Document ID: EPA-HQ-OPP-2009-0012-0006
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2009-09-02T04:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

	OFFICE OF PREVENTION, PESTICIDE

	AND TOXIC SUBSTANCES

  SEQ CHAPTER \h \r 1 MEMORANDUM

Date:  10/JUNE/2009

SUBJECT:	Methoxyfenozide.  Petition for Uses and Tolerances on the
Citrus Crop (Group 10), Dried Shelled Peas and Beans, except Soybean
(Subgroup 6C), Popcorn, and Pomegranate.  Summary of Analytical
Chemistry and Residue Data.  

PC Code:  121027	DP Barcode:  D358341

Decision No.:  400821	Registration No.:  62719-442

Petition No.:  8E7447	Regulatory Action:  Section 3 Registration

Risk Assessment Type:  None	Case No.:  NA

TXR No.:  None	CAS No.:  161050-58-4

MRID No.:  47556401 and 47556402	40 CFR:  180.544

		              									Ver.Apr.08

FROM:	Debra Rate, Ph.D., Biologist  SEQ CHAPTER \h \r 1 

		Alternative Risk Integration and Assessment (ARIA)

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

		Registration Division (RD; 7505P)

THROUGH:	William Cutchin, Acting Senior Branch Scientist

		ARIA/RIUMERB/RD (7505P)

		Michael A. Doherty, Ph.D., Chemist

Risk Assessment Branch II (RAB2)

Health Effects Division (7509P)

TO:		Susan Stanton, Environmental Specialist  SEQ CHAPTER \h \r 1   SEQ
CHAPTER \h \r 1 

		Minor Use

		RIMUERB/RD (7505P)

  SEQ CHAPTER \h \r 1 This document was originally prepared under
contract by Dynamac Corporation (submitted 13/FEB/2009).  The document
has been reviewed by ARIA/RD and revised to reflect current Office of
Pesticide Programs (OPP) policies.

Executive Summary

Methoxyfenozide (benzoic acid, 3-methoxy-2-methyl-,
2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl) hydrazine) is a
diacylhydrazine insecticide used on wide variety of food and feed crops
for the control of lepidopterous pest species.  A 22.6% flowable
concentrate (2 lb/gal FlC) and an 80% wettable powder (WP) are
registered to Dow AgroSciences for use as repeated foliar applications
to field, vegetable, fruit, and tree nut crops using ground or aerial
equipment at rates of 0.06-0.25 lb ai/A/application, for maximum
seasonal rates of 0.75-1.0 lb ai/A.  The labeled pre-harvest intervals
(PHIs) range from 1 to 30 days.  

Permanent tolerances are established for residues of methoxyfenozide per
se in/on a wide variety of plant commodities at levels ranging from 0.05
ppm in/on field corn grain and sweet corn ears to 160 ppm in/on soybean
aspirated grain fractions [40 CFR §180.544(a)(1)].  Permanent
tolerances are also established for residues of methoxyfenozide per se
in milk, meat, and fat of livestock [40 CFR §180.544(a)(1)], and for
the combined residues of parent and its glucuronide conjugate
(RH-141,518) in eggs and meat byproducts at 0.02-0.40 ppm [40 CFR
§180.544(a)(2)].  Tolerances have also been established for inadvertent
or indirect residues of methoxyfenozide per se in high-moisture
rotational crops and for the combined residues of methoxyfenozide, its
phenol metabolite (RH-117,236), and its glucoysl conjugates (RH-151,055
and RH-152,072) in low-moisture rotational crops [40 CFR §180.544(d)(1
and 2)]. 

The Interregional Research Project No. 4 (IR-4) has submitted a petition
proposing the use of the 2 lb/gal FlC formulation of methoxyfenozide
(Intrepid® 2F; EPA Reg. No. 62719-442) for control of lepidopterous
pest species on dry peas and beans, citrus fruits (grown west of the
Mississippi River), pomegranates, and popcorn.  The proposed uses on dry
peas and beans, citrus fruits, and pomegranates are for repeated foliar
applications during fruit development at up to 0.25 lb ai/A/application,
for a maximum of 1.0 lb ai/A/season.  The proposed use on popcorn is for
repeated foliar applications at up to 0.12 lb ai/A/application, with a
maximum of 1.0 lb ai/A/season.  The minimum retreatment intervals (RTIs)
are 5 days for popcorn, 7 days for dry peas and beans, 10 days for
pomegranate, and 14 days for citrus fruits.  The minimum preharvest
intervals (PHIs) are 1 day for citrus fruits, 7 days for dry peas and
beans and pomegranates, and 21 days for popcorn.  Applications can
include the use of an adjuvant for all of the proposed uses, except dry
peas and beans, and can be made using ground or aerial equipment, with
the exceptions of citrus fruit for which only ground applications are
allowed.  In conjunction with these uses, IR-4 is proposing the
following permanent tolerances for methoxyfenozide:

Pea and bean, dried shelled, except soybean, subgroup 6C	0.35 ppm

Pomegranate	0.6 ppm

Corn, pop, grain	0.05 ppm

Corn, pop, forage	30 ppm

Corn, pop, stover	125 ppm

IR-4 is also proposing permanent tolerances with a regional registration
for methoxyfenozide residues in/on the following citrus commodities:

Fruit, citrus, group 10 	2.0 ppm

Citrus oil 	70 ppm

Based on the acceptable metabolism studies on cotton, apples, grapes,
and rice, t  SEQ CHAPTER \h \r 1 he nature of methoxyfenozide residues
in primary crops is adequately understood.  The HED Metabolism
Assessment Review Committee (MARC) concluded that the residue of concern
for both the tolerance expression and the risk assessment in primary
crops (and drinking water) is methoxyfenozide per se.  The qualitative
nature of methoxyfenozide residues in livestock is also adequately
understood based on available ruminant and poultry metabolism studies. 
The MARC determined that the residue of concern is parent in milk and
ruminant tissues (except meat byproducts), poultry meat and fat.  The
residues of concern in meat byproducts and eggs are methoxyfenozide and
Metabolite RH-141,518.  The methoxyfenozide assessment team concurs with
the previous finding regarding residues of concern.  

 

Adequate high performance liquid chromatography with ultraviolet or mass
spectrometry detection (HPLC/UV or MS) methods are available for
enforcing the current tolerances of methoxyfenozide on primary crops,
rotational crops and animal commodities.  Depending on the plant
commodity, the limit of quantitation (LOQ) for methoxyfenozide in
primary crop commodities is 0.01-0.05 ppm.  In the submitted dry pea and
citrus field trials and orange processing study, residues of
methoxyfenozide were determined using a liquid chromatography with
tandem mass spectrometry (LC/MS/MS) method (Method GRM 02.25, modified),
which was adequately validated in conjunction with the analysis of field
trial and processing study samples.  Except for orange juice and oil,
residues were extracted with methanol:0.1 N hydrochloric acid and
purified using a solid-phase extraction (SPE) cartridge.  Residues in
orange oil and juice were purified directly with a SPE cartridge. 
Residues in each commodity were then analyzed by LC/MS/MS, using
external standards.  The lowest level of method validation (LLMV) was
0.01 ppm for dry peas and 0.05 ppm for each citrus commodity.

Adequate multiresidue method testing data are available for parent and
its regulated metabolites.  Based on these data, the FDA multiresidue
methods are not suitable for analysis of methoxyfenozide and its
regulated metabolites.

In conjunction with the field trials and processing study, the
petitioner submitted adequate storage stability data supporting the
conditions and duration of sample storage.  These data indicate that
methoxyfenozide is stable at ≤-20°C for up to 14 months in dry peas,
20.6 months in citrus fruits, and 13 months in orange dried pulp and
juice.  However, the data on orange oil indicate that there is the
potential for a 24% decline in methoxyfenozide residues after 13 months
of storage.  Therefore, the residue data for citrus oil were corrected
to account for decline during storage.

Adequate field trial data are available from previous petitions
supporting the registered uses of methoxyfenozide (2 lb/gal FlC) on
field corn and avocados.  As the proposed uses on popcorn and
pomegranates are identical to the respective uses on field corn and
avocados, the residue data from the field corn and avocado field trials
will be translated to support the proposed uses and tolerances on
popcorn and pomegranates.

Adequate field trial data are also available supporting the existing
tolerance and uses of methoxyfenozide on dry peas and beans.  Although
two of the submitted dry pea field trials were conducted at 0.5x the
maximum seasonal rate due to weather conditions at the field sites, the
new pea data in conjunction with previously submitted pea data on
black-eyed and southern pea collected at 1x the maximum seasonal use
rate, adequately represent the number and geographic distribution in
accordance with OPPTS guideline 860.1500.

