UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

	OFFICE OF CHEMICAL SAFETY

	AND POLLUTION PREVENTION

  SEQ CHAPTER \h \r 1 MEMORANDUM

Date:   July 1, 2015

SUBJECT:	Cyprodinil.  Expansions of Existing Crop Group/Representative Commodity Uses to Stone Fruit Group 12-12, and Adding New Uses on the Artichoke, Guava, Pomegranate, Passionfruit, Feijoa,Jaboticaba, Wax Jambu, Starfuit, and Acerola and Amended Uses on Greenhouse Cucumbers and Small Tomatoes.   Summary of Analytical Chemistry and Residue Data.

PC Code:  288202	DP Barcode:  D421157

Decision No.:  490951	Registration Nos.:  100-828, 100-953 and 100-1317

Petition No.:  4E8273	Regulatory Action:  Section 3

Risk Assessment Type:  NA	Case No.: 7025

TXR No.:  NA	CAS No.:  121552-61-2

MRID No.:  49346901 – 05	40 CFR:  180.532

FROM:		Thurston G. Morton, Chemist

	Risk Assessment Branch 4

	Health Effects Division (7509P)

THROUGH:	Charles Smith, Acting Branch Chief

	Risk Assessment Branch 4

		Health Effects Division (7509P)

			And

		Sheila Piper,Senior Chemist

		RAB6/HED, 7509P, Chemistry Science Advisory Council (ChemSAC)

		Sumitra Bose Biswas, Chemist

		RAB6/HED, 7509P, ChemSAC

TO:			Laura Nollen/Barbara Madden, RM20

		Minor Use & Emergency Response Branch

Registration Division (7505P)

	  SEQ CHAPTER \h \r 1   SEQ CHAPTER \h \r 1

Executive Summary

Cyprodinil is an anilino-pyrimidine fungicide used to control various plant diseases on a wide variety of fruit, nut, vegetable and herb crops.  Under PP#4E8273, Interregional Research Project No. 4 (hereafter referred to as IR-4), on behalf of the Agricultural Experiment Stations, is requesting the establishment of tolerances for residues of cyprodinil [4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidinamin] in/on the following raw agricultural commodities:

Artichoke…..	4.0 ppm

Guava	1.5 ppm

Passionfruit………………..………………….……………… .1.5 ppm

Feijoa………………..………………….………….……… ….1.5 ppm Jaboticaba………………..………………….……………..… .1.5 ppm

Wax Jambu………………..………………….……………….1.5 ppm

Starfruit 	1.5 ppm

Acerola	1.5 ppm

Pomegranate	7.0 ppm

Fruit, stone, group 12-12……………...	2.0 ppm

In addition, IR-4 is requesting the removal of the currently established tolerance for residues of cyprodinil in/on Fruit, stone, group 12 (2.0 ppm) once the fruit, stone, group 12-12 is established.

In conjunction with PP#4E8273, IR-4 is requesting a Section 3 registration for Vanguard™ WG (EPA Reg. No. 100-828), a 75% water dispersible granule (WDG) formulation for use on artichoke, acerola, feijoa, guava, jaboticaba, passionfruit, starfruit, and wax jambu; Switch® 62.5 WG Fungicide (EPA Reg. No. 100-953), a 37.5% water dispersible granule (WDG) formulation of cyprodinil for use on guava, passionfruit, starfruit, and pomegranate (post-harvest); and Inspire Super ™ Fungicide (EPA Reg. No. 100-1317), a 2.09 lb ai/gallon emulsion oil in water (EW) formulation to artichoke.  In support of these new uses, IR-4 has submitted new magnitude of the residue data for cyprodinil using the WDG formulation of cyprodinil at the proposed use rate.

In addition, IR-4 is requesting amendments for the Section 3 registrations for Vanguard™ WG (EPA Reg. No. 100-828) and Inspire Super ™ Fungicide (EPA Reg. No. 100-1317) to expand currently registered foliar uses for stone fruit group 12 to include the additional commodities specified under the following new crop group:  Fruit, stone, group 12-12.  No amendments to the use patterns (i.e., maximum use rates, retreatment intervals, preharvest intervals, use of adjuvants, etc.) on the subject crops have been proposed.  No new residue chemistry data were submitted to support these uses.  Instead the petitioner wishes to rely on previously submitted residue chemistry data which support the currently registered uses of cyprodinil.

In addition, IR-4 is proposing to remove the restriction against using Vanguard™ WG (EPA Reg. No. 100-828) and Switch® 62.5 WG Fungicide (EPA Reg. No. 100-953) on small tomatoes along with removing the restriction against using Inspire Super ™ Fungicide (EPA Reg. No. 100-1317) on greenhouse cucumbers.  IR-4 has submitted new greenhouse grown cucumber magnitude of the residue data to demonstrate that the existing tolerance for residues of cyprodinil in/on vegetable, cucurbit, group 9 (0.70 ppm) is adequate for the proposed use.  IR-4 has also submitted new small tomato magnitude of the residue data to demonstrate the existing tolerance for residues of cyprodinil in/on vegetable, fruiting, group 8-10 (1.5 ppm) is adequate for the proposed use.

One of the products (EPA Reg. No. 100-1317) addressed herein contains a second active ingredient (difenoconazole) and another product (EPA Reg. No. 100-953) also contains a second active (fludioxonil).  Difenoconazole and fludioxonil are addressed under separate reviews.  The subject review addresses the proposed uses and supporting data for cyprodinil only.

The nature of cyprodinil residues in plants is understood based on adequate metabolism studies on apple, peach, potato, tomato, and wheat.  Only residues of parent cyprodinil need to be included in the tolerance expression and considered for risk assessment for plant commodities.

The nature of cyprodinil residues in ruminants is also understood based on an adequate goat metabolism study.  The residues of concern in ruminants are cyprodinil and its hydroxylated metabolite CGA-304075 (free and conjugated).  No poultry metabolism study is available, but HED has concluded that none is required.  There are no new livestock feed stuffs associated with the proposed new uses of cyprodinil.

