Document ID: EPA-HQ-OPP-2007-0300-0010
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2008-01-09T05:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

	OFFICE OF PREVENTION, 

	PESTICIDES AND TOXIC

SUBSTANCES

MEMORANDUM

	Date:  	Nov 5, 2007

	Subject:	Zeta-Cypermethrin.  Petitions for Use on Citrus (Crop Group
10), Oilseeds (Prooposed Crop Group 20), Safflower, Wild Rice and Okra. 
Summary of Analytical Chemistry and Residue Data.  Petition Numbers
6F7132, 6E7133, and 7E7255

	

DP Numbers:	335223, 335226, 343052	Decision Nos.:	371717, 371868, 382487

PC Code:	129064	MRID(s):	46969201, 46971402

40 CFR	180.418 (a)(2)	Chemical Class:	Pyrethroid Insecticide 

	From:	Dennis McNeilly, Chemist

		Registration Action Branch 2

		Health Effects Division (7509P)

	Through:	Michael Doherty, Ph.D., Senior Chemist

		Registration Action Branch 2

		Health Effects Division (7509P)

			and

		David Soderberg, Chemist

		Registration Action Branch 2

		Health Effects Division (7509P)

	To:	Daniel Rosenblatt, Chief

		Insecticide Branch

		Division (7505P)

This document was originally prepared under contract by Dynamac
Corporation (1910 Sedwick Road, Building 100, Durham NC 27713; submitted
6/20/2007), except for the sections concerning the proposed Oilseed Crop
Group 20 uses.  The document has been reviewed by the Health Effects
Division (HED) and revised to reflect current Office of Pesticide
Programs (OPP) policies.

Executive Summary

Zeta-cypermethrin [(S-cyano(3-phenoxyphenyl)methyl (±))-cis-trans
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate] is a broad
spectrum, synthetic pyrethroid insecticide containing the same eight
stereoisomers that are present in cypermethrin.  However,
zeta-cypermethrin is enriched in the four insecticidally active S
isomers and contains ≤1% each of the inactive R isomers.  Tolerances
for residues of zeta-cypermethrin, including its inactive R isomers,
have been established in/on plant and animal commodities at levels
ranging from 0.05-40 ppm [40 CFR 180.418(a)(2)].

Zeta-cypermethrin is currently registered to FMC Corporation for use on
a wide variety of food/feed crops, primarily as repeated broadcast
foliar applications.  In the current petitions, the Interregional
Project Number 4 (IR-4) is proposing new uses on citrus fruits,
safflower, okra and wild rice for two formulations of zeta-cypermethrin.
 These formulations are a 1.5 lb ai/gal emulsifiable concentrate (EC;
Fury® and Mustang® 1.5 EC Insecticides, EPA Reg. No. 279-3125), and a
1.5 lb ai/gal water in oil emulsion (EW; Mustang® 1.5 EW Insecticide,
EPA Reg. No. 279-3126).  IR-4 is proposing that the existing uses on
fruiting vegetables and rice be expanded to include, respectively, okra
and wild rice.  These uses allow for repeated broadcast foliar
applications of zeta-cypermethrin at up to 0.05 lb ai/A/application at
retreatment intervals (RTIs) of no less than 7 days, for totals of 0.2
lb ai/A/season on rice and 0.3 lb ai/A/season on fruiting vegetables. 
The proposed use on citrus fruits is for repeated foliar applications at
up to 0.05 lb ai/A, and minimum RTIs of 14 days, for a total of 0.2 lb
ai/A/season.  The proposed use on safflower is for repeated broadcast
foliar applications at up to 0.05 lb ai/A at minimum RTIs of 14 days,
for a total of 0.15 lb ai/A/season.  In conjunction with these uses,
IR-4 is proposing the following permanent tolerance for
zeta-cypermethrin:

Fruit, citrus, group 10	0.25

Citrus, dried pulp	0.5

Citrus, oil	0.9

Safflower	0.2

Okra	0.2

Rice, wild, grain	1.5

In addition, IR-4 has submitted a petition (7E7255) to establish a
tolerance for the proposed Oilseed Crop Group 20.  No residue date were
submitted with this petition, instead IR-4 has cited data for rapeseed,
sunflower, and safflower (which have the same or similar use pattern). 
This Oilseed Crop Group is not yet established and therefore individual
tolerances are being recommended for every commodity in the proposed
Oilseed Crop Group 20. The proposed use on the oilseed crops is for
repeated broadcast foliar applications at up to 0.05 lb ai/A at minimum
RTIs of 7 days, for a total of 0.25 lb ai/A/season.

Borage, seed	0.2

Castor oil plant, seed	0.2

Chinese tallowtree, seed	0.2

Crambe, seed	0.2

Cuphea, seed	0.2

Echium, seed	0.2

Euphorbia, seed	0.2

Evening primrose, seed	0.2

Flax, seed	0.2

Gold of pleasure, seed	0.2

Hare’s ear mustard, seed	0.2

Jojoba, seed	0.2

Lesquerella, seed	0.2

Lunara, seed	0.2

Meadowfoam, seed	0.2

Milkweed, seed	0.2

Mustard, seed	0.2

Niger seed, seed	0.2

Oil radish, seed	0.2

Poppy, seed	0.2

Rose hip, seed	0.2

Sesame, seed	0.2

Stokes aster, seed	0.2

Sweet rocket, seed	0.2

Tallowwood, seed	0.2

Tea oil plant, seed	0.2

Vernonia, seed	0.2

The nature of zeta-cypermethrin in plants and animals is adequately
understood.  The parent compound is the only residue of concern for
tolerance and dietary risk assessment.

Adequate tolerance enforcement methods are available in PAM Volume II
for determining residues of cypermethrin and zeta-cypermethrin in/on
plant (Method I) and livestock (Method II) commodities.  Both methods
are GC methods with electron capture detection (ECD) and have undergone
successful Agency method validations.  Method I has a detection limit of
0.01 ppm, and Method II has detection limits of 0.005 ppm for milk and
0.01 ppm for livestock tissues.  These methods are not stereospecific;
thus no distinction is made between residues of cypermethrin (all eight
stereoisomers) and zeta-cypermethrin (enriched in S-isomers).  

Adequate GC/ECD methods are also available for collecting data on
zeta-cypermethrin residues in commodities from the submitted safflower
and citrus field trials and processing studies.  These methods are more
recent derivations of the tolerance enforcement method.  For these
methods, residues in safflower seeds and meal, and citrus fruits, dried
pulp and juice are extracted with acetone:water (70:30 or 85/15, v:v)
and purified by solvent partitioning and silica gel solid phase
extraction (SPE) cleanup.  Residues in safflower and citrus oil are
dissolved in hexane and purified by solvent partitioning and SPE
cleanup.  Residues are then determined by GC/ECD using external
standards.  The limits of quantitation (LOQ) are approximately 0.05 ppm
for each commodity, and the limit of detection (LOD) is 0.01 ppm.

The citrus field trials are supported by existing storage stability
data.  Zeta-cypermethrin is stable in frozen tomatoes and tomato
processed commodities for up to 26-27 months, it has also been shown to
be stable in citrus commodities for up to a year.  The safflower field
trials and processing studies are supported by new data indicating that
zeta-cypermethrin is stable in frozen safflower seeds for up to 15.8
months and in frozen safflower meal and oil for up to 12-13 months.

