Document ID: EPA-HQ-OPP-2007-0536-0013
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2009-12-23T05:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

OFFICE OF           

PREVENTION, PESTICIDES

AND TOXIC SUBSTANCES

MEMORANDUM

	Date:	15/NOV/2006

	Subject:	Fenarimol.  Section 3 Registration on Hops.  Summary of
Analytical Chemistry and Residue Data.  Petition Number 6E7074 

		DP Number: 331894	Decision Number:  367682	

		PC Code:  206600	MRID Numbers:  46842801	

		40 CFR 180.421	Chemical Class:  Fungicide

	From:	Debra Rate, PhD, Biologist

		Alternative Risk Integration Assessment (ARIA) Team

Risk Integration, Minor Use and Emergency Response (RIMUER) Branch 

		Registration Division (7505P)

	Through:	William Cutchin, Acting Branch Senior Scientist

		ARIA

Technical Review Branch (TRB) 

		Registration Division (7505P)

		

		And

		Douglas A. Dotson, Ph.D., Chemist

		Registration Action Branch 2 (RAB2)

		Health Effects Division (HED) (7509P)

	To:	Breann Hanson, Biologist

		ARIA Team

RIMUER Branch 

		Registration Division (7505P)

Executive Summary

Fenarimol
[alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-5-pyridinemethanol] is a
member of the pyrimidine class of fungicides.  Other members of this
fungicide class include dimethirimol, ethirimol and bupirimate.  It is
the only member of this class registered in the U.S.  Fenarimol is a
localized systemic foliar fungicide used for control of such pests as
acab, powdery mildew, rusts, and leaf spot.  Fenarimol inhibits fungal
growth by adversely affecting the formation of the fungal sterol
ergosterol.  Fenarimol is currently registered for use on fruit and nut
crops such as apples, cherries, filberts (nonbearing), grapes, pears,
and pecans as well as on ornamental plants, trees, and grasses and turf
lawns.  Fenarimol is also used on imported bananas.  The current
proposal is for a requested tolerance of 1.2 ppm for the residues of
fenarimol in/on hops.  Fenarimol formulations include granular (0.78%
ai, turf use only), soluble concentrate/liquid (11.6% ai), flowable
concentrate (2.4% ai), and emulsifiable concentrates (11.6% ai and 12%
ai).  The only fenarimol formulation class which is registered for use
on fruit and nut crops is an emulsifiable concentrate sold under the
trade name Rubigan™ EC, and this formulation is typically applied
using ground equipment.  The proposed use of Rubigan™ EC on hops is
for an application rate of 7 fl.oz/A (0.055 lb ai/A) Rubigan™ EC once
powdery mildew is observed, with retreatment intervals (RTIs) of 14
days, not to exceed 28 fl oz/A (1.0 lb ai/A).

Although the nature of the residue in fenarimol-treated hops has not
been directly determined, the nature of the residue in plants and
animals is well understood.  Radioactive metabolism studies with apples
and cherries indicated that fenarimol was the only significant component
of the residue.  Although the Metabolism Assessment Review Committee
(MARC) suggested that field trial studies on new crops include data for
parent and metabolites (B &C), the registrant submitted data for only
fenarimol, per se on hops.  Environmental fate studies show that
fenarimol is persistent and moderately mobile in the environment.  It is
believed to be stable to hydrolysis, anaerobic microbial degradation and
photolysis on soil.  It is degraded very slowly, if at all, by aerobic
microbial processes with a reported mean aerobic soil metabolism
half-life of about 4 years.  In field studies fenarimol reportedly
dissipated with half-lives of 3 months to several years from soil and
turf surfaces and much slower when incorporated into soil.  No single
degradate was found to represent more than 7% of applied parent in field
dissipation studies.  

