20.30 0.1123 -- 0.2238 NIS 2. Foliar broadcast; BBCH 71-73 20.89 0.1115 15

Carrington, ND; 2009 (C13-9065) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; BBCH 16 1.98 0.1103 -- 0.2188 COC 2. Foliar broadcast; BBCH 59 1.95 0.1086 14
3 [Grain and

Straw] 1. Foliar broadcast; BBCH 37 2.01 0.1119 -- 0.2238 COC 2. Foliar broadcast; BBCH 69 2.01 0.1119 14

Grand Island, NE; 2009 (C33- 9066) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; BBCH 30 20.90 0.1154 -- 0.2239 NIS 2. Foliar broadcast; BBCH 26 20.13 0.1084 14
3 [Grain and

Straw] 1. Foliar broadcast; BBCH 43 20.06 0.1108 -- 0.2213 NIS 2. Foliar broadcast; BBCH 59 20.00 0.1105 14

Ault, CO; 2009 (W12- 9067) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; Feekes 5 16.17 0.1100 -- 0.2229 NIS 2. Foliar broadcast; Feekes 10 16.60 0.1129 14
3 [Grain and

Straw] 1. Foliar broadcast; Feekes 10.3 18.26 0.1160 -- 0.2290 NIS 2. Foliar broadcast; Feekes 10.54 17.80 0.1130 14

Porterville, CA; 2010 (W32- 9068) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; Feekes 5 28.78 0.1107 -- 0.2266 NIS 2. Foliar broadcast; Feekes 7 30.44 0.1159 14
3 [Grain and

Straw] 1. Foliar broadcast; Feekes 10.53 30.75 0.1129 -- 0.2253 NIS 2. Foliar broadcast; Feekes 10.54 30.38 0.1124 14

Rupert, ID; 2010 (W15- 9070) 1.02 lb ai/gal SE 2 [Hay] 1. Foliar broadcast; BBCH 30 16.23 0.1159 -- 0.2311 NIS 2. Foliar broadcast; BBCH 55 16.78 0.1153 14
3 [Grain and

Straw] 1. Foliar broadcast; BBCH 55-59 18.18 0.1106 -- 0.2221 NIS 2. Foliar broadcast; BBCH 85 12.71 0.1115 14Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 8 of 19 1 EP = End-use Product; a multiple active ingredient (MAI) sus po-emulsion (SE) formulation (Quilt XcelTM) containing 1.18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole.
2 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
3 RTI = Retreatment Interval.
4 NIS = non-ionic surfactant. COC = crop oil concentrate.

TABLE B.1.3. Trial Numbers and Geographical Locations

. NAFTA Growing Regions Barley Submitted Requested 1

Canada U.S.
1 -- -- 1 2 /1 2

2 1 --
3 -- -- --
4 -- -- --
5 2 -- 3/2
5A -- -- --
5B -- -- --
6 -- -- --
7 3 -- 4/3
7A -- -- --
8 -- -- --
9 1 -- 1/1
10 1 -- 1/1
11 1 -- 2/1
12 -- -- --
13 -- -- --
14 -- -- --
15 -- -- --
16 -- -- --
17 -- -- --
18 -- -- --
19 -- -- --
20 -- -- --
21 -- -- --
Total 9 12/9

1 As per OCSPP 860.1500, Table 5 for barley. The second number reflects a 25% reduction in the number of trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application results in no quantifiable residues.
2 Either region is acceptable.


### B.2. Sample Handling and Preparation

Single control and duplicate treate d samples of hay (~2 lb) were harvested at PHIs of 7 and 14 das; grain (~3 lb) and straw (~2 lb) were harvested at maturity (16- to 49-day PHIs). Additional hay samples were harvested at PHIs of 0, 3, 7, and 21 days from one trial to assess residue decline; additional grain and straw samples were collected at 14 and 7 days prior to, and 7 daysPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 9 of 19 

### after, maturity. Hay samples were dried to approximately 10-20% moisture content; drying intervals were not reported. The samples were placed in frozen storage at the field sites (interval between collection and freezing not reported). Al l samples were shipped frozen within 1-36 days of collection by freezer truc k or overnight courier to the pr eparation facility, Syngenta Crop Protection (Greensboro, NC), where they were maintained frozen (<-10 °C) prior to and following preparation. In preparation for analys is, any adhering soil and inedible portions of barley were removed by light br ushing. Samples were homogen ized by grinding in a Hobart food cutter in the presence of dry ice. Within 12-306 days of receipt at the prep aration facility, samples were shipped frozen via FedEx to th e analytical laboratory, Morse Laboratories (Sacramento, CA), where they were maintain ed frozen (~ -20 °C) prior to analysis.

B.3. Analytical Methodology

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using LC/MS/MS, Morse Laboratories Meth-180 and for residues of propiconazole and its metabolites convertible to 2,4-DCBA (deter mined as 2,4-DCBA, expressed as propiconazole equivalents) using GC/MSD, Novartis Crop Protection met hod AG-626. Samples were analyzed for the triazole metabolites T, TA, and TAA using LC/MS/MS, Morse Labor atories Meth-160, Revision #2. Complete descriptions of the methods, includ ing minor modifications, were included in the submission.

For determination of residues of propiconazole per se , samples were extracted with methanol:water (80:20, v:v) and filtered. Water and saturated NaCl solution were added to an aliquot of the filtrate, which was then partitioned three times with hexane. The combined hexane extracts were evaporated to dryness, reconstitu ted in acetonitrile:wate r (30:70, v:v), and then analyzed using LC/MS/MS. The LOQ (determined as the LLMV) was 0.01 ppm; the limit of detection (LOD) was not reported.

For determination of residues of propiconazo le and metabolites conve rtible to 2,4-DCBA, samples were refluxed with methanol:ammonium hydroxide (80:20, v:v). An aliquot of the extract was evaporated to dryness. The residues were dissolved in aqueous NaOH and heated in the presence of potassium permanganate for oxidation of propiconazole and metabolites to 2,4- DCBA. The sample was acidified with HCl and pa rtitioned with hexane:eth yl ether (90:10, v:v). The organic phase was evaporated to dryness an d derivatized with diazomethane to form the methyl ester of 2,4-DCBA. The derivatized extract was evaporated to dryness, reconstituted in hexane, and purified using an al umina solid phase extraction (SPE ) cartridge. The sample was reduced to a known volume using nitrogen evaporat ion and then analyzed using GC/MSD. The LOQ (determined as the LLMV) was 0.05 ppm; the LOD was not reported.

For determination of T, TA, and TAA, samples we re extracted with methanol:water (80:20, v:v). Following the addition of Celite, the extracts were vacuum filtered, rinsed, and brought to volume with methanol:water (80:20, v:v). For dete rmination of TAA, an aliquot of the extract was purified by SPE and then derivatized by HC l/butanol esterification. The TA aliquot underwent two derivatizations: an esterificat ion using HCl/butanol and an acylation usingPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 10 of 19 

### heptafluorobutyric anhydride (HFBA). The T al iquot was directly derivatized with dansyl chloride to produce the dansyl derivative of 1,2,4-t riazole and partitioned into ethyl acetate. All metabolite extracts were then evaporated to dr yness, redissolved in acetonitrile:water (30:70, v:v), and analyzed using LC/MS/MS detection. The LOQs (determined as the LLMV) were: 0.01 ppm for T in all matrices, 0.05, 0.06, and 0.01 ppm for TA in barley hay, grain, and straw, respectively, and 0.02 ppm for TAA in hay and gr ain and 0.01 ppm in straw. The LODs were not reported.

The methods were validated in conjunc tion with the field trial samples.

C. RESULTS AND DISCUSSION

Sample storage conditions and durations are report ed in Table C.2. Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samples were stored frozen (<-10 °C at the preparation facility and <- 20 °C at the analytical labor atory) from collection to analysis for propiconazole and propiconazole and metabolies, respectively, fo r 72-367 days (2.4-12.1 months) and 121-546 days (4.0-18.0 months) for hay, 58-322 days (1.9-10.6 m onths) and 92-379 days (3.0-12.5 months) for grain, and 56-317 days (1.8-10.4 months) and 101- 490 days (3.3-16.1 months) for straw. Sample storage durations prior to anal ysis for the triazole metabolit es were 80-388 days (2.6-12.8 months) for hay, 55-336 days (1.8-11.1 months) for grain, and 54-294 days (1.8-9.7 months) for straw. All samples were analyzed within 0-16 days of extraction. Accep table storage stability data for propiconazole are available indicating that residues of propiconazole and metabolites convertible to 2,4-DCBA are stable during fro zen storage for up to: 38 months in/on grass forage and straw (DP# 210742, 3/15/95, M. Rodri guez); and for up to 36 months in/on wheat grain (DP# 240856, 2/23/05, T. Morton). In ad dition, acceptable data have been submitted indicating that residue s of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/o n soybean seed (refer to 48681707.der, currently under review). Acceptable storage stability data for the triazole metabolites are available (DP# 363016, 1/12/12, D. Drew; 47606601.der) indicating that re sidues of T, TA, and TAA are stable during frozen storage in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but decline thereafter. Additional st orage stability data for the triazole metabolites (DP# 388246, 5/28/08, M. Doherty) i ndicate that residues of TAA are stable in/on wheat grain, forage, hay, and straw for up to 13 months, and that residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. These data are adequate to support the storage durations and conditions of samples from the submitted field trials.

Concurrent method recovery data for the GC/M SD and LC/MS/MS methods are presented in Table C.1. Samples were fortified at 0.01-10 ppm with propiconazole, at 0.05-20 ppm with propiconazole and metabolites, at 0.01-0.1 ppm with T, at 0.0 1-0.6 ppm with TA, and at 0.01-0.2 ppm with TAA. The methods were adequate fo r data collection based on acceptable concurrent recovery data. Recoveries were within the accep table range of 70-120%. The fortification levels used in concurrent method recovery were adequate to bracket exp ected residue levels. ApparentPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 11 of 19 

### residues of propiconazole and metabolite T were below the LOQ in/on all samples of untreated barley. Quantifiable apparent residues of pr opiconazole and metabolites were observed in/on three samples of untreated hay (0.0528-0.0915 ppm ) and one sample of straw (0.0694 ppm). Quantifiable apparent residues of TA were obs erved in/on six samples of untreated hay (0.0525- 0.167 ppm), four samples of grain (0.0810-0.247 ppm), and two samples of straw (0.0140-0.0153 ppm). Quantifiable apparent re sidues of TAA were observed in /on eight samples of untreated hay (0.0224-0.0603 ppm), five samples of grain (0.0208-0.0780 ppm), and four samples of straw (0.0126-0.0250 ppm). The petitioner attributed the occu rrence of residues of TA and TAA in/on untreated samples to the widespread use of tria zoles and the non-specifi c nature of the common moiety method of analysis. Concurrent recoveri es were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Residue data from the barley field trials are reported in Tables C.3.1 (propiconazole) and C.3.2 (triazole metabolites), and the residue data for barley are summarized in Table C.4. Following two foliar broadcast applications of the 1.02 lb ai/gal SE form ulation of propiconazole at 0.2188- 0.2311 lb ai/A, residues (and per tria l averages of propiconazole) per se and propiconazole and metabolites determined as 2,4-DCBA, respectiv ely, in/on hay were: 0.436-4.46 (0.436-4.19) and 2.08-13.1 (2.08-11.9) ppm at the 7-day PHI; and 0.157-2.10 (0.175-1.72) and 1.73-6.61 (1.78- 5.87) ppm at the 14-day PHI. In /on grain and straw harvested at PHIs of 16-49 days following two applications at 0.2213-0.2290 lb ai/A, corresponding residues (and per trial aver ages) were: <0.01-1.30 (<0.01-1.12) and <0.05-2.22 (<0.05-2. 12) ppm in/on grain, and 0.0770-5.20 (0.0821- 4.99) and 0.891-10.3 (0.918-10.1) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of barley hay, grain, and straw. Residues (and pe r trial averages) of TA and TAA, respectively, in/on hay were <0.05-0.210 (<0.056-0.197) and <0.02-0.065 (<0.02-0.061) ppm at the 7-day PHI; and <0.05-0.184 (<0.05-0.180) and <0.02-0.077 (<0.02-0.077) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.06-0.274 (<0.06-0.247) and <0.02-0.118 (<0.02- 0.107) ppm in/on grain; and <0.01-0.024 (<0.01-0.023) and <0.01-0.042 (<0.01- 0.038) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on barley hay. Residues of propiconazole and metabolites de termined as 2,4-DCBA in/on grain increased slightly with increasing PHI; residues of propiconazole per se were below the LOQ at all sampling intervals. Residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA in straw were variable, but increased slightly fr om the 33- to the 54- day PHI. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals; therefore, residue decline c ould not be assessed. Residues of TA in/on hay generally decreased with increasing PHI; residues of TAA in creased slightly through the 14-day PHI, but were below the LOQ (<0.02 ppm) at the 21-day PHI. Residues of TA and TAA increased with increasing PHI in/on grain and straw.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 12 of 19

TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Barley. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

LC/MS/MS Meth-180 Barley Hay Propiconazole 0.01 6 88, 92, 79, 100, 96, 80 89 ± 8.5 0.1 3 85, 87, 89 87 ± 2.0 10 3 83, 86, 77 82 ± 4.6 Barley Grain 0.01 3 98, 92, 97 96 ± 3.2 0.1 2 95, 89 92
0.5 1 98 98
1.0 1 85 85
2.0 1 91 91 Barley Straw 0.01 3 97, 95, 104 99 ± 4.7 0.1 2 96, 97 96
10 1 92 92
GC/MSD method AG-626 Barley Hay Propiconazole and metabolites determined as 2,4- DCBA 0.05 8 79, 74, 100, 114, 77, 81, 88, 103 90 ± 15 0.5 7 76, 91, 82, 100, 83, 83, 86 86 ± 7.7
2.5 1 99 99
10 1 91 91
20 1 82 82 Barley Grain 0.05 5 94, 92, 79, 70, 115 90 ± 17 0.5 5 75, 72, 70, 74, 70 72 ± 2.3
5.0 1 102 102 Barley Straw 0.05 3 74, 74, 80 76 ± 3.5 0.5 3 119, 84, 72 92 ± 24
12.5 1 94 94
LC/MS/MS Meth-160 Barley Hay T 0.01 7 99, 80, 99, 72, 101, 75, 79 86 ± 13 0.1 7 88, 83, 99, 75, 106, 70, 86 87 ± 13 TA 0.05 7 87, 94, 93, 87, 102, 88, 103 93 ± 6.8 0.5 7 90, 93, 96, 95, 99, 97, 98 95 ± 3.1 TAA 0.02 7 90, 79, 112, 82, 109, 96, 95 95 ± 12 0.2 7 83, 92, 107, 95, 104, 93, 103 97 ± 8.4 Barley Grain T 0.01 4 89, 94, 86, 92 90 ± 3.5 0.1 4 86, 96, 79, 98 90 ± 8.9 TA 0.06 4 97, 87, 80, 93 89 ± 7.4 0.6 4 89, 92, 83, 86 88 ± 3.9 TAA 0.02 4 90, 100, 88, 87 91 ± 6.0 0.2 4 80, 99, 85, 83 87 ± 8.4 Barley Straw T 0.01 4 87, 101, 75, 106 92 ± 14 0.1 4 87, 90, 74, 107 90 ± 14 TA 0.01 4 81, 90, 101, 105 94 ± 11 0.1 4 81, 90, 91, 97 90 ± 6.6Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

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TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Barley. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

TAA 0.01 4 82, 95, 101, 87 91 ± 8.4 0.1 4 83, 83, 92, 95 88 ± 6.2

1 Concurrent recoveries we re corrected for apparent residues in control samples.
2 Standard deviations are calculate d only for fortification levels having ≥ 3 samples.
3 Means and standard deviations were calculated by the petitioner.

TABLE C.2. Summary of Storage Conditions

. Matrix Analyte Storage Temperature (°C) Actual Storage Duration 1 Limit of Demonstrated Storage Stability Propiconazole Hay Propiconazole Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 72-367 days (2.4-12.1 months) Re sidues of propiconazole and metabolites convertible to 2,4- DCBA are stable during frozen storage for up to: 38 months in/on grass forage and straw 2 ; and for up to 36 months in/on wheat grain 3

. Residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/on soybean seed 4

. Propiconazole and Metabolites 121-546 days (4.0-18.0 months)

Grain Propiconazole 58-322 days (1.9-10.6 months) Propiconazole and Metabolites 92-379 days (3.0-12.5 months)

Straw Propiconazole 56-317 days (1.8-10.4 months) Propiconazole and Metabolites 101-490 days (3.3-16.1 months)

Triazole metabolites Hay T Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 80-377 days (2.6-12.4 months) Residues of T, TA, and TAA are stable during frozen storage in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but decline thereafter. 5 Residues of TAA are stable in/on wheat grain, forage, hay, and straw for up to 13 months, and residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. 6 TA 91-388 days (3.0-12.8 months) TAA 84-378 days (2.8-12.4 months) Grain T 56-329 days (1.8-10.8 months) TA 55-336 days (1.8-11.1 months) TAA 56-330 days (1.8-10.9 months) Straw T 54-294 days (1.8-9.7 months) TA 55-293 days (1.8-9.6 months) TAA 54-294 days (1.8-9.7 months)

1 Interval from harvest to analysis. Extracts were stored 0-16 days prior to analysis.
2 DP# 210742, 3/15/95, M. Rodriguez.
3 DP# 240856, 2/23/05, T. Morton.
4 Refer to 48681707.der, currently under review.
5 DP# 363016, 1/12/12, D. Drew; 47606601.der.
6 DP# 388246, 5/28/08, M. Doherty.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 14 of 19

TABLE C.3.1 Residue Data for Propiconazole from Barley Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Crop; Variety Commodity Total Rate (lb ai/A) 1 PHI (days) 2 Residues (ppm) 3 [Average]
Propiconazole Propiconazole and Metabolites Suffolk, VA; 2010 (E07-9061) 2 Winter Barley; Nomini Hay 0.2280 7 1.90, 1.49 [1.70] 5.02, 3.52 [4.27] 14 0.419, 0.516 [0.468] 1.73, 1.82 [1.78] Grain 0.2264 30 0.144, 0.137 [0.141] 0.589, 0.765 [0.677] Straw 30 2.97, 3.06 [3. 02] 9.80, 10.3 [10.1] Northwood, ND; 2009 (C13-9062) 5 Malting Barley; Pinnacle Hay 0.2236 0 5.98 7.75
3 2.02 3.77
7 0.436 2.08
14 0.375, 0.299 [0.337] 2.54, 2.83 [2.69]
21 0.127 1.66

Grain 0.2231 33 <0.01 <0.05
40 <0.01 0.0555
47 <0.01, <0.01 [<0.01] 0.0530, 0.0659 [0.0595]
54 <0.01 0.0585
Straw 0.2231 33 0.125 1.31
40 0.0796 0.992
47 0.124, 0.116 [0.120] 0.944, 0.891 [0.918]
54 0.145 1.35 Geneva, MN; 2009 (C09-9063) 5 Spring Barley; Rawson Hay 0.2257 7 0.904, 0.724 [0.814] 2.28, 2.83 [2.56] 14 0.157, 0.193 [0.175] 2.21, 2.95 [2.58] Grain 0.2254 44 0.0106, <0.01 [<0.0103] 0.188, 0.570 [0.379] Straw 44 0.194, 0.168 [0.181] 1.99, 1.93 [1.96] Gann Valley, SD; 2009 (C16-9064) 7 Malting Barley; Lacey Hay 0.2229 7 2.12, 1.74 [1.93] 9.81, 10.2 [10.0] 14 0.546, 0.588 [0.567] 5.92, 5.29 [5.61] Grain 0.2238 33 <0.01, <0.01 [<0.01] 0.130, 0.133 [0.132] Straw 33 0.716, 0.722 [0.719] 3.05, 2.74 [2.90] Carrington, ND; 2009 (C13-9065) 7 Malting Barley; Pinnacle Hay 0.2188 7 0.848, 0.616 [0.732] 2.85, 2.64 [2.75] 14 0.476, 0.490 [0.483] 2.84, 2.85 [2.85] Grain 0.2238 48 <0.01, <0.01 [<0.01] 0.0601, 0.0716 [0.0659] Straw 48 0.250, 0.240 [0.245] 1.80, 1.41 [1.61] Grand Island, NE; 2009 (C33-9066) 7 Spring Barley; Baronesse Hay 0.2239 7 4.46, 3.92 [4.19] 11.0, 11.7 [11.4] 14 1.09, 1.05 [1.07] 2.94, 2.59 [2.77] Grain 0.2213 29 <0.01, <0.01 [<0.01] <0.05, <0.05 [<0.05] Straw 29 0.0872, 0.0770 [0.0821] 1.62, 1.31 [1.47] Ault, CO; 2009 (W12-9067) 9 Malting Barley; Moravian 37 Hay 0.2229 7 2.42, 2.11 [2.27] 4.35, 3.59 [3.97] 14 1.05, 1.01 [1.03] 3.40, 3.18 [3.29] Grain 0.2290 25 0.175, 0.215 [0.195] 0.425, 0.516 [0.471] Straw 25 5.20, 4.78 [4.99] 10.2, 8.91 [9.56] Porterville, CA; 2010 (W32-9068) 10 Winter Barley; UC937 Hay 0.2266 7 2.88, 3.19 [3.04] 10.7, 13.1 [11.9] 14 1.34, 2.10 [1.72] 5.13, 6.61 [5.87] Grain 0.2253 49 0.933, 1.30 [1.12] 2.02, 2.22 [2.12] Straw 49 3.89, 3.77 [3.83] 5.79, 5.70 [5.75]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

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TABLE C.3.1 Residue Data for Propiconazole from Barley Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Crop; Variety Commodity Total Rate (lb ai/A) 1 PHI (days) 2 Residues (ppm) 3 [Average]
Propiconazole Propiconazole and Metabolites Rupert, ID; 2010 (W15-9070) 11 Malting Barley; Ida-Gold II Hay 0.2311 7 0.691, 0.879 [0.785] 5.63, 6.77 [6.20] 14 0.183, 0.189 [0.186] 4.32, 4.26 [4.29] Grain 0.2221 16 0.0203, 0.0190 [0.0197] 0.273, 0.237 [0.255] Straw 16 0.289, 0.285 [0.287] 3.76, 3.42 [3.59]

1 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
2 For the decline trial, the target PHIs are bolded

. 3 Residues were determ ined as propiconazole per se (LOQ = 0.01 ppm) and as propiconazole and metabolites convertible to 2,4- DCBA (determined as 2,4-DCBA; LOQ = 0.05 ppm). LODs were not reported. Per trial averages were calculated by the study reviewer using the LOQ for values reported as <LOQ.

TABLE C.3.2 Residue Data for Triazole Metabolites from Barley Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Crop; Variety Commodity Total Rate (lb ai/A) 1 PHI (days) 2 Residues (ppm) 3 [Average]
T TA TAA Suffolk, VA; 2010 (E07-9061) 2 Winter Barley; Nomini Hay 0.2280 7 <0.01, <0.01 [<0.01] 0.117, 0.110 [0.114] 0.0650, 0.0560 [0.0605] 14 ND, ND [<0.01] 0.0920, 0.0655 [0.0788] 0.0358, 0.0338 [0.0348] Grain 0.2264 30 ND, ND [<0.01] 0.0610, 0.0775 [0.0693] 0.0476, 0.0580 [0.0528] Straw 30 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] 0.0379, 0.0303 [0.0341] Northwood, ND; 2009 (C13-9062) 5 Malting Barley; Pinnacle Hay 0.2236 0 <0.01 0.0715 0.0200
3 ND 0.0705 0.0214
7 ND 0.0740 0.0224
14 <0.01, <0.01 [<0.01] 0.0685, 0.0520 [0.0603] 0.0304, 0.0281 [0.0293]
21 <0.01 <0.05 <0.02
Grain 0.2231 33 ND 0.0960 0.0454
40 ND 0.106 0.0500
47 <0.01, <0.01 [<0.01] 0.125, 0.126 [0.126] 0.0505, 0.0510 [0.0508]
54 <0.01 0.136 0.0565
Straw 0.2231 33 <0.01 <0.01 <0.01
40 <0.01 <0.01 <0.01
47 <0.01, <0.01 [<0.01] 0.0140, <0.01 [<0.0120] 0.0136, 0.0114 [0.0125]
54 <0.01 0.0182 0.0228Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 16 of 19

TABLE C.3.2 Residue Data for Triazole Metabolites from Barley Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Crop; Variety Commodity Total Rate (lb ai/A) 1 PHI (days) 2 Residues (ppm) 3 [Average]
T TA TAA Geneva, MN; 2009 (C09-9063) 5 Spring Barley; Rawson Hay 0.2257 7 ND, ND [<0.01] 0.0635, 0.0580 [0.0608] <0.02, <0.02 [<0.02] 14 ND, ND [<0.01] 0.0720, 0.0575 [0.0648] 0.0402, 0.0327 [0.0365] Grain 0.2254 44 <0.01, <0.01 [<0.01] 0.106, 0.102 [0.104] 0.0302, 0.0282 [0.0292] Straw 44 <0.01, <0.01 [<0.01] 0.0152, 0.0176 [0.0164] 0.0111, 0.0134 [0.0123] Gann Valley, SD; 2009 (C16-9064) 7 Malting Barley; Lacey Hay 0.2229 7 <0.01, <0.01 [<0.01] 0.0565, 0.0625 [0.0595] <0.02, 0.0204 [<0.0202] 14 ND, ND [<0.01] <0.05, <0.05 [<0.05] <0.02, <0.02 [<0.02] Grain 0.2238 33 ND, ND [<0.01] 0.0630, 0.0640 [0.0635] <0.02, <0.02 [<0.02] Straw 33 <0.01, <0.01 [<0.01] 0.0107, <0.01 [<0.0104] 0.0113, 0.0112 [0.0113] Carrington, ND; 2009 (C13-9065) 7 Malting Barley; Pinnacle Hay 0.2188 7 <0.01, <0.01 [<0.01] 0.0620, <0.05 [<0.0560] 0.0218, <0.02 [<0.0209] 14 <0.01, <0.01 [<0.01] <0.05, 0.0520 [<0.0510] 0.0202, 0.0257 [0.0230] Grain 0.2238 48 ND, ND [<0.01] <0.06, 0.0855 [<0.0728] <0.02, 0.0242 [<0.0221] Straw 48 <0.01, <0.01 [<0.01] 0.0179, 0.0206 [0.0193] 0.0134, 0.0134 [0.0134] Grand Island, NE; 2009 (C33-9066) 7 Spring Barley; Baronesse Hay 0.2239 7 <0.01, ND [<0.01] 0.210, 0.184 [0.197] 0.0615, 0.0580 [0.0598] 14 ND, ND [<0.01] 0.184, 0.176 [0.180] 0.0770, 0.0760 [0.0765] Grain 0.2213 29 ND, ND [<0.01] 0.274, 0.220 [0.247] 0.118, 0.0955 [0.107] Straw 29 <0.01, <0.01 [<0.01] 0.0224, 0.0233 [0.0229] 0.0345, 0.0421 [0.0383] Ault, CO; 2009 (W12-9067) 9 Malting Barley; Moravian 37 Hay 0.2229 7 ND, ND [<0.01] 0.0685, 0.0715 [0.0700] 0.0298, 0.0319 [0.0309] 14 ND, ND [<0.01] 0.0930, 0.0640 [0.0785] 0.0436, 0.0352 [0.0394] Grain 0.2290 25 ND, ND [<0.01] <0.06, <0.06 [<0.06] <0.02, <0.02 [<0.02] Straw 25 <0.01, <0.01 [<0.01] 0.0239, 0.0184 [0.0212] 0.0282, 0.0230 [0.0256] Porterville, CA; 2010 (W32-9068) 10 Winter Barley; UC937 Hay 0.2266 7 <0.01, <0.01 [<0.01] 0.104, 0.106 [0.105] <0.02, <0.02 [<0.02] 14 <0.01, <0.01 [<0.01] 0.131, 0.162 [0.147] 0.0226, 0.0282 [0.0254] Grain 0.2253 49 ND, <0.01 [<0.01] <0.06, <0.06 [<0.06] <0.02, <0.02 [<0.02] Straw 49 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] 0.0160, 0.0148 [0.0154]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 17 of 19

TABLE C.3.2 Residue Data for Triazole Metabolites from Barley Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Crop; Variety Commodity Total Rate (lb ai/A) 1 PHI (days) 2 Residues (ppm) 3 [Average]
T TA TAA Rupert, ID; 2010 (W15-9070) 11 MaltingBarley; IdaGold II Hay 0.2311 7 ND, ND [<0.01] 0.0625, 0.0675 [0.0650] 0.0448, 0.0478 [0.0463] 14 ND, ND [<0.01] <0.05, <0.05 [<0.05] 0.0298, 0.0382 [0.0340] Grain 0.2221 16 ND, <0.01 [<0.01] <0.06, <0.06 [<0.06] <0.02, <0.02 [<0.02] Straw 16 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01]

1 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
2 For the decline trial, the target PHIs are bolded

. 3 The LOQs (determined as the LLMVs) were: 0.01 ppm for T in all matrices, 0.05, 0.06, and 0.01 ppm for TA in barley hay, grain, and straw, respectively, and 0.02 ppm for TAA in hay and grain and 0.01 ppm in st raw. Per trial averages were calculate d by the study reviewer using the L OQ for values reported as <LOQ.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 18 of 19

TABLE C.4. Summary of Residue Data from Barley Crop Field Trials with Propiconazole. Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Barley Hay Propiconazole 0.2188- 0.2311 7 9 0.436 4.46 0.436 4.19 1.70 1.77 1.25 Propiconazole and Metabolites 9 2.08 13.1 2.08 11.9 4.27 6.13 3.95

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.05 0.210 <0.056 0.197 0.070 0.089 0.045
TAA 9 <0.02 0.065 <0.02 0.061 0.022 0.033 0.017 Propiconazole 14 9 0.157 2.10 0.175 1.72 0.483 0.671 0.509 Propiconazole and Metabolites 9 1.73 6.61 1.78 5.87 2.85 3.53 1.42

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.05 0.184 <0.05 0.180 0.065 0.084 0.047
TAA 9 <0.02 0.077 <0.02 0.077 0.034 0.035 0.017 Barley Grain Propiconazole 0.2213- 0.2290 16-49 9 <0.01 1.30 <0.01 1.12 0.0103 0.170 0.363 Propiconazole and Metabolites 9 <0.05 2.22 <0.05 2.12 0.255 0.468 0.656

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.06 0.274 <0.06 0.247 0.069 0.096 0.061
TAA 9 <0.02 0.118 <0.02 0.107 0.022 0.038 0.029 Barley Straw Propiconazole 16-49 9 0.0770 5.20 0.0821 4.99 0.287 1.50 1.91 Propiconazole and Metabolites 9 0.891 10.3 0.918 10.1 2.90 4.21 3.50

T 9 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 9 <0.01 0.024 <0.01 0.023 0.012 0.015 0.005
TAA 9 <0.01 0.042 <0.01 0.038 0.013 0.019 0.011

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used for any results reported as <LOQ in Table C.3. N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.