Adequate HPLC/UV methods (Methods AG-631 and AG-631B) are available for enforcing tolerances of cyprodinil in/on plant commodities.  The limits of quantitation (LOQ) for the plant methods range from 0.01 to 0.065 ppm depending on the commodity.  An adequate LC/MS method (GRM010.01A) is also available for enforcing tolerances of cyprodinil residues in livestock commodities.  The method LOQ for this method is 0.02 ppm for the combined residues of cyprodinil and its metabolite CGA-304075 (free and conjugated), expressed as parent.

In the submitted field trial study, residues of cyprodinil were determined with a method using high performance liquid chromatography with a tandem mass spectrometer (LC/MS/MS), which is a modified version of the HPLC/UV Syngenta Method AG-631B, “Analytical Method for the Determination of Residues of CGA-219417 in Crops by High Performance Liquid Chromatography with Column Switching.”  Syngenta Methods AG-631 and AG-631B are the current tolerance enforcement methods for determining cyprodinil in plant commodities.

Cucumber, globe artichoke, guava, pomegranate, and tomato samples were stored frozen (-20°C ± 10°C) for up to 12, 2, 22, 11, and 10 months before analysis, respectively.  The stability of cyprodinil has been demonstrated in a variety of other crops, including mustard greens for 20 months and grape, wine, apple, wheat (ear and stalk), strawberry, and potato for up to 2 years.  Therefore, the submitted field trial data are supported by acceptable storage stability data.

Data are adequate to support the proposed uses of cyprodinil.  The HAFT residue level of cyprodinil in greenhouse cucumber, globe artichoke, guava, and small greenhouse tomato resulting from four applications for a seasonal rate of 1.3 lb cyprodinil a.i./A was 0.58,  1.33, 0.522, and 1.12 ppm,  respectively. Maximum residue levels of cyprodinil were 0.62 ppm in greenhouse cucumber, 1.52 ppm in globe artichoke, 0.626 ppm in guava, and 1.28 ppm in small greenhouse tomato.  The HAFT residue level and maximum residue level of cyprodinil resulting from post-harvest treatment of pomegranate were 3.42 and 3.60 ppm, respectively.  There are an adequate number of field trials from representative geographical locations.

The Organization for Economic Cooperation and Development (OECD) tolerance calculation procedures were used to determine appropriate tolerance levels.  A tolerance level of 10 ppm for pomegranate, 4.0 ppm for globe artichoke, and 1.5 ppm for guava is appropriate.  The 1.5 ppm tolerance for guava was translated to acerola, feijoa, jaboticaba, passionfruit, starfruit, and wax jambu, in accordance with “Reviewer’s Guide and Summary of HED ChemSAC Approvals for Amending Crop Group/Subgroups [40 CFR 180.41] and Commodity Definitions [40 CFR 180.1(h)]” (B. Schneider, 6/14/06).  Note that the recommended tolerance level for pomegranate is different than that petitioned-for by the registrant due to the decision that each of the post-harvest scenarios/techniques represented by the data constitutes separate datasets for tolerance determination with the OECD tolerance calculation procedures.

No Codex MRLs are established in/on globe artichoke, acerola, feijoa, guava, jaboticaba, passionfruit, starfruit, wax jambu, and pomegranate.  Canadian and Mexican MRLs has not been established for the requested crops.  The Agency will be harmonized with Codex on the fruit, stone, group 12-12 MRL of 2.0 ppm.

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

HED has examined the residue chemistry database for cyprodinil.  With regards to cyprodinil for PP#4E8273, pending submission of a revised Section B (see requirements under Directions for Use) and a revised Section F (see requirements under Proposed Tolerances), there are no residue chemistry issues that would preclude granting amended  registrations for Vanguard™ WG (EPA Reg. No. 100-828), Switch® 62.5 WG Fungicide (EPA Reg. No. 100-953), and Inspire Super ™ Fungicide (EPA Reg. No. 100-1317) to expand currently registered foliar uses for globe artichoke, acerola, feijoa, guava, jaboticaba, passionfruit, starfruit, wax jambu, and pomegranate; along with the expansion of fruit, stone, group 12-12 or establishment of tolerances for residues of cyprodinil only in/on the following commodities:

Artichoke, globe…..	4.0 ppm

Guava	1.5 ppm

Passionfruit………………..………………….……………… .1.5 ppm

Feijoa………………..………………….………….……… ….1.5 ppm Jaboticaba………………..………………….……………..… .1.5 ppm

Wax Jambu………………..………………….……………….1.5 ppm

Starfruit 	1.5 ppm

Acerola	1.5 ppm

Pomegranate…………………………………………………...1 0 ppm

Fruit, stone, group 12-12……………...	2.0 ppm

In addition, the restriction on use of Switch® 62.5 WG Fungicide (EPA Reg. No. 100-953) and Vanguard™ WG (EPA Reg. No. 100-828) on small size tomato may be removed.  The restriction on use of Inspire Super ™ Fungicide (EPA Reg. No. 100-1317) on greenhouse cucurbits may also be removed.

The approved amended registrations for Vanguard™ WG (EPA Reg. No. 100-828), Switch® 62.5 WG Fungicide (EPA Reg. No. 100-953), and Inspire Super ™ Fungicide (EPA Reg. No. 100-1317) are limited to expansions to add the commodities specified under the new crop groups/subgroups and do not include substantive changes to currently registered use patterns (i.e., maximum use rates, retreatment intervals, preharvest intervals, use of adjuvants, etc.).

A human health risk assessment is forthcoming.

860.1200 Directions for Use – Pertains to Cyprodinil Only

Section B of petition 4E8273 pertaining to uses on artichoke should be revised to specify globe artichoke only.  [Note:  IR-4 submitted draft supplemental labels which are substantially similar to Section B of the petition and should be amended as well.]

860.1550 Proposed Tolerances

Section F of petition 4E8273 must be revised as follows.  The recommended tolerance for residues of cyprodinil in/on pomegranate (10 ppm) is not the same as the petitioned-for tolerance (7.0 ppm) due to the decision that data reflecting each of the three post-harvest scenarios/techniques constitute separate datasets for tolerance determination with the OECD tolerance calculation procedures.  In addition the commodity definition should be for Artichoke, globe.