The submitted citrus fruit field trial data are also inadequate due to
insufficient geographic representation.  Only six citrus field trials
were submitted (2 each on orange, lemon and grapefruit).  Although the
submitted field trials are acceptable, a total of 11 citrus field trials
(4 orange, 4 lemon, and 3 grapefruit) are required to support a regional
use on citrus fruits grown west of the Mississippi River.  Additional
citrus field trials are required as a condition of registration. 

The submitted orange processing study is adequate and indicates that
methoxyfenozide residues do not concentrate in juice (<0.2x) and
concentrated only slightly in dried pulp (1.1x); therefore separate
tolerances are not required for these citrus commodities.  However,
methoxyfenozide residues concentrated by 56x in orange oil, when samples
were corrected for potential residue decline during storage.  Based the
processing factor for oil and the highest average field trial (HAFT)
residues on citrus fruits (1.67 ppm), the maximum expected residues in
oil would be 93.5 ppm.  Therefore, a tolerance of 100 ppm would be
appropriate for citrus oil. 

Adequate livestock feeding studies are available for methoxyfenozide,
and tolerances for livestock commodities were recently reassessed in
conjunction with petitions for uses on grasses, peanuts, alfalfa and
clover.  As the proposed uses do not alter the dietary burden of
livestock to methoxyfenozide residues, reassessment of livestock
tolerances is not required for this petition.

The nature of methoxyfenozide residues in rotational crops is adequately
understood, based on the adequate confined accumulation study. 
Methoxyfenozide is extensively metabolized in rotational crops.  HED has
determined that the residues of concern (for risk assessment) in
rotational crops are methoxyfenozide and its Metabolites designated as
RH-152,067, RH-131,157, and RH-152,071 and free and conjugated forms of
Metabolite RH-117,236, including its glucose conjugate (RH-151,055) and
its malonylglycosyl conjugate (RH-152,072).  

Adequate limited and extensive rotational crop field trials are
available for methoxyfenozide, and these field trials support the
rotational crop restrictions currently on methoxyfenozide labels.  As
the maximum seasonal use rate being proposed for dry peas/beans and
popcorn (1.0 lb ai/A) is the same as for other registered field and
vegetable crops, no changes are required in the current rotational crop
restrictions or tolerances.  Pomegranate and citrus commodities are not
rotated.

 

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

Although additional field trial data are required for citrus fruits
(oranges (2 field trials, one in each of EPA growing Regions 6 and 10),
lemons (2 field trials in EPA growing Region 10), and grapefruits (1
field trial in EPA growing Region 10)) as a condition of registration,
this deficiency would not preclude establishing permanent tolerances for
methoxyfenozide on the requested commodities.  Sufficient residue data
are available to support tolerances on citrus fruits and dry beans and
peas.  A registration of methoxyfenozide on popcorn, pomegranate, dry
peas and beans and a conditional registration on citrus fruits are
recommended pending submission of the following data requirements:

The use directions for popcorn should be amended to specify a 21-day PHI
for harvest of grain and stover.  A PHI is not required for popcorn
forage as it is not a regulated raw agricultural commodity (RAC).

The label should be revised to restrict the use of adjuvants on pea, dry
seed and bean, dry seed (except soybean).

A revised Section F is required increasing the proposed tolerances for
citrus fruit to 10 ppm and citrus oil to 100 ppm.  The Section F should
also be revised to remove the request for a tolerance of 0.35 ppm in/on
dry peas and beans, except soybean (subgroup 6C) and replace the request
to pea, dry seed at 2.5 ppm.  The Section F should also be revised to
remove the request for a tolerance in/on corn, pop, forage.

ARIA recommends for establishing the following permanent tolerances for
methoxyfenozide:  0.6 ppm for pomegranate; 0.05 ppm for popcorn grain;
125 ppm for popcorn stover; 2.5 ppm for pea, dry seed; 10 ppm for citrus
fruits; and 100 ppm for citrus oil.  A tolerance of popcorn forage is
not required, and ARIA notes that once a tolerance is established for
pea, dry seed, the existing tolerances on pea, black-eyed, seed and pea,
southern, seed can be deleted.  A human health risk assessment for
methoxyfenozide is forthcoming.

Background

Methoxyfenozide is a diacylhydrazine insecticide used on a variety of
crops for control of armyworms and other lepidopterous pest species. 
Methoxyfenozide mimics the action of the molting hormone of
lepidopterous larvae, causing the larvae to undergo an incomplete and
premature molt, which ultimately results in their death. 
Methoxyfenozide is currently registered to Dow AgroSciences.  The
nomenclature and physicochemical properties of methoxyfenozide are
presented below in Tables 1 and 2.

-butyl-N′-(3-methoxy-o-toluoyl)-3,5-xylohydrazide

CAS name	3-methoxy-2-methylbenzoic acid
2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazide

CAS registry number	161050-58-4

End-use product (EP)	2 lb/gal FlC (Intrepid ® 2F; EPA Reg., No
62719-442)

Table 2.	  Physicochemical Properties of Methoxyfenozide.

Parameter	Value	Reference

Melting point/range	206.1-208ºC	DP# 231303, H. Podall, 19/MAY/1997

pH	7.0

	Density	0.740 ± 0.0081 g.cm3

	Water solubility (mg/L at 20ºC)	3.3

	Solvent solubility (g/L at 20ºC)	N-heptane	1.87

Xylene	3.38

1,2-dichloroethane	36.72

Methanol	192.92

2-Propanol	50.22

	Vapor pressure at 25ºC	1.33 x 10-5 Pa

	Dissociation constant, pKa	None

	Octanol/water partition coefficient, Log(KOW)	3.72 ± 0.04

	UV/visible absorption (max)	ε 55313 at 203 nm	European Commission,
SANCO/10384/202 – rev. 4, 10/07/2004.

860.1200  Directions for Use

Methoxyfenozide is currently registered to Dow AgroSciences for use on a
wide variety of food and feed crops as a 2 lb/gal FlC formulation
(Intrepid( 2F, EPA Reg. No. 62719-442).  IR-4 is proposing new uses for
this formulation on citrus fruits (crop group 10), dry peas and beans,
except soybeans (subgroup 6C), pomegranate, and popcorn.  Examples of
supplemental labels for the 2 lb/gal FlC were provided, and the proposed
use directions are summarized below in Table 3.

Table 3.	Summary of Directions for Use of Methoxyfenozide.

Applic. Timing, Type, and Equip. 1	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 2

Citrus, Crop Group 10

Foliar applications at first sign of pests. Ground equipment only.	2
lb/gal FlC [62719-442]	0.12-0.25	NS (not specified)	1.0	1	The minimum
RTI is 14 days. 

Apply in a minimum of 50 gal/A.  For use only in States west of the
Mississippi River.

Dry Peas and Beans

Foliar applications at first sign of feeding damage. Ground or aerial
equipment.	2 lb/gal FlC [62719-442]	0.06-0.25	4	1.0	7	The minimum RTI is
7 days. 

Apply in a minimum of 10 gal/A

Pomegranate

Foliar applications beginning at egg hatch or at first signs of
infestation;

Ground or aerial equipment.	2 lb/gal FlC [62719-442]	0.12-0.25	NS 	1.0	7
The minimum RTI is 10 days. 

Apply in a minimum of 20 and 50 gal/A using aerial or ground equipment,
respectively.

Do not use in New York State.

Pop Corn

Foliar applications beginning at egg hatch or at first signs of
infestation;

Ground or aerial equipment.	2 lb/gal FlC [62719-442]	0.06-0.12	NS 	1.0	3
(ears, forage), 21 (dry fodder)	The minimum RTI is 5 days.

Apply in a minimum of 10 gal/A.

Do not use in New York State.

1	The main label prohibits applications through any type of irrigation
system, and allows for the inclusion of adjuvants in the spray mix.

2	For the uses on dry peas and beans and popcorn the following
rotational crop restrictions are specified:  Crops with registered uses
may be replanted at any time, and all other food or feed crops may be
replanted 7 days after the last application.

Conclusions.  The supplemental label directions are adequate to allow
for evaluation of the residue data relative to the submitted field
trials.  The available field trial and rotational crop data support the
proposed use directions, with the exception of the proposed PHIs for
popcorn.  The proposed PHIs for popcorn appear to have been
inadvertently taken from the sweet corn use directions, rather than from
the field corn use directions.  The use directions for popcorn should be
amended to specify a 21-day PHI for harvest of grain and stover.  A PHI
is not required for popcorn forage as it is not a regulated RAC.  The
supplemental label for dry peas and beans, except soybean (subgroup 6C)
should be revised to restrict the use of adjuvants.  

860.1300 Nature of the Residue - Plants

MARC Memo, DP# 258034, W. Wassell, 23/JUL/1999

DP# 251225, W. Wassell, 27/JUL/1999

DP# 259989, W. Wassell, 08/AUG/2000

  SEQ CHAPTER \h \r 1 The nature of methoxyfenozide residues in primary
crops is adequately understood, based on acceptable metabolism studies
in cotton, apples, grapes, and rice.  Methoxyfenozide does not undergo
extensive metabolism in primary crops.  The MARC has determined that the
residue of concern for both the tolerance expression and the risk
assessment in primary crops (and drinking water) is methoxyfenozide per
se. 

