![](media/image1.wmf){width="1.125in" height="1.0534722222222221in"}

**UNITED STATES ENVIRONMENTAL PROTECTION AGENCY**

WASHINGTON, D.C. 20460

OFFICE OF PREVENTION,

PESTICIDES AND TOXIC

SUBSTANCES

#### MEMORANDUM

**Date: 06-APR-2006**

Subject: Bifenthrin. Petitions for Tolerances and Uses on Tuberous and
Corm Vegetables (Subgroup 1C; PP#3E6882), Leafy *Brassica* Greens
(Subgroup 5B; 2E6451), Dried Shelled Peas and Beans (Subgroup 6C;
2E6423), and Cilantro (4E6843), and a Label Amendment for Use on
Tobacco. Summary of Analytical Chemistry and Residue Data.

> []{.mark}

+-----------+---------------------+-----------+-----------------------+
| DP#s:     | ## 310089,          | De        | 305246, 305406,       |
|           | 310874, 313738, 313 | cision#s: | 327616, 331702,       |
|           | 817, 313299, 317208 |           | 351451, 351522        |
+-----------+---------------------+-----------+-----------------------+
| PC Code:  | 128825              | MRID#s:   | 45624701, 45660301,   |
|           |                     |           | 45794202, 45794203,   |
|           |                     |           | 46045001, 46279701    |
+-----------+---------------------+-----------+-----------------------+
| 40 CFR    | 180.442             | Chemical  | Synthetic Pyrethroid  |
|           |                     | Class:    |                       |
+-----------+---------------------+-----------+-----------------------+

**From:** Sarah J. Levy, M.S., Chemist

George F. Kramer, Ph.D., Chemist

Registration Branch 1 (RAB1)

Health Effects Division (HED; 7509C)

**Through:** P.V. Shah, Ph.D., Branch Senior Scientist

RAB1/HED (7509C)

**To:** Number range CHAPTERGeorge LaRocca, PM 13

Insecticide Branch

Registration Division (RD; 7505C)

This document was originally prepared under contract by Dynamac
Corporation (1910 Sedwick Rd., Building 100, Suite B; Durham, NC 27713;
submitted 25-OCT-2005). The document has been reviewed by the HED and
revised to reflect current OPP policies.

**Executive Summary**

Bifenthrin
(2-methyl\[1,1'-biphenyl\]3-yl)methyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropanecarboxylate)
is a synthetic pyrethroid that is currently used for control of insects
on a variety of fruit, vegetable and field crops. Permanent tolerances
are established for residues of bifenthrin in/on plant and livestock
commodities at levels ranging from 0.05 ppm (limit of quantitation
(LOQ)) on various commodities to 10.0 ppm in/on dried hop cones \[40 CFR
§180.442(a)\].

###### The Interregional Research Project No. 4 (IR-4) has submitted a series of petitions (PP#s: 2E6451, 2E6423, 3E6882 and 4E6843) proposing the use of bifenthrin, formulated as a 2 lb/gal emulsifiable concentrate (EC) or a 1.15% granule (G), on tuberous and corm vegetables, *Brassica* leafy greens, dried shelled peas and beans (except soybeans), and cilantro. The proposed use for tuberous and corm vegetables includes an at-planting application of the EC or G formulations at 0.3 lb ai/A, followed by up to two foliar applications of the EC formulation at 0.1 lb ai/A/application, with a retreatment interval (RTI) of 21 days and a 21-day pre-harvest interval (PHI). The uses on *Brassica* leafy greens, dried peas and beans, and cilantro (coriander) are for 2 to 5 broadcast foliar applications of the EC formulation at 0.1 lb ai/A/application, with a RTI of 7 days (when specified) and PHIs of 3-14 days. In conjunction with these uses, IR-4 is proposing tolerances for residues on tuberous and corm vegetables (subgroup 1C) at 0.1 ppm, *Brassica* leafy greens (subgroup 5B) at 3.0 ppm, dried shelled pea and bean, except soybean, (subgroup 6C) at 0.1 ppm, cilantro leaves and seed at 5.0 ppm, and cilantro dried leaves at 30.0 ppm. FMC Corporation is also requesting a label amendment for its EC formulation allowing use of bifenthrin on tobacco as a pre-plant or at-transplanting application at 0.1 lb ai/A followed by foliar application(s) at 0.05 lb ai/A/application.

Based on the previously-submitted cotton, corn, apple, hen, and goat
metabolism data and the currently-submitted potato metabolism study, the
nature of bifenthrin residues in plants and livestock is understood. The
residue of concern is bifenthrin *per se* in both primary and rotated
crop commodities and in livestock.

Adequate gas chromatography (GC)/electron-capture detection (ECD)
methods are available for enforcing tolerances of bifenthrin in plant
and livestock commodities. The available methods for plant commodities
generally involve extraction of the sample with acetone, partitioning
with hexane, purification using a Florisil column, and analysis of
residues by GC/ECD. The limit of quantitation (LOQ) for these methods is
0.05 ppm. Samples from the current field trials and the potato
processing study were analyzed using methods that are modifications to
one of the current enforcement methods (P-2550 M), with variations in
extraction solvents and detection methods. Residues of bifenthrin in/on
mustard greens and cilantro (leaves and seeds) were determined using a
GC/ECD method (FMC Report P-2132). For this method, residues are
extracted with hexane, concentrated, and cleaned up using a Florisil
column, then analyzed by GC/ECD. Residues in/on potato fractions and
dried beans and peas were determined using a GC/mass-selective detection
(MSD) method (FMC Report P-3426). For this method, residues are
extracted with acetone, concentrated, and purified by silica-gel
solid-phase extraction (SPE). The residues are then analyzed by GC/MSD,
using the m/z 181 ion for quantitation. Residues in/on green tobacco
were determined using a related GC/MSD method (FMC Report P-3457). For
this method, residues are extracted with acetone/water, partitioned into
hexane, and cleaned up with a SPE column, and analyzed by GC/MSD. For
each of the above methods, the LOQ for bifenthrin is 0.05 ppm, and the
reported limit of detection (LOD) is 0.01 ppm. Each of these methods was
adequately validated in conjunction with analysis of samples from the
field trials or processing study.

The field trials on potatoes, mustard greens, dried beans and peas,
cilantro, and tobacco are Number range CHAPTERadequate. An adequate
number of trials were conducted reflecting the proposed use patterns in
the appropriate geographic regions, and the appropriate commodities were
collected at the proposed PHIs. Samples were analyzed using adequate
analytical methods, and the sample storage intervals are supported by
the available storage stability data.

Following an at-planting soil application and two foliar applications of
bifenthrin at 1x the proposed rate, residues were \<0.05 ppm (\<LOQ)
in/on all potatoes harvested at 21 days after the final application
(DAT). Residues on mustard greens harvested 6-7 DAT were \<0.05-2.05 ppm
following four foliar applications of bifenthrin (EC) totaling \~0.4 lb
ai/A (1x). In the dried bean and pea field trials, residues on dried
beans harvested 13-15 DAT were \<0.05-0.10 ppm following three foliar
applications of bifenthrin (EC) totaling 0.3 lb ai/A (1x), and residues
on dried peas harvested 14-15 DAT were \<0.05 ppm following two foliar
applications of bifenthrin (EC) totaling 0.2 lb ai/A (1x). Following
five foliar applications of bifenthrin (EC) to cilantro totaling \~0.5
lb ai/A (1x), residues at 3 DAT were 1.98-4.83 ppm in/on fresh leaves,
14.93-16.25 ppm in/on dried leaves, and 3.66-3.69 ppm in/on seeds. In
the tobacco field trials, residues of bifenthrin were \<0.05 ppm in/on
all green tobacco samples harvested at normal maturity following either
a preplant or at-transplanting application of bifentrhin (EC or G) at
0.1 lb ai/A and a single foliar application of bifenthrin (EC) at 0.05
or 0.10 lb ai/A (1x).

[]{.mark}

The available potato processing study is adequate. Because bifenthrin
residues were \<LOQ (\<0.05 ppm) in all samples from the potato field
trials and in potato tubers and all processed fractions from the
processing study conducted at a 3x rate, HED concludes that residues of
bifenthrin in wet peel are unlikely to exceed the LOQ when bifenthrin is
applied at a 1x rate. Therefore, a separate tolerance will be not
required for residues in/on processed potato fractions. In addition, a
comparison of residues in/on fresh and dried cilantro leaves indicates
that there is a 5.7x processing factor for dried cilantro leaves. Based
on highest-average field-trial (HAFT) residues of 3.96 ppm in/on fresh
leaves, the maximum expected residues in/on dried cilantro leaves would
be 22.6 ppm.

The proposed tolerances for plant commodities will not have any impact
on the current tolerances for livestock commodities. The only proposed
crop use with any regulated livestock feedstuffs is potato (processed
potato waste and culls), and the addition of these commodities to
livestock diets will not increase the dietary exposure of livestock
calculated in the Bifenthrin Number range CHAPTERTolerance Reassessment
Eligibility Decision (TRED) (S. Levy, 22-AUG-2002; DP#283808).

