UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

	OFFICE OF PREVENTION, PESTICIDE

	AND TOXIC SUBSTANCES

  SEQ CHAPTER \h \r 1 MEMORANDUM

Date:   June 12, 2009

SUBJECT:	Triticonazole.  Application for New Seed Treatment Uses on
Cereal Grains (Except Rice) (PP#8F7420).  Summary of Analytical
Chemistry and Residue Data.

PC Code:  125620	DP Barcodes:   325956, 353372, and 360624

Decision No.:  359614, 394309, 399232	Registration No.:  7969-xxx

Petition No.:  #8F7420	Regulatory Action:  Section 3 Registration

Risk Assessment Type:  NA	Case No.:  NA

TXR No.:  NA	CAS No.:  131983-72-7

MRID No.:  See MRID Summary Table	40 CFR:  §180.583

	Ver.Apr.08

FROM:	Amelia M. Acierto, Chemist

Risk Assessment Branch 3

Health Effects Division (7509P)

Through:	Stephen Funk, Senior Science Advisor

Risk Assessment Branch III

	                    Health Effects Division (7509P)

	To:	Shaja Joyner, RM #20

        Fungicide Branch

                    Registration Division (7505P)

	  SEQ CHAPTER \h \r 1

MRID Summary Table

MRID No.	Study Type	Comments

47511902	860.1340 Crops	New DER; 47511902.der.doc

45595401	860.1380 Wheat RACs and processed	New DER; 45595401.der.doc

46568301	860.1380 Triazoles	New DER; 46568301.der.doc

47470203	860.1500 Cereal grains	New DER; 47470203.der.doc

47511901	860.1520 Wheat, corn, rice, sorghum	New DER; 47511901.der.doc

47399201	860.1850 Lettuce, Radish and Wheat 	New DER; 47399201.der.doc

  SEQ CHAPTER \h \r 1 This document was originally prepared under
contract by Dynamac Corporation (1901 Research Boulevard, Suite 220;
Rockville, MD 20850).

The document has been reviewed by the Health Effects Division (HED) and
revised to reflect current Office of Pesticide Programs (OPP) policies.

Executive Summary

  SEQ CHAPTER \h \r 1 Triticonazole is a systemic triazole fungicide
that is currently registered for seed treatment on barley and wheat for
the control of various seed-borne diseases.  Triticonazole is formulated
as liquid flowable formulations.  The first food/feed use was requested
under PP#9F6051 in 2001 by Aventis Crop Science (EPA Company No. 264);
the Aventis products have since been transferred to BASF (EPA Company
No. 7969).

BASF Crop Protection has submitted a tolerance petition, PP#8F7420, and
Section 3 request to  register Triticonazole HL Fungicide (EPA Reg. No.
7969-xxx, a 4.17 lb ai/gal liquid flowable formulation) for seed
treatment uses on cereal grains (except rice) at a maximum rate of 0.05
lb ai/100 lb seed.  Concurrently, BASF has proposed the establishment of
permanent tolerances for residues of triticonazole in/on the following
crop groups:

	Grain, cereal, group 15 (except rice)	0.05 ppm

	Grain, cereal, forage, fodder and straw, group 16 (except rice)	0.10
ppm

Tolerances have been established under 40 CFR §180.583(a) for residues
of the fungicide triticonazole,
(1RS)-(E)-5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H
-1,2,4-triazol-1-ylmethyl)cyclopentanol, from the treatment of seed
prior to planting in/on barley grain, hay and straw, and wheat grain,
forage, hay and straw, each at 0.05 ppm.  There are no Codex or Mexican
MRLs established for residues of triticonazole.  Canadian MRLs are
established for triticonazole in/on barley, wheat, and oats, each at
0.01 ppm.

The nature of the residue in plant commodities is considered adequately
understood only for the purpose of the proposed/registered seed
treatment uses on cereal grain-type crops.  Based on the barley and
wheat metabolism studies, triticonazole is metabolized primarily via
hydroxylation of the dimethylcyclopentane moiety to form a series of
dihydroxy metabolites which subsequently cleave to form numerous minor
polar metabolites.  No triazole metabolites [1,2,4-triazole (T),
triazolylalanine (TA), or triazolylacetic acid (TAA)] were detected in
barley or wheat grain.  HED has previously determined that triticonazole
is the residue of concern in barley and wheat from seed treatment uses.
This determination may be extended to include seed treatment uses for
all crop commodities in the cereal grains crop group.

The nature of the residue in livestock commodities is considered
adequately understood only for the purpose of the proposed/registered
seed treatment uses on cereal grain-type crops, based on marginally
adequate dairy cattle and laying hen studies with phenyl-labeled
triticonazole only.  HED has previously deemed that triticonazole is the
residue of concern in ruminants and poultry from seed treatment uses on
barley and wheat.  This determination may again be extended to include
seed treatment uses for all crop commodities in the cereal grains crop
group.

The contribution of triazole derivatives [1,2,4-triazole,
triazolylalanine, and triazolylacetic acid] from the use of
triticonazole on barley and wheat to the aggregate exposure for human
health risk assessment has been previously considered (DP# 322215,
2/7/06, M. Doherty et al.).

An adequate LC/MS and LC/MS/MS method (Method 148.02) is available for
the enforcement of the proposed tolerances for triticonazole in cereal
grain matrices.  A similar method, LC/MS/MS method (Method 562/0), was
used for data collection in the cereal grain field trial and processing
studies.  The method was adequate for data collection based on
acceptable method verification and concurrent method recoveries.  The
validated LOQ was 0.01 ppm for triticonazole in/on all cereal grain crop
matrices.

The data requirements for testing with multiresidue methods have been
fulfilled.  Based on the results of the testing, the multiresidue
methods are not appropriate for determining triticonazole residues.

Livestock feeding studies, livestock tolerances, and livestock
enforcement methods are not required for the purpose of this petition.
Based on the recommended tolerances for triticonazole residues in
livestock feedstuffs, the maximum reasonable dietary burdens (MRDB) for
livestock were calculated at 0.089 ppm for beef cattle, 0.346 ppm for
dairy cattle, 0.038 ppm for poultry, and 0.042 ppm for swine.  The
results of the reviewed cow and poultry metabolism studies along with
the low levels of residues found in the cereal grain field trials
indicate that there is no reasonable expectation that quantifiable
residues of triticonazole will occur in livestock commodities [40 CFR
§180.6(a)(3)].  HED will re-examine this determination if additional
uses on livestock feedstuffs are proposed in the future.

Adequate data are available supporting the stability of triticonazole
residues during frozen storage of samples collected from the cereal
grain crop field trials and processing studies.  Adequate storage
stability data are also available for the triazole-related metabolites
(T, TA, and TAA) to support the storage conditions and durations of
wheat, corn, sorghum, and rice grain samples from the field studies, and
wheat flour and polished rice from the processing study.  The adequacy
of the additional triazole storage stability data to support the storage
durations of cereal grain forages, fodders and/or straws, corn kernel
plus cob with husk removed (K+CWHR), and sorghum stalks from the cereal
grain field trial studies will be determined when the final results of
an ongoing triazole storage stability study are submitted to the Agency.
 According to current Agency policy, storage stability in the raw
agricultural commodity (RAC) can be translated to the processed
commodity.

The submitted magnitude of the residue data are adequate to support the
requested seed treatment uses for cereal grain crops (except rice).
There are adequate data for the representative crops of the cereal grain
groups 15 and 16 to establish crop group tolerances.  The number and
locations of field trials were conducted according to the OPPTS 860.1500
guidelines.  The seed treatment rate (0.05 lb ai/100 lbs seed) used in
the field trials reflects the proposed use of  Triticonazole HL
Fungicide (EPA Reg. No. 7969-xxx) on barley, field corn and popcorn,
oats, rye, wheat, and triticale.  However, the rate reflects 5x and 2.5x
the proposed seed treatment rate for sweet corn and sorghum,
respectively.

Residues of triticonazole were below the LOQ of 0.01 ppm in treated
wheat grain, corn grain, corn K+CWHR, and sorghum grain.  Low but
quantifiable residues of triticonazole were observed in rice grain.  The
available data support a tolerance level of 0.01 ppm for cereal grains,
group 15 (except rice).  The value of 0.05 ppm proposed by the
petitioner is excessive, when rice is excluded.  Moreover, the 0.01 ppm
level harmonizes with Canada.  A revised Section F must be submitted to
reflect the tolerance recommendation of 0.01 ppm for cereal grains,
group 15 (except rice).  The individual tolerances established for
barley grain and wheat grain at 0.05 ppm in 40 CFR §180.583(a) should
be deleted when the crop group tolerance is established.

Residues of triticonazole were also nonquantifiable in treated field and
sweet corn forage and stover, and sorghum forage and stover.
Quantifiable residues of triticonazole were observed in treated wheat
forage, hay and straw, and rice straw.  Appropriate tolerance levels
were determined statistically (see Appendix I) according to Guidance for
Setting Pesticide Tolerances Based on Field Trial Data SOP.  The residue
data for rice straw was excluded from the spreadsheet because the
petitioner is not applying for use on rice.  The tolerance spreadsheet
calculated tolerances of 0.20 ppm for wheat forage, 0.25 ppm for wheat
hay, and 0.20 ppm for wheat straw.  HED recommends a crop group
tolerance of 0.25 ppm based on the highest calculated value for the
representative crop (wheat hay).

A revised Section F must be submitted to reflect the tolerance
recommendation of 0.25 ppm for the forage, fodder, and straw of cereal
grains, group 16 (except rice).  The individual tolerances established
for barley hay and straw, and wheat forage, hay and straw in 40 CFR
§180.583(a) should be deleted when the crop group tolerance is
established.

The processing data for field corn, rice, sweet sorghum, and wheat are
adequate.  The results indicate that residues of triticonazole were
nonquantifiable (<0.01 ppm) in the cereal grain RACs (corn, rice, wheat,
and sorghum) grown from seeds treated at 250 g triticonazole/100 kg seed
(5x the maximum proposed seed treatment rate).  Analysis of rice
processed matrices showed that residues of triticonazole may concentrate
in hulls (2.8x) but not significantly in bran (1.1x); residues in
polished rice were nonquantifiable.  As the petitioner is not seeking to
register use on rice at this time, no tolerances are required for rice
processed matrices.

The confined rotational crop study is acceptable.  The application rate
used in the study reflects 1.4x the equivalent per acre rate for cereal
grain crops.  The metabolism of triticonazole in rotated crops appears
similar to those observed for primary crops, except that
triazole-related metabolites were detected in the rotated crops.  The
data indicate that residues of triticonazole may be present at >0.01 ppm
in 30-DAT rotated lettuce (0.017 ppm), radish tops (0.049 ppm) and wheat
forage (0.041 ppm), straw (0.133 ppm) and chaff (0.139 ppm); 120-DAT
rotated radish tops (0.016 ppm), and wheat forage (0.019 ppm), straw
(0.150 ppm), and chaff (0.114 ppm); and 365-DAT rotated wheat forage
(0.025 ppm), straw (0.086 ppm) and chaff (0.133 ppm).  Wheat hay was not
analyzed but forage and straw were analyzed, and residues of
triticonazole were found in forage and straw.

