Document ID: EPA-HQ-OPP-2009-0013-0006
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2009-12-18T05:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

OFFICE OF           

PREVENTION, PESTICIDES

AND TOXIC SUBSTANCES

MEMORANDUM

	Date:	1/31/2009		

	Subject:	Dinotefuran.  IR-4 Petition for the Establishment of
Tolerances for Residues of Dinotefuran in/on Brassica, Leafy Greens,
Subgroup 5B and Turnip Greens.

		           							8

PC Code:  	044312	DP Barcode:   	358024

Decision No.: 	400299	Registration No.: 	EPA Reg. Nos. 33657-17,
33657-38, .59639-135

Petition No.: 	8E7433	Regulatory Action: 	Tolerance Exemption/
Registration

Risk Assessment Type: 	Single chemical aggregate	Case No.: 	NA

TXR No.: 	NA	CAS No.: 	165252-70-0

MRID No.: 	475454-01

	40 CFR:	180.603

From:	Amelia M. Acierto, Chemist

Risk Assessment Branch 3

Health Effects Division (7509P)

Through:	Stephen Funk, Senior Scientist

Risk Assessment Branch 3

	                    Health Effects Division (7509P)

	To:	Daniel Rosenblatt , RM Team #05

        Insecticide Branch

                    Registration Division (7505P)

Executive Summary

The Interregional Research Project No. 4 (IR-4), on behalf of the
Agricultural Experiment Stations of Florida, California and Oklahoma,
has submitted a petition proposing the establishment of tolerances for
residues of the insecticide dinotefuran (RS)
-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl) in/on the following raw
agricultural commodities (RACs):

	Brassica, leafy greens, subgroup 5B	17 ppm

	Turnip, greens	17 ppm

In conjunction with this petition, IR-4 requests to register three
soluble granular end-use products, Dinotefuran 20SG (EPA Reg. No.
33657-17), Starkle 70SG (EPA Reg. No. 33657-38), and Dinotefuran 70SG
(EPA Reg. No. 59639-135).  The products are proposed for use on leafy
Brassica greens subgroup 5B and turnip greens as two foliar applications
at up to 0.141 lb ai/application with a maximum seasonal rate of 0.268
lb ai/A.  The petitioner has proposed a preharvest interval (PHI) of 1
day, and retreatment intervals (RTIs) of 6-7 days.  The insecticide may
be applied in a tank mix and/or alternated with commonly used
insecticides to comply with local integrated pest manqgement (IPM) and
resistance management programs.  Foliar application may be accomplished
with aerial or ground equipment with adequate water for uniform
coverage: 3-10 gals/A by air or 20-40 gals/A by ground.

Tolerances have been established under 40 CFR §180.603(a) for the
combined residues of dinotefuran and its metabolites DN
[1-methyl-3-(tetrahydro-3-furylmethyl)guanidine], and UF
[1-methyl-3-(tetrahydro-3-furylmethyl)-urea], expressed as dinotefuran
in/on Brassica, head and stem, subgroup 5A at 1.4 ppm,  cotton,
undelinted seed at 0.4 ppm, cotton, gin by-products at 8.0 ppm, grape at
0.9 ppm, grape, raisin at 2.5 ppm, potato at 0.05 ppm, potato chips at
0.1 ppm , potato, granules/flakes at 0.15 ppm, tomato paste at 1.0 ppm, 
vegetable, fruiting, group 8 at 0.7 ppm, vegetable, cucurbit, group 9 at
0.5 ppm, and vegetable, leafy except Brassica, group 4 at 5.0 ppm. 
Tolerances have also been established under 40 CFR §180.603(a) for
dinotefuran in fat, meat and meat by products of cattle, goat, hog,
horse, and sheep and in milk at 0.05 ppm.

The nature of the residues in plants is adequately understood for the
purpose of this petition, based on previously submitted metabolism
studies with rape, potato, rice, apple, and lettuce.  The residues of
concern in plants for tolerance enforcement are parent, DN and UF, and
for risk assessment are parent, DN, UF, and PHP
[6-hydroxy-5-(2-hydroxyethyl)-1-methyl-1,3-diazinane-2-lidene-N-nitroami
ne].  For ruminants and poultry, the residues of concern for the
tolerance are primarily dinotefuran, and for risk assessment are parent,
UF and FNG in ruminants along with dinotefuran and FNG in poultry (MARC
report, DP#293759, L. Cheng, 01/20/2004).