Adequate confined and field rotational crop studies are available to
support the proposed uses. Based on the results of these rotational crop
studies, HED concludes that the current rotational crop plant-back
interval is acceptable and that tolerances for rotated crops are not
necessary.

[]{.mark}

Number range CHAPTER**Regulatory Recommendations and Residue Chemistry
Deficiencies**

Provided revised Sections B and F are submitted, HED concludes there are
no residue chemistry data requirements that would preclude establishing
permanent tolerances for residues of bifenthrin *per se* at 0.05 ppm
in/on tuberous and corm vegetables (subgroup 1C), 3.5 ppm in/on leafy
*Brassica* greens (subgroup 5B), 0.15 ppm in/on dried shelled pea and
beans, except soybean (subgroup 6C), 5.0 ppm in/on coriander leaves and
seeds, and 25 ppm in/on coriander dried leaves. **Revised Section Fs
should be submitted** with the correct tolerance level and commodity
definitions, where appropriate (see Table 6). Also, the use directions
for dried beans and peas should be amended to specify a minimum RTI of 7
days

The available field trial data will also support the use of bifenthrin
(EC) on tobacco, for which tolerances are not required. As residues were
\<0.1 ppm in/on all samples of green tobacco from the field trials, no
additional residue data are required on tobacco. However, FMC should
amend its use directions for tobacco to specify the maximum number of
foliar applications allowed and the maximum seasonal use rate. The
available tobacco field trials will support use of the 2 lb/gal EC as
either a broadcast pre-plant soil application at up to 0.1 lb ai/A or an
in-furrow water drench application at transplant at up to 0.1 lb ai/A,
followed by a single broadcast foliar application up to lay-by at up to
0.1 lb ai/A, for a maximum seasonal use rate of 0.2 lb ai/A. **A revised
Section B should be submitted.**

A human-health risk assessment for bifenthrin will be prepared in a
separate document.

**Background**

Bifenthrin is a synthetic pyrethroid insecticide (MOA Group 3) that is
registered to FMC Corporation for control of insects on a variety of
fruit, vegetable, and field crops. Tolerances are established for
residues of bifenthrin *per se* in/on plant and livestock commodities at
levels from 0.05 ppm (LOQ) on various commodities to 10.0 ppm on dried
hop cones \[40 CFR 180.442(a)\].

The IR-4 has submitted a series of petitions (2E6451, 2E6423, 3E6882 and
4E6843) proposing the use of bifenthrin, formulated as a 2 lb/gal EC or
a 1.15% G, on tuberous and corm vegetables, *Brassica* leafy greens,
dried and shelled peas and beans (except soybeans), and cilantro. In
conjunction with these uses, the petitioner is proposing the following
tolerances:

###### Vegetable, tuberous and corm, subgroup 1C 0.1 ppm

###### *Brassica*, leafy greens, subgroup 5B 3.0 ppm

###### Pea and bean, dried shelled, except soybean, subgroup 6C 0.1 ppm

###### Cilantro, leaves 5.0 ppm

###### Cilantro, dried leaves 30.0 ppm

###### Coriander, seed 5.0 ppm

In addition, FMC has proposed amending the 2 lb/gal EC formulation to
include uses on tobacco (non-food/feed). Number range CHAPTERThe
nomenclature and physicochemical properties of bifenthrin are presented
below in Tables 1 and 2.

+-------------------+--------------------------------------------------+
| **Table 1.        |                                                  |
| Nomenclature of   |                                                  |
| Bifenthrin**      |                                                  |
+===================+==================================================+
| Compound          | ![](media/image2.wmf){width="2.75in"             |
|                   | height="1.0256944444444445in"}                   |
+-------------------+--------------------------------------------------+
| Common name       | Bifenthrin                                       |
+-------------------+--------------------------------------------------+
| Company           | Capture^®^                                       |
| experimental      |                                                  |
| names             |                                                  |
+-------------------+--------------------------------------------------+
| Molecular weight  | 422.88                                           |
+-------------------+--------------------------------------------------+
| IUPAC name        | 2-methylbiphenyl-3-ylmethy                       |
|                   | l(*Z*)-(1*RS*,3*RS*)-3-(2-chloro-3,3,3-trifluoro |
|                   | prop-1-enyl)-2,2-dimethylcyclopropanecarboxylate |
|                   |                                                  |
|                   | or                                               |
|                   |                                                  |
|                   | 2-methylbiphenyl-3-ylmet                         |
|                   | hyl(*Z*)-(1*RS*)-cis-3-(2-chloro-3,3,3-trifluoro |
|                   | prop-1-enyl)-2,2-dimethylcyclopropanecarboxylate |
+-------------------+--------------------------------------------------+
| CAS name          | *rel*-2-methyl(1,1\'-biphenyl)-3-yl)             |
|                   | meth                                             |
|                   | yl(1*R*,3*R*)-3-((1*Z*)-2-chloro-3,3,3-trifluoro |
|                   | -1-propenyl)-2,2-dimethylcyclopropanecarboxylate |
+-------------------+--------------------------------------------------+
| CAS \#            | 82657-04-03                                      |
+-------------------+--------------------------------------------------+
| End-use           | 2.0 lb/gal EC and 1.5% G                         |
| products/EP       |                                                  |
+-------------------+--------------------------------------------------+

+--------------------------+--------------------------+-----------------+
| Table 2. Physicochemical |                          |                 |
| Properties of the        |                          |                 |
| Technical Grade          |                          |                 |
| Bifenthrin               |                          |                 |
+==========================+==========================+=================+
| Parameter                | Value                    | Reference       |
+--------------------------+--------------------------+-----------------+
| Melting range            | 68-70.6ºC                | Product         |
|                          |                          | Chemistry       |
|                          |                          | Chapter of TRED |
+--------------------------+--------------------------+-----------------+
| pH                       | NA                       |                 |
+--------------------------+--------------------------+-----------------+
| Density at 24°C          | 1.26 g/mL                |                 |
+--------------------------+--------------------------+-----------------+
| Water solubility         | \<0.1 g/L               |                 |
+--------------------------+--------------------------+-----------------+
| Solvent solubility       | 8.9 in heptane and       |                 |
| (g/100 mL)               | methanol                 |                 |
|                          |                          |                 |
|                          | 125 in acetone,          |                 |
|                          | chloroform, ether,       |                 |
|                          | methylene chloride, and  |                 |
|                          | toluene                  |                 |
+--------------------------+--------------------------+-----------------+
| Vapor pressure (Pa) at   | 2.41 x 10^-5^            |                 |
| 25°C                     |                          |                 |
+--------------------------+--------------------------+-----------------+
| Dissociation constant    | NA                       |                 |
| (pK~a~)                  |                          |                 |
+--------------------------+--------------------------+-----------------+
| Octanol/water partition  | \>1 x 10 ^6^             |                 |
| coefficient) Kow         |                          |                 |
+--------------------------+--------------------------+-----------------+
| UV/visible absorption    | NA                       |                 |
| spectrum                 |                          |                 |
+--------------------------+--------------------------+-----------------+

NA = Not available

**860.1200 Directions for use**

## There are currently four bifenthrin end-use products (EPs) registered to FMC for use on food/feed crops. One is a 2 lb/gal EC formulation marketed under the trade name Capture^®^ 2EC Insecticide/Miticide (EPA Reg. No. 279-3069) and another is a 1.15% G formulation marketed under the trade name Capture^®^ 1.15G Insecticide (EPA Reg. No. 279-3244). IR-4 is supporting the use of the 2 lb/gal EC on tuberous and corm vegetables (subgroup 1C), *Brassica* leafy greens (subgroup 5B), dried peas and beans (subgroup 6C), cilantro, and the use of the 1.15% G on tuberous and corm vegetables. FMC is also proposing amending the label for the 2 lb/gal EC to include a non-food/feed use on tobacco. Example labels were provided and the proposed use directions are summarized below in Table 3.