### D. CONCLUSION

The submitted barley field trial data are adequate . Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propic onazole at 0.2188-0.2311 lb ai/A, residues (and per trial averages of propiconazole) per se and propiconazole and metabolites determined as 2,4- DCBA, respectively, in/on ha y were: 0.436-4.46 (0.436-4.19) a nd 2.08-13.1 (2.08-11.9) ppm at the 7-day PHI; and 0.157-2.10 (0.175-1.72) and 1.73-6.61 (1.78-5.87) ppm at the 14-day PHI. In/on grain and straw harvested at PHIs of 16-49 days following two applications at 0.2213- 0.2290 lb ai/A, corresponding residues (and per trial averages) were: <0.01-1.30 (<0.01-1.12) and <0.05-2.22 (<0.05-2.12) ppm in/on gr ain, and 0.0770-5.20 (0.0821-4.99) and 0.891-10.3 (0.918-10.1) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of barley hay, grain, and straw. Residues (and pe r trial averages) of TA and TAA, respectively,Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Barley

DP# 400030/MRID No. 48681702 Page 19 of 19 

### in/on hay were <0.05-0.210 (<0.056-0.197) and <0.02-0.065 (<0.02-0.061) ppm at the 7-day PHI; and <0.05-0.184 (<0.05-0.180) and <0.02-0.077 (<0.02-0.077) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.06-0.274 (<0.06-0.247) and <0.02-0.118 (<0.02- 0.107) ppm in/on grain; and <0.01-0.024 (<0.01-0.023) and <0.01-0.042 (<0.01- 0.038) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on barley hay. Residues of propiconazole and metabolites de termined as 2,4-DCBA in/on grain increased slightly with increasing PHI; residues of propiconazole per se were below the LOQ at all sampling intervals. Residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA in straw were variable, but increased slightly fr om the 33- to the 54- day PHI. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals; therefore, residue decline c ould not be assessed. Residues of TA in/on hay generally decreased with increasing PHI; residues of TAA in creased slightly through the 14-day PHI, but were below the LOQ (<0.02 ppm) at the 21-day PHI. Residues of TA and TAA increased with increasing PHI in/on grain and straw.

Acceptable methods were used for residue qua ntitation, and the study is supported by adequate storage stability data.

E. REFERENCES

DP# 210742, 3/15/95, M. Rodriguez. DP# 240856, 2/23/05, T. Morton. DP# 388246, 5/28/08, M. Doherty. DP# 363016, 1/12/12, D. Drew; 47606601.der.

F. DOCUMENT TRACKING

RDI: T. Morton(2/27/2013); S. Hummel (2/27/2013) Petition Number: 2F7975 DP Barcode(s): 400030 PC Code: 122101

Template Version June 2005.**~** Propiconazole / PC C o de I 2 210 1/S yngenta C rop Protection

, LL C
.,**~** 

### ==: 

# t DACO 7.4.1/7.4.2 / 0 P PTS 860.1 5 00 / 0 EC D IIA 6.3

. I
, 6

. 3.2
, 6 .3.3 an d 111A 8

. 3.1
, 8

. 3 .2, 8

. .1 • .1 C rop Field Trial/ Re s idue Decline**~** Oats



### Primary Evaluator Dat e : 2 / 27 / 13

Approved by Date : 2 / 27 / 13

No te : Thi s DER w as o r i gina lly pr e p a r e d und er co ntract by Versar
, In c. ( 6850 V er sar Cent e r , S pringfield

, VA 22 I 51 ; submitt e d 6 / 27 / 12}. Th e DER h as b ee n review ed b y th e H e a lt h Eff ects D i vi si o n (HE D ) and r ev ised to r eflect curr e n t Offic e of Pesticid e l>r o grams (OPP) polic i e s.



### STUDY REPORTS:

4868170 3 Hampton, M. (20 I 

### l) Azoxystrobin/Propiconazole SE (A 15909C)

- Magnitude of th e Residue s in or on Oats: Final Report

. Proj e ct Number: TK0003209
, T005494/08. Unpublished study pr e pared by Syngenta Crop Protection

. 683 p.

EXECUTIVE SUMMARY:

Syngenta Crop Protection, LLC. has submitted field trial data for azoxystrobin on oat s

. Tw e lve field trial s wer e conduc t ed in the U nited States during the 2009-2010 growing seasons in the North American Free Trade Agr e ement (NAFT A) Growing Zone s 1 ( PA ; 1 trial)

, 2 ( SC ; 1 tr i al ), 5 (ND
, MN, and IA; 6 trials), 6 (TX; l trial)

, 7 (SD and ND; 2 trials), and 8 (CO; 1 trial). The submi ss ion al s o include s data for azoxy st robin. Refer to 48681703

. de 1 for data pertaining to azoxystrobin.

Two trial pairs or s ets (trials C 12-9086 a nd C 12- 9 08 7
, and trials C 13-9083
, C 13-9088, and C 13- 9091) were each conducted by the same principal field investigator ( PFI). A ll trial s reflected use of different tank mixes for all applications. Trial C 13-9091 was conducted in a di f f e rent NAFT A Zone ; thus, H E D concludes that this trial may be counted as a separate trial for purposes of 860.1500 data requirements. Careful examination of the fie l d trial r e cord s for the r e maining trials indicate s that the only difference betwe e n trials C 12-9086 and C 1 2 -9087 was a > 2 0-mile
separ a tion b e tween trial location s, and the only differenc es betw ee n trial s C12-9083 and C 12- 9088 were 5- to 11-day off-set in application dates and a > 25% difference in s pra y volume (**20** 

### gal / A v s

. 2 gallA). HED has concluded that the differences between trial s C12

- 9086 and C 12- 9087 are insufficient to classify them a s s eparate t ria l s ; therefore

, these trials con s titute a single trial with replicate samples for purpos es of 860.1500 da ta requirements. Trials C 1 3 -908 3 and C 1 3

- 90 88 would not normally satisfy the Chern SAC criteria for differentiation of field trials; however, because of the appreciable difference s in spray volumes**(~20** 

### v s

. 

### -2 gallA) and the variation in residue r e sults between the two trial s , H E D conclud e s that these trials may be counted as sep a ra

t e trials. Th e adjustment in trial numbers results in a total of 11 field tri a ls. with five trials cond u cted in NAFT A Zone 5.

DP # 400030 /M RID N o. 48681 7 03 Page I of2 6Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 2 of 26 

### Each trial consisted of one untreated plot and tw o treated plots; separate plots were established for the harvest of forage and hay and for the harv est of grain and straw. At each trial location, the treated plots received two foliar broadcast ap plications of a multiple active ingredient (MAI) suspo-emulsion (SE) formulation (Quilt XcelTM) containing 1.18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole. Applicat ions were targeted at Feekes gr owth stage 5, and 7 days prior to harvest for the forage and hay plots, and at 14 days prior to Feekes 10.54, and Feekes 10.54 for grain and straw plots. Only data pertaining to propiconazole are reviewed in this DER; therefore, the product will be referre d to herein as the 1.02 lb ai/gal SE formulation. Each treated plot received two applications of propiconazo le at 0.1062-0.1180 lb ai/A/application, for a total seasonal rate of 0.2156-0.2331 lb ai/A. Applications were made at 11- to 17-day retreatment intervals (RTIs) using ground equipment in spray volumes of 1.97-31.39 gal/A. A nonionic surfactant (NIS) was added to the spray mixtures for all applicatio ns in eleven trials, and a crop oil concentrate (COC) was added to the spray mixtur es in one trial. Samples of forage and hay were harvested from all trials at preharvest in tervals (PHIs) of 7 and 14 days; grain and straw were harvested at maturity (PHIs of 25-48 days ). Additional forage and hay samples were harvested at PHIs of 0, 3, 7, and 21 days from one trial (in ND) to asse ss residue decline; additional grain and straw samples were collected 14 and 7 days prior to, and 7 days after, maturity. The petitioner noted that no 0-day decl ine samples were collected for hay and that the 3-day samples were actually collected at a 5-day PHI. Hay samples were dried to approximately 10-20% moisture content; drying intervals were not reported.

Application rates in the submission were reporte d in terms of total lb ai/A for combined application of azoxystrobin a nd propiconazole (refer to pg. 11 of MRID 48681703). Individual application rates for azoxystrobi n and propiconazole were calcul ated by the study reviewer based on the ratio of the active ingr edients in the product: 1.18/ 2.2 for azoxystrobin or 1.02/2.2 for propiconazole.

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a high performance liquid chromatography met hod with tandem mass spectrometry detection (LC/MS/MS), Morse Laboratories Meth-180. The lim it of quantitation (LOQ; determined as the lowest limit of method validation; LLMV) was 0.01 ppm. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas chromatography with mass select ive detection (GC/MSD), Nova rtis Crop Protection method AG-626. This is a common moiety method in wh ich all residues of c oncern are converted by base hydrolysis and oxidation to 2,4-DCBA, then de termined as the 2,4-DCBA methyl ester, and reported in propiconazole equivalents. The LOQ (determined as the LLMV) was 0.05 ppm. Samples were analyzed for the triazole metabolit es 1,2,4-triazole (T), tria zole alanine (TA), and triazole acetic acid (TAA) using LC/MS/MS, Morse Laboratories Meth-160, Revision #2. The LOQs (determined as the LLMVs) were: 0.01 ppm fo r T in all matrices, 0.01 ppm for TA in oat forage and straw, 0.1 ppm in oat hay, and 0.04 ppm in oat grain, and 0.01 ppm for TAA in forage, hay, and straw and 0.02 ppm in grain. The methods were adequate for data collection based on acceptable concurrent recovery data. The fortification levels used in concurrent method recovery were adequate to bracket expected residue levels. Concurrent recoveries werePropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 3 of 26 

### corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samp les were stored frozen (<-10 °C at the preparation facility and <-20 °C at the analytical laboratory) from collection to analysis for propiconazole and propiconazole and meta bolites, respectively, for 77-356 days (2.5-11.7 months) and 124-538 days (4.1-17.7 months) for fo rage, 78-358 days (2.6-11.8 months) and 110- 543 days (3.6-17.9 months) for hay, 64-330 days (2.1-10.9 months) and 180-359 days (5.9-11.8 months) for grain, and 59-341 days (1.9-11.2 mo nths) and 182-498 days (6.0-16.4 months) for straw. Sample storage durations prior to analys is for the triazole metabolites were 78-375 days (2.6-12.3 months) for forage, 97-393 days ( 3.2-12.9 months) for hay, 29-371 days (1.0-12.2 months) for grain, and 30-357 days (1.0-11.7 months ) for straw. All samples were analyzed within 0-33 days of extraction. Adequate storag e stability data are av ailable to support the storage durations and cond itions of samples from the submitted field trials.

Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propiconazole at 0.2156-0.2290 lb ai/A, residues (and per trial averages of propiconazole) per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, in/ on forage were: 0.135- 1.26 (0.154-1.17) and 0.431-2.46 (0.499-2.31) ppm at the 7-day PHI; and 0.0316-0.480 (0.0404- 0.449) and 0.303-1.51 (0.389-1.39) ppm at the 14-day PHI; corresponding residues in/on hay were: 0.110-4.46 (0.184-4.26) and 0.629-8.54 (0.798- 8.00) ppm at the 7-day PHI; and 0.0620- 2.69 (0.0680-1.98) and 0.559-5.69 (0.592-4.41) ppm at th e 14-day PHI. In/on grain and straw harvested at PHIs of 25-48 days followi ng two applications at 0.2188-0.2331 lb ai/A, corresponding residues (and pe r trial averages) were: <0.01-0.386 (<0.01-0.368) and 0.0630- 1.61 (0.0649-1.56) ppm in/on grain, and 0.0172- 2.40 (0.0191-1.21) and 0.291-6.07 (0.302-5.10) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of oat forage, hay, grain, and straw. Residues (and per trial averages) of TA and TAA, respectively, in/on forage were 0.0178-0.146 (0.0184-0.128) and <0.01-0.0344 (<0.01-0.0328) ppm at the 7- day PHI; and 0.0189-0.212 (0.0236-0.212) and < 0.01-0.0433 (<0.01-0.0431) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on hay were <0.1-0.334 (<0.1-0.325) and <0.01-0.0645 (<0.01-0.0633) ppm at the 7-day PHI; and <0.1-0.387 (<0.1- 0.373) and <0.01-0.110 (<0.01-0.107) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on gr ain and straw were: 0.0480-0.362 (0.0498-0.353) and <0.02-0.117 (<0.02-0.115) ppm in/on grain; and <0.01-0.0438 (<0.01-0.0435) and <0.01-0.0261 (<0.01-0.0247) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on oat forage and hay. Residues of propiconazole per se and propiconazole and metabolites determined as 2,4- DCBA in/on grain and straw generally increase d with increasing PHI. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals;Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 4 of 26 

### therefore, residue decline coul d not be assessed. Residues of TA in/on forage generally decreased with increasing PHI; residues of TAA generally increased with increasing PHI. Residues of TA and TAA generally decreased with increasing PHI in/on ha y; residues of TA and TAA were variable in/on grain but increased sligh tly from the initial to the final PHI. Residues of TA were below the LOQ at all sampling interv als in/on straw; therefor e, residue decline was not assessed. Residues of TAA in/on straw we re below the LOQ through the 18-day PHI, but increased to 0.022 ppm at the 32-day PHI.

STUDY/WAIVER ACCEPTABILITY/ DEFICIENCIES/CLARIFICATIONS :
Under the conditions and parameters used in the study, the field tria l residue data are classified as scientifically acceptable. The acceptability of this study fo r regulatory purposes is addressed in the forthcoming U.S. EPA Residue Chemistry Summary Document [DP# 400030].

COMPLIANCE :
Signed and dated Good Laboratory Practice (GLP), Quality Assurance, a nd Data Confidentiality statements were provided. No deviations fr om regulatory requirement s were reported which would have an impact on the validity of the study.

A. BACKGROUND INFORMATION

Propiconazole is a triazole-type fungicide that provides broad spectrum disease control through inhibition of sterol biosynthesis in fungi. It is registered to Syngenta Crop Protection for the control of fungal diseases on a variety of crops.

The nomenclature of propiconazole , 1,2,4-triazole (T), triazole al anine (TA), and triazole acetic acid (TAA) are summarized in Table A.1, and th e physicochemical properties of propiconazole are summarized in Table A.2.

TABLE A.1. Nomenclature of Propiconazole and Triazoles. Compound

Common name Propiconazole Company experimental names CGA-64250 IUPAC name 1-[2-(2,4_dichlorophenyl)-4-propyl- 1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole CAS name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1, 3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole N N N

O O
Cl ClPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 5 of 26

TABLE A.1. Nomenclature of Propiconazole and Triazoles.
CAS # 60207-90-1

End-use products/EP Suspo-emulsion (SE) formulation (Quilt XcelTM) containing 1. 18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole Compound

Common name 2,4-DCBA Chemical name 2,4-dichlorobenzoic acid Compound

Common name 1,2,4-Triazole (T)
Chemical name 1 H -1,2,4-triazole CAS registry number 288-88-0 Compound

Common name Triazole alanine or triazolylalanine (TA)
Chemical name α -amino-1 H -1,2,4-triazole-1-propanoic acid CAS registry number 114419-45-3 Compound

Common name Triazole acetic acid or triazolylacetic acid (TAA)
Chemical name 1 H -1,2,4-triazole-1-acetic acid CAS registry number 28711-29-7

TABLE A.2. Physicochemical Properties of Technical Grade Propiconazole.
Parameter Value Reference Boiling point 120°C at 1.9 Pa, >250°C at 101.325 kPa MRID No.:43698701 pH 4.9 @ 25°C (1% aqueous dispersion) MRID No.:43698701 Density 1.289 g/cm3 typical @ 20°C MRID No.: 43698701 Water solubility (20°C) 0.10 g/L at 20°C MRID No.: 41720301

Solvent solubility (temperature not specified) Completely miscible in ethanol, acetone, toluene and n-octanol. n-hexane = 47 g/L MRID No.: 42030201 Vapor pressure at 25°C 4.2 x 10 -7 mm Hg @ 25°C MRID No.: 41720301 Dissociation constant (pK a ) 1.09 MRID No.: 43698701 Octanol/water partition coefficient Log(K OW ) (25 °C) 3.72 @ pH 6.6 MRID No.: 43698701 UV/visible absorption spectrum ( 8 max, nm) Not available MRID No.: 40583703 N H N

N

N N N

O H NH 2

O

N N N

O H OPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 6 of 26 

### B. EXPERIMENTAL DESIGN

B.1. Study Site Information

Twelve field trials we re conducted in the United States du ring the 2009-2010 growing seasons in the NAFTA Growing Zones 1 (PA; 1 trial), 2 (SC; 1 trial), 5 (ND, MN, and IA; 6 trials), 6 (TX; 1 trial), 7 (SD and ND; 2 trials ), and 8 (CO; 1 trial).

Two trial pairs or sets (tri als C12-9086 and C12-9087, and tr ials C13-9083, C13-9088, and C13- 9091) were each conducted by the same principal field i nvestigator (PFI). All trials reflected use of different tank mixes for all applications. Trial C13-9091 was conducted in a different NAFTA Zone; thus, HED concludes that th is trial may be counted as a separate trial for purposes of 860.1500 data requirements. Careful examination of th e field trial records for the remaining trials indicates that the only difference between trials C12-9086 and C12-9087 was a >20-mile separation between trial locati ons, and the only differences be tween trials C12-9083 and C12- 9088 were 5- to 11-day off-set in application da tes and a >25% difference in spray volume (~20 gal/A vs. 2 gal/A). HED has concluded that the differences between trials C12-9086 and C12- 9087 are insufficient to classify them as separate trials; therefore, these trials cons titute a single trial with replicate samples for purposes of 860.1500 data requirements. Trials C13-9083 and C13-9088 would not normally satisfy the ChemSAC criteria for differentiation of field trials; however, because of the apprecia ble differences in spray volumes (~20 vs. ~2 gal/A) and the variation in residue results be tween the two trials, HED concludes that these trials may be counted as separate trials.

Each trial consisted of one untreated plot and tw o treated plots; separate plots were established for the harvest of forage and hay and for the harv est of grain and straw. At each trial location, the treated plots received two fo liar broadcast applicati ons of a 1.02 lb ai/gal SE formulation of azoxystrobin (Quilt XcelTM). Applications were ta rgeted at Feekes growth stage 5, and 7 days prior to harvest for the forage and hay plots, and at 14 days prior to Feekes 10.54, and Feekes 10.54 for grain and straw plots. Each treated plot received two applications of propiconazole at 0.1062-0.1180 lb ai/A/application, for a total seasonal rate of 0.2156-0.2331 lb ai/A. Applications were made at 11- to 17-day RT Is using ground equipment in spray volumes of 1.97-31.39 gal/A. An NIS was added to the spray mixt ures for all applications in eleven trials, and a COC was added to the spray mixtures in one trial. Samples of forage and hay were harvested from all trials at PHIs of 7 and 14 da ys; grain and straw were harvested at maturity (PHIs of 25-48 days). Additional forage and hay samples were harvested at PHIs of 0, 3, 7, and 21 days from one trial (in ND) to assess residue decline; additional grain and straw samples were collected 14 and 7 days prior to, and 7 days after, maturity. The petitioner noted that no 0- day decline samples were collected for hay and that the 3-day samples were actually collected at a 5-day PHI. Hay samples were dried to a pproximately 10-20% moisture content; drying intervals were not reported.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 7 of 26 

### Maintenance pesticides and fertilizers were us ed as needed to produce a commercial quality crop. Monthly temperature ranges and total monthly precipitation were provided for each trial, as well as the historical averag es. Irrigation was used to supplement rainfall as needed. The petitioner stated that actual te mperature recordings were within average historical values, and actual average rainfall was within historical ra infall averages. In trial E04-9081 (PA), the second application to treated plot 3 (g rain and straw) was made at Feekes stages 10.54-11.1 (vs. 10.54); however, the majority of the plot was in the correct growth stag e. In trial E11-9082 (SC), the second application to treated plot 3 (grain and straw) was made at Feekes Growth Stage 10.3 (vs. 10.54). In trial C13-9088 (ND), the second appli cation to treated plot 3 was made at BBCH 75 (vs. Feekes 10.54, which corresponds to BBCH 71) due to faster growth caused by weather. In trial C13-9091 (ND), the second application to treated plot 3 was made at BBCH 69 due to delayed maturation caused by the weather. In Tria l C16-9090, the first applic ation to treated plot 2 (forage and hay) occurred at BBCH 23, rather than at BBCH 30, which corresponds to Feekes Growth Stage 5. Although variations in temp erature and precipitat ion were reported, no abnormal weather events were indicated to have adversely impacted crop yields or crop growth and development at the remaining trial sites.

Trial conditions are presented in Table B.1.1. Th e study use pattern is presented in Table B.1.2, and the crop varieties grown are identified in Table C.3.

TABLE B.1.1 Trial Site Conditions

. Trial Identification: City, State; Year (Trial No.) Soil characteristics Type %OM pH CEC (meq/100 g) Germansville, PA; 2009 (E04-9081) Loam 2.4 6.5 9.7 Elko, SC; 2010 (E11-9082) Loamy sand 1.1 6.8 3.1 Northwood, ND; 2009 (C13-9083) Loam 4.7 6.9 19.8 Geneva, MN; 2009 (C09-9084) Sand y clay loam 4.1 6.1 28.6 Bagley, IA; 2009 (C30-9085) Clay loam 3.4 7.2 26.0 Ayr, ND; 2009 (C12-9086) Loam 4.7 6.6 18.1 Gardner, ND; 2009 (C12-9087) Clay loam 3.2 7.6 29.8 Northwood, ND; 2009 (C13-9088) Sa ndy clay loam 4.7 6.9 27.5 Uvalde, TX; 2010 (W07-9089) Clay 2.5 8.0 43.4 White Lake, SD; 2009 (C16-9090) Clay loam 3.4 7.0 29.2 Carrington, ND; 2009 (C13-9091) Sandy loam 2.7 6.9 24.0 Ault, CO; 2009 (W12-9092) Sandy loam 1.2 6.9 33.2Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 8 of 26

TABLE B.1.2. Stud y Use Pattern. Location (City, State; Year) Trial ID 1 EP 2 Plot Application Information Tank Mix/ Adjuvants 5 Method; Timing Volume (gal/A) Rate 3 (lb ai/A) RTI 4 (days) Total Rate 3 (lb ai/A) Germansville, PA; 2009 (E04-9081) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes Scale 5 30.32 0.1136 -- 0.2290 NIS

2. Foliar broadcast; Feekes Scale 7 30.67 0.1154 11

3 [Grain and

Straw] 1. Foliar broadcast; Feekes Scale 10.5 30.58 0.1150 -- 0.2331 NIS

2. Foliar broadcast; Feekes 10.54-11.1 31.39 0.1180 11

Elko, SC; 2010 (E11- 9082) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes Stage 5 22.35 0.1108 -- 0.2217 NIS

2. Foliar broadcast; BBCH 32 21.93 0.1109 13
3 [Grain and

Straw] 1. Foliar broadcast; Feekes Stage 10.0 21.89 0.1111 -- 0.2219 NIS

2. Foliar broadcast; Feekes Stage 10.3 21.29 0.1108 13

Northwood, ND; 2009 (C13-9083) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 22 20.21 0.1122 -- 0.2230 NIS 2. Foliar broadcast; BBCH 55 19.87 0.1108 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 39 19.68 0.1097 -- 0.2213 NIS 2. Foliar broadcast; BBCH 71 20.03 0.1116 15

Geneva, MN; 2009 (C09- 9084) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 15.77 0.1117 -- 0.2248 NIS 2. Foliar broadcast; Feekes 7 16.36 0.1131 14
3 [Grain and

Straw] 1. Foliar broadcast; Feekes 9 17.57 0.1105 -- 0.2225 NIS 2. Foliar broadcast; Feekes 10.54 18.57 0.1119 15

Bagley, IA; 2009 (C30- 9085) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 10.29 0.1094 -- 0.2156 NIS 2. Foliar broadcast; 14 days after Feekes 5 9.15 0.1062 14

3 [Grain and

Straw] 1. Foliar broadcast; 14 days prior to Feekes 10.54 10.41 0.1062 -- 0.2188 NIS

2. Foliar broadcast; Feekes 10.54 8.17 0.1127 14 Ayr, ND; 2009 (C12-9086) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 31 10.15 0.1131 -- 0.2253 NIS 2. Foliar broadcast; BBCH 49 15.21 0.1122 13

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 52 15.09 0.1110 -- 0.2232 NIS 2. Foliar broadcast; BBCH 70 15.24 0.1122 14

Gardner, ND; 2009 (C12- 9087) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 31 10.07 0.1118 -- 0.2259 NIS 2. Foliar broadcast; BBCH 49 15.44 0.1141 13

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 52 15.15 0.1119 -- 0.2284 NIS 2. Foliar broadcast; BBCH 70 15.77 0.1165 13Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 9 of 26

TABLE B.1.2. Stud y Use Pattern. Location (City, State; Year) Trial ID 1 EP 2 Plot Application Information Tank Mix/ Adjuvants 5 Method; Timing Volume (gal/A) Rate 3 (lb ai/A) RTI 4 (days) Total Rate 3 (lb ai/A) Northwood, ND; 2009 (C13-9088) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 30 1.99 0.1108 -- 0.2205 NIS 2. Foliar broadcast; BBCH 71 1.97 0.1097 17

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 43 2.00 0.1114 -- 0.2216 NIS 2. Foliar broadcast; BBCH 75 1.98 0.1103 15

Uvalde, TX; 2010 (W07- 9089) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 30 15.81 0.1118 -- 0.2269 NIS 2. Foliar broadcast; BBCH 33 16.64 0.1151 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 60 22.81 0.1128 -- 0.2250 NIS 2. Foliar broadcast; BBCH 71 18.71 0.1122 14

White Lake, SD; 2009 (C16-9090) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 23 21.35 0.1127 -- 0.2255 NIS 2. Foliar broadcast; BBCH 43 18.87 0.1128 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 43 18.70 0.1116 -- 0.2248 NIS 2. Foliar broadcast; BBCH 71 19.90 0.1132 17

Carrington, ND; 2009 (C13-9091) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 16 20.22 0.1127 -- 0.2244 COC 2. Foliar broadcast; BBCH 55 20.04 0.1117 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 37 19.77 0.1095 -- 0.2201 COC 2. Foliar broadcast; BBCH 69 19.86 0.1107 14

Ault, CO; 2009 (W12-9092) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 16.76 0.1140 -- 0.2273 NIS 2. Foliar broadcast; Feekes 10 16.67 0.1134 14

3 [Grain and

Straw] 1. Foliar broadcast; Feekes 10.2 17.67 0.1101 -- 0.2252 NIS 2. Foliar broadcast; Feekes 10.54 18.14 0.1151 14

1 HED has concluded that trials C12-9086 and C12-9087 constitute a single trial with replicate samples for purposes of 860.1500 data requirements.
2 EP = End-use Product; a multiple active ingredient (MAI) sus po-emulsion (SE) formulation (Quilt XcelTM) containing 1.18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole.
3 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
4 RTI = Retreatment Interval.
5 NIS = non-ionic surfactant. COC = crop oil concentrate.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 10 of 26

TABLE B.1.3. Trial Numbers and Geographical Locations

. NAFTA Growing Regions Oats Submitted Requested 1

Canada U.S.
1 1 -- 1/1
1A -- -- --
2 1 -- 1/1
3 -- -- --
4 -- -- --
5 5 2 -- 9/6
5A -- -- --
5B -- -- --
6 1 -- 1/1
7 2 -- 3/2
7A -- -- --
8 1 -- 1/1
9 -- -- --
10 -- -- --
11 -- -- --
12 -- -- --
13 -- -- --
14 -- -- --
15 -- -- --
16 -- -- --
17 -- -- --
18 -- -- --
19 -- -- --
20 -- -- --
21 -- -- --
Total 11 2 16/12

1 As per OCSPP 860.1500, Table 5 for oats. The second number reflects a 25% reduction in the number of trials allowed for the crop as a representative commodity in support of a crop group/subg roup tolerance or when applicat ion results in no quantifiable residues.
2 HED has concluded that trials C12-9086 and C12-9087 constitute a single trial with replicate samples for purposes of 860.1500 data requirements.


### B.2. Sample Handling and Preparation

Single control and duplicate treated samples of forage (~3 lb) and hay (~2 lb) were harvested at PHIs of 7 and 14 days; samples of grain (~3 lb) a nd straw (~2 lb) were harvested at maturity (25- to 48-day PHIs). Additional forage and hay sa mples were harvested at PHIs of 0, 3, 7, and 21 days from one trial to assess residue decline; additional grain and straw samples were collected at 14 and 7 days prior to, and 7 days after, maturity. Hay samp les were dried to approximately 10-20% moisture content; drying inte rvals were not reported. The sa mples were placed in frozen storage at the field sites (inter val between collection and freezi ng not reported). All samples were shipped frozen within 0-56 days of collect ion by freezer truck or overnight courier to thePropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 11 of 26 

### preparation facility, Syngenta Cr op Protection (Greensboro, NC), where they were maintained frozen (<-10 °C) prior to and following preparat ion. In preparation fo r analysis, any adhering soil and inedible portio ns of oats were removed from the samples by light brushing. Samples were homogenized by grinding in a Hobart food cutter in the presen ce of dry ice. Within 12-299 days of receipt at the prepar ation facility, samples were shipped frozen via FedEx to the analytical laboratory, Morse Labor atories (Sacramento, CA), where they were maintained frozen (~ -20 °C) prior to analysis.

B.3. Analytical Methodology

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a LC/MS/MS method, Morse Laboratories Meth -180. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas GC/MSD, Novartis Crop Prot ection method AG-626. This is a common moiety method in which all residues of concern are converted by base hydrolysis and oxidation to 2,4-DCBA, then determined as the 2,4-DCBA methyl ester, and re ported in propiconazole equivalents. Samples were analyzed for the triazole metabolites T, TA, and TAA using LC/MS/MS, Morse Laboratories Meth-160, Revision #2.