Three analytical  methods are currently available for tolerance
enforcement and data collection, including an LC/MS/MS method for the
determination of residues of parent, DN and UF in plants (DP#331831,
P.Savoia, 4/17/2007).  A similar LC/MS/MS method developed by Wildlife
International, Ltd. (Project No. 236C-113), entitled “Laboratory
Validation of Method(s) for the Analysis of MTI-446 and its metabolites
DN and UF in Multiple Crop Substrates” was proposed to quantitate the
residues in leafy Brassica greens and turnip greens.  The lowest level
of method validation (LLMV) for dinotefuran and its metabolites (DN and
UF) was reported as 0.01 ppm.  The calculated limit of quantitation
(LOQ) was 0.01 based on recoveries of samples fortified at the LLMV. 
The limit of detection (LOD) was 0.0027 ppm for dinotefuran and 0.0036
ppm for both DN and UF.

 

Adequate field trial data are available for leafy Brassica greens,
subgroup 5B (mustard greens as representative crop).  An adequate number
of geographically representative field trials were conducted at 1.3x the
proposed maximum seasonal rate.  The crop field trial data are supported
by adequate storage stability data.  The decline data show that the
residues of dinotefuran and its metabolites decrease in mustard greens
with increasing sampling interval.

 

The available field trial data indicate that the proposed tolerance for
leafy Brassica greens, subgroup 5B is too high; a lower tolerance of 15
ppm is needed based on data generated from 8 of the 9 crop field trials
that received the proposed number of foliar treatments.  Data from the
9th field trial was not included since 8 field trials are adequate to
meet the requirement (Guideline 1500), and, as noted by the petitioner,
the data from the field that received an extra treatment resulted in
artificially high residues.

  

The available data for mustard greens are adequate to support the
proposed tolerance for turnip greens.  HED has concluded that turnip
greens will be moved from the leaves of root and tuber vegetables crop
group (group 2) to the Brassica leafy vegetables crop group 5, subgroup
5B: (Memorandum,  B. Schneider, 6/14/2002).  Until the regulations have
been finalized in the Federal Register, a separate tolerance is needed
for turnip greens, at the same level as the leafy Brassica greens
tolerance, 15 ppm.

There are currently no established Codex, Mexican, or Canadian MRLs for
dinotefuran.  Therefore, no compatibility questions exist with respect
to Codex.

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

HED has examined the residue chemistry database for dinotefuran. 
Pending submission of a revised Section F to reflect the recommended
tolerance level and revised Section B labels for the end-use products to
reflect the appropriate maximum total in ounces corresponding to the
stated limit in lbs ai/A/season, there are no residue chemistry issues
that would preclude granting tolerances and registration for the
requested use of dinotefuran as stated below.

Provided the forthcoming Human Health Risk Assessment does not identify
any risk concerns,  HED recommends establishment of tolerances as
follows:

	Tolerances to be established under 40 CFR 180.603(a):

		Brassica, leafy greens, subgroup 5B …………….15 ppm

		Turnip greens …………………………………….15 ppm

Deficiencies

860.1200   Directions for Use

The application rate for the 20% formulation must be revised to reflect
the application rate in oz/A.  This corresponds to 7 - 10.5 oz/A.  

The maximum single application rate in lb ai/A must be the same for all
the 3 formulations (i.e., 0.088 - 0.134 lb ai/A).

The maximum seasonal use rates for mustard greens for all labels must be
revised to reflect the maximum proposed seasonal use rate.  This
corresponds to 0.262 lb ai/A for all formulations. 

The label directions for all three formulations are identical, including
the additional directions for “foliar application”  with the
restriction not to apply more than a total of 6 oz of Dinotefuran (0.268
lb ai) per acre per season.   Since the 20 SG formulation ncontains only
20% active ingredient, 6 oz would not be sufficient to provide the
required seasonal rate.  The statement that pertains to the 20 SG
formulation should be corrected.