The proposed label for the 4.17 lb/gal FS specifies that “planting of
any crop not listed on the label within 30 days after planting treated
seed is not allowed”.  The results of the submitted confined
rotational crop study do not support this restriction.  The data from
the confined rotational crop study indicate that triticonazole residues
greater than 0.01 ppm were detected at the 30-day PBI.  To support a
30-day plantback restriction on the label, limited field rotational crop
data for leafy vegetables, root and tuber vegetables, foliage of root
and tuber vegetables, and a cereal grain are required.  Until the
requested data are provided, the label must be modified to specify a
120-day (4-month) plantback restriction for leafy vegetables, a 365-day
(12-month) plantback restriction for root and tuber vegetables, and
prohibit the planting of all other crops not listed on the label.

Analytical standards for triticonazole are currently available in the
EPA National Pesticide Standards Repository.

  SEQ CHAPTER \h \r 1 Regulatory Recommendations and Residue Chemistry
Deficiencies

HED has examined the residue chemistry database for triticonazole and
concludes that pending submission of a revised Section B (see
requirements under Directions for Use) and a revised Section F (see
requirements under Proposed Tolerances), there are no residue chemistry
issues that would preclude granting conditional registration for the
requested seed treatment uses on cereal grain crops (except rice) and
the establishment of tolerances for residues of the fungicide
triticonazole,
(1RS)-(E)-5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H
-1,2,4-triazol-1-ylmethyl)cyclopentanol, from the treatment of seed
prior to planting in/on:

	Grain, cereal, group 15 (except rice)
………………………………...0.01 ppm

	Grain, cereal, forage, fodder, and straw, group 16 (except rice)
……0.25 ppm

Moreover, upon establishment of the above tolerances for grain, cereal,
group 15 (except rice) and grain, cereal, forage, fodder, and straw,
group 16 (except rice), the existing tolerances listed in 40 CFR 180 (a)
should be removed:  barley, grain; barley, hay; barley, straw; wheat,
forage; wheat, grain; wheat, hay; wheat, straw.

A human health risk assessment is forthcoming.

860.1200 Directions for Use

		•  The label for Triticonazole HL Fungicide must be amended to
include the following rotational crop restrictions:  a 120-day plantback
interval for leafy vegetables, a 365-day plantback interval root and
tuber vegetables, and prohibit the planting of all other crops not
listed on the label.

860.1550 Proposed Tolerances

	•  A revised Section F must be submitted to reflect the tolerance
recommendation of 0.01 ppm for cereal grains, group 15 (except rice); to
reflect the tolerance recommendation of 0.25 ppm for grain, cereal,
forage, fodder, and straw, group 16 (except rice); and to reflect the
correct commodity definitions as listed in Table 9.

HED recommends conversion of conditional registration to unconditional
registration for the cereal grains (except rice) upon adequate
resolution of data pertaining to storage stability and field
accumulation in rotational crops.

860.1380 Storage Stability

	•  To support the reported results for 1,2,4-triazole and the
triazole conjugates, the final report of the ongoing storage stability
study with free triazole and triazole conjugates in plant commodities
must be submitted.

860.1900 Field Accumulation in Rotational Crops

	•  Data from limited field accumulation studies on rotational crops
are required.

Background

The chemical structure and nomenclature of triticonazole and
triazole-related metabolites, and the physicochemical properties of the
technical grade of triticonazole are, respectively, presented in Tables
1 and 2.

Triazole acetic acid or triazolylacetic acid

Table 2.	Physicochemical Properties of Chemical:  Triticonazole.

Parameter	Value	Reference

Melting point/range	140 ºC; PAI displays two crystalline forms melting
at 137 and 141 ºC	BASF document number 2002/1016091 1

pH	Not available

	Density	1.21 g/mL (PAI)	BASF document number 2002/1016091 1

Water solubility	8.4 mg/L at 20 ºC

	Solvent solubility (at 20 ºC)	Hexane		0.12 g/L

Methanol	18.2 g/L

Acetone		74.5 g/L

Toluene		12.6 g/L

Dichloromethane	191 g/L

Ethyl acetate	48.6 g/L

n-Octanol	6.2 g/L

	Vapor pressure	<0.1 x 10-5 PA at 50 ºC

	Dissociation constant, pKa	Does not dissociate

	Octanol/water partition coefficient, Log(KOW)	Log P = 3.29 at 20 ºC

	UV/visible absorption spectrum	Not available

	1 As referenced in MRID 47470203.

860.1200 Directions for Use

A summary of the proposed use directions is presented in Table 3.
Information pertaining to the proposed use pattern was obtained from a
2008 specimen label submitted for Triticonazole HL Fungicide Seed
Treatment (4.17 lb/gal FS).  The EP is proposed for the control of
various seed-borne diseases in cereal crops except rice.

Table 3 shows that Triticonazole HL Fungicide Seed Treatment is proposed
for seed treatment on cereal grains (except rice) at a maximum rate of
0.05 lb ai/100 lb seed.  The end-use product Charter® Fungicide
Treatment (EPA Reg. No. 7969-386; accepted 6/27/2007) is currently
registered on barley and wheat for preplant seed treatment at a maximum
rate of 0.005 lb ai/100 lb seed.

Table 3.	Summary of Proposed Seed Treatment Use of Triticonazole.

Application Type	Formulation

[EPA Reg. No.]	Seed Treatment

Application Rate

(lb ai/100 lb seed)	Maximum

Seeding Rate 1

(lb seed planted/A)	Maximum Equivalent

Field Application Rate 2

(lb ai/A)

Barley

Seed Treatment	4.17 lb/gal FS

[7969-xxx]	0.005-0.050 	96	0.048

Field Corn and Popcorn (includes seed production)

Seed Treatment	4.17 lb/gal FS

[7969-xxx]	0.005-0.050 	15	0.008

Sweet Corn

Seed Treatment	4.17 lb/gal FS

[7969-xxx]	0.010	15	0.002

Oats

Seed Treatment	4.17 lb/gal FS

[7969-xxx]	0.005-0.050	128	0.064

Rye

Seed Treatment	4.17 lb/gal FS

[7969-xxx]	0.005-0.050	112	0.056

Sorghum

Seed Treatment	4.17 lb/gal FS

[7969-xxx]	0.010-0.020	10	0.002

Wheat and Triticale

Seed Treatment	4.17 lb/gal FS

[7969-xxx]	0.005-0.050	150	0.075

General Use Directions and Limitations:  To be applied as a water-based
mixture using standard or mist-type seed treatment application
equipment.  A colorant must be added to identify the treated seed.  The
proposed label does not include water amounts needed to provide the
mixture or slurry rate for optimum coverage, but recommends consulting a
seed-treatment specialist.  The product may be tank-mixed with other
water-based seed treatments.  Use of treated seed for food, feed, or oil
processing is prohibited.  Planting of any crop not listed on the label
within 30 days after planting treated seed is not allowed.

1  From Science Advisory Council for Exposure, Standard Operating
Procedure, SOP #15, 3/2/04.

2  Calculated by the study reviewer using the maximum seed treatment
rate and maximum seeding rate.

Conclusions.  The submitted label for Triticonazole HL Fungicide Seed
Treatment is adequate to allow evaluation of the residue data relative
to the proposed use.  However, the proposed 30-day plantback interval
for all crops not listed on the label is not acceptable.  The submitted
confined rotational crop study, which was conducted at 1.4x the proposed
maximum equivalent field application rate for cereal grains, indicates
that residues of triticonazole may be present at >0.01 ppm in 30-DAT
rotated lettuce, radish tops and wheat forage, straw and chaff; 120-DAT
rotated radish tops, and wheat forage, straw, and chaff; and 365-DAT
rotated wheat forage, straw and chaff.

The label for Triticonazole HL Fungicide must be amended to include the
following rotational crop restrictions: a 120-day plantback interval for
leafy vegetables, a 365-day plantback interval for root and tuber
vegetables, and prohibit the planting of all other crops not listed on
the label.  Data from limited field accumulation studies on rotational
crops are required.

860.1300 Nature of the Residue - Plants

Residue Chemistry Memo DP# 262566, 6/6/2001, N. Dodd (PP#9F6051)

  SEQ CHAPTER \h \r 1 Field and greenhouse studies were previously
submitted investigating the metabolism of [triazole- 14C]- and
[phenyl-14C]-triticonazole in spring and winter wheat and barley.    SEQ
CHAPTER \h \r 1 In the initial greenhouse study and two field studies
(wheat and barley seeds treated with [triazole- 14C]triticonazole), the
total radioactive residues (TRRs) were determined, but samples were
either not extracted or the characterization of extracted 14C-residues
was very limited.  The most complete analyses were conducted in two
field studies:  (i) with [triazole-14C]triticonazole at 187 g ai/100 kg
seed (3.7x the maximum proposed seed treatment use of 50 g ai/100 kg
seed) in wheat and 299 g ai/100 kg seed (6x) in barley; and (ii) with
[phenyl-14C]triticonazole at 155 g ai/100 kg seed (3.1x) in wheat and
242 g ai/100 kg seed (4.8x) in barley.  In these studies, the
14C-residues in RAC samples were identified as parent, one of the
dihydroxy metabolites (RPA 404766, RPA 404886, RPA 406341, RPA 406780),
the Z isomer of parent (RPA 406203), or characterized as minor unknowns
(each <10% TRR) that were generally polar in nature.  However,
extraction of various samples in these studies was incomplete as
residual solids accounted for >10% of the TRR and >0.05 ppm.

As determined in the [triazole-14C]-triticonazole metabolism study, no
triazole, triazolylalanine, or triazolylacetic acid were detected in
wheat and barley grain.  These are metabolites of some triazole
fungicides, for which free triazole may be of toxicological concern.
The petitioner has been advised that in future plant metabolism studies,
which may be conducted to reflect future application methods (i.e.,
foliar or soil application), the petitioner should also look for
triazole pyruvate.

The metabolism of triticonazole in wheat and barley was considered
adequately understood for the purposes of the use of triticonazole as a
seed treatment on cereal grains.  Based on the available wheat and
barley metabolism data, triticonazole is metabolized in wheat and barley
primarily via hydroxylation of the dimethylcyclopentane moiety to form a
series of dihydroxy metabolites.  The residues which were identified
were parent, RPA 404766, RPA 404886, RPA 406341, RPA 406780, and the Z
isomer of the parent (RPA 406203).  Subsequent cleavage of the dihydroxy
metabolites results in the formation of numerous minor (<10% TRR)
metabolites that are generally more polar in nature.  HED’s Metabolism
Assessment Review Committee determined on 5/1/01 that triticonazole per
se is the residue of concern in wheat and barley for seed treatment
uses.  The available metabolism studies supporting seed treatment uses
on barley and wheat may be extended to include seed treatment uses on
all crop commodities in the cereal grains crop group.

860.1300 Nature of the Residue - Livestock

Residue Chemistry Memo DP# 262566, 6/6/2001, N. Dodd (PP#9F6051)

≤0.001 ppm in milk and nondetectable (<0.004 ppm) in muscle and fat at
the 10 ppm dosing level.

A poultry metabolism study was conducted on laying hens using
[U-phenyl-14C]-triticonazole at dosing levels of ~1 ppm (125x the MRBD
for poultry) and ~10 ppm (1250x) for 14 consecutive days.  Detectable
radioactive residues were found in whole eggs, liver, high-dose muscle,
high-dose skin with fat, and high-dose peritoneal fat.  Residues
identified by HPLC in high-dose eggs were parent, RPA 404886, RPA
404766, RPA 406780, RPA 406972, and RPA 406341.  Residues identified by
HPLC in high-dose liver were parent, RPA 404886, and RPA 406972.
Residues identified in peritoneal fat by TLC subsequent to HPLC were
parent, RPA 406341, and RPA 404886.  Residues in poultry muscle were not
identified because of low radioactivity.