In the 23 citrus fruit field trials (12 orange, 5 lemon, 6 grapefruit)
conducted during 2004/2005, zeta-cypermethrin (1.5 lb/gal EC or EW) was
applied to citrus trees as four foliar applications using 0.05 lbs
ai/A/application and RTIs of 12-15 days, for a total application of 0.2
lb ai/A/season (1x rate).  The EC formulation was used in 12 tests (6
orange, 3 lemon, 3 grapefruit), and the EW formulation was used in 11
tests (6 orange, 2 lemon, 3 grapefruit).  Applications were made using
ground equipment as either dilute sprays (158-264 gal/A) in 11 trials or
as concentrated sprays (52-97 gal/A) in 12 trials.  None of the
applications include the use of any spray adjuvants.  At 1 day after the
last application (DALA), zeta-cypermethrin residues were highest in/on
grapefruits (0.05-0.20 ppm), followed by oranges (<0.05-0.16 ppm), and
lemons (0.05-0.09 ppm).  Overall average residues were 0.119 ppm in/on
grapefruit, 0.103 ppm in/on oranges, and 0.07 ppm in/on lemons.  The
highest average field trial (HAFT) residues were 0.20 ppm for
grapefruit, 0.16 ppm for oranges, and 0.08 ppm for lemons.  There were
no substantial differences in residue levels between the two
formulations or between the dilute and concentrated application volumes.

In the 5 safflower field trials conducted during 2003, zeta-cypermethrin
(1.5 lb/gal EC or EW) was applied to safflower as three broadcast foliar
applications during bloom and seed development at rates of 0.047-0.052
lb ai/A/application and RTIs of 10-18 days, for a total of 0.144-0.153
lb ai/A/season (1x rate).  All applications were made using ground
equipment in spray volumes of 13-22 gal/A, and did not include the use
of any spray adjuvants.  Residues of zeta-cypermethrin were <0.05-0.15
ppm in/on 14 samples of safflower seed harvested at 13-14 DALA.  The
average residue was 0.065 ppm and the HAFT residue was 0.145 ppm.  The
side-by-side tests with the EC and EW formulations indicated that there
was no significant difference in residues levels between the two
formulations.

No field trial data were submitted on okra or wild rice; however, the
purposed uses are identical to the current uses on fruiting vegetables
and rice.  Therefore, the existing field trial data on fruiting
vegetables and rice will respectively support the proposed uses on okra
and wild rice.

No field trial date were submitted for any of the Oilseed commodities;
however, the purposed uses are identical to the current uses on
sunflower.  The proposed use is similar to the use on canola, although
canola allows for one more application per season (six applications) and
a higher maximum seasonal rate of 0.3 lb ai/A.  Oilseeds include those
crops from which oil is extracted from their seed and used to produce
edible or inedible oils as well as a high-protein livestock meal.  Oils
may be extracted from plants by applying pressure to the seed, or by
dissolving parts of the plants in water or another solvent, and
distilling the oil, or by infusing parts of the plant in base oil.  The
oilseeds are primarily soybeans, sunflower seed, canola, rapeseed,
safflower, flax seed, or castor bean, mustard seed, peanut and
cottonseed, used for the production of cooking oils, protein meals for
livestock and industrial uses.

Adequate processing studies were submitted for both citrus fruits and
safflower.  In the orange processing study, residues in/on whole oranges
(0.03 ppm) treated at a 1x rate did not concentrate in juice (<0.3x),
but concentrated by 9x in dried pulp and 19x in oil.  Based on the HAFT
residues from the citrus field trials (0.2 ppm) and the above processing
factors, the maximum expected residues in citrus dried pulp and oil
would be 1.8 and 3.8 ppm, respectively.  In the safflower processing
study, residues were 0.05 ppm in/on safflower seeds following
applications at a 1x rate.  Residue did not concentrate (<1x) in either
safflower meal or oil; therefore, separate tolerances are not required
for these safflower commodities. 

The potential maximum dietary burden (MDB) of livestock to
zeta-cypermethrin residues was recalculated based on the existing and
recommended tolerances for livestock feedstuffs and using recent
revisions to guidance on constructing livestock diets.  The MDB was
calculated to be 19.8 ppm for beef cattle, 22.0 ppm for dairy cattle,
and 0.7 ppm for poultry and swine.  Based on these levels of dietary
exposure and the data from the adequate ruminant and poultry feeding
studies, no changes in the existing tolerances on livestock commodities
are required for the current petitions.

Adequate confined and limited field rotational crop studies are
available for cypermethrin, and these studies are also adequate for
zeta-cypermethrin.  The studies indicate that residues of cypermethrin
and its metabolites were nondetectable (<0.01 ppm) in/on representative
rotational crops planted 30 days after a soil application of
cypermethrin at 0.5 lb ai/A.  These data support the current label
restriction of a 30-day plant-back interval for crops not listed on the
label, and indicate that tolerances are not required for inadvertent
residues in rotational crops.

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

No deficiencies were noted in the subject petition that would preclude
establishing permanent tolerances for zeta-cypermethrin residues in/on
the requested crops/crop groups.  HED recommends establishing permanent
tolerances for residues of zeta-cypermethrin, and its inactive
R-isomers, at 0.35 ppm in/on citrus fruit (Crop Group 10), at 1.8 ppm in
dried citrus pulp, at 4.0 ppm in citrus oil, at 0.2 ppm in/on safflower
seeds, at 0.2 ppm in other oilseed commodities (see Table 9 for the
specific tolerances required) at 0.4 ppm for oilseed, refine oils; at
0.2 ppm in/on okra, and at 1.5 ppm in/on wild rice grain.

Background

≤1% each of the inactive R isomers.  Zeta-cypermethrin is currently
registered to FMC Corporation for use as broadcast foliar applications
on a wide variety of food/feed crops as a 1.5 lb/gal EC and a 1.5 lb/gal
EW.  Permanent tolerances for residues of zeta-cypermethrin and its
inactive R-isomers have been established on plant commodities at levels
ranging from 0.05 to 40 ppm [40 CFR§180.418(a)(2)], and tolerances have
been established on animal commodities at levels ranging from 0.05 ppm
(meat byproducts and poultry) to 2.5 ppm in milk fat. 

IR-4 has submitted tolerance petitions (PP# 6E7132, 6E7133, and 7E7255)
proposing new uses for zeta-cypermethrin, formulated as an EC or EW, on
citrus fruits, oilseed commodities (proposed Crop Group 20), okra,
safflower, and wild rice.  The nomenclature and physicochemical
properties of zeta-cypermethrin are presented in Tables 1 and 2.

-α-cyano-3-phenoxybenzyl
(1R)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

or

(S)-α-cyano-3-phenoxybenzyl (1RS, 3RS, 1SR,
3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

CAS name	(S)-cyano(3-phenoxyphenyl)methyl
(±)-cis-trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxyla
te

CAS registry number	52315-07-8

End-use product (EP)	1.5 lb/gal EC (Fury® or Mustang® 1.5 EC
Insecticide; EPA Reg. No. 279-3125) 

1.5 lb/gal EW (Mustang® 1.5 EW Insecticide; EPA Reg. No. 279-3126)

Table 2.  Physicochemical Properties of the Technical Grade Test
Compound:  Zeta-Cypermethrin.