For determination of residues of propiconazole per se , samples were extracted with methanol:water (80:20, v:v) and filtered. Water and saturated NaCl solution were added to an aliquot of the filtrate, which was then partitioned three times with hexane. The combined hexane extracts were evaporated to dryness, reconstitu ted in acetonitrile:wate r (30:70, v:v), and then analyzed using LC/MS/MS. The LOQ (determined as the LLMV) was 0.01 ppm; the limit of detection (LOD) was not reported.

For determination of residues of propiconazo le and metabolites conve rtible to 2,4-DCBA, samples were refluxed with methanol:ammonium hydroxide (80:20, v:v). An aliquot of the extract was evaporated to dryness. The residues were dissolved in aqueous NaOH and heated in the presence of potassium permanganate for oxidation of propiconazole and metabolites to 2,4- DCBA. The sample was acidified with HCl and pa rtitioned with hexane:eth yl ether (90:10, v:v). The organic phase was evaporated to dryness an d derivatized with diazomethane to form the methyl ester of 2,4-DCBA. The derivatized extract was evaporated to dryness, reconstituted in hexane, and purified using an al umina solid phase extraction (SPE ) cartridge. The sample was reduced to a known volume using nitrogen evaporat ion and then analyzed using GC/MSD. The LOQ (determined as the LLMV) was 0.05 ppm; the LOD was not reported.

For determination of T, TA, and TAA, samples we re extracted with methanol:water (80:20, v:v). Following the addition of Celite, the extracts were vacuum filtered, rinsed, and brought to volume with methanol:water (80:20, v:v). For dete rmination of TAA, an aliquot of the extract were purified by SPE and then derivatized by HC l/butanol esterification. The TA aliquot underwent two derivatizations: an esterificat ion using HCl/butanol and an acylation using heptafluorobutyric anhydride (HFBA). The T al iquot was directly derivatized with dansyl chloride to produce the dansyl derivative of 1,2,4-t riazole and partitioned into ethyl acetate. AllPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 12 of 26 

### metabolite extracts were then evaporated to dr yness, redissolved in acetonitrile:water (30:70, v:v), and analyzed using LC/MS/MS detection. The LOQs (determined as the LLMVs) were: 0.01 ppm for T in all matrices, 0.01 ppm for TA in oat forage and straw, 0.1 ppm in oat hay, and 0.04 ppm in oat grain, and 0.01 ppm for TAA in forage, hay, and straw and 0.02 ppm in grain. The LODs were not reported.

The methods were validated in conjunc tion with the field trial samples.

C. RESULTS AND DISCUSSION

Sample storage conditions and durations are report ed in Table C.2. Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samples were stored frozen (<-10 °C at the preparation facility and <- 20 °C at the analytical labor atory) from collection to analysis for propiconazole and propiconazole and metabolites, respectivel y, for 77-356 days (2.5-11.7 months) and 124-538 days (4.1-17.7 months) for forage, 78-358 da ys (2.6-11.8 months) and 110-543 days (3.6-17.9 months) for hay, 64-330 days (2.1-10.9 months) and 180-359 days (5.9-11.8 months) for grain, and 59-341 days (1.9-11.2 months) and 182-498 days (6.0-16.4 months) for straw. Sample storage durations prior to anal ysis for the triazole metabolit es were 78-375 days (2.6-12.3 months) for forage, 97-393 days (3.2-12.9 mont hs) for hay, 29-371 days (1.0-12.2 months) for grain, and 30-357 days (1.0-11.7 months) for straw. All samples were analyzed within 0-33 days of extraction. Acceptable storage stability data for propiconazole are available indicating that residues of propiconazole and metabolites conve rtible to 2,4-DCBA are stable during frozen storage for up to: 38 months in/on grass fo rage and straw (DP# 210742, 3/15/95, M. Rodriguez); and for up to 36 months in/on wheat grain (DP# 240856, 2/23/05, T. Morton). In addition, acceptable data have been submitted indicating that residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/on soybean seed (refer to 48681707.der, currently under review). Accep table storage stability data for the triazole metabolites are available (DP# 363016, 1/12/12, D. Drew; 47606601.der) indicating that residues of T, TA, and TAA are stable during frozen stor age in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but decline thereafter. Additional storage stability data for the triazole metabolites (DP# 388246, 5/28/ 08, M. Doherty) indicate that residues of TAA are stable in/on wheat grain, forage, hay, an d straw for up to 13 months, and that residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. These data are adequate to support the storage durations and conditions of samples from the submitted field trials.

Concurrent method recovery data for the GC/M SD and LC/MS/MS methods are presented in Table C.1. Samples were fortified at 0.01-10.0 ppm with propiconazole , at 0.05-20 ppm with propiconazole and metabolites, at 0.01-0.1 ppm with T, at 0.0 1-5.0 ppm with TA, and at 0.01-1.0 ppm with TAA. The methods were adequate fo r data collection based on acceptable concurrent recovery data. Recoveries were within the accep table range of 70-120%. The fortification levels used in concurrent method recovery were adequate to bracket exp ected residue levels. ApparentPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 13 of 26 

### residues of propiconazole and metabolite T were at or below the LOQ in/on all samples of untreated oats. Quantifiable apparent residues of propiconazole were observed in/on one sample of hay (0.0107 ppm). Quantifiable apparent residues of propiconazole and metabolites determined as 2,4-DCBA were observed in/on four samples of untreated forage (0.05-0.13 ppm), one sample of hay (0.08 ppm), and one sample of grain (0.05 ppm). Quantifiable apparent residues of TA were observed in/on twenty-one samples of untreated forage (0.01-0.14 ppm), nine samples of hay (0.11-0.25 ppm), nine samples of grain (0.05-0.36 ppm), and three samples of straw (0.01-0.02 ppm). Quantifiable apparent residues of TAA were observed in/on eight samples of untreated forage (0.01-0.04 ppm), thirteen samples of hay (0.01-0.07 ppm), eight samples of grain (0.04-0.11 ppm), and six samples of straw (0.01-0.04 ppm). The petitioner attributed the occurrence of re sidues of TA and TAA in/on untreat ed samples to the widespread use of triazoles and th e non-specific nature of the comm on moiety method of analysis. Concurrent recoveries were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Residue data from the oats field trials are reported in Tables C.3.1 (propiconazole) and C.3.2 (triazole metabolites), and the residue data for oats are summarized in Table C.4. Following two foliar broadcast applications of the 1.02 lb ai/gal SE formul ation of propiconazole at 0.2156- 0.2290 lb ai/A, residues (and per tria l averages of propiconazole) per se and propiconazole and metabolites determined as 2,4-DCBA, respect ively, in/on forage were: 0.135-1.26 (0.154-1.17) and 0.431-2.46 (0.499-2.31) ppm at the 7-da y PHI; and 0.0316-0.480 (0.0404-0.449) and 0.303- 1.51 (0.389-1.39) ppm at the 14-day PHI; corre sponding residues in/on hay were: 0.110-4.46 (0.184-4.26) and 0.629-8.54 (0.798-8.00) ppm at the 7-day PHI; and 0.0620-2.69 (0.0680-1.98) and 0.559-5.69 (0.592-4.41) ppm at the 14-day PHI. In/on grain and straw harvested at PHIs of 25-48 days following two applications at 0.2188- 0.2331 lb ai/A, corresponding residues (and per trial averages) were: <0.01-0.386 (<0.01- 0.368) and 0.0630-1.61 (0.0649-1.56) ppm in/on grain, and 0.0172-2.40 (0.0191-1.21) and 0.291-6.07 (0 .302-5.10) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of oat forage, hay, grain, and straw. Residues (and per trial averages) of TA and TAA, respectively, in/on forage were 0.0178-0.146 (0.0184-0.128) and <0.01-0.0344 (<0.01-0.0328) ppm at the 7- day PHI; and 0.0189-0.212 (0.0236-0.212) and < 0.01-0.0433 (<0.01-0.0431) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on hay were <0.1-0.334 (<0.1-0.325) and <0.01-0.0645 (<0.01-0.0633) ppm at the 7-day PHI; and <0.1-0.387 (<0.1- 0.373) and <0.01-0.110 (<0.01-0.107) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on gr ain and straw were: 0.0480-0.362 (0.0498-0.353) and <0.02-0.117 (<0.02-0.115) ppm in/on grain; and <0.01-0.0438 (<0.01-0.0435) and <0.01-0.0261 (<0.01-0.0247) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on oat forage and hay. Residues of propiconazole per se and propiconazole and metabolites determined as 2,4- DCBA in/on grain and straw generally increase d with increasing PHI. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals;Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 14 of 26 

### therefore, residue decline coul d not be assessed. Residues of TA in/on forage generally decreased with increasing PHI; residues of TAA generally increased with increasing PHI. Residues of TA and TAA generally decreased with increasing PHI in/on ha y; residues of TA and TAA were variable in/on grain but increased sligh tly from the initial to the final PHI. Residues of TA were below the LOQ at all sampling interv als in/on straw; therefor e, residue decline was not assessed. Residues of TAA in/on straw we re below the LOQ through the 18-day PHI, but increased to 0.022 ppm at the 32-day PHI.

TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Oats. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

LC/MS/MS Meth-180 Oat Forage Propiconazole 0.01 7 82, 79, 87, 74, 76, 78, 84 80 ± 4.6 0.1 7 75, 90, 87, 90, 72, 82, 86 83 ± 7.2
3.0 1 89 89 Oat Hay 0.01 7 94, 93, 86, 89, 99, 89, 89 91 ± 4.3 0.1 7 92, 94, 83, 81, 91, 77, 76 85 ± 7.4
5.0 1 99 99
10.0 1 89 89 Oat Grain 0.01 4 88, 117, 74, 101 95 ± 18 0.1 3 93, 98, 70 87 ± 15
0.5 1 109 109 Oat Straw 0.01 4 96, 106, 86, 87 94 ± 9.3 0.1 3 92, 98, 82 91 ± 8.1
5.0 1 86 86
GC/MSD method AG-626 Oat Forage Propiconazole and metabolites determined as 2,4- DCBA 0.05 9 102, 73, 80, 106, 112, 91, 107, 119, 97 99 ± 15 0.5 6 71, 76, 96, 87, 99, 74 84 ± 12 2.5 2 102, 95 98
5.0 1 95 95 Oat Hay 0.05 7 85, 94, 72, 77, 108, 102, 79 88 ± 14 0.5 3 110, 76, 70 85 ± 22 2.5 5 84, 76, 83, 93, 85 84 ± 6.1
10 1 88 88
20 1 80 80 Oat Grain 0.05 5 118, 83, 96, 104, 81 96 ± 15 0.5 4 91, 81, 80, 95 87 ± 7.4
5.0 1 92 92 Oat Straw 0.05 5 96, 82, 89, 73, 104 89 ± 12 0.5 2 81, 83 82 2.5 2 90, 84 87
10 1 73 73Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 15 of 26

TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Oats. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

LC/MS/MS Meth-160 Oat Forage T 0.01 8 89, 77, 75, 88, 97, 95, 90, 106 90 ± 10 0.1 8 92, 84, 77, 75, 90, 93, 93, 90 87 ± 7.2
TA 0.01 1 90 90 0.05 4 102, 101, 86, 110 100 ± 10 0.2 4 96, 111, 101, 88 99 ± 9.6 0.5 4 100, 100, 97, 108 101 ± 4.7 2.0 4 94, 91, 94, 95 94 ± 1.7 TAA 0.01 4 108, 115, 92, 111 106 ± 10 0.04 4 93, 101, 99, 108 100 ± 6.2 0.1 4 107, 109, 106, 103 106 ± 2.5 0.4 4 97, 98, 98, 116, 102 ± 9.2 Oat Hay T 0.01 9 101, 78, 98, 89, 80, 81, 106, 79, 81 88 ± 11 0.1 9 101, 83, 94, 80, 71, 92, 107, 70, 84 87 ± 13 TA 0.1 3 109, 99, 96 101 ± 6.8 0.15 5 96, 92, 91, 95, 81 91 ± 6.0
0.5 1 81 81 1.0 3 110, 100, 104 105 ± 5.0 1.5 5 91, 91, 89, 92, 89 90 ± 1.3
5.0 1 81 81 TAA 0.01 8 95, 105, 107, 112, 116, 99, 96, 112 105 ± 7.9
0.07 1 101 101 0.1 9 103, 95, 95, 104, 102, 112, 102, 98, 104 102 ± 5.3
0.7 1 102 102
1.0 1 99 99 Oat Grain T 0.01 5 87, 87, 87, 99, 110 94 ± 10 0.1 5 87, 93, 81, 93, 120 95 ± 15
TA 0.04 1 108 108
0.06 1 96 96 0.1 3 89, 103, 110 101 ± 11
0.4 1 91 91
0.6 1 91 91 1.0 3 85, 91, 97 91 ± 6.0
TAA 0.02 1 109 109 0.04 3 95, 93, 111 100 ± 9.9
0.1 1 91 91
0.2 1 100 100 0.4 3 92, 94, 97 94 ± 2.5
1.0 1 87 87Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 16 of 26

TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Oats. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

Oat Straw T 0.01 5 109, 89, 78, 90, 98 93 ± 12 0.1 5 83, 80, 72, 92, 113 88 ± 16
TA 0.01 1 83 83 0.04 4 96, 93, 92, 89 92 ± 2.9
0.1 1 93 93 0.4 4 90, 100, 100, 102 98 ± 5.4 TAA 0.01 5 99, 108, 105, 95, 97 101 ± 5.5 0.1 5 96, 107, 106, 113, 94 103 ± 8.0

1 Concurrent recoveries we re corrected for apparent residues in control samples.
2 Standard deviations are calculate d only for fortification levels having ≥ 3 samples.
3 Means and standard deviations were calculated by the petitioner

TABLE C.2. Summary of Storage Conditions

. Matrix Analyte Storage Temperature (°C) Actual Storage Duration 1 Limit of Demonstrated Storage Stability Propiconazole Forage Propiconazole Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 77-356 days (2.5-11.7 months) Re sidues of propiconazole and metabolites convertible to 2,4- DCBA are stable during frozen storage for up to: 38 months in/on grass forage and straw 2 ; and for up to 36 months in/on wheat grain 3

. Residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/on soybean seed 4

. Propiconazole and Metabolites 124-538 days (4.1-17.7 months)

Hay Propiconazole 78-358 days (2.6-11.8 months) Propiconazole and Metabolites 110-543 days (3.6-17.9 months)

Grain Propiconazole 64-330 days (2.1-10.9 months) Propiconazole and Metabolites 180-359 days (5.9-11.8 months)

Straw Propiconazole 59-341 days (1.9-11.2 months) Propiconazole and Metabolites 182-498 days (6.0-16.4 months)

Triazole metabolites Forage T Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 80-375 days (2.6-12.3 months) Residues of T, TA, and TAA are stable during frozen storage in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but decline thereafter. 5 Residues of TAA are stable in/on wheat grain, forage, hay, and straw for up to 13 months, and residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. 6 TA 78-373 days (2.6-12.3 months) TAA 80-375 days (2.6-12.3 months) Hay T 97-383 days (3.2-12.6 months) TA 99-381 days (3.3-12.5 months) TAA 97-393 days (3.2-12.9 months) Grain T 29-349 days (1.0-11.5 months) TA 29-345 days (1.0-11.3 months) TAA 49-371 days (1.6-12.2 months) Straw T 31-351 days (1.0-11.5 months) TA 30-353 days (1.0-11.6 months) TAA 43-357 days (1.4-11.7 months)

1 Interval from harvest to analysis. Extracts were stored 0-33 days prior to analysis.
2 DP# 210742, 3/15/95, M. Rodriguez.
3 DP# 240856, 2/23/05, T. Morton.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 17 of 26 4 Refer to 48681707.der, currently under review.
5 DP# 363016, 1/12/12, D. Drew; 47606601.der.
6 DP# 388246, 5/28/08, M. Doherty.

TABLE C.3.1 Residue Data for Propiconazole fr om Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
Propiconazole Propiconazole and Metabolites Germansville, PA; 2009 (E04- 9081) 1 Armor Forage 0.2290 7 1.24, 1. 09 [1.17] 1.75, 1.82 [1.79] 14 0.420, 0.422 [0.421] 1.20, 1.37 [1.29] Hay 7 2.02, 2.07 [2.05] 4.47, 5.17 [4.82] 14 1.30, 1.14 [1.22] 3.85, 4.57 [4.21] Grain 0.2331 28 0.350, 0.386 [0.368] 1.32, 1.61 [1.47] Straw 29 0.728, 0.872 [0.800] 6.07, 4.12 [5.10] Elko, SC; 2010 (E11-9082) 2 Horizon 270 Forage 0.2217 7 0.860, 0.780 [0.820] 2.46, 2.16 [2.31] 14 0.308, 0.335 [0.322] 1.26, 1.51 [1.39] Hay 7 1.34, 1.20 [1.27] 3.30, 3.16 [3.23] 14 0.645, 0.595 [0.620] 2.31, 1.66 [1.99] Grain 0.2219 44 <0.01, <0.01 [<0.01] 0.257, 0.265 [0.261] Straw 44 0.0823, 0.0964 [0. 0894] 2.55, 2.89 [2.72] Northwood, ND; 2009 (C13-9083) 5 Jerry Forage 0.2230 7 0.203, 0. 196 [0.200] 0.811, 0.746 [0.779] 14 0.0699, 0.0802 [0.0751] 0.551, 0.538 [0.545] Hay 7 0.376, 0.332 [0.354] 0.957, 1.19 [1.07] 14 0.171, 0.194 [0.183] 1.41, 1.19 [1.30] Grain 0.2213 33 0.0166, 0.0218 [0 .0192] 0.0858, 0.0893 [0.0876]
Straw 33 0.0509, 0.0532 [0. 0521] 1.16, 1.09 [1.13]
Geneva, MN; 2009 (C09-9084) 5 Morton Forage 0.2248 7 0.828, 0. 858 [0.843] 1.47, 1.55 [1.51] 14 0.145, 0.151 [0.148] 0.899, 0.855 [0.877] Hay 7 1.10, 1.05 [1.08] 3.14, 3.42 [3.28] 14 0.436, 0.458 [0.447] 1.79, 1.99 [1.89] Grain 0.2225 48 0.0346, 0.0437 [0.0392] 0.117, 0.310 [0.214] Straw 48 0.0468, 0.0611 [0. 0540] 1.13, 1.32 [1.23] Bagley, IA; 2009 (C30-9085) 5 Reeves Forage 0.2156 7 0.135, 0.176 [0.156] 0.568, 0.431 [0.500] 14 0.0491, 0.0316 [0.0404] 0.541, 0.303 [0.422] Hay 7 0.258, 0.110 [0.184] 0.967, 0.629 [0.798] 14 0.0932, 0.0690 [0.0811] 0.960, 0.787 [0.874] Grain 0.2188 32 0.0858, 0.0783 [0.0821] 0.774, 0.910 [0.842] Straw 32 0.0172, 0.0210 [0.0191] 0.663, 1.21 [0.937]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 18 of 26

TABLE C.3.1 Residue Data for Propiconazole fr om Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
Propiconazole Propiconazole and Metabolites Ayr, ND; 2009 and Gardner, ND; 2009 (C12- 9086 and C12- 9087) Target PHI 5 Morton Forage 0.2253- 0.2259 7 0.976, 1.23, 1.26 [1.16] 1.77, 2.12, 2.02 [1.97]
14 0.424, 0.464, 0.428, 0.480 [0.449] 1.38, 1.18, 1.25, 1.41 [1.31] Hay 7 3.91, 4.40, 4.46 [4.26] 7.14, 8.33, 8.54 [8.00]
14 1.72, 1.70, 1.81, 2.69 [1.98] 4.88, 3.00, 4.07, 5.69 [4.41]
Grain 0.2232- 0.2284 44 0.0535, 0.0674, 0.311, 0.355 [0.197] 0.269, 0.173, 0.862, 0.968 [0.568] 25 Straw 44 0.357, 0.159, 2.40, 1.91 [1.21] 3.20, 1.56, 6.07, 5.86 [4.17] 25 Gardner, ND; 2009 (C12-9087) Additional Decline PHIs 5 Morton Forage 0.2259 0 2.76 2.95
3 2.42 2.82
21 0.700 1.82 Hay 5 7.38 12.2
21 1.56 4.52
Grain 0.2284 11 0.117 0.337
18 0.252 0.688
32 0.225 0.642
Straw 11 0.948 1.79
18 1.32 3.43
32 1.16 3.78 Northwood, ND; 2009 (C13-9088) 5 Jerry Forage 0.2205 7 0.626, 0. 566 [0.596] 1.46, 1.34 [1.40] 14 0.359, 0.291 [0.325] 1.49, 1.12 [1.31] Hay 7 1.58, 1.19 [1.39] 2.52, 2.17 [2.35] 14 0.499, 0.314 [0.407] 1.84, 1.35 [1.60] Grain 0.2216 28 0.0138, 0.0169 [0 .0154] 0.0630, 0.0667 [0.0649] Straw 28 0.0490, 0.0473 [0.0482] 0.291, 0.312 [0.302] Uvalde, TX; 2010 (W07- 9089) 6 BOB Forage 0.2269 7 0.870, 1.15 [1.01] 1.42, 1.94 [1.68] 14 0.341, 0.408 [0.375] 1.00, 0.949 [0.975] Hay 7 2.05, 2.83 [2.44] 3.81, 5.70 [4.76] 14 1.06, 0.775 [0.918] 2.97, 2.32 [2.65] Grain 0.2250 35 0.252, 0.269 [0.261] 1.59, 1.52 [1.56] Straw 35 0.418, 0.266 [0.342] 3.03, 1.92 [2.48] White Lake, SD; 2009 (C16-9090) 7 Stallion Forage 0.2255 7 0.712, 0. 924 [0.818] 1.31, 1.55 [1.43] 14 0.182, 0.171 [0.177] 0.588, 0.666 [0.627] Hay 7 3.49, 3.81 [3.65] 5.56, 6.92 [6.24] 14 0.439, 0.640 [0.540] 2.59, 2.78 [2.69] Grain 0.2248 36 0.0243, 0.0229 [0.0236] 0.155, 0.208 [0.182] Straw 36 0.0390, 0.0402 [0. 0396] 1.43, 1.33 [1.38]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 19 of 26

TABLE C.3.1 Residue Data for Propiconazole fr om Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
Propiconazole Propiconazole and Metabolites Carrington, ND; 2009 (C13-9091) 7 Jerry Forage 0.2244 7 0.592, 0. 716 [0.654] 1.36, 1.60 [1.48] 14 0.237, 0.286 [0.262] 0.905, 1.05 [0.978] Hay 7 1.43, 1.33 [1.38] 2.46, 2.88 [2.67] 14 0.864, 1.11 [0.987] 2.64, 3.47 [3.06] Grain 0.2201 39 0.0335, 0.0332 [0.0334] 0.163, 0.143 [0.153] Straw 39 0.384, 0.374 [0.379] 3.16, 2.66 [2.91] Ault, CO; 2009 (W12-9092) 8 Jerry Forage 0.2273 7 0.161, 0. 146 [0.154] 0.522, 0.476 [0.499] 14 0.0496, 0.0449 [0.0473] 0.381, 0.397 [0.389] Hay 7 0.243, 0.241 [0.242] 0.859, 0.950 [0.905] 14 0.0620, 0.0740 [0.0680] 0.559, 0.624 [0.592] Grain 0.2252 28 0.0479, 0.0509 [0.0494] 0.184, 0.206 [0.195] Straw 28 0.330, 0.411 [0.371] 1.86, 2.23 [2.05]

1 HED has concluded that trials C12-9086 and C12-9087 constitute a single trial with replicate samples for purposes of 860.1500 data requirements.
2 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
3 For the decline trial, the target PHIs are bolded

. 4 Residues were determ ined as propiconazole per se (LOQ = 0.01 ppm) and as propiconazole and metabolites convertible to 2,4- DCBA (determined as 2,4-DCBA; LOQ = 0.05 ppm). LODs were not reported. Per trial averages were calculated by the study reviewer using the LOQ for values reported as <LOQ.

TABLE C.3.2 Residue Data for Triazole Metabolites from Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
T TA TAA

Germansville, PA; 2009 (E04- 9081) 1 Armor Forage 0.2290 7 <0.01, ND [<0.01] 0.109, 0.146[0.128] <0.01, 0.0134 [<0.0117] 14 ND, ND [<0.01] 0.211, 0.212 [0.212] 0.0428, 0.0433 [0.0431] Hay 7 <0.01, <0.01 [<0.01] 0.315, 0.334 [0.325] 0.0330, 0.0332 [0.0331] 14 <0.01, <0.01 [<0.01] 0.387, 0.359 [0.373] 0.110, 0.103 [0.107] Grain 0.2331 28 <0.01, <0.01 [<0.01] 0.273, 0.258 [0.266] 0.0660, 0.0640 [0.0650] Straw 29 <0.01, <0.01 [<0.01] 0.0431, 0.0438 [0.0435] 0.0202, 0.0216 [0.0209]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 20 of 26

TABLE C.3.2 Residue Data for Triazole Metabolites from Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
T TA TAA

Elko, SC; 2010 (E11-9082) 2 Horizon 270 Forage 0.2217 7 ND, <0.01 [<0.01] 0.0260, 0.0304 [0.0282] <0.01, <0.01 [<0.01] 14 <0.01, <0.01 [<0.01] 0.0408, 0.0459 [0.0434] <0.01, <0.01 [<0.01] Hay 7 ND, ND [<0.01] <0.1, <0.1 [<0.1] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] <0.1, <0.1 [<0.1] <0.01, <0.01 [<0.01] Grain 0.2219 44 ND, ND [<0.01] 0.114, 0.122 [0.118] 0.0280, 0.0300 [0.0290] Straw 44 <0.01, <0.01 [<0.01] 0.0170, 0.0151 [0.0161] 0.0166, 0.0163 [0.0165] Northwood, ND; 2009 (C13-9083) 5 Jerry Forage 0.2230 7 ND, ND [<0.01] 0.0252, 0.0265 [0.0259] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0250, 0.0288 [0.0269] <0.01, <0.01 [<0.01] Hay 7 ND, ND [<0.01] <0.1, <0.1 [<0.1] 0.0186, 0.0150 [0.0168] 14 <0.01, ND [<0.01] <0.1, <0.1 [<0.1] 0.0255, 0.0223 [0.0239] Grain 0.2213 33 ND, ND [<0.01] 0.128, 0.121 [0.125] 0.0325, 0.0309 [0.0317]
Straw 33 ND, ND [<0.01] <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01]
Geneva, MN; 2009 (C09-9084) 5 Morton Forage 0.2248 7 ND, ND [<0.01] 0.0286, 0.0274 [0.0280] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0446, 0.0505 [0.0476] <0.01, <0.01 [<0.01] Hay 7 ND, ND [<0.01] <0.1, <0.1 [<0.1] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.164, 0.154 [0.159] 0.0108, <0.01 [<0.0104] Grain 0.2225 48 ND, ND [<0.01] 0.0960, 0.0965 [0.0963] 0.0263, 0.0266 [0.0265] Straw 48 <0.01, <0.01 [<0.01] 0.0345, 0.0350 [0.0348] <0.01, <0.01 [<0.01]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 21 of 26

TABLE C.3.2 Residue Data for Triazole Metabolites from Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
T TA TAA

Bagley, IA; 2009 (C30-9085) 5 Reeves Forage 0.2156 7 <0.01, <0.01 [<0.01] 0.0460, 0.0555 [0.0508] <0.01, <0.01 [<0.01] 14 <0.01, <0.01 [<0.01] 0.0670, 0.0665 [0.0668] 0.0126, 0.0107 [0.0117] Hay 7 <0.01, <0.01 [<0.01] 0.121, <0.1 [<0.111] <0.01, <0.01 [<0.01] 14 <0.01, <0.01 [<0.01] 0.176, 0.193 [0.185] 0.0391, 0.0432 [0.0412] Grain 0.2188 32 <0.01, <0.01 [<0.01] 0.344, 0.362 [0.353] 0.112, 0.117 [0.115] Straw 32 ND, <0.01 [<0.01] 0.0104, 0.0220 [0.0162] <0.01, 0.0105 [<0.0103] Ayr, ND; 2009 and Gardner, ND; 2009 (C12- 9086 and C12- 9087) Target PHI 5 Morton Forage 0.2253- 0.2259 7 ND, ND, ND [<0.01] 0.0196, 0.0254, 0.0570 [0.0340] <0.01, <0.01, 0.0220 [<0.0140]

14 ND, ND, ND, ND [<0.01] 0.0272, 0.0257, 0.0440, 0.0462 [0.0358] 0.0128, 0.0109, 0.0396, 0.0432 [0.0266]

Hay 7 <0.01, <0.01, <0.01 [<0.01] 0.106, 0.124, 0.184 [0.138] 0.0162, 0.0166, 0.0374 [0.0234]
14 ND, ND, <0.01, ND

[<0.01] <0.1, <0.1, 0.143, 0.151

[<0.124] 0.0161, 0.0216, 0.0440, 0.0458 [0.0319]
Grain 0.2232- 0.2284 44 ND, <0.01, <0.01, <0.01 [<0.01] 0.0720, 0.0815, 0.134, 0.142 [0.107] <0.02, <0.02, 0.0454, 0.0472

[<0.0332] 25

Straw 44 <0.01, <0.01, ND, <0.01

[<0.01] 0.0236, 0.0176, 0.0132, 0.0112 [0.0164] 0.0216, 0.0122, 0.0196, 0.0232 [0.0192] 25

Gardner, ND; 2009 (C12-9087) Additional Decline PHIs 5 Morton Forage 0.2259 0 ND 0.0575 <0.01
3 ND 0.0565 0.0141
21 ND 0.0435 0.0218 Hay 5 <0.01 0.186 0.0332
21 <0.01 <0.1 0.0248
Grain 0.2284 11 ND 0.140 0.0419
18 <0.01 0.161 0.0468
32 <0.01 0.145 0.0472
Straw 11 ND <0.01 <0.01
18 <0.01 <0.01 <0.01
32 <0.01 <0.01 0.0220Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 22 of 26

TABLE C.3.2 Residue Data for Triazole Metabolites from Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
T TA TAA