+-----------------+---------+------+--------+--------+-----+--------+
| Table 3.        |         |      |        |        |     |        |
| Summary of      |         |      |        |        |     |        |
| Proposed Use    |         |      |        |        |     |        |
| Directions for  |         |      |        |        |     |        |
| Bifenthrin.     |         |      |        |        |     |        |
+=================+=========+======+========+========+=====+========+
| Application     | Form    | Si   | Max    | Max.   | PHI | Use    |
| Timing, Type    | ulation | ngle | Number | Se     | (Da | Dire   |
| and Equipment   |         | rate | Applic | asonal | ys) | ctions |
|                 | \[EPA   |      | ations | Appli  |     | and    |
|                 | reg.    | (lb  | per    | cation |     | Limit  |
|                 | No.\]   | a    | Season | Rate   |     | ations |
|                 |         | i/A) |        | (lb    |     | ^1^    |
|                 |         |      |        | ai/A)  |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| ### Tu          |         |      |        |        |     |        |
| berous and Corm |         |      |        |        |     |        |
|  Vegetables (Cr |         |      |        |        |     |        |
| op subgroup 1C) |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| In-furrow       | 1.15% G | 0.3  | 1      | 0.5    | 21  | The    |
| application at  |         |      |        |        |     | m      |
| planting        | \[279-  |      |        |        |     | inimum |
|                 | 3244 \] |      |        |        |     | RTI is |
| Ground          |         |      |        |        |     | 21     |
| equipment       |         |      |        |        |     | days.  |
+-----------------+---------+------+--------+--------+-----+--------+
|                 | 2       | 0.3  |        |        |     |        |
|                 | lb/gal  |      |        |        |     |        |
|                 | EC      |      |        |        |     |        |
|                 |         |      |        |        |     |        |
|                 | \[279   |      |        |        |     |        |
|                 | -3069\] |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| Directed foliar | 2       | 0.1  | 2      |        |     |        |
| applications    | lb/gal  |      |        |        |     |        |
| during tuber    | EC      |      |        |        |     |        |
| formation       |         |      |        |        |     |        |
|                 | \[279   |      |        |        |     |        |
| Ground          | -3069\] |      |        |        |     |        |
| equipment       |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| ### *Bra        |         |      |        |        |     |        |
| ssica* leafy Gr |         |      |        |        |     |        |
| eens (subgroup) |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| Post-emergence  | 2       | 0.1  | 4      | 0.4    | 7   | The    |
| broadcast       | lb/gal  |      |        |        |     | m      |
| foliar          | EC      |      |        |        |     | inimum |
| applications    |         |      |        |        |     | RTI is |
|                 | \[279   |      |        |        |     | 7 days |
| Ground or       | -3069\] |      |        |        |     |        |
| aerial          |         |      |        |        |     |        |
| equipment       |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| ### Dried Bean  |         |      |        |        |     |        |
| s (subgroup 6C) |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| Post-emergence  | 2       | 0.1  | 3      | 0.3    | 14  | No     |
| broadcast       | lb/gal  |      |        |        |     | m      |
| foliar          | EC      |      |        |        |     | inimum |
| applications    |         |      |        |        |     | RTI is |
|                 | \[279   |      |        |        |     | spe    |
| Ground or       | -3069\] |      |        |        |     | cified |
| aerial          |         |      |        |        |     |        |
| equipment       |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| **Dried Peas    |         |      |        |        |     |        |
| (subgroup 6C)** |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| Post-emergence  | 2       | 0.1  | 2      | 0.2    | 14  | A      |
| broadcast       | lb/gal  |      |        |        |     | m      |
| foliar          | EC      |      |        |        |     | inimum |
| applications    |         |      |        |        |     | RTI is |
|                 | \[279   |      |        |        |     | not    |
| Ground or       | -3069\] |      |        |        |     | spe    |
| aerial          |         |      |        |        |     | cified |
| equipment       |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| ### Cilan       |         |      |        |        |     |        |
| tro (Coriander) |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| Post-emergence  | 2       | 0.1  | 5      | 0.5    | 3   | The    |
| broadcast       | lb/gal  |      |        |        |     | m      |
| foliar          | EC      |      |        |        |     | inimum |
| applications    |         |      |        |        |     | RTI is |
|                 | \[279   |      |        |        |     | 7      |
| Ground or       | -3069\] |      |        |        |     | days.  |
| aerial          |         |      |        |        |     |        |
| equipment       |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| ### Tobacco     |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| Pre-transplant  | 2       | 0.1  | 1      | NS     | NS  | Apply  |
| soil            | lb/gal  |      |        |        |     | pr     |
| application     | EC      |      |        |        |     | e-tran |
|                 |         |      |        |        |     | splant |
| Ground          | \[279   |      |        |        |     | soil   |
| equipment       | -3069\] |      |        |        |     | appli  |
|                 |         |      |        |        |     | cation |
|                 |         |      |        |        |     | and    |
|                 |         |      |        |        |     | bro    |
|                 |         |      |        |        |     | adcast |
|                 |         |      |        |        |     | foliar |
|                 |         |      |        |        |     | applic |
|                 |         |      |        |        |     | ations |
|                 |         |      |        |        |     | in a   |
|                 |         |      |        |        |     | m      |
|                 |         |      |        |        |     | inimum |
|                 |         |      |        |        |     | of 10  |
|                 |         |      |        |        |     | gal/A, |
|                 |         |      |        |        |     | and    |
|                 |         |      |        |        |     | water  |
|                 |         |      |        |        |     | drench |
|                 |         |      |        |        |     | appli  |
|                 |         |      |        |        |     | cation |
|                 |         |      |        |        |     | in     |
|                 |         |      |        |        |     | 50-200 |
|                 |         |      |        |        |     | gal/A  |
+-----------------+---------+------+--------+--------+-----+--------+
| At transplant   |         | 0.1  | 1      |        | NS  |        |
| water drench    |         |      |        |        |     |        |
| application     |         |      |        |        |     |        |
|                 |         |      |        |        |     |        |
| Ground          |         |      |        |        |     |        |
| equipment       |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+
| Broadcast       |         | 0.05 | NS     |        | NS  |        |
| foliar          |         |      |        |        |     |        |
| applications up |         |      |        |        |     |        |
| to and          |         |      |        |        |     |        |
| including       |         |      |        |        |     |        |
| lay-by          |         |      |        |        |     |        |
|                 |         |      |        |        |     |        |
| Ground          |         |      |        |        |     |        |
| equipment       |         |      |        |        |     |        |
+-----------------+---------+------+--------+--------+-----+--------+

^1^ Crops with bifenthrin tolerances may be rotated at any time, and all
other corps may be rotated 30 days following the final bifenthrin
application.

NS = not specified.

Number range CHAPTER*Conclusions.* The proposed use directions for
tuberous and corm vegetables, leafy *Brassica* greens, dried peas and
beans, and cilantro are adequately supported by the available field
trials on potatoes, mustard greens, dried beans and peas, and cilantro;
however, the use directions for dried beans and peas should be amended
to specify a minimum RTI of 7 days. The available tobacco field trials
will also support the use of the EC formulation on tobacco; however, the
use directions should be amended to specify the maximum number of foliar
applications allowed and the maximum seasonal use rate. The available
tobacco field trails will support use of the 2 lb/gal EC as either a
broadcast pre-plant soil application at up to 0.1 lb ai/A or an
in-furrow water drench application at transplant at up to 0.1 lb ai/A,
followed by a single broadcast foliar application up to lay-by at up to
0.1 lb ai/A, for a maximum seasonal use rate of 0.2 lb ai/A. These data
will also support the use of the 1.15% G formulation to tobacco as a
single broadcast pre-plant soil application at up to 0.1 lb ai/A. **A
revised Section B should be submitted.**

Number range CHAPTER

**860.1300 Nature of the Residue -- Plants.**

**Bifenthrin TRED, Number range CHAPTERS. Levy, 21-AUG-2002; DP#
283808**

45794202.der

Number range CHAPTERThe nature of bifenthrin residues in plants is
adequately understood based on the available metabolism studies on corn,
cotton, and apple. HED previously determined that for purposes of
tolerance expression and risk assessment, the residue of concern in
cotton and apple commodities is bifenthrin *per se* (Memos, M. Flood,
24-DEC-1987 and N. Dodd, 02-JUL-1987). After re-examining the cotton and
apple metabolism data and additional corn metabolism data, the HED
Metabolism Committee (Memo, M. Flood, 23-JUL-1993) reaffirmed that the
residue of concern in plant commodities is bifenthrin *per se*.

In conjunction with the petition for use on tuberous and corm
vegetables, IR-4 has submitted an additional metabolism study on
potatoes reflecting both soil and foliar applications of \[^14^C\]
bifenthrin. The potato study is adequate and the results from the
metabolism study (discussed below) support HED's previous determination
that the residue of concern is bifenthrin *per se.*

Number range CHAPTER

**Potato metabolism.** The metabolism of bifenthrin in potatoes was
examined in two trials using either \[cyclopropyl-1-^14^C\]- or
\[U-phenyl-^14^C\]-labeled bifenthrin (^14^C-CP or ^14^C-PH). Each
^14^C-label was formulated as an EC and applied to potatoes as a single
in-furrow application at 0.3 lb ai/A, followed by two broadcast foliar
applications at 0.1 lb ai/A/application, for a total of 0.5 lb ai/A (1x
rate). The foliar applications were made late in the season during the
vegetative stage, at a RTI of 14 days. Samples of potato tubers and
foliage were collected at 2- and 14-day PHIs.