The Interregional Research Project No. 4 (IR-4) submitted field trial
data for fenarimol on hops.  Three field trials were conducted in EPA
geographical Regions 11 and 12.  The number and location of these trials
are in accordance with OPPTS Guideline 860.1500.  IR-4 conducted the
sample analysis for residues of fenarimol.  The procedure used was
derived from DowElanco: Letcombe Laboratory method, “Determination of
Fenarimol Residues in Fresh, Dried and Spent Hops.”  Briefly, the
residues were extracted from the samples using methanol, purified by
sodium bicarbonate and methyl tert-butyl ether liquid/liquid partition
and subjected to alumina column clean-up prior to analysis using gas
chromatography (GC) with an electrolytic conductivity detector (ECD). 
The lowest level of method validation (LLMV) in this study was 0.100 ppm
fenarimol.  The limit of quantitation (LOQ) for the method was 0.12 ppm,
and the limit of detection (LOD) was 0.041 ppm, approximately one-third
of the LOQ.  

Although it will not affect the recommendation of the tolerance of
fenarimol residues on hops, the fenarimol residue chemistry database
does not contain storage stability data for livestock commodities. 
Storage stability data for these commodities are required to support the
storage intervals used in the livestock feeding studies.

The storage stability study submitted supports the use of fenarimol
in/on hops.  Although the storage stability recoveries averaged 67%, the
concurrent recoveries and method validation recoveries ranged from 64%
to 94% with an overall average of 78% recovery.  The calculated
tolerance based on reported field trial residues (0.742 ppm maximum) of
fenarimol on hops and residue decay (~30%) support the proposed
tolerance of 1.2 ppm.

The terminal residues of concern in plants and animals are fenarimol,
per se and/or fenarimol plus metabolites, B and C.  The current
registered tolerances as per 40 CFR 180.421 are the following:

fenarimol
[alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol]:

Apple...............................................................0.1

Apple, dry pomace...........................................        2.0

Apple, wet pomace...........................................        2.0

Cattle, fat.................................................        0.1

Cattle, kidney..............................................        0.1

Cattle, meat................................................        0.01

Cattle, meat byproducts, except kidney......................        0.05

Filbert.....................................................        0.02

Goat, fat...................................................        0.1

Goat, kidney................................................        0.1

Goat, meat..................................................        0.01

Goat, meat byproducts, except kidney........................        0.05

Horse, fat..................................................        0.1

Horse, kidney...............................................        0.1

Horse, meat.................................................        0.01

Horse, meat byproducts, except kidney.......................        0.05

Pear........................................................        0.1

Pecan.......................................................        0.1

Sheep, fat..................................................        0.1

Sheep, kidney...............................................        0.1

Sheep, meat.................................................        0.01

Sheep, meat byproducts, except kidney.......................        0.05

A tolerance is established for combined residues of the fungicide
fenarimol
[alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol] and
its metabolites
[alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-1,4-dihydro-5-pyrimidinem
ethanol and 5-[(2-chlorophenyl)
(4-chlorophenyl)methyl]-3,4-dihydro-4-pyrimidinol measured as the total
of fenarimol and 5-[(2-chlorophenyl)-(4-chlorophenyl)methyl]pyrimidine
(calculated as fenarimol)]:

Banana*...................................................        0.5

  (more than 0.25 ppm shall be present in the pulp after peel is
removed)

Cherry......................................................        1.0

Grape, juice................................................        0.6

Grape pomace (wet and dry)..................................        2.0

Grape.......................................................        0.2

Grape, raisin, waste........................................        3.0

Grape, raisin...............................................        0.6

* There are no United States registrations for banana as of April 26,

  1995.

Milk, eggs, poultry tissue and hog tissue were not included in the
tolerance expression because the Agency has determined that there is no
reasonable expectation of finite residues of fenarimol in these animal
commodities.  There are no poultry or hog feed items associated with the
registered uses of fenarimol.  

Regulatory Recommendations and Residue Chemistry Deficiencies

Residue Chemistry Deficiencies:

Although it will not affect the recommendation of the tolerance of
fenarimol residues on hops, the fenarimol residue chemistry database
does not contain storage stability data for livestock commodities. 
Storage stability data for these commodities are required to support the
storage intervals used in the livestock feeding studies. 