Northwood, ND; 2009 (C13-9088) 5 Jerry Forage 0.2205 7 ND, ND [<0.01] 0.0468, 0.0474 [0.0471] 0.0344, 0.0312 [0.0328] 14 ND, ND [<0.01] 0.0247, 0.0286 [0.0267] 0.0188, 0.0186 [0.0187] Hay 7 <0.01, <0.01 [<0.01] 0.179, 0.164 [0.172] 0.0645, 0.0620 [0.0633] 14 <0.01, <0.01 [<0.01] <0.1, <0.1 [<0.1] 0.0309, 0.0326 [0.0318] Grain 0.2216 28 <0.01, <0.01 [<0.01] 0.360, 0.343 [0.352] 0.0985, 0.106 [0.102] Straw 28 ND, ND [<0.01] 0.0165, 0.0138 [0.0152] 0.0261, 0.0232 [0.0247] Uvalde, TX; 2010 (W07- 9089) 6 BOB Forage 0.2269 7 <0.01, <0.01 [<0.01] 0.0270, 0.0272 [0.0271] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0250, 0.0308 [0.0279] <0.01, <0.01 [<0.01] Hay 7 <0.01, <0.01 [<0.01] <0.1, <0.1 [<0.1] <0.01, <0.01 [<0.01] 14 ND, <0.01 [<0.01] <0.1, <0.1 [<0.1] <0.01, <0.01 [<0.01] Grain 0.2250 35 <0.01, <0.01 [<0.01] 0.048, 0.0515 [0.0498] <0.02, <0.02 [<0.02] Straw 35 <0.01, <0.01 [<0.01] 0.0172, 0.0160 [0.0166] 0.0154, 0.0120 [0.0137] White Lake, SD; 2009 (C16-9090) 7 Stallion Forage 0.2255 7 ND, ND [<0.01] 0.0242, 0.0226 [0.0234] <0.01, <0.01 [<0.01] 14 <0.01, <0.01 [<0.01] 0.0570, 0.0476 [0.0523] 0.0108, 0.0111 [0.0110] Hay 7 <0.01, <0.01 [<0.01] 0.100, <0.1 [<0.1] 0.0136, 0.0142 [0.0139] 14 <0.01, <0.01 [<0.01] <0.1, 0.105 [<0.103] 0.0256, 0.0302 [0.0279] Grain 0.2248 36 <0.01, <0.01 [<0.01] 0.212, 0.117 [0.165] 0.0520, 0.0294 [0.0407] Straw 36 ND, <0.01 [<0.01] <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] Carrington, ND; 2009 (C13-9091) 7 Jerry Forage 0.2244 7 ND, ND [<0.01] 0.0190, 0.0178 [0.0184] 0.0106, 0.0102 [0.0104] 14 ND, ND [<0.01] 0.0189, 0.0282 [0.0236] 0.0106, 0.0130 [0.0118] Hay 7 ND, ND [<0.01] <0.1, <0.1 [<0.1] 0.0165, 0.0152 [0.0159] 14 ND, ND [<0.01] <0.1, <0.1 [<0.1] 0.0128, 0.0173 [0.0151] Grain 0.2201 39 <0.01, <0.01 [<0.01] 0.120, 0.204 [0.162] 0.0312, 0.0477 [0.0395] Straw 39 <0.01, <0.01 [<0.01] 0.0102, <0.01 [<0.0101] 0.0174, 0.0164 [0.0169]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 23 of 26

TABLE C.3.2 Residue Data for Triazole Metabolites from Oat Field Trials with Propiconazole.
Trial ID (City, State; Year) 1 Zone Oat Variety Commodity Total Rate 2 (lb ai/A) PHI 3 (days) Residues (ppm) 4 [Average]
T TA TAA

Ault, CO; 2009 (W12-9092) 8 Jerry Forage 0.2273 7 ND, ND [<0.01] 0.0515, 0.0580 [0.0548] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0497, 0.0436 [0.0467] 0.0186, 0.0194 [0.0190] Hay 7 <0.01, ND [<0.01] 0.119, 0.123 [0.121] 0.0144, 0.0146 [0.0145] 14 <0.01, <0.01 [<0.01] <0.1, <0.1 [<0.1] 0.0230, 0.0186 [0.0208] Grain 0.2252 28 ND, ND [<0.01] 0.0625, 0.0625 [0.0625] 0.0208, 0.0214 [0.0211] Straw 28 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01]

1 HED has concluded that trials C12-9086 and C12-9087 constitute a single trial with replicate samples for purposes of 860.1500 data requirements.
2 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
3 For the decline trial the target PHIs are bolded

. 4 The LOQs (determined as the LLMVs) were: 0.01 ppm for T in al l matrices, 0.01 ppm for TA in oat forage and straw, 0.1 ppm in oat hay, and 0.04 ppm in oat grain, and 0.01 ppm for TAA in oa t forage, hay, and straw and 0.02 ppm in oat grain. Per trial averages were calculated by the study reviewer using the LOQ for values reported as <LOQ.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 24 of 26

TABLE C.4. Summary of Residue Data from Oa t Crop Field Trials with Propiconazole. Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Oat Forage Propiconazole 0.2156- 0.2290 7 11 0.135 1.26 0.154 1.17 0.818 0.689 0.379 Propiconazole and Metabolites 11 0.431 2.46 0.499 2.31 1.48 1.40 0.584

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 0.0178 0.146 0.0184 0.128 0.0282 0.0423 0.0308
TAA 11 <0.01 0.0344 <0.01 0.0328 0.0100 0.0126 0.007 Propiconazole 14 11 0.0316 0.480 0.0404 0.449 0.262 0.240 0.150 Propiconazole and Metabolites 11 0.303 1.51 0.389 1.39 0.975 0.919 0.378

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 0.0189 0.212 0.0236 0.212 0.0434 0.0554 0.0536
TAA 11 <0.01 0.0433 <0.01 0.0431 0.0117 0.0165 0.0103 Oat Hay Propiconazole 0.2156- 0.2290 7 11 0.110 4.46 0.184 4.26 1.38 1.66 1.34 Propiconazole and Metabolites 11 0.629 8.54 0.798 8.00 3.23 3.47 2.31

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 <0.1 0.334 <0.1 0.325 0.100 0.133 0.0675
TAA 11 <0.01 0.0645 <0.01 0.0633 0.0145 0.0201 0.0160 Propiconazole 14 11 0.0620 2.69 0.0680 1.98 0.540 0.677 0.571 Propiconazole and Metabolites 11 0.559 5.69 0.592 4.41 1.99 2.30 1.25

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 <0.1 0.387 <0.1 0.373 0.100 0.140 0.0824
TAA 11 <0.01 0.110 <0.01 0.107 0.0239 0.0300 0.0276 Oat Grain Propiconazole 0.2188- 0.2331 25-48 11 <0.01 0.386 <0.01 0.368 0.0392 0.100 0.121 Propiconazole and Metabolites 11 0.0630 1.61 0.0649 1.56 0.195 0.440 0.549

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 0.0480 0.362 0.0498 0.353 0.125 0.169 0.108
TAA 11 <0.02 0.117 <0.02 0.115 0.0332 0.0476 0.0326 Oat Straw Propiconazole 25-48 11 0.0172 2.40 0.0191 1.21 0.0894 0.309 0.383 Propiconazole and Metabolites 11 0.291 6.07 0.302 5.10 2.05 2.22 1.45

T 11 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 11 <0.01 0.0438 <0.01 0.0435 0.0161 0.0181 0.0110
TAA 11 <0.01 0.0261 <0.01 0.0247 0.0137 0.0147 0.0052

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used fo r any results reported as <LOQ in Tables C.3.1. and C.3.2 N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.



### D. CONCLUSION

The submitted oats field trial data are adequate. Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propic onazole at 0.2156-0.2290 lb ai/A, residues (and perPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 25 of 26 

### trial averages of propiconazole) per se and propiconazole and metabolites determined as 2,4- DCBA, respectively, in/on forage were: 0.135-1.26 (0.154-1.17) a nd 0.431-2.46 (0.499-2.31) ppm at the 7-day PHI; and 0.0316-0.480 (0.0404- 0.449) and 0.303-1.51 (0.389-1.39) ppm at the 14-day PHI; corresponding residues in/on hay were: 0.110-4.46 (0.184-4.26) and 0.629-8.54 (0.798-8.00) ppm at the 7-day PHI; a nd 0.0620-2.69 (0.0680-1.98) and 0.559-5.69 (0.592-4.41) ppm at the 14-day PHI. In/on grain and stra w harvested at PHIs of 25-48 days following two applications at 0.2188-0.2331 lb ai /A, corresponding residues (and per trial averages) were: <0.01-0.386 (<0.01-0.368) and 0.0630-1.61 (0.06 49-1.56) ppm in/on grain, and 0.0172-2.40 (0.0191-1.21) and 0.291-6.07 (0.302-5.10) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of oat forage, hay, grain, and straw. Residues (and per trial averages) of TA and TAA, respectively, in/on forage were 0.0178-0.146 (0.0184-0.128) and <0.01-0.0344 (<0.01-0.0328) ppm at the 7- day PHI; and 0.0189-0.212 (0.0236-0.212) and < 0.01-0.0433 (<0.01-0.0431) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on hay were <0.1-0.334 (<0.1-0.325) and <0.01-0.0645 (<0.01-0.0633) ppm at the 7-day PHI; and <0.1-0.387 (<0.1- 0.373) and <0.01-0.110 (<0.01-0.107) ppm at the 14-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on gr ain and straw were: 0.0480-0.362 (0.0498-0.353) and <0.02-0.117 (<0.02-0.115) ppm in/on grain; and <0.01-0.0438 (<0.01-0.0435) and <0.01-0.0261 (<0.01-0.0247) ppm in/on straw.

The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA generally decr eased with increasing PHI in/on oat forage and hay. Residues of propiconazole per se and propiconazole and metabolites determined as 2,4- DCBA in/on grain and straw generally increase d with increasing PHI. For the triazole metabolites, residues of T were below the LOQ in/on all matrices at all sampling intervals; therefore, residue decline coul d not be assessed. Residues of TA in/on forage generally decreased with increasing PHI; residues of TAA generally increased with increasing PHI. Residues of TA and TAA generally decreased with increasing PHI in/on ha y; residues of TA and TAA were variable in/on grain but increased sligh tly from the initial to the final PHI. Residues of TA were below the LOQ at all sampling interv als in/on straw; therefor e, residue decline was not assessed. Residues of TAA in/on straw we re below the LOQ through the 18-day PHI, but increased to 0.022 ppm at the 32-day PHI.

Acceptable methods were used for residue qua ntitation, and the study is supported by adequate storage stability data.

E. REFERENCES

DP# 210742, 3/15/95, M. Rodriguez. DP# 240856, 2/23/05, T. Morton. DP# 388246, 5/28/08, M. Doherty. DP# 363016, 1/12/12, D. Drew; 47606601.der.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Oats

DP# 400030/MRID No. 48681703 Page 26 of 26 

### F. DOCUMENT TRACKING

RDI: T. Morton(2/27/2013); S. Hummel (2/27/2013) Petition Number: 2F7975 DP Barcode(s): 400030 PC Code: 122101

Template Version June 2005.**~** Prop!conazol e/ PC Code 12210**Syngent~** Cr op Prot ect ion

, LL C



### = 

# I DACO 7.4.1/7.4.2 /0P PTS 8 60. 1 500/0ECD IIA 6.3.1, 6.3.2
, 6.3.3 and Ili A 8.3.1
, 8

. 3.2. 8 .3.3 Cro p Fiel d Tria l/ 

### R esidue Deer

- Whe at



### Primary Eva luator

Approved by Thiir ston G

. o iton

, Che mist**~(7 509P** **)**

# v.**~** Susan V. Hwnmel, Senior Scientist H EDIRA B IV (7509 P ) Da te: 2/2 7 / 1 3

Da te: 2 / 27/13

Note : This DER was originally p repared under co n tract by Vers ar , In c

. (68 50 Ver s ar Cent er , Sp ringfi e ld

, VA 22 1 51; s ubmitt ed 6 /2 7/12). The DER has been reviewed by the Health Effects Di v i sio n ( HED ) and re vi sed to reflect current Office of Pesticid e Progra ms (OPP) polici es.



### STUDY REPORTS:

48681704 Hampton, M

. (20 11) A zox ystrobin / Propi co nazol e SE (A 1590 9C)

- Magni tude of the Residue s i n o r on Wheat: Final R e p o rt

. P rojec t Number: TK 000 3 213, T0044 0 7/08. Unpublished study prepar ed by Syngenta C rop P rotect ion

, D r a g on Run Ag Serv i ces , In c. and Pest Management E nterpri se s, In c. 1167 p.

EXECUTIVE SUMMARY:

Syngenta Crop Protecti on, LLC

. has s ubmitt ed field t rial data for propiconazole on wheat. Fifteen field tri als were co nduct ed in th e U nited States dur ing t h e 2008

- 2010 growing seasons in the North American Fr ee Trade Agreement (NA FTA ) Growing Zones 2 (V A; 1 trial ), 4 (LA; 1 trial), 5 (N D and l A; 3 tr ial s), 6 ( TX; 1 tr ial), 7 (SD and ND; 4 trial s), 8 ( TX and CO ; 4 trial s), and 11 (ID; l tri a l). Th e submission als o include s data for azoxystrobin. Refer to 4 8 681704.d e l fo r data pertaining to azoxy strob in.

Three trial pair s or sets ( trials C13-9033
, Cl3-9038, and C13-90 40
, trial s C1 6-9 037 a n d C16- 9039
, and trial s W39- 90 42 and W39-904 3) were e ach conducted by the same prin cipa l field i nv estiga tor ( P FI). All tr ials reflected use of different tank mixe s fo r all appli cati o n s. Tri a l Cl3- 9033 was conducted in a differ en t NA F TA Zone ; thus, HED concludes t h at this trial ma y be counted as a separate tr ia l for purpose s of 860.1500 data r e quirem e nts. Exam inat io n of th e field trial records indicates that there w e re sufficient differenc es in the p ar amet e rs for eac h rem a ining pair of trials, in cludin g differences in wheat varie ty, dat es of in i t ial ap plica t i on (>30 da ys; trial s Cl3-9038 and C 13 -9040 and trials C1 6-9 037 and Cl6- 903 9 only ), adjuvant use (CO C v s N IS ; tria ls C16-90 37 and C16- 9 039 only)

, > 20

- mile sep ara t i o n in trial l oc ati on ( trials W39-9042 and W3 9-9 043 only), irri gat ion u se (furrow vs non e; t r ials W39-9042 and W39-9043 on l y), and a >25 % difference in s pr ay v o lume (-20 ga l/A vs

. 2 gal/A ; tr ials C 13-9038 and C13-9040 only)

, tha t eac h trial constitutes a separ a te trial for purp oses of 860.1500 data requirements.

Each tr ial consis ted of o ne untreated plot and one or two treated plots; se parate plots we re

es tablished for th e harvest of forage and hay and for the harvest o f grain an d straw. At each trial loc a tion, th e treated plots received tw o foliar bro adca st a pplicat io ns o f a multi ple active ingre dien t ( MAl) suspo- emul s ion ( S E) formulation (Quilt XcelTM) cont ai ning 1

. 18 lb ai /g al

DP# 400030 / MRID No

. 48681704 Page I of31Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 2 of 31 

### azoxystrobin and 1.02 lb ai/gal propiconazole. A pplications were target ed at Feekes growth stage 5, and 7 days prior to harves t for the forage and hay plots, and at 14 days prior to Feekes 10.54, and Feekes 10.54 for grain and straw plots. Only data pertaining to propiconazole are reviewed in this DER; therefore, the product will be referred to herein as the 1.02 lb ai/gal SE formulation. Each treated plot received two applications of propiconazole at 0.1033-0.1174 lb ai/A/application, for a to tal seasonal rate of 0.214 0-0.2308 lb ai/A. Applications were made at 13- to 16-day retreatment intervals (RTIs) using ground equipment in spray volumes of 2.00- 24.16 gal/A; applications were made at a 7-day RTI to treated plot 3 (grain and straw) at the C12-9035 trial site. A nonionic surfactant (NIS) was added to the spray mixtures for all applications in eleven trials, and a crop oil con centrate (COC) was added to the spray mixtures in four trials. Samples of forage and hay were harv ested from all trials (with the exception of trial C12-9035) at preharvest intervals (PHIs) of 7 and 14-20 days; grai n and straw were harvested at maturity (PHIs of 24-64 days). Additional forage and hay samples were harvested at PHIs of 0, 3, 7, and 21 days from two trials (in IA and TX) to assess residue decline; additional grain and straw samples were collected 14 and 7 days prior to, and 7 days after, maturity. Hay samples were dried to approximately 10-20% moisture content; drying interv als were not reported.

Application rates in the submission were reporte d in terms of total lb ai/A for combined application of azoxystrobin a nd propiconazole (refer to pg. 12 of MRID 48681704). Individual application rates for azoxystrobi n and propiconazole were calcul ated by the study reviewer based on the ratio of the active ingr edients in the product: 1.18/ 2.2 for azoxystrobin or 1.02/2.2 for propiconazole.

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a high performance liquid chromatography met hod with tandem mass spectrometry detection (LC/MS/MS), Morse Laboratories Meth-180. The lim it of quantitation (LOQ; determined as the lowest limit of method validation; LLMV) was 0.01 ppm. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas chromatography with mass select ive detection (GC/MSD), Nova rtis Crop Protection method AG-626. This is a common moiety method in wh ich all residues of c oncern are converted by base hydrolysis and oxidation to 2,4-DCBA, then de termined as the 2,4-DCBA methyl ester, and reported in propiconazole equivalents. The LOQ (determined as the LLMV) was 0.05 ppm. Samples were analyzed for the triazole metabolit es 1,2,4-triazole (T), tria zole alanine (TA), and triazole acetic acid (TAA) using LC/MS/MS, Morse Laboratories Meth-160, Revision #2. The LOQs (determined as the LLMVs) were: 0.01 pp m for T and TAA in all matrices and 0.01 ppm for TA in forage, hay, and stra w and 0.02 ppm in grain. The met hods were adequate for data collection based on acceptable method validation and concurrent recovery da ta. The fortification levels used in concurrent method recovery were adequate to bracket expe cted residue levels. Method validation and concurrent recoveries were corrected for apparent residues in controls; treated samples were not correct ed for residues in controls.

Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samp les were stored frozen (<-10 °C at the preparation facility and <-20 °C at the analytical laboratory) from collection to analysisPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 3 of 31 

### for propiconazole and propiconazole and meta bolites, respectively, for 51-348 days (1.7-11.4 months) and 51-363 days (1.7-11.9 months) for fo rage, 51-358 days (1.7-11.8 months) and 70- 372 days (2.3-12.2 months) for hay, 45-313 days (1.5-10.3 months) and 87-348 days (2.9-11.4 months) for grain, and 49-318 days (1.6-10.5 mo nths) and 125-378 days (4.1-12.4 months) for straw. Sample storage durations prior to analys is for the triazole metabolites were 39-546 days (1.3-18.0 months) for forage, 43-339 days ( 1.4-11.2 months) for hay, 48-313 days (1.6-10.3 months) for grain, and 43-312 days (1.4-10.3 months ) for straw. All samples were analyzed within 0-20 days of extraction. Adequate storag e stability data are av ailable to support the storage durations and conditions of samples from the submitted fiel d trials. The data indicated that corrections for decline on storage in forage samples were needed for residues of T in the 7- day samples from trial C30-9034; however, no corrections were made because all residues were ND at all decline intervals.

Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propiconazole at 0.2190-0.2306 lb ai/A, residues (and per trial averages) of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respectively, in/ on forage were: 0.271- 4.90 (0.271-4.79) and 1.18-9.00 (1.23-8.47) ppm at the 7-day PHI; and 0.0606-2.16 (0.0813- 2.13) and 0.717-5.85 (0.778-5.46) ppm at the 14- to 20-day PHI; corresponding residues in/on hay were: 0.444-9.82 (0.444-9.57) and 1.98-22.5 ( 1.98-21.6) ppm at the 7-day PHI; and 0.149- 5.48 (0.156-5.41) and 1.57-18.7 (1.62-17.4) ppm at the 14 - to 20-day PHI. In/on grain and straw harvested at PHIs of 24-64 days followi ng two applications at 0.2140-0.2308 lb ai/A, corresponding residues (and pe r trial averages) were: <0.01-0.0842 (<0.01-0.0779) and <0.05- 0.169 (<0.05-0.145) ppm in/on grain, a nd 0.0432-4.36 (0.0462-4.04) and 0.570-13.3 (0.597- 12.6) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of wheat forage, hay, grain, and straw. Residues (and per tria l averages) of TA and TAA, respectively, in/on forage were < 0.01-0.0975 (<0.0110-0.0918) and <0.01-0.0336 (<0.01-0.0324) ppm at the 7-day PHI; and <0.01-0.0740 (<0.01-0.0735) and <0.01-0.0444 (<0.01-0.0442) ppm at the 14- to 20-day PHI. Residues (and per tria l averages) of TA and TAA, respectively, in/on hay were 0.0218-0.250 (0.0218-0.236) and <0.01-0.138 (<0.01-0.135) ppm at the 7-day PHI; and 0.0158-0.174 (0.0166-0.166) and <0.01-0.128 (<0.0125-0.116) ppm at the 14- to 20-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.02-0.286 (<0.02-0.279) and <0.01-0.0720 (<0.01- 0.0718) ppm in/on grai n; and <0.01-0.0560 (<0.01-0.0515) and <0.01-0.0510 (<0.01-0.0497) ppm in/on straw.

The residue decline results were variable for all crop matrices. The residu e decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4- DCBA generally decreased with increasing PHI in /on wheat forage and hay at both the IA and TX decline trials. Residues of propiconazole per se in/on straw at the IA trial were variable; residues increased from the 25-day PHI to the highest at the 32-day PHI, and then decreased at the 39- and 46-day PHI. Residues of propicona zole and metabolites determined as 2,4-DCBA increased with increasing PHI in/on wheat straw at the IA trial. Re sidues of propiconazole per

se and propiconazole and metabolites determin ed as 2,4-DCBA generally decreased withPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 4 of 31 

### increasing PHI in/on wheat straw at the TX trial. Residues of propiconazole per se in/on grain were below the LOQ at all sampling intervals at th e IA trial; therefore, re sidue decline could not be assessed. At the TX tria l, residues of propiconazole per se generally decreased with increasing PHI. Residues of propiconazole and metabolites determined as 2,4-DCBA were fairly constant in/on wheat grain at each sampling interval at both the IA and TX decline trials. For the triazole metabolites, residues of T were belo w the LOQ in/on all matrices at all sampling intervals; therefore, residue declin e could not be assessed for either de cline trial. At the IA trial, residues of TA generally increased with incr easing PHI in/on forage and straw, generally decreased with increasing PHI in /on hay, and remained relatively constant in/on grain. At the TX trial, residues of TA genera lly decreased with increasing PHI in/on forage and hay and were below the LOQ at all sampling intervals in/on grai n and straw; therefore, residue decline was not assessed. At the IA trial, residues of TAA gene rally decreased with increasing PHI in/on forage and hay, generally increased with increasing PHI in/on straw, and remained relatively constant in/on grain. At the TX trial, residues of TAA remained relativ ely constant in/on hay and were below the LOQ at all sampling intervals in/on fora ge, grain, and straw; ther efore, residue decline was not assessed.

STUDY/WAIVER ACCEPTABILITY/ DEFICIENCIES/CLARIFICATIONS :
Under the conditions and parameters used in the study, the field tria l residue data are classified as scientifically acceptable. The acceptability of this study fo r regulatory purposes is addressed in the forthcoming U.S. EPA Residue Chemistry Summary Document [DP# 400030].

COMPLIANCE :
Signed and dated Good Laboratory Practice (GLP), Quality Assurance, a nd Data Confidentiality statements were provided. No deviations fr om regulatory requirement s were reported which would have an impact on the validity of the study.

A. BACKGROUND INFORMATION

Propiconazole is a triazole-type fungicide that provides broad spectrum disease control through inhibition of sterol biosynthesis in fungi. It is registered to Syngenta Crop Protection for the control of fungal diseases on a variety of crops.

The nomenclature of propiconazole , 1,2,4-triazole (T), triazole al anine (TA), and triazole acetic acid (TAA) are summarized in Table A.1, and th e physicochemical properties of propiconazole are summarized in Table A.2.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 5 of 31

TABLE A.1. Nomenclature of Propiconazole and Triazoles. Compound

Common name Propiconazole Company experimental names CGA-64250 IUPAC name 1-[2-(2,4_dichlorophenyl)-4-propyl- 1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole CAS name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1, 3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole
CAS # 60207-90-1

End-use products/EP Suspo-emulsion (SE) formulation (Quilt XcelTM) containing 1. 18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole Compound

Common name 2,4-DCBA Chemical name 2,4-dichlorobenzoic acid Compound

Common name 1,2,4-Triazole (T)
Chemical name 1 H -1,2,4-triazole CAS registry number 288-88-0 Compound

Common name Triazole alanine or triazolylalanine (TA)
Chemical name α -amino-1 H -1,2,4-triazole-1-propanoic acid CAS registry number 114419-45-3 Compound

Common name Triazole acetic acid or triazolylacetic acid (TAA)
Chemical name 1 H -1,2,4-triazole-1-acetic acid CAS registry number 28711-29-7 N N N

O O
Cl Cl

N H N

N

N N N

O H NH 2

O

N N N

O H OPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 6 of 31

TABLE A.2. Physicochemical Properties of Technical Grade Propiconazole.
Parameter Value Reference Boiling point 120°C at 1.9 Pa, >250°C at 101.325 kPa MRID No.:43698701 pH 4.9 @ 25°C (1% aqueous dispersion) MRID No.:43698701 Density 1.289 g/cm3 typical @ 20°C MRID No.: 43698701 Water solubility (20°C) 0.10 g/L at 20°C MRID No.: 41720301

Solvent solubility (temperature not specified) Completely miscible in ethanol, acetone, toluene and n-octanol. n-hexane = 47 g/L MRID No.: 42030201 Vapor pressure at 25°C 4.2 x 10 -7 mm Hg @ 25°C MRID No.: 41720301 Dissociation constant (pK a ) 1.09 MRID No.: 43698701 Octanol/water partition coefficient Log(K OW ) (25 °C) 3.72 @ pH 6.6 MRID No.: 43698701 UV/visible absorption spectrum ( 8 max, nm) Not available MRID No.: 40583703



### B. EXPERIMENTAL DESIGN

B.1. Study Site Information

Fifteen field trials we re conducted in the United States du ring the 2008-2010 growing seasons in the NAFTA Growing Zones 2 (VA; 1 trial), 4 (LA; 1 trial), 5 (ND and IA; 3 trials), 6 (TX; 1 trial), 7 (SD and ND; 4 trials), 8 (TX a nd CO; 4 trials), and 11 (ID; 1 trial).

Three trial pairs or sets (trials C13-9 033, C13-9038, and C13-9040, trials C16-9037 and C16- 9039, and trials W39-9042 and W39-9043) were each conducted by the same principal field investigator (PFI). All trials reflected use of different tank mixes for all applications. Trial C13- 9033 was conducted in a different NAFTA Zone; t hus, HED concludes that this trial may be counted as a separate trial for purposes of 860.1500 data requirements. Examination of the field trial records indicates that there were sufficient differences in the parameters for each remaining pair of trials, including differences in wheat vari ety, dates of initial application (>30 days; trials C13-9038 and C13-9040 and trials C16-9037 and C 16-9039 only), adjuvant use (COC vs NIS; trials C16-9037 and C16-9039 only), >20-mile se paration in trial location (trials W39-9042 and W39-9043 only), irrigation use (furrow vs none ; trials W39-9042 and W39-9043 only), and a >25% difference in spray volume (~20 gal/A vs. 2 gal/A; trials C13-9038 and C13-9040 only), that each trial constitutes a separate tr ial for purposes of 860.1500 data requirements.

Each trial consisted of one untre ated plot and one or two treate d plots; separate plots were established for the harvest of forage and hay and fo r the harvest of grain and straw. At each trial location, the treated plots received two foliar br oadcast applications of a 1.02 lb ai/gal SE formulation of propiconazole (Qui lt XcelTM). Applications were ta rgeted at Feekes growth stage 5, and 7 days prior to harvest fo r the forage and hay plots, and at 14 days prior to Feekes 10.54, and Feekes 10.54 for grain and straw plots. Each treated plot received two applications of propiconazole at 0.1033-0.1174 lb ai/A/application, for a total seasonal rate of 0.2140-0.2308 lb ai/A. Applications were made at 13- to 16- day RTIs using ground equipment in spray volumes of 2.00-24.16 gal/A; applications were made at a 7-da y RTI to treated plot 3 (grain and straw) atPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 7 of 31 

### the C12-9035 trial site. An NIS was added to the spray mixtures for all applications in eleven trials, and a COC was added to the spray mixtures in four trials. Samples of forage and hay were harvested from all trials (with the exception of trial C12-9035) at PHIs of 7 and 14-20 days; grain and straw were harvested at maturity (PHIs of 24-64 days). Additional forage and hay samples were harvested at PHIs of 0, 3, 7, and 21 da ys from two trials (in IA and TX) to assess residue decline; additional grai n and straw samples were collected 14 and 7 days prior to, and 7 days after, maturity. Hay samples were dried to approximately 10-20% moisture content; drying intervals were not reported.

Maintenance pesticides and fertilizers were us ed as needed to produce a commercial quality crop. Monthly temperature ranges and total monthly precipitation were provided for each trial, as well as the historical averag es. Irrigation was used to supplement rainfall as needed. The petitioner stated that actual te mperature recordings were within average historical values, and actual average rainfall was within historical rainfall averages. In trial E07-9031 (VA), the second application to treated plot 3 (grain and straw) was made at medium milk (vs. 10.54). In trial E17-9032 (LA), the second appl ication to treated plot 3 (grain and straw) was made at early milk (vs. 10.54). In trial C12-9035 (ND), the sec ond application to treated plot 3 was made at the middle of heading (vs. watery ripe kernel) because the crop did not mature as quickly as expected. In trial C13-9038 (ND), the second app lication to treated plot 3 was made at the end of flowering due to delayed maturation caused by the weather. In Trial C16-9039, the second application to treated plot 3 (gra in and straw) occurred at full fl owering to the end of flowering due to delayed maturation caused by the weat her. In Trials W 39-9042 and W39-9043 (TX), wind was 6-7 mph during both applications of tr eatment 2 (forage and hay). In Trial W12-9044 (CO), the first application to treat ed plot 2 (forage and hay) occu rred at Feekes Growth Stage 9 (vs 5). Although variations in temperature a nd precipitation were repor ted, no abnormal weather events were indicated to have adversely impacted crop yields or crop growth and development at the remaining trial sites.