860.1300 Nature of the Residue - Livestock

MARC Memo, DP# 258034, W. Wassell, 23/JUL/1999

The nature of the residue in ruminants is adequately understood, based
on the available metabolism studies in lactating goats and hens.  HED
has determined that the residue of concern in milk and ruminant tissues
(other than liver and kidney) is parent compound; in ruminant liver and
kidney it is methoxyfenozide and its RH-141,518 metabolite.  The residue
of concern in poultry meat (muscle) and fat is parent methoxyfenozide. 
The residue of concern in eggs, poultry liver, and poultry meat
byproducts is methoxyfenozide and its metabolite RH-141,518.

860.1340 Residue Analytical Methods

Enforcement methods for plant commodities.  The following HPLC/UV (or
MS) methods are available for enforcing tolerances of methoxyfenozide on
primary crops:  Method TR 34-96-88 for cotton commodities; Method TR
34-98-87 for pome fruits; Method TR 34–00-38 for corn commodities;
Method TR 34-00-107 for tree nuts; Method TR 34-00-109 for stone fruits;
and Method TR 34-99-74 for leafy and Brassica (cole) vegetables,
fruiting vegetables, grapes and raisins.  Adequate method validation,
radiovalidation, and independent laboratory validation data have been
provided for these methods.  Successful petition method validation (PMV)
trials were conducted on Methods TR 34-96-88 and TR 34-98-87, and the
Analytical Chemistry Branch (ACB) concluded that PMV trials were not
required for the other methods as they are similar to the validated
methods.

For each of these methods, residues of methoxyfenozide are extracted
with acidic aqueous methanol, filtered and diluted with 10% sodium
chloride.  Extracts are then purified by sequential liquid-liquid
partitioning with hexane and dichloromethane (DCM).  Residues in the DCM
fraction are further purified by elution through one or more of the
following column types:  basic alumina, silica gel, carbon, Florisil, or
C18.  Residues in the final eluate are concentrated, redissolved in
acetonitrile:water, and analyzed by reverse-phase HPLC using UV (240 nm)
or MS (m/z 367) with external standards.  The LOQ for methoxyfenozide is
0.01-0.05 ppm depending on the plant commodity.

An adequate enforcement method is also available for determining the
residues of concern in rotated crops.  Method TR 34-00-41 includes an
HPLC/UV method that determines residues of methoxyfenozide in
high-moisture rotational crops; and a HPLC/MS method that determined
residues of methoxyfenozide and its metabolites RH-117,236, RH-151,055,
and RH-152,072 (determined at RH-151,055) in low-moisture rotational
crops.  Adequate method validation, radiovalidation, and ILV data have
been submitted for this method, and ACB concluded that a PMV trial was
not needed for this method owing to its similarity to Method TR
34-98-87.

Data collection methods for plant commodities.  Residues of
methoxyfenozide in/on dry peas, citrus fruits, and processed orange
commodities were determined using an LC/MS/MS method, which is a
modified version of Method GRM 02.25, “Determination of Residue of
Methoxyfenozide in High Moisture Crops by Liquid Chromatography with
Tandem Mass Spectrometry Detection.”  This method was previously
reviewed in conjunction with a petition for use on soybeans (DP# 316528,
W. Cutchin, 25/APR/2006).  

For this method, methoxyfenozide residues in/on dry peas, citrus fruits
and dried citrus pulp were first extracted with methanol:0.1N
hydrochloric acid (90:10, v/v), filtered and concentrated.  Residues
were then cleaned up using a Phenomenex Strata-X SPE column.  For citrus
juice, residues were directly purified using the solid phase extraction
(SPE) cartridge.  After loading the sample, the SPE cartridge was washed
with a 60% water/40% methanol/0.1% formic acid solution, and residues
were then eluted with acetonitrile.  For citrus oil, the sample was
initially diluted with hexane and then cleaned up using silica gel SPE. 
The silica SPE cartridge was washed with hexane and then 10% ethyl
acetate in hexane, and residues were then eluted with 40% ethyl acetate
in hexane.  The eluates from the SPE cartridges were evaporated to
dryness, and the residues were reconstituted in acetonitrile:10 mM
ammonium acetate (50:50, v/v) for analysis.  The samples were analyzed
by LC/MS/MS using external standards.  The m/z 339→149 ion transition
was used for quantitation of residues.  The LLMV was 0.01 ppm for dry
peas and 0.05 ppm for each citrus commodity (0.2 ppm for citrus oil). 
The statistically calculated LOQs were 0.012 ppm for dry peas, 0.021 ppm
for citrus fruit, 0.018 ppm for dried pulp, 0.009 ppm for juice, and
0.067 ppm for oil.  The calculated limit of detection (LOD) was 0.004
ppm for dry peas, 0.007 ppm for citrus fruit, 0.006 ppm for dried pulp,
0.003 ppm for juice, and 0.022 ppm for oil.  

The above method was adequately validated using control samples of each
matrix fortified with methoxyfenozide at 0.01-1.0 ppm for dry peas,
0.05-5.0 ppm for citrus fruits, dried pulp, and juice, and 0.2-10.0 ppm
citrus oil.  Acceptable recoveries were obtained for each matrix, and
the fortification levels bracketed the measured residue levels. 
Apparent residues of methoxyfenozide were non-detectable in/on all
control samples.

Conclusions.  The available HPLC/UV (or MS) methods are adequate for
enforcing the established and recommended tolerances, and residues in/on
citrus and dry pea commodities were determined using adequate data
collection methods.

860.1360 Multiresidue Methods

PP# 8F5004 & PP#8F5006, DP# 249438, 249458, 251218, & 251225, W.
Wassell, 27/JUL/1999 

Data concerning the recovery of methoxyfenozide per se using the FDA
multiresidue method protocols (PAM Vol. I) were previously submitted to
and reviewed by HED.  Methoxyfenozide was not recoverable by any of
these procedures.  The data were forwarded to FDA for evaluation and the
updating of PAM Vol. I.

860.1380 Storage Stability

DP#s 249438, 249458, 251218, & 251225, W. Wassell, 27/JUL/1999

DP# 259989, M. Doherty, 08/AUG/2000

DP# 269986 & 274542, M. Nelson, 07/AUG/2002

DP# 331948, W. Cutchin, 18/DEC/2007

Adequate storage stability data are available indicating that
methoxyfenozide is stable under frozen storage conditions for up to 32
months in grass forage and hay; 23.5 months in cottonseed; 22 months in
avocados; 20 months in green onions; 14 months in sweet potatoes and
peanut commodities (nutmeat, hay, meal and oil); 13 months in corn
grain; 12 months in cottonseed oil and gin trash, tomatoes, leaf lettuce
and apples; 10.5 months in apple juice and wet pomace and dry beans; 6
months in corn oil and corn meal; and 1.5 months in guavas.  

In addition, concurrent storage stability studies were conducted with
the submitted citrus fruit field trials and processing study and the dry
pea field trials.  In each field trial, control samples were fortified
with methoxyfenozide at 0.1 ppm (dry peas) or 1.0 ppm (citrus fruits and
orange processed fractions).  The fortified samples were then placed in
storage under the same conditions (-20°C) as the field trial and
processing study samples.  No 0-day analyses were conducted on the
fortified samples placed into storage.  At the end of the analytical
phase of each study, the stored samples were analyzed in triplicate
along with control samples freshly fortified with methoxyfenozide at the
same level.  Following frozen storage, the average corrected recovery of
methoxyfenozide was 99% from dry peas after 436 days, 99% from oranges
after 629 days, 103% from dried pulp after 405 days, 109% from orange
juice after 403 days, and 76% from orange oil after 400 days.  Although
no 0-day analysis was conducted, the data indicate that methoxyfenozide
is stable at -20°C for up to 14 months in dry peas, 20.6 months in
citrus fruits, and 13 months in orange dried pulp and juice.  However,
the data on orange oil indicate that there is the potential for a 24%
decline in methoxyfenozide residues after 13 months of storage.

The storage durations and conditions for samples from the crop field
trials and processing study submitted to support this petition are
presented in Table 4.  

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

Matrix 	Storage Temperature  (°C)	Actual Storage Duration (days)
Interval of Demonstrated Storage Stability (days)

Dry pea	<-20	410-448	426

Oranges

407-658	629 (orange)

Lemons

616-621	629 (orange)

Grapefruits

650-657	629 (orange)

Orange, dried pulp

411	405

Orange, juice

413	403

Orange, oil

420	400

rage (↓24% after 13 months), the residue data for citrus oil will be
corrected to account for decline during storage.