Background

Cyprodinil is an anilino-pyrimidine fungicide used to control various plant diseases on a wide variety of fruit, nut, vegetable and herb crops.  Tolerances for residues of cyprodinil have been established in/on a variety of crop commodities at levels ranging from 0.02-170 ppm [40 CFR §180.532].  Tolerances have also been established at 0.02 ppm for cyprodinil residues in meat byproducts of cattle, goats, horses, and sheep.  No tolerance is established for poultry byproducts.

The chemical structure, nomenclature, and physicochemical properties of the technical grade of cyprodinil are presented in Tables 1 and 2.

Table 1.	Cyprodinil Nomenclature.

Compound

Common name	Cyprodinil

Company experimental name	CGA219417

IUPAC name	(4-cyclopropyl-6-methyl –pyrimidin-2-yl)-phenyl-amine

CAS name	2-pyrimidinamine, 4-cyclopropyl-6-methyl-N-phenyl-

CAS registry number	121552-61-2

End-use product (EP)	75% water-dispersible granule formulation (Vangard® WG Fungicide; EPA Reg. No. 100-828); a multiple active ingredient (MAI) end-use product (Inspire Super ™ Fungicide; EPA Reg. No. 100-1317) formulated as an emulsion [oil] in water (EW), containing 8.4% difenoconazole and 24.1% cyprodinil

Table 2.	Physicochemical Properties of Technical Grade of Cyprodinil.

Parameter	Value	Reference

Melting point/range	75.9 0C	DP#s 345970 and 345182, W. Cutchin, 6/4/08

pH	9.5 at 25 0C (1% aqueous dispersion)

	Density	1.21 g/cm3 at 20 0C

	Water solubility (mg/L at 25 C)	pH 7.6		16

  SEQ CHAPTER \h \r 1 pH 5		20

pH 7		13

pH 9		15

	Solvent solubility (g/L at 25 C)	ethanol		160

acetone		610

toluene		460

n-octanol		160

n-hexane		30

	Vapor pressure	3.8 x 10-6 mm Hg at 25 0C

	Dissociation constant, pKa	4.44 at 20 0C

	Octanol/water partition coefficient, Log(KOW) at 25 C	3.9 at pH 5

4.0 at pH 7

4.0 at pH 9

	UV/visible absorption spectrum

(molar absorption coefficients for the absorbance maximum)	29,200 l/mol∙cm at 270.8 nm (neutral)

29,200 l/mol∙cm at 251.6 nm (acidic)

29,200 l/mol∙cm at 316.8 nm (acidic)

28,400 l/mol∙cm at 270.8 nm (basic)

860.1200  Directions for Use

Table 3.	Summary of Proposed Directions for Use of Cyprodinil

Applic. Timing, Type, and Equip.	Formulation

[EPA Reg. No.]	Applic. Rate

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

(lb ai/A)	PHI

(days)	Use Directions and Limitations

Artichoke1

Broadcast foliar

Ground/Aerial/Chemigation	Vangard WG

75% WDG

[100-828]	0.33	4 implied	1.3	3	A minimum retreatment interval (RTI) of 14 days is proposed.

Broadcast foliar

Ground Only	Inspire Super

2.09 lb/gal EW

[100-1317]	0.33	4 implied	1.3 	3	A minimum retreatment interval (RTI) of 7-10 days is proposed.

Acerola, feijoa, guava, jaboticaba, passionfruit, starfruit, wax jambu

Broadcast foliar

Ground/Aerial/Chemigation	Vangard WG

75% WDG

 [100-828]	0.33	2 by aerial

4 implied	1.3	0	A minimum retreatment interval (RTI) of 7-10 days is proposed.

Broadcast foliar

Ground Only	Switch 62.5WG

37.5% WDG

 [100-953]	0.33	1 by aerial

4 implied	1.3	0	A minimum retreatment interval (RTI) of 7-10 days is proposed.  Aerial application in California only.

Pomegranate (Post-harvest dip/drench)

In-Line Dip/Drench	Switch 62.5WG

37.5% WDG

 [100-953]

	0.45 lb ai/100 gal of water, wax/emulsion, or aqueous dilution of wax/oil emulsion

	1-2

	0.45-0.90 lb ai/100 gal of water, wax/emulsion, or aqueous dilution of wax/oil emulsion 	0	For maximum decay control, treat fruit once before storage and once after storage, prior to marketing.

Green House Grown Cucumbers

Broadcast foliar

Ground Only	Inspire Super

2.09 lb/gal EW

[100-1317]	0.0075 lb ai/1000 ft2	NS	NS 	7	A minimum retreatment interval (RTI) of 7-10 days is proposed.

1 Although not specified in the use directions, the use on artichoke is intended to be for globe artichoke consistent with the supporting data.

Conclusions.  The proposed use directions are sufficient to allow for evaluation of the available residue data.

860.1300 Nature of the Residue - Plants

DP# 219794, G. Kramer, 2/13/96

DP# 233182, G. Kramer, 2/20/98

MARC Decision Memo, DP# 243198, G. Kramer, 3/11/98

The nature of the residue in plants is adequately understood based on acceptable metabolism studies on apple, peach, potato, tomato, and wheat.  These studies indicated that cyprodinil is metabolized primarily by hydroxylation followed by sugar conjugation.  Cleavage of the amino bridge, opening of the pyrimidine ring, opening of the cyclopropyl ring and formation of thiolactic acid conjugates are minor pathways.  Incorporation into starch was observed in potato tubers and wheat grain.  The MARC reviewed these studies and determined that the residue of concern, for purposes of tolerance enforcement and risk assessment, is cyprodinil.

860.1300 Nature of the Residue - Livestock

DP# 233182, G. Kramer, 2/20/98

MARC Decision Memo, DP# 243198, G. Kramer, 3/11/98

DP# 345970 and 345182, G. Kramer, 6/4/08

DP# 362486, J. Stokes, 9/15/09

The nature of the residue in ruminants is adequately understood based on acceptable lactating goat metabolism studies using [14C-phenyl] and [14C-pyrimidinyl] cyprodinil.  The metabolism of cyprodinil in ruminants proceed predominantly via hydroxylation followed by conjugation with sulfuric and glucuronic acid.  Breakdown of the pyrimidinyl ring was seen only in the liver and resulted in Metabolite L1.  Cleavage of the amino bridge between the phenyl and the pyrimidinyl rings was only a minor reaction as indicated by the small amounts of CGA 249287 found in the liver and kidneys of goats dosed with [14C-pyrimidinyl]cyprodinil.