Trial conditions are presented in Table B.1.1. Th e study use pattern is presented in Table B.1.2, and the crop varieties grown are identified in Table C.3.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

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TABLE B.1.1 Trial Site Conditions

. Trial Identification: City, State; Year (Trial No.) Soil characteristics Type %OM pH CEC (meq/100 g) Suffolk, VA; 2009 (E07-9031) Sandy loam 1.5 5.7 3.0 Cheneyville, LA; 2009 (E17-9032) Silt loam 0.80 7.7 12 Northwood, ND; 2009 (C13-9033) Loam 4.7 6.9 19.8 Bagley, IA; 2009 (C30-9034) Clay loam 3.4 7.2 26 Gardner, ND; 2009 (C12-9035) 1 Clay loam 3.2 7.6 29.8 Raymondville, TX; 2009 (W08-9036) Sa ndy clay loam 1.1 8.1 30.2 Lake Andes, SD; 2009 (C16-9037) Clay loam 3.1 7.6 37.9 Carrington, ND; 2009 (C13-9038) Sandy loam 2.7 6.9 24.0 Lake Andes, SD; 2009 (C16-9039) Loam 3.6 6.1 21.8 Carrington, ND; 2009 (C13-9040) Loam 3.9 7.0 27.2 Groom, TX; 2009 (E13-9041) Clay loam 1.2 7.6 27.8 Levelland, TX; 2009 (W39-9042) Sand y clay loam 0.2 7.7 10.0 Littlefield, TX; 2009 (W39- 9043) Loam 0.2 7.2 11.3 Ault, CO; 2008 (W12-9044) Sandy loam 1.5 7.0 31.5 Rupert, ID; 2010 (W15-9046) Loam 1.4 8.2 16.9 Gardner, ND; 2010 (C12-9047) 1 Clay loam 3.2 7.6 29.8

1 Forage and hay samples were not collected in Trial C12-9035. Trial C12-9047 was a dded to generate the required forage and hay samples.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 9 of 31

TABLE B.1.2. Stud y Use Pattern. Location (City, State; Year) Trial ID EP 1 Plot Application Information Tank Mix/ Adjuvants 4 Method; Timing Volume (gal/A) Rate 2 (lb ai/A) RTI 3 (days) Total Rate 2 (lb ai/A) Suffolk, VA; 2009 (E07- 9031) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 11.77 0.1128 -- 0.2260 NIS 2. Foliar broadcast; Feekes 5.2 11.80 0.1131 14

3 [Grain and

Straw] 1. Foliar broadcast; 65 11.69 0.1133 -- 0.2257 NIS 2. Foliar broadcast; 75 12.24 0.1124 14

Cheneyville, LA; 2009 (E17-9032) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 18.89 0.1130 -- 0.2218 NIS 2. Foliar broadcast; Late tillering (prior to boot) 19.04 0.1088 13

3 [Grain and

Straw] 1. Foliar broadcast; 80% headed 5.35 0.1128 -- 0.2237 NIS 2. Foliar broadcast; Early milk 5.93 0.1109 14

Northwood, ND; 2009 (C13-9033) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 30 19.96 0.1108 -- 0.2217 NIS 2. Foliar broadcast; Feekes 8 19.97 0.1109 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 45 19.88 0.1103 -- 0.2215 NIS 2. Foliar broadcast; Feekes 10.54 20.02 0.1111 14

Bagley, IA; 2009 (C30- 9034) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes Stage 5 10.10 0.1033 -- 0.2199 NIS 2. Foliar broadcast; 14 days after Feekes 5 9.55 0.1167 14

3 [Grain and

Straw] 1. Foliar broadcast; 14 days prior to Feekes 10.54 10.43 0.1064 -- 0.2140 NIS

2. Foliar broadcast; Feekes 10.54 7.80 0.1076 14 Gardner, ND; 2009 (C12- 9035) 1.02 lb ai/gal SE 3 [Grain and

Straw] 1. Foliar broadcast; 52 15.66 0.1156 -- 0.2297 NIS 2. Foliar broadcast; 55 15.45 0.1141 7

Raymondville, TX; 2009 (W08-9036) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 29-30: tillering end & begin stem elongation 20.80 0.1160 -- 0.2306 NIS

2. Foliar broadcast; BBCH 31: 1 st node detectable 20.56 0.1147 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 43: flag leaf sheath just visible; mid-boot 20.49 0.1141 -- 0.2270 NIS

2. Foliar broadcast; BBCH 71: kernels watery ripe 20.27 0.1129 14

Lake Andes, SD; 2009 (C16-9037) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 23 23.15 0.1116 -- 0.2244 NIS 2. Foliar broadcast; 55-59 19.10 0.1127 13

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 55-59 19.26 0.1136 -- 0.2247 NIS 2. Foliar broadcast; BBCH 71 20.10 0.1110 15

Carrington, ND; 2009 (C13-9038) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 16 20.16 0.1123 -- 0.2246 COC 2. Foliar broadcast; BBCH 55 20.14 0.1122 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 37 20.12 0.1114 -- 0.2228 COC 2. Foliar broadcast; BBCH 69 19.98 0.1114 14Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 10 of 31

TABLE B.1.2. Stud y Use Pattern. Location (City, State; Year) Trial ID EP 1 Plot Application Information Tank Mix/ Adjuvants 4 Method; Timing Volume (gal/A) Rate 2 (lb ai/A) RTI 3 (days) Total Rate 2 (lb ai/A) Lake Andes, SD; 2009 (C16-9039) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; 23 19.36 0.1086 -- 0.2190 COC 2. Foliar broadcast; 43 18.11 0.1104 16

3 [Grain and

Straw] 1. Foliar broadcast; 43 17.88 0.1090 -- 0.2196 COC 2. Foliar broadcast; 67-69 18.34 0.1106 16

Carrington, ND; 2009 (C13-9040) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; BBCH 30 2.02 0.1124 -- 0.2236 COC 2. Foliar broadcast; Feekes 8 2.00 0.1112 14

3 [Grain and

Straw] 1. Foliar broadcast; BBCH 45 2.03 0.1128 -- 0.2257 COC 2. Foliar broadcast; BBCH 71 2.03 0.1128 13

Groom, TX; 2009 (E13- 9041) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 12.40 0.1132 -- 0.2240 COC 2. Foliar broadcast; Feekes 6 21.29 0.1108 14

3 [Grain and

Straw] 1. Foliar broadcast; Feekes 10.5.1 23.38 0.1117 -- 0.2243 COC 2. Foliar broadcast; Feekes 10.5.4 24.16 0.1126 14

Levelland, TX; 2009 (W39- 9042) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 19.78 0.1103 -- 0.2219 NIS 2. Foliar broadcast; Joint 20.01 0.1116 14

3 [Grain and

Straw] 1. Foliar broadcast; Heading 20.24 0.1129 -- 0.2286 NIS 2. Foliar broadcast; Watery Ripe 20.75 0.1157 14

Littlefield, TX; 2009 (W39- 9043) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 5 19.85 0.1107 -- 0.2209 NIS 2. Foliar broadcast; Joint 19.76 0.1102 14

3 [Grain and

Straw] 1. Foliar broadcast; Heading 20.90 0.1166 -- 0.2308 NIS 2. Foliar broadcast; Watery Ripe 20.47 0.1142 14

Ault, CO; 2008 (W12- 9044) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; Feekes 9 20.98 0.1116 -- 0.2254 NIS 2. Foliar broadcast; Feekes 10.2 16.73 0.1138 14

3 [Grain and

Straw] 1. Foliar broadcast; Feekes 10.2 16.41 0.1129 -- 0.2240 NIS 2. Foliar broadcast; Feekes 10.54 16.33 0.1110 14

Rupert, ID; 2010 (W15- 9046) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; 30 9.55 0.1114 -- 0.2259 NIS 2. Foliar broadcast; 33 17.12 0.1145 14

3 [Grain and

Straw] 1. Foliar broadcast; 55-59 17.20 0.1111 -- 0.2285 NIS 2. Foliar broadcast; 71 16.68 0.1174 14

Gardner, ND; 2010 (C12- 9047) 1.02 lb ai/gal SE 2 [Forage and Hay] 1. Foliar broadcast; 33 10.06 0.1124 -- 0.2247 NIS 2. Foliar broadcast; 41 20.22 0.1123 13Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 11 of 31 1 EP = End-use Product; a multiple active ingredient (MAI) sus po-emulsion (SE) formulation (Quilt XcelTM) containing 1.18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole.
2 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
3 RTI = Retreatment Interval.
4 NIS = non-ionic surfactant. COC = crop oil concentrate.

TABLE B.1.3. Trial Numbers and Geographical Locations

. NAFTA Growing Regions Wheat Submitted Requested 1

Canada U.S.
1 -- -- --
1A -- -- --
2 1 -- 1/1
3 -- -- --
4 1 -- 1/1
5 3 2 -- 5/3
5A -- -- --
5B -- -- --
6 1 -- 1/1
7 4 -- 5/4
7A -- -- --
8 4 -- 6/4
9 -- -- --
10 -- -- --
11 1 -- 1/1
12 -- -- --
13 -- -- --
14 -- -- --
15 -- -- --
16 -- -- --
17 -- -- --
18 -- -- --
19 -- -- --
20 -- -- --
21 -- -- --
Total 15 2 20/15

1 As per OCSPP 860.1500, Table 5 for wheat. The second number reflects a 25% reductio n in the number of trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application results in no quantifiable residues.
2 Forage and hay samples were not collected in Trial C12-9035. Trial C12-9047 was a dded to generate the required forage and hay samples. The petitioner counted this as 1 trial.


### B.2. Sample Handling and Preparation

Single control and duplicate treated samples of forage (~3 lb) and hay (~2 lb) were harvested at PHIs of 7 and 14-20 days; samples of grain (~3 lb ) and straw (~2 lb) were harvested at maturityPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 12 of 31 

### (24- to 64-day PHIs). Additional forage and ha y samples were harvested at PHIs of 0, 3, 7, and 21 days from two trials to assess residue de cline; additional grain and straw samples were collected at 14 and 7 days prior to, and 7 days after, maturity. Hay samples were dried to approximately 10-20% moisture cont ent; drying intervals were not reported. The samples were placed in frozen storage at the field sites (inter val between collection and freezing not reported). All samples were shipped frozen within 1-115 da ys of collection by freezer truck or overnight courier to the preparatio n facility, Syngenta Crop Protection (G reensboro, NC), where they were maintained frozen (<-10 °C) prior to and following preparation. In preparation for analysis, any adhering soil and inedible portions of wheat we re removed from the samples by light brushing. Samples were homogenized by grinding in a Hobart food cutter in the presence of dry ice. Within 6-299 days of receipt at the preparation facility, samples were shipped frozen via FedEx to the analytical laboratory, Morse Laboratories (Sacramento, CA), where they were maintained frozen (~ -20 °C) prior to analysis.

B.3. Analytical Methodology

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a LC/MS/MS method, Morse Laboratories Meth -180. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas GC/MSD, Novartis Crop Prot ection method AG-626. This is a common moiety method in which all residues of concern are converted by base hydrolysis and oxidation to 2,4-DCBA, then determined as the 2,4-DCBA methyl ester, and re ported in propiconazole equivalents. Samples were analyzed for the triazole metabolites T, TA, and TAA using LC/MS/MS, Morse Laboratories Meth-160, Revision #2.

For determination of residues of propiconazole per se , samples were extracted with methanol:water (80:20, v:v) and filtered. Water and saturated NaCl solution were added to an aliquot of the filtrate, which was then partitioned three times with hexane. The combined hexane extracts were evaporated to dryness, reconstitu ted in acetonitrile:wate r (30:70, v:v), and then analyzed using LC/MS/MS. The LOQ (determined as the LLMV) was 0.01 ppm; the limit of detection (LOD) was not reported.

For determination of residues of propiconazo le and metabolites conve rtible to 2,4-DCBA, samples were refluxed with methanol:ammonium hydroxide (80:20, v:v). An aliquot of the extract was evaporated to dryness. The residues were dissolved in aqueous NaOH and heated in the presence of potassium permanganate for oxidation of propiconazole and metabolites to 2,4- DCBA. The sample was acidified with HCl and pa rtitioned with hexane:eth yl ether (90:10, v:v). The organic phase was evaporated to dryness an d derivatized with diazomethane to form the methyl ester of 2,4-DCBA. The derivatized extract was evaporated to dryness, reconstituted in hexane, and purified using an al umina solid phase extraction (SPE ) cartridge. The sample was reduced to a known volume using nitrogen evaporat ion and then analyzed using GC/MSD. The LOQ (determined as the LLMV) was 0.05 ppm; the LOD was not reported.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 13 of 31 

### For determination of T, TA, and TAA, samples we re extracted with methanol:water (80:20, v:v). Following the addition of Celite, the extracts were vacuum filtered, rinsed, and brought to volume with methanol:water (80:20, v:v). For dete rmination of TAA, an aliquot of the extract were purified by SPE and then derivatized by HC l/butanol esterification. The TA aliquot underwent two derivatizations: an esterificat ion using HCl/butanol and an acylation using heptafluorobutyric anhydride (HFBA). The T al iquot was directly derivatized with dansyl chloride to produce the dansyl derivative of 1,2,4-t riazole and partitioned into ethyl acetate. All metabolite extracts were then evaporated to dr yness, redissolved in acetonitrile:water (30:70, v:v), and analyzed using LC/MS/MS detection. The LOQs (determined as the LLMVs) were: 0.01 ppm for T and TAA in all matrices and 0.01 ppm for TA in wheat forage, hay, and straw and 0.02 ppm in grain. The LODs were not reported.

The methods were validated prior to and in conjunction with the field trial samples.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 14 of 31 

### C. RESULTS AND DISCUSSION

Sample storage conditions and durations are report ed in Table C.2. Samples were shipped from the field sites to a sample preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samples were stored frozen (<-10 °C at the preparation facility and <- 20 °C at the analytical labor atory) from collection to analysis for propiconazole and propiconazole and metabolites, respectively, fo r 51-348 days (1.7-11.4 months) and 51-363 days (1.7-11.9 months) for forage, 51-358 days (1.7- 11.8 months) and 70-372 da ys (2.3-12.2 months) for hay, 45-313 days (1.5-10.3 months) and 87-3 48 days (2.9-11.4 months) for grain, and 49-318 days (1.6-10.5 months) and 125-378 da ys (4.1-12.4 months) for straw. Sample storage durations prior to analysis for the tri azole metabolites were 39-546 days (1.3-18.0 months) for forage, 43- 339 days (1.4-11.2 months) for hay, 48-313 days (1.6-10.3 months) for grain, and 43-312 days (1.4-10.3 months) for straw. All samples were analyzed within 0-20 days of extraction. Acceptable storage stability data for propiconazo le are available indicat ing that residues of propiconazole and metabolites c onvertible to 2,4-DCBA are stable during frozen storage for up to: 38 months in/on grass forage and straw (DP# 210742, 3/15/95, M. Rodriguez); and for up to 36 months in/on wheat grain (DP# 240856, 2/23/05, T. Morton). In addition, acceptable data have been submitted indicating that residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grai n and 30 months in/on soybean seed (refer to 48681707.der, currently under review). Acceptable storage stability data for the triazole metabolites are available (DP# 363016, 1/12/12, D. Drew; 47606601.der) indicating that residues of T, TA, and TAA are stable during frozen stor age in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but d ecline thereafter. Therefore, residues of T in the 7-day forage samples from trial C30- 9034 were identified for correction by the study reviewer for decline on storage (estimated at 61% based on linear regres sion analysis); however, residues were not corrected for decline on storage since all decline residu es were nondetectable. Additional storage stability data for the tri azole metabolites (DP# 388246, 5/28/08, M. Doherty) indicate that residues of TAA ar e stable in/on wheat grain, forage, hay, and straw for up to 13 months, and that residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. These data are adequate to support the storage durations and conditions of samples from the submitted field trials.

Method validation and concurrent method reco very data for the GC/MSD and LC/MS/MS methods are presented in Table C.1. Sa mples were fortified at 0.01-30.0 ppm with propiconazole, at 0.05-25 ppm with propiconazole and metabo lites, at 0.01-0.1 ppm with T, at 0.01-0.8 ppm with TA, and at 0.01-0.5 ppm with TAA. The methods were adequate for data collection based on acceptable method validation and concurrent recovery da ta. Recoveries were within the acceptable range of 70-120%. The for tification levels used in concurrent method recovery were adequate to bracket expected resi due levels. Apparent re sidues of propiconazole, propiconazole and metabolites determined as 2,4- DCBA, and metabolite T were at or below the LOQ in/on all samples of untreated wheat. Quanti fiable apparent residues of TA were observed in/on nine samples of untreated forage ( 0.01-0.08 ppm), nineteen samples of hay (0.01-0.13 ppm), nine samples of grain (0.02-0.43 ppm), and one sample of straw (0.01 ppm). QuantifiablePropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 15 of 31 

### apparent residues of TAA were observed in/on si x samples of untreated forage (0.01-0.06 ppm), fourteen samples of hay (0.01-0.10 ppm), seve n samples of grain (0.01-0.11 ppm), and four samples of straw (0.01-0.04 ppm). The petitioner attributed the occurren ce of residues of TA and TAA in/on untreated samples to the widespread use of triazoles and the non-specific nature of the common moiety method of analysis. Meth od validation and concurre nt recoveries were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Residue data from the wheat field trials are re ported in Tables C.3.1 (propiconazole) and C.3.2 (triazole metabolites), and the residue data for wheat are summarized in Table C.4. Following two foliar broadcast applications of the 1.02 lb ai/gal SE form ulation of propiconazole at 0.2190- 0.2306 lb ai/A, residues (and per tria l averages) of propiconazole per se and propiconazole and metabolites determined as 2,4-DCBA, respect ively, in/on forage were: 0.271-4.90 (0.271-4.79) and 1.18-9.00 (1.23-8.47) ppm at the 7-da y PHI; and 0.0606-2.16 (0.0813-2.13) and 0.717-5.85 (0.778-5.46) ppm at the 14- to 20-day PHI; corresponding residues in/on hay were: 0.444-9.82 (0.444-9.57) and 1.98-22.5 (1.98-21.6) ppm at th e 7-day PHI; and 0.149-5.48 (0.156-5.41) and 1.57-18.7 (1.62-17.4) ppm at the 14- to 20-day PHI. In/on grain and straw harvested at PHIs of 24-64 days following two applications at 0.2140- 0.2308 lb ai/A, corresponding residues (and per trial averages) were: <0.01-0.0842 (<0.01-0.077 9) and <0.05-0.169 (<0.05-0.145) ppm in/on grain, and 0.0432-4.36 (0.0462-4.04) and 0.570- 13.3 (0.597-12.6) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of wheat forage, hay, grain, and straw. Residues (and per tria l averages) of TA and TAA, respectively, in/on forage were < 0.01-0.0975 (<0.0110-0.0918) and <0.01-0.0336 (<0.01-0.0324) ppm at the 7-day PHI; and <0.01-0.0740 (<0.01-0.0735) and <0.01-0.0444 (<0.01-0.0442) ppm at the 14- to 20-day PHI. Residues (and per tria l averages) of TA and TAA, respectively, in/on hay were 0.0218-0.250 (0.0218-0.236) and <0.01-0.138 (<0.01-0.135) ppm at the 7-day PHI; and 0.0158-0.174 (0.0166-0.166) and <0.01-0.128 (<0.0125-0.116) ppm at the 14- to 20-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.02-0.286 (<0.02-0.279) and <0.01-0.0720 (<0.01- 0.0718) ppm in/on grai n; and <0.01-0.0560 (<0.01-0.0515) and <0.01-0.0510 (<0.01-0.0497) ppm in/on straw.

The residue decline results were variable for all crop matrices. The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4- DCBA generally decreased with increasing PHI in /on wheat forage and hay at both the IA and TX decline trials. Residues of propiconazole per se in/on straw at the IA trial were variable; residues increased from the 25-day PHI to the highest at the 32-day PHI, and then decreased at the 39- and 46-day PHI. Residues of propicona zole and metabolites determined as 2,4-DCBA increased with increasing PHI in/on wheat straw at the IA trial. Re sidues of propiconazole per

se and propiconazole and metabolites determin ed as 2,4-DCBA generally decreased with increasing PHI in/on wheat straw at the TX trial. Residues of propiconazole per se in/on grain were below the LOQ at all sampling intervals at th e IA trial; therefore, re sidue decline could not be assessed. At the TX tria l, residues of propiconazole per se generally decreased with increasing PHI. Residues of propiconazole and metabolites determined as 2,4-DCBA were fairlyPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 16 of 31 

### constant in/on wheat grain at each sampling interval at both the IA and TX decline trials. For the triazole metabolites, residues of T were belo w the LOQ in/on all matrices at all sampling intervals; therefore, residue declin e could not be assessed for either de cline trial. At the IA trial, residues of TA generally increased with incr easing PHI in/on forage and straw, generally decreased with increasing PHI in /on hay, and remained relatively constant in/on grain. At the TX trial, residues of TA genera lly decreased with increasing PHI in/on forage and hay and were below the LOQ at all sampling intervals in/on grai n and straw; therefore, residue decline was not assessed. At the IA trial, residues of TAA gene rally decreased with increasing PHI in/on forage and hay, generally increased with increasing PHI in/on straw, and remained relatively constant in/on grain. At the TX trial, residues of TAA remained relativ ely constant in/on hay and were below the LOQ at all sampling intervals in/on fora ge, grain, and straw; ther efore, residue decline was not assessed.

TABLE C.1. Summary of Method and Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Wheat. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

LC/MS/MS Meth-180
Method Validation Recoveries Wheat Forage Propiconazole 0.01 3 95, 85, 74 85 ± 11 0.1 3 84, 75, 75 78 ± 5.2 Wheat Hay 0.01 3 95, 89, 91 92 ± 3.1 0.1 3 88, 87, 85 87 ± 1.5 Wheat Grain 0.01 3 90, 102, 92 95 ± 6.4 0.1 3 78, 81, 76 78 ± 2.5
Concurrent Recoveries Wheat Forage Propiconazole 0.01 11 103, 80, 88, 84, 89, 89, 95, 99, 84, 96, 83 90 ± 7.3 0.1 9 86, 88, 86, 88, 91, 101, 94, 85, 88 90 ± 5.1
5.0 1 74 74
10 1 90 90 Wheat Hay 0.01 10 89, 90, 82, 97, 87, 89, 108, 93, 102, 83 92 ± 8.2 0.1 8 91, 83, 86, 86, 104, 94, 92, 94 91 ± 6.6
10 1 86 86
30 1 92 92 Wheat Grain 0.01 6 85, 92, 84, 113, 98, 86 93 ± 11 0.1 6 92, 88, 103, 90, 102, 108 97 ± 8.2 Wheat Straw 0.01 6 78, 92, 90, 102, 78, 76 86 ± 10 0.1 5 79, 95, 83, 79, 78 83 ± 7.1
1.0 1 102 102
5.0 1 88 88Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 17 of 31

TABLE C.1. Summary of Method and Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Wheat. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

GC/MSD method AG-626
Method Validation Recoveries Wheat Forage Propiconazole and metabolites determined as 2,4- DCBA 0.05 3 100, 119, 98 106 ± 12 0.5 3 99, 103, 96 99 ± 3.5 Wheat Hay 0.05 3 76, 75, 73 75 ± 1.5 0.5 3 94, 88, 84 89 ± 5.0 Wheat Grain 0.05 3 107, 108, 111 109 ± 2.1 0.5 3 95, 88, 91 91 ± 3.5
Concurrent Recoveries Wheat Forage Propiconazole and metabolites determined as 2,4- DCBA 0.05 12 100, 86, 93, 71, 91, 101, 92, 111, 119, 83, 95, 101 95 ± 13 0.5 8 92, 96, 73, 94, 91, 82, 83, 86 87 ± 7.6 2.5 2 80, 88 84
5.0 1 89 89
20 1 87 87 Wheat Hay 0.05 10 87, 78, 118, 95, 88, 81, 51 4 , 46 4 , 87, 70, 82, 84 87 ± 13 0.5 6 82, 105, 93, 83, 70, 72 84 ± 13 2.5 4 85, 91, 89, 95 90 ± 4.2
5.0 1 84 84
25 1 70 70 Wheat Grain 0.05 9 74, 104, 88, 72, 86, 98, 112, 84, 84 89 ± 13 0.5 8 90, 79, 86, 76, 86, 92, 77, 84 84 ± 5.9
5.0 1 80 80 Wheat Straw 0.05 6 105, 91, 80, 108, 86, 84 92 ± 12 0.5 2 78, 92 85
2.5 1 93 93
5.0 1 80 80
10 1 79 79
15 1 83 83
LC/MS/MS Meth-160
Concurrent Recoveries Wheat Forage T 0.01 13 94, 110, 104, 92, 86, 89, 85, 105, 81, 93, 78, 91, 95 93 ± 9.4

0.1 13 100, 101, 101, 101, 94, 80, 84, 112, 83, 91, 78, 80, 106 93 ± 11

TA 0.01 13 92, 96, 77, 91, 100, 104, 83, 79, 97, 82, 104, 79, 94 91 ± 9.6

0.1 13 101, 105, 100, 101, 106, 105, 93, 91, 107, 95, 106, 103, 107 102 ± 5.4

TAA 0.01 13 93, 102, 82, 121, 110, 110, 92, 99, 106, 109, 116, 105, 107 104 ± 10

0.1 13 90, 97, 84, 102, 103, 116, 106, 99, 111, 112, 103, 109, 110 103 ± 9.1Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 18 of 31

TABLE C.1. Summary of Method and Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Wheat. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3 Wheat Hay T 0.01 12 76, 70, 97, 97, 103, 114, 71, 108, 77, 107, 104, 82 92 ± 16 0.1 12 78, 93, 107, 112, 109, 110, 82, 116, 72, 104, 112, 76 98 ± 16

TA 0.01 12 108, 92, 90, 82, 104, 113, 106, 82, 96, 107, 106, 108 100 ± 11

0.1 11 90, 92, 94, 112, 107, 92, 94, 95, 94, 87, 88 95 ± 7.7
0.2 1 92 92
0.5 1 92 92 TAA 0.01 12 81, 70, 71, 85, 94, 88, 109, 90, 116, 95, 104, 108 93 ± 15 0.1 12 78, 81, 74, 97, 105, 106, 92, 103, 102, 97, 103, 95 94 ± 11
0.5 1 99 99 Wheat Grain T 0.01 8 89, 93, 89, 85, 70, 88, 84, 82 85 ± 7.0 0.1 8 90, 97, 81, 85, 71, 84, 100, 78 86 ± 9.6 TA 0.02 8 104, 99, 117, 119, 94, 109, 71, 110 103 ± 15 0.2 6 81, 95, 113, 79, 73, 76 86 ± 15
0.5 1 116 116
0.8 1 109 109 TAA 0.01 7 105, 72, 101, 104, 80, 71, 103 91 ± 16 0.1 5 79, 83, 100, 75, 71 82 ± 11
0.2 1 96 96
0.3 1 92 92 Wheat Straw T 0.01 6 88, 75, 102, 83, 83, 70 84 ± 11 0.1 6 87, 83, 95, 82, 78, 77 84 ± 6.6 TA 0.01 6 85, 75, 93, 105, 103, 73 89 ± 14 0.1 6 93, 81, 85, 116, 101, 92 95 ± 13 TAA 0.01 6 88, 75, 98, 90, 98, 93 90 ± 8.5 0.1 6 88, 77, 97, 100, 94, 89 91 ± 8.2

1 Concurrent recoveries we re corrected for apparent residues in control samples.
2 Standard deviations are calculate d only for fortification levels having ≥ 3 samples.
3 Means and standard deviations were calculated by the pe titioner except for propiconazole for wheat grain, which had the processing values removed.
4 Recovery was considered invalid because residue in control sa mple exceeds 1⁄2 of the fortification level. Recovery was not used in statistical calculations as per the Study Director.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 19 of 31

TABLE C.2. Summary of Storage Conditions

. Matrix Analyte Storage Temperature (°C) Actual Storage Duration 1 Limit of Demonstrated Storage Stability Propiconazole Forage Propiconazole Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 51-348 days (1.7-11.4 months) Re sidues of propiconazole and metabolites convertible to 2,4- DCBA are stable during frozen storage for up to: 38 months in/on grass forage and straw 2 ; and for up to 36 months in/on wheat grain 3

. Residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/on soybean seed 4

. Propiconazole and Metabolites 51-363 days (1.7-11.9 months)

Hay Propiconazole 51-358 days (1.7-11.8 months) Propiconazole and Metabolites 70-372 days (2.3-12.2 months)

Grain Propiconazole 45-313 days (1.5-10.3 months) Propiconazole and Metabolites 87-348 days (2.9-11.4 months)

Straw Propiconazole 49-318 days (1.6-10.5 months) Propiconazole and Metabolites 125-378 days (4.1-12.4 months)

Triazole metabolites Forage T Frozen at field sites; -10 at preparation facility; -20 at analytical laboratory 42-546 days (1.4-18.0 months) Residues of T, TA, and TAA are stable during frozen storage in/on wheat grain and straw, and residues of TA and TAA are stable in/on wheat forage for up to 4 years; residues of T in wheat forage are relatively stable for up to ~4 or ~12 months, but decline thereafter. 5 Residues of TAA are stable in/on wheat grain, forage, hay, and straw for up to 13 months, and residues of TA are stable in/on wheat grain, forage, and hay, for up to 13 months. 6 TA 39-546 days (1.3-18.0 months) TAA 40-546 days (1.3-18.0 months) Hay T 45-339 days (1.5-11.2 months) TA 44-338 days (1.4-11.1 months) TAA 43-337 days (1.4-11.1months) Grain T 49-312 days (1.6-10.3 months) TA 49-313 days (1.6-10.3 months) TAA 48-312 days (1.6-10.3 months) Straw T 43-309 days (1.4-10.2 months) TA 44-312 days (1.4-10.3 months) TAA 44-312 days (1.4-10.3 months)

1 Interval from harvest to analysis. Extracts were stored 0-20 days prior to analysis.
2 DP# 210742, 3/15/95, M. Rodriguez.
3 DP# 240856, 2/23/05, T. Morton.
4 Refer to 48681707.der, currently under review.
5 DP# 363016, 1/12/12, D. Drew; 47606601.der.
6 DP# 388246, 5/28/08, M. Doherty.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 20 of 31