860.1400 Water, Fish, and Irrigated Crops

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

860.1460 Food Handling

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

860.1480 Meat, Milk, Poultry, and Eggs

Adequate livestock feeding studies are available for methoxyfenozide
(DP# 269969, M. Nelson, 07/AUG/2002), and methoxyfenozide residues in
animal commodities were recently reassessed in conjunction with
petitions for uses on grass, peanuts, alfalfa and clover (DP# 331948, W.
Cutchin, 18/DEC/2007).  The maximum dietary burdens (MDB) of livestock
for methoxyfenozide residues were calculated at that time to be 34.7 ppm
for beef cattle, 50.7 ppm for dairy cattle, 7.8 ppm for poultry, and
0.22 ppm for swine.

The only new livestock feedstuffs associated with the proposed uses are
popcorn grain and stover, which have the same tolerances as field corn
grain and stover.  Based on recent changes in Agency guidance on
calculating residues in reasonably balanced livestock diets (memo, June,
2008), the MDB for livestock to methoxyfenozide residues was
recalculated to be 35 ppm for beef cattle, 54 ppm for dairy cattle, 7.7
ppm for poultry and 0.19 ppm for swine (Table 5).  As the proposed uses
do not alter the dietary burden for livestock to methoxyfenozide
residues, reassessment of livestock tolerances is not required for this
petition. 

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

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

Beef Cattle

Alfalfa, hay	R	89	15	150	25.28

Corn, field, grain	CC	88	75	0.05	0.043

Soybean, asp. grain fractions	CC	85	5	160	9.412

Soybean, seed	PC	89	5	1.00	0.056

TOTAL BURDEN	--	--	100	--	34.79

Dairy Cattle

Grass, forage	R	25	25	18	18.00

Alfalfa, hay	R	35	20	150	33.71

Apple, wet pomace	CC	40	10	7.0	1.75

Corn, field, grain	CC	88	35	0.05	0.020

Cotton, undelinted seed	PC	88	10	2.00	0.227

TOTAL BURDEN	--	--	100	--	53.71

Poultry

Corn, field, grain	CC	88	75	0.05	0.038

Alfalfa, meal 4 	PC	89	5	150	7.50

Soybean, meal 4	PC	92	20	1.00	0.200

TOTAL BURDEN	--	--	100	--	7.74

Swine

Corn, field, grain	CC	88	85	0.05	0.043

Soybean, meal 4	PC	92	15	1.00	0.150

TOTAL BURDEN	--	--	100	--	0.193

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.

4	Residues in alfalfa meal are based on tolerance for alfalfa hay, and
residues in soybean meal are based on the tolerance for soybean seeds.

860.1500 Crop Field Trials

47556401.de1 (Citrus fruit field trials), D. Rate, 05/MAR/2009

47556402.der (Dry pea field trials), D. Rate, 16/MAR/2009

PP# 6E7086, DP# 331948, W. Cutchin, 18/DEC/2007 (Dry bean and avocado
field trials)

DP# 269969, M. Nelson, 07/AUG/2002 (Field corn field trials)

IR-4 has submitted new field trial data supporting the proposed uses of
methoxyfenozide (2 lb/gal FlC) on citrus fruits and dry peas.    SEQ
CHAPTER \h \r 1 The results from these field trials are discussed below
and the residue data are summarized in Table 6.  As IR-4 is seeking a
tolerance on the dry pea and bean subgroup 6C, the previously reviewed
field trial data on dry beans (DP# 331948, W. Cutchin, 18/DEC/2007),
which support the current 0.24 ppm tolerance on dry beans, are also
discussed below and summarized in Table 6.  In addition, IR-4 is
proposing uses on pomegranates and popcorn, and has requested that the
existing residue data from avocado and field corn be used to support
these uses.  The available residue data on avocado and field corn are
also discussed below. 

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

Crop matrix	Total Applic. Rate (lb ai/A)	PHI (days)	Residue Levels (ppm)
1

	n	Min.	Max.	HAFT 2	Median	Mean	Std. Dev.

Citrus fruits, grown west of the Mississippi River 

(proposed use = 1.0 lb ai/A total application rate, 1-day PHI)

Orange	1.00-1.01	1	4	0.140	1.72	1.670	0.894	0.912	0.876

Lemon 	1.00	1	4	0.374	0.933	0.792	0.529	0.591	0.259

Grapefruit	1.00-1.02	1	4	0.112	0.278	0.254	0.173	0.184	0.083

Dry pea and bean, Crop subgroup 6C (proposed use = 1.0 lb ai/A total
application rate, 7-day PHI)

Dry peas	0.97-1.00	6-7	8	0.062	0.171	0.170	0.134	0.124	0.047

Dry peas	0.499-0.502	7	4	0.039	0.063	0.056	0.047	0.049	0.010

Dry peas3 	1.0 lb ai/A	7-8	12	0.098	3.39	2.70	0.337	0.70	1.0

Dry beans 3	0.97-1.04	6-8	26	<0.05	0.22	0.15	0.05	0.057	0.033

1	The LLMV for methoxyfenozide is 0.05 ppm in citrus fruits and dry
beans and 0.01 ppm for dry peas.

2  HAFT = Highest average field trial result.

3  Data for this data set from DP# 287827, M. Nelson, 04/FEB/2003.

4	Data for dry beans from DP# 331948, W. Cutchin, 12/18/07.

Citrus, Crop Group 10

Orange, Lemon, and Grapefruit.  In six field trials (2 each on orange,
lemon, and grapefruit) conducted in the EPA growing Regions 6 and 10
during 2005 and 2006, methoxyfenozide (2 lb/gal FlC) was applied to
citrus trees as four directed foliar applications during fruit
development at rates of 0.249-0.258 lb ai/A/application and RTIs of
13-21 days, for totals of 1.00-1.02 lb ai/A (1x seasonal rate). 
Applications were made using ground equipment in volumes of 61-129
gal/A, and a non-ionic surfactant was included in the spray mixture at
0.02-0.13% v/v.  Duplicate control and treated samples of citrus fruits
were harvested from each field trial at commercial maturity, 1 day after
treatment (DAT).

Citrus fruit samples were stored at <-20°C for up to 21.9 months prior
to extraction for analysis, and the sample storage conditions and
duration are supported by the available storage stability data. 

Residues of methoxyfenozide in/on citrus fruits were determined using an
adequate LC/MS/MS method (GRM 02.25, modified), which was validated in
conjunction with the analysis of field trial samples.  The lowest level
of method validation (LLMV) was 0.05 ppm, and the statistically
calculated LOQ and LOD were 0.021 ppm and 0.007 ppm, respectively.

Following four foliar applications of methoxyfenozide to citrus trees at
rates totaling ~1.0 lb ai/A (1x rate), methoxyfenozide residues at 1 DAT
were 0.140-1.72 ppm in/on 4 orange samples, 0.374-0.933 ppm in/on 4
lemon samples, and 0.112-0.278 ppm in/on 4 grapefruit samples.  The
average residues in/on oranges, lemons, and grapefruits were 0.912,
0.591 and 0.184 ppm, respectively.  The highest average field trial
(HAFT) residues for oranges, lemons, and grapefruits were 1.67, 0.792,
and 0.254 ppm, respectively.  No residue decline data were provided.

Dried Peas and Beans, except Soybean, Subgroup 6C

Dry Peas.  In six field trials conducted in the EPA growing Regions 5
and 11 during 2006, methoxyfenozide (2 lb/gal FlC) was applied to dry
peas as repeated broadcast foliar applications during seed development
at rates of 0.241-0.254 lb ai/A/application (1x single rate) and RTIs of
6-7 days.  Two applications were made at two field trial sites for a
total of 0.50 lb ai/A (0.5x seasonal rate), and four applications were
made at four field trial sites for a total of 0.97-1.00 lb ai/A (1x
seasonal rate).  All applications were made using ground equipment in
volumes of 24-76 gal/A, and no adjuvants were used.  Single control and
duplicate treated samples of dry peas were harvested at commercial
maturity, 6-8 DAT.  

Dry pea samples were stored at <-20°C for up to 14.9 months prior to
extraction for analysis, and the sample storage conditions and duration
are supported by the available storage stability data. 

Residues of methoxyfenozide in/on dry peas were determined using an
adequate LC/MS/MS method (GRM 02.25, modified), which was adequately
validated in conjunction with the analysis of field trial samples.  The
LLMV was 0.01 ppm, and the statistically calculated LOQ and LOD were
0.012 ppm and 0.004 ppm, respectively.

In the four field trials with total application rates of 0.97-1.00 lb
ai/A (1x rate), methoxyfenozide residues were 0.062-0.171 ppm in/on 8
samples of dry peas harvested at 6-7 DAT.  The average methoxyfenozide
residue was 0.124 ppm and the HAFT residue was 0.170 ppm.  In the two
field trials with total application rates of ~0.5 lb ai/A, residues were
0.062-0.171 ppm in/on 4 samples at 6-7 DAT and averaged 0.049 ppm.  No
residue decline data was provided.