HED originally concluded there were no cyprodinil metabolites of toxicological or regulatory concern in ruminant milk and tissues based on the dietary burden associated with the registered cyprodinil uses at that time (362486, J. Stokes, 09/15/09; 378920, B. Cropp-Kohlligian, 10/27/10).  However, HED noted that if future uses significantly increase the potential livestock dietary burden, then a new cyprodinil feeding study would be required in which residues of cyprodinil and CGA 304075 (both free and conjugated) are determined.  ARIA subsequently has concluded that the residues of concern for both risk assessment and the tolerance definition should include the combined residues of cyprodinil and metabolite CGA-304075 (free and conjugated), expressed in parent equivalents.

A poultry metabolism for cyprodinil has not been submitted and none has been requested since the potential dietary exposure of poultry to cyprodinil residues is extremely low (estimated at 0.005 ppm based on canola meal consumption).  There is no reasonable expectation of finite residues in poultry and egg.  However, if future crops are added that substantially increase the poultry dietary burden, then HED may require a study.

Summary of Metabolites and Degradates to be included in the Risk Assessment and Tolerance Expression for Cyprodinil

Matrix	Risk Assessment 	Tolerance Expression

Plants	cyprodinil	cyprodinil

Livestock	cyprodinil and CGA-304075	cyprodinil and CGA-304075

Water	cyprodinil and CGA 249287	NA

860.1340 Residue Analytical Methods

Enforcement methods.  Adequate HPLC/UV methods with column switching (Syngenta Methods AG-631 and AG-631B) are available for enforcing tolerances of cyprodinil on plant commodities.  The LOQs for these methods range from 0.01 to 0.065 ppm depending on the plant commodities.  Method AG-631B also contains procedures for confirmatory analysis by GC/NPD.

An adequate HPLC/MS method (GRM010.01A) is also available for enforcing tolerances in livestock commodities.  This method determines residues of both parent and the metabolite CGA-304075 (free and conjugated), expressed as parent.  The LOQ is 0.01 ppm for each analyte for a combined LOQ of 0.02 ppm.

Data collection methods.   In the submitted field trial studies, residues of cyprodinil were determined with a method using high performance liquid chromatography with a tandem mass spectrometer (LC/MS/MS), which is a modified version of the HPLC/UV Syngenta Method AG-631B, “Analytical Method for the Determination of Residues of CGA-219417 in Crops by High Performance Liquid Chromatography with Column Switching.”  Syngenta Methods AG-631 and AG-631B are the current tolerance enforcement methods for determining cyprodinil in plant commodities

For method AG-631B, residues of cyprodinil were extracted with methanol:water (8:2, v/v), filtered, and acidified with dilute HCl.  Residues were then cleaned-up by elution through a SPE column with ammoniated methanol.  Residues were concentrated, reconstituted with 0.1% ammonium acetate, and analyzed by LC/MS/MS using a Phenomenex Synergi 4 micron Polar-RP 80A column (75 x 2.00 mm) and a multi-component mobile phase (Component A was 0.1% ammonium acetate in water and Component B was 90/10 acetonitrile:water plus 0.1% ammonium acetate) with gradient elution.  The m/z 226.1→93.1 ion transition was used for detection and quantitation of cyprodinil.  Residues were quantified using external standards. The validated LOQ was 0.01 ppm; the LOD was not reported.

The method was validated in conjunction with the analysis of field trial samples.  Control samples of were fortified with cyprodinil at 0.01-2.1 ppm.  Recoveries ranged from 70-109%.  Control samples were fortified with cyprodinil at 0.02-10 ppm.  Recoveries ranged from 68-112%.

Conclusions.  Adequate HPLC/UV methods are available for enforcing the proposed new uses.

All residues of cyprodinil were determined using an adequate HPLC/UV or LC/MS/MS method.

860.1360 Multiresidue Methods

G. Kramer, 11/28/1995

Data are available depicting the recovery of cyprodinil and its metabolite CGA-232449 through FDA Multiresidue method testing protocols (C through E).  Acceptable recoveries were obtained for cyprodinil in apple fortified at 0.50 ppm using Protocol D.  These data were forwarded to FDA.

860.1380 Storage Stability

D233182, G. Kramer, 02/20/98

D288706, T. Bloem ,7/24/03

Cucumber, globe artichoke, guava, pomegranate, and tomato samples were stored frozen (-20°C ± 10°C) for up to 12, 2, 22, 10, and 11 months before analysis, respectively.  The stability of cyprodinil has been demonstrated in a variety of other crops, including mustard greens for 20 months and grape, wine, apple, wheat (ear and stalk), strawberry, and potato for up to 2 years.  Therefore, the submitted field trial data are supported by acceptable storage stability data.

860.1400 Water, Fish, and Irrigated Crops

The proposed uses are not relevant to this guideline.

860.1460 Food Handling

The proposed uses are not relevant to this guideline.

860.1480 Meat, Milk, Poultry, and Eggs

DP#s 345970 and 345182, W. Cutchin, 6/4/08

DP# 362484, J. Stokes, 9/15/09

DP# 378920, B. Cropp-Kohilligian, 10/27/10

Adequate cattle feeding studies are available for cyprodinil, and tolerances for cyprodinil residues in livestock commodities were assessed in conjunction with petitions for tolerances on various plant commodities.  Using the Agency’s most recent guidance on constructing reasonably balanced livestock diets the maximum reasonably dietary burdens (MRDBs) of livestock for cyprodinil residues were calculated to be 0.88 ppm for beef cattle, 1.2 ppm for dairy cattle, and 0.005 ppm for poultry and swine.  Based on these MDBs, tolerances for residues of cyprodinil and free and conjugated CGA-304075, expressed in parent equivalents, were required on meat byproducts of cattle, goats, horses, and sheep at 0.02 ppm (LOQ).

Previously, HED recalculated the dietary burden using almond hull in place of wet apple pomace.  The dietary contribution from the almond hulls alone did not increase the total dietary burden.  However, this proposed amended use on almonds was withdrawn and the increased tolerance for almond hulls did not occur.