The levels of radioactivity in foliage and tubers were similar for the
\[^14^C-CP\] and \[^14^C-PH\] labeled samples. Total radioactive
residues (TRR) in foliage were 2.89-3.29 ppm at a 2-day PHI and declined
to 1.94-2.70 ppm by the 14-day PHI. TRR were substantially lower in
tubers (0.020-0.068 ppm) at both sampling intervals, indicating that
translocation of \[^14^C\]bifenthrin from leaves to the tubers was
minimal.

Mature (14-day PHI) samples of tubers and foliage were extracted with
acetonitrile (ACN), releasing 91-96% of the TRR from each matrix.
Solubilized residues were subsequently partitioned into hexane,
ether/ACN, and aqueous fractions. Number range CHAPTERRadioactivity
remaining in the residual solids accounted for 7.5-8.6% TRR in tubers
and 4.3% of the TRR in foliage. With the exception of several minor
metabolites, the ^14^C-residue profiles in tubers and foliage were
similar for the two ^14^C-labels, with identified residues accounting
for 75-81% of the TRR in tubers and 95% of the TRR in foliage. In all
matrices, bifenthrin was the major ^14^C-residue accounting for 73-81 %
of the TRR in tubers and 95% of the TRR in foliage. Minor amounts (≤1.2%
TRR, \<0.001 ppm) of the following metabolites were also tentatively
identified by high-performance liquid chromatography (HPLC) in tubers:
4-OH-bifenthrin, biphenyl alcohol or acid metabolites, a biphenyl
aldehyde metabolite, and TFP acid (see attachment 2 for structures). No
metabolites were detected in foliage. Considering the type of
metabolites detected, the metabolism of bifenthrin in potatoes appears
to involve hydrolytic cleavage of the ester linkage and hydroxylation of
the biphenyl moiety.

**860.1300 Nature of the Residue -- Livestock.**

**Bifenthrin TRED, Number range CHAPTERS. Levy, 21-AUG-2002; DP#
283808**

Adequate ruminant and poultry metabolism studies are available depicting
the metabolism of bifenthrin radiolabeled in either the phenyl or
cyclopropyl ring. Based on these data, the HED Metabolism Committee (M.
Flood, 8/2/93) concluded that the residue of concern in livestock
commodities is bifenthrin *per se.*

**860.1340 Residue Analytical Methods - Plants.**

[]{.mark}

Number range CHAPTERAdequate GC/ECD methods are available for enforcing
bifenthrin tolerances on cottonseed (FMC Method RAN-0140), corn
commodities (FMC Method P-2550), pears (FMC Method P-0757), and pecans
(FMC Method PC-0130); these methods have undergone successful petition
method validation (PMV) trials. The general procedures of these methods
involve extraction of the sample with acetone, partitioning with hexane,
purification of the extract by Florisil column chromatography, and
analysis of the extract by GC/ECD. The LOQ for these methods is 0.05
ppm.

Residues of bifenthrin in samples from the current crop field trials and
processing study were determined using modifications of FMC method
P-2550 M, with variations in extraction solvents and detection methods.
Residues of bifenthrin in/on mustard greens and cilantro (fresh, dried,
seeds) were determined using a GC/ECD method (FMC Report P-2132). For
this method, residues are extracted with hexane, concentrated, and
cleaned up using a Florisil column, then analyzed by GC/ECD. Residues
in/on potato fractions and dried beans and peas were determined using a
GC/MSD method (FMC Report P-3426). For this method, residues are
extracted with acetone, concentrated, and purified by silica-gel SPE.
The residues are then analyzed by GC/MSD, using the m/z 181 ion for
quantitation. Residues in/on green tobacco were determined using a
related GC/MSD method (FMC Report P-3457). For this method, residues are
extracted with acetone/water, partitioned into hexane, and cleaned up
with a SPE column, and analyzed by GC/MSD. For each of the above
methods, the LOQ for bifenthrin is 0.05 ppm, and the reported LOD is
0.01 ppm.

Each of the above methods was validated in conjunction with the field
trials or processing study. For potatoes matrices fortified at 0.05-0.2
ppm, average recoveries were 72-100% with standard deviations of ±7-12%;
for mustard greens fortified at 0.05-6.1 ppm, average recoveries were
73-104%, with standard deviations of ±2-15%; for fresh cilantro and seed
fortified at 0.05-4.9 ppm and dried cilantro fortified at 0.1-20 ppm,
average recoveries were 79-92%, with standard deviations of ±4-15%; and
for tobacco fortified at 0.05 ppm, the average recovery was 110±4%.

*Conclusion.* The available GC/ECD or GC/MSD methods are adequate for
collecting data on bifenthrin residues in/on mustards greens, dried
beans and peas, potato matrices (tubers, chips, wet peel, and flakes),
cilantro leaves (fresh and dried) and seeds, and green tobacco.

**860.1340 Residue Analytical Methods - Livestock.**

Number range CHAPTERSeveral GC/ECD methods are available for enforcing
of tolerances for bifenthrin in cattle tissues and milk (P-1031) and in
poultry tissues (P-1843M) and eggs (RAN-0204M). The general procedures
of these methods involve extraction of the sample with acetone,
purification of the residues by Florisil column chromatography, and
analysis of the residues by GC/ECD. The LOQ for bifenthrin is 0.005 ppm
in eggs, and 0.05 ppm in milk and tissues.

[]{.mark}

Number range CHAPTER**860.1360 Multiresidue Methods (MRM)**

Number range CHAPTERThe Food and Drug Administration (FDA) PESTDATA
database dated 10/99 (PAM Vol. I, Appendix II) indicates that bifenthrin
is completely recovered using MRM Section 303 and that recoveries using
Section 302 are variable. No information pertaining to the recovery of
bifenthrin using Section 304 is available.

[]{.mark}

[]{.mark}

**860.1380 Storage Stability.**

[]{.mark}

**Bifenthrin TRED, Number range CHAPTERS. Levy, 21-AUG-2002; DP#
283808**

Adequate data are available indicating that bifenthrin is stable during
frozen storage (≤-18°C) in a variety of plant matrices. Residues of
bifenthrin are stable during frozen storage for up to: 12 months in corn
flour, meal, oil, and starch; 18 months in/on oranges (whole) and orange
dried pulp, juice, and oil; 24 months in/on cottonseed; 34 months in/on
corn grain; 36 months in/on lettuce, pecans, and potatoes; and 49 months
in/on apple, corn silage, and corn stover.

In the current field trials and potato processing study, the maximum
frozen storage intervals were 2 months for mustard greens, dried peas
and beans, and whole potatoes, ≤1 month for processed potato fractions,
8 months for green tobacco, 22 and 23 months for cilantro leaves, fresh
and dried, respectively, and 17 months for seeds.

*Conclusion.* The available storage stability data are adequate to
support the sample storage intervals and conditions from the current
field trials and potato processing study.

[]{.mark}

[]{.mark}

**860.1480 Meat, Milk, Poultry, and Eggs**

[]{.mark}

**Bifenthrin TRED, Number range CHAPTERS. Levy, 21-AUG-2002; DP#
283808**

[]{.mark}

The maximum theoretical dietary burdens (MTDB) of bifenthrin for
livestock were recently calculated in the Bifenthrin TRED. Based on
established and recommended tolerances, the MTDB was calculated to be
2.7 ppm for beef cattle, 3.3 ppm for dairy cattle, 0.14 ppm for poultry,
and 0.12 ppm for hogs. In the current series of petitions, the only crop
with any regulated livestock feedstuffs is potato (processed potato
waste and culls). As potato waste and culls are not fed to poultry, the
proposed uses will not have any impact on the current tolerances for
poultry commodities.

Using a HED-recommended tolerance of 0.05 ppm for potato (tuber and corm
vegetable), the MTDB was recalculated for cattle and hogs (Table 4). The
inclusion of potato feedstuffs did not increase the MTDB of beef cattle
(2.73 ppm), dairy cattle (3.33 ppm), or hogs (0.12 ppm). Therefore, the
proposed uses will not have any impact on the current milk or livestock
tolerances. []{.mark}

[]{.mark}

  ----------------------------------------------------------------------------
  Table 4.                                                     
  Calculation of                                               
  Maximum Dietary                                              
  Burdens of                                                   
  Livestock for                                                
  bifenthrin                                                   
  Residues.                                                    
  ------------------- ----------- ---------- ----------------- ---------------
  Feed Commodity      \% Dry      \% Diet^1^ Current or        Dietary
                      Matter^1^              Recommended       Contribution
                                             Tolerance (ppm)   (ppm)^2^

  **Beef Cattle**                                              

  Corn, sweet, forage 48          40         3.0               2.5

  Potato, culls       20          35         0.05              0.09

  Cotton, seed        88          25         0.5               0.14

  TOTAL BURDEN                    100                          **2.73**

  **Dairy Cattle**                                             

  Corn, sweet, forage 48          50         3.0               3.13

  Potato, culls       20          25         0.05              0.06

  Cotton, seed        88          25         0.5               0.14

  TOTAL BURDEN                                                 **3.33**

  **Hog**                                                      

  Field corn, Grain   88          45         0.05              0.023

  Cottonseed, Meal    89          15         0.5               0.075

  Potato, culls       20          40         0.05              0.02

  TOTAL BURDEN                    100        \--               **0.12**
  ----------------------------------------------------------------------------

^1^ Table 1 (August 1996).