A 5 gram sample of analytical reference standard must be submitted to
the Agency Pesticide Repository.

Recommendations:

Pending receipt of the reference sample, ARIA recommends that the
requested tolerance of 1.2 ppm be set for the residues of fenarimol, per
se in/on hops.  A Human Health Risk Assessment is forthcoming.

Background

MRID No. 468428.der.doc, D. Rate, 12/SEP/2006.

imol is also used on imported bananas.  The only fenarimol formulation
class which is registered for use on fruit and nut crops is an
emulsifiable concentrate sold under the trade name Rubigan™, and this
formulation is typically applied using ground equipment.

TABLE 1.	Test Compound Nomenclature

Compound	Chemical Structure:

-2,4-dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol

CAS name	α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol

CAS #	60168-88-9

End-use product/(EP)	Rubigan™ EC

TABLE 2.	Physicochemical Properties of the Technical Grade Test Compound

Parameter	Value	Reference

Melting point/range	  SEQ CHAPTER \h \r 1 117-119°C  SEQ CHAPTER \h \r
1 	MRID No. 00149382

pH	Not available.  There is no hydrolysis up to 52°C at pH 3, 6, or 9.
MRID No.   SEQ CHAPTER \h \r 1 00156033  

Density	  SEQ CHAPTER \h \r 1 0.66-0.81 g/cc (packed)	MRID No.   SEQ
CHAPTER \h \r 1 00156033

Water solubility ( 25°C)	  SEQ CHAPTER \h \r 1 13.7 ppm at pH 7 and
25°C	MRID No.   SEQ CHAPTER \h \r 1 00149382

Solvent solubility (mg/L at 25°C)	  SEQ CHAPTER \h \r 1 hexane (1.1
mg/mL); acetonitrile, heavy aromatic naphtha, and xylene (≤50 mg/mL);
benzene and methanol (100-125 mg/mL); acetone (>250 mg/mL); and
chloroform and cyclohexanone (>500 mg/mL)	MRID No.   SEQ CHAPTER \h \r 1
00149382

Vapor pressure at 25°C	  SEQ CHAPTER \h \r 1 2.2 x 10-7 Torr at 25° C
MRID No.   SEQ CHAPTER \h \r 1 00149382

Dissociation constant (pKa)	No hydrolysis up to 52°C at pH 3, 6, or 9.
MRID No.   SEQ CHAPTER \h \r 1 00149382

Octanol/water partition coefficient Log(KOW)	  SEQ CHAPTER \h \r 1 3.69
MRID No.   SEQ CHAPTER \h \r 1 00149382

UV/visible absorption spectrum	Not available.

	

860.1200  Directions for Use

TABLE 3.  Summary of Directions for Use of Fenarimol.

Application, Timing, Type, and Equipment	

Formulation

[EPA Reg. No.]	

Applic. Rate

(lb ai/A)	

Max. No. Applic. per Season	

Max. Seasonal Applic. Rate

(lb ai/A)	

PHI

(days)	

Use Directions and Limitations

HOPS

Once powdery mildew is observed. Emulsifiable concentrate.	

10163-273	

7 fl oz/A

(0.055)	

4	

28 fl oz/A

(1.0)	

10	

Repeat applications at 14 day intervals, not exceed 28 fl oz /A  (1.0 lb
ai/A)

The proposed use directions are adequate.

860.1300 Nature of the Residue - Plants

DP Num: 277692; D. Drew; 17/SEP/2001

DP Num: 277482, D.Drew, 14/AUG/2001

The registration requirements for plant metabolism are fulfilled. 
Acceptable studies depicting the metabolism of [14C]fenarimol in plant
matrices (apple, cherry, grape and banana) are available.  The MARC has
determined that for enforcement purposes, fenarimol per se would be an
adequate indicator of misuse, and that the tolerance should be expressed
in terms of parent only.  However, the dietary assessment for grapes and
bananas should also include the metabolites B and C (See Attachment 1
for structures). 