  

860.1550  Proposed Tolerances

A revised Section F is required to reflect the recommended tolerance
level of 15 ppm.  

Background

Dinotefuran is a Group 4A insecticide belonging to the nitroguanidine
class of chemicals used for the control of sucking and chewing insects
in a variety of plants.  The chemical structure and nomenclature of
dinotefuran and its metabolites DN and UF are summarized in Table 1, and
the physicochemical properties of the technical grade of dinotefuran are
summarized in Table 2.  

Table 1.	Test Compound Nomenclature.

Compound	Chemical Structure

 

Common name	Dinotefuran

Company experimental name	MTI-446

IUPAC name	(RS)-1-Methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine

CAS name	Guanidine,
N-methyl-N’,-nitro-N”-[tetrahydro-3-furanyl)-methyl]-

CAS #	165252-70-0

End-Use Product	Dinotefuran 20SG, EPA Reg No. 33657-17,  Starkle 70SG,
EPA Reg No. 33657-38, Dinotefuran 70SG, EPA Reg. No. 59639-135..

Compound	Chemical Structure

 

Common name	DN

IUPAC name	1-Methyl-3-(tetrahydro-3-furylmethyl)guanidine

Compound	Chemical Structure

 

Common name	UF

IUPAC name	1-Methyl-3-(tetrahydro-3-furylmethyl-urea

€max: Molar

Absorbance Coefficient	45639702

	Acidic	1.0469	12,600

	1.0180	12,300

Neutral	1.3017	12,500

	1.2668	12,300

Basic	0.8869	10,700

	0.9662	11,700

	

850.1200  Directions for Use

IR-4 submitted proposed labels for three soluble granular end-use
products to be used on leafy Brassica greens subgroup 5B and turnip
greens: Dinotefuran 20 SG (EPA Reg. No. 33657-17), Starkle 70 SG (EPA
Reg. No. 33657-38) and Dinotefuran 70 SG (EPA Reg. No. 59639-135). 

 

The proposed use directions for dinotefuran are presented in Table 3. 

 Table  3.		Summary of Directions for Use of Dinotefuran.

Application Timing 	Product [EPA Reg. No.]	Applic Rate 

oz/A

(lb ai/A)	Max. No. Applic. per Season	RTI

(days)	Max. Seasonal Applic. Rate

(lb ai/A)	PHI

(days)	Use Directions and other Limitations

 Leafy Brassica greens subgroup 5B: Brocolli raab, cabbage, Chinese
cabbage (Bok choy), collards, kale, mizuna, mustard greens, mustard
spinach, rape greens and turnip greens.

Foliar application with air or ground equipment.

For best results time application before a damaging population becomes
established.	Dinotefuran 20 SG

[33657-17]

	7 – 10.5 oz/A

(0.088 – 0.131 lb ai/A) 

	2	7	0.262	1	•Higher water volumes provide improved insect control.
Apply in adequate water for uniform coverage (3 -10 gals/A by air or
20-40 gals/A by ground).

•Begin applications when first pest activity is noticed or when
insects reach threshold levels per State and County Extensions Service
recommendations. Repeat as needed to maintain control, but not more than
every 7 days.  For best results, time application before a damaging
population becomes established.

•Under severe pest pressure, use the higher recommended rates.

•Do not apply to vegetables grown for seed.

•The rate applied affects the length of control.  Use the high rate
where infestations occur later in crop development or where pest
pressure is continuous.

•Dinotefuran (Dinotefuran 20SG, Sparkle 70SG or Dinotefuran 70SG) may
be mixed and/or alternated with commonly used insecticides to comply
with local IPM and resistance management programs.

	Sparkle

70 SG

[33657-38]	2 – 3 oz/A

(0.088 – 0.131 lb ai/A)

Dinotefuran 70SG

[59639-135]	2 – 3 oz/A

(0.088 – 0.131 lb ai/A)

	Foliar Application

Apply with air or ground equipment in adequate water for uniform
coverage (3 to 10 gals.A by air or 20-40 gals/A by ground.

Do not apply DINOTEFURAN within one (1) day of harvest.