Parameter	Value	Reference

Melting point	-22.4°C	MRID 46971402 1

pH	4.5 (1% suspension)

	Density	1.219 g/mL at 25°C

	Water solubility (25°C)	45 ppb

	Solvent solubility	miscible in acetone, acetonitrile, methylene
chloride, and toluene

	Vapor pressure	1.9 x 10-9 mm Hg at 25°C

	Dissociation constant, pKa	Not available

	Octanol/water partition coefficient, Log(KOW)	>6

	UV/visible absorption spectrum	Not available

	1	Values as reported by the petitioner.

860.1200 Directions for Use

IR-4 is proposing the use of two zeta-cypermethrin end-use products
(EPs), a 1.5 lb/gal EC (Fury® or Mustang® 1.5 EC Insecticide; EPA Reg.
No. 279-3125) and a 1.5 lb/gal EW (Mustang® 1.5 EW Insecticide; EPA
Reg. No. 279-3126) for use on citrus, okra, oilseeds, safflower, and
wild rice.  The petitioner provided draft labels containing the proposed
use directions (Table 3).

Table 3.  Summary of Directions for Use of Zeta-Cypermethrin.

Applic. Timing, Type, and Equip.	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 1

Citrus Fruits

Broadcast foliar applications during fruit development using ground or
aerial equipment	1.5 lb/gal EC

[279-3125]

1.5 lb/gal EW

[279-3126]	0.05	4	0.2	1	Apply in a minimum of 10 gal/A by air.  For
ground applications apply in a minimum of 20 gal/A for concentrate
sprays and a minimum of 100 gal/A for a dilute sprays.  

A minimum RTI of 14 days is specified.

Fruiting Vegetables (Including Okra)

Broadcast foliar applications based on insect populations, using ground
or aerial equipment.	1.5 lb/gal EC

[279-3125]

1.5 lb/gal EW

[279-3126]	0.05	6	0.3	1	Apply in a minimum of 10 gal/A by ground and 2
gal/A by air.  A minimum RTI of 7 days is specified.

Rice and Wild Rice

Broadcast foliar applications based on insect populations, using ground
or air equipment	1.5 lb/gal EC

[279-3125]

1.5 lb/gal EW

[279-3126]	0.05	4	0.4	14	Apply in a minimum of 5 gal/A by air.   Do not
apply as an ultra-low volume application.

A minimum RTI of 7 days is specified.

Do not release flood water within 7 days of application, and do not use
treated rice fields for aquaculture of edible fish or crustacean.

Safflower

Broadcast foliar applications as determined by scouting practices, using
ground or air equipment	1.5 lb/gal EC

[279-3125]

1.5 lb/gal EW

[279-3126]	0.05	3	0.15	14	A minimum application volume of 15 gal/A is
specified along with a minimum RTI of 14 days.

                                                                Oilseed
Commodities (proposed Crop Group 20)

Borage, seed; Castor oil plant, seed; Chinease tallowtree, seed; Crambe,
seed; Cuphea, seed; Echium, seed; Euphorbia, seed; ZEvening primrose,
seed; Flax, seed; Gold of pleasure, seed; Hare’s ear mustard, seed;
Jojoba, seed; Lesquerella, seed; Lunara, seed; Meadowfoam, seed;
Milkweed, seed; Mustard, seed; Niger seed, seed; Oil radish, seed;
Poppy, seed; Rose hip, seed; Sesame, seed; Stokes aster, seed; Sweet
rocket, seed; Tallowwood, seed; Tea oil plant, seed; Vernonia, seed.  

Broadcast foliar applications as determined by scouting practices, using
ground or air equipment	1.5 lb/gal EC

[279-3125]

1.5 lb/gal EW

[279-3126]	0.05	5	0.25	30	Apply in a minimum of 2 gal/A when using
aerial equipment or 10 gallons per acre when using ground equipment.

A minimum RTI of 7 days is specified.

1 Both labels specify a rotational crop restriction of 30 days for
replanting of any crops not listed on the label.

Conclusions:  The proposed use directions are adequate and are supported
by the available field trial data.

 

  SEQ CHAPTER \h \r 1 860.1300 Nature of the Residue – Plants and
Animals

HED MARC Determination of Residues of Concern (D269584, Y. Donovan,
11/3/2000)

The nature of the residue in plants and animals is adequately
understood.  The HED Metabolism Assessment Review Committee concluded
that, for the case of cypermethrin and zeta-cypermethrin, the parent
compound is the only residue of concern which needs to be included in
the tolerance expression and used for dietary risk assessment, including
drinking water.  The Committee also concluded that the metabolite DCVA
[1-(RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxyl
ic acid] need not be included in the risk assessment and, therefore, can
be waived in future residue analyses of samples from cypermethrin and
zeta-cypermethrin studies.  This decision regarding DCVA does not extend
to other pyrethroids which generate this metabolite.  Each such
insecticide needs to be examined individually with respect to DCVA.

860.1340 Residue Analytical Methods

Enforcement methods

Adequate enforcement methods are available in PAM Volume II for
determining residues of both cypermethrin and zeta-cypermethrin in plant
(Method I) and livestock (Method II) commodities.  These GC/ECD methods
have undergone successful Agency method tryouts.  These methods are not
stereospecific; thus no distinction is made between residues of
cypermethrin (all eight stereoisomers) and zeta-cypermethrin (an
enriched isomer form of cypermethrin).

  

For Method I, residues of cypermethrin are extracted from crop samples
with acetone:hexane (1:1, v:v) and from water by partitioning with
hexane.  Some oily crop extracts require partitioning with acetonitrile
to remove co-extracted lipids.  Residues in crop samples are also
cleaned up by gel permeation chromatography.  Residues are then
determined by GC/ECD.  The LOQ is 0.05 ppm and the LOD is 0.01 ppm for
residues in plant samples.

For Method II, residues of cypermethrin are extracted from milk and
tissue samples with acetone:hexane (1:1, v:v) in the presence of
potassium oxalate (milk) or anhydrous sodium sulfate (tissues) after
addition of a standard.  Co-extracted lipids are removed by partition
column chromatography on Florisil.  Tissue sample extracts undergo
additional cleanup by adsorption column chromatography on Florisil. 
Residues are then determined by GC/ECD.  The LOD is 0.005 ppm for milk
and the LOD and LOQ are 0.01 ppm and 0.05 ppm, respectively, for
livestock tissues.

Data-collection methods

The data-collection methods use for determining zeta-cypermethrin
residues in the current citrus and safflower field trials and processing
studies are GC/ECD methods which are recent adaptations of Method I in
PAM Volume II.

For each method,   SEQ CHAPTER \h \r 1 residues are extracted from
safflower seeds and meal and citrus fruit, pulp and juice with
acetone:water (85/15 or 70/30, v/v).  Samples are then centrifuged, NaCl
is added, and residues are partitioned into hexane.  Residues are then
concentrated and cleaned-up by eluting a silica gel SPE cartridge with
hexane:ethyl acetate.  For analysis of safflower and citrus oils,
samples are dissolved in hexane and partitioned against 0.1M NaOH in 10%
aqueous NaCl, discarding the aqueous fraction.  Residues are then
partitioned into acetonitrile, concentrated, redissolved in hexane, and
cleaned-up by using a silica gel SPE cartridge eluted with either 2.5%
tert-butyl ether or 5% ethyl acetate in hexane.  The purified residues
from all matrices are analyzed by GC/ECD, using external standards.  The
validated LOQ for zeta-cypermethrin in all matrices is 0.05 ppm and the
LOD is 0.01 ppm.  Each of the data collection methods were adequately
validated in conjunction with the analysis of samples from field and
processing studies. 

Conclusions.  Adequate GC/ECD methods are available for both tolerance
enforcement and data collection.

860.1360 Multiresidue Methods

The 1/94 FDA PESTDATA database (PAM Volume I) indicates that residues of
cypermethrin are completely recovered (>80%) using multiresidue method
Sections 302 (Luke), 303 (Mills, Onley, and Gaither) and 304 (Mills
fatty food).