Conclusions.  The proposed new uses do not contain any livestock feed stuffs, therefore, HED has determined that the currently established 0.02 ppm tolerance levels for meat byproducts of cattle, goats, horses, and sheep are adequate.

860.1500 Crop Field Trials

MRID #s 49346901, 49346902, 49346903, 49346904, & 49346905

DP# 354013, 3/20/09, B. Cropp-Kohlligian

  SEQ CHAPTER \h \r 1 The results from the field trials are summarized below  SEQ CHAPTER \h \r 1 .

Cucumber (Greenhouse) Small and Large Varieties

Following four applications of a 2.09 lb ai/gal EW formulation at a total application rate of 1.30–1.33 lbs ai/A, individual sample (and per-trial average) residues of cyprodinil were 0.08–0.62 ppm (0.11–0.58 ppm) in/on cucumber fruit collected at a PHI of 0 days.  There were no significant differences between the residues in the large variety cucumbers vs. the small variety cucumbers.

Table 4.  Summary of Residues from Cucumber (Greenhouse) Field Trials with EW Formulation of Cyprodinil.

Crop Matrix	Total Application Rate

(lb ai/A)	PHI (days)	n1	Residues (ppm)

Min.2	Max.2	LAFT3	HAFT3	Median3	Mean3	SD3

Cyprodinil

Cucumber (Large and Small), fruit	1.3030–1.3276	0	5	0.08	0.62	0.11 0.58	0.34	0.32	0.20

1  n = number of field trials.

2  Values based on total number of samples.

3  Values based on per-trial averages.  LAFT = lowest average field trial, HAFT = highest average field trial, SD = standard deviation.  For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ.  The LOQ was 0.015 ppm for cyprodinil in all matrices.

Artichoke, globe

Following four or five applications of a 2.09 lb ai/gal EW formulation at a total application rate of 1.300–1.655 lbs ai/A, individual sample (and per-trial average) residues of cyprodinil were 0.825–1.52 ppm (0.932–1.33 ppm) in/on mature globe artichoke flower buds collected at a PHI of 3 days.  There were no significant differences between the residues in the perennial globe artichokes vs. the annual globe artichokes.

Table 5.	Summary of Residues from Globe Artichoke Field Trials with EW Formulation of Cyprodinil.

Crop Matrix	Total Application Rate

(lb ai/A) 4	PHI (days)	n1	Residues (ppm)

Min.2	Max.2	LAFT3	HAFT3	Median3	Mean3	SD3

Cyprodinil

Globe artichoke, mature flower buds	1.300–1.655	3	4	0.825	1.52	0.932 1.33	1.22	1.17	0.18

1  n = number of field trials.

2  Values based on total number of samples.

3  Values based on per-trial averages.  LAFT = lowest average field trial, HAFT = highest average field trial, SD = standard deviation.  For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ.  The LOQ was 0.01 ppm for cyprodinil in all matrices.

4 Calculated by the reviewer.

Side-by-side field trial data on lettuce, mustard greens and tomatoes comparing residues of cyprodinil resulting from multiple late season uses of the EW formulation with a WDG formulation of cyprodinil are available (DP# 354013, 3/20/09, B. Cropp-Kohlligian).  Cyprodinil residues were similar for the EW and WDG formulations on all three crops.

Guava

Following four applications of Switch 62.5WG at a total application rate of 1.31–1.43 lbs ai/A, individual sample (and per-trial average) residues of cyprodinil were 0.345–0.626 ppm (0.353–0.522 ppm) in/on guava fruit collected at a PHI of 0 days.

Table 6.	Summary of Residues from Guava Field Trials with WDG Formulation of Cyprodinil.

Crop Matrix	Total Application Rate

(lb ai/A) 4	PHI (days)	n1	Residues (ppm)

Min.2	Max.2	LAFT3	HAFT3	Median3	Mean3	SD3

Cyprodinil

Guava fruit	1.31–1.43	0	4	0.345	0.626	0.360	0.522	0.487	0.464	0.07

1  n = number of independent field trials.

2  Values based on total number of samples.

3  Values based on per-trial averages.  LAFT = lowest average field trial, HAFT = highest average field trial, SD = standard deviation.  For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ.  The LOQ was 0.01 ppm for cyprodinil in all matrices.

4 Calculated by the reviewer.

Pomegranate (Post-Harvest)

Data reflect three different post-harvest treatment scenarios/techniques of 1 or 2 applications using a water dispersible granule (WDG) formulation of cyprodinil (Switch 62.5WG™).  Each of these post-harvest scenarios/techniques are considered separate/discrete datasets for tolerance determination.  Following one application as a dip with wax at 0.45 lb ai/100 gal, individual sample (and per-trial average) residues of cyprodinil were 0.24-1.60 ppm (0.93-1.52 ppm) in/on pomegranate collected on the day of treatment.  Following a total of two applications, one application as a dip with wax at 0.45 lb ai/100 gal and a second application as a dip with no wax at 0.45-0.46 lb ai/100 gal, individual sample (and per-trial average) residues of cyprodinil were 2.22-3.60 ppm (2.56-3.42 ppm) in/on pomegranate treated and collected on the same day.  Following a total of two applications, one application as a dip with wax at 0.45-0.46 lb ai/100 gal and then a drench application with no wax at 0.45-0.46 lb ai/100 gal, individual sample (and per-trial average) residues of cyprodinil were 0.38-2.69 ppm (0.53-2.25 ppm) in/on pomegranate treated and collected on the same day.

Table 7.  Summary of Residues from Pomegranate Post-Harvest Trials with WDG Formulation of Cyprodinil.

Crop Matrix	Total Application Rate

(oz ai/100gal)1/

[lb ai/100 gal]1	PHI (days)	n2	Residues (ppm)

Min.3	Max.3	LAFT4	HAFT4	Median4	Mean4	SD4

Cyprodinil

Pomegranate	7.2 / [0.45] 5	0	4	0.24	1.60	0.93	1.52	1.155	1.02	0.576

Pomegranate	14.4-14.6 / [0.9] 6	0	4	2.22	3.60	2.56	3.42	3.260	3.13	0.384

Pomegranate	14.4-14.6 / [0.9] 7	0	4	0.38	2.69	0.53	2.25	1.845	1.55	0.893

1  Calculated by the reviewer.

2  n = number of independent trials.