Adequate residue data for pea, black-eyed, seed and pea, southern, seed
were previously submitted by IR-4 in conjunction with an earlier
petition (PP# 3E06528, DP# 287827, M. Nelson, 04/FEB/2003).  In six
field trials conducted in EPA growing Regions 2 and 10 during the 1999
growing season, methoxyfenozide (80%WP) was applied to pea plants as
four foliar spray applications of 0.25 lb ai/A with a 1.0 lb ai/A/season
maximum.  Samples were harvested 7-8 DAT at commercial maturity. 
Detectable levels of methoxyfenozide residues were reported in each of
these six pea trials.  The residues ranged from 0.1 to 3.39 ppm.

Dry beans.  Adequate residue data for dry beans were previously
submitted by IR-4 in conjunction with an earlier petition (PP#6E7086;
DP# 331948, W. Cutchin, 18/DEC/2007).  In 13 field trials conducted in
the EPA growing Regions 1, 5, 7, 9, 10, and 11 during 2002,
methoxyfenozide (80% WP) was applied to beans during pod and seed
development as four broadcast foliar applications at 0.23-0.26 lb
ai/A/application and RTIs of 6-8 days, for a total of 0.97-1.04 lb ai/A
(1x seasonal rate).  All applications were made using ground equipment
in volumes of 15-79 gal/A, and no adjuvants were used.  Single control
and duplicate treated samples of dry beans were harvested at commercial
maturity, 6-8 DAT.  

Dry bean samples were stored at <-20°C for up to 10.5 months prior to
extraction for analysis, and the sample storage conditions and duration
were supported by the available storage stability data. 

Residues of methoxyfenozide in/on dried beans were determined using an
adequate LC/MS/MS method derived from Methods 34-98-87 and 34-96-88. 
The method was adequately validated in conjunction with the analysis of
field trial samples.  The LLMV was 0.05 ppm, and the statistically
calculated LOQ and LOD were 0.046 ppm and 0.020 ppm, respectively.

Following four applications of methoxyfenozide at rates totaling
0.97-1.04 lb ai/A (1x rate), methoxyfenozide residues were <0.05-0.22
ppm in/on 26 samples of dry beans harvested at 6-8 DAT, with 24 of the
26 samples having residues <LOQ (<0.05 ppm).  The average
methoxyfenozide residue was 0.05 ppm and the HAFT residue was 0.15 ppm. 
No residue decline data were provided.

Cereal Grains, Group 15.

Popcorn.  To support the use of methoxyfenozide on popcorn, IR-4 has
proposed translating the existing field corn residue data (DP# 269969,
M. Nelson, 07/AUG/2002) to popcorn.  Field corn data are available from
21 field trials conducted in the EPA growing Regions 1, 2, 5 and 6
during 1998.  In each trial, methoxyfenozide (80% WP) was applied to
field corn as four broadcast foliar applications rates of ~0.25 lb
ai/A/application (2x single rate) and RTIs of 5-18 days, for a total of
~1.0 lb ai/A (1x seasonal rate).  Four of the trial sites also included
side-by-side tests comparing the 2 lb/gal FlC and WP formulations of
methoxyfenozide at equivalent rates.  All applications were made using
ground equipment in volumes of 10-36 gal/A, and included the use of a
non-ionic surfactant.  Single control and duplicate treated samples of
forage were collected from each test at 19-21 DAT, and grain and stover
samples were collected at 20-23 DAT.  In addition, two of the test sites
include repeated sampling of forage, grain and stover at 7-day intervals
from 0 to 28 DAT in order to assess residue decline. 

Samples of field corn forage, grain and stover were stored frozen for
8-17 months prior to extraction for analysis, and the sample storage
conditions and durations are supported by the available storage
stability data. 

Residues of methoxyfenozide in/on each corn commodity were determined
using an adequate LC/MS/MS method (TR 34-98-186), which was adequately
validated in conjunction with the analysis of field trial samples.  The
LOQ was 0.02 ppm for grain and 0.04 ppm for forage and stover, and LOD
was 0.006 ppm for grain and 0.012 ppm for forage and stover.

In the four side-by-side field trials comparing the WP and FlC
formulations, residues in/on field corn forage, grain and stover were
similar between the two formulations.  For all 21 field trials,
methoxyfenozide residues were <0.006-0.033 ppm in/on 50 samples of grain
harvested at 20-23 DAT, with only one grain sample having residues above
the LOQ (>0.02 ppm).  Based on the LOD, the average residues in/on grain
were 0.007 ppm.  For stover, methoxyfenozide residues were 1.28-117 ppm
in/on 50 samples harvested at 20-23 DAT.  The average residue was 23.9
ppm in/on stover and the HAFT residue was 86.5 ppm.  For forage,
methoxyfenozide residues were 0.103-12.3 ppm in/on 50 samples harvested
at 19-21 DAT.  The average residue was 3.27 ppm in/on forage and the
HAFT residue was 9.58 ppm.  Residue data on forage and stover from the
decline trials show that residues declined slightly over time.  These
data support the proposed use on popcorn.  ARIA notes that residue data
for corn forage are not required to support uses on popcorn, as popcorn
forage is not a regulated livestock feedstuff.

Miscellaneous Commodities

Pomegranate.  To support the use of methoxyfenozide on pomegranates,
IR-4 has proposed translating the existing field trial data from
avocados.  The ChemSAC (minutes from 16/JUL/2008 meeting) has concurred
with this proposal as the uses on avocado and pomegranate are identical,
the two crops are grown in the same geographical areas, and both crops
are subtropical plants with inedible peels.

The avocado field trial data were reviewed in an earlier petition (DP#
331948, W. Cutchin, 18/DEC/2007).  In 6 field trials conducted during
2004 in EPA growing Regions 6, 10 and 13, methoxyfenozide (2 lb/gal FlC)
was applied to avocado trees as four foliar applications during fruiting
at rates of 0.248-0.271 lb ai/A (1x single rate), and RTIs of 6-8 days,
for a total of 1.00-1.07 lb ai/A (1x seasonal rate).  Applications were
made using ground equipment at volumes of 76-220 gal/A, and included the
use of a non-ionic surfactant.  Single control and duplicate treated
samples of avocados were harvested from each test at 2-4 DAT.  Samples
were stored frozen for up to 697 days prior to extraction for analysis,
a duration supported by the concurrent storage stability data.  

The LC/MS/MS method used to determine residues of methoxyfenozide in/on
avocados was adequately validated prior to and in conjunction with the
analysis of field trial samples.  The LLMV was 0.01 ppm, and the
statistically calculated LOQ and LOD were 0.006 ppm and 0.002 ppm,
respectively.

Following four broadcast foliar applications of methoxyfenozide totaling
1.00-1.07 lb ai/A (1x rate), residues of methoxyfenozide were 0.03-0.41
ppm in/on 12 samples of avocados harvested at 2-4 DAT.  The average
residue was 0.15 ppm and the HAFT residue was 0.36 ppm.  No residue
decline data were collected.

Conclusions.  The submitted citrus fruit field trial data are inadequate
due to insufficient geographic representation.  To support a regional
use on citrus fruits grown west of the Mississippi River, four trials
are required each for lemons and oranges, and 3 field trials are
required for grapefruits.  However, only two field trials were submitted
for each type of citrus fruit.  As a condition of registration,
additional field trials are required on citrus fruits:  two orange
trials in EPA growing Regions 6 and 10, two lemon trials in EPA growing
Region 10, and one grapefruit trial in EPA growing Region 10.  Based on
the submitted data, ARIA recommends for a conditional registration and
tolerance of 10 ppm in/on fruit, citrus, group 10.  The petitioner must
submit a revised Section F to accommodate the above recommendation.

The submitted dry pea field trial data in addition to previously
reviewed dry pea data (DP# 287827, M. Nelson, 04/FEB/2003) are adequate
to support a use on peas, dry seed.  Based on the submitted data, ARIA
recommends for highest MRL calculated tolerance of 2.5 ppm based on the
data submitted for the southern and black-eyed peas. Because the pea,
dry seed tolerance is >10x the current tolerance for bean, dry seed
(except soybean), ARIA cannot recommend for a subgroup 6C tolerance. 
The tolerance for bean, dry seed should remain at 0.24 ppm.  ARIA
recommends that the tolerances for pea, southern, seed and pea,
black-eyed, seed be removed when the pea, dry seed tolerance is
established.  A revised Section F requesting tolerance levels and
definitions to match the Agency’s recommendations should be submitted.
 