860.1380 Storage Stability

The storage intervals and conditions for samples from the field trial
and processing studies submitted with these petitions are presented
below in Table 4.

Table 4.  Sample Storage Conditions and Intervals.

MRID Number	Crop Matrices	Storage Conditions (°C)	Maximum Storage
Interval (Months)

46971402	Citrus fruits	-18	8

	Orange Oil

<1

	Orange, Dried Pulp

<1

	Orange Juice

<1

4696201	Safflower Seed	-26 to -13	15.8

	Safflower meal

10.0

	Safflower oil

12.6

Adequate storage stability data are available to support the storage
conditions and intervals of samples collected from field and processing
studies.  Previously reviewed data from numerous petitions indicate that
zeta-cypermethrin is reasonably stable under frozen storage conditions
in/on tomato and its processed commodities (paste and puree) for 26-27
months.  These data will support the sample storage intervals for whole
citrus fruits and fresh pulp.  No supporting storage stability data are
required on orange processed fractions as the frozen processed samples
were analyzed within 1 month of collection.  

Storage stability data were provided on zeta-cypermethrin in safflower,
safflower meal, and safflower oil.  Control samples of these commodities
were fortified with zeta-cypermethrin at approximately 0.3 ppm and
analyzed after various intervals of frozen storage, together with
freshly fortified samples.  The data indicate that zeta-cypermethrin is
stable in frozen storage for at least 15.8 months in safflower seeds and
12-13 months in safflower meal and oil.

Conclusions:  The available storage stability data are adequate and
support the sample storage intervals and conditions used in the citrus
and safflower field trials and processing studies.

860.1400 Water, Fish, and Irrigated Crops

As wild rice is an aquatic crop, the proposed use could have an impact
on the exposure of fish and irrigated crops to zeta-cypermethrin
residues.  However, aquatic issues pertaining to uses on rice were
previously addressed in conjunction the earlier petition on rice
(PP#9F6040).  Concerns for inadvertent exposure of fish and crops were
mitigated by modifications to the use directions.  The current use
directions for rice specify that flood waters are not to be released
within 7 days of application, and prohibit the use of treated rice
fields for aquaculture of edible fish or crustaceans.

860.1480 Meat, Milk, Poultry, and Eggs

D289422, W. Donovan, 9/25/03 (HED Chemistry Chapter of Cypermethrin RED)

D283584, D. McNeilly, 7/7/06

D334263  D. McNeilly, 11/29/06

Tolerances for residues of zeta-cypermethrin and its inactive R-isomers
are established [40 CFR §180.418(a)(2)] for the fat (1.0 ppm), meat
(0.2 ppm), and meat-byproducts (0.05 ppm) of cattle, goat, hog, horse,
and sheep.  The established tolerance for milk fat is 2.5 ppm
(reflecting 0.10 ppm in whole milk).  Tolerances for poultry fat, meat,
and meat byproducts and eggs are established at 0.05 ppm each. The HED
Residue Chemistry Chapter for the Cypermethrin RED (9/2003) concluded
that because the analytical method does not distinguish between residues
of cypermethrin and zeta-cypermethrin, tolerance levels for milk, meat,
and poultry commodities should be the same for cypermethrin and
zeta-cypermethrin.  Adequate ruminant and poultry feeding studies are
available and were summarized in the Cypermethrin RED.

The potential maximum dietary burden (MDB) of livestock to
zeta-cypermethrin residues was recently calculated to be 27.6 ppm for
beef and dairy cattle, 0.39 ppm for poultry, and 2.02 ppm for swine
under several earlier petitions (D283584, D. McNeilly, 7/7/06).  The
current petition for citrus fruits includes a new livestock feed (dried
pulp).  In addition, HED has recently revised its guidance on
calculating potential residues in livestock diets and updated the types
and percentages of feedstuffs listed in Table 1 of Guideline 860.1000. 
Therefore, the potential MDBs for livestock to zeta-cypermethrin
residues were recalculated using a reasonably balance diet for
livestock.  The dietary exposure was recalculated to be 19.8 ppm for
beef cattle, 22.0 ppm for dairy cattle, and 0.7 ppm for poultry and
swine (Table 5).

As the recalculated MDBs for cattle and swine are slightly lower than
previously determined, the existing tolerances for milk and cattle,
goat, hog, horses and sheep commodities are adequate.  The revised MDB
for poultry (0.7 ppm) is higher than previously calculated, but the data
still support tolerances in eggs and poultry commodities at 0.05 ppm.

Table 5.   Calculation of Dietary Burdens of Zeta-Cypermethrin Residues
to Livestock.

Feedstuff	Type 1	% Dry Matter2	% Diet 2	Established Tolerances (ppm)
Dietary Contribution (ppm) 3

Beef Cattle

Clover, hay	R	89	20	40.0	8.99

Trefoil, hay	R	85	20	40.0	9.41

Cotton, undelinted seed	P	88	15	0.5	0.085

Apple, wet pomace	C	40	20	2.0	1.00

Rice grain	C	88	20	1.5	0.34

TOTAL BURDEN	--	--	100	--	19.83

Dairy Cattle

Trefoil, hay	R	85	40	40.0	18.82

Clover, hay	R	25	5	40.0	2.25

Cotton, undelinted seed	P	88	15	0.5	0.085

Rice Grain	C	88	20	1.5	0.34

Apple, wet pomace	C	40	10	2.0 1	0.50

TOTAL BURDEN	--	--	100	--	22.00

Poultry

Cotton, meal	P	NA	20	0.5 1	0.10

Sorghum, grain	C	NA	60	0.5	0.30

Rice, grain	C	NA	20	1.5	0.30

 TOTAL BURDEN	--	--	100	--	0.70

Swine

Cotton, meal	P	NA	15	0.5 1	0.08

Flax, meal	P	NA	5	0.2 1	0.01

Sorghum, grain	C	NA	60	0.5	0.30

Rice, grain	C	NA	20	1.5	0.30

TOTAL BURDEN	--	--	100	--	0.69

1	R - Roughage, P – Protein source, C – Carbohydrate source. 
Residues in cottonseed meal, flax meal and wet apple pomace are based on
tolerances from the respective RACs.

860.1500 Crop Field Trials

46971402.de1 (Citrus fruits)

46969201.de1 (Safflower)

IR-4 has submitted field trial data for citrus and safflower.    SEQ
CHAPTER \h \r 1 The results from these studies are discussed below and
summarized in Table 6.  In addition, IR-4 is requesting that the
existing field trial data on fruiting vegetables and rice be use to
support expanded uses, i.e., to support  tolerances for okra and wild
rice.

Table 6.	  Summary of Residue Data from Crop Field Trials with
Zeta-Cypermethrin (EC and EW).

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

	n	Min.	Max.	HAFT1	Median	Mean	Std. Dev.