3  Values based on total number of samples.

4  Values based on per-trial averages.  LAFT = lowest average field trial, HAFT = highest average field trial, SD = standard deviation.  For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ.  The LOQ was 0.01 ppm for cyprodinil in all matrices.

5  One application as a dip with wax.

6  Total of two applications.  One application as a dip with wax (0.45-0.46 lb ai/100 gal) and a second application as a dip with no wax (0.45-0.46 lb ai/100 gal).  Applications were allowed to dry before the second application was applied.  Samples were treated and collected on the same day.

7  Total of two applications.  One application as a dip with wax (0.45-0.46 lb ai/100 gal) and then a drench application with no wax (0.45-0.46 lb ai/100 gal).  Applications were allowed to dry before the second application was applied.  Samples were treated and collected on the same day.

Tomato (Greenhouse) Small Varieties

Following four applications of a 37.5% water dispersible granule (WDG) formulation at a total application rate of 1.31-1.33 lb ai/A, individual sample (and per-trial average) residues of cyprodinil were 0.278–1.28 ppm (0.317–1.12 ppm) in/on tomato fruit collected at a PHI of 0 days.

Table 8.	Summary of Residues from Tomato (Greenhouse) Small Variety Field Trials with WDG Formulation of Cyprodinil.

Crop Matrix	Total Application Rate

(lb ai/A)4	PHI (days)	n1	Residues (ppm)

Min.2	Max.2	LAFT3	HAFT3	Median3	Mean3	SD3

Cyprodinil

Tomato fruit	1.31-1.33	0	3	0.278	1.28	0.317	1.12	0.365	0.600	0.45

1  n = number of independent field trials.

2  Values based on total number of samples.

3  Values based on per-trial averages.  LAFT = lowest average field trial, HAFT = highest average field trial, SD = standard deviation.  For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ.  The LOQ was 0.01 ppm for cyprodinil in all matrices.

4 Calculated by the reviewer.

Conclusion: The data adequately support the requested tolerances and proposed use patterns.

860.1520 Processed Food and Feed

None of the new uses have processed commodities that require a processing study.

860.1550 Harmonization with Codex

No Codex MRLs are established in/on globe artichoke, acerola, feijoa, guava, jaboticaba, passionfruit, starfruit, wax jambu, and pomegranate.  Canadian and Mexican MRLs have not been established for the requested crops.  The Agency with be harmonized with Codex on the fruit, stone, group 12-12 MRL of 2.0 ppm.

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

Analytical standards for cyprodinil (expiration date 7/30/2018) and CGA-304075 (expiration date 8/31/2016) are currently available in the EPA National Pesticide Standards Repository (email communication with T. Cole, ACB, 04/08/2015).

860.1850/1900 Confined and Field Accumulation in Rotational Crops

DP# D257898, S. Levy, 2/8/2000

DP# D326346, W. Wassell, 10/18/2006

Adequate confined and limited field rotational crop studies are available and were conducted at 2.2x and 1.5x the current maximum use rate for rotated crops (1.3 lb ai/A).  On the basis of these studies, the HED requested a field rotational crop study which also monitored for residues of CGA-232449, NOA-422054, CGA-249287, and CGA-263208.

In the subsequent field accumulation study, cyprodinil (WDG) was applied to mustard greens at four test sites in CA (2 tests) and NY (2 tests) as four broadcast foliar applications at 0.328 lb ai/A/application at 7-day retreatment intervals for a total of 1.31 lb ai/A (1x rate).  The primary mustard greens crop was destroyed and removed 7 days after the final application, and rotational crops of wheat, lettuce and garden beets were planted at PBIs of 27 to 32 days.  Samples of lettuce, garden beet roots and tops, and wheat forage, hay, straw and grain were collected from each test at the appropriate stage of maturity.  All samples were analyzed for residues of parent and each metabolite (CGA-232449, NOA-422054, CGA-249287, and CGA-263208) using an adequate HPLC/MS method (Method 2213-01), which has a validated LOQ of 0.05 ppm for parent and each metabolite.

As residues of parent and each metabolite were <LOQ in/on all lettuce, garden beet and wheat RAC samples, HED concluded that rotational crop tolerances are not currently required.

860.1550 Proposed Tolerances

The Agency has determined that the residue of concern in plant commodities for the tolerance expression is only cyprodinil.   Tolerances have been established for residues of cyprodinil in/on a variety of crop commodities, at levels ranging from 0.02 ppm in/on almond to 340 ppm in citrus oil [40 CFR §180.532(a)].  Tolerances have also been established at 0.02 ppm for cyprodinil and its metabolite CGA-304075 residues in meat byproducts of cattle, goats, horses and sheep.

Table 8. 	Tolerance Summary for Cyprodinil

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

Tolerances Proposed Under PP#4E8273

Artichoke	4.0	4.0	Artichoke, globe

Guava	1.5	1.5	---

Passionfruit	1.5	1.5	---

Feijoa	1.5	1.5	---

Jaboticaba	1.5	1.5	---

Wax Jambu	1.5	1.5	---

Starfruit	1.5	1.5	---

Acerola	1.5	1.5	---

Pomegranate	7.0	10	---

Fruit, stone, group 12-12	2.0	2.0	---

References

DP Numbers:	378920

Subject:		Cyprodinil.  Cyprodinil.  Amended Use and Amended Tolerance Petition for Pome Fruit.  Summary of Analytical Chemistry and Residue Data.

From:		B. Cropp-Kohlligian

To:		L. Jones

Dated:		10/27/10

MRID(s):	47644301

DP Numbers:	362486

Subject:		Cyprodinil.  Petition for Tolerance on Canola Seed Imported from Canada.  Summary of Analytical Chemistry and Residue Data.

From:		J. Stokes

To:		L. Jones

Dated:		09/15/09

MRID(s):	47644301

DP Numbers:	345970 and 345182

Subject:		Cyprodinil.  Section 3 Requests for Uses on Tomato, Avocado, Herbs, Root Vegetables, Leaves of Root and Tuber Vegetables, Lemon, Lime, Cucurbits, Kiwifruit, Green and Dry Bulb Onions, and Strawberries.  Registrant’s Response to Conditional Registration on Carrots and Brassica Vegetables and Livestock Feeding Study.  Summary of Analytical Chemistry and Residue Data.