Adequate field trial data are available on field corn and avocados.  As
the registered uses on these crops are the same as the respective uses
on popcorn and pomegranates, the residue data on field corn grain and
stover will support the use on popcorn, and the residue data on avocados
will support the use on pomegranates.  ARIA recommends for tolerances of
0.6 ppm in/on pomegranate, 0.05 ppm in/on corn, pop, grain, and 125 ppm
in/on corn, pop, stover.  Because no tolerances are required for corn,
pop, forage, a revised Section F must be submitted to remove this
requested tolerance.

860.1520 Processed Food and Feed

47556401.de2 (orange), D. Rate, 16/MAR/2009

In conjunction with the citrus fruit field trials, IR-4 submitted a
processing study using oranges treated at a ~1x use rate.    SEQ CHAPTER
\h \r 1 The study on oranges is discussed below and the processing
factors for methoxyfenozide residues in orange fruit, dried pulp, juice
and oil are summarized in Table 7.  

  SEQ CHAPTER \h \r 1 Table 7.	Summary of Processing Factors for
Methoxyfenozide.

RAC	Processed Commodity	Processing Factor

Orange	Fruit (RAC)	not applicable

	Dried Pulp	1.1x

	Juice	<0.2x

	Oil	56x

In a field trial conducted in CA during 2006, methoxyfenozide (2 lb/gal
FlC) was applied to orange trees as a single directed foliar spray at
fruit maturity at 0.995 lb ai/A.  This application rate is 4x the
maximum proposed single use rate and 1x the maximum seasonal use rate. 
The application was made using ground equipment in a volume of 100
gal/A, and no adjuvants were used.  Single control and treated bulk
samples of oranges were harvested at 3 DAT, and whole fruits were
processed into dried pulp, juice, and oil using commercial processing
procedures. 

Samples of whole fruit, dried pulp, juice and oil were stored at ≤-20
ºC for 13.4-13.8 months prior to analysis.  The available storage
stability data indicate that methoxyfenozide is stable in frozen citrus
fruit, pulp and juice for this duration, but the study also showed a
potential decline of 24% in methoxyfenozide residues in oil after 13.1
months of frozen storage.  Therefore, the residues in oil were corrected
to account for this decline.

 

Methoxyfenozide residues were determined using an adequate LC/MS/MS
method (GRM 02.25, modified), which was validated in conjunction with
the analysis of processing study samples.  The LLMV was 0.05 ppm for
each matrix, and the statistically calculated LOQs were 0.021 ppm for
whole fruit, 0.018 ppm for dried pulp, 0.009 for juice, and 0.067 ppm
for oil.  The calculated LODs are 0.007, 0.006, 0.003, and 0.022 ppm,
respectively for whole fruit, pulp, juice, and oil. 

Following a single foliar application of methoxyfenozide at ~1.0 lb
ai/A, methoxyfenozide residues were 0.245 ppm in/on orange fruit, 0.269
ppm in dried pulp, <0.05 ppm in juice, and 10.4 ppm in oil.  When
corrected for potential decline during frozen storage, actual residues
in oil were 13.68 ppm.  These data indicate that methoxyfenozide
residues were reduced in orange juice (<0.2x) and concentrated only
slightly in dried pulp (1.1x).  However, residues concentrated
substantially in citrus oil (56x).  The citrus theoretical processing
factors are 2x for juice and dried pulp and 1000x for oil.

Conclusions.  The citrus processing study is adequate and indicates that
separate tolerances are not required for orange juice and dried pulp. 
However, a separate tolerance is required for citrus oil.  Based the 56x
processing factor for oil and the HAFT residue of 1.67 ppm for citrus
fruits, the maximum expected residue in oil is 93.5 ppm.  Therefore, a
tolerance of 100 ppm would be appropriate for citrus oil.  A revised
Section F must be submitted requesting a tolerance of 100 ppm to concur
with ARIA’s recommendation.

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

An analytical standard for methoxyfenozide, with an expiration date of
17/OCT/2011, is currently available in the EPA National Pesticide
Standards Repository (personal communication with Dallas Wright, ACB,
01/DEC/2008).  

860.1850 Confined Accumulation in Rotational Crops

MARC Memo, DP# 258034, W. Wassell, 23/JUL/1999

DP# 251225, W. Wassell, 27/JUL/1999

  SEQ CHAPTER \h \r 1 The nature of methoxyfenozide residues in
rotational crops is adequately understood, based on the available
confined rotational crop study  SEQ CHAPTER \h \r 1   SEQ CHAPTER \h \r
1 .  Following three soil applications of 14C-methoxyfenozide at rates
totaling 2.0 lb ai/A (1x rate)  SEQ CHAPTER \h \r 1 , total radioactive
residues accumulated at ≥0.01 ppm in mustard, radishes, and wheat
planted 31, 91, and 364 days after the last application. 
Methoxyfenozide was highly metabolized in rotational crops by oxidation,
demethylation, and hydroxylation to non-conjugated metabolites, which
were then conjugated with biomolecules yielding bound residues and
precursors in the sugar synthesis pathway.  

HED concluded that t  SEQ CHAPTER \h \r 1 he residues of concern in
rotational crops include methoxyfenozide, its free phenol metabolite
(RH-117,236), conjugated forms of the phenol metabolite (RH-151,055 and
RH-152,072), and the metabolites RH-152,067; RH-131,157; RH-152,071. 
For enforcement purposes, the tolerance definition for rotated crops
includes only parent in high-moisture crops and the combined residues of
parent and metabolites RH-151,055; RH-152,072; and RH-117,236 in
low-moisture crops.  Metabolites RH-152,067; RH-131,157; and RH-152,071
are also to be taken into account in risk assessments.

860.1900 Field Accumulation in Rotational Crops

DP# 322948, D. Rate, 02/JUN/2009

Label directions for methoxyfenozide currently specify the following
rotational crop restriction:  crops with registered uses may be
replanted at any time, and all other food or feed crops may be replanted
7 days after the last application.  Adequate limited and extensive
rotational crop field trials are available that support these rotational
crop restrictions, and the adequacy of the tolerances for rotational
crops were recently addressed in a separate petition.

As the maximum seasonal use rate being proposed for dry peas and popcorn
(1.0 lb ai/A) is the same as for other registered field and vegetable
crops, no changes are required in the current rotational crop
restrictions or tolerances.

 

860.1550 Proposed Tolerances

For purposes of the tolerances expression, HED previously determined
that the residue of concern is methoxyfenozide per se for primary crops
and livestock commodities, except meat byproducts and eggs.  The
residues of concern in eggs and meat byproducts include parent and
Metabolite RH-141,518.

Permanent tolerances are established for residues of methoxyfenozide per
se in/on a wide variety of plant commodities at levels ranging from 0.05
ppm in/on field corn grain and sweet corn ears to 160 ppm in/on soybean
aspirated grain fractions [40 CFR §180.544(a)(1)].  Permanent
tolerances are also established for residues of methoxyfenozide per se
in milk, meat and fat of livestock [40 CFR §180.544(a)(1)], and for the
combined residues of parent and its glucuronide conjugate (RH-141,518)
in eggs and meat byproducts at 0.02-0.40 ppm [40 CFR §180.544(a)(2)]. 
Tolerances have also been established for inadvertent or indirect
residues of methoxyfenozide per se in high-moisture rotational crops and
for the combined residues of methoxyfenozide, its phenol metabolite
(RH-117,236), and its glucoysl conjugates (RH-151,055 and RH-152,072) in
low-moisture rotational crops [40 CFR §180.544(d)(1 and 2)].  The
tolerances being proposed by IR-4 for the current petition are listed in
Table 8, along side ARIA’s recommended tolerances.

Although additional citrus fruit field trials are being requested as a
condition of registration, sufficient field trial data are available to
establish permanent tolerances on citrus fruits and dry peas.  The
citrus fruit tolerance will be reassessed once the requested field trial
data are available.  For both citrus fruit and dry peas the Agency’s
SOP “Guidelines for Setting Pesticide Tolerances Based on Field Trial
Data” were utilized for determining the appropriate tolerance level
for each commodity (Appendix II).  For citrus fruits, the residue values
from individual of citrus fruits were used to calculate MRL tolerances. 
The highest recommended MRL of 10 ppm from the orange data will be
recommended for citrus fruits (crop group 10).  For dry peas,  separate
tolerances were calculated using the data from the new trials adjusting
the residues from two trials (0.5x) to the 1x rate using proportionality
(0.30 ppm), using only the residue data from the four field trials
conducted at 1x (0.35 ppm), and using the previously reviewed data for
the back-eyed and southern pea trials (2.5 ppm).  The highest tolerance
recommendation of 2.5 ppm was chosen for the tolerance for pea, dry
seed.  Due to the >10x difference between the pea and bean tolerances, a
pea and bean, dried shelled, except soybean (subgroup 6C) tolerance
cannot be established.  Therefore, ARIA recommends that the current
bean, dry seed tolerance be retained at 0.24 ppm and a tolerance be
established at 2.5 ppm for pea, dry seed.   