The metabolism of triticonazole in ruminants and poultry is considered
adequately understood for the purposes of uses of triticonazole as a
seed treatment on cereal grains.  The HED Metabolism Assessment Review
Committee determined on 5/1/01 that triticonazole is the residue of
concern in livestock for seed treatment uses on barley and wheat.  The
available metabolism studies supporting seed treatment uses on barley
and wheat may be extended to include seed treatment uses on all crop
commodities in the cereal grains crop group.

  SEQ CHAPTER \h \r 1 For future uses other than seed treatment uses,
ruminant and poultry metabolism studies with the 14C label in the
triazole ring will be needed in addition to new phenyl-labeled ruminant
and poultry metabolism studies required because of multiple deficiencies
regarding the submitted phenyl-labeled studies.

860.1340 Residue Analytical Methods

Enforcement method

Residue Chemistry Memo DP# 262566, 6/6/2001, N. Dodd (PP#9F6051)

In conjunction with a previous triticonazole petition (PP#9F6051) for
seed treatment uses on barley and wheat, HED has determined that the
SEQ CHAPTER \h \r 1 LC/MS and LC/MS/MS methods (Aventis Method MS
148.02) are suitable for enforcing tolerances for residues of
triticonazole and two of its dihydroxy metabolites RPA 404886 and RPA
406341.  The method measures each analyte individually in/on wheat and
barley RACs and processed commodities.  Using this method, residues are
extracted with water:acetone.  No hydrolysis step is included to release
conjugate residues.  The reported LOQ for the LC/MS/MS method was 0.002
ppm for all three analytes in forage, straw and grain.  A successful
independent laboratory validation has been conducted for Aventis Method
MS 148.02 on wheat forage.

HED concludes that Aventis Method MS 148.02 would also be adequate for
the enforcement of recommended tolerances addressed in this document.
For future uses other than seed treatment, additional data regarding the
analytical method must be addressed (see DP# 262566, 6/6/2001, N. Dodd).

Data-Collection Method

DER Reference:  47511902.der.doc

Samples of RACs (wheat forage, hay, straw and grain; field corn, forage,
grain and stover; sweet corn forage, K+CWHR, and stover; sorghum forage,
grain, and stover; and rice grain and straw) and processed (wheat bran
and flour; corn oil and starch; and rice hulls, bran and polished rice)
commodities were analyzed for residues of triticonazole using LC/MS/MS
Method 562/0.  The data-collection method is similar to the enforcement
method discussed above.  Method 562/0 method was modified for analysis
of cereal grain matrices to eliminate the clean-up step which was not
needed because no matrix interference occurred.

 ion transitions (318.0→70.0 and 318.0→125.0).  Average recoveries
were within the acceptable range of 70-120% and RSDs were <20% for
triticonazole in all tested matrices.  The fortification levels used in
method validation are adequate to bracket expected residue levels in
cereal grain matrices from the associated field trials.  Confirmatory
analysis may be performed using the second daughter ion transition.

 70.1 → 43.2 for T, m/z 128.1 → 70.2 for TAA, and m/z 157.1 → 88.1
for TA.  In the field trials, the validated LOQ was 0.05 ppm each for T,
TA, and TAA in all cereal grain matrices, except for T and TAA in grain
and K+CWHR, which had LOQs of 0.01 ppm each.  In the processing studies,
the validated LOQ was 0.01 ppm each for T and TAA, and 0.05 ppm for TA
in cereal grain matrices.

The above LC/MS/MS methods (562/0 for triticonazole; D0508 and D0604 for
triazoles) were adequately validated in conjunction with the analysis of
field trial and processing samples using untreated samples of each
commodity fortified with the appropriate analytes at levels bracketing
the residues found in the treated samples.  The petitioner reported that
because triazole-related compounds are commonly found in plants in
nature, two untreated controls were used to establish the background
apparent residues in controls for each analytical set.

Samples from a wheat storage stability study were analyzed for residues
of triticonazole and its metabolites RPA 406341 and RPA 404886 using the
enforcement method LC/MS Method 148.02 (revision 2) entitled “Method
of Analysis for the Determination of RPA 400727 (Triticonazole) and its
Metabolites RPA 404886 and RPA 406341 in Wheat and Barley Matrices by
LC/MS.”  The validated LOQ based on method verification data was 0.05
ppm for each analyte in all wheat matrices.  Briefly, forage, hay,
straw, germ, and bran samples were soaked overnight in acetone, and
extracted twice again with water:acetone (1:9, v:v).  The concentrated
extract was mixed with ACN and diluted with water for clean-up through a
C18 solid phase extraction (SPE) cartridge; residues were eluted with 5%
methanol in ACN.  The eluate was evaporated to just dryness and
reconstituted in ACN:water (1:1, v:v) for LC/MS analysis.

Grain and flour samples were soaked overnight in water:acetone (9:1,
v:v) and extracted twice again with acetone.  The concentrated extract
was mixed with a small amount of acetone, and water with sodium chloride
for partitioning with DCM.  Partitioning with DCM was repeated twice.
The DCM phases were combined, evaporated to just dryness and
reconstituted in ACN:water (1:1, v:v) for LC/MS analysis.

The method was adequately validated prior to and in conjunction with the
analysis of the stored samples.  Concurrent recoveries were generally
within the acceptable range of 70-120% for triticonazole and the two
metabolites in all wheat commodities fortified with each analyte at 0.50
ppm.  Acceptable method verification recoveries were also obtained for
triticonazole residues in wheat matrices fortified at 0.05 and 0.50 ppm.

Conclusions.  The LC/MS/MS method, 562/0, is adequate for collecting
data on residues of triticonazole in/on cereal grain RACs (wheat forage,
hay, straw and grain; field corn, forage, grain and stover; sweet corn
forage, K+CWHR, and stover; sorghum forage, grain, and stover; and rice
grain and straw) and processed (wheat bran and flour; corn oil and
starch; and rice hulls, bran and polished rice) commodities.  The
LC/MS/MS methods, Methods D0508 and D0604, are adequate for collecting
data on residues of 1,2,4-triazole, TA and TAA in/on cereal grain
matrices.

The previously submitted LC/MS and LC/MS/MS methods (Aventis Method MS
148.02) would also be suitable for enforcing the recommended tolerances.
 As noted under PP#9F6051, for future uses other than seed treatment,
additional data regarding the analytical method must be addressed.

No methods have been submitted or are required for analysis of
triticonazole residues in livestock commodities.  The proposed seed
treatment use on cereal grain crops falls under 40 CFR §180.6(a)(3).

860.1360 Multiresidue Methods

Residue Chemistry Memo DP# 262566, 6/6/2001, N. Dodd (PP#9F6051)

Multiresidue method testing data were previously submitted for
triticonazole, RPA 406341, and RPA 404886.  The multiresidue methods are
not adequate for enforcement since recoveries were obtained only with
Protocol D, and the recoveries were not adequate.  These data were
forwarded to FDA.

860.1380 Storage Stability

Storage Stability Study with Triticonazole on Wheat

DER Reference: 45595401.der.doc

Residue Chemistry Memo DP# 262566, 6/6/2001, N. Dodd (PP#9F6051)

BASF has submitted the final report of a storage stability study with
triticonazole on wheat.  Interim data up to 12 months were previously
reviewed in connection with a tolerance petition for wheat and barley
(PP#9F6051; DP# 262566, 6/6/2001, N. Dodd).  The final study report
reflects a maximum storage interval of 18 months and was required as a
condition of registration under PP#9F6051.  Samples of untreated wheat
grain, forage, straw, hay and processed bran, flour and germ were
fortified with triticonazole or its metabolites RPA 406341 and RPA
404886 at 0.5 ppm each analyte, except for months 1 through 18 where RPA
404886 was fortified at 0.28 ppm in all matrices.  Samples were stored
frozen (-20 ºC) for up to 18 months.  Actual storage intervals tested
were 0, 1, 3, 6, 9, 12, 15, and 18 months.

Wheat samples were analyzed for residues of triticonazole and its
metabolites RPA 406341 and RPA 404886 using LC/MS Method 148.02
(revision 2), entitled “Method of Analysis for the Determination of
RPA 400727 (Triticonazole) and its Metabolites RPA 404886 and RPA 406341
in Wheat and Barley Matrices by LC/MS.”  Samples were analyzed by
Enviro-Test Laboratories (Edmonton, Alberta, Canada).  The method was
adequate for data collection based on acceptable concurrent method
recoveries; the validated LOQ based on method verification data was 0.05
ppm for each analyte in all wheat matrices.

The final study results indicate that residues of triticonazole and its
metabolites RPA 406341 and RPA 404886 were relatively stable in/on the
raw agricultural commodities of wheat (forage, hay, grain, and straw) as
well as in its processed commodities (germ, flour, and bran) when stored
frozen (-20 ºC) for up to 18 months.

Interim Results of a Storage Stability Data Study with 1,2,4-Triazole
(T), Triazolylalanine (TA), and Triazolylacetic Acid (TAA) In Apples,
Wheat Flour, Peanut Butter, Milk, and Eggs

DER Reference: 	46568301.der.doc

The U.S. Triazole Task Force has submitted the interim results of an
ongoing storage stability study with 1,2,4-triazole (T),
triazolylalanine (TA) and triazolylacetic acid (TAA) in selected crop
and animal matrices (apples, wheat flour, peanut butter, milk, and
eggs).  The study submission reported that when completed, the final
study report will include analysis of additional samples for up to a
two-year time point.  Homogenized samples of apples, eggs, and milk were
spiked with T at 0.20 ppm, or a mixture of TA and TAA at 0.20 ppm for
each analyte.  Samples of homogenized wheat flour and peanut butter were
spiked with T at 0.20 ppm, or TA and TAA at 1.0 ppm for each analyte.
The fortification level used for peanut butter cannot be confirmed;
therefore, raw data are required in the final study report to confirm
the actual fortification levels.  Fortified and unfortified samples were
stored frozen (≤-20 ºC) and analyzed following 0, 1, 3, 6, and 12
months of storage.

Samples were analyzed for residues of T, TA, and TAA using LC/MS/MS
Method Meth-160 (Pyxant Labs Inc. Method Addendum Revision #2).
Adequate concurrent method recovery data were provided to confirm that
LC/MS/MS Method Meth-160 is adequate for data collection.  The validated
LOQs were 0.010 ppm for each analyte in apples; 0.010 ppm each for TA
and TAA, 0.005 ppm for T in milk; and 0.010 ppm for T and 0.030 ppm each
for TA and TAA in wheat flour.

The interim data suggest that residues of T, TA and TAA are reasonably
stable when stored frozen for up to one year in/on apples, wheat flour,
peanut butter, milk, and eggs.  The Task Force noted that the protocol
specified that peanut butter be stored refrigerated (<10 ºC) for the
storage stability study to support the USTTF and USDA PDP (Pesticide
Data Program) monitoring studies.  In a deviation from the protocol,
peanut butter samples were instead stored frozen (<-20 ºC).  The peanut
butter storage stability testing is planned to be repeated with samples
stored refrigerated.

Other Storage Stability Data

Interim storage stability data for T, TA, and TAA in canola seed, turnip
roots, mustard greens, and wheat straw, grain, and forage were
previously referenced in association with a prothioconazole petition
(PP#4F6830; DP#s 303508 & 314517, S. Funk, 8/21/2006).  The final report
on the storage stability study with the triazoles which are required as
confirmatory data; that may support the storage conditions and durations
of wheat, corn, sorghum, and rice foliage matrices and corn K+CWHR have
been received and is being reviewed separately.