Foliar Application

•Apply with air or ground equipmentin adequate water for uniform
coverage (3 – 10 gals/A by air or 20 gal?A by ground

• Do not allow DINOTEFURAN 20SG within one (1) day of harvest. 

Do not apply more than a total of 6 oz of DINOTEFURAN 20 SG, Sparkle
70SG or Dinotefuran 70SG  (0.268 lb ai) per acre per season.

Conclusions:  The submitted labels (Dinotefuran 20SG, Sparkle 70SG and
Dinotefuran 70SG end-use products) are adequate to allow an evaluation
of the residue data relative to the proposed use.  The application rate
for the 20% formulation must be revised to reflect the application rate
in oz/A.  This corresponds to 7 - 10.5 oz/A.  The rate in lb ai/A must
be the same for all the 3 formulations (i.e., 0.088 - 0.131 lb ai/A).  
The maximum seasonal use rates for mustard greens must be revised to
reflect the total maximum number of applications at the maximum proposed
use rate.  This corresponds to 0.262 lb ai/A for all formulations.   

The label directions for all three formulations are identical, including
the additional directions for “foliar applications” with the
restriction not to apply more than a total of 6 oz of Dinotefuran (0.268
lb ai) per acre per season.   Since the 20 SG formulation contains only
20% active ingredient, 6 oz would not be sufficient to provide the
required seasonal rate.  Therefore, the statement that pertains to the
20 SG formulation should be corrected.

860.1300  Nature of the Residues – Plants/Livestock

The nature of the residues in plants is adequately understood for the
purpose of this petition, based on previously submitted metabolism
studies with rape, potato, rice, apple, and lettuce.  The main metabolic
reactions in plants are the hydrolysis of the nitroimino moiety of
dinotefuran, loss of the nitro group, intramolecular ring formation, as
well as tetrahydrofuran ring hydroxylation and ring opening.  
Dinotefuran metabolism in livestock was concluded to be similar to the
progression found in plants.  The residues of concern in plants for
tolerance enforcement are parent, DN and UF, and for risk assessment are
parent, DN, UF, and PHP
[6-hydroxy-5-(2-hydroxyethyl)-1-methyl-1,3-diazinane-2-lidene-N-nitroami
ne.  For ruminants and poultry, the residue of concern for the tolerance
expression is primarily dinotefuran.  For risk assessment, the residues
of concern in ruminants are parent, UF and FNG, and the residues of
concern in poultry are dinotefuran and FNG (MARC report, D293759, L.
Cheng, 01/20/2004).

860.1340   Residue Analytical Methods

 

Three methods, including a LC/MS/MS method, are available for
enforcement of tolerances of dinotefuran and metabolites DN and UF. 
ACB/BEAD found the methods to be adequate (DP#331831, P.Savoia,
4/17/2007).  A similar LC/MS/MS method developed by Wildlife
International, Ltd. (Project No. 236C-113), entitled “Laboratory
Validation of Method(s) for the Analysis of MTI-446 and its metabolites
DN and UF in Multiple Crop Substrates”, was proposed to quantitate
residues in mustard greens. The lowest level of method validation (LLMV)
was reported as 0.01 ppm for dinotefuran and metabolites DN and UF.  The
calculated LOQ based on recoveries of samples fortified at the LLMV was
0.0027 ppm for dinotefuran and 0.011 ppm for DN and UF.

   