TABLE C.3.1 Residue Data for Propiconazole fr om Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
Propiconazole Propiconazole and Metabolites Suffolk, VA; 2009 (E07-9031) 2 Pioneer 26R15 [Soft Red

Winter Wheat] Forage 0.2260 7 1.39, 1.44 [1.42] 2.01, 2.21 [2.11] 14 0.620, 0.570 [0.595] 1.36, 1.33 [1.35] Hay 7 1.91, 2.11 [2.01] 3.89, 4.04 [3.97] 14 0.672, 0.612 [0.642] 1.71, 1.57 [1.64] Grain 0.2257 24 <0.01, <0.01 [<0.01] <0.05, 0.0783 [<0.0642] Straw 24 3.41, 3.61 [3. 51] 11.6, 13.2 [12.4] Cheneyville, LA; 2009 (E17-9032) 4 Terral LA841 [Soft Red

Winter Wheat] Forage 0.2218 7 0.642, 0.686 [0.664] 1.18, 1.43 [1.31] 20 0.0745, 0.124 [0.0993] 0.828, 1.04 [0.934] Hay 7 1.28, 1.82 [1.55] 4.35, 4.19 [4.27] 20 0.216, 0.220 [0.218] 1.67, 1.57 [1.62] Grain 0.2237 30 <0.01, <0.01 [<0.01] 0.169, 0.0631 [0.116] Straw 30 1.34, 1.28 [1.31] 8.09, 9.22 [8.66] Northwood, ND; 2009 (C13-9033) 5 Jerry [Hard Red Winter

Wheat] Forage 0.2217 7 0.486, 0.432 [0.459] 1.59, 1.31 [1.45] 14 0.154, 0.144 [0.149] 0.839, 0.717 [0.778] Hay 7 1.08, 1.13 [1.11] 3.39, 3.36 [3.38] 14 0.364, 0.324 [0.344] 1.82, 1.64 [1.73] Grain 0.2215 43 ND, ND [<0.01] <0.05, <0.05 [<0.05]

Straw 43 0.0491, 0.0432 [0.0462] 0.570, 0.624 [0.597]

Bagley, IA; 2009 (C30-9034) 5 Briggs [Hard Red

Spring Wheat] Forage 0.2199 0 2.56 3.60
3 0.660 1.71
7 0.271 1.23
14 0.102, 0.0606 [0.0813] 1.42, 1.04 [1.23]
21 0.0524 1.30 Hay 0 4.90 8.92
3 1.15 4.10
7 0.444 3.15
14 0.149, 0.163 [0.156] 2.78, 2.58 [2.68]
21 0.0908 2.40
Grain 0.2140 25 <0.01 0.0552
32 <0.01 <0.05
39 <0.01, <0.01 [<0.01] 0.0579, 0.0533 [0.0556]
46 <0.01 0.0684
Straw 25 0.0523 0.927
32 0.0877 1.26
39 0.0601, 0.0587 [0.0594] 0.992, 1.83 [1.41]
46 0.0533 2.01Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 21 of 31

TABLE C.3.1 Residue Data for Propiconazole fr om Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
Propiconazole Propiconazole and Metabolites Gardner, ND; 2010 (C12- 9047) 4 5 Maier [Winter Wheat Durum] Forage 0.2247 7 1.36, 1.34 [1.35] 1.74, 2.01 [1.88] 14 0.452, 0.624 [0.538] 1.28, 1.52 [1.40] Hay 7 3.08, 3.47 [3.28] 8.12, 10.4 [9.26] 14 1.70, 1.26 [1.48] 4.71, 4.29 [4.50] Gardner, ND; 2009 (C12- 9035) 4 Grain 0.2297 35 <0.01, <0.01 [<0.01] 0.0521, 0.0601 [0.0561] Straw 35 0.632, 0.419 [0.526] 3.55, 1.92 [2.74]

Raymondville, TX; 2009 (W08- 9036) 6 Caudillo [Hard Red

Winter Wheat] Forage 0.2306 7 4.68, 4.90 [4.79] 7.93, 9.00 [8.47] 14 2.09, 2.16 [2.13] 5.07, 5.85 [5.46] Hay 7 9.82, 9.32 [9.57] 22.5, 20.6 [21.6] 14 5.34, 5.48 [5.41] 16.1, 18.7 [17.4] Grain 0.2270 38 <0.01, <0.01 [<0.01] 0.0602, <0.05 [<0.0551]

Straw 38 0.412, 0.498 [0.455] 3.61, 3.50 [3.56]

Lake Andes, SD; 2009 (C16-9037) 7 Oxen [Hard Red

Spring Wheat] Forage 0.2244 7 0.855, 0.975 [0.915] 2.89, 3.13 [3.01] 14 0.208, 0.254 [0.231] 1.63, 1.61 [1.62] Hay 7 2.96, 2.96 [2.96] 12.7, 7.29 [10.0] 14 0.728, 0.546 [0.637] 4.90, 5.02 [4.96] Grain 0.2247 34 <0.01, ND [<0.01] 0.0759, 0.0747 [0.0753] Straw 34 0.426, 0.319 [0.373] 2.33, 1.56 [1.95] Carrington, ND; 2009 (C13-9038) 7 Glenn [Hard Red

Spring Wheat] Forage 0.2246 7 1.36, 1.20 [1.28] 2.83, 2.68 [2.76] 14 0.778, 0.552 [0.665] 2.54, 2.05 [2.30] Hay 7 2.26, 2.21 [2.24] 6.76 5 , 16.9 5 [11.8] 14 1.50, 1.51 [1.51] 5.67 5 , 14.8 5 [10.2] Grain 0.2228 55 ND, ND [<0.01] <0.05, <0.05 [<0.05] Straw 55 0.748, 0.912 [0.830] 5.32, 4.83 [5.08] Lake Andes, SD; 2009 (C16-9039) 7 Wendy [Hard White Winter Wheat] Forage 0.2190 7 1.54, 1.58 [1.56] 3.35, 3.39 [3.37] 14 0.890, 0.940 [0.915] 2.19, 1.88 [2.04] Hay 7 4.40, 4.06 [4.23] 11.5, 9.58 [10.5] 14 1.98, 2.06 [2.02] 6.55, 6.74 [6.65] Grain 0.2196 64 <0.01, <0.01 [<0.01] <0.05, 0.0541 [<0.0521] Straw 64 0.145, 0.132 [0.139] 1.66, 1.47 [1.57] Carrington, ND; 2009 (C13-9040) 7 Jerry [Hard Red Winter

Wheat] Forage 0.2236 7 1.76, 1.71 [1.74] 4.76, 4.77 [4.77] 14 0.308, 0.438 [0.373] 1.01, 1.12 [1.07] Hay 7 2.04, 1.90 [1.97] 6.12, 4.50 [5.31] 14 0.716, 0.662 [0.689] 2.56, 2.60 [2.58] Grain 0.2257 50 <0.01, ND [<0.01] <0.05, <0.05 [<0.05] Straw 50 0.167, 0.142 [0.155] 1.62, 1.57 [1.60]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 22 of 31

TABLE C.3.1 Residue Data for Propiconazole fr om Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
Propiconazole Propiconazole and Metabolites Groom, TX; 2009 (E13-9041) 8 Cutter [Hard Red

Winter Wheat] Forage 0.2240 0 9.14 12.4
3 5.30 7.23
7 0.772 1.65
14 0.286, 0.345 [0.316] 1.08, 1.22 [1.15]
21 0.205 1.05 Hay 0 26.3 23.0
3 5.66 7.18
7 0.570 1.98
14 0.846, 0.662 [0.754] 2.95, 2.39 [2.67]
21 0.422 1.77
Grain 0.2243 10 0.130 0.152
17 0.0762 0.125
24 0.0842, 0.0715 [0.0779] 0.165, 0.125 [0.145]
30 0.0540 0.155
Straw 10 4.92 6.57
17 2.44 3.81
24 3.78, 2.64 [3.21] 6.09, 4.52 [5.31]
30 0.790 2.16 Levelland, TX; 2009 (W39- 9042) 8 TAM112 [Hard Red

Winter Wheat] Forage 0.2219 7 2.10, 2.43 [2.27] 3.73, 3.80 [3.77] 14 0.975, 0.980 [0.978] 2.63, 2.16 [2.40] Hay 7 3.03, 2.50 [2.77] 7.06, 6.31 [6.69] 14 1.10, 1.03 [1.07] 4.24, 3.65 [3.95] Grain 0.2286 35 0.0107, <0.01 [<0.0104] 0.125, <0.05 [<0.0875] Straw 35 2.73, 2.01 [2.37] 8.24, 6.91 [7.58] Littlefield, TX; 2009 (W39- 9043) 8 Weather
master [Hard Red

Winter Wheat] Forage 0.2209 7 2.69, 2.34 [2.52] 3.96, 3.91 [3.94] 14 1.15, 0.870 [1.01] 1.69, 0.970 [1.33] Hay 7 5.82, 4.93 [5.38] 8.62, 7.26 [7.94] 14 1.85, 1.44 [1.65] 3.82, 4.03 [3.93] Grain 0.2308 35 0.0204, 0.0226 [0 .0215] 0.0909, 0.0992 [0.0951] Straw 35 4.36, 3.72 [4. 04] 13.3, 11.9 [12.6] Ault, CO; 2008 (W12-9044) 8 Jagalene [Hard Red

Winter Wheat] Forage 0.2254 7 1.14, 0.992 [1.07] 2.50, 1.82 [2.16] 14 0.772, 0.872 [0.822] 1.88, 2.29 [2.09] Hay 7 1.89, 1.93 [1.91] 4.67, 4.08 [4.38] 14 1.08, 1.32 [1.20] 3.71, 3.59 [3.65] Grain 0.2240 29 <0.01, ND [<0.01] 0.0542, 0.0570 [0.0556] Straw 29 0.329, 0.232 [0.281] 1.16, 0.847 [1.00] Rupert, ID; 2010 (W15-9046) 11 Klassic [Hard White Spring Wheat] Forage 0.2259 7 0.526, 0.574 [0.550] 1.31, 1.23 [1.27] 14 0.262, 0.275 [0.269] 0.759, 1.38 [1.07] Hay 7 1.39, 1.24 [1.32] 4.03, 4.14 [4.09] 14 0.788, 0.780 [0.784] 3.49, 3.64 [3.57] Grain 0.2285 35 ND, <0.01 [<0.01] <0.05, <0.05 [<0.05] Straw 35 0.0446, 0.0508 [0. 0477] 1.26, 1.67 [1.47]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 23 of 31 1 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
2 For the decline trial, the target PHIs are bolded

. 3 Residues were determ ined as propiconazole per se (LOQ = 0.01 ppm) and as propiconazole and metabolites convertible to 2,4- DCBA (determined as 2,4-DCBA; LOQ = 0.05 ppm). LODs were not reported. ND = not detected, as reported by the petitioner. Per trial averages were calculated by the study reviewer using the LOQ for values reported as <LOQ.
4 Forage and hay samples were not collected in Trial C12-9035. Trial C12-9047 was a dded to generate the required forage and hay samples.
5 The petitioner indicated that Trea ted 7 and 14 day hay samples appear to have be en switched, but this ca nnot be substantiated.

TABLE C.3.2 Residue Data for Triazole Metabolites from Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
T TA TAA

Suffolk, VA; 2009 (E07-9031) 2 Pioneer 26R15 [Soft Red

Winter Wheat] Forage 0.2260 7 ND, ND [<0.01] 0.0485, 0.0510 [0.0498] 0.0200, 0.0224 [0.0212] 14 ND, ND [<0.01] 0.0333, 0.0290 [0.0312] 0.0204, 0.0237 [0.0221] Hay 7 ND, ND [<0.01] 0.0830, 0.104 [0.0935] 0.0316, 0.0396 [0.0356] 14 ND, ND [<0.01] 0.0535, 0.0565 [0.0550] 0.0360, 0.0388 [0.0374] Grain 0.2257 24 <0.01, <0.01 [<0.01] 0.180, 0.200 [0.190] 0.0412, 0.0525 [0.0469] Straw 24 <0.01, <0.01 [<0.01] 0.0130, <0.01 [<0.0115] 0.0510, 0.0484 [0.0497] Cheneyville, LA; 2009 (E17-9032) 4 Terral LA841 [Soft Red

Winter Wheat] Forage 0.2218 7 ND, ND [<0.01] 0.0231, 0.0306 [0.0269] <0.01, <0.01 [<0.01] 20 ND, ND [<0.01] 0.0255, 0.0434 [0.0345] 0.0148, 0.0262 [0.0205] Hay 7 <0.01, <0.01 [<0.01] 0.0550, 0.0500 [0.0525] 0.0155, 0.0147 [0.0151] 20 ND, ND [<0.01] 0.0880, 0.0865 [0.0872] 0.0625, 0.0735 [0.0680] Grain 0.2237 30 <0.01, <0.01 [<0.01] 0.0720, 0.0740 [0.0730] 0.0120, 0.0112 [0.0116] Straw 30 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] 0.0175, 0.0210 [0.0193] Northwood, ND; 2009 (C13-9033) 5 Jerry [Hard Red Winter

Wheat] Forage 0.2217 7 <0.01, <0.01 [<0.01] 0.0178, 0.0176 [0.0177] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0164, 0.0158 [0.0161] <0.01, <0.01 [<0.01] Hay 7 ND, ND [<0.01] 0.0494, 0.0575 [0.0535] 0.0122, 0.0147 [0.0135] 14 ND, ND [<0.01] 0.0422, 0.0418 [0.0420] <0.01 4 , 0.0150 [<0.0125] Grain 0.2215 43 <0.01, <0.01 [<0.01] 0.113, 0.0915 [0.102] 0.0218, 0.0194 [0.0206]
Straw 43 <0.01, <0.01 [<0.01] 0.0162, 0.0158 [0.0160] 0.0154, 0.0174 [0.0164]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 24 of 31

TABLE C.3.2 Residue Data for Triazole Metabolites from Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
T TA TAA

Bagley, IA; 2009 (C30-9034) 5 Briggs [Hard Red

Spring Wheat] Forage 0.2199 0 ND 0.0186 0.0156
3 ND 0.0212 0.0139
7 ND 5 0.0230 0.0166
14 ND, ND [<0.01] 0.0380, 0.0308 [0.0344] 0.0160, 0.0134 [0.0147]
21 ND 0.0266 0.0118 Hay 0 ND 0.0428 0.0341
3 ND 0.0371 0.0328
7 ND 0.0540 0.0389
14 ND, ND [<0.01] 0.0162, 0.0224 [0.0193] 0.0222, 0.0234 [0.0228]
21 ND 0.0128 0.0178
Grain 0.2140 25 <0.01 0.286 0.0466
32 <0.01 0.302 0.0422
39 <0.01, <0.01 [<0.01] 0.271, 0.286 [0.279] 0.0434, 0.0444 [0.0439]
46 <0.01 0.310 0.0452
Straw 25 <0.01 0.0257 0.0110
32 ND 0.0255 0.0144
39 <0.01, <0.01 [<0.01] 0.0560, 0.0470 [0.0515] 0.0381, 0.0352 [0.0367]
46 <0.01 0.0600 0.0462 Gardner, ND; 2010 (C12- 9047) 6 5 Maier [Winter Wheat Durum] Forage 0.2247 7 ND, ND [<0.01] 0.0975, 0.0860 [0.0918] 0.0336, 0.0312 [0.0324] 14 ND, ND [<0.01] 0.0740, 0.0730 [0.0735] 0.0444, 0.0439 [0.0442] Hay 7 ND, <0.01 [<0.01] 0.222, 0.250 [0.236] 0.138, 0.132 [0.135] 14 ND, ND [<0.01] 0.174, 0.158 [0.166] 0.128, 0.103 [0.116] Gardner, ND; 2009 (C12- 9035) 6 Grain 0.2297 35 <0.01, <0.01 [<0.01] 0.198, 0.199 [0.199] 0.0715, 0.0720 [0.0718] Straw 35 <0.01, <0.01 [<0.01] 0.0105, 0.0126 [0.0116] 0.0141, 0.0104 [0.0123]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 25 of 31

TABLE C.3.2 Residue Data for Triazole Metabolites from Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
T TA TAA

Raymondville, TX; 2009 (W08- 9036) 6 Caudillo [Hard Red

Winter Wheat] Forage 0.2306 7 ND, ND [<0.01] 0.0181, 0.0204 [0.0193] <0.01, <0.01 [<0.01] 14 <0.01, <0.01 [<0.01] 0.0278, 0.0252 [0.0265] <0.01, <0.01 [<0.01] Hay 7 <0.01, <0.01 [<0.01] 0.122, 0.128 [0.125] 0.0364, 0.0318 [0.0341] 14 <0.01, <0.01 [<0.01] 0.0975, 0.0965 [0.0970] 0.0245, 0.0246 [0.0246] Grain 0.2270 38 ND, ND [<0.01] 0.178, 0.183 [0.181] 0.0320, 0.0381 [0.0351]

Straw 38 <0.01, ND [<0.01] 0.0269, 0.0288 [0.0279] 0.0304, 0.0308 [0.0306]

Lake Andes, SD; 2009 (C16-9037) 7 Oxen [Hard Red

Spring Wheat] Forage 0.2244 7 ND, ND [<0.01] 0.0264, 0.0200 [0.0232] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0236, 0.0288 [0.0262] <0.01, <0.01 [<0.01] Hay 7 <0.01, <0.01 [<0.01] 0.0540, 0.0510 [0.0525] 0.0238, 0.0242 [0.0240] 14 ND, ND [<0.01] 0.0237, 0.0208 [0.0223] 0.0240, 0.0244 [0.0242] Grain 0.2247 34 <0.01, <0.01 [<0.01] 0.211, 0.214 [0.213] 0.0378, 0.0368 [0.0373] Straw 34 <0.01, <0.01 [<0.01] 0.0116, 0.0132 [0.0124] 0.0204, 0.0259 [0.0232] Carrington, ND; 2009 (C13-9038) 7 Glenn [Hard Red

Spring Wheat] Forage 0.2246 7 ND, ND [<0.01] 0.0116, 0.0134 [0.0125] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0170, 0.0111 [0.0141] <0.01, <0.01 [<0.01] Hay 7 ND, ND [<0.01] 0.0230, 0.0297 [0.0264] 0.0164, 0.0199 [0.0182] 14 ND, ND [<0.01] 0.0173, 0.0158 [0.0166] 0.0161, 0.0162 [0.0162] Grain 0.2228 55 <0.01, ND [<0.01] 0.0820, 0.0655 [0.0738] 0.0257, 0.0195 [0.0226] Straw 55 <0.01, <0.01 [<0.01] <0.01, 0.0104 [<0.0102] 0.0190, 0.0204 [0.0197]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 26 of 31

TABLE C.3.2 Residue Data for Triazole Metabolites from Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
T TA TAA

Lake Andes, SD; 2009 (C16-9039) 7 Wendy [Hard White Winter Wheat] Forage 0.2190 7 ND, ND [<0.01] 0.0307, 0.0284 [0.0296] 0.0148, 0.0142 [0.0145] 14 ND, ND [<0.01] 0.0248, 0.0298 [0.0273] 0.0190, 0.0206 [0.0198] Hay 7 <0.01, <0.01 [<0.01] 0.0900, 0.0920 [0.0910] 0.0496, 0.0530 [0.0513] 14 <0.01, <0.01 [<0.01] 0.0715, 0.0730 [0.0723] 0.0494, 0.0540 [0.0517] Grain 0.2196 64 ND, <0.01 [<0.01] 0.206, 0.199 [0.203] 0.0400, 0.0373 [0.0387] Straw 64 <0.01, <0.01 [<0.01] 0.0122, 0.0138 [0.0130] 0.0120, 0.0129 [0.0125] Carrington, ND; 2009 (C13-9040) 7 Jerry [Hard Red Winter

Wheat] Forage 0.2236 7 <0.01, <0.01 [<0.01] 0.0278, 0.0287 [0.0283] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0187, 0.0192 [0.0190] <0.01, <0.01 [<0.01] Hay 7 ND, <0.01 [<0.01] 0.0710, 0.0655 [0.0683] 0.0149, 0.0136 [0.0143] 14 ND, ND [<0.01] 0.0449, 0.0494 [0.0472] 0.0250, 0.0252 [0.0251] Grain 0.2257 50 <0.01, <0.01 [<0.01] 0.116, 0.106 [0.111] 0.0194, 0.0212 [0.0203] Straw 50 <0.01, <0.01 [<0.01] 0.0200, 0.0171 [0.0186] 0.0180, 0.0174 [0.0177] Groom, TX; 2009 (E13-9041) 8 Cutter [Hard Red

Winter Wheat] Forage 0.2240 0 <0.01 0.0146 <0.01
3 <0.01 0.0163 <0.01
7 ND 0.0130 <0.01
14 ND, ND [<0.01] 0.0120, 0.0131 [0.0126] <0.01, <0.01 [<0.01]
21 ND 0.0106 <0.01 Hay 0 <0.01 0.0461 0.0152
3 <0.01 0.0128 <0.01
7 ND 0.0218 <0.01
14 ND, ND [<0.01] 0.0328, 0.0361 [0.0345] 0.0252, 0.0255 [0.0254]
21 ND 0.0307 0.0228
Grain 0.2243 10 ND <0.02 <0.01
17 ND <0.02 <0.01
24 ND, ND [<0.01] <0.02, <0.02 [<0.02] <0.01, <0.01 [<0.01]
30 ND <0.02 <0.01
Straw 10 <0.01 <0.01 <0.01
17 <0.01 <0.01 <0.01
24 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01]
30 <0.01 <0.01 <0.01Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 27 of 31

TABLE C.3.2 Residue Data for Triazole Metabolites from Wheat Field Trials with Propiconazole.
Trial ID (City, State; Year) Zone Wheat Variety Commodity Total Rate 1 (lb ai/A) PHI 2 (days) Residues (ppm) 3 [Average]
T TA TAA

Levelland, TX; 2009 (W39- 9042) 8 TAM112 [Hard Red

Winter Wheat] Forage 0.2219 7 <0.01, <0.01 [<0.01] 0.0133, 0.0140 [0.0137] <0.01, 0.0109 [<0.0105] 14 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] Hay 7 <0.01, <0.01 [<0.01] 0.0322, 0.0294 [0.0308] 0.0192, 0.0174 [0.0183] 14 <0.01, <0.01 [<0.01] 0.0233, 0.0216 [0.0225] 0.0209, 0.0170 [0.0190] Grain 0.2286 35 ND, ND [<0.01] 0.0515, 0.0555 [0.0535] 0.0130, 0.0134 [0.0132] Straw 35 <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01] 0.0104, <0.01 [<0.0102] Littlefield, TX; 2009 (W39- 9043) 8 Weather
master [Hard Red

Winter Wheat] Forage 0.2209 7 <0.01, <0.01 [<0.01] 0.0189, 0.0180 [0.0185] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0136, 0.0128 [0.0132] <0.01, <0.01 [<0.01] Hay 7 <0.01, <0.01 [<0.01] 0.0450, 0.0474 [0.0462] <0.01, 0.0111 [<0.0106] 14 <0.01, <0.01 [<0.01] 0.0353, 0.0354 [0.0354] 0.0140, 0.0132 [0.0136] Grain 0.2308 35 <0.01, <0.01 [<0.01] 0.133, 0.132 [0.133] 0.0212, 0.0206 [0.0209] Straw 35 <0.01, <0.01 [<0.01] 0.0158, 0.0158 [0.0158] 0.0219, 0.0204 [0.0212] Ault, CO; 2008 (W12-9044) 8 Jagalene [Hard Red

Winter Wheat] Forage 0.2254 7 ND, ND [<0.01] <0.01, 0.0119 [<0.0110] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0130, 0.0184 [0.0157] <0.01, <0.01 [<0.01] Hay 7 <0.01, <0.01 [<0.01] 0.0314, 0.0279 [0.0297] 0.0138, 0.0130 [0.0134] 14 <0.01, <0.01 [<0.01] 0.0372, 0.0268 [0.0320] 0.0168, 0.0148 [0.0158] Grain 0.2240 29 <0.01, <0.01 [<0.01] 0.138, 0.150 [0.144] 0.0200, 0.0218 [0.0209] Straw 29 ND, ND [<0.01] 0.0107, 0.0177 [0.0142] 0.0106, 0.0102 [0.0104] Rupert, ID; 2010 (W15-9046) 11 Klassic [Hard White Spring Wheat] Forage 0.2259 7 ND, ND [<0.01] 0.0138, 0.0128 [0.0133] <0.01, <0.01 [<0.01] 14 ND, ND [<0.01] 0.0134, 0.0136 [0.0135] <0.01, <0.01 [<0.01] Hay 7 <0.01, <0.01 [<0.01] 0.0505, 0.0520 [0.0513] 0.0166, 0.0184 [0.0175] 14 ND, ND [<0.01] 0.0442, 0.0375 [0.0409] 0.0242, 0.0236 [0.0239] Grain 0.2285 35 ND, <0.01 [<0.01] 0.0428, 0.0515 [0.0472] <0.01, <0.01 [<0.01] Straw 35 <0.01, ND [<0.01] <0.01, <0.01 [<0.01] <0.01, <0.01 [<0.01]Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 28 of 31 1 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
2 For the decline trial, the target PHIs are bolded

. 3 The LOQs (determined as the LLMVs) were: 0.01 ppm for T and TAA in all matrices and 0.01 pp m for TA in forage, hay, and straw and 0.02 ppm in grain. ND = not detected, as reporte d by the petitioner. Per trial averages were calculated by the study reviewer using the LOQ for values reported as <LOQ.
4 The petitioner indicated that the control and treated hay samples appear to be switched but cannot be substantiated.
5 For trial C30-9034, residues of T in forage were identified by the study reviewer for correcti on for decline on storage (estim ated at 61% based on linear regression analysis); however, residues were not corrected for decline on storage since all decline resi dues were ND. 6 Forage and hay samples were not collected in Trial C12-9035. Trial C12-9047 was a dded to generate the required forage and hay samples.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 29 of 31

TABLE C.4. Summary of Residue Data from Wh eat Crop Field Trials with Propiconazole. Commodity Analyte Total App. Rate (lb ai/A) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev.
Wheat Forage Propiconazole 0.2190- 0.2306 7 15 0.271 4.90 0.271 4.79 1.28 1.44 1.13 Propiconazole and Metabolites 15 1.18 9.00 1.23 8.47 2.16 2.88 1.90

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.01 0.0975 <0.0110 0.0918 0.0193 0.0261 0.0207
TAA 15 <0.01 0.0336 <0.01 0.0324 0.0100 0.0130 0.0063 Propiconazole 14-20 15 0.0606 2.16 0.0813 2.13 0.538 0.611 0.528 Propiconazole and Metabolites 15 0.717 5.85 0.778 5.46 1.35 1.75 1.14

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.01 0.0740 <0.01 0.0735 0.0190 0.0245 0.0159
TAA 15 <0.01 0.0444 <0.01 0.0442 0.0100 0.0148 0.0093 Wheat Hay Propiconazole 0.2190- 0.2306 7 15 0.444 9.82 0.444 9.57 2.01 2.75 2.30 Propiconazole and Metabolites 15 1.98 22.5 1.98 21.6 5.31 7.22 5.01

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 0.0218 0.250 0.0218 0.236 0.0525 0.0688 0.0541
TAA 15 <0.01 0.138 <0.01 0.135 0.0182 0.0300 0.0315 Propiconazole 14-20 15 0.149 5.48 0.156 5.41 0.784 1.24 1.28 Propiconazole and Metabolites 15 1.57 18.7 1.62 17.4 3.65 4.78 4.13

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 0.0158 0.174 0.0166 0.166 0.0409 0.0527 0.0400
TAA 15 <0.01 0.128 <0.0125 0.116 0.0242 0.0331 0.0274
Wheat Grain Propiconazole 0.2140- 0.2308 24-64 15 <0.01 0.0842 <0.01 0.0779 0.0100 0.0153 0.0176 Propiconazole and Metabolites 15 <0.05 0.169 <0.05 0.145 0.0556 0.0705 0.0286

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.02 0.286 <0.02 0.279 0.133 0.135 0.0744
TAA 15 <0.01 0.0720 <0.01 0.0718 0.0209 0.0283 0.0172
Wheat Straw Propiconazole 24-64 15 0.0432 4.36 0.0462 4.04 0.455 1.16 1.41 Propiconazole and Metabolites 15 0.570 13.3 0.597 12.6 2.74 4.50 4.05

T 15 <0.01 <0.01 <0.01 <0.01 0.01 0.01 N/A
TA 15 <0.01 0.0560 <0.01 0.0515 0.0124 0.0162 0.0109
TAA 15 <0.01 0.0510 <0.01 0.0497 0.0177 0.0200 0.0114

1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LOQ was used fo r any results reported as <LOQ in Tables C.3.1. and C.3.2 N/A = Not applicable.
2 LAFT = lowest average field trial; HAFT = highest average field trial.



### D. CONCLUSION

The submitted wheat field trial data are adequate. Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation of propic onazole at 0.2190-0.2306 lb ai/A, residues (and perPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 30 of 31 

### trial averages) of propiconazole per se and propiconazole and metabolites determined as 2,4- DCBA, respectively, in/on forage were: 0.271-4.90 (0.271-4.79) and 1.18-9.00 (1.23-8.47) ppm at the 7-day PHI; and 0.0606-2.16 (0.0813-2.13) and 0.717-5.85 (0.778-5.46) ppm at the 14- to 20-day PHI; corresponding residues in/on hay were: 0.444-9.82 (0.444-9.57) and 1.98-22.5 (1.98-21.6) ppm at the 7-day PHI; and 0.149-5.48 (0.156-5.41) and 1.57-18.7 (1.62-17.4) ppm at the 14- to 20-day PHI. In/on grain and stra w harvested at PHIs of 24-64 days following two applications at 0.2140-0.2308 lb ai /A, corresponding residues (and per trial averages) were: <0.01-0.0842 (<0.01-0.0779) and <0.05-0.169 (< 0.05-0.145) ppm in/on grain, and 0.0432-4.36 (0.0462-4.04) and 0.570-13.3 (0.597-12.6) ppm in/on straw.