Sample storage conditions and intervals

Table 4 lists the information pertaining to the storage conditions and
intervals of samples incurred in the current field trial and processing
studies.

Table 4.	Summary of Storage Conditions and Durations of Samples from
Crop Field Trial and Processing Studies.

Matrix 	Storage

Temp. (°C)	Actual Storage

Duration	Interval of Demonstrated

Storage Stability

Triticonazole

Wheat forage	<-5	224-323 days (7.4-10.6 months)	Residues of
triticonazole are relatively stable in/on wheat forage, hay, straw and
grain stored frozen for up to 18 months.

Wheat hay

200-295 days (6.6-9.7 months)

	Wheat grain

175-261 days (5.8-8.6 months)

	Wheat straw

173-265 days (5.7-8.7 months)

	Corn forage

124-256 days (4.1-8.4 months)

	Corn grain

106-184 days (3.5-6.1 months)

	Corn stover

109-342 days (3.6-11.3 months)

	Corn K+CWHR

105-258 days (3.5-8.5 months)

	Sorghum forage

142-247 days (4.7-8.1 months)

	Sorghum grain

109-158 days (3.6-5.2 months)

	Sorghum stover

112-161 days (3.7-5.3 months)

	Rice grain

97-226 days (3.2-7.4 months)

	Rice straw

106-182 days (3.5-6.0 months)

	Corn, grain

(for processing)	<-5	120 days (3.9 months)	18 months in wheat grain

Rice, grain

(for processing)

131-203 days (4.3-6.7 months)	18 months in wheat grain

Rice, polished

131-203 days (4.3-6.7 months)	18 months in wheat grain

Rice, hulls

30 days (1.0 month)	None required

Rice, bran

30-47 days (1.0-1.5 months)	18 months in wheat bran

Sorghum, stalk

(for processing)

154 days (5.1 months)	18 months in wheat grain and forage

Wheat, grain

(for processing)

173 days (5.7 months)	18 months in wheat grain

Triazoles

Wheat grain	<-5	185-309 days (6.1-10.2 months)	Residues of T, TA, and
TAA are relatively stable in wheat flour (and apple, peanut butter, milk
and eggs) stored frozen for up to 12 months).

Corn grain

114-192 days (3.8-6.3 months)

	Sorghum grain

107-155 days (3.5-5.1 months)

	Rice grain

102-177 days (3.4-5.8 months)

	Corn K+CWHR

96-249 days (3.2-8.2 months)	Awaiting final report

Wheat forage

229-323 days (7.5-10.6 months)

	Wheat hay

217-310 days (7.1-10.2 months)

	Wheat straw

182-267 days (6.0-8.8 months)

	Corn forage

119-250 days (3.9-8.2 months)

	Corn stover

99-332 days (3.3-10.9 months)

	Sorghum forage

145-250 days (4.8-8.2 months)

	Sorghum stover

119-167 days (3.9-5.5 months)

	Rice straw

107-183 days (3.5-6.0 months)

	Corn, grain

(for processing)	<-5	142-206 days (4.7-6.8 months)	12 months in wheat
flour

Corn, grits

70-71 days (2.3 months) 	None available*

Corn, flour

70-71 days (2.3 months)	12 months in wheat flour

Corn, oil

11-12 days (0.4 months)	None required

Corn, meal

70-71 days (2.3 months)	None available*

Corn, starch

8-9 days (0.3 months)	None required

Rice, grain

(for processing)	<-5	154-210 days (5.1-6.9 months)	12 months in wheat
flour

Rice, polished

28-37 days (0.9-1.2 months)	12 months in wheat flour

Rice, hulls

28-40 days (0.9-1.3 months)	None available*

Rice, bran

28-31 days (0.9-1.0 months)	None required

Sorghum, stalk

(for processing)

177-178 days (5.8-5.9 months)	Awaiting final report

Sorghum, syrup

21 days (0.7 months)	None required

Wheat, grain

292-315 days (9.6-10.4 months)	12 months in wheat flour

Wheat, bran

54-62 days (1.8-2.0 months)	None available*

Wheat, flour

53-57 days (1.7-1.9 months)	12 months in wheat flour

Wheat, middlings

55-56 days (1.8 months)	None available*

Wheat, shorts

55-56 days (1.8 months)	None available*

Wheat, germ

55-68 days (1.8-2.2 months)	None available*

*According to current HED policy, storage stability in the raw
agricultural commodity can be translated to the processed commodity.

 Conclusions.  The available storage stability data for triticonazole
residues in wheat matrices are adequate and may be translated to the
other cereal grains (corn, sorghum, and rice) to support the storage
durations and conditions of samples from the submitted field and
processing studies.

The interim storage stability data submitted by the U.S. Triazole Task
Force for the triazole-related metabolites suggest that residues of T,
TA and TAA are reasonably stable when stored frozen for up to one year
in/on apples, wheat flour, peanut butter, milk, and eggs.  The data for
wheat flour may be translated to wheat, corn, sorghum, and rice grain
samples from the field and processing studies, and to corn and wheat
flour and polished rice from the processing study.

The adequacy of the additional triazole storage stability data to
support the storage durations of cereal grain forages, fodders and/or
straws, corn K+CWHR, and sorghum stalks from the cereal grain field
trial will be determined when the final results of the ongoing triazole
storage stability study are submitted to the Agency.  Supporting storage
stability data for triazole residues are not required for corn oil and
starch; rice bran; and sorghum syrup as these matrices were analyzed
within 30 days of processing.  However, no additional supporting freezer
storage stability data are required for T, TA, and TAA in rice hulls,
corn grits and meal, and wheat bran, middlings, shorts, and germ since,
according to current Agency policy, storage stability in the raw
agricultural commodity (RAC) can be translated to the processed
commodity.

860.1400 Water, Fish, and Irrigated Crops

There are no proposed uses relevant to this guideline topic.  The
petitioner noted that they are not seeking to register use on rice, a
crop which may be irrigated, at this time.

860.1460 Food Handling

There are no proposed uses that are relevant to this guideline topic.

860.1480 Meat, Milk, Poultry, and Eggs

Residue Chemistry Memo DP# 262566, 6/6/2001, N. Dodd (PP#9F6051)

The maximum theoretical dietary burdens (MTDB) for livestock were
previously calculated as 0.09 ppm for beef cattle, 0.14 ppm for dairy
cattle, and 0.05 ppm for poultry and swine, based on barley and wheat
seed treatment uses (PP#9F6051).    SEQ CHAPTER \h \r 1 No tolerances
were established for residues of triticonazole in livestock commodities.

Based upon the proposed seed treatment uses on additional cereal grain
crops and the recommended tolerances for triticonazole residues in/on
livestock feedstuffs, the maximum reasonable dietary burdens (MRDB) for
livestock are 0.089 ppm for beef cattle, 0.346 ppm for dairy cattle,
0.038 ppm for poultry, and 0.042 ppm for swine (see Table 5 below).

Table 5.	Calculation of Dietary Burdens of Triticonazole Residues to
Livestock.

Feedstuff	Type1	% Dry Matter2	% Diet2	Recommended Tolerance (ppm)
Dietary Contribution (ppm)3

Beef Cattle

Wheat, hay	R	88	15	0.25	0.043

Sorghum, grain	CC	86	40	0.05	0.023

Wheat milled bypdts	CC	88	40	0.05	0.023

Untreated PC	PC	--	5	--	0

TOTAL BURDEN	--	--	100	--	0.089

Dairy Cattle

Oat, forage	R	30	30	0.20	0.200

Wheat, forage	R	25	15	0.20	0.120

Sorghum, grain	CC	86	45	0.05	0.026

Untreated PC	PC	--	10	--	0

TOTAL BURDEN	--	--	100	--	0.346

Poultry

Wheat, grain	CC	89	75	0.05	0.038

Untreated PC	PC	--	25	--	0

TOTAL BURDEN	--	--	100	--	0.038

Swine

Corn, field, grain	CC	88	85	0.05	0.042

Untreated PC	PC	--	15	--	0

TOTAL BURDEN	--	--	100	--	0.042

1  R:  Roughage; CC:  Carbohydrate concentrate; PC:  Protein
concentrate.

2  OPPTS 860.1000 Table 1 Feedstuffs (June 2008).

3  Contribution = ([tolerance /% DM] X % diet) for beef and dairy
cattle; contribution = ([tolerance] X % diet) for poultry and swine.

Ruminant and poultry feeding studies have not been submitted, and none
are required at this time.  Based on the available cow and poultry
metabolism studies, and low levels of residues found in the cereal grain
(corn, rice, sorghum and wheat) field trials, there is no reasonable
expectation that quantifiable residues of triticonazole will occur in
livestock commodities [40 CFR §180.6(a)(3)].  Therefore, livestock
feeding studies and tolerances are not required at this time.  If the
use of triticonazole is expanded to include uses other than seed
treatments or additional livestock feed items, the need for feeding
studies will be re-evaluated.

860.1500 Crop Field Trials

DER Reference:  47470203.der.doc

HED had previously reviewed magnitude of the residue data (PP#9F6051;
DP# 262566, 6/6/2001, N. Dodd) for triticonazole and its metabolites RPA
406341 and RPA 404886 in/on barley and wheat following preplant seed
treatment.  BASF Crop Protection is now seeking the registration of
Triticonazole HL Fungicide (EPA Reg. No. 7969-xxx) for preplant seed
treatment uses on cereal grain crops (except rice).  The supporting
magnitude of the residue study (MRID 47470203) has been reviewed, and
the Executive Summary of the Data Evaluation Record is reproduced below.

BASF has submitted field trial data for triticonazole on corn (field and
sweet), rice, sorghum, and wheat, the representative crops of the cereal
grain crop groups 15 and 16.  A total of 58 field trials was conducted
in the United States and Canada during the 2006-2007 growing season.
Fifteen wheat trials were conducted in Zones 2 (GA; 1 trial), 4 (AR; 1
trial), 5 (KS, ND, MN; 3 trials), 6 (TX; 1 trial), 7 (ND, NE, SD; 4
trials), 8 (OK, TX; 4 trials), and 11 (WA; 1 trial).  Fifteen field corn
trials were conducted in Zones 1 (PA; 1 trial), 2 (GA; 1 trial), 5 (IA,
IL, IN, KS, MB, MN, ND, SD, WI; 12 trials), and 6 (TX; 1 trial).  Four
sweet corn trials were conducted in Zones 3 (FL; 1 trial), 10 (CA; 1
trial), 11 (ID, 1 trial), and 12 (BC; 1 trial).  Twelve grain sorghum
trials were conducted in Zones 2 (GA; 1 trial), 4 (AR; 1 trial), 5 (IA,
IL, KS and MN; 4 trials), 6 (OK, TX; 2 trials), 7 (NE; 1 trial), and 8
(TX; 3 trials).  Finally, twelve rice trials were conducted in Zones 4
(AR, MS, LA; 7 trials), 5 (MO; 1 trial), 6 (TX; 2 trials), and 10 (CA; 2
trials).

At each test location, the crops were grown from seeds treated with a
4.2 lb/gal flowable liquid formulation of triticonazole, prior to
planting, at 50 g ai/100 kg seed (0.05 lb ai/100 lb seed; 1x the maximum
proposed seed treatment use on cereal grain crops).  The triticonazole
formulation was mixed with Apron XL (mefenoxam; a seed fungicide) and
colorant.  A separate plot (untreated) was planted with seed treated
with Apron XL and colorant only.  The applications made to sorghum seed
also included pyraclostrobin, and sorghum plants were also foliarly
treated with pyraclostrobin; these pyraclostrobin data are not reviewed
herein.