Briefly, frozen samples were chopped in a Hobart Food Chopper with dry
ice and returned to the freezer to allow the dry ice to sublime
completely.  Twenty-five gram samples were weighed, extracted by
blending and agitation with acetonitrile/water (80:20 v/v/) and
concentrated hydrochloric acid, followed by vacuum filtration and
partitioning with hexane.  The organic phase was discarded.  The aqueous
phase was evaporated to remove any remaining organic solvent and then
adjusted to pH 8 with 0.5M sodium carbonate-sodium bicarbonate buffer. 
The volume of the extract was brought to 100 ml and was cleaned-up prior
to analyses as follows:  (a) For dinotefuran and UF  clean-up, a 40 ml
aliquot was transferred to a 50 ml Erlenmeyer flask containing 15 g
sodium chloride, brought to volume with NANO pure water and agitated for
60 minutes.  A 3 ml aliquot of the mixture was put unto Extrelute QE
column, allowed to absorb for 60 minutes, eluted with 170 ml ethyl
acetate and evaporated to dryness.  The residue was redissolved in 0.1N
HCL and filtered through 0.45 µm Whatman Mini-UniPrep PTFE filter for
LC/MS/MS analysis; (b) For DN clean-up, 40 ml aliquot was mixed well
with 5 ml each of 0.5 M Na2CO3-NaHCO3  buffer and NANO pure water.  A 5
ml aliquot was then loaded to CBA column (previously conditioned with 3
ml methanol followed by 4 ml of 0.5M Na2CO3-NaHCO3 buffer).  The column
was rinsed in sequence with 10 ml water, 6 ml methanol and 2.5 ml 0.1N
HCL.  DN was eluted from the column with 5 ml of 0.1 N HCL and filtered
through 0.45 µm Whatman Mini-UniPrep PTFE filter for LC/MS/MS analysis.

All final sample extracts were stored at -4o to 14oC until analyzed.  

The method was validated using untreated mustard greens fortified
separately with dinotefuran, DN and UF from 0.01, 0.1, 1.0 and10.0 ppm
before the analyses of the crop field samples.  The mean recoveries from
the method validation were 87- 95% (n=15) for dinotefuran, 77- 93%
(n=14) for DN, and 93-99% (n=15) for UF.  In addition, each treated crop
field sample was analyzed concurrently with control samples fortified
separately with dinotefuran, and metabolites, DN and UF at 0.01, 0.1,
and 1.0 ppm.  A summary of the concurrent recoveries for dinotefuran,
DN, and UF were reported in DER 47545401.

 

Conclusions.  The method was adequately validated prior to and in
conjunction with the analysis of field samples.  Based on the method
validation data and concurrent recovery data, the submitted LC/MS/MS
method for leafy Brassica greens is adequate for enforcement and
collection purposes. 

860.1380 Storage Stability

IR-4 conducted concurrent storage stability studies with mustard greens.
 Untreated samples were fortified separately at a nominal fortification
level of 0.1 ppm for each analyte (dinotefuran, DN and UF).  Samples
were placed in frozen storage at <-40 to -1oC and analyzed after 637
days.

The maximum storage interval from harvest to analysis of the mustard
greens crop field trial was 602 days.  The storage stability data
indicate that residues of dinotefuran and its metabolites are stable up
to 637 days.  The concurrent storage stability studies adequately
covered the storage durations of samples from the mustard greens field
trials which were stored frozen between 436 and 602 days.  The storage
durations and conditions of samples from the crop field trials submitted
to support this petition are presented in Table 4.  

TABLE 4.	Summary of Storage Conditions.  

Matrix 	Analyte	Storage Temperature

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

 (days)

Mustard Greens	Dinotefuran

UF

DN	<- 40 to -1	436 - 602	Dinotefuran is stable for up to 637 days with
recoveries of 90-98% for dinotefuran, 78-102% for UF, and 80-98% for
DN.*

*Three storage study samples fortified at 0.1 ppm with each analyte were
extracted after 637 days of frozen storage.  Concurrent recoveries were
96% for dinotefuran and UF, and106% for DN.  No 0-time was reported.

Conclusion:  The storage stability data in/on mustard greens are
adequate to demonstrate that residues of dinotefuran, DN and UF are
stable under frozen storage and support the storage intervals and
durations of samples of mustard greens from the crop field trials.   No
correction for decline during storage is necessary. 

860.1460  Food Handling

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

860.1480  Meat Milk, Poultry, and Eggs

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

860.1500  Crop Field Trials

In support of the proposed use on crop subgroup 5B, IR-4 has submitted
field trial data for dinotefuran on mustard greens.  Nine field trials
were conducted during the 2003 growing season in the United States
encompassing Regions 2, 3, 4, 5, 6, and 10.  At each test location,
untreated and treated plots were provided.  The treated plots received
two foliar applications of dinotefuran formulated as a 20% soluble
granule.  Each application was made at a rate of 0.179 lb ai/A for a
total seasonal rate of 0.36 lb ai/A (~1.3x the proposed rate) and the
retreatment interval was 7 ± 1 days.  No adjuvant was added to the
spray mixture.  At each trial location, untreated and treated raw
agricultural commodity (RAC) samples were harvested 1 day following the
last test substance application.  At one of the test sites, untreated
and treated RAC samples were harvested at 0, 1, 7, and 14 days after the
last application to determine residue decline.