From:		W. Cutchin

To:		W. Cutchin/B. Madden

Dated:		06/04/08

MRID(s):	47161101-47161107 and 47169305-47169311

DP Number:	326346

Subject:		Registration:  100-953; PP#8E05012; Cyprodinil on Onions.  Review of Revised Label, Field Accumulation in Rotational Crops, Storage Stability, and Analytical Methods Data Requested as Conditions of Registration.

From:	W. Wassell

To:	L. Jones/M. Waller

Dated:	10/18/06

MRID(s):	46078901, 46078903, 46165901

DP Number:	288706, 288708, 288710, and 288773

Subject:		Cyprodinil (PC Code 288202).  Section 3 Registration for Application of Cyprodinil to Lychee, Longan, Spanish Lime, Rambutan, and Pulasan (ID# - 2E06447); Brassica Leafy Greens Crop Subgroup, Head and Stem Brassica Crop Subgroup, and Turnip Greens (ID# - 2E06485); Carrot (ID# - 2E06461); and Herb Crop Subgroup (ID# - 3E06529).  Summary of Residue Chemistry Data.

From:		T. Bloem

To:		R. Forrest

Dated:		07/24/03

MRID(s):	45682401, 45721502, 45726101, 45726102, 45795301, 45795302, and 45839801

DP Number:	257898

Subject:	PP# 8E05012.  Cyprodinil in/on Strawberries and Bulb Vegetables (Crop Group 3).  Evaluation of Residue Data and Analytical Methods.

From:	S. Levy

To:	R. Forrest/S. Brothers

Dated:	02/08/00

MRID(s):	44615602, 44615601, 44867312, 44867314

DP Numbers:	243198

Subject:	Cyprodinil.  HED Metabolism Assessment Review Committee Meeting of 02/10/98.

From:	G. Kramer

To:	HED MARC Members

Dated:	03/11/98

MRID(s):	None

DP Numbers:	233561, 233562, 233928, 233182, 239674, and 236086

Subject:	PP# 6F04656. New Chemical- Cyprodinil (i.e., Vangard®) in/on Stone Fruit, Pome Fruit, Almonds and Grapes. Evaluation of Residue Data and Analytical Methods.

From:	G. Kramer

To:	M. Waller/T. Ellwanger

Dated:	02/20/98

MRID(s):	44186401, 44186404 and 44186410 thru 44186420; 43908402, 43908403 and 43908438 thru 43908445; 44382601; and 44275401 and 44275402

DP Number:	219794

Subject:	PP#s 5G04553.  New Chemical – Cyprodinil and Propiconazole in or on Stone Fruit.  Evaluation of Residue Data and Analytical Methods.

From:	G. Kramer

To:	C. Welch/ K. Whitby

Dated:	02/13/96

MRID(s):	43709001 through 43709004, 43709048 through 43709055, and 43737603

DP Number:	None

Subject:	Multiresidue Method Testing Data for Cyprodinil and CGA-232449

From:	G. Kramer

To:	B. McMahon, FDA

Dated:	11/28/95

MRID(s):	43709050

  SEQ CHAPTER \h \r 1 Attachments:

Appendix I - International Tolerances

Appendix II – Tolerance Assessment Calculations

F.	DOCUMENT TRACKING

RDI:  C. Smith 07/01/15

Petition Number: 4E8273

DP#: 421157

PC Code: 288202

Template Version September 2005

Appendix I.  International Tolerances

Cyprodinil (PC Code 288202; 03/12/15)

Summary of US and International Tolerances and Maximum Residue Limits

Residue Definition:

US	Canada	Mexico2	Codex

40 CFR 180.532:

Plant: Cyprodinil (4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidinamine). 4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidinamine

Cyprodinil

The residue is fat soluble.

Commodity1	Tolerance (ppm) /Maximum Residue Limit (mg/kg)

	US	Canada	Mexico2	Codex

Artichoke, globe	4.0

	Guava	1.5

	Passionfruit	1.5

	Feijoa	1.5

	Jaboticaba	1.5

	Wax Jambu	1.5

	Starfruit 	1.5

	Acerola	1.5

	Pomegranate	10

	Fruit, stone, group 12-12	2.0

	2

Completed: M. Negussie; 03/19/15

1 Includes only commodities of interest for this action.  Tolerance values should be the HED recommendations and not those proposed by the applicant.

2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes.

Appendix II.  Tolerance Assessment Calculations.

For each of the crops listed below, the OECD MRL Calculator User Guide (SOP), along with the tolerance spreadsheet, was used for calculating recommended tolerances.  As specified in the SOP, the tolerance calculation is in the region of the 95th percentile of the underlying residue distribution, and is more likely to overestimate rather than underestimate the 95th percentile.  The rounding procedures specified in the SOP were also used.  The OECD tolerance spreadsheet does not require the use of maximum-likelihood estimation (MLE) procedures for values <LOQ.

Using the OECD MRL Calculator, the recommended tolerances are 1.5 ppm for guava, 10 ppm for pomegranate, and 4.0 ppm for globe artichoke.

Cyprodinil

Guava

US

1.31-1.43 lb ai/A

Total number of data (n)	4

Percentage of censored data	0%

Number of non-censored data	4

Lowest residue	0.360

Highest residue	0.522

Median residue	0.487

Mean	0.464

Standard deviation (SD)	0.071

Correction factor for censoring (CF)	1.000

Proposed MRL estimate

- Highest residue	0.522

- Mean + 4 SD	0.749

- CF x 3 Mean	1.392

Unrounded MRL	1.392

Rounded MRL	1.5

 High uncertainty of MRL estimate.

[Small dataset]

Residues (mg/kg)	n

0.36	1

0.483	1

0.491	1

0.522	1

Cyprodinil

Pomegranate

US

0.9 lb ai/100 gal1

Total number of data (n)	4

Percentage of censored data	0%

Number of non-censored data	4

Lowest residue	2.560

Highest residue	3.420

Median residue	3.260

Mean	3.125

Standard deviation (SD)	0.384

Correction factor for censoring (CF)	1.000

Proposed MRL estimate

- Highest residue	3.420

- Mean + 4 SD	4.662

- CF x 3 Mean	9.375

Unrounded MRL	9.375

Rounded MRL	10

 High uncertainty of MRL estimate.