The cereal RAC samples were collected at normal harvest.  Wheat forage
was collected at the 6-8 inch stage to stem elongation (jointing) stage.
 Wheat hay was harvested at the early flower (boot) to soft dough stage
and allowed to field dry for 1-8 days prior to collection.  Wheat grain
and straw were harvested at maturity.  Sorghum forage was harvested at
the soft dough to hard dough stage, and grain and stover were harvested
at maturity.  Rice grain (kernel plus hull) and straw were also
harvested at maturity.

At the field trials planted with sweet corn varieties, corn kernel and
cobs with husks removed (K+CWHR) were collected at commercial maturity.
Forage was collected prior to the harvest of K+CWHR, and stover was
collected at maturity following collection of K+CWHR.  Additional fresh
corn samples were harvested at the milk stage from 5 of the field corn
sites to represent K+CWHR samples.  Corn forage was harvested at the
late dough/early dent stage from the field corn trials.  Corn grain and
stover from the field corn trials were harvested at maturity.

All samples were analyzed for triticonazole using LC/MS/MS Method 562/0.
 The method is adequate for data collection and was validated using
wheat forage, hay, grain and straw; corn forage, K+CWHR, grain and
stover; sorghum forage, grain, and stover; and rice grain and straw.
The validated method LOQ was 0.01 ppm in/on all tested cereal grain
RACs.

 Samples were also analyzed for the triazole-related metabolites,
triazole (T), triazolylacetic acid (TAA), and triazolylalanine (TA)
using LC/MS/MS Methods D0508 and D0604 (grain).  The validated method
LOQ was 0.05 ppm for each analyte in all cereal RACs, except for T and
TAA in grain and K+CWHR, which had LOQs of 0.01 ppm each.

Prior to the analysis for triticonazole residues, samples were stored
frozen for maximum durations of 10.6 months for wheat forage, hay, grain
and straw, 11.3 months for corn, forage, grain, stover and K+CWHR, 8.1
months for sorghum forage, grain and stover, and 7.4 months for rice
grain and straw.  Adequate storage stability data are available for
wheat matrices which may be translated to corn, sorghum and rice
matrices, and will support the storage conditions and durations of
samples from the cereal grain field trials.

Prior to the analysis for triazole residues, samples were stored frozen
for maximum durations of 8.8-10.6 months for wheat forage, hay, grain
and straw, 6.3-10.9 months for corn, forage, grain, stover and K+CWHR,
5.1-8.2 months for sorghum forage, grain and stover, and 5.8-6.0 months
for rice grain and straw.  Storage stability of the triazole-related
metabolites (T, TA, and TAA) has been demonstrated in apple, wheat
flour, peanut butter, milk, and eggs stored frozen for up to 12 months.
Because T, TA, and TAA appear reasonably stable, data for wheat flour
may tentatively be translated to support the storage conditions and
durations of wheat, corn, sorghum, and rice grain samples from the
subject field trials.  The stability confirmation will be assessed when
the final report of an ongoing study investigating the storage stability
of T, TA and TAA in canola seed, turnip roots, mustard greens, and wheat
straw, grain, and forage is submitted and reviewed

The results of the field trials are summarized below in Table 6.

Table 6.   Summary of Residue Data from Crop Field Trials with
Triticonazole.

Commodity	Applic.

Rate

(g ai/100

 kg seed)	DAP (days)	Residue Levels (ppm)1

	n	Min.	Max.	HAFT2	Median

(STMdR)	Mean

(STMR)	Std.

 Dev. 3

Proposed Rate on Barley, Corn (Field and Pop), Oats, Rye, Wheat, and
Triticale =  0.050 lb ai/100 lb seed

Proposed Rate on Sweet Corn = 0.010 lb ai/100 lb seed

Proposed Rate on Sorghum = 0.020 lb ai/100 lb seed)

Triticonazole

Wheat, forage	50	35-102	30	<0.01	0.10	0.10	0.02	0.04	0.028

Wheat, hay	50	56-135	30	<0.01	0.08	0.08	0.02	0.03	0.026

Wheat, grain	50	90-177	30	<0.01	<0.01	<0.01	0.01	0.01	NA

Wheat, straw	50	90-177	30	<0.01	0.08	0.08	0.03	0.03	0.024

Corn, forage 4	50	78-155	38	<0.01	<0.01	<0.01	0.01	0.01	NA

Corn, grain	50	112-161	30	<0.01	<0.01	<0.01	0.01	0.01	NA

Corn, stover 4	50	92-176	38	<0.01	<0.01	<0.01	0.01	0.01	NA

Corn, K+CWHR	50	71-114	18	<0.01	<0.01	<0.01	0.01	0.01	NA

Sorghum, forage	50	61-113	24	<0.01	<0.01	<0.01	0.01	0.01	NA

Sorghum, grain	50	90-199	24	<0.01	<0.01	<0.01	0.01	0.01	NA

Sorghum, stover	50	90-199	24	<0.01	<0.01	<0.01	0.01	0.01	NA

Rice, grain	50	114-182	24	<0.01	0.02	0.02	0.01	0.01	0.003

Rice, straw	50	114-182	24	<0.01	0.04	0.04	0.01	0.02	0.009

Triazole (T)

Wheat, forage	50	35-102	30	<0.05	<0.05	<0.05	0.05	0.05	NA

Wheat, hay	50	56-135	30	<0.05	<0.05	<0.05	0.05	0.05	NA

Wheat, grain	50	90-177	30	<0.01	<0.01	<0.01	0.01	0.01	NA

Wheat, straw	50	90-177	30	<0.05	<0.05	<0.05	0.05	0.05	NA

Corn, forage 4	50	78-155	38	<0.05	<0.05	<0.05	0.05	0.05	NA

Corn, grain	50	112-161	30	<0.01	<0.01	<0.01	0.01	0.01	NA

Corn, stover 4	50	92-176	38	<0.05	<0.05	<0.05	0.05	0.05	NA

Corn, K+CWHR	50	71-114	18	<0.01	<0.01	<0.01	0.01	0.01	NA

Sorghum, forage	50	61-113	24	<0.05	<0.05	<0.05	0.05	0.05	NA

Sorghum, grain	50	90-199	24	<0.01	<0.01	<0.01	0.01	0.01	NA

Sorghum, stover	50	90-199	24	<0.05	<0.05	<0.05	0.05	0.05	NA

Rice, grain	50	114-182	24	<0.01	<0.01	<0.01	0.01	0.01	NA

Rice, straw	50	114-182	24	<0.05	<0.05	<0.05	0.05	0.05	NA

Triazolylalanine (TA)

Wheat, forage	50	35-102	30	<0.05	0.12	0.11	0.05	0.05	0.015

Wheat, hay	50	56-135	30	<0.05	0.14	0.13	0.05	0.06	0.021

Wheat, grain	50	90-177	30	<0.05	0.26	0.24	0.06	0.10	0.063

Wheat, straw	50	90-177	30	<0.05	0.07	0.07	0.05	0.05	0.004

Corn, forage 4	50	78-155	38	<0.05	<0.05	<0.05	0.05	0.05	NA

Corn, grain	50	112-161	30	<0.05	0.35	0.31	0.05	0.07	0.065

Corn, stover 4	50	92-176	38	<0.05	<0.05	<0.05	0.05	0.05	NA

Corn, K+CWHR	50	71-114	18	<0.05	0.26	0.24	0.05	0.07	0.061

Sorghum, forage	50	61-113	24	<0.05	0.10	0.08	0.05	0.05	0.010

Sorghum, grain	50	90-199	24	<0.05	0.39	0.38	0.05	0.08	0.091

Sorghum, stover	50	90-199	24	<0.05	0.26	0.25	0.05	0.07	0.057

Rice, grain	50	114-182	24	<0.05	0.29	0.29	0.05	0.07	0.066

Rice, straw	50	114-182	24	<0.05	<0.05	<0.05	0.05	0.05	NA

Triazolyl-acetic acid (TAA)

Wheat, forage	50	35-102	30	<0.05	<0.05	<0.05	0.05	0.05	NA

Wheat, hay	50	56-135	30	<0.05	0.13	0.11	0.05	0.06	0.016

Wheat, grain	50	90-177	30	<0.01	0.20	0.20	0.04	0.05	0.046

Wheat, straw	50	90-177	30	<0.05	0.10	0.10	0.05	0.05	0.011

Corn, forage 4	50	78-155	38	<0.05	<0.05	<0.05	0.05	0.05	NA

Corn, grain	50	112-161	30	<0.01	<0.01	<0.01	0.01	0.01	NA

Corn, stover 4	50	92-176	38	<0.05	<0.05	<0.05	0.05	0.05	NA

Corn, K+CWHR	50	71-114	18	<0.01	<0.01	<0.01	0.01	0.01	NA

Sorghum, forage	50	61-113	24	<0.05	0.07	0.06	0.05	0.05	0.004

Sorghum, grain	50	90-199	24	<0.01	0.37	0.35	0.01	0.04	0.095

Sorghum, stover	50	90-199	24	<0.05	<0.05	<0.05	0.05	0.05	NA

Rice, grain	50	114-182	24	<0.01	0.50	0.50	0.03	0.07	0.134

Rice, straw	50	114-182	24	<0.05	0.34	0.34	0.05	0.08	0.082

1  For statistical calculations, the LOQ (0.01 ppm for triticonazole;
0.05 ppm for each triazole analyte, except for T and TAA in corn grain
and K+CWHR which have a LOQ of 0.01 ppm each) was used for all values
reported below the LOQ.

2  HAFT = Highest Average Field Trial.

3  Standard deviation is not applicable (NA) when all samples have
residues below the LOQ.

4  Represented by 8 sweet corn samples, and 30 field corn samples.

Corn forage samples from the sweet corn trials were harvested prior to
collection of K+CWHR from 3 trials and 50 days after in the other trial,
and corn forage from the 5 field corn trials, which also collected fresh
corn to represent K+CWHR and bridge sweet corn requirements, was
harvested 1-5 weeks after samples of fresh corn at the milk dough stage.
 The field corn forage samples do not actually represent sweet corn
forage typically collected prior to or with K+CWHR; however, given that
residues of triticonazole were nonquantifiable in all corn forage
samples and application was made to seed prior to planting, no
additional sweet corn forage samples will be required.

Conclusions.  The submitted residue data are adequate to support the
requested seed treatment uses for cereal grain crops (except rice)
pending submission of the final study report from an ongoing
triazole-related residues storage stability study.  There are adequate
data for the representative crops of the cereal grain groups 15 and 16
to establish crop group or individual tolerances.  The number and
locations of field trials were conducted according to the 860.1500
guidelines.  The seed treatment rate (0.05 lb ai/100 lbs seed) used in
the field trials reflects the proposed use of Triticonazole HL Fungicide
(EPA Reg. No. 7969-xxx) on barley, field corn and popcorn, oats, rye,
wheat, and triticale.  However, the rate reflects 5x and 2.5x the
proposed seed treatment rate for sweet corn and sorghum, respectively.

Residues of triticonazole were below the LOQ of 0.01 ppm in treated
wheat grain, corn grain, corn K+CWHR, and sorghum grain.  It is noted
that the seed treatment rate used for sweet corn and sorghum were
exaggerated.  Low but quantifiable residues of triticonazole were
observed in rice grain.  However, because the petitioner is excluding
the use of Triticonazole HL Fungicide on rice, the available data will
support a tolerance at the LOQ (0.01 ppm) for the cereal grains, group
15 (except rice).