Samples of mustard greens were analyzed for residues of dinotefuran
(parent) and its metabolites DN and UF using an LC/MS/MS method
developed by Wildlife International, Ltd.  The method was adequate for
data collection based on acceptable method validation and concurrent
method recoveries.    

RAC samples were stored frozen prior to analysis. The maximum storage
interval from harvest to analysis was 602 days.  A storage stability
study demonstrated that residues of dinotefuran, DN, and UF are stable
in/on mustard greens stored up to 637 days at <-40 to -1oC; therefore,
adequate storage stability data are available to support the storage
conditions and intervals of samples from the mustard greens field
trials. 

 

The maximum residues in/on mustard greens harvested 1 day after the last
of two applications of the 20% SG formulation at a total rate of 0.35 to
0.36 lb ai/A were 6.5 ppm for dinotefuran (parent), 0.77 ppm for DN and
1.9 for UF.  The maximum combined residues of dinotefuran, DN and UF
from the field trials was 7.8 ppm.  The highest residue from the MD
field trial that received  1 extra treatment was 10.5 ppm.  The results
from these field trials are summarized in Table 5.  

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

Commodity	Total Applic. Rate,

lb a.i./A

(kg a.i./ha)	

PHI (days)	Residue Levels (ppm)

	

n	

Min.	

Max.	

HAFT*	

Median

(STMdR)	

Mean

(STMR)	

Std. Dev.

DINATEFURAN

Mustard greens	

0.268

(1.46)	1	16	0.784	5.79	2.77	4.38	3.74	1.7

DN

Mustard greens	

0.268

(1.46)	

1	

16	0.504	1.90	1.73	0.95	1.22	1.0

UF

Mustard greens	

0.268

(1.46)	

1	

16	0.071	0.774	0.734	0.20	0.27	0..2

*HAFT = Highest average field trial.

Conclusions:  The submitted residue data are adequate to fulfill data
requirements for the establishment of tolerances of dinotefuran in/on
mustard greens.  The submitted field trial data reflect the use of two
foliar applications of the 20% SG formulation at total rates of 0.35 to
0.36 lb ai/A on mustard greens grown in the United States with 1-day
PHI.  An acceptable method was used for quantitation of residues on
mustard greens.  The submitted storage stability data indicate that
residues of dinotefuran, DN, and UF are stable in/on mustard greens
stored frozen for up to 637 days at <-40 to -1oC.  The available data
support the storage intervals of samples from the mustard greens field
trials. The residue decline studies show that the residue of dinotefuran
and its metabolites decline with increasing harvest intervals.  

HED has concluded that turnip greens will be moved to the Brassica leafy
greens subgroup 5B.  Therefore, crop field trial data for mustard greens
(the representative commodity of leafy Brassica greens subgroup 5B) are
sufficient to support the proposed use on turnip greens.  Until the
regulation has been finalized in the Federal Register, a separate
tolerance must be established for turnip greens at the same level as the
leafy Brassica greens tolerance.

The locations of the mustard green field trials are in accordance with
OPPTS Guideline 860.1500 to support a tolerance for the leafy Brassica
greens subgroup 5B and turnip greens except that one field trial in
Region 2 had 3 foliar applications instead of the proposed 2
applications.  The sample from that trial had higher residues as a
result of the extra treatment.  Therefore, the data from that field
trial was not included in the tolerance setting for mustard greens. 
However, the remaining number of field trials (8) is adequate.  An
additional field trial in Region 2 will not be required. 

860.1520   Processed Food and Feed

No processing data were submitted with this petition and none are
required since there are no processed food/feed items associated with
Brassica, leafy greens, Subgroup 5B and turnip greens.