860.1300 Nature of the Residue - Livestock

The qualitative nature of the residue in milk and ruminant tissues is
adequately understood.  For the purpose of this registration, since hops
are not items of animal feed, considerations of secondary tolerances in
meat, meat byproducts, milk, poultry, and eggs do not apply.

860.1340 Residue Analytical Methods

MRID No. 46842801.der.doc, D. Rate, 12/SEP/2006.

Analytical methodology exists for the enforcement of currently
established tolerances for fenarimol.  The method, GC/ECD, is published
in PAM Vol  II  (Method R039).  For the purposes of this Section 3
registration action, Method R039 may be used to enforce the required
tolerance for fenarimol in/on hops.  Adequate recovery data was
submitted with MRID No. 46842801 for the residues of fenarimol.  This
data included method validation recoveries, concurrent recoveries and
storage stability concurrent recoveries.  The range of recoveries  was
64%-94% with an average of 78%.

860.1360 Multiresidue Methods

DP Num: 277692; D. Drew; 17/SEP/2001

The Pesticide Analytical Manual (PAM) Vol. II lists three GC/ECD
methods, designated as Methods I, II, and III, for the enforcement of
tolerances for fenarimol residues in/on plant and animal commodities. 
Method I determines residues of fenarimol per se in/on fruits,
vegetables, and miscellaneous other crops (including, but not limited
to, apples, grapes ,bananas, grains, beans).  Method II determines
residues of fenarimol per se in animal commodities (cattle, eggs, milk,
and poultry).  Method III determines residues of fenarimol and its
regulated metabolites (B and C), which are measured as
dehydroxyfenarimol (DHF), in/on grapes and its processed commodities.

860.1380 Storage Stability

MRID No. 468428.der.doc, D. Rate, 12/SEP/2006.

Adequate storage stability data for plants are available.  The maximum
storage interval of the hops samples from harvest to extraction was 294
days.  The storage stability study submitted (Table 4) supports the use
of fenarimol in/on hops.  There was only a 65-68% recovery from samples
frozen for 286 days.  However, the concurrent recoveries and method
validation recoveries ranged from 64% to 94% with an overall average of
78% recovery.  These recoveries show stability for fenarimol, and the
33% drop over time is accounted for in the recommended tolerance by the
maximum residue level (MRL) calculator.  

TABLE 4.	Summary of Storage Conditions 

Matrix (RAC or Extract)	Storage Temp. (°C)	Maximum Storage Duration for
Field-Treated Samples (days)	Interval of Demonstrated Storage Stability
(days)	Fortification Level (ppm)	Storage Stability Recoveries (%)

HOPS	<-18 to <-15	294	286	1.00	68

1.00	65

1.00	67

Although it will not affect the recommendation of the tolerance of
fenarimol residues on hops, the fenarimol residue chemistry database
does not contain storage stability data for livestock.  Storage
stability data for livestock commodities are required to support the
storage intervals used in the livestock feeding studies. 

860.1400 Water, Fish, and Irrigated Crops

This guideline is not germane to this action.

860.1460 Food Handling

This guideline is not germane to this action.

860.1480 Meat, Milk, Poultry, and Eggs

The qualitative nature of the residue in milk and ruminant tissues is
adequately understood.  For the purpose of this registration, since hops
are not items of animal feed, considerations of secondary tolerances in
meat, milk, poultry, and eggs do not apply to this action.  However, it
should be noted that the fenarimol residue chemistry database does not
contain storage stability data for livestock.  Storage stability data
for livestock commodities are required to support the storage intervals
used in the livestock feeding studies.  The registrant is required to
submit the appropriate data upon request of a tolerance for commodities
of animal feed items.

860.1500 Crop Field Trials

MRID No. 468428.der.doc, D. Rate, 12/SEP/2006.

TABLE 5.	Summary of Residue Data from Crop Field Trials with Fenarimol.