Citrus Fruits (Proposed use = 0.2 lb ai/A total application rate, 1-day
PHI)

Orange	0.20	1	24	<0.05	0.16	0.16	0.125	0.103	0.047

Lemon

	10	0.05	0.09	0.08	0.070	0.070	0.012

Grapefruit

	12	0.05	0.20	0.20	0.120	0.119	0.054

Combined Citrus

	46	<0.05	0.20	0.20	0.085	0.100	0.046

Safflower (Proposed use = 0.15 lb ai/A total application rate, 14-day
PHI)

Safflower seed	0.144-0.153	13-14	14	<0.05	0.15	0.145	0.05	0.065	0.034

Citrus Fruits.  A total of 23 citrus fruit field trials (12 orange, 5
lemon, 6 grapefruit) were conducted in Zones 3, 6 and 10 during the
2004/2005 growing season.  In each test, zeta-cypermethrin (1.5 lb/gal
EC or EW) was applied to citrus as four foliar applications during fruit
maturation at 0.05 lb ai/A/application with RTIs of 12-15 days, for a
total application of 0.2 lb ai/A/season (1x rate).  The EC formulation
was used in 12 tests (6 orange, 3 lemon, 3 grapefruit), and the EW
formulation was used in 11 tests (6 orange, 2 lemon, 3 grapefruit). 
Applications were made using ground equipment as either dilute sprays
(158-264 gal/A) in 11 trials or as concentrated sprays (52-97 gal/A) in
12 trials.  None of the applications included the use of any spray
adjuvants.  Single control and duplicate treated samples of citrus
fruits were collected from each test at 1 DALA, and additional duplicate
treated samples were collected at 7-8, 14-15 and 21-22 DALA from one
test each on lemon, orange and grapefruit, to assess residue decline. 
In four of the orange trials and two each of the lemon and grapefruit
trials, whole fruit were also subsampled and separated into peel and
pulp to assess residue levels in fresh pulp.  Samples were stored frozen
up to 8 months prior to analysis, an interval supported by available
storage stability data.

The GC/ECD method used to determine zeta-cypermethrin residues in/on
citrus fruits was adequately validated in conjunction with the analysis
of field trial samples.  The validated LOQ was 0.05 ppm, and the
reported LOD was 0.01 ppm.  

Although the different formulation types and different application
volumes were not compared in side-by-side tests, there was no
substantial difference in residue levels between the two formulations or
between the dilute and concentrated application volumes.  For all citrus
fruits harvested at 1 DALA, the overall average residues of
zeta-cypermethrin were 0.098 ppm for the EC formulation and 0.102 ppm
for the EW formulation, and 0.111 ppm for the dilute volume applications
and 0.090 ppm for concentrated volume applications.

Differences in residue levels were more pronounced between the different
types of citrus fruits.  Considering both types of formulations and
application volumes, zeta-cypermethrin residues at 1 DALA were highest
on grapefruits (0.05-0.20 ppm), followed by oranges (<0.05-0.16 ppm),
and lemons (0.05-0.09 ppm).  Overall average residues were 0.119 ppm
in/on grapefruit, 0.103 ppm in/on oranges, and 0.070 ppm in/on lemons. 
The HAFT residues were 0.20 ppm for grapefruit, 0.16 ppm for oranges,
and 0.08 ppm for lemons.  

Data from the three residue decline trials also showed that residues
in/on all three types of citrus fruit remained relatively unchanged from
1 to 22 DALA.  In addition, the analysis of fresh pulp subsamples from
eight of the tests indicated that residues were located primarily on the
fruit surface.  Zeta-cypermethrin residues were non-detectable (<0.01
ppm) in all 16 samples of pulp from all three types of citrus fruits.

Safflower.  In 5 field trials conducted during 2003 in Zones 5, 7 and
10, zeta-cypermethrin (1.5 lb/gal EC) was applied to safflower as three
broadcast foliar applications during bloom and seed development at rates
of 0.047-0.052 lb ai/A/application and RTIs of 10-18 days, for a total
of 0.144-0.153 lb ai/A/season (1x rate).  Two of the field trials also
included side-by-side tests using similar applications of a 1.5 lb/gal
EW formulation, at rates of 0.047-0.052 lb ai/A/application and RTIs of
13-15 days, for a total of 0.146-0.152 lb ai/A/season.  All applications
were made using ground equipment at volumes of 13-22 gal/A, and did not
include the use of any spray adjuvants.  Duplicate control and treated
samples of safflower seed were collected from each test at 13-14 DALA. 
Samples were stored frozen up to 14.9 months prior to analysis, an
interval supported by available storage stability data.

The GC/ECD method used to determine zeta-cypermethrin residues in/on
safflower was adequately validated in conjunction with  the analysis of
field trial samples.  The lowest level of method validation (LLMV) was
0.05 ppm in/on seeds, and the statistically calculated LOQ and LOD were
0.042 and 0.014 ppm, respectively.

  

In the two trials using side-by-side tests with the EC and EW
formulations, there were no differences in residues between the two
formulations.  Following the last of three broadcast foliar applications
totaling 0.144-0.153 lb ai/A, residues of zeta-cypermethrin were
<0.05-0.15 ppm in/on 14 samples of safflower seed harvested at 13-14
DAT.  Nine of the 14 samples had residues <0.05 ppm.  The average
residue was 0.065 ppm and the HAFT residue was 0.145 ppm.

Okra.  No field trial data on okra were submitted the current petitions.
 IR-4 is requesting that the available field trial data on fruiting
vegetables (PP#0F6207, D268861, Y. Donovan, 11/19/01) be used to support
expanding the use on fruiting vegetables to include okra.

Wild Rice.  No field trial data on wild rice were submitted the current
petitions.  IR-4 is requesting that the available field trial data on
rice (PP#9F6040, D258805, Y. Donovan, 5/22/01) be used to support
expanding the current use on rice to include wild rice.

Oilseed Commodities.  No field trial data for any oilseed commodity were
submitted with the current petition.  IR-4 is requesting that the
available field trial data on canola, sunflower and safflower be used to
support expanding the current use on other oilseed commodities.  They
also cite that a 0.2 ppm time-limited tolerance has been established to
support a Section 18 use for flax.

Oilseed Crop Definition:  Oilseeds include those crops from which oil is
extracted from their seed and used to produce edible or inedible oils as
well as a high-protein livestock meal.  Oils may be extracted from
plants by applying pressure to the seed, or by dissolving parts of the
plants in water or another solvent, and distilling the oil, or by
infusing parts of the plant in base oil.  The oilseeds are primarily
soybeans, sunflower seed, canola, rapeseed, safflower, flax seed, or
castor bean, mustard seed, peanut and cottonseed, used for the
production of cooking oils, protein meals for livestock and industrial
uses.

OPP is currently working with USDA/IR-4 in evaluating the establishment
of an Oilseed Crop Group 20, with three subgroups under that oilseed
crop group, each subgroup with representative commodities.  The three
pending subgroups under the Oilseeds crop group are as follows:

Subgroup 20A.  Rapeseed Subgroup (Representative commodity: Rapeseed,
canola varieties only): Borage, Crambe, Cuphea, Flax seed, Gold of
pleasure, Hare's-ear mustard, Lesquerella, Meadowfoam, Milkweed seed,
Mustard seed, Oil radish, Poppy seed, Rapeseed, Sesame, Sweet rocket.

Subgroup 20B.  Sunflower Subgroup (Representative commodity: Sunflower):
Castor oil plant, Chinese tallowtree, Euphorbia, Evening
primrose/common, Jojoba, Niger seed, Rose hip, Safflower, Stokes aster
seed, Sunflower, Tallowwood, Tea oil plant, Vernonia.

  

Subgroup 20C.  Cottonseed Subgroup (Representative commodity:
Cottonseed): Cottonseed.

Fury® 1.5 EC and Fury® 1.5 EW draft product labels are labeled for
multiple foliar applications of 0.05 lb ai/A (minimum interval of 7
days), for a maximum of 0.3 lb ai/A/season, with a PHI of 7 days.  The
proposed labels state that applications can be made aerially (2 gal/A
finished spray) or by  ground equipment by (10 gal/A finished spray). 
The maximum number of applications was not specified.