The available residue data for field corn and avocados will be
translated to support the same respective uses on popcorn and
pomegranates.  The field corn residue data will support tolerances of
0.05 and 125 ppm in/on popcorn grain and stover, respectively.  No
tolerance is required for popcorn forage as it is not a regulated
livestock feedstuff.  The avocado residue data will support a tolerance
of 0.6 ppm in/on pomegranates. 

Based on the adequate orange processing study, separate tolerances are
not required for orange juice and dried pulp as residues were reduced in
juice (<0.2x) and concentrated only slightly in dried pulp (1.1x). 
However, a separate tolerance is required for citrus oil.  Based the 56x
processing factor for oil and HAFT residues of 1.67 ppm for citrus
fruits, the maximum expected residues in oil would be 93.5 ppm. 
Therefore, a tolerance of 100 ppm would be appropriate for citrus oil. 

As the proposed tolerances will not increase the dietary exposure of
livestock to methoxyfenozide residues, the proposed tolerances will not
affect the current livestock tolerances.  The proposed uses will also
not have an impact on the current rotational crop tolerances.  

Although there are currently Codex, Canadian or Mexican maximum residue
limits (MRLs) for residues of methoxyfenozide on primary crops and
livestock commodities, there are no MRLs for residues in the proposed
commodities.  Therefore, there are no international harmonization issues
associated with this petition.

Table 8. 	Tolerance Summary for Methoxyfenozide.

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

Tolerances listed under 40 CFR 180.544(a)(1)

Pea and bean, dried shelled, except soybean, subgroup 6C	0.35	2.5
Adequate pea data are available.  Commodity definition should be pea,
dry, seed.

Bean, dry, seed	0.24	0.24	No change for tolerance.

Pomegranate	0.6	0.6	Adequate residue data are available on avocados,
which will be translated to support the pomegranate tolerance. 

Corn, pop, grain	0.05	0.05	Adequate field corn data are available and
will be translated to support the same tolerances on pop corn.

Corn, pop, stover	125	125

	Corn, pop, forage	30	None	Forage is not a regulated commodity of
popcorn.

Tolerances listed under 40 CFR 180.544(c)

Fruit, citrus, group 10	2.0	10	Regional restriction for use in states
west of the Mississippi River.  Adequate citrus field trial data are
available; however, additional orange (2 tests), lemon (2 tests) and
grapefruit (1 test) data are required as a condition for registration.  

Citrus oil	70	100	An adequate processing study is available.  

References

DP #:	  SEQ CHAPTER \h \r 1 258034

Subject:	PP#8F5004 & PP#8F5006;  Methoxyfenozide.  Conclusions of the
13/JUL/1999 Meeting of the Metabolism Assessment Review Committee.  SEQ
CHAPTER \h \r 1 

From:  	W. Wassell  SEQ CHAPTER \h \r 1 

To:	  SEQ CHAPTER \h \r 1 G. Kramer

Dated:	23/JUL  SEQ CHAPTER \h \r 1 /1999

MRIDs:	  SEQ CHAPTER \h \r 1 None

DP #s:		251225, 251218, 249458, and 249438

Subject:	PP# 8F5004 & PP#8F5006:  Methoxyfenozide on Cotton and the Pome
Fruit Crop Group.  Evaluation of Metabolism Data, Residue Data, and
Analytical Methodology.   SEQ CHAPTER \h \r 1 

From:  	W. Wassell  SEQ CHAPTER \h \r 1 

To:	  SEQ CHAPTER \h \r 1 S. Lewis/J. Tavano

Dated:	27/JUL  SEQ CHAPTER \h \r 1 /1999

MRIDs:	44617816-44617822, 44617825, 44617826, 44617828-44617832,
44626303-44626306, 44626308-44626312, 44689101, and 44689102.  SEQ
CHAPTER \h \r 1 

DP #:	  SEQ CHAPTER \h \r 1 259989

Subject:	PP9F06033: Section 3 Request for Use of Methoxyfenozide on
Grapes and Fruiting Vegetables.  Review of Analytical Methods and
Residue Chemistry Data.

From:  	M. Doherty  SEQ CHAPTER \h \r 1 

To:	  SEQ CHAPTER \h \r 1 A. Layne/J. Tavano

Dated:	0  SEQ CHAPTER \h \r 1 8/AUG/2000

MRIDs:	44873405 through 44873411  SEQ CHAPTER \h \r 1 

DP #s:	  SEQ CHAPTER \h \r 1 269986, 274542

Subject:	  SEQ CHAPTER \h \r 1 Methoxyfenozide in/on Various Rotational
Crops.  Residue Chemistry Review.

From:  	  SEQ CHAPTER \h \r 1 M. Nelson

To:	  SEQ CHAPTER \h \r 1 M. Laws/J. Tavano

Dated:	  SEQ CHAPTER \h \r 1 07/AUG/2002

MRIDs:	  SEQ CHAPTER \h \r 1 45194701, 45194702, 45194703, 45194704

DP #s:	  SEQ CHAPTER \h \r 1 269969

Subject:	  SEQ CHAPTER \h \r 1 PP#0F06213:  Methoxyfenozide in/on Field
Corn and Sweet Corn; Poultry Tolerances; and, Higher Tolerances on Other
Selected Animal Commodities. Residue Chemistry Review.

From:  	  SEQ CHAPTER \h \r 1 M. Nelson

To:	  SEQ CHAPTER \h \r 1 M. Laws/J. Tavano

Dated:	07  SEQ CHAPTER \h \r 1 /AUG/2002

MRIDs:	  SEQ CHAPTER \h \r 1 45213500, 45213502 thru 45213514

DP #s:	  SEQ CHAPTER \h \r 1 259549

Subject:	  SEQ CHAPTER \h \r 1 METHOXYFENOZIDE Supplemental Human Health
Risk Assessment for: PP#9F06033 - Fruiting Vegetables (except Cucurbits)
Crop Group; Grapes; Raisins;  PP#9F06062 - Leafy and Cole (Brassica)
Vegetables Crop Groups; PP#0F06201 -  Rotational Crops; PP#0F06213 -
Field and Sweet Corn; Higher Milk/Fat /Mbyp; Add Poultry/Eggs;
PP#1F06259 - Stone Fruits Crop Group; Prune; PP#1F06287 - Tree Nuts Crop
Group, including Pistachio; Almond Hulls; PP#2E06382 - Globe Artichoke;
and PP#2E06408 - Lychee, including Longan, Spanish Lime, Pulasan, and
Rambutan.

From:  	  SEQ CHAPTER \h \r 1 M. Nelson

To:	  SEQ CHAPTER \h \r 1 M. Laws/J. Tavano/S Brothers/R. Forrest

Dated:	  SEQ CHAPTER \h \r 1 07/AUG/2002

MRIDs:	None  SEQ CHAPTER \h \r 1 

DP #s:	  SEQ CHAPTER \h \r 1 331948

Subject:	  SEQ CHAPTER \h \r 1  Methoxyfenozide.  Use on Sweet Potato,
Blueberry, Dry Bean, Grass, Peanut, Green Onion, Avocado, Guava, Alfalfa
and Clover.  Summary of Analytical Chemistry and Residue Data.  Petition
Numbers 6E7086, 7E7218, & 6F7135.

From:  	  SEQ CHAPTER \h \r 1 W. Cutchin

To:	  SEQ CHAPTER \h \r 1 W. Cutchin 

Dated:	  SEQ CHAPTER \h \r 1 18/DEC/2007

MRIDs:	46870901-5, 47135701-03

DP #s:	  SEQ CHAPTER \h \r 1 322948, 295721, 288924, 295680

Subject:	  SEQ CHAPTER \h \r 1  Methoxyfenozide.  Registrant’s
Response to Conditional Registrations for Uses and/or Tolerances on Leaf
Vegetables, Rotational Crops, Stone Fruits, and Poultry Commodities. 
Summary of Analytical Chemistry and Residue Data.  Petition Numbers:
9F06062, 0F06201, 0F06213, 1F06259.

From:  	  SEQ CHAPTER \h \r 1 D. Rate

To:	  SEQ CHAPTER \h \r 1 D. Rate

Dated:	  SEQ CHAPTER \h \r 1 02/JUN/2009

MRIDs:	46606301, 45870501, 45870502, 46039301

  SEQ CHAPTER \h \r 1 Attachments:  

Appendix I - International Residue Limit Status sheet

Appendix II - Tolerance Assessment Calculations

Template Version April 2008

Appendix I.	International Residue Limit Status Sheet

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name:  3-methoxy-2-methylbenzoic acid
2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazide	Common Name: 
Methoxyfenozide	X Proposed tolerances

⁯ Reevaluated tolerance

⁯ Other	Date:  02/26/09

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:  PP# 8E7447

DP #s: 358341

⁯ No Limits

√ No Limits for the crops requested	⁯ No Limits

√  No Limits for the crops requested

Residue definition:  Methoxyfenozide 	Residue definition: 
Methoxyfenozide 

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

	Notes/Special Instructions: S.Funk, 03/01/2009.