860.1850   Confined Accumulation in Rotational Crops

The petitioner did not submit any study under this guideline.  The
Agency has previously concluded that a confined rotational crop study
with dinotefuran reflecting a 120-day plantback interval for rotated
crops is adequate.  However, if the petitioner wishes to support a
plantback interval less than 120 days, then, a new confined rotational
crop study reflecting a 1x application rate will be required  (D290191,
L. Cheng, 11/23/2004).

860.1900. Field Accumulation in Rotational Crops

The petitioner did not submit any field rotational crop data.   The
Agency has previously  concluded that based on the available confined
rotational crop data, a 120-day plantback interval is needed for all
rotational crops other than cotton, leafy vegetables, fruiting
vegetables, cucurbits, potatoes, and head and stem Brassica (D290191, L.
Cheng, 11/23/2004).

860.1550  Proposed Tolerances

Adequate field trial data are available to support this petition. 
Results indicate that the proposed tolerance (17 ppm) for leafy Brassica
greens subgroup 5B is too high based on the data generated from the crop
field trials after 2 foliar treatments of dinotefuran and a 1-day PHI. 
HED recommends revision of Section F to reflect a tolerane level of 15
ppm for leafy Brassica greens subgroup 5B.  

There are currently no established Codex, Canadian, or Mexican MRLs for
dinotefuran.  An International Residue Limit Status is attached to this
review.

HED has concluded that turnip greens will be moved from the leaves of
the root and tuber vegetables crop group (group 2) to the Brassica leafy
vegetables crop group 5, subgroup 5B: (Memorandum,  B. Schneider,
6/14/2002).  Until the regulations have been finalized in the Federal
Register, a separate tolerance is needed for turnip greens, at the same
level as the leafy Brassica greens tolerance, 15 ppm.  The tolerance
expression is appropriate.  The tolerance calculation based on the 8
crop field trials is presented in Appendix 1.

A summary of the recommended tolerances for the current petition is
presented in Table 6.

 

Table 6.  Tolerance Summary for Dinotefuran

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

Tolerances for combined residues of Dinotefuran [(RS)
-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine] and metabolites
DN [1-methyl-3-(tetrahydro-3-furylmethyl)guanidine], and UF
[1-methyl-3-(tetrahydro-3-furylmethyl)-urea)]

              [40 CFR 180.603(a)

Brassica, leafy greens, subgroup 5B	17	--	15

	Turnip, greens	17	--	15

	

E.	REFERENCES

DP Barcode:	None

Subject:	The reviewers guide and summary of HED ChemSAC approvals for 		
	amending commodity definitions [40 CFR 180.1(h)] and crop 				
group/subgroups [40 CFR 180.41].

From:		B. Schneider

To:		H. Jamerson

Date:		6/14/2002

MRID:		None 

DP Barcodes:	290191, 297889, and 304955

Subject:	Dinotefuran: Petition for the Establishment of Permanent
Tolerances 				on Cotton (PP#2F6427), Fruiting Vegetables, Cucurbits,
Head & Stem 				Brassica Vegetables, Grapes, Potato, Meat, Milk, and
Meat byproducts 				(PP#3F6566).  Summary of Analytical Chemistry and
Residue Data. 

From:		L. Cheng

To:		R. Kumar and M. Laws

Date:		11/23/2004

MRIDs:	45639821, 45654202, 45891601, 45891602, 45891603, 45891604, 			
45891605, 45891606, 45891607, 45891608, 45891609, 45891613, 			
45891614, 45891618, 45891619, 45915401, 46132901, 46270901

DP Barcode:	285648

Subject:	Dinotefuran: (PP#2F06427) Petition for the Establishment of 			
	Permanent Tolerances for Use on Leafy Vegetable (except Brassica).  			
Summary of Analytical Chemistry and residue Data.

From:		L. Cheng

To:		R. Kumar and M. Laws

Date:		02/26/2004

MRIDs:	45639735, 45639801, 45639802, 45639803, 45639804, 45639805, 			
45639806, 45639807, 45639815, 45639816, 45639817, 45639819, 				45639822

DP Barcode:	320972

Subject:	Dinotefuran:Valent’s Request to Amend the Product Label for 	
			Dinotefuran 20 SG (EPA Reg. No. 33657-17) to Increase Application 			
Rates on Potatoes, Cucurbits, Brassica Vegetables, 	Fruiting Vegetables,
				Leafy Vegetables, and Grapes.