Commodity	Total Applic. Rate,

 lb ai/A

 (kg ai/ha)	PHI (days)	Residue Levels (ppm)

	n	Min.	Max.	HAFT*	Median

(STMdR)	Mean

(STMR)	Std. Dev.

Fenarimol

Hops	0.21826 - 0.27431 (0.6349 - 0.7980)	9 - 12	6	0.308	0.742	0.723
0.661	0.568	0.196

IR-4 has submitted field trial data for fenarimol on hops.  Three field
trials were conducted encompassing Regions 11 (Prosser, WA and Parma,
ID) and Region 12 (Hubbard, OR) during the 1998 growing season.  Because
94% of hops are currently grown in Region 11, the Agency recommends that
most of the trials be performed in Region 11.  The number and locations
of field trials are in accordance with those recommended in OPPTS
Guideline 860.1500.

At each test location, the fields were treated with four foliar-directed
applications of Rubigan™ EC at 0.0547 lb ai/A (1X the proposed label
rate).  Each treatment was applied to hop bines for a total of
approximately 0.22 lb ai/A.  In the Idaho trial, a fifth application was
added to allow the cones to mature.  A total of approximately 0.27 lb
ai/A was applied in the Idaho trial (0.0547 lb ai/A above the label
maximum).  No adjuvant was added to the spray mixture.  Hops were
harvested at 9 to 12 days PHI. 

IR-4 conducted the sample analysis for residues of fenarimol.  The
procedure used was derived from DowElanco: Letcombe Laboratory method,
“Determination of Fenarimol Residues in Fresh, Dried and Spent
Hops.”  Briefly, the residues were extracted from the samples using
methanol, purified by sodium bicarbonate and methyl tert-butyl ether
liquid/liquid partition and subjected to alumina column clean-up prior
to analysis using gas chromatography (GC) with an electrolytic
conductivity detector (ECD).  The lowest level of method validation
(LLMV) in this study was 0.100 ppm fenarimol.  The limit of quantitation
(LOQ) for the method was 0.12 ppm, and the limit of detection (LOD) was
0.041 ppm, approximately one-third of the LOQ.  

Samples were extracted and analyzed on the same day.  Analytical sets
typically consisted of calibration standards, unfortified controls,
fortified controls, and treated samples.  The analytical standard
solutions were stored frozen (-20 ± 6°C).  

The results from the three trials show that the maximum residues in hops
(cones) following a total application of approximately 0.22 lb ai/A and
a pre-harvest interval (PHI) of 9 to 12 days was 0.742 ppm (98-OR11
(Hubbard, OR)).  In Idaho, where approximately 0.2743 lb ai/A was
applied, the residues were 0.661 ppm and 0.627 ppm.  Residues of
fenarimol have been shown to be stable for the duration of storage (286
days) that occurred during the conduct of this study, with a reported
recovery of 65-68%.  Residue decline data were not provided with this
study of fenarimol residues on hops.

Conclusions.  The study reflects a 1X use pattern on hops as directed by
the proposed label.  The residue data are supported by the storage
stability study.  The analytical methods are adequate to determine the %
fenarimol, per se in hops.  The requested tolerance level is supported
by the submitted residue data, based on the MRL calculator (See
Attachment 2).  The study included adequate recovery/method validation
data ranging from 64%-94% recoveries.  Adjustments for the 33% loss in
storage stability residue recovery (Table 4) are incorporated in the
calculated tolerance made by the MRL spreadsheet.  That is, the
calculated tolerance is high enough that when even the highest field
trial value (0.742 ppm) is adjusted for residue decay, the resulting
value (1.1 ppm) is still less than the tolerance value.  The requested
tolerance level of 1.2 ppm for fenarimol on hops is supported by the
submitted field trial data.  

860.1520 Processed Food and Feed

There are no processed food and feed from hops.  This guideline is not
germane to this action.