[Small dataset]

Residues (mg/kg)	n

2.56	1

3.26	2

3.42	1

1  Total of two applications.  One application as a dip with wax (0.45-0.46 lb ai/100 gal) and a second application as a dip with no wax (0.45-0.46 lb ai/100 gal).  Applications were allowed to dry before the second application was applied.  Samples were treated and collected on the same day.

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Standard deviation (SD)	0.180

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Proposed MRL estimate

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- Mean + 4 SD	1.894

- CF x 3 Mean	3.519

Unrounded MRL	3.519

Rounded MRL	4

 High uncertainty of MRL estimate.

[Small dataset]

Residues (mg/kg)	n

0.932	1

1.14	1

1.29	1

1.33	1

Cyprodinil	Summary of Analytical Chemistry and Residue Data	DP#:  421157

Page   PAGE  21  of   NUMPAGES  21


[Federal Register Volume 79, Number 19 (Wednesday, January 29, 2014)]
[Notices]
[Pages 4783-4785]
[FR Doc No: 2014-01658]

-----------------------------------------------------------------------

SECURITIES AND EXCHANGE COMMISSION

[Release No. 34-71374; File No. SR-BOX-2014-05]

Self-Regulatory Organizations; BOX Options Exchange LLC; Notice
of Filing and Immediate Effectiveness of a Proposed Rule Change To
Amend the BOX Rules To Remove the BOX-Top Order

January 23, 2014.
    Pursuant to Section 19(b)(1) of the Securities Exchange Act of 1934
(``Act''),\1\ and Rule 19b-4 thereunder,\2\ notice is hereby given that
on January 14, 2014, BOX Options Exchange LLC (``Exchange'') filed with
the Securities and Exchange Commission (``Commission'') the proposed
rule change as described in Items I and II below, which Items have been
prepared by the self-regulatory organization. The Commission is
publishing this notice to solicit comments on the proposed rule from
interested persons.
---------------------------------------------------------------------------

    \1\ 15 U.S.C. 78s(b)(1).
    \2\ 17 CFR 240.19b-4.
---------------------------------------------------------------------------

I. Self-Regulatory Organization's Statement of the Terms of Substance
of the Proposed Rule Change

    The Exchange proposes to amend the BOX Rules to remove the BOX-Top
Order. The text of the proposed rule change is available from the
principal office of the Exchange, at the Commission's Public Reference
Room and also on the Exchange's Internet Web site at http://boxexchange.com.

II. Self-Regulatory Organization's Statement of the Purpose of, and
Statutory Basis for, the Proposed Rule Change

    In its filing with the Commission, the self-regulatory organization
included statements concerning the purpose of, and basis for, the
proposed rule change and discussed any comments it received on the
proposed rule change. The text of these statements may be examined at
the places specified in Item IV below. The self-regulatory organization
has prepared summaries, set forth in Sections A, B, and C below, of the
most significant aspects of such statements.

A. Self-Regulatory Organization's Statement of the Purpose of, and
Statutory Basis for, the Proposed Rule Change

1. Purpose
    The purpose of this proposed rule change is to amend the BOX rules
to remove the BOX-Top Order. A BOX-Top Order is currently defined as an
order entered into the BOX Book which is executed at the best price
available in the market for the total quantity available from any
contra bid (offer).\3\ Any residual volume left after part of a BOX-Top
Order has been executed is automatically converted to a limit order at
the price at which the original BOX-Top Order was executed, except when
a BOX-Top Order executes against a Legging Order at a penny increment
in a series traded in a larger increment. In this instance, the
remaining BOX-TOP Order quantity will be priced, ranked and displayed
on the BOX Book at the nearest increment tick permitted for the series
(rounded up (down) in the case of a sell (buy) order).
---------------------------------------------------------------------------

    \3\ See BOX Rule 7110(c)(2).
---------------------------------------------------------------------------

    BOX-Top Orders were originally introduced at the launch of the
Exchange in 2004 to fulfill a market need.\4\ Specifically, the
Exchange created BOX-Top Orders because the Exchange did not offer
Market Orders when it launched.\5\ However, shortly after the Exchange
launched, Participants expressed their preference for Market Orders
instead of BOX-Top Orders. Due to these requests the Exchange decided
to offer Market Orders as well.\6\ Once the Exchange began offering
Market Orders the popularity of BOX-Top Orders drastically decreased
due to the preference by Participants for Market Orders; as a result,
the BOX-Top Order is rarely used by Participants today. The Exchange
has spoken with Participants who currently use BOX-Top Orders and has
verified that removing this order type will have no impact on their
ability to trade on the Exchange. Consequently, the Exchange believes
that the continued presence of the BOX-Top Order as an order type
offered by the Exchange no longer serves a business purpose and could
lead to investor confusion.
---------------------------------------------------------------------------

    \4\ See Securities Exchange Act Release No. 49068 (January 13,
2004), 69 FR 2775 (January 20, 2004) (Order Approving SR-BSE-2002-
15).
    \5\ Id.
    \6\ See Securities Exchange Act Release No. 51821 (June 10,
2005), 70 FR 35143 (June 16, 2005) (Order Approving SR-BSE-2004-51).
---------------------------------------------------------------------------

    The Exchange notes that while very similar, BOX-Top Orders are not
identical to Market Orders. After execution, the residual volume of a
BOX-Top Order is automatically converted to a limit order at the price
at which the BOX-Top Order was executed.\7\ With a Market Order the
residual volume is executed at the next best price available for the
total quantity

available under [sic] the Market Order is fully executed. The Exchange
believes the lack of demand for the BOX-Top Order demonstrates that
this capability is not important to Participants. Further, the
filtering process at each price level ensures that the Market Order
will not trade through the NBBO.
---------------------------------------------------------------------------

    \7\ Except when the BOX-Top Order executes a Legging Order at a
penny increment in a series trader [sic] in a larger increment.
---------------------------------------------------------------------------

    Accordingly, the