^2^ Contribution = \[tolerance ÷ %DM (if cattle)\] × % diet.

**860.1500 Crop Field Trials**

**45794203.der1 (potato)**

**45660301.der (mustard greens)**

**45642701/der (beans and peas)**

**46279701.der (cilantro)**

**46045001.der (tobacco)**

IR-4 has submitted crop field trials supporting the use of bifenthrin on
tuberous and corm vegetables (subgroup 1C), leafy *Brassica* vegetables
(subgroup 5B), dried shelled beans and peas (subgroup 6C), and cilantro.
FMC has also submitted data supporting the use of bifenthrin on tobacco.
Number range CHAPTERThe results from these studies are discussed below
and summarized in Table 5.

<table>
<colgroup>
<col style="width: 10%" />
<col style="width: 9%" />
<col style="width: 10%" />
<col style="width: 9%" />
<col style="width: 5%" />
<col style="width: 7%" />
<col style="width: 7%" />
<col style="width: 10%" />
<col style="width: 10%" />
<col style="width: 10%" />
<col style="width: 8%" />
</colgroup>
<thead>
<tr class="header">
<th colspan="11">Table 5. Summary of Residue Data from Field Trials with
Bifenthrin (EC or G).</th>
</tr>
<tr class="odd">
<th rowspan="2">Commodity</th>
<th rowspan="2">Form.</th>
<th rowspan="2"><p>Total Applic. Rate</p>
<p>(lb ai/A)</p></th>
<th rowspan="2"><p>PHI</p>
<p>(days)</p></th>
<th colspan="7">Residue Levels (ppm)<sup>1</sup></th>
</tr>
<tr class="header">
<th>n</th>
<th>Min.</th>
<th>Max.</th>
<th>HAFT<sup>2</sup></th>
<th>Median</th>
<th>Mean</th>
<th>Std. Dev.</th>
</tr>
<tr class="odd">
<th colspan="11"><strong>Potatoes</strong></th>
</tr>
<tr class="header">
<th rowspan="2">Potatoes<sup>3</sup></th>
<th>G + EC</th>
<th>0.5</th>
<th>21</th>
<th>24</th>
<th>&lt;0.05</th>
<th>&lt;0.05</th>
<th>0.05</th>
<th>0.025</th>
<th>0.025</th>
<th>0</th>
</tr>
<tr class="odd">
<th>EC + EC</th>
<th>0.5</th>
<th>21</th>
<th>24</th>
<th>&lt;0.05</th>
<th>&lt;0.05</th>
<th>0.05</th>
<th>0.025</th>
<th>0.025</th>
<th>0</th>
</tr>
<tr class="header">
<th colspan="11"><strong>Mustard Greens</strong></th>
</tr>
<tr class="odd">
<th>Mustard Greens</th>
<th>EC</th>
<th>0.397-0.427</th>
<th>6-7</th>
<th>16</th>
<th>&lt;0.05</th>
<th>2.05</th>
<th>2.01</th>
<th>1.04</th>
<th>1.08</th>
<th>0.71</th>
</tr>
<tr class="header">
<th colspan="11"><strong>Dried Beans and Peas</strong></th>
</tr>
<tr class="odd">
<th>Dried Beans</th>
<th>EC</th>
<th>0.3</th>
<th>13-15</th>
<th>18</th>
<th>&lt;0.05</th>
<th>0.10</th>
<th>0.095</th>
<th>0.025</th>
<th>0.043</th>
<th>0.029</th>
</tr>
<tr class="header">
<th>Dried Peas</th>
<th>EC</th>
<th>0.2</th>
<th>14-15</th>
<th>12</th>
<th>&lt;0.05</th>
<th>&lt;0.05</th>
<th>0.05</th>
<th>0.025</th>
<th>0.025</th>
<th>0</th>
</tr>
<tr class="odd">
<th colspan="11"><strong>Cilantro (Coriander)</strong></th>
</tr>
<tr class="header">
<th>Fresh leaves</th>
<th>EC</th>
<th>0.497-0.508</th>
<th>3</th>
<th>6</th>
<th>1.98</th>
<th>4.83</th>
<th>3.96</th>
<th>2.73</th>
<th>2.97</th>
<th>0.99</th>
</tr>
<tr class="odd">
<th>Dried leaves</th>
<th>EC</th>
<th>0.497</th>
<th>2</th>
<th>2</th>
<th>14.93</th>
<th>16.25</th>
<th>NA</th>
<th>15.60</th>
<th>15.59</th>
<th>0.94</th>
</tr>
<tr class="header">
<th>Seeds</th>
<th>EC</th>
<th>0.518</th>
<th>3</th>
<th>2</th>
<th>3.66</th>
<th>3.69</th>
<th>NA</th>
<th>3.67</th>
<th>3.67</th>
<th>0.03</th>
</tr>
<tr class="odd">
<th colspan="11"><strong>Tobacco</strong></th>
</tr>
</thead>
<tbody>
<tr class="odd">
<td rowspan="4">Green Tobacco<sup>4</sup></td>
<td>EC or G</td>
<td>0.1</td>
<td>85-176</td>
<td>14</td>
<td>&lt;0.05</td>
<td>&lt;0.05</td>
<td>NA</td>
<td>0.025</td>
<td>0.025</td>
<td>NA</td>
</tr>
<tr class="even">
<td>EC</td>
<td>0.1</td>
<td>85-176</td>
<td>14</td>
<td>&lt;0.05</td>
<td>&lt;0.05</td>
<td>NA</td>
<td>0.025</td>
<td>0.025</td>
<td>NA</td>
</tr>
<tr class="odd">
<td>EC</td>
<td>0.15</td>
<td>55-106</td>
<td>14</td>
<td>&lt;0.05</td>
<td>&lt;0.05</td>
<td>NA</td>
<td>0.025</td>
<td>0.025</td>
<td>NA</td>
</tr>
<tr class="even">
<td>EC</td>
<td>0.20-0.30</td>
<td>55-106</td>
<td>14</td>
<td>&lt;0.05</td>
<td>&lt;0.05</td>
<td>NA</td>
<td>0.025</td>
<td>0.025</td>
<td>NA</td>
</tr>
</tbody>
</table>

^1^ The LOQ is 0.05 ppm for all commodities, and the LOD is 0.01 ppm.
For calculation of the median, mean, and standard deviation, ½LOQ was
used for samples with residues \<LOQ.

^2^ HAFT = Highest-Average Field Trial.

^3^ The use rate for potatoes reflects the use of either an EC or G
formulation applied in-furrow at 0.3 lb ai/A in side-by-side trials,
followed by two foliar applications of an EC at 0.1 lb ai/A/application.

^4^ Four application regimes were used on tobacco: (1) a single
pre-transplant, broadcast application (EC or G) at 0.1 lb ai/A; (2) a
single in-furrow or soil drench application (EC) at transplanting at 0.1
lb ai/A; an in-furrow or soil drench application (EC) at 0.1 lb ai/A at
transplanting, followed by a single broadcast foliar application (EC) at
0.05 lb ai/A, for a total of 0.15 lb ai/A/season ; and (4) an in-furrow
or soil drench application (EC) at 0.1 or 0.2 lb ai/A at transplanting,
followed by a single broadcast foliar application (EC) at 0.1 lb ai/A,
for a total of 0.2 or 0.3 lb ai/A/season .

[]{.mark}

**Potatoes:** Twelve potato field trials were conducted during 2001
comparing the use of two bifenthrin formulations. At each trial,
bifenthrin (2 lb/gal EC or 1.15% G) was applied to potatoes as one
in-furrow application at 0.3 lb ai/A followed by two broadcast foliar
applications of the 2 lb/gal EC at 0.1 lb ai/A/application, for a total
of 0.5 lb ai/A/season (1x proposed rate). The in-furrow application was
made prior to planting, and the foliar applications were made late in
the season, approximately 42 and 21 days prior to normal maturity.
Duplicate control and treated samples of potatoes were harvested at
commercial maturity from treatment at each trial site, at approximately
20-21-day PHIs. Samples were stored frozen for up to 1 month, an
interval supported by the available storage stability data.

The GC-MSD method (FMC Report P-3426) used to determine bifenthrin
residues in/on potatoes was adequately validated in conjunction with the
field trial analyses. The validated LOQ was 0.05 ppm, and the LOD was
0.01 ppm.

Regardless of the type of formulation used for the in-furrow application
(G or EC), bifenthrin residues were \<LOQ (\<0.05 ppm) in/on all 48
samples of potatoes harvested \~20-21 DAT following applications at 1x.
The average and HAFT residues in/on potatoes were 0.025 and 0.05 ppm,
respectively. Residue decline information could not be determined from
the two decline trials because of the lack of residues found at any of
the sampling points.