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of wheat forage, hay, grain, and straw. Residues (and per tria l averages) of TA and TAA, respectively, in/on forage were < 0.01-0.0975 (<0.0110-0.0918) and <0.01-0.0336 (<0.01-0.0324) ppm at the 7-day PHI; and <0.01-0.0740 (<0.01-0.0735) and <0.01-0.0444 (<0.01-0.0442) ppm at the 14- to 20-day PHI. Residues (and per tria l averages) of TA and TAA, respectively, in/on hay were 0.0218-0.250 (0.0218-0.236) and <0.01-0.138 (<0.01-0.135) ppm at the 7-day PHI; and 0.0158-0.174 (0.0166-0.166) and <0.01-0.128 (<0.0125-0.116) ppm at the 14- to 20-day PHI. Residues (and per trial averages) of TA and TAA, respectively, in/on grain and straw were: <0.02-0.286 (<0.02-0.279) and <0.01-0.0720 (<0.01- 0.0718) ppm in/on grai n; and <0.01-0.0560 (<0.01-0.0515) and <0.01-0.0510 (<0.01-0.0497) ppm in/on straw.

The residue decline results were variable for all crop matrices. The residue decline data indicate that residues of propiconazole per se and propiconazole and metabolites determined as 2,4- DCBA generally decreased with increasing PHI in /on wheat forage and hay at both the IA and TX decline trials. Residues of propiconazole per se in/on straw at the IA trial were variable; residues increased from the 25-day PHI to the highest at the 32-day PHI, and then decreased at the 39- and 46-day PHI. Residues of propicona zole and metabolites determined as 2,4-DCBA increased with increasing PHI in/on wheat straw at the IA trial. Re sidues of propiconazole per

se and propiconazole and metabolites determin ed as 2,4-DCBA generally decreased with increasing PHI in/on wheat straw at the TX trial. Residues of propiconazole per se in/on grain were below the LOQ at all sampling intervals at th e IA trial; therefore, re sidue decline could not be assessed. At the TX tria l, residues of propiconazole per se generally decreased with increasing PHI. Residues of propiconazole and metabolites determined as 2,4-DCBA were fairly constant in/on wheat grain at each sampling interval at both the IA and TX decline trials. For the triazole metabolites, residues of T were belo w the LOQ in/on all matrices at all sampling intervals; therefore, residue declin e could not be assessed for either de cline trial. At the IA trial, residues of TA generally increased with incr easing PHI in/on forage and straw, generally decreased with increasing PHI in /on hay, and remained relatively constant in/on grain. At the TX trial, residues of TA genera lly decreased with increasing PHI in/on forage and hay and were below the LOQ at all sampling intervals in/on grai n and straw; therefore, residue decline was not assessed. At the IA trial, residues of TAA gene rally decreased with increasing PHI in/on forage and hay, generally increased with increasing PHI in/on straw, and remained relatively constant in/on grain. At the TX trial, residues of TAA remained relativ ely constant in/on hay and werePropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.1/7.4.2/OPPTS 860.1500/OECD IIA 6.3.1, 6.3.2, 6.3.3 and IIIA 8.3.1, 8.3.2, 8.3.3 Crop Field Trial/ Residue Decline - Wheat

DP# 400030/MRID No. 48681704 Page 31 of 31 

### below the LOQ at all sampling intervals in/on fora ge, grain, and straw; ther efore, residue decline was not assessed.

Acceptable methods were used for residue qua ntitation, and the study is supported by adequate storage stability data.

E. REFERENCES

DP# 210742, 3/15/95, M. Rodriguez. DP# 240856, 2/23/05, T. Morton. DP# 388246, 5/28/08, M. Doherty DP# 363016, 1/12/12, D. Drew; 47606601.der.

F. DOCUMENT TRACKING

RDI: T. Morton(2/27/2013); S. Hummel (2/27/2013) Petition Number: 2F7975 DP Barcode(s): 400030 PC Code: 122101

Template Version June 2005.Prop iconazo le!PC Code I 2210 1 / S yngenta Cr op Pr otec tion

, L L C DAC O 7.4

. 5/0P PT S 860.1520 / 0ECD UA 6.5.4 and Ili A 8

. 5



### Primary Ev aluator

Approved by , hur s t o n G. Morton
, Che mi st

### 509P**)**

# ~v.~ Susan V. Hwnmel

, Senior S c i en t ist H E D / RABIV (7509P) Date: 2/2 7 / 13

Dat e: 2/27/ 1 3

N ote: Th is DER was originally prepared und e r contract by Versar
, I nc. ( 6850 Versar Cent er. S pringfi eld. VA 221 5 1 ; submitt ed 6/27/J 2). Th e DER ha s been rev ie w ed by the H ea lth E ffects D ivi sion ( HED ) and revised to reflect curre n t Office of Pesticide Prog rams (OP P ) polici es.



### S T U DY REPORTS:

48681704 Hampt o n , M. (20 11 ) Azoxystrobin/P r opico nazol e SE (Al5909C)

- Magni tude ofth e Residue s in or on Wheat : F inal R epo rt. Pr ojec t Numb er : TK0003213
, T004407/08. U npubli s hed study prepar e d by Syngenta Cro p Pro tec tion

, Dra gon Run Ag Services, Inc. and Pes t Managem e nt Enterprises, In c. 1167 p

.



### EXECUTIVE SUMMARY:

Syngenta Crop Protecti on, LL C. ha s submitted processi n g data f o r pr o piconazole on wheat. The

su bmi ss ion als o includes data for azoxystrobin. R efe r to 48681 704 proces si ng. de 1 for data
p e rtain i ng t o a zo x ys trobin

.



### In two c rop field trials conducted in LA and ND
, wheat received two foliar broadcas t applications of a multiple ac ti ve ingredient ( MAl ) su spo -e mulsion (S E) f o rmulation (Quilt XcelTM ) containing 1.18 lb ai / gal azox ystrobin and 1 .02 lb ai / gal p r o picon azole. Applicati o n s

were ta r geted at 14 da ys prior to Feekes 10.54, and Feek es 10.54. Eac h tr ea ted plot recei ved two appli c a tions ofpropico nazole at a n exa gge rated r ate (5x field rat e) of0.5518-0.5572lb ail A

/a pplication, for a total sea s onal ra te of l. l0 9 l b ai / A. Applications we r e mad e a t 13

- to 14- day retreatment i nterv a ls (RTl s) using g round equipment in spra y volume s of**.29 ~20.04**  

### ga l / A. A nonioni c s urfactant (N IS) was a dded to the spray mixtures for all appl ica tions in one trial

, and

a crop oil con ce n t rat e (COC) was added to th e s p r ay mixture s at t h e seco nd trial si te

. Wh eat gr a in was harv e sted fr o m the plots at a 3 0- to 55

- day pr eha rvest i nterval ( PHI) and proc essed int o A GF
, b r an, flour

, ge rm , middlin gs , and short s using s imulated conun e rcial pr o cedures. Pro cess ing w as conducte d b y GLP Techn olog ies (N a v a so ta , TX)

. A deq uate de sc ripti ons wer e pro vid ed o f the proce ssi ng pr oce dures

, including materi a l balanc e summ a r i es.

Application rates in the submi ss ion were rep orted in term s oftotall b ai / A for combined application of azoxy st robin and propiconazole ( refer to pg. 12 of MRID 48681704). Indi vi dual
app licat i on rate s for azo xy s tr obi n and propic on azole w e re calculated by the stud y review e r based

on the ratio of the active ingr e dients in th e pr o duct: 1 .1 8 / 2.2 for azoxystrobi n or 1.02/2.2 for
p r opico na zole.

DP# 400030/MRID No. 48681704 Page I of 19Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 2 of 19 

### Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a high performance liquid chromatography met hod with tandem mass spectrometry detection (LC/MS/MS), Morse Laboratories Meth-180. The lim it of quantitation (LOQ; determined as the lowest limit of method validation; LLMV) was 0.01 ppm. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas chromatography with mass select ive detection (GC/MSD), Nova rtis Crop Protection method AG-626. This is a common moiety method in wh ich all residues of c oncern are converted by base hydrolysis and oxidation to 2,4-DCBA, then de termined as the 2,4-DCBA methyl ester, and reported in propiconazole equivalents. The LOQ (determined as the LLMV) was 0.05 ppm. Samples were analyzed for the triazole metabolit es 1,2,4-triazole (T), tria zole alanine (TA), and triazole acetic acid (TAA) using LC/MS/MS, Morse Laboratories Meth-160, Revision #2. The LOQs (determined as the LLMVs) were: 0.01 ppm for T in all matrices; 0.02 ppm for TA in grain, AGF, middlings, and shorts, 0.05 ppm in flour, 0.13 ppm in bran, and 0.15 ppm in germ; and 0.01 ppm for TAA in grain, middlings and shorts, 0.015 ppm in AGF, 0.02 ppm in bran and germ, and 0.05 ppm in flour. The methods were adequate for data collection based on acceptable method validation and concurrent recovery data. The fortification levels used in concurrent method recovery were adequate to bracket e xpected residue levels. Method validation and concurrent recoveries were corrected for apparent residues in controls; treated samples were not corrected for residues in controls.

Samples were shipped from the processor to a sa mple preparation facility, where they were homogenized prior to shipment to the analytical laboratory. Samp les were stored under ambient conditions (field sites) and frozen (<-10 °C at the preparation facili ty and <-20 °C at the analytical laboratory) from harvest/processing to analysis. Processing took place within 398 days of harvest. Sample analyses for pr opiconazole and propicon azole and metabolites, respectively, were complete d within 189-455 days (6.2-15.0 m onths) and 202-468 days (6.6-15.4 months) for grain (RAC) and 52-67 days (1.7- 2.2 months) and 59-74 days (1.9-2.4 months) for the processed commodities. Sample storage du rations prior to analysis for the triazole metabolites were 176-447 days (5.8-14.7 months ) for grain (RAC) and 37-60 days (1.2-2.0 months) for the processed commodities. All sa mples were analyzed within 0-11 days of extraction. Adequate storage stab ility data are available to suppor t the sample storage durations and conditions of samples from the submitted trials.

Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation at 1.109 lb ai/A, average residues of propiconazole and propiconazole and metabol ites determined as 2,4-DCBA, respectively, were: 0.0228-0.0552 and 0.210-0.251 pp m in/on wheat grain (RAC); 2.28-4.46 and 6.97-9.63 ppm in AGF; 0.0436-0.0677 and 0.497-0.557 ppm in bran; <0.01-0.0216 and 0.0987- 0.155 ppm in middlings; <0.01-0.0270 a nd 0.0786-0.239 ppm in shorts; 0.0436-0.0683 and 0.383-0.514 ppm in germ; and, were below the LOQ in flour. The processing data indicate that propiconazole and propiconazole and metabolites may concentr ate in AGF, bran, and germ (average processing factors of 36-90x, 1.6-2.3x, a nd 1.6-2.0x) but do not c oncentrate in flour, middlings, and shorts (average proce ssing factors of <0.22-<0.31x, <0.41-0.54x, and <0.46- 0.66x, respectively).Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 3 of 19 

### For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of wheat grain RAC and the processed commodities; therefore, processing factors were not calculated. Average residues of TA a nd TAA, respectively, were: 0.228-0.647 and 0.0413-0.207 ppm in/on wheat grain (RAC); 0.110- 0.570 and 0.0558-0.247 ppm in AGF; 0.568-1.74 and 0.0708-0.331 ppm in bran; <0.05-0.169 and < 0.05-0.263 ppm in flour; 0.111-0.261 and 0.0350- 0.182 ppm in middlings; 0.200-0.304 and 0.0450-0.228 ppm in shorts; and, 0.520-3.41 and 0.0615-0.478 ppm in germ. The processing data indi cate that TA may concentrate in bran and germ (average processing factors of 2.6x a nd 3.8x) but do not concentrate in AGF, flour, middlings, and shorts (average pr ocessing factors of 0.68x, <0.24x, 0.45x, and 0.67x, respectively). The processing data indicate thatTAA may concentrate in AGF, bran, shorts, and germ (average processing factors of 1.3x, 1.7x, 1.1x, and 1.9x) but do not concentrate in flour and middlings (average processing f actors of <0.76x and 0.86x, respectively).

The processing factors calculated in this st udy were less than the maximum theoretical concentration factors for wheat of 7.7x for br an, 1.4x for flour, and 8.3x for shorts (based on separation into components; OCSPP 860.1520, Table 3).

STUDY/WAIVER ACCEPTABILITY/ DEFICIENCIES/CLARIFICATIONS :
Under the conditions and parameters used in th e study, the processed comm odity residue data are classified as scientifically acceptable. The accepta bility of this study for regulatory purposes is addressed in the forthcoming U.S. EPA Residue Chemistry Summary Document [DP# 400030].

COMPLIANCE :
Signed and dated Good Laboratory Practice (GLP), Quality Assurance, a nd Data Confidentiality statements were provided. No deviations fr om regulatory requirement s were reported which would have an impact on the validity of the study.

A. BACKGROUND INFORMATION

Propiconazole is a triazole-type fungicide that provides broad spectrum disease control through inhibition of sterol biosynthesis in fungi. It is registered to Syngenta Crop Protection for the control of fungal diseases on a variety of crops.

The nomenclature of propiconazole , 1,2,4-triazole (T), triazole al anine (TA), and triazole acetic acid (TAA) are summarized in Table A.1, and th e physicochemical properties of propiconazole are summarized in Table A.2.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 4 of 19

TABLE A.1. Nomenclature of Propiconazole and Triazoles. Compound

Common name Propiconazole Company experimental names CGA-64250 IUPAC name 1-[2-(2,4_dichlorophenyl)-4-propyl- 1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole CAS name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1, 3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole
CAS # 60207-90-1

End-use products/EP Suspo-emulsion (SE) formulation (Quilt XcelTM) containing 1. 18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole Compound

Common name 2,4-DCBA Chemical name 2,4-dichlorobenzoic acid Compound

Common name 1,2,4-Triazole (T)
Chemical name 1 H -1,2,4-triazole CAS registry number 288-88-0 Compound

Common name Triazole alanine or triazolylalanine (TA)
Chemical name α -amino-1 H -1,2,4-triazole-1-propanoic acid CAS registry number 114419-45-3 Compound

Common name Triazole acetic acid or triazolylacetic acid (TAA)
Chemical name 1 H -1,2,4-triazole-1-acetic acid CAS registry number 28711-29-7 N N N

O O
Cl Cl

N H N

N

N N N

O H NH 2

O

N N N

O H OPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 5 of 19

TABLE A.2. Physicochemical Properties of Technical Grade Propiconazole.
Parameter Value Reference Boiling point 120°C at 1.9 Pa, >250°C at 101.325 kPa MRID No.:43698701 pH 4.9 @ 25°C (1% aqueous dispersion) MRID No.:43698701 Density 1.289 g/cm3 typical @ 20°C MRID No.: 43698701 Water solubility (20°C) 0.10 g/L at 20°C MRID No.: 41720301

Solvent solubility (temperature not specified) Completely miscible in ethanol, acetone, toluene and n-octanol. n-hexane = 47 g/L MRID No.: 42030201 Vapor pressure at 25°C 4.2 x 10 -7 mm Hg @ 25°C MRID No.: 41720301 Dissociation constant (pK a ) 1.09 MRID No.: 43698701 Octanol/water partition coefficient Log(K OW ) (25 °C) 3.72 @ pH 6.6 MRID No.: 43698701 UV/visible absorption spectrum ( 8 max, nm) Not available MRID No.: 40583703



### B. EXPERIMENTAL DESIGN

B.1. Application and Crop Information
In two crop field trials conducted in LA a nd ND, wheat received two foliar broadcast applications of a 1.02 lb ai/gal SE formulation of propiconazole (Quilt XcelTM). Applications were targeted at 14 days prior to Feekes 10.54, a nd Feekes 10.54. Each treated plot received two applications of propiconazole at an exa ggerated rate (5x field rate) of 0.5518-0.5572 lb ai/A/application, for a tota l seasonal rate of 1.109 lb ai/A. Applications were made at 13- to 14- day RTIs using ground equipment in spray volum es of 5.29-20.04 gal/A. An NIS was added to the spray mixtures for all applications in one tria l, and a COC was added to the spray mixtures at the second trial site. Samples of grain were harvested at matur ity (PHIs of 30-55 days). Study use pattern data are re ported in Table B.1.

TABLE B.1. Study Use Pattern. Location (City, State; Year) Trial ID EP 1 Application Information Tank Mix/ Adjuvants 4 Method; Timing Volume (gal/A) Rate 2 (lb ai/A) RTI 3 (days) Total Rate 2 (lb ai/A) Cheneyville, LA; 2009 (E17-9032) 1.02 lb ai/gal SE 1. Foliar broadcast; 80% headed 5.29 0.5572 -- 1.109 NIS 2. Foliar broadcast; Early milk 5.94 0.5518 14 Carrington, ND; 2009 (C13-9038) 1.02 lb ai/gal SE 1. Foliar broadcast; BBCH 37 20.04 0.5560 -- 1.109 COC 2. Foliar broadcast; BBCH 69 19.86 0.5530 13

1 EP = End-use Product; a multiple active ingredient (MAI) sus po-emulsion (SE) formulation (Quilt XcelTM) containing 1.18 lb ai/gal azoxystrobin and 1.02 lb ai/gal propiconazole.
2 Application rates in the submission were reported in terms of total lb ai/A for combined application of azoxystrobin and propiconazole. Individual application rates for propiconazole were calculated by the study reviewer based on the ratio of the active ingredient in the product: reported rate X 1.02/2.2.
3 RTI = Retreatment Interval.
4 NIS = non-ionic surfactant. COC = crop oil concentrate.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 6 of 19 

### B.2. Sample Handling and Processing Procedures

Single control and treated bulk samples of wheat grain were collected from each plot and shipped via FedEx at ambient temp eratures 1-7 days after collecti on to the processing facility, GLP Technologies (Navasota, TX) for processi ng into AGF, bran, flour, middlings, shorts, and germ. At GLP Technologies, samples were stored frozen ( ≤ 10 °F) prior to processing. Processing was completed within 398 days of harv est, and the samples were returned to frozen storage for up to 7 days prior to shipment to the preparation facilit y, Syngenta Crop Protection (Greensboro, NC), where they were maintain ed frozen (<-10 °C) prior to and following preparation. In preparation for analysis, samp les were homogenized by grinding in a Hobart food cutter in the presence of dry ice. Within 25- 26 days of receipt at th e preparation facility, samples were shipped frozen via FedEx to th e analytical laboratory, Morse Laboratories (Sacramento, CA), where they were maintain ed frozen (~ -20 °C) prior to analysis.

The processing procedures simulated commercial operations of wheat production as closely as possible to generate the required fraction of wheat grain (RAC) a nd the processed fractions, with some variations to commercial methods. Proc essing flowcharts for wheat AGF and processed fractions, copied without a lteration from MRID 48681704, are pr esented in Figures B.2.1 and B.2.2, respectively.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 7 of 19 

### FIGURE B.2.1. Processing Flowchart fo r Wheat Aspirated Grain Fractions.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 8 of 19 

### FIGURE B.2.2. Processing Flowchart for Wh eat Bran, Flour, Middlings, Shorts, and Germ.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 9 of 19 

### B.3. Analytical Methodology

Samples were analyzed for residues of pr opiconazole (determined as propiconazole per se ) using a LC/MS/MS method, Morse Laboratories Meth -180. Samples were also analyzed for propiconazole and its metabolites convertible to 2,4-dichlorobenz oic acid (2,4-DCBA) using gas GC/MSD, Novartis Crop Prot ection method AG-626. This is a common moiety method in which all residues of concern are converted by base hydrolysis and oxidation to 2,4-DCBA, then determined as the 2,4-DCBA methyl ester, and re ported in propiconazole equivalents. Samples were analyzed for the triazole metabolites T, TA, and TAA using LC/MS/MS, Morse Laboratories Meth-160, Revision #2.

For determination of residues of propiconazole per se , samples were extracted with methanol:water (80:20, v:v) and filtered. Water and saturated NaCl solution were added to an aliquot of the filtrate, which was then partitioned three times with hexane. The combined hexane extracts were evaporated to dryness, reconstitu ted in acetonitrile:wate r (30:70, v:v), and then analyzed using LC/MS/MS. The LOQ (determined as the LLMV) was 0.01 ppm; the limit of detection (LOD) was not reported.

For determination of residues of propiconazo le and metabolites conve rtible to 2,4-DCBA, samples were refluxed with methanol:ammonium hydroxide (80:20, v:v). An aliquot of the extract was evaporated to dryness. The residues were dissolved in aqueous NaOH and heated in the presence of potassium permanganate for oxidation of propiconazole and metabolites to 2,4- DCBA. The sample was acidified with HCl and pa rtitioned with hexane:eth yl ether (90:10, v:v). The organic phase was evaporated to dryness and derivatized with diazom ethane to form the methyl ester of 2,4-DCBA. The derivatized extract was evaporated to dryness, reconstituted in hexane, and purified using an al umina solid phase extraction (SPE ) cartridge. The sample was reduced to a known volume using nitrogen evaporat ion and then analyzed using GC/MSD. The LOQ (determined as the LLMV) was 0.05 ppm; the LOD was not reported.

For determination of T, TA, and TAA, samples we re extracted with methanol:water (80:20, v:v). Following the addition of Celite, the extracts were vacuum filtered, rinsed, and brought to volume with methanol:water (80:20, v:v). For dete rmination of TAA, an aliquot of the extract were purified by SPE and then derivatized by HC l/butanol esterification. The TA aliquot underwent two derivatizations: an esterificati on using HCl/butanol a nd an acylation using heptafluorobutyric anhydride (HFBA). The T al iquot was directly derivatized with dansyl chloride to produce the dansyl derivative of 1,2,4-t riazole and partitioned into ethyl acetate. All metabolite extracts were then evaporated to dr yness, redissolved in acetonitrile:water (30:70, v:v), and analyzed using LC/MS/MS detection. The LOQs (determined as the LLMVs) were: 0.01 ppm for T in all matrices; 0.02 ppm for TA in grain, AGF, middlings, and shorts, 0.05 ppm in flour, 0.13 ppm in bran, and 0.15 ppm in ge rm; and 0.01 ppm for TAA in grain, middlings, and shorts, 0.015 ppm in AGF, 0.02 ppm in bran and germ, and 0.05 ppm in flour. The LODs were not reported.

The methods were validated prior to and in conjunction with the field trial samples.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 10 of 19 

### C. RESULTS AND DISCUSSION

Sample storage conditions and durations are report ed in Table C.2. Samples were shipped from the processor to a sample prepar ation facility, where they were homogenized prior to shipment to the analytical laboratory. Samples were stored under ambient conditions (f ield sites) and frozen (<-10 °C at the preparation facility and <- 20 °C at the analyti cal laboratory) from harvest/processing to analysis. Processing t ook place within 398 days of harvest. Sample analyses for propiconazole and propiconazole and metabolites, respec tively, were completed within 189-455 days (6.2-15.0 months) and 202-468 days (6.6-15.4 months) for grain (RAC) and 52-67 days (1.7-2.2 months) and 59-74 days (1.9 -2.4 months) for the processed commodities. Sample storage durations prior to analysis fo r the triazole metabolite s were 176-447 days (5.8- 14.7 months) for grain (RAC) and 37-60 days (1 .2-2.0 months) for the processed commodities. All samples were analyzed within 0-11 days of extraction. Acceptable storage stability data for propiconazole are available indicat ing that residues of propicon azole and metabolites convertible to 2,4-DCBA are stable during froz en storage for up to: 38 months in/on grass forage and straw (DP# 210742, 3/15/95, M. Rodriguez); and for up to 36 months in/on wheat grain (DP# 240856, 2/23/05, T. Morton). In addition, acceptable data have been submitted indicating that residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/on soybean seed (refer to 48681707.der). Acceptable storage stability data for the triazole metabolites are available (DP# 363016, 1/12/12, D. Drew; 47606601.der) indicating that residues of T, TA, and TAA are stable during fr ozen storage in/on wheat grain and flour, and residues of TA and TAA are stable in wheat bran for up to 4 years; residues of T in wheat bran are relatively stable for up to 1 year, but decline thereafter. Additional storage stability data for the triazole metabolites (DP# 388246, 5/28/08, M. D oherty) indicate that residues of TA and TAA are stable in/on wheat grain for up to 13 mont hs. These data are ad equate to support the storage durations and cond itions of samples from the submitted field trials.

Method validation and concurrent method reco very data for the GC/MSD and LC/MS/MS methods are presented in Table C.1. Samples we re fortified at 0.01-5.0 ppm with propiconazole, at 0.05-10 ppm with propiconazole and metabolites, at 0.01-0.1 ppm with T, at 0.02-4.0 ppm with TA, and at 0.01-2.5 ppm with TAA. The me thods were adequate for data collection based on acceptable method validation and concurrent rec overy data. Recoveries were within the acceptable range of 70-120%. The fo rtification levels used in c oncurrent method recovery were adequate to bracket expected re sidue levels. Apparent residues of propiconazole, propiconazole and metabolites determined as 2,4-DCBA, and meta bolite T were at or below the LOQ in/on all samples of untreated wheat. Quantifiable appa rent residues of TA we re observed in/on one sample each of untreated AGF (0.13 ppm), bran (0.61 ppm), flour (0.10 ppm), germ (1.5 ppm), middlings (0.16 ppm), and shorts (0.19 ppm). Quantifiable appa rent residues of TAA were observed in/on one sample each of untreated AGF (0.10 ppm), bran (0.19 ppm), flour (0.18 ppm), germ (0.28 ppm), middlings (0.15 ppm), and s horts (0.20 ppm). The petitioner attributed the occurrence of residue s of TA and TAA in/on untreated sa mples to the widespread use of triazoles and the non-specific nature of the common moiety method of analysis. Method validation and concurrent recoveries were correc ted for apparent residues in controls; treated samples were not corrected for residues in controls.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 11 of 19 

### Residue data from the wheat processing study are reported in Tables C.3. 1 (propiconazole) and C.3.2 (triazole metabolites). Follo wing two foliar broadcast applica tions of the 1.02 lb ai/gal SE formulation at 1.109 lb ai/A, average residue s of propiconazole a nd propiconazole and metabolites determined as 2,4-DCBA, respectively, were: 0.0228-0.0552 and 0.210-0.251 ppm in/on wheat grain (RAC); 2.28-4.46 and 6.97-9.63 ppm in AGF; 0.0436-0.0677 and 0.497-0.557 ppm in bran; <0.01-0.0216 and 0.0987-0.155 ppm in middlings; <0.01-0.0270 and 0.0786-0.239 ppm in shorts; 0.0436-0.0683 and 0.383-0.514 ppm in ge rm; and, were below the LOQ in flour. The processing data indicate that propicon azole and propiconazole and metabolites may concentrate in AGF, bran, and germ (avera ge processing factors of 36-90x, 1.6-2.3x, and 1.6- 2.0x) but do not concentrate in fl our, middlings, and shorts (ave rage processing factors of <0.22- <0.31x, <0.41-0.54x, and <0.46-0.66x, respectively).

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of wheat grain RAC and the processed commodities; therefore, processing factors were not calculated. Average residues of TA a nd TAA, respectively, were: 0.228-0.647 and 0.0413-0.207 ppm in/on wheat grain (RAC); 0.110- 0.570 and 0.0558-0.247 ppm in AGF; 0.568-1.74 and 0.0708-0.331 ppm in bran; <0.05-0.169 and < 0.05-0.263 ppm in flour; 0.111-0.261 and 0.0350- 0.182 ppm in middlings; 0.200-0.304 and 0.0450-0.228 ppm in shorts; and, 0.520-3.41 and 0.0615-0.478 ppm in germ. The processing data indi cate that TA may concentrate in bran and germ (average processing factors of 2.6x a nd 3.8x) but do not concentrate in AGF, flour, middlings, and shorts (average pr ocessing factors of 0.68x, <0.24x, 0.45x, and 0.67x, respectively). The processing data indicate thatTAA may concentrate in AGF, bran, shorts, and germ (average processing factors of 1.3x, 1.7x, 1.1x, and 1.9x) but do not concentrate in flour and middlings (average processing f actors of <0.76x and 0.86x, respectively).

The processing factors calculated in this st udy were less than the maximum theoretical concentration factors for wheat of 7.7x for br an, 1.4x for flour, and 8.3x for shorts (based on separation into components; OCSPP 860.1520, Table 3).

TABLE C.1. Summary of Method and Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Wheat Matrices. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3
LC/MS/MS Meth-180
Method Validation Recoveries
Wheat Grain 4 Propiconazole 0.01 3 90, 102, 92 95 ± 6.4 0.1 3 78, 81, 76 78 ± 2.5 Wheat Flour 0.01 3 78, 72, 74 75 ± 3.1 0.1 3 75, 71, 70 72 ± 2.6 Wheat Germ 0.01 3 93, 95, 97 95 ± 2.0 0.1 3 97, 98, 98 98 ± 0.58Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 12 of 19

TABLE C.1. Summary of Method and Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Wheat Matrices. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

Concurrent Recoveries Wheat Grain Propiconazole 0.01 1 92 92
1.0 1 84 84
Wheat AGF 0.01 1 73 73
0.1 1 71 71
5.0 1 104 104
Wheat Bran 0.01 1 80 80
0.1 1 83 83
Wheat Flour 0.01 1 75 75
0.1 1 70 70
Wheat Middlings 0.01 1 79 79
0.1 1 78 78 Wheat Shorts 0.01 2 75, 83 79 0.1 2 76, 70 73
Wheat Germ 0.01 1 93 93
0.1 1 86 86
GC/MSD method AG-626
Method Validation Recoveries
Wheat Grain 4 Propiconazole and metabolites determined as 2,4- DCBA 0.05 3 107, 108, 111 109 ± 2.1 0.5 3 95, 88, 91 91 ± 3.5 Wheat Flour 0.05 3 98, 91, 104 98 ± 6.5 0.5 3 92, 99, 90 94 ± 4.7 Wheat Germ 0.05 3 101, 104, 102 102 ± 1.5 0.5 3 87, 91, 86 88 ± 2.6
Concurrent Recoveries Wheat AGF Propiconazole and metabolites determined as 2,4- DCBA 0.05 1 93 93
10 1 82 82
Wheat Bran 0.05 1 92 92
5.0 1 88 88
Wheat Flour 0.05 1 86 86
10 1 77 77
Wheat Middlings 0.05 1 104 104
10 1 85 85
Wheat Shorts 0.05 1 84 84
5.0 1 84 84
Wheat Germ 0.05 1 99 99
10 1 76 76Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 13 of 19

TABLE C.1. Summary of Method and Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Wheat Matrices. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3

LC/MS/MS Meth-160
Concurrent Recoveries
Wheat AGF T 0.01 1 84 84
0.1 1 89 89
TA 0.02 1 94 94
0.3 1 121 121
3.0 1 118 118
TAA 0.015 1 97 97
0.25 1 101 101
2.5 1 99 99 Wheat Bran T 0.01 2 88, 102 95 0.1 2 90, 102 96
TA 0.13 1 100 100 0.2 2 70, 90 80 2.0 3 79, 88, 101 89 ± 11
TAA 0.02 1 100 100
0.04 1 77 77
0.4 1 75 75
0.5 1 98 98 Wheat Flour T 0.01 2 102, 105 104 0.1 2 92, 102 97 TA 0.05 2 104, 78 91 0.5 2 81, 73 77 TAA 0.05 2 84, 90 87 0.5 2 73, 96 84
Wheat Middlings T 0.01 2 92, 97 94 0.1 2 104, 111 108 TA 0.02 2 116, 71 94
0.2 1 86 86
0.5 1 73 73 TAA 0.01 2 90, 82 86
0.1 1 88 88
0.5 1 88 88 Wheat Shorts T 0.01 2 108, 106 107 0.1 2 109, 104 106 TA 0.02 2 114, 77 96
0.2 1 104 104
0.5 1 79 79 TAA 0.01 2 91, 91 91
0.1 1 91 91
0.5 1 88 88Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 14 of 19

TABLE C.1. Summary of Method and Concurrent R ecoveries of Propiconazole and its Triazole Metabolites from Wheat Matrices. Matrix Analyte Spike Level (ppm) Sample Size (n) Recoveries (%) 1 Mean ± Std. Dev. (%) 2,3 Wheat Germ T 0.01 2 113, 101 107 0.1 2 117, 99 108
TA 0.15 1 102 102 0.3 2 105, 112 108 3.0 2 100, 108 104
4.0 1 99 99
TAA 0.02 1 100 100
0.05 1 103 103 0.5 2 101, 104 102

1 Concurrent recoveries we re corrected for apparent residues in control samples.
2 Standard deviations are calculate d only for fortification levels having ≥ 3 samples.
3 Means and standard deviations were calculated by the petitioner.
4 Method recovery data for grain are also presen ted in the crop field trial DER (48681704.de2).