Residues of triticonazole were also nonquantifiable in treated field and
sweet corn forage and stover, and sorghum forage and stover.
Quantifiable residues of triticonazole were observed in treated wheat
forage, hay and straw, and rice straw.  The appropriate tolerance levels
were statistically calculated (see Appendix I) according to Guidance for
Setting Pesticide Tolerances Based on Field Trial Data SOP.  The residue
data for rice straw was excluded from the spreadsheet because the
petitioner is not applying for use on rice.  The tolerance spreadsheet
calculated tolerances of 0.20 ppm for wheat forage, 0.25 ppm for wheat
hay, and 0.20 ppm for wheat straw.  Based on the maximum residue
determined for the representative crops, HED recommends a crop group 16
tolerance for triticonazole of 0.25 ppm.  A revised Section F must be
submitted to reflect the tolerance recommendation for the forage,
fodder, and straw of cereal grain, group 16.

The residue data and tolerances recommended in this document will also
support the currently registered seed treatment uses of Charter®
Fungicide Treatment (EPA Reg. No. 7969-386) for preplant seed treatment
on barley and wheat.

860.1520 Processed Food and Feed

DER Reference:  47511901.der.doc

BASF has submitted a processing study for triticonazole with field corn,
rice, sweet sorghum, and wheat.  Four field trials were conducted (one
field trial for each representative crop) in the United States during
the 2007 growing season.  At each test location, cereal grain crops were
grown from seeds treated with a 4.2 lb/gal flowable liquid formulation
of triticonazole, prior to planting, at 250 g ai/100 kg seed (4 oz
ai/100 lb seed; 5x the proposed seed treatment rate).  The triticonazole
formulation was mixed with Apron XL (mefenoxam; a seed fungicide) and a
colorant.  A separate plot (untreated) was planted with seed treated
with Apron XL and colorant only.  The application made to sorghum seed
additionally included pyraclostrobin; the pyraclostrobin data are not
reviewed herein.

Samples of field corn, rice and wheat grain, and sweet sorghum stalks
were collected at maturity and processed using procedures simulating
commercial practices for corn grits, meal, oil (dry and wet milled),
starch and flour; rice hulls, bran and polished rice; sorghum syrup; and
wheat bran, flour, middlings, shorts, and germ.

All samples were analyzed for triticonazole using LC/MS/MS Method 562/0.
 The method was adequate for data collection based on acceptable
concurrent method recoveries with wheat grain, corn grain, sorghum
stalk, and rice grain, bran, hulls and polished rice.  The validated
method LOQ was 0.01 ppm in/on all tested cereal grain RACs and processed
matrices.

Samples were also analyzed for the triazole-related metabolites,
triazole (T), triazolyl-acetic acid (TAA) and triazolylalanine (TA)
using LC/MS/MS Methods D0508 and D0604 (grain).  The validated method
LOQ was 0.01 ppm for T in wheat grain, bran, and flour; corn grain oil
and starch; sorghum stalks; and rice grain, bran, hulls and polished
rice, and TAA in wheat grain, bran, germ, middlings, shorts and flour;
corn grain, flour, grits, meal, oil and starch; sorghum stalks and
syrup; and rice grain, bran, hulls and polished rice.  The validated LOQ
for TA was 0.05 ppm in wheat grain, bran, germ, middlings, shorts and
flour; corn grain, flour, grits, meal, oil and starch; sorghum stalks
and syrup; and rice grain, bran, hulls, and polished rice.

RAC samples were stored frozen from harvest to analysis for
triticonazole residues for up to 6.7 months for corn grain, rice grain,
sorghum stalks, and wheat grain.  The only processed commodities
analyzed for triticonazole residues were stored frozen from collection
to analysis for up to 1 month for rice hulls, 1.5 months for wheat bran,
and 6.7 months for polished rice.  Storage stability data for
triticonazole are available for wheat grain, forage, hay, and straw, and
processed wheat germ, flour and bran which may be translated to support
the storage durations of corn, rice, and wheat grain, sorghum stalks,
and rice bran from the subject processing studies.

The maximum storage durations of RAC samples from harvest to analysis of
triazole residues were 10.4 months for corn, rice and wheat grain and
5.9 months for sorghum stalks.  Because T, TA, and TAA appear relatively
stable, data for wheat flour may be translated to support the storage
conditions and durations of wheat, corn, sorghum, and rice grain (RAC)
samples from the subject processing study.  A final report for stability
of T, TA and TAA in canola seed, turnip roots, mustard greens, and wheat
straw, grain, and forage is to be submitted upon completion.

The maximum storage durations for processed matrices from collection to
analysis for triazole metabolites were 0.3-0.4 months for corn oil and
starch; 1 month for rice bran and 1.2-1.3 months for hulls and polished
rice; 0.7 months for sorghum syrup; and 1.8-2.3 months for corn flour,
grits and meal, and wheat bran, flour, middlings, shorts and germ.  The
submitted storage stability data for wheat flour will support the
storage durations of corn and wheat flour samples and may be translated
to support polished rice samples.  Supporting storage stability data are
not required for corn oil and starch; rice bran; and sorghum syrup as
these matrices were analyzed within 30 days of processing.  Supporting
storage stability data are, however, required for T, TA and TAA in
frozen rice hulls, corn grits and meal, and wheat bran, middlings,
shorts, and germ.

The processing data for field corn, rice, sweet sorghum, and wheat
showed that residues of triticonazole were nonquantifiable (<0.01 ppm)
in the RACs (corn, rice, and wheat grain or sorghum stalk) grown from
seeds treated at 250 g triticonazole/100 kg seed.  Corn, sorghum and
wheat processed matrices were, therefore, not analyzed.  However, rice
processed matrices were analyzed because some quantifiable residues were
detected in the field trials conducted at the nominal rate (see
47470203.der.doc).  Residues of triticonazole were <0.01 ppm in polished
rice, 0.025-0.031 ppm in hulls, and 0.010-0.011 ppm in bran.  Based on
the results of the rice processing study, residues of triticonazole may
concentrate in hulls (2.8x) but do not appear to significantly
concentrate in bran (1.1x).  Processing factors in polished rice could
not be calculated because residues were nonquantifiable in both the RAC
and processed matrix.

Residues of the triazole-related metabolite T were nonquantifiable
(<0.01 ppm) in corn, rice and wheat grain, and sorghum stalks (RACs) and
the processed commodities of wheat bran and flour, corn oil (dry and wet
milled) and starch, and rice hulls, bran and polished rice.  Processing
factors could not be calculated for these matrices, and analysis of all
processed matrices was not required being that T residues were
nonquantifiable in the respective RAC samples.

Residues of the triazole-related metabolite TA were nonquantifiable
(<0.05 ppm) in sorghum stalks and processed syrup; therefore, processing
factors could not be calculated.  However, residues of TA were
quantifiable in wheat grain (0.08 ppm), corn grain (0.08-0.09 ppm), and
rice grain (0.06-0.07 ppm).  Residues of TA were 0.18-0.20 ppm in wheat
bran, <0.05 ppm in flour, 0.06 ppm in middlings, 0.08 ppm in shorts, and
0.13-0.23 ppm in germ; 0.052-0.060 ppm in corn grits, 0.098-0.105 ppm in
meal, and <0.05 ppm in oil (dry and wet milled), starch and flour; and
<0.05 ppm in rice hulls and polished rice, and 0.39-0.40 ppm in bran.
Based on the results of the wheat, corn and rice processing studies,
residues of TA do not concentrate in wheat flour (0.6x), middlings
(0.8x) and shorts (1x); corn grits (0.6x), oil (dry and wet milled;
0.6x), starch (0.6x), flour (0.6x), and meal (1.1x); and rice hulls
(0.7x) and polished rice (0.7x).  Residues of TA appear to concentrate
in wheat bran (2.4x) and germ (2.3x); and rice bran (5.7x).

Residues of the triazole-related metabolite TAA were nonquantifiable
(<0.01 ppm) in corn grain and sorghum stalks (RACs) and processed corn
grits, meal, oil (dry and wet milled), starch and flour, and sorghum
syrup, therefore, processing factors could not be calculated.  However,
residues of TAA were quantifiable in wheat grain (0.03 ppm) and rice
grain (0.10 ppm).  Residues of TAA were 0.04 ppm in wheat bran,
0.02-0.03 ppm in flour, 0.03 ppm in middlings, 0.03 ppm in shorts, and
0.03 ppm in germ; and 0.05-0.12 ppm in rice hulls, 0.05-0.06 ppm in
polished rice, and 0.58-0.65 ppm in rice bran.  Based on the results of
the wheat and rice processing studies, residues of TAA do not
concentrate in wheat flour, middlings, shorts, and germ (1x); and rice
hulls (0.9x) and polished rice (0.6x).  Residues of TAA appear to
concentrate in rice bran (6.2x) and only slightly in wheat bran (1.3x).

The observed processing factors of triticonazole in rice hulls (2.8x)
and bran (1.1x) were below the theoretical concentration factors
(860.1520, Table 3; based on separation into components) of 5x for rice
hulls and 7.7x for rice bran.  The theoretical concentration factors
(860.1520; Table 3) for other cereal grain matrices tested are 25x for
corn oil, 7.7x for wheat bran, 1.4x for wheat flour, and 8.3x for wheat
shorts.  No theoretical concentration factors are cited for sweet
sorghum in 860.1520.

A summary of the processing factors for triticonazole and the triazoles
TA and TAA is presented in Table 7.  T is not included because residues
were nonquantifiable in the RAC and all processed matrices tested.

  SEQ CHAPTER \h \r 1 Table 7.	Summary of Processing Factors for
Triticonazole and Triazoles.

RAC	Processed Commodity	Processing Factor 1

Triticonazole	TA	TAA

Wheat	Bran	NA	2.4x	1.3x

	Flour 	NA	0.6x	1x

	Middlings	NA	0.8x	1x

	Shorts	NA	1x	1x

	Germ	NA	2.3x	1x

Corn	Grits	NA	0.6x	NC

	Meal	NA	1.1x	NC

	Oil, dry milled	NA	0.6x	NC

	Oil, wet milled	NA	0.6x	NC

	Starch	NA	0.6x	NC

	Flour	NA	0.6x	NC

Sorghum, sweet	Syrup	NA	NC	NC

Rice	Polished rice	NC	0.7x	0.6x

	Hulls	2.8x	0.7x	0.9x

	Bran	1.1x	5.7x	6.2x

1 NA = Not analyzed because residues were nonquantifiable in the RAC at
nominal and exaggerated rates.

  NC = Not calculated because residues were nonquantifiable in both the
RAC and processed matrix.

Conclusions.  The processing data for field corn, rice, sweet sorghum,
and wheat are adequate pending submission of additional supporting
freezer storage stability data for T, TA, and TAA in rice hulls, corn
grits and meal, and wheat bran, middlings, shorts, and germ for up to 2
months.  The results indicate that residues of triticonazole were
nonquantifiable (<0.01 ppm) in the cereal grain RACs (corn, rice, wheat,
and sorghum) grown from seeds treated at 250 g triticonazole/100 kg seed
(5x the maximum proposed seed treatment rate).  The processed corn,
sorghum, and wheat matrices were not further analyzed.  Analysis of rice
processed matrices showed that residues of triticonazole may concentrate
in hulls (2.8x) but not significantly in bran (1.1x); residues in
polished rice were nonquantifiable.  As the petitioner is not seeking to
register use on rice at this time, no tolerances are required for rice
processed matrices.  However, based on the HAFT for rice grain (0.02
ppm) and processing factors of 2.8x for hulls, the maximum expected
triticonazole residues would be 0.06 ppm in rice hulls.