860.1650 Submittal of Analytical Reference Standards

The previously submitted 0.5 gram sample has expired.  The Agency
requests a 5 gram sample be submitted to the Agency Pesticide Repository
by Gowan.  

860.1850 Confined Accumulation in Rotational Crops

There are no rotational crops germane to this action

860.1900 Field Accumulation in Rotational Crops

There are no rotational crops germane to this action.

860.1550 Proposed Tolerances

DP Num: 277692, D. Drew, 17/SEP/2001 

The MARC decision suggested that the Agency request, not require,
additional crops to determine residues of parent and both metabolites (B
and C).  Therefore, the proposed tolerance expression as determined by
the MARC on hops, is for fenarimol, per se.  Tolerances for fenarimol
are listed in 40 CFR 180.421 for fenarimol per se and fenarimol plus
metabolites B and C.  Currently there are no international MRLs or Codex
residue limits for the subject commoditiy.

TABLE 6.  Tolerance Summary for Fenarimol.

Commodity	

Established/Proposed Tolerance (ppm)	

Recommended Tolerance (ppm)	

Comments (correct commodity definition)

Hops	

1.2	

1.2	

Hops cones, dried

Attachment 1:

Chemical Structures of Fenarimol, Metabolite B and Metabolite C:

Common Name

Chemical Structure

Chemical Name	

	Common Name

Chemical Structure

Chemical Name	Common Name

Chemical Structure

Chemical Name	

Fenarimol

	

	Metabolite B (Compound 212746) 

	Metabolite C (Compound 210302)

[alpha-(2 chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol]

[alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-1,4-dihydro-5-pyrimidinem
ethanol]
[5-[2-chlorophenyl)-(4-chlorophenyl)methyl]-3,4-dihydro-4-pyrimidinol]

Attachment 2:  Residue Calculator Results

Residues

0.331

0.308

0.742

0.704

0.694

0.627

Data: 

	Regulator:	EPA	 

	Chemical:	Fenarimol	 

	Crop:	Hops	 

	PHI:	10 Days	 

	App. Rate:

 

	Submitter:

 

	 

 

	n:	6	 

	min:	0.31	 

	max:	0.74	 

	median;	0.66	 

	average:	0.57	 

	 	 	 

	95th Percentile	99th Percentile	99.9th Percentile

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EU Method I

Log Normal	1.1	1.4	1.9

	(2.5)	(4.5)	(--)

EU Method II

Distribution-Free	 	1.5	 

	 	 	 

California Method

μ + 3σ	 	1.2	 

	 	 	 

UPLMedian95th	 	8.0	 

 	 

 

Approximate Shapiro-Francia Normality Test Statistic	 	0.7842	 

	 	0.05 >= p-value > 0.01 : Reject lognormality assumption	 

	 	 	 

Attachment 3:

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name:  

α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol	Common
Name: Fenarimol

	X Proposed tolerance

( Reevaluated tolerance

( Other	Date:  18/SEP/2006

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

( No Codex proposal step 6 or above

( No Codex proposal step 6 or above for the crops requested	Petition
Number:  6E7074

DP Num:  331894

Other Identifier:

Residue definition (step 8/CXL): 

fenarimol	Reviewer/Branch:  Debra Rate/RIMUER Branch

	Residue definition: fenarimol
[alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol] and
its metabolites
[alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-1,4-dihydro-5-pyrimidinem
ethanol and 5-[(2-chlorophenyl)
(4-chlorophenyl)methyl]-3,4-dihydro-4-pyrimidinol measured as the total
of fenarimol and 5-[(2-chlorophenyl)-(4-chlorophenyl)methyl]pyrimidine

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

Hops, dry	5.	Hops

	Limits for Canada	Limits for Mexico

X   No Limits

(No Limits for the crops requested	(No Limits

X No Limits for the crops requested

Residue definition: N/A

	Residue definition:  fenarimol

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S.Funk, 09/18/2006

Fenarimol	Summary of Analytical Chemistry and Residue Data	DP Num: 
331894

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