**Mustard Greens:** In eight field trials conducted during 1999,
bifenthrin (2 lb/gal EC) was applied as four broadcast foliar
applications to mustard greens at 0.097-0.110 lb ai/A/application, for a
total of 0.397-0.427 lb ai/A/season (1x the propose rate). Applications
were made during vegetative growth, at RTIs of 6-8 days. Duplicate
control and treated samples of fresh mustard greens were harvested at
commercial maturity from each trial site, at 6-7 day PHIs. Samples were
stored frozen for up to 2 months prior to analysis, an interval
supported by the available storage stability data.

The GC/ECD method (FMC Report P-2132M, modified) used to determine
bifenthrin residues in/on mustard greens was adequately validated in
conjunction with the field trial analyses. The validated LOQ was 0.05
ppm. The LOD was not calculated or estimated.

Bifenthrin residues were 0.05-2.05 ppm in/on 16 samples of mustard
greens harvested at 6-7 day PHIs, following applications at 1x the
proposed rate. The average and HAFT residues in/on mustard greens were
1.04 and 2.01 ppm, respectively. Residue decline data were not provided.

**Dried Beans and Peas:** A total of 15 field trials were conducted
during 2001 on dried beans (9 trials) and peas (6 trials), which are the
representative crops for Crop subgroup 6C. Bifenthrin (2 lb/gal EC) was
applied to dried beans as three broadcast foliar applications at 0.1 lb
ai/A/application, for a total of 0.3 lb ai/A/season (1x proposed rate).
The initial application was made at the 2-6 node stage, the second
application was made at bloom through pod fill, and the final
application was made at early maturity, \~14 days prior to normal
harvest. The RTIs for dried beans were 10-44 days. In the six dried pea
field trials, bifenthrin (2 lb /gal EC) was applied as two broadcast
foliar applications at 0.1 lb ai/A/application, at approximately 21 and
14 days prior to normal maturity, for a total of 0.2 lb ai/A/season (1x
the proposed rate). The RTIs for the dried pea trials were 6-7 days. At
commercial maturity (13-15 day PHIs), a single control and duplicate
treated samples of dried beans or peas were collected from each trial.
To examine residue decline, additional duplicate samples were collected
at 9, 14, 19, and 27 day PHIs from one dried bean trial and at 12, 15,
20, and 27 day PHIs from one dried pea trial. Samples were stored frozen
for up to 2 months, an interval supported by the available storage
stability data.

The GC/MSD method (FMC Report P-3426) used to determine bifenthrin
residues in/on beans and peas was adequately validated in conjunction
with the field trial analyses. The validated LOQ was 0.05 ppm, and the
LOD was 0.01 pm.

Following applications at 1x the proposed rate, residues of bifenthrin
were \<0.01-0.10 ppm in/on 18 samples of dried beans harvested 13-15
DAT, and \<LOQ in/on all 12 samples of dried peas (\<0.01-0.02 ppm)
harvested at 14-15 DAT. The average residues were 0.043 ppm for dried
beans and 0.025 ppm for dried peas. Residue decline could not be
determined for dried beans, as residues in all samples from the decline
trial were \<LOD. However, residues in dried peas, although low (≤0.02
ppm), did show decline at longer post-treatment intervals.

**Cilantro (Coriander):** In four field trials conducted during
2000-2001, bifenthrin (2 lb/gal EC) was applied as five broadcast foliar
applications to cilantro at 0.097-0.106 lb ai/A/application, for a total
of 0.497-0.518 lb ai/A/season (1x proposed rate). Applications were made
beginning at the 1-4 true-leaf stage, at RTIs of 6-7 days. At commercial
maturity, samples of fresh cilantro foliage (3 trials) and seeds (1
trial) were harvested 3 DAT. At one of the trial sites, additional
samples of fresh cilantro were harvested at 2 DAT and dried in ovens for
2 days to yield dried cilantro samples. Duplicate control and treated
samples were collected for analysis from each trial. Samples were stored
frozen for up to 23 months, an interval supported by the available
stability data.

The GC/ECD method used to determine bifenthrin residues in/on cilantro
(FMC Report P-2132M, modified) was adequately validated in conjunction
with the field trial analyses. The validated LOQ was 0.05 ppm.

Following applications at 1x rate, bifenthrin residues were 1.98-4.83
ppm in/on 6 samples of fresh cilantro foliage harvested 3 DAT,
14.93-16.25 ppm in/on 2 dried cilantro samples harvested 2 DAT, and
3.66-3.69 ppm in/on 2 cilantro seed samples harvested 3 DAT. The average
and HAFT residues in/on fresh cilantro were 2.97 and 3.96 ppm,
respectively. Based on average residues in fresh cilantro (2.73 ppm) and
dried cilantro (15.59 ppm) from one trial, the concentration factor for
dried cilantro is 5.7x.

**Tobacco (non-food/feed):** Number range CHAPTERField trials on tobacco
were conducted at three trial sites in VA (2) and GA (1) during 2002,
with four different application regimes being tested at each field site.
The four application regimes included: (i) a single pre-transplant,
broadcast application of either the 2 lb/gal EC or 1.15% G formulation
at 0.1 lb ai/A (Plot 1); (ii) a single in-furrow or soil drench
application of the 2 lb/gal EC at transplanting at 0.1 lb ai/A (Plot 2);
a combination of an in-furrow or soil drench application of the 2 lb/gal
EC at 0.1 lb ai/A at transplanting, followed 1 month later by a single
broadcast foliar application of the 2 lb/gal EC at 0.05 lb ai/A, for a
total of 0.15 lb ai/A/season (Plot 3); and (iv) a combination of an
in-furrow or soil drench application of the 2 lb/gal EC at 0.1 or 0.2 lb
ai/A at transplanting, followed 1 month later by a single broadcast
foliar application of the 2 lb/gal EC at 0.1 lb ai/A, for a total of 0.2
or 0.3 lb ai/A/season (Plot 4).

Number range CHAPTERFor the first VA field trial, tobacco was harvested
three times between 90-176 DAT from Plots 1 and 2, and 57-106 DAT from
Plots 3 and 4. For the GA field trial, tobacco was also harvested three
times between 85-128 DAT from Plots 1 and 2 and 55-98 DAT from Plots 3
and 4. For the second VA field trial, tobacco was harvested only once at
105 or 142 DAT from Plots 1 and 2 and at 72 DAT from Plots 3 and 4. At
each harvest interval, a single control and duplicate treated samples of
green tobacco were harvested from each trial plot.

Residues of bifenthrin in/on green tobacco were determined using a
GC/MSD method (FMC Report P-3457). The method LOQ is 0.05 ppm, and the
LOD is 0.01 ppm. Bifenthrin residues were \<0.05 ppm (\<LOQ) in/on all
green tobacco samples from each application regime at all harvest
intervals.

*Conclusions.* The field trials on potatoes, mustard greens, dried beans
and peas, cilantro, and tobacco are Number range CHAPTERadequate. An
adequate number of trials were conducted reflecting the proposed use
patterns in the appropriate geographic regions, and the appropriate
commodities were collected at the proposed PHIs. Samples were analyzed
using adequate analytical methods, and the sample storage intervals are
supported by the available storage stability data. The available potato
data will support a tolerance of 0.05 ppm on tuberous and corm
vegetables (subgroup 1C), and the mustard green data will support a
tolerance of 3.5 ppm on leafy *Brassica* vegetables (subgroup 5B). The
data on dried beans and peas will support a tolerance of 0.15 ppm on
shelled dried beans and peas, excluding soybean (subgroup 6C). The data
on cilantro (coriander) will support separate tolerances of 5 ppm in/on
coriander leaves and seed. Based on the HAFT residues observed for
coriander leaves (3.96 ppm) and the observed processing factor of 5.7x
for dried leaves, the maximum expected residues in/on dried leaves would
be 22.6 ppm, which will support at tolerance of 25 ppm for dried
coriander leaves.

[]{.mark}

Provided that the use directions on tobacco are clarified with regards
to the number of foliar applications allowed and the maximum seasonal
use rate, the available field trial data will support the use of
bifenthrin on tobacco. As residues in/on all samples of green tobacco
from the tobacco field trails were \<0.1 ppm, no additional data are
required to support this use. []{.mark}

[]{.mark}

[]{.mark}

**860.1520 Processed Food and Feed**

[Number range CHAPTER]{.mark}

45794203.der2 (potato)

[]{.mark}

In a field trial conducted during 2001 in WA, bifenthrin (1.15% G and 2
lb/gal EC) was applied to potatoes as a single in-furrow application at
0.5 lb ai/A, followed by two broadcast foliar applications at 0.5 lb
ai/A, for a total of 1.5 lb ai/A/season (3x rate). The foliar
applications were made during tuber development at 42 and 21 days prior
to normal maturity. Bulk samples of potatoes were harvested at
commercial maturity, at a 21-day PHI, and processed into chips, granules
and wet peel using simulated commercial practices. Prior to analysis,
potato tubers (raw agricultural commodity (RAC)), chips, granules and
peels were stored frozen up to 1 month, an interval supported by the
available storage stability data.