Canola field trial dare are available for translation to the pending
Subgroup 20A commodities , while both sunflower and safflower field
trial data are available for subgroup 20B commodities.   The canola data
(D283584, D. McNeilly; July 7, 2006) indicated that residues of
zeta-cypermethrin were 0.011-0.04 ppm in or on all 16 canola seed
samples at 7 DAT, and the average residues were calculated to be 0.025
ppm (below the LOQ).  The canola seed samples were harvested 7 days
after a single preplant soil and five broadcast foliar applications at
0.05 lb ai/A/application, for a total application of 0.3 lb ai/A.  The
residue data supported a tolerance of 0.05 ppm for canola seed. 
However, in order to harmonize with the Codex MRL on oilseeds (except
peanut) and take into account the commodity definition in 40 CFR
180.1(h), HED recommended that a tolerance of 0.2 ppm be established for
“rapeseed” (Note: this tolerance  will cover residues in both canola
and crambe).

Subgroup 20A Processed Commodities.  The maximum theoretical
concentration factor (OPPTS 860.1520, Table 1) for canola is 3x, and the
theoretical concentration factors based on separation into components
(OPPTS 860.1520, Table 3) are 1.9x for canola meal and 3.0x for oil. 
The determined processing factor for canola oil (1.4x) does not exceed
the theoretical concentration factor.

Table 7.  Residue Data from Canola Processing Study with
Zeta-Cypermethrin.

RAC	Processed Commodity	Total Rate

(lb ai/A) 	PHI 

(days)	Residues 1

(ppm)	Processing

Factor 2

Canola	Seed (RAC, processor sample)	0.50	7	0.415, 0.406  (0.411)	--

	Meal

	ND, ND  (<0.01)	<0.03x

	Refined oil

	0.499, 0.674  (0.587)	1.4x

1  Average residues are in parentheses.  ND = nondetectable (<0.01 ppm).

2  Processing factors were calculated using the RAC subsamples collected
at the processing facility. 

As shown in the table above, residues of zeta-cypermethrin decreased in
canola meal (<0.03x processing factor) and concentrated slightly in oil
(1.4x processing factor).  Although a marginal concentration in oil was
observed, HED did not recommend the establishment of tolerances for
canola oil and meal as any expected residues in these commodities, will
be covered by the recommended tolerance for rapeseed (which covers
canola).

Subgroup 20B Processed Commodities.  For the two regulated sunflower
seed commodities meal and refined oil, cypermethrin did not concentrate
in the meal but did in the refined oil by a factor of 1.4.  This
concentration factor was calculated by dividing the mean of the
processed commodity residue level, by the mean of the RAC sample and
subsample residue levels.  HED concluded that the processing study was
adequate and can be bridged to zeta-cypermethrin.  Multiplying the
concentration factor by the highest field trial residue (PP# 1F3994,
D165012, J. Herndon, 9/17/91) gives 0.31 ppm (1.4 x 0.22 ppm = 0.31 ppm)
which is more than the 0.2 ppm recommended tolerance for sunflower seed.
 Therefore, a separate tolerance was recommended for sunflower refined
oil at 0.4 ppm.  Cypermethrin also concentrated 1.4-fold in crude oil. 
Therefore, a 0.4 ppm tolerance should be established for refined oil for
all Subgroup 20B commodities.  See Table 9 for a detailed listing of the
tolerances required.

Conclusions.  The citrus and safflower field trials are adequate and
support the proposed use patterns.  An adequate number of tests were
conducted on each crop in the appropriate geographical regions.  Samples
were analyzed for the residues of concern using an adequate method, and
the sample storage conditions and intervals are supported by available
or concurrent storage stability data. 

Utilizing the tolerance harmonization spreadsheet and the available
residue data on grapefruit, which had the highest residues of the three
representative citrus crops, the appropriate tolerance for the citrus
fruits crop group is 0.35 ppm.  The available safflower residue data
support the proposed 0.2 ppm tolerance.

Although no field trial data are available on okra, HED has recommended
that okra be included in the fruiting vegetable crop group.  As the
proposed use on okra is identical to the current use on fruiting
vegetables, the available residue data on representative fruiting
vegetables (Crop Group 8) will support a 0.2 ppm tolerance on okra.

The existing residue data on rice will support the proposed 1.5 ppm
tolerance on wild rice grain as the proposed use on wild rice is
identical to the existing use on rice.  

The existing residue data for rapeseed, sunflower, and safflower will
support the proposed 0.2 ppm tolerance for the oilseed commodities in
the proposed Crop Group 20 (as defined above), as the proposed uses are
identical to the existing use of either canola (for the proposed
Subgroup 20A commodities) or sunflower (for the proposed Subgroup 20B
commodities).  Additional, tolerances are required for refined oil for
all of the Subgroup 20B commodities (see Table 9 for details).

860.1520 Processed Food and Feed

46971402.de2 (Citrus fruits)

46969201.de2 (Safflower)

  SEQ CHAPTER \h \r 1 Table 8.	Summary of Processing Factors for
Zeta-Cypermethrin.

RAC	Processed Commodity	Processing Factor

Orange	Dried Pulp	9x

	Orange Oil	19x

	Juice	<0.3x

Safflower Seed	Safflower Meal	<1x

	Safflower Oil	<1x

Citrus Fruits.  Zeta-cypermethrin (1.5 lb/gal EC) was applied to orange
trees as four broadcast foliar applications during late fruit
development at 0.05 lb ai/A and at RTIs of 13-14 days, for a total of
0.2 lb ai/A (1x rate).  Applications were made using ground equipment at
volumes of 72-74 gal/A, and did not include the use of any spray
adjuvants.  A single bulk control sample and duplicate bulk treated
samples of citrus fruits were collected at 1 DALA, and immediately
shipped under refrigerated conditions to the processing facility.  Whole
fruit were processed into juice, dried pulp and oil using simulated
commercial procedures.  Samples of whole fruit were stored frozen for up
to 8 months prior to analysis, and processed fractions were analyzed
within one month of collection.  Adequate data are available to support
the storage interval for whole fruits, and no storage stability data are
required to support the processed fractions.

 

The GC/ECD method used to determine zeta-cypermethrin residues in whole
fruit, juice, oil and dried pulp was adequately validated in conjunction
with the analysis of processing study samples.    The validated LOQ was
0.05 ppm for each matrix, and the reported LOD was 0.01 ppm.

Following four foliar applications at a 1x rate, average residues were
0.03 ppm in/on whole fruit harvested at 1 DALA.  Average residues after
processing were <0.01 ppm in juice, 0.27 ppm in dried pulp, and 0.57 ppm
in oil.  These residue levels corresponded to processing factors of
<0.03x for juice, 9x for dried pulp, and 19x for citrus oil.  The
maximum theoretical processing factor for citrus is 1000x (oil).

Safflower.  In a single field trial conducted in 2003, zeta-cypermethrin
(1.5 lb/gal EC) was applied to safflower as three broadcast foliar
applications during seed development at rates of 0.049-0.051 lb
ai/A/application and at RTIs of 10-18 days, for a total of 0.151 lb
ai/A/season (1x rate).  Applications were made using ground equipment at
volumes of 13-14 gal/A, and did not include the use of any spray
adjuvants.  Single bulk control and treated samples of seed were
collected at maturity, 13 DALA.  Seeds were processed into meal and oil
using simulated commercial procedures.  Samples of seeds, meal and oil
were stored frozen for 10-14.8 months prior to analysis; these intervals
are supported by available storage stability data.

The GC/ECD method used to determine zeta-cypermethrin residues in
safflower seeds, meal and oil was adequately validated in conjunction
with the analysis of processing study samples. The LLMV was 0.05 ppm for
all three matrices, and the statistically calculated LOQs were 0.042,
0.035, and 0.049 ppm for seeds, meal and oil, respectively.  The
calculated LOD were 0.014, 0.012, and 0.016 ppm.