TABLE C.2. Summary of Storage Conditions

. Matrix Analyte Storage Temperature (°C) Actual Storage Duration 1 Limit of Demonstrated Storage Stability Propiconazole Grain Propiconazole Ambient at field sites; 10 °F at processor; -10 at preparation facility; -20 at analytical laboratory 189-455 days (6.2-15.0 months) Residues of propiconazole and metabolites convertible to 2,4- DCBA are stable during frozen storage for up to: 38 months in/on grass forage and straw 2 ; and for up to 36 months in/on wheat grain 3

. Residues of propiconazole per se are stable during frozen storage for up to 24 months in/on barley grain and 30 months in/on soybean seed 4

. Propiconazole and Metabolites 202-468 days (6.6-15.4 months)

AGF Propiconazole 55-62 days (1.8-2.0 months) Propiconazole and Metabolites 67-74 days (2.2-2.4 months)

Bran Propiconazole 52-59 days (1.7-1.9 months) Propiconazole and Metabolites 59-66 days (1.9-2.2 months)

Flour Propiconazole 56-63 days (1.8-2.1 months) Propiconazole and Metabolites 67-73 days (2.2-2.4 months)

Middlings Propiconazole 60- 67 days (2.0-2.2 months) Propiconazole and Metabolites 65-72 days (2.1-2.4 months)

Shorts Propiconazole 62-64 days (2.0-2.1 months) Propiconazole and Metabolites 65-72 days (2.1-2.4 months)

Germ Propiconazole 56-63 days (1.8-2.1 months) Propiconazole and Metabolites 67-74 days (2.2-2.4 months)Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 15 of 19

TABLE C.2. Summary of Storage Conditions

. Matrix Analyte Storage Temperature (°C) Actual Storage Duration 1 Limit of Demonstrated Storage Stability
Triazole metabolites Grain T Ambient at field sites; 10 °F at processor; -10 at preparation facility; -20 at analytical laboratory 176-442 days (5.8-14.5 months) Residues of T, TA, and TAA are stable during frozen storage in/on wheat grain and flour, and residues of TA and TAA are stable in wheat bran for up to 4 years; residues of T in wheat bran are relatively stable for up to 1 year, but decline thereafter. 5 Residues of TAA are stable in/on wheat grain for up to 13 months, and residues of TA are stable in/on wheat grain for up to 13 months. 6 TA 181-447 days (6.0-14.7 months) TAA 181-447 days (6.0-14.7 months) AGF T 43-50 days (1.4-1.6 months) TA 42-49 days (1.4-1.6 months) TAA 43-50 days (1.4-1.6 months) Bran T 38-50 days (1.3-1.6 months) TA 38-51 days (1.3-1.7 months) TAA 38-51 days (1.3-1.7 months) Flour T 38-59 days (1.3-1.9 months) TA 43-60 days (1.4-2.0 months) TAA 44-60 days (1.4-2.0 months) Middlings T 38-55 days (1.3-1.8 months) TA 37-56 days (1.2-1.8 months) TAA 38-56 days (1.3-1.8 months) Shorts T 38-57 days (1.3-1.9 months) TA 44-57 days (1.4-1.9 months) TAA 38-56 days (1.3-1.8 months) Germ T 39-50 days (1.3-1.6 months) TA 38-51 days (1.3-1.7 months) TAA 39-51 days (1.3-1.7 months)

1 Interval from harvest to analysis. Extracts were stored 0-11 days prior to analysis. Samples were processed within 398 days of harvest.
2 DP# 210742, 3/15/95, M. Rodriguez.
3 DP# 240856, 2/23/05, T. Morton.
4 Refer to 48681707.der.
5 DP# 363016, 1/12/12, D. Drew; 47606601.der.
6 DP# 388246, 5/28/08, M. Doherty.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 16 of 19

TABLE C.3.1 Residue Data for Propiconazole from Wheat Processing Study with Propiconazole.
RAC Processed Commodity Total Rate (lb ai/A) PHI Residues (ppm) 1 [Average] Processing Factor 2

Propiconazole Propiconazole and metabolites Propiconazole Propiconazole and metabolites Cheneyville, LA; 2009 (E17-9032) Wheat Grain (RAC) 1.109 30 0.0590, 0.0601, 0.0465 [0.0552] 0.255, 0.218, 0.280 [0.251] -- --

AGF 4.49, 4.43 [4.46] 9.05, 10.2 [9.63] 81x 38x Bran 0.0724, 0.0629 [0.0677] 0.519, 0.475 [0.497] 1.2x 2.0x

Flour <0.01, <0.01 [<0.01] <0.05, <0.05 [<0.05] <0.18x <0.20x

Middlings 0.0210, 0.0221 [0.0216] 0.153, 0.157 [0.155] 0.39x 0.62x

Shorts 0.0286, 0.0254 [0.0270] 0.236, 0.241 [0.239] 0.49x 0.95x

Germ 0.0730, 0.0635 [0.0683] 0.370, 0.395 [0.383] 1.2x 1.5x

Carrington, ND; 2009 (C13-9038) Wheat Grain (RAC) 1.109 55 0.0256, 0.0200, 0.0227 [0.0228] 0.214, 0.227, 0.188 [0.210] -- --

AGF 2.28, 2.28 [2.28] 7.41, 6.53 [6.97] 100x 33x Bran 0.0441, 0.0431 [0.0436] 0.507, 0.607 [0.557] 1.9x 2.7x

Flour <0.01, <0.01 [<0.01] <0.05, <0.05 [<0.05] <0.44x <0.24x

Middlings <0.01, <0.01 [<0.01] 0.109, 0.0883 [0.0987] <0.44x 0.47x

Shorts <0.01, <0.01 [<0.01] 0.0764, 0.0807 [0.0786] <0.44x 0.37x

Germ 0.0453, 0.0419 [0.0436] 0.513, 0.514 [0.514] 1.9x 2.4x

Average Wheat Grain (RAC) 1.109 30- 55 -- -- AGF 90x 36x
Bran 1.6x 2.3x
Flour <0.31x <0.22x Middlings <0.41x 0.54x

Shorts <0.46x 0.66x
Germ 1.6x 2.0x

1 The LOQ was 0.01 and 0.05 ppm for propiconazole and propiconazole and metabolites, respectively, in all matrices. Per trial average residues were calculated by the study reviewer using the LOQ for all residues reported as <LOQ.
2 Processing Factor = [Measured residue for analyte in the pro cessed fraction] / [Measured residue for analyte in the grain RAC ].Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 17 of 19

TABLE C.3.2 Residue Data for Triazole Metabolites from Wheat Processing Study with Propiconazole.
RAC Processed Commodity Total Rate (lb ai/A) PHI Residues (ppm) 1 [Average] Processing Factor 2

T TA TAA T TA TAA Cheneyville, LA; 2009 (E17-9032) Wheat Grain (RAC) 1.109 30 <0.01, <0.01, <0.01 [<0.01] 0.224, 0.223, 0.236

[0.228] 0.0410, 0.0416, 0.0412 [0.0413] -- -- --

AGF <0.01, <0.01 [<0.01] 0.111, 0.108 [0.110] 0.0565, 0.0550 [0.0558] NC 3 0.48x 1.4x

Bran <0.01, <0.01 [<0.01] 0.520, 0.615 [0.568] 0.0660, 0.0755 [0.0708] NC 2.5x 1.7x

Flour <0.01, <0.01 [<0.01] <0.05, <0.05 [<0.05] <0.05, <0.05 [<0.05] NC <0.22x <0.24x 4

Middlings <0.01, <0.01 [<0.01] 0.130, 0.0925 [0.111] 0.0382, 0.0318 [0.0350] NC 0.49x 0.85x

Shorts <0.01, <0.01 [<0.01] 0.243, 0.156 [0.200] 0.0510, 0.0390 [0.0450] NC 0.88x 1.1x

Germ <0.01, <0.01 [<0.01] 0.505, 0.535 [0.520] 0.0600, 0.0630 [0.0615] NC 2.3x 1.5x

Carrington, ND; 2009 (C13-9038) Wheat Grain (RAC) 1.109 55 <0.01, <0.01, <0.01 [<0.01] 0.620, 0.590, 0.730

[0.647] 0.192, 0.192, 0.236

[0.207] -- -- --

AGF <0.01, <0.01 [<0.01] 0.595, 0.545 [0.570] 0.248, 0.246 [0.247] NC 0.88x 1.2x

Bran <0.01, <0.01 [<0.01] 1.72, 1.76 [1.74] 0.306, 0.355 [0.331] NC 2.7x 1.6x

Flour <0.01, <0.01 [<0.01] 0.186, 0.152 [0.169] 0.247, 0.278 [0.263] NC 0.26x 1.3x

Middlings <0.01, <0.01 [<0.01] 0.289, 0.233 [0.261] 0.198, 0.165 [0.182] NC 0.40x 0.88x

Shorts <0.01, <0.01 [<0.01] 0.394, 0.214 [0.304] 0.284, 0.171 [0.228] NC 0.47x 1.1x

Germ <0.01, <0.01 [<0.01] 3.50, 3.32 [3.41] 0.465, 0.491 [0.478] NC 5.3x 2.3xPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 18 of 19

TABLE C.3.2 Residue Data for Triazole Metabolites from Wheat Processing Study with Propiconazole.
RAC Processed Commodity Total Rate (lb ai/A) PHI Residues (ppm) 1 [Average] Processing Factor 2

T TA TAA T TA TAA Average Wheat Grain (RAC) 1.109 30- 55 -- -- -- AGF NC 0.68x 1.3x
Bran NC 2.6x 1.7x
Flour NC <0.24x <0.76x Middlings NC 0.45x 0.86x

Shorts NC 0.67x 1.1x
Germ NC 3.8x 1.9x

1 The LOQs were: 0.01 ppm for T in all ma trices; 0.02 ppm for TA in grain, AGF, midd lings, and shorts, 0.05 ppm in flour, 0.13 ppm in bran, and 0.15 ppm in germ; and 0.01 ppm for TAA in gr ain, middlings, and shorts, 0.015 ppm in AGF, 0.02 ppm in bran, and germ, and 0.05 ppm in flour.
2 Processing Factor = [Measured residue for analyte in the pro cessed fraction] / [Measured residue for analyte in the grain RAC ]. 3 NC = Not calculated; resi dues were below the LOQ in bot h RAC and processed fraction.
4 To account for the 5-fold difference betw een the LOQ values for TAA in grain and flour, a 5x adjustment was included in the calculation of the proce ssing factor for flour.



### D. CONCLUSION

The submitted wheat processing study is acceptable. Following two foliar broadcast applications of the 1.02 lb ai/gal SE formulation at 1.109 lb ai/A, average residues of propiconazole and propiconazole and metabolites determined as 2,4-DCBA, respectively, were: 0.0228-0.0552 and 0.210-0.251 ppm in/on wheat grain (RAC); 2.28-4.46 and 6.97-9.63 ppm in AGF; 0.0436-0.0677 and 0.497-0.557 ppm in bran; <0.01-0.0216 a nd 0.0987-0.155 ppm in middlings; <0.01-0.0270 and 0.0786-0.239 ppm in shorts; 0.0436-0.0683 and 0.383- 0.514 ppm in germ; and, were below the LOQ in flour. The processing data indicat e that propiconazole and propiconazole and metabolites may concentrate in AGF, bran, and ge rm (average processing factors of 36-90x, 1.6- 2.3x, and 1.6-2.0x) but do not concentr ate in flour, middlings, and shorts (average processing factors of <0.22-<0.31x, <0.41-0.54x , and <0.46-0.66x, respectively).

For the triazole metabolites, residues of T were below the LOQ (<0.01 ppm) in/on all samples of wheat grain RAC and the processed commodities; therefore, processing factors were not calculated. Average residues of TA a nd TAA, respectively, were: 0.228-0.647 and 0.0413-0.207 ppm in/on wheat grain (RAC); 0.110- 0.570 and 0.0558-0.247 ppm in AGF; 0.568-1.74 and 0.0708-0.331 ppm in bran; <0.05-0.169 and < 0.05-0.263 ppm in flour; 0.111-0.261 and 0.0350- 0.182 ppm in middlings; 0.200-0.304 and 0.0450-0.228 ppm in shorts; and, 0.520-3.41 and 0.0615-0.478 ppm in germ. The processing data indi cate that TA may concentrate in bran and germ (average processing factors of 2.6x a nd 3.8x) but do not concentrate in AGF, flour, middlings, and shorts (average pr ocessing factors of 0.68x, <0.24x, 0.45x, and 0.67x, respectively). The processing data indicate thatTAA may concentrate in AGF, bran, shorts, and germ (average processing factors of 1.3x, 1.7x, 1.1x, and 1.9x) but do not concentrate in flour and middlings (average processing factors of <0.76x and 0.86x, respectively). The observed concentration factors were less than the theoretical concentration factors.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.4.5/OPPTS 860.1520/OECD IIA 6.5.4 and IIIA 8.5 Processed Food and Feed - Wheat

DP# 400030/MRID No. 48681704 Page 19 of 19 

### An acceptable method was used for residue quant itation, and the study is supported by adequate storage stability data.

E. REFERENCES

DP# 210742, 3/15/95, M. Rodriguez. DP# 240856, 2/23/05, T. Morton. DP# 388246, 5/28/08, M. Doherty DP# 363016, 1/12/12, D. Drew; 47606601.der.

F. DOCUMENT TRACKING

RDI: T. Morton(2/27/2013); S. Hummel (2/27/2013) Petition Number: 2F7975 DP Barcode(s): 400030 PC Code: 122101

Template Version June 2005

# • +1 Propiconazole/PC Code 122 1 0 l/Syngenta Crop Protection, LLC**~** DA CO 7.3 / 0PPTS 860.1380/0ECD IIA 6.1.1 and lil A 8.1.1


## = 

# I Storage Stability- Sugar beet tops and r oots, soybean (seed), barley grain

, and apple



### Approved by
Susan V. Hummel

, Senior Scientist HED /RA BIV (7509P) Date: 2/27/13

Date : 2 / 27 / 13

Note: This Data Evaluation Record (DE R ) was origina lly prepared under contract by Ve r sar, Inc

. ( 6850 Ve r sar Center
, Springfield

, VA 22151; submitted 6 / 27 / 12). Th e DER has been reviewed by HED and revised to reflect
current Office of Pesticide Program s (OPP) policie s.



### STUDY REPORT:

48681707 Royer, A. 

### (2009) Prop i conazole- Stability of Propiconazole (CGA64250) Residue s in Sugar Beet Tops and Roots
, Soybean, Bar l ey Gr ain and App le s Under F r eezer Storage Conditions: Final Report. Project Number: T003886 / 05
, T003886/05/REG. Unpublished study
prepar e d by Eurofins / ADME Bioanalyses. 43 p.



### EXECUTIVE SUMMARY:

Syngenta Crop Protection, LLC. has submitted the results of a storage stabili ty study with propiconazole on sugar beet tops and root, soy b ea n (seed), barley grain, and apple. Untreated samples were fort i fied with prop i conazole at 0.1 ppm. The treated samp les were store d frozen (

- 20 ± 5 °C )
, and were analyzed at target storage intervals of

- 0, 3, 6, 1 2, and 24 months (all te ste d
crop matr i ces) and 30 month s (soybean). Actua l storage int ervals were: 0 day s, 90

- 91 day s (3. 0 month s), 1 8 3- 184 days ( 6.1 months)

, 364-365 days ( 1 2.0 month s)
, 750-751 da ys (24.7 months), and 916 day s (30 .1 months). The study was co nduc ted by Eurofins / ADME Bioanalyses (V ergeze, France).

Samples were analyzed for residues of propiconazole 

### per se using a high performance liqu i d chromatography method with tandem mass spec tr o m e try de tect i on (LCIMSIMS)
, method REM 130. 11 (also referenced as AGR/MOA/PROPIC

- 4 at Eu rofins /ADME Bioanalyses). The m et hod

was adequate for da ta collection based o n acce ptabl e concurre nt r ecovery dat a. The limi t of quantitatio n (LOQ) as reported by the petitioner was 0.01 ppm for all matrices.

Th e stu d y results indicate that residues of prop i conazo l e are stable under frozen storage conditions (-20 ± 

### 5°C) for up to 24 m onths inion s u gar beet tops and root, barley grai n , and apple, and for up to 30 m onths inion soybean.



### STUDY 

### IW AIVER ACCEPT ABILITY /DEFICIENCIES/CLARIFICATIONS:

Unde r the conditi ons and parameters used in the s tud y, the storage stability data are classified as scientifica ll y acceptable. The acceptability of this stu dy for regulatory purposes is addressed i n the forthcoming U.S. EPA Residue Chemistry Summary Document [DP# 400030].

DP# 400030/MRID No. 48681707 Pa ge I of6Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.3/OPPTS 860.1380/OECD IIA 6.1.1 and IIIA 8.1.1 Storage Stability – Sugar beet tops and roots, soybean (seed), barley grain, and apple

DP# 400030/MRID No. 48681707 Page 2 of 6 

### COMPLIANCE :
Signed and dated Good Laboratory Practice (G LP), Quality Assurance and No Data Confidentiality statements were provided. No deviations from regul atory requirements were reported which would have an impact on the validity of the study.

A. BACKGROUND INFORMATION

Propiconazole is a triazole-type fungicide that provides broad spectrum disease control through inhibition of sterol biosynthesis in fungi. It is registered to Syngenta Crop Protection for the control of fungal diseases on a variety of crops.

The chemical structure and nomenclature of pr opiconazole, and the physicochemical properties of the technical grade propiconazole ar e presented in Tables A.1 and A.2.

TABLE A.1. Nomenclature of Propiconazole. Compound

Common name Propiconazole Company experimental names CGA-64250 IUPAC name 1-[2-(2,4_dichlorophenyl)-4-propyl- 1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole CAS name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1, 3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole
CAS # 60207-90-1 End-use products/EP Not applicable

TABLE A.2. Physicochemical Properties of Technical Grade Propiconazole.
Parameter Value Reference Boiling point 120°C at 1.9 Pa, >250°C at 101.325 kPa MRID No.:43698701 pH 4.9 @ 25°C (1% aqueous dispersion) MRID No.:43698701 Density 1.289 g/cm3 typical @ 20°C MRID No.: 43698701 Water solubility (20°C) 0.10 g/L at 20°C MRID No.: 41720301

Solvent solubility (temperature not specified) Completely miscible in ethanol, acetone, toluene and n-octanol. n-hexane = 47 g/L MRID No.: 42030201 Vapor pressure at 25°C 4.2 x 10 -7 mm Hg @ 25°C MRID No.: 41720301 Dissociation constant (pK a ) 1.09 MRID No.: 43698701 Octanol/water partition coefficient Log(K OW ) (25 °C) 3.72 @ pH 6.6 MRID No.: 43698701 UV/visible absorption spectrum ( 8 max, nm) Not available MRID No.: 40583703 N N N

O O
Cl ClPropiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.3/OPPTS 860.1380/OECD IIA 6.1.1 and IIIA 8.1.1 Storage Stability – Sugar beet tops and roots, soybean (seed), barley grain, and apple

DP# 400030/MRID No. 48681707 Page 3 of 6 

### B. EXPERIMENTAL DESIGN

B.1. Sample Handling and Preparation

Samples of sugar beets, soybean seed, and barley grain were supplied by Syngenta; apples were purchased at a local supermarket. Sugar beet tops and roots and barley grain were received homogenized. Soybeans and apples were prepared at the analyt ical laboratory by chopping and homogenizing using a horizontal food cutter in the presence of dry ice. The homogenized samples were stored at -20 ± 5 °C until analysis.

Subsamples (10 g) of the bulk homogenized cont rol samples for each crop matrix were weighed into 50-mL polypropylene conical tubes and indivi dually fortified at a rate of 0.1 ppm with a fortification standard of propic onazole in methanol. The solven t was allowed to evaporate, and the samples were sealed and stored in a temper ature-monitored freezer at a nominal temperature of -20 ± 5 °C.

Two fortified replicate samples of each crop ma trix were analyzed on day 0, and two fortified replicate samples of each crop matrix were re moved for analysis after 3, 6, 12, and 24 months (all tested crop matrices) and 30 months (soybean ) at a nominal temperature of -20 ± 5 °C. Freshly fortified samples were prepared and an alyzed as procedural recovery (concurrent recovery) samples for each matrix and time interval. Actual storage intervals (based on the interval from fortification to extraction) were : 0 days, 90-91 days (3.0 months), 183-184 days (6.1 months), 364-365 days (12.0 months), 750-7 51 days (24.7 months), and 916 days (30.1 months). Samples were analyzed within 0-4 days of extraction.

The petitioner noted that there we re two instances during which temp eratures increased to up to - 15 or -5.4 °C; however, because the specimens rema ined frozen during these intervals, there was no impact to the study.

B.2. Analytical Methodology

Samples were analyzed for residues of propiconazole per se using LC/MS/MS, REM 130.11 (also referenced as AGR/MOA/PROPIC-4 at Euro fins/ADME Bioanalyses). A brief description of the method was included in the submission.

Briefly, samples were extracte d by homogenization with metha nol:ultra pure water mixture (80:20 v:v) on a flatbed shaker for 2 hours, followed by filtration. A 2-mL aliquot was diluted up to 10 mL with methanol:ultra pure wate r (5:95 v:v) for anal ysis by LC/MS/MS.

The LOQ (as reported by the petitioner) was 0.0 1 ppm for all matrices; the limit of detection (LOD) was not provided.

The analytical method was validated in conjunc tion with analysis of the study samples.Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.3/OPPTS 860.1380/OECD IIA 6.1.1 and IIIA 8.1.1 Storage Stability – Sugar beet tops and roots, soybean (seed), barley grain, and apple

DP# 400030/MRID No. 48681707 Page 4 of 6 

### C. RESULTS AND DISCUSSION

The concurrent recovery data are presented in Ta ble C.1. The data indicate that the LC/MS/MS method was adequate for the determin ation of residues of propiconazole per se in sugar beet tops and root, soybean, barley grain, a nd apple. Concurrent recoveries were within the acceptable range of 70-120% for all crop matrices. Apparent residues of propiconazole in control samples were below the LOQ (<0.01 ppm), and adequate example chromatograms were provided. It could not be determined whether recoveries were corrected for apparent residues in controls.

The results of the storage stabili ty study are presented in Table C .2. The study results indicate that residues of propiconazole are stable under frozen storage conditions (-20 ± 5°C) for up to 24 months in/on sugar beet tops a nd root, barley grain, and apple, and for up to 30 months in/on soybean.

In the submission, stored sample recoveries were corrected vs. 0-day recoveries. For this DER, recoveries were corrected for fresh fortificati on recoveries. Either way, acceptable recoveries were obtained for all matrices at all storage intervals.

A graph of the storage stability of residues of propiconazole in sugar beet tops and roots, soybeans, barley grain and appl es is presented in Figure C.1.

TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole from Sugar Beet, Soybean, Barley and Apple Matrices. 1 Matrix Spike Level (ppm) Storage Interval 2

, days (months) Sample Size (n) Recoveries (%) Mean Recovery (%) Sugar beet tops 0.1 0 (0) 2 98, 95 96 0.1 91 (3.0) 2 103, 106 104 0.1 184 (6.1) 2 98, 98 98 0.1 365 (12.0) 2 96, 96 96 0.1 751 (24.7) 2 86, 86 86 Sugar beet root 0.1 0 (0) 2 95, 97 96 0.1 91 (3.0) 2 110, 109 110 0.1 184 (6.1) 2 97, 98 97 0.1 365 (12.0) 2 95, 92 94 0.1 751 (24.7) 2 99, 99 99 Soybean 0.1 0 (0) 2 96, 93 94 0.1 90 (3.0) 2 99, 105 102 0.1 183 (6.1) 2 95, 104 99 0.1 364 (12.0) 2 92, 94 93 0.1 750 (24.7) 2 92, 88 90 0.1 916 (30.1) 2 94, 78 86 Barley grain 0.1 0 (0) 2 98, 97 98 0.1 90 (3.0) 2 94, 92 93 0.1 183 (6.1) 2 104, 99 102 0.1 364 (12.0) 2 105, 96 101 0.1 750 (24.7) 2 86, 88 87Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.3/OPPTS 860.1380/OECD IIA 6.1.1 and IIIA 8.1.1 Storage Stability – Sugar beet tops and roots, soybean (seed), barley grain, and apple

DP# 400030/MRID No. 48681707 Page 5 of 6

TABLE C.1. Summary of Concurrent R ecoveries of Propiconazole from Sugar Beet, Soybean, Barley and Apple Matrices. 1 Matrix Spike Level (ppm) Storage Interval 2

, days (months) Sample Size (n) Recoveries (%) Mean Recovery (%) Apple 0.1 0 (0) 2 101, 98 99 0.1 90 (3.0) 2 107, 109 108 0.1 183 (6.1) 2 100, 94 97 0.1 364 (12.0) 2 89, 92 91 0.1 750 (24.7) 2 93, 90 92

1 All recovery values as reported by the petitioner.
2 Interval between fortification and extraction; extr acts were analyzed within 0-4 days of extraction.

TABLE C.2. Stability of Propiconazole Residues in Su gar Beet, Soybean, Barley and Apple Matrices Following Storage at -20 ± 5 °C. Commodity Spike Level (ppm) Storage Interval 1 , days (months) Recovered Residues (ppm) Mean Recovered Residues (ppm) Mean Recovery 2 (%) Corrected % recovery 3 Sugar beet tops 0.1 0 (0) 0.10, 0.09 0.10 95 -- 91 (3.0) 0.10, 0.11 0.10 105 101 184 (6.1) 0.11, 0.11 0.11 110 112 365 (12.0) 0.09, 0.10 0.09 95 99 751 (24.7) 0.08, 0.07 0.08 75 87 Sugar beet
root 0.1 0 (0) 0.09, 0.10 0.10 95 -- 91 (3.0) 0.11, 0.10 0.11 105 95 184 (6.1) 0.11, 0.10. 0.10 105 108 365 (12.0) 0.09, 0.09 0.09 90 96 751 (24.7) 0.09, 0.08 0.09 85 86 Soybean 0.1 0 (0) 0.10, 0.09 0.09 95 -- 90 (3.0) 0.10, 0.11 0.10 105 103 183 (6.1) 0.11, 0.11 0.11 110 111 364 (12.0) 0.09, 0.09 0.09 90 97 750 (24.7) 0.09, 0.09 0.09 90 100 916 (30.1) 0.09, 0.10 0.09 95 110 Barley grain 0.1 0 (0) 0.10, 0.10 0.10 100 -- 90 (3.0) 0.09, 0.09 0.09 90 97 183 (6.1) 0.11, 0.11 0.11 110 108 364 (12.0) 0.09, 0.10 0.10 95 94 750 (24.7) 0.08, 0.08 0.08 80 92 Apple 0.1 0 (0) 0.10, 0.10 0.10 100 90 (3.0) 0.10, 0.10 0.10 100 93 183 (6.1) 0.10, 0.10 0.10 100 103 364 (12.0) 0.09, 0.09 0.09 90 99 750 (24.7) 0.08, 0.08 0.08 80 87

1 Interval between fortification and extraction; extr acts were analyzed within 0-4 days of extraction.
2 Calculated by the study reviewer from reported recovered residue values.
3 Corrected for mean concurrent recovery by the study reviewer (See TABLE C.1.)Propiconazole/PC Code 122101/Syngenta Crop Protection, LLC DACO 7.3/OPPTS 860.1380/OECD IIA 6.1.1 and IIIA 8.1.1 Storage Stability – Sugar beet tops and roots, soybean (seed), barley grain, and apple

DP# 400030/MRID No. 48681707 Page 6 of 6 

### Figure C.1 Graph of Propiconazole St orage Stability in Plant Matrices

D. CONCLUSION

The storage stability data are ad equate and demonstrate that resi dues of propiconazole are stable in/on sugar beet tops and roots, barley grain, and apple stored frozen (-20 ± 5 °C) for up to 24 months, and in/on soybean stored frozen for up to 30 months in/on soybeans. An acceptable method was used for quantitation of propicona zole residues in the tested matrices.

E. REFERENCES

None.

F. DOCUMENT TRACKING

RDI: T. Morton(2/27/2013); S. Hummel (2/27/2013) Petition Number: 2F7975 DP Barcode(s): 400030 PC Code: 122101 80 85 90 95 100 105 110 115

0 10 20 30 40CorrectedRecovery%

Storage Interval (Months) 

### Storage Stability of Propiconazole in Plant Matrices

Sugar Beet Tops Sugar Beet Roots Soybean

Barle y Apple