The GC-MSD method (FMC Report P-3426) used to determine bifenthrin
residues in/on potatoes (RAC) and processed potato products was
adequately validated in conjunction with the sample analyses. The
validated LOQ was 0.05 ppm for bifenthrin in/on potatoes and potato
processing products; the LOD was 0.01 ppm.

Following applications totaling 1.5 lb ai/A (3x rate), residues of
bifenthrin were nondetectable (\<0.01 ppm) in/on potatoes (RAC)
harvested at a 21-day PHI, and in processed samples of chips and
granules. Residues in wet peel were detectable at 0.02-0.04 ppm, but
were still below the LOQ. As residues were \<LOD in potatoes, a
processing factor for potato chips and granules could not be calculated,
and the processing factor for wet peel was estimated to be 3x. The
maximum theoretical concentration factor for potatoes is 5x.

Number range CHAPTER*Conclusions*. The available potato processing study
is adequate. Because bifenthrin residues were \<LOQ in all samples from
the potato field trials (46229403.der1) and in potatoes (RAC) and all
processed fractions from the 3x treatment level, HED concludes that
residues of bifenthrin in wet peel are unlikely to exceed the LOQ when
bifenthrin is applied at a 1x rate. Therefore, separate tolerances will
be not required for processed potato fractions.

[]{.mark}

**860.1650 Submittal of Analytical Reference Standards**

The analytical reference standard for bifenthrin has been submitted to
the EPA National Pesticide Standards Repository.

**860.1850/1900 Confined and Field Accumulation in Rotational Crops**

**Bifenthrin TRED, Number range CHAPTERS. Levy, 21-AUG-2002; DP#
283808**

Adequate confined and field rotational crop studies are available. Based
on the confined study, HED has concluded that the residue of concern in
rotational crops is the parent compound only. Based on a maximum
seasonal use rate of 0.5 lb ai/A for annual crops, the confined study
and the available field rotational crop study on wheat also support the
current rotational crop restrictions on the labels. Crops having
bifenthrin tolerances may be replanted at any time, and all other crops
may be replanted 30 days following the last application of bifenthrin.
No rotational crop tolerances are required.

[]{.mark}

[]{.mark}

**860.1550 Proposed Tolerances**

[]{.mark}

HED has concluded that tolerance expression for plant and livestock
commodities should include only parent bifenthrin. Tolerances for
bifenthrin residues are currently established on plant commodities at
levels ranging from 0.05 ppm (LOQ) on various commodities to 10.0 ppm on
dried hop cones \[40 CFR §180.568(a)\]. Number range CHAPTER The
tolerances proposed by the registrants in the current vegetable
petitions are listed below in Table 6, along with HED's recommended
tolerance levels. Number range CHAPTER The appropriate tolerance levels
were calculated using the methodology formulated by the NAFTA
MRL/Tolerance Harmonization Workgroup for calculating
statistically-based pesticide tolerances for plant commodities based on
field trial residue data (Attachment 2). Number range CHAPTER Maximum
likelihood estimation (MLE) techniques were used to supplement the dried
bean dataset. Based on visual inspection of the probability plot, the
lognormality assumption was rejected (HED Science Advisory Council for
Chemistry (ChemSAC) meeting of 3/8/06). The value derived by the
California Method (0.15 ppm) was thus deemed to be appropriate.
**Revised Sections F with the correct tolerance levels and commodity
definitions should be submitted where appropriate.**

The available potato data will support a tolerance of 0.05 ppm on
tuberous and corm vegetables (subgroup 1C), and the mustard green data
will support a tolerance of 3.5 ppm on leafy *Brassica* vegetables
(subgroup 5B). The data on dried beans and peas will support a tolerance
of 0.15 ppm on shelled dried beans and peas, excluding soybean (subgroup
6C). The data on cilantro (coriander) will support separate tolerances
of 5 ppm in/on coriander leaves and seed. Based on the HAFT residues
observed for coriander leaves (3.96 ppm) and the observed processing
factor of 5.7x for dried leaves, the maximum expected residues in/on
dried leaves would be 22.6 ppm, which will support at tolerance of 25
ppm for dried coriander leaves.

[Number range CHAPTER]{.mark}

+----------------------+-----------+------------+----------------------+
| ### T                |           |            |                      |
| able 6. Tolerance Su |           |            |                      |
| mmary for Bifenthrin |           |            |                      |
+----------------------+-----------+------------+----------------------+
| Crop Commodity       | Proposed  | R          | Comments             |
|                      | Tolerance | ecommended |                      |
|                      | (ppm)     | Tolerance  | Number range         |
|                      |           | (ppm)      | CHAPTER(*correct     |
|                      |           |            | commodity            |
|                      |           |            | definition*)         |
+----------------------+-----------+------------+----------------------+
| Tuberous and corm    | 0.1       | 0.05       | *Vegetable, tuberous |
| vegetables, subgroup |           |            | and corm, subgroup   |
| 1C                   |           |            | 1C*                  |
+----------------------+-----------+------------+----------------------+
| *Brassica*, leafy    | 3         | 3.5        |                      |
| greens, subgroup     |           |            |                      |
| 5B^1^                |           |            |                      |
+----------------------+-----------+------------+----------------------+
| Turnip greens^1^     | 3         | 3.5        | *Turnip, greens*     |
+----------------------+-----------+------------+----------------------+
| Pea and bean, dried  | 0.1       | 0.15       | *Pea and bean, dried |
| shelled, except      |           |            | shelled, except      |
| soybean, subgroup    |           |            | soybean, subgroup    |
|                      |           |            | 6C*                  |
+----------------------+-----------+------------+----------------------+
| Cilantro, leaves     | 5.0       | 6.0        | *Coriander, leaves*  |
+----------------------+-----------+------------+----------------------+
| Cilantro, dried      | 30.0      | 25         | *Coriander, dried    |
| leaves               |           |            | leaves*              |
+----------------------+-----------+------------+----------------------+
| Coriander, seed      | 5.0       | 5.0        |                      |
+----------------------+-----------+------------+----------------------+

^1^ Number range CHAPTERTurnip greens will be removed from Crop Group 2:
Leaves of root and tuber vegetables group \[40 CFR 180.41 (2)\], and
will become a member of Crop Group 5: Brassica leafy vegetables \[40 CFR
180.41 (5)\]. It will also be a member of Crop Subgroup 5B: Leafy
*Brassica* greens (Commodity Reviewers Guide, B. Schneider,
14-JUN-2002). Until that time, "turnip, greens" should have a separate
tolerance.

**International Tolerances**

Number range CHAPTERThe Codex Alimentarius Commission has established
maximum residue limits (MRLs) for residues of bifenthrin in/on various
commodities. Codex MRLs are expressed in terms of bifenthrin *per se*,
as are U.S. tolerances. The only established Codex MRL relevant to the
current petitions is for potato at 0.05 mg/kg (See attached
International Residue Limits Status sheet). As the recommended tolerance
of tuberous and corm vegetables is also 0.05 ppm, this tolerance is in
harmony with the Codex MRL for potato. There are no equivalent Canadian
or Mexican MRLs for the tolerances being requested in the current
petition.

**References**

Number range CHAPTERDP Barcode: None

Subject: The Metabolism Committee Meeting Held on July 27, 1993. Plant
and Animal Metabolism of Bifenthrin.

From: M. Flood

To: Metabolism Committee

Dated: 8/2/93

MRID(s): None

DP Barcode: D283808

Subject: Bifenthrin. Residue and Product Chemistry Considerations for
the Tolerance Reassessment Eligibility Decision (TRED).

From: S. Levy

To: T. Myers

Dated: 8/21/02

MRID: None

**Attachments**

Attachment 1. International Residue Limits Status sheet

Attachment 2. Bifenthrin Metabolites from Potato Metabolism Study

Attachment 3. Number range CHAPTERTolerance Assessment Number range
CHAPTERCalculations

RDI: P.V. Shah (3/1/06), RAB1 Chemists (3/1/06)

G.F. Kramer:806T:CM#2:(703)305-5079:7509C:RAB1

Template Version September 2003

Attachment 1.