Following three applications totaling 0.151 lb ai/A, residues were 0.05
ppm in safflower seed harvested at 13 DALA.  Residues in safflower meal
and oil were <0.05 ppm, indicating that zeta-cypermethrin residues do
not concentrate in safflower processed fractions.

Conclusions.  The orange and safflower processing studies are adequate
and support the proposed use pattern.  As residues were reduced in
safflower oil and meal and orange juice, separate tolerances are not
required for these commodities.  However, residues were shown to
concentrate appreciably in orange dried pulp (9x) and oil (19x).  Based
on the HAFT residues of 0.20 ppm from the citrus field trials and these
processing factors, the maximum expected residues in citrus dried pulp
and oil would be 1.8 and 3.8 ppm respectively.  These values will
support tolerances of 1.8 ppm for dried citrus pulp and 4.0 ppm for
citrus oil.

860.1650 Submittal of Analytical Reference Standards

  SEQ CHAPTER \h \r 1 Analytical standards for zeta-cypermethrin are
currently available in the National Pesticide Standards Repository.

860.1850 and 1900 Confined and Field Accumulation in Rotational Crops

The HED Chemistry Chapter of the Cypermethrin RED (D289422, W. Donovan,
9/25/03) reported that adequate confined and limited field rotational
crop studies are available for cypermethrin.  The results of the limited
field rotational crop study indicate that residues of cypermethrin and
its metabolites were nondetectable (<0.01 ppm) in/on the rotational crop
commodities of leafy vegetables, root and tuber vegetables, and cereal
grain crops that were planted 30 days after the soil plots were treated
with cypermethrin at 0.5 lb ai/A (1.7x the maximum seasonal rate).  The
study supports the labeled PBI of 30 days, and no additional rotational
crop data are required for cypermethrin.  This conclusion also applies
to zeta-cypermethrin.

860.1550 Proposed Tolerances

Tolerances for residues of zeta-cypermethrin are listed under 40 CFR
§180.418(a)(2), and are expressed in terms of for zeta-cypermethrin and
its inactive R-isomers.  The inclusion of the inactive R-isomers in the
tolerance expression is appropriate because the enforcement methods
listed in PAM Volume II are not stereospecific; thus no distinction is
made between residues of cypermethrin (all eight stereoisomers) and
zeta-cypermethrin (an enriched isomer form of cypermethrin).  The
proposed and recommended tolerances for the each commodity are listed in
Table 9.

For Citrus Fruits, Crop Group 10, the residue data from grapefruit were
utilized to recommend an appropriate tolerance, as residues in/on
grapefruit were higher than the other two representative crops of
oranges and lemons.  Using the grapefruit residue data and the tolerance
harmonization spreadsheet (Appendix II), the appropriate tolerance for
citrus fruits was calculated to be 0.35 ppm.  Although MRLs have been
establish on citrus fruits by both Canada (1.0 mg/kg) and Codex (2.0
mg/kg; Appendix I), harmonization is not possible as the MRL levels are
considerably above the residues resulting from the proposed use rate in
the U.S.

For safflower, the recommended tolerance level of 0.2 ppm is based on
the maximum residues (0.15 ppm) observed in the field trials.  The
tolerance harmonization spreadsheet was not utilized as 9 of the 14
safflower seed samples had residues <LOQ.  In addition, the 0.2 ppm
tolerance on safflower seed is harmonized with the current Codex MRL of
0.2 mg/kg on oilseeds.

As residues did not concentrate in orange juice or safflower meal and
oil, separate tolerances are not required for these processed
commodities.  However, residues were shown to concentrate in orange
dried pulp (9x) and oil (19x).  Based on the HAFT residues of 0.20 ppm
from the citrus field trials (grapefruit) and the above processing
factors, the maximum expected residues in citrus dried pulp and oil
would be 1.8 and 3.8 ppm respectively.  Considering HED guidance on
rounding of residue values for determining tolerances (ChemSAC memo,
3/23/05), the appropriate tolerances for citrus dried pulp and oil would
be 1.8 and 4.0 ppm, respectively.

As the proposed use on okra is identical to the current use on fruiting
vegetables, the existing field trial data on fruiting vegetables will
support the proposed 0.2 ppm tolerance on okra.  HED has recommended
that okra be included in the fruiting vegetable crop group; however,
until the new crop group regulation is published a separate tolerance
will be required for okra.  Similarly, the existing residue data on rice
will support the proposed 1.5 ppm tolerance on wild rice grain as the
proposed use on wild rice is identical to the existing use on rice.

Based on current and proposed tolerances for livestock feedstuffs,
residues are not expected to exceed the established tolerances for meat,
milk, poultry, and eggs when the maximum dietary burden is extrapolated
with the feeding levels used in the available animal feeding studies. 
Therefore, no revision of the existing animal commodity tolerances is
required.

Table 9. 	Tolerance Summary for Zeta-Cypermethrin.

Commodity	Proposed Tolerance (ppm)	Recommended Tolerance (ppm)	Comments;

Correct Commodity Definition

Fruit, citrus, group 10	0.25	0.35	Adequate residue data are available on
oranges, lemons and grapefruit.  The tolerance was calculated using the
tolerance harmonization spreadsheet and the residue data from
grapefruits, which had the highest residues of the three representative
crops.

Citrus, dried pulp	0.5	1.8	Considering processing factors for citrus
dried pulp (9x) and oil (19x) and the HAFT residues of 0.20 ppm from the
citrus field trials, the maximum expected residues in dried pulp and oil
would be 1.8 and 3.8 ppm, respectively.

Citrus, oil	0.9	4.0

	Okra	0.2	0.2	Adequate residue data are available on fruiting
vegetables.  These data will be translated to support a separate
tolerance on okra at the same level.

Safflower	0.2	0.2	Adequate residue data are available.

Safflower, seed

Rice, wild, grain	1.5	1.5	Adequate residue data are available on rice. 
These data will be translated to support a separate tolerance on wild
rice at the same level.

Oilseed commodities

(proposed Subgroup 20A):

Borage, seed

Crambe, seed

Cuphea, seed

Echium, seed	

Flax, seed (see note)

Gold of pleasure, seed

Hare's-ear mustard, seed

Lesquerella, seed

Lunaria, seed

Meadowfoam, seed

Milkweed, seed

Mustard, seed

Oil radish, seed

Poppy, seed 

Sesame, seed

Sweet rocket, seed

Oilseed commodities

(proposed Subgroup 20B):

Castor oil plant, seed 

Chinese tallowtree, seed

Euphorbia, seed

Evening primrose, seed

Jojoba, seed

Niger seed, seed

Rose hip, seed	

Stokes aster, seed

Tallowwood, seed

Tea oil plant, seed

Vernonia, seed	

0.2

0.2	

0.2

0.2	Adequate residue data are available for canola (Subgroup 20A) and
sunflower (Subgroup 20B).  These data will be translated to support
separate tolerances for each oilseed commodity at the same level. 
(Note: When the Flax seed permanent tolerance is established the
temporary tolerance should be cancelled.)

Subgroup 20B

Oilseed, refined oil

Castor oil plant, refined oil

Chinese tallowtree, refined oil

Euphorbia, refined oil

Evening primrose, refined oil

Jojoba, refined oil

Niger seed, refined oil

Rose hip, refined oil

Stokes aster, refined oil

Tallowwood, refined oil

Tea oil plant, refined oil

Vernonia, refined oil	--	0.4	Adequate processing data are available for
sunflower.  These data will be translated to support separate tolerances
for all Subgroup 20B oilseed commodities at the same level.