Appendix II.  Tolerance Assessment Calculations.

For each of the crops listed below, the Guidance for Setting Pesticide
Tolerances Based on Field Trial Data (SOP), along with the tolerance
spreadsheet, was used for calculating recommended tolerances.  As
specified in the SOP, the minimum of the 95% upper confidence limit
(UCL) on the 95th percentile and the point estimate of the 99th
percentile was selected as the tolerance value in cases when the dataset
was large (greater than 15 samples) and reasonably lognormal.  For
datasets that were small (≤15 samples) and reasonably lognormal, the
upper bound estimate of the 95th percentile based on the median residue
value was compared to the minimum of the 95% UCL on the 95th percentile
and the point estimate of the 99th percentile, and the minimum value was
selected as the tolerance value.  For datasets that were not lognormal,
the upper bound on the 89th percentile was selected as the tolerance
value (distribution-free method).  The rounding procedures specified in
the SOP were also used.

Citrus Fruits, Crop Group 10

The dataset used to assess a tolerance for methoxyfenozide residues on
citrus fruit consisted of field trial data for oranges, lemons, and
grapefruits, and represented application rates of 1.00-1.02 lb ai/A (4
applications at ~0.25 lb ai/A/application) with a 1-day PHI.  As
specified by the SOP, the field trial application rates and PHIs are
within 25% of the maximum label application rate and minimum label PHI,
respectively.  The residue values used to calculate the tolerance are
provided in Tables II-1, II-2, and II-3.  

All field trial sample results for orange, lemon, and grapefruit were
above the LOQ (0.021 ppm).  The individual datasets for orange, lemon,
and grapefruit were entered into the tolerance spreadsheet.  Visual
inspection of the lognormal probability plots for orange, lemon, and
grapefruit (Figures II-1, II-3, and II-5) indicate that the datasets are
reasonably lognormal.  The results from the approximate Shapiro-Francia
test statistic (Figure II-2, II-4, and II-6) confirmed that the
assumption of lognormality should not be rejected.  

Using the tolerance spreadsheet, the recommended tolerance is 10 ppm for
orange, 1.5 ppm for lemon, and 0.5 ppm for grapefruit.  Based on these
individual tolerances, a tolerance of 10 ppm for citrus fruit, crop
group 10 is recommended.

Table II-1.	Methoxyfenozide Residues in/on Oranges following Four Foliar
Applications of Methoxyfenozide (FlC) at Rates Totaling ~1.0 lb
ai/A/season.

Regulator:	EPA

Chemical:	Methoxyfenozide

Crop:	Orange

PHI:	1 day

App. Rate:	0.995-1.021 lb ai/A

Submitter:	IR-4

MRID Citation:	MRID 47556401

	Residues

	1.620

	1.720

	0.140

	0.168

Figure II-1.	Lognormal Probability Plot of Methoxyfenozide Residues
in/on Oranges Following Four Foliar Applications Totaling ~1.0 lb ai/A.

 

Figure II-2.	Data Summary Sheet for Residues of Methoxyfenozide in/on
Oranges Following Four Foliar Applications.

 

Table II-2.	Methoxyfenozide Residues in/on Lemons following Four Foliar
Applications of Methoxyfenozide (FlC) at Rates Totaling ~1.0 lb
ai/A/season.

Regulator:	EPA

Chemical:	Methoxyfenozide

Crop:	Lemon

PHI:	1 day

App. Rate:	0.995-1.021 lb ai/A

Submitter:	IR-4

MRID Citation:	MRID 47556401

	Residues

	0.374

	0.407

	0.933

	0.650

Figure II-3.	Lognormal Probability Plot of Methoxyfenozide Residues
in/on Lemons Following Four Foliar Applications Totaling ~1.0 lb ai/A.

 

Figure II-4.	Data Summary Sheet for Residues of Methoxyfenozide in/on
Lemons Following Four Foliar Applications.

 

Table II-3.	Methoxyfenozide Residues in/on Grapefruit following Four
Foliar Applications of Methoxyfenozide (FlC) at Rates Totaling ~1.0 lb
ai/A/season.

Regulator:	EPA

Chemical:	Methoxyfenozide

Crop:	Grapefruit

PHI:	1 day

App. Rate:	0.995-1.021 lb ai/A

Submitter:	IR-4

MRID Citation:	MRID 47556401

	Residues

	0.278

	0.229

	0.117

	0.112

Figure II-5.	Lognormal Probability Plot of Methoxyfenozide Residues
in/on Grapefruit Following Four Foliar Applications Totaling ~1.0 lb
ai/A.

 

Figure II-6.	Data Summary Sheet for Residues of Methoxyfenozide in/on
Grapefruit Following Four Foliar Applications.

 

Pea, dry, seed

Two datasets were used to assess a tolerance for methoxyfenozide
residues on pea, dry, seed. Set 1 consisted of field trial data for the
representative crop of dry pea, and represented application rates of
0.973-0.999 lb ai/A (4 applications at ~0.25 lb ai/A/application) with
PHIs of 6-7 days.  Set 2 residue data were taken from the previously
reviewed data on southern and black-eyed pea trials treated with a
seasonal application rate of 1.0 lb ai/A and a 7-8 day PHI.  As
specified by the SOP, the field trial application rates and PHIs are
within 25% of the maximum label application rate and minimum label PHI,
respectively.  The dry pea residue values used to calculate the
tolerance are provided in Table II-4 and Table II-5.  

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indicates that the dataset is reasonably lognormal.  The results from
the approximate Shapiro-Francia test statistic (Figure II-8) confirmed
that the assumption of lognormality should not be rejected.  Using the
tolerance spreadsheet, the recommended tolerance for dry peas using set
1 data is 0.35 ppm.

For set 2, all field trial sample results for dry pea (black-eyed and
southern) were above the LOQ (0.05 ppm).  This dataset consisted of 12
samples.  The dry pea (black-eyed and southern) dataset was entered into
the tolerance spreadsheet.  Visual inspection of the lognormal
probability plot for the residues (Figure II-9) indicates that
lognormality should be rejected.  The results from the approximate
Shapiro-Francia test statistic (Figure II-10) confirmed that the
assumption of lognormality should be rejected.  Using the tolerance
spreadsheet the recommended tolerance for dry peas (black-eyed and
southern) using dataset 2 is 2.5 ppm.

The data from the dry beans field trials (DP# 331948, W. Cutchin,
12/18/07) were all <0.05 ppm with the exception of two with samples with
residues at 0.076 and 0.22 ppm.  For this data, the use of the MRL
spreadsheet is not appropriate and the tolerance was set at 0.24 ppm. 
The higher pea tolerance of 2.5 ppm is recommended. This tolerance is
>10x the tolerance for dry beans; therefore, a pea and bean, dried
shelled, except soybean (subgroup 6C) is not appropriate.  

Table II-4.	Methoxyfenozide Residues in/on Dry Pea following Four Foliar
Applications of Methoxyfenozide (FlC) at Rates Totaling ~1.0 lb
ai/A/season.

Regulator:	EPA

Chemical:	Methoxyfenozide

Crop:	Dry Pea

PHI:	6-7 days

App. Rate:	0.973-0.999 lb ai/A

Submitter:	IR-4

MRID Citation:	MRID 47556402

	Residues

	0.062

	0.073

	0.084

	0.105

	0.162

	0.166

	0.168

	0.171



Figure II-7.	Lognormal Probability Plot of Methoxyfenozide Residues
in/on Dry Pea Following Four Foliar Applications Totaling ~1.0 lb ai/A.

Figure II-8.	Data Summary Sheet for Residues of Methoxyfenozide in/on
Dry Pea Following Four Foliar Applications.

Table II-5.  Methoxyfenozide Residues in/on Dry Pea (Black-eyed and
Southern) following Four Foliar Applications of Methoxyfenozide at Rates
Totaling ~1.0 lb ai/A/season

Regulator:	EPA

Chemical:	Methoxyfenozide

Crop:	Dry Pea

PHI:	6-7 days

App. Rate:	1.0 lb ai/A

Submitter:	IR-4

MRID Citation:	MRID 45795101

	Residues

	0.098

	0.160

	0.531

	0.673

	0.503

	0.555

	0.137

	0.170

	0.102

	0.127

	2.000

	3.390

Figure II-9.	Lognormal Probability Plot of Methoxyfenozide Residues
in/on Dry Pea (Black-eyed and Southern) Following Four Foliar
Applications Totaling ~1.0 lb ai/A.

 

Figure II-10.	Data Summary Sheet for Residues of Methoxyfenozide in/on
Dry Pea (Black-eyed and Southern) Following Four Foliar Applications.

 

Methoxyfenozide	Summary of Analytical Chemistry and Residue Data	DP#: 
358341

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