  SEQ CHAPTER \h \r 1 860.1650 Submittal of Analytical Reference
Standards

Analytical standards for triticonazole are currently available in the
EPA National Pesticide Standards Repository (personal communication with
Dallas Wright, ACB, 2/23/09), expiration date 7/8/2014.

860.1850 Confined Accumulation in Rotational Crops

DER Reference:  47399201.der.doc

Residue Chemistry Memo DP# 262566, 6/6/2001, N. Dodd (PP#9F6051)

BASF has submitted a confined rotational crop study with
[14C-phenyl]triticonazole and [3(5)-14C-triazole]triticonazole.  The
study was submitted in support of the current petition and in response
to the condition of registration requirement under PP# 9F6051 (DP#
262566, 6/6/2001, N. Dodd).  Each radiolabeled test substance was
applied as a solution in methanol to bare soil in pots maintained in a
greenhouse at a nominal rate of 0.107 lb ai/A.  After soil treatment,
rotational crops consisting of lettuce, radish, and spring wheat were
planted 30, 120 and 365 days.  Lettuce, radish roots and tops, and wheat
grain, chaff and straw were harvested at maturity, and wheat forage was
harvested 61-63 days after planting (DAP).

Total radioactive residues (TRR) were determined for the rotated crops;
see Table 8 below.  TRR ranged from 0.003 ppm in phenyl-label radish
root (365-day PBI) to 0.848 ppm in triazole-label wheat chaff (120-day
PBI).  Significantly higher TRR (by a factor of ≥3) were observed in
the triazole-label matrices than in the respective phenyl-label
matrices.  TRR typically declined with later plantback intervals (PBIs),
except in mature wheat matrices (straw, chaff, and/or grain).

Table 8.  Total Radioactive Residues in Rotated Lettuce, Radish, and
Wheat Matrices.

Matrix	Plantback interval

(days)	Phenyl Label (ppm) 	Triazole Label (ppm)

Combustion	Calculated 1	Combustion	Calculated 1

Lettuce	30	0.020	0.024	0.065	0.065

	120	0.014	0.014	0.026	0.025

	365	0.005	0.004	0.029	0.024

Radish, roots	30	0.009	0.009	0.099	0.094

	120	0.006	0.006	0.055	0.056

	365	0.003	0.003	0.031	0.029

Radish, tops	30	0.072	0.067	0.279	0.256

	120	0.052	0.040	0.331	0.286

	365	0.011	0.009	0.128	0.043

Wheat, forage	30	0.067	0.042	0.199	0.129

	120	0.049	0.035	0.155	0.095

	365	0.029	0.015	0.141	0.107

Wheat, straw	30	0.209	0.181	0.629	0.580

	120	0.345	0.298	0.675	0.576

	365	0.282	0.198	0.520	0.455

Wheat, chaff	30	0.181	0.174	0.509	0.571

	120	0.151	0.141	0.848	0.786

	365	0.106	0.095	0.562	0.549

Wheat, grain	30	0.008	0.008	0.453	0.948

	120	0.054	0.053	0.689	0.706

	365	0.025	0.028	0.682	0.773

1 Calculated by the summation of extractable and nonextractable
radioactivity; these values were used by the petitioner for all further
calculations.

To characterize and identify radioactive residues in rotated crops,
samples were sequentially extracted and partitioned with organic
solvents.  The nonextractable residues in representative 120-DAT wheat
grain and straw were further released with aqueous ammonia extraction
and enzyme hydrolysis.  Initial identification of extracts and
hydrolysates was accomplished by co-chromatography using several HPLC
systems, and confirmation of residues was made by LC/MS/MS.  TRR
accountabilities were 63-120% for phenyl-label rotated crop matrices and
34-209% for triazole-label rotated crop matrices.  Accountabilities
indicate that the extraction procedures may not have adequately released
radioactivity in some rotated crop matrices, but TRR levels in the
extracted samples were sufficient to characterize the residues in
rotated crops matrices.

The parent, triticonazole, was the only residue identified in
phenyl-label rotated crop matrices.  Triticonazole accounted for
4.2-15.4% TRR (<0.01 ppm) in 30-DAT lettuce, radish root and tops, and
wheat forage and chaff, and 6.5% TRR (0.012 ppm) in 30-DAT wheat straw;
30-DAT wheat grain was not analyzed because extractable radioactivity
was only 0.002 ppm.  In 120-DAT rotated crop samples, triticonazole
accounted for 0.2-10.0% TRR (<0.01 ppm) in lettuce, radish tops, and
wheat forage, chaff, and grain, and 8.2% TRR (0.025 ppm) in wheat straw;
120-DAT radish root was not analyzed because extractable radioactivity
was only 0.004 ppm.  In 365-DAT rotated crop samples, triticonazole
accounted for 3.5-4.8% TRR (<0.01 ppm) in wheat straw and chaff; other
365-DAT crop matrices (lettuce, radish tops and root, wheat grain and
forage) were not analyzed because extractable radioactivities were only
0.002-0.006 ppm.

The parent, triticonazole, was also identified in all triazole-label
rotated crop matrices, except wheat grain.  Triticonazole accounted for
7.8% TRR (<0.01 ppm) in 30-DAT radish root, and 19.2-32.1% TRR
(0.017-0.133 ppm) in 30-DAT lettuce, radish tops, and wheat forage,
straw and chaff.  In 120-DAT rotated crop samples, triticonazole
accounted for 5.2% and 5.5% TRR (<0.01 and 0.016 ppm) in radish root and
tops, respectively, 22.3% TRR (<0.01 ppm) in lettuce, and 14.5-26.0% TRR
(0.019-0.150 ppm) in wheat forage, straw and chaff.  In 365-DAT rotated
crop samples, triticonazole accounted for 6.6-13.6% TRR (<0.01 ppm) in
lettuce, radish root, and radish tops, and 18.9-24.1% TRR (0.025-0.133
ppm) in wheat forage, straw and chaff.

Triazole-related metabolites, TA and TAA, were identified in
triazole-label rotated crop matrices.  TA accounted for 1.0-6.4% TRR
(0.004-0.017 ppm) in 30-DAT lettuce, wheat straw, and wheat grain, and
10.8-40.4% TRR (0.028-0.103 ppm) in radish root and tops, and wheat
forage and grain.  TAA was only identified in 30-DAT lettuce at 12.2%
TRR (0.008 ppm) and wheat straw, chaff, and grain at 17.1-29.8% TRR
(0.139-0.173 ppm).  In 120-DAT rotated crop samples, TA residues
increased in most mature matrices and accounted for 13.2% TRR (0.003
ppm) in lettuce, and 6.8-44.4% TRR (0.013-0.313 ppm) in radish root and
tops, and wheat forage, chaff and grain; TA was not detected in 120-DAT
wheat straw.  In 365-DAT rotated crop samples, TA residues increased in
all matrices, except wheat grain, and accounted for 21.7-24.8% TRR
(0.005-0.007 ppm) in lettuce and radish root, 34.7-40.7% TRR
(0.015-0.044 ppm) in radish tops and wheat forage, and 8.5-8.8% TRR
(0.048-0.066 ppm) in wheat chaff and grain; TA was detected at low
levels (2.0% TRR, 0.009 ppm) in 365-DAT wheat straw.  TAA was not
detected in any 120- or 365-DAT samples.

16% TRR (≤0.001 to ≤0.016 ppm) in phenyl-label samples and ~1-29%
TRR (≤0.001 to ≤0.027 ppm) in triazole label-samples.

All samples and extracts were stored frozen prior to analysis.  Based on
the analysis dates obtained from the HPLC chromatograms, the majority of
rotated crop samples were initially analyzed within six months of
harvest.  Several samples (i.e., 30-DAT lettuce, radish roots and tops,
and wheat forage, straw and chaff; 120-DAT wheat straw; and 365-DAT
lettuce, wheat forage and chaff) were stored for up to 9.6 months prior
to initial HPLC analysis.  HPLC analyses and co-chromatography to
further characterize and confirm metabolite identifications were
conducted on samples/extracts stored up to ~18 months.  The dates of
sample extraction, partitioning, and further hydrolysis of
nonextractable wheat grain and straw samples were not reported.

Re-analysis of methanol extracts of phenyl-label lettuce, radish root,
radish tops and spring wheat (30-DAT), and triazole-label lettuce,
radish root and wheat grain (30-DAT) demonstrate similar metabolic
profiles in the re-analyzed (~13 months after initial analysis) and
initial sample extracts.  Re-extraction and re-analysis of phenyl-label
radish top and triazole-label radish root and wheat grain samples
(~14-15 months after the initial analysis) also demonstrate similar
extractability and metabolic profiles in the re-extracted and initial
samples.  Given that the majority of samples appear to have been
analyzed within 6 months, the available storage stability data will be
considered adequate to support the subject study.

Based on the submitted confined rotational crop study, HED concludes
that metabolism of triticonazole in rotational crops involved
degradation of triticonazole in the soil resulting in the formation of
free triazole.  As a very polar compound, free triazole is easily taken
up by the plants and transformed to triazolylalanine (TA), which is
further metabolized to triazolylacetic acid (TAA) and other polar
conjugates.  The occurrence of residual radioactivity indicates that a
portion of residues was incorporated and/or associated into natural
products, such as starch, cellulose and/or lignins.

Conclusions.  The confined rotational crop study is acceptable.  The
application rate used reflects 1.4x the equivalent per acre rate
proposed for cereal grain crops.  The metabolism of triticonazole in
rotated crops appears similar to those observed for primary crops,
except that triazole-related metabolites were detected in the rotated
crops.  The data indicate that residues of triticonazole may be present
at >0.01 ppm in 30-DAT rotated lettuce (0.017 ppm), radish tops (0.049
ppm) and wheat forage (0.041 ppm), straw (0.133 ppm) and chaff (0.139
ppm); 120-DAT rotated radish tops (0.016 ppm), and wheat forage (0.019
ppm), straw (0.150 ppm), and chaff (0.114 ppm); and 365-DAT rotated
wheat forage (0.025 ppm), straw (0.086 ppm) and chaff (0.133 ppm).
Wheat hay was not analyzed but forage and straw were analyzed, and
residues of triticonazole were found in forage and straw.

860.1900 Field Accumulation in Rotational Crops

The proposed label for the 4.17 lb/gal FS specifies that “planting of
any crop not listed on the label within 30 days after planting treated
seed is not allowed”.  The results of the submitted confined
rotational crop study do not support this restriction.  The data from
the confined rotational crop study indicate that triticonazole residues
greater than 0.01 ppm were detected at the 30-day PBI.  To support a
30-day plantback restriction on the label, limited field rotational crop
data for leafy vegetables, root and tuber vegetables, foliage of root
and tuber vegetables, and a cereal grain are required.  Until the
requested data are provided, the label must be modified to specify a
120-day (4-month) plantback restriction for leafy vegetables, a 365-day
(12-month) plantback restriction for root and tuber vegetables, and
prohibit the planting of all other crops not listed on the label.

Although triticonazole was detected at >0.01 ppm in rotated wheat
forage, straw, and chaff planted at the 30-, 120- and 365-day PBIs, the
levels of triticonazole found in the confined rotational crop studies
were below the recommended tolerance of 0.25 ppm for the forage, fodder,
and straw of cereal grain crop group.  Therefore, residues which may be
found in rotated cereal grain crops (foliage) in the confined rotational
crop study would not be expected to exceed the recommended tolerances
for triticonazole.  Nevertheless, HED continues to request data on a
rotated cereal grain because the cereal grain represents other crops and
residues in wheat as a rotational crop are often the highest.