References

	  SEQ CHAPTER \h \r 1 D  SEQ CHAPTER \h \r 1 269584;   SEQ CHAPTER \h
\r 1 Cypermethrin and Zeta-Cypermethrin – Conclusions of the Meeting
of Metabolism Assessment Review Committee (10/10/00); Y. Donovan;   SEQ
CHAPTER \h \r 1 11/3/00.

  SEQ CHAPTER \h \r 1 

	  SEQ CHAPTER \h \r 1 D  SEQ CHAPTER \h \r 1 258805;   SEQ CHAPTER \h
\r 1 PP#9F6040  Zeta-Cypermethrin - Proposal for Permanent Tolerance on
Rice and Processed Rice Products.  Evaluation of Analytical Method and
Magnitude of the Residue Data;   SEQ CHAPTER \h \r 1 Y. Donovan;   SEQ
CHAPTER \h \r 1 5/22/01.

	  SEQ CHAPTER \h \r 1 D  SEQ CHAPTER \h \r 1 268861;   SEQ CHAPTER \h
\r 1 PP#0F6207.  Zeta-Cypermethrin – Proposal for Permanent Tolerance
on Cereal Grains, Legumes, Soy Beans, and Fruiting Vegetables. 
Evaluation of Analytical Method and Magnitude of the Residue Data;   SEQ
CHAPTER \h \r 1 Y. Donovan;   SEQ CHAPTER \h \r 1 11/19/01.

	  SEQ CHAPTER \h \r 1 D  SEQ CHAPTER \h \r 1 289422;   SEQ CHAPTER \h
\r 1 Cypermethrin (PC Code 109702) HED Chemistry Chapter of the
Reregistration Eligibility Decision (RED):  Summary of Product and
Residue Chemistry Residue Data.  Reregistration Case 2130; W  SEQ
CHAPTER \h \r 1 . Donovan;   SEQ CHAPTER \h \r 1 9/25/03.

	  SEQ CHAPTER \h \r 1 D283584;   SEQ CHAPTER \h \r 1 Zeta-Cypermethrin.
 Petitions (PP#s 3F6577, 3E6677, 2F6444, 4F6893, and 5F6896) for the
Establishment of Tolerances on Various Raw Agricultural, Processed
Commodities and Food Items in Food Handling Establishments.  Summary of
Analytical Chemistry and Residue Data; D. McNeilly;   SEQ CHAPTER \h \r
1   SEQ CHAPTER \h \r 1 7/07/06.

D334263.  Zeta-cypermethrin: Revised Human Health Risk Assessment for
Proposed Uses on Numerous Raw Agricultural Commodities.  Petitions:
3F6577, 3E6677, 2F6444, 4F6893, and 5F6896 for the Establishment of
Tolerances on Various Raw Agricultural, Processed Commodities and Food
Items in Food Handling Establishments.  Dennis McNeilly, 11/29/2006.

  SEQ CHAPTER \h \r 1 Attachments:  

Appendix I - International Residue Limits Status 

Appendix II- Tolerance Spreadsheet Calculations.

Appendix I – International Tolerances.

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name: 

(s-cyano(3-phenoxyphenyl) methyl (±)cis, trans 3-
(2,2-dichloroethenyl)-2,2- dimethylcyclo propanecarboxylate	Common Name:

Zeta-cypermethrin	x Proposed toler湡散

 Reevaluated tolerance

 Other	Date: 12/18/05

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
Numbers:  6E7132, 6E7133

DP Numbers:  335223, 335226

Other Identifier: EPA Reg. Nos. 279-3125, 279-3126

Residue definition (step 8/CXL):

 No Limits  

   No limits for the crops requested	 No Limits

X No Limits for the crops requested

Residue definition:

cypermethrin: (RS)-alpha-cyano-3-phenoxy-benzyl (1RS,3RS)-(1RS,
3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate	Residue
definition:  zeta-cipermetrina

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

Apples	1.0	Cottonseed	0.5

Celery	1.0	Onion	0.1

Citrus fruit	1.0	corn (maize)	0.05

Beans	0.5	Soybean	0.05

Broccoli	0.5

Brussels sprouts	0.5

Cabbage	0.5

Cauliflower	0.5

Grapes	0.5

Pears	0.5

Tomatoes	0.3

Peaches/nectarines	0.2

Strawberries	0.2

Notes/Special Instructions:

Appendix II - Tolerance Assessment Calculations.

The Agency’s Guidance for Setting Pesticide Tolerances Based on Field
Trial Data was utilized for determining appropriate tolerance levels on
citrus fruits.  The dataset used to establish the tolerance for
zeta-cypermethrin residues on citrus fruits consisted of field trial
data representing applications of the appropriate EC and EW formulations
at 1x the maximum use rate.  As specified by the Guidance for Setting
Pesticide Tolerances Based on Field Trial Data SOP, the field trial
application rates were within 25% of the maximum label application rate,
and the PHI is consistent with the appropriate stage of maturity and the
proposed PHI.  The residue values used to calculate tolerance are
provided in Table II-1.  

The residue data for grapefruits was utilized to determine the
appropriate tolerance for the citrus fruits crop group as grapefruits
had the highest residues of the three representative crops.  Residues
were lower in both oranges (<0.05-0.16 ppm) and lemons (0.05-0.09 ppm).

 

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s was entered into the tolerance spreadsheet.  Visual inspection of the
lognormal probability plot (Figure II-1) indicates that the dataset is
reasonably lognormal and the result from the approximate Shaprio-Francia
test statistic (Figure II-2) confirms that assumption.  The calculated
tolerance level for citrus fruits 0.35 ppm.

For safflower, the recommended tolerance level of 0.2 ppm is based on
the maximum residues (0.15 ppm) observed in the field trials.  The
tolerance harmonization spreadsheet was not utilized as 9 of the 14
safflower seed samples had residues <LOQ.  In addition, the 0.2 ppm
tolerance on safflower seed is harmonized with the current Codex MRL of
0.2 mg/kg on oilseeds.



Table II-1.	Zeta-Cypermethrin Residue Data on Citrus Fruits.

Regulator:	EPA

Chemical:	Zeta-cypermethrin

Crop:	Oranges	Lemons	Grapefruit

PHI:	1 day

App. Rate:	0.2 lb ai/A

Submitter:	IR-4

MRID Citation:	MRID 46971402

	Residues	Residues	Residues

	0.05	0.08	0.12

	0.05	0.07	0.16

	0.16	0.08	0.20

	0.13	0.05	0.06

	0.05	0.06	0.05

	0.12	0.08	0.11

	0.11	0.09	0.12

	0.14	0.06	0.15

	0.05	0.07	0.20

	0.05	0.06	0.07

	0.15

0.05

	0.13

0.14

	0.05

	0.05

	0.16

	0.14

	0.05

	0.13

	0.16

	0.16

	0.05

	0.05

	0.14

	0.13

Values below the LOQ (0.05 ppm) are designated in bold.

Figure II-1.	Lognormal Probability Plot for Zeta-Cypermethrin Residues
in/on Grapefruits.

Figure II-  SEQ Figure_II \* ARABIC  1 .	Data Summary Table for
Zeta-Cypermethrin Residues In/On Grapefruits.

Summary of Analytical Chemistry and Residue Data

Zeta-Cypermethrin                                                       
   DP Numbers 335223, 335226

						Page 	  PAGE  5  of   NUMPAGES  28 

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