From:		N. Dodd

To:		R. Kumar and M. Laws

Date:		09/13/2006

MRIDs:	None

DP Barcode:	331831

Subject:	Dinotefuran: (PP#3F06566) Petition for the Establishment of 			
	Permanent Tolerances on Fruiting Vegetables, Cucurbit, Head & Stem 			
Brassica Vegetables.  Revision to Include Cherry Tomatoes.  					Summary
of Analytical Chemistry and Residue Data.

From:		P. Savoia

To:		R. Kumar

Date:		04/17/2007

MRIDs:	46895901

F.	DOCUMENT TRACKING

Petition Number: 8E7433

DP Barcode: 358024

PC Code: 044312

  SEQ CHAPTER \h \r 1 Attachments:  

International Residue Limit Status sheet

Appendix I - Tolerance Assessment Calculations

Template Version September 2005

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name: (RS)
-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine	Common Name:

Dinotefuran	X Proposed tolerance

   Reevaluated tolerance

   Other	Date:  01/29/2009

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

(No Codex proposal step 6 or above

⁯Codex proposal step 6 or above for the crops requested	Petition
Number:  8E7433

DP#:  358024

Other Identifier:  Decision #400299

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

	Residue definition: Dinotefuran  (RS)
-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine and its
metabolites DN, 1-methyl-3-(tetrahydro-3-furylmethyl)guanidine, and UF,
1-methyl-3-(tetrahydro-3-furylmethyl)-urea) expressed as dinotefuran 
SEQ CHAPTER \h \r 1   SEQ CHAPTER \h \r 1 

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

Brassica, leafy greens, subgroup 5B	15

Turnip, greens	15

Limits for Canada	Limits for Mexico

  ( No Limits

   No Limits for the crops requested	  ( No Limits

   No Limits for the crops requested

Residue definition:  N/A 	Residue definition:  N/A

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

	Notes/Special Instructions: S.Funk, 01/29/2009

Appendix I.  Tolerance Assessment Calculations.

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

Leafy Brassica greens, subgroup 5B

The dataset used to establish a tolerance for dinotefuran on the leafy
Brassica greens subgroup 5B consisted of field trial data for the
representative crop, mustard greens, following 2 foliar applications of
the 20% SG formulation at a seasonal rate of 0.35 to 0.36 lb ai/A with a
1-day PHI.  As specified by the SOP, the results used for tolerance
calculation represented field trial application rates and PHIs within
25% of the maximum label application rate and minimum label PHI,
respectively.  The data were obtained from the DER for MRID 47545401.
The residue values used to calculate the tolerance are provided in Table
 A..

The dataset was not small (16 samples).  Residues of dinotefuran, DN and
UF were above the LOQ in/on all field trial samples.  

The dataset was entered into the tolerance spreadsheet.  Visual
inspection of the lognormal probability plot (Figure 1) provided in the
spreadsheet indicated that the dataset was reasonably lognormal, which
was confirmed by the approximate Shapiro-Francia test statistic (Figure
2).

Using the tolerance spreadsheet, the recommended tolerance for the leafy
Brassica greens subgroup is 15 ppm.  

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n leafy Brassica greens, subgroup 5B.

Regulator:	EPA

Chemical:	Dinotefuran

Crop:	Mustard greens

PHI:	1 day

App. Rate:	0.179 lb ai/A/application (0.36 lb ai/A/season)

Submitter:	IR-4

MRID Citation:	MRID No. 47545401

	Combined Residues of Dinotefuran, DN and UF (ppm)

	1.579

	1.956

	6.460

	5.376

	6.283

	5.611

	2.791

	3.245

	7.483

	7.834

	7.101

	7.802

	4.589

	5.703

	2.622

	3.895

Figure 1.	Lognormal probability plot of dinotefuran field trial data for
mustard greens.

Figure -2.	Tolerance spreadsheet summary of flonicamid field trial data
for mustard greens.

Dinotefuran	Summary of Analytical Chemistry and Residue Data	DP#: 
358024

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