+----------------+--------------+----------------------+--------------+
| Number range   |              |                      |              |
| CHAPTE         |              |                      |              |
| RINTERNATIONAL |              |                      |              |
| RESIDUE LIMIT  |              |                      |              |
| STATUS         |              |                      |              |
+================+==============+======================+==============+
| Chemical Name: | Common Name: | X Proposed tolerance | Date:        |
| 2-             | Bifenthrin   |                      | 10/23/05     |
| methyl(1,1\'-b |              |  Reevaluated        |              |
| iphenyl)-3-yl) |              | tolerance            |              |
| methyl(1R,     |              |                      |              |
| 3R)-3-((1Z)-2- |              |  Other              |              |
| chloro-3,3,3-t |              |                      |              |
| rifluoro-1-pro |              |                      |              |
| penyl)-2,2-dim |              |                      |              |
| ethylcycloprop |              |                      |              |
| anecarboxylate |              |                      |              |
+----------------+--------------+----------------------+--------------+
| Codex Status   |              | U. S. Tolerances     |              |
|                |              |                      |              |
| (Maximum       |              |                      |              |
| Residue        |              |                      |              |
| Limits)        |              |                      |              |
+----------------+--------------+----------------------+--------------+
|  No Codex     |              | Petition#s: 2E6451,  |              |
| proposal step  |              | 2E6423, 3E6882 and   |              |
| 6 or above     |              | 4E6843.              |              |
|                |              |                      |              |
|  No Codex     |              | DP#s: 310089,        |              |
| proposal step  |              | 310874, 313738,      |              |
| 6 or above for |              | 313817, 313818, and  |              |
| the crops      |              |                      |              |
| requested      |              | 313299               |              |
|                |              |                      |              |
|                |              | Other Identifier:    |              |
+----------------+--------------+----------------------+--------------+
| Residue        |              | Reviewer/Branch: S.  |              |
| definition     |              | Levy                 |              |
| (step 8/CXL):  |              |                      |              |
| Bifenthrin     |              |                      |              |
+----------------+--------------+----------------------+--------------+
|                |              | Proposed Residue     |              |
|                |              | definition:          |              |
|                |              | Bifenthrin           |              |
+----------------+--------------+----------------------+--------------+
| Crop (s)       | MRL (mg/kg)  | Crop(s)              | Tolerance    |
|                |              |                      | (ppm)        |
+----------------+--------------+----------------------+--------------+
| Potato         | 0.05         | Tuberous and corm    | 0.05         |
|                |              | vegetables, subgroup |              |
|                |              | 1C                   |              |
+----------------+--------------+----------------------+--------------+
|                |              | Leafy *Brassica*     | 2.5          |
|                |              | greens, subgroup 5B  |              |
+----------------+--------------+----------------------+--------------+
|                |              | Dried shelled pea    | 0.10         |
|                |              | and bean (except     |              |
|                |              | soybean), subgroup   |              |
|                |              | 6C                   |              |
+----------------+--------------+----------------------+--------------+
|                |              | Coriander, leaves    | 5.0          |
+----------------+--------------+----------------------+--------------+
|                |              | Coriander, leaves,   | 25.0         |
|                |              | dried                |              |
+----------------+--------------+----------------------+--------------+
|                |              | Coriander, seed      | 5.0          |
+----------------+--------------+----------------------+--------------+
| Limits for     |              | Limits for Mexico    |              |
| Canada         |              |                      |              |
+----------------+--------------+----------------------+--------------+
|  No Limits    |              |  No Limits          |              |
|                |              |                      |              |
| X No Limits    |              | X No Limits for the  |              |
| for the crops  |              | crops requested      |              |
| requested      |              |                      |              |
+----------------+--------------+----------------------+--------------+
| Residue        |              | Residue definition:  |              |
| definition: NA |              | Bifenthrin           |              |
+----------------+--------------+----------------------+--------------+
| Crop(s)        | MRL (mg/kg)  | Crop(s)              | MRL (mg/kg)  |
+----------------+--------------+----------------------+--------------+
|                |              |                      |              |
+----------------+--------------+----------------------+--------------+
|                |              |                      |              |
+----------------+--------------+----------------------+--------------+
| Notes/Special  |              |                      |              |
| Instructions:  |              |                      |              |
+----------------+--------------+----------------------+--------------+

Rev. 1998

+----------------+-----------------------+-----------------------------+
| **Attachment   |                       |                             |
| 2. Bifenthrin  |                       |                             |
| Metabolites    |                       |                             |
| from Potato    |                       |                             |
| Metabolism     |                       |                             |
| Study**        |                       |                             |
+================+=======================+=============================+
| Common         | Chemical name         | Chemical structure          |
| name/code      |                       |                             |
|                |                       |                             |
| Figure C.3.1   |                       |                             |
| ID No.         |                       |                             |
+----------------+-----------------------+-----------------------------+
| TFP Acid       | Cis-3-(2-chloro-3, 3, | ![](media/image3.wmf)       |
|                | 3-tri                 |                             |
|                | fluoroprop-1-enyl)-2, |                             |
|                | 2-dimethyl-c          |                             |
|                | yclopropanecarboxylic |                             |
|                | acid                  |                             |
+----------------+-----------------------+-----------------------------+
| Biphenyl       | 2-methylbiph          | ![](media/image4.wmf)       |
| Aldehyde       | enyl-3-carboxaldehyde |                             |
+----------------+-----------------------+-----------------------------+
| Biphenyl Acid  | 2-methyl              | ![](media/image5.wmf)       |
|                | biphenyl-3-carboxylic |                             |
|                | acid                  |                             |
+----------------+-----------------------+-----------------------------+
| 4' Hydroxy     | 4'-hydroxy-2-meth     | ![](media/image6.wmf)       |
| bifenthrin     | ylbiphenyl-3-ylmethyl |                             |
|                | (Z) cis               |                             |
|                | 3-(2-chloro-3, 3,     |                             |
|                | 3-tri                 |                             |
|                | fluoroprop-1-enyl)-2, |                             |
|                | 2-dimethylcy          |                             |
|                | clopropanecarboxylate |                             |
+----------------+-----------------------+-----------------------------+
| Biphenyl       | 2-met                 | ![](media/image7.wmf)       |
| Alcohol        | hylbipheny-3-methanol |                             |
+----------------+-----------------------+-----------------------------+

Attachment 3. Number range CHAPTERTolerance Assessment Number range
CHAPTERCalculations

  ----------------- --------------------- ------------------- --------------
  **Chemical:**     Bifenthrin                                

  **Crop:**         Mustard Greens                            

  **PHI:**          PHI=7                                     

  **App. Rate:**    0.397-0.427 lb                            
                    ai/A/season                               

  **Submitter:**                                              

                    **Residues**          **LN(Residues)**    **Z-scores**

                    1.850                 0.62                0.76

                    1.710                 0.54                0.57

                    2.050                 0.72                1.77

                    1.970                 0.68                1.28

                    1.390                 0.33                0.23

                    1.170                 0.16                0.08

                    0.750                 -0.29               -0.57

                    0.910                 -0.09               -0.08

                    0.050                 -3.00               -1.77

                    0.080                 -2.53               -1.28

                    0.180                 -1.71               -0.99

                    0.190                 -1.66               -0.76

                    1.900                 0.64                0.99

                    1.450                 0.37                0.40

                    0.850                 -0.16               -0.23

                    0.840                 -0.17               -0.40
  ----------------- --------------------- ------------------- --------------

  ----------------- --------------------- ------------------- --------------
  **Chemical:**     Bifenthrin                                

  **Crop:**         Cilantro                                  

  **PHI:**          PHI=3                                     

  **App. Rate:**    0.497-0.518 lb                            
                    ai/A/season                               

  **Submitter:**                                              

                    **Residues**          **LN(Residues)**    **Z-scores**

                    1.980                 0.68                -1.43

                    2.440                 0.89                -0.85

                    2.840                 1.04                -0.15

                    2.610                 0.96                -0.47

                    3.660                 1.30                0.47

                    3.690                 1.31                0.85

                    4.830                 1.57                1.43

                    3.090                 1.13                0.15
  ----------------- --------------------- ------------------- --------------

  ----------------- --------------------- ------------------- --------------
  **Chemical:**     Bifenthrin                                

  **Crop:**         Dried Beans (MLE)                         

  **PHI:**          PHI = 14                                  

  **App. Rate:**    0.3                                       

  **Submitter:**                                              

                    **Residues**          **LN(Residues)**    **Z-scores**

                    0.001170476           -6.75               -1.82

                    0.001982736           -6.22               -1.35

                    0.02                  -3.91               -0.07

                    0.03                  -3.51               0.07

                    0.03                  -3.51               0.21

                    0.03                  -3.51               0.35

                    0.002819934           -5.87               -1.06

                    0.003721372           -5.59               -0.85

                    0.004710501           -5.36               -0.66

                    0.005808347           -5.15               -0.50

                    0.1                   -2.30               1.35

                    0.09                  -2.41               1.06

                    0.07                  -2.66               0.66

                    0.1                   -2.30               1.82

                    0.07                  -2.66               0.85

                    0.05                  -3.00               0.50

                    0.007037443           -4.96               -0.35

                    0.00842402            -4.78               -0.21
  ----------------- --------------------- ------------------- --------------