860.1550 Proposed Tolerances

Tolerances have been established under 40 CFR §180.583(a) for residues
of the fungicide triticonazole,
(1RS)-(E)-5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H
-1,2,4-triazol-1-ylmethyl)cyclopentanol, from the treatment of seed
prior to planting in/on barley grain, hay and straw, and wheat grain,
forage, hay and straw, each at 0.05 ppm.  HED has previously determined
that triticonazole is the residue of concern in barley and wheat from
seed treatment uses.  This regulatory decision may be extended to
include all crop commodities in the cereal grains crop group.  The
petitioner has not specified the tolerance expression with the proposed
tolerances in Section F of the petition.

The submitted residue data for field corn grain, sweet corn K+CWHR,
sorghum grain, and wheat grain, which are the representative commodities
of the cereal grain group,  do not support the proposed  tolerance for
the ‘Grain, cereal, group 15 (except rice)’ at 0.05 ppm.  The data
do support a tolerance for ‘Grain, cereal, group 15 (except rice)’
at 0.01 ppm. A revised Section F must be submitted to reflect the
tolerance recommendation of 0.01 ppm for “Grain, cereal, group 15
(except rice)” at 0.01 ppm. The established individual tolerances for
wheat grain and barley grain must be deleted when the crop group
tolerance is established.

The submitted residue data for corn forage and stover, sorghum forage
and stover, and wheat forage, hay, and straw are adequate to determine a
tolerance level for the forage, fodder, and straw of cereal grains crop
group (except rice).  Since the residues in wheat commodities were
highest, the tolerance levels for wheat forage, wheat hay, and wheat
straw were statistically calculated (see Appendix I) according to
Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP
(January 2008 version).  Because >10% of the residues were below the LOQ
(<0.01 ppm), the maximum likelihood estimation (MLE) procedures were
needed to impute censored values.  The tolerance spreadsheet calculated
tolerances of 0.20 ppm for wheat forage, 0.25 ppm for wheat hay, and
0.20 ppm for wheat straw.  HED recommends a crop group tolerance of 0.25
ppm for the forage, fodder, and straw of the cereal grain crop group,
group 16, based on the highest calculated value for the wheat
commodities (0.25 ppm for wheat hay).

A revised Section F must be submitted to reflect the tolerance
recommendation of 0.25 ppm for “Grain, cereal, forage, fodder, and
straw, group 16 (except rice)” as shown in Table 9. The established
individual tolerances for barley hay and straw, and wheat forage, hay
and straw must be deleted when the crop group tolerance is established.

The processing data for corn, sorghum, and wheat showed no concentration
of triticonazole residues following seed treatment at 5x.  The
processing data for rice showed that residues of triticonazole
concentrated in hulls (2.8x) but not significantly in bran (1.1x).  As
rice is excluded from the proposed seed treatment uses on cereal grains,
no tolerances are required for the processed commodities of cereal
grains for the purpose of this action.

Based on the available cow and poultry metabolism studies, and low
levels of residues found in the cereal grain field trials, there is no
reasonable expectation that quantifiable residues of triticonazole will
occur in livestock commodities [40 CFR §180.6(a)(3)].  Therefore,
livestock tolerances are not required at this time.

A summary of the recommended tolerances for the petition is listed in
Table 9.  There are no Codex or Mexican MRLs established for residues of
triticonazole.  Canadian MRLs are established for triticonazole per se
in/on barley, wheat and oats each at 0.01 ppm.

Table 9. 	Tolerance Summary for Triticonazole

Commodity	Established/Proposed Tolerance (ppm)	Recommended Tolerance
(ppm)	Comments; Correct Commodity Definition

Established tolerances under 180.583(a)

Barley, grain	0.05	Remove	Barley grain will be covered with the
establishment of the cereal grain, group 15 (except rice) tolerance.

Barley, hay	0.05	Remove	Increase in the tolerance based on residues
resulting from new uses. Barley hay and straw and wheat forage will be
covered with the establishment of the cereal grain group 16 (except
rice) tolerance.

Barley, straw	0.05	Remove

	Wheat, forage	0.05	Remove

	Wheat grain	0.05	Remove	Barley grain will be covered with the
establishment of the cereal grain, group 15 (except rice) tolerance

Wheat, hay	0.05	Remove	Increase in the tolerance based on residues
resulting from new uses. Wheat hay and straw and will be covered with
the establishment of the cereal grain group 16 (except rice) tolerance.

Wheat, straw	0.05	Remove

	Tolerances to be established under 180.583(a)

Grain, cereal, group 15 (except rice)	0.05	0.01	.

Grain, cereal, forage, fodder, and straw, group 16 (except rice)	0.10
0.25	.

References

DP#:		270496

Subject:	PP#9F6051.  Triticonazole on Barley and Wheat.  Method
Validation Request.

From:		N. Dodd

To:		F.D. Griffith

Dated:		12/7/2000

MRIDs:  	44904518, 44904519

DP#:		262566

Subject:	PP#9F6051.  Triticonazole Seed Treatment on Barley and Wheat.
Review of Analytical Methods and Residue Data.  First Food Use Review.

From:		N. Dodd

To:		S. Gardner-Jenkins/M. Waller

Dated:		6/6/2001

MRIDs:  	44904515-25, 44995701-06

DP#:		322215

Subject:	1,2,4-Triazole, Triazole Alanine, Triazole Acetic Acid:  Human
Health Aggregate Risk Assessment in Support of Reregistration and
Registration Actions for Triazole-derivative Fungicide Compounds.

From:		M. Doherty; K. Raffaele; K. Farwell; S. Dapson; K. Schumacher; J.
Arthur; D. Hrdy; I. Maher

To:		T. Gibson/C. Giles Parker; M. Goodis; S. Lewis

Dated:		2/7/2006

MRIDs:  	None

DP#:  	303508 & 314517

Subject:	PP#4F6830.  Prothioconazole.  Petition for Establishment of
Tolerances for Use on Barley, Oilseed (Except Sunflower and Safflower)
Crop Group, Dried Shelled Pea and Bean (Except Soybean) Crop Subgroup,
Peanut, Rice, and Wheat.  Summary of Analytical Chemistry and Residue
Data.

From:	S. Funk

To:	L. Coppolino

Date:	8/21/06

MRIDs:	46246139, 46246141-50, 46246201-11, 46246213-27, 46477701-04

  SEQ CHAPTER \h \r 1 Attachments:

International Residue Limit Status sheet

Appendix I - Tolerance Assessment Calculations

Template Version September 2005

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name:  (1RS)-(E)-5-[4-chlorophenyl)

methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1ylmethyl)cyclopentanol
Common Name:

Triticonazole

	X Proposed tolerance

( Reevaluated tolerance

( Other	Date:  02/2009

Codex Status (Maximum Residue Limits)	U. S. Tolerances

X No Codex proposal step 6 or above

( No Codex proposal step 6 or above for the crops requested	Petition
Number:  PP#8F7420

DP#:  360624

Other Identifier:  Decision # 399232

Residue definition (step 8/CXL): N/A	Reviewer/Branch:  P. Deschamp, A.
Acierto/RAB3

	Residue definition:  triticonazole per se

Crop (s)	MRL (mg/kg)	Crop(s) 	Tolerance (ppm)

Grain, cereal, group 15 (except rice)	0.05

Grain, cereal, forage, fodder and straw, group 16 (except rice)	0.10

	Limits for Canada	Limits for Mexico

(  No Limits

( No Limits for the crops requested	X No Limits

( No Limits for the crops requested

Residue definition:
5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethy
l)cyclopentanol

	Residue definition:  N/A

Crop(s)	MRL (mg/kg)	Crop(s)	MRL (mg/kg)

Barley	0.01

Wheat	0.01

Oats	0.01

Notes/Special Instructions: S.Funk, 02/19/2009.

Appendix I.  Tolerance Assessment Calculations.

Wheat

The dataset used to establish tolerances for triticonazole on wheat
forage, hay, and straw consisted of field trial data representing
application rates of 50 g ai/100 kg seed (seed treatment), with samples
collected at typical commercial harvest.  As specified by the Guidance
for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the
field trial application rates are within 25% of the maximum label
application rate.  The residue values that were entered into the
tolerance spreadsheet are provided in Table I-1.

Because 4 of 30 field trial sample results for wheat forage, 8 of 30
field trial sample results for wheat hay, and 6 of 30 field sample
results for wheat straw were below the LOQ, maximum likelihood
estimation (MLE) procedures were needed to impute censored values.  For
these matrices visual inspection of the lognormal probability plots
(Figures I-1, I-3, and I-5) and the results from the approximate
Shapiro-Francia test statistic (Figures I-2, I-4, and I-6) indicated
that the datasets were reasonably lognormal.

Since the field trial data for triticonazole on wheat forage, hay, and
straw represent large datasets (i.e., more than 15 samples) and are
reasonably lognormal, the minimum of the 95% upper confidence limit
(UCL) on the 95th percentile and the point estimate of the 99th
percentile should be selected as the tolerance value.  Using the
rounding procedure as outlined in the SOP, the recommended tolerances
are 0.20 ppm for wheat forage, 0.25 ppm for wheat hay, and 0.20 ppm for
wheat straw.

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Crop:	Wheat, forage (MLE)	Wheat, hay (MLE)	Wheat, straw (MLE)

PHI:	Not applicable	Not applicable	Not applicable

App. Rate:	50 g ai/100 kg seed	50 g ai/100 kg seed	50 g ai/100 kg seed

Submitter:	BASF Crop Protection	BASF Crop Protection	BASF Crop
Protection

MRID Citation:	MRID 47470203	MRID 47470203	MRID 47470203

	Residues of Triticonazole (ppm) 1

	0.070	0.070	0.030

	0.050	0.070	0.040

	0.005	0.002	0.020

	0.006	0.010	0.020

	0.010	0.004	0.004

	0.010	0.005	0.005

	0.100	0.060	0.050

	0.090	0.060	0.060

	0.050	0.080	0.030

	0.070	0.080	0.040

	0.020	0.006	0.006

	0.020	0.006	0.007

	0.009	0.007	0.010

	0.009	0.010	0.020

	0.030	0.010	0.020

	0.030	0.020	0.020

	0.020	0.020	0.030

	0.020	0.020	0.020

	0.020	0.009	0.008

	0.020	0.009	0.009

	0.020	0.020	0.010

	0.020	0.030	0.020

	0.050	0.070	0.080

	0.060	0.070	0.080

	0.090	0.030	0.080

	0.080	0.040	0.080

	0.020	0.030	0.040

	0.020	0.020	0.040

	0.030	0.060	0.040

	0.030	0.040	0.060

1 Bolded residues are MLE calculated values for residues reported as
below the LOQ (<0.01 ppm).

Figure I-1.  Lognormal probability plot of triticonazole field trial
data for wheat forage.

Figure I-2.  Tolerance spreadsheet summary of triticonazole field trial
data for wheat forage.

Figure I-3.  Lognormal probability plot of triticonazole field trial
data for wheat hay.

Figure I-4.  Tolerance spreadsheet summary of triticonazole field trial
data for wheat hay.

Figure I-5.  Lognormal probability plot of triticonazole field trial
data for wheat straw.

Figure I-6.  Tolerance spreadsheet summary of triticonazole field trial
data for wheat straw.

Triticonazole                  Summary of Analytical Chemistry and
Residue Data	DP#s:  360624; 325956, 353372

 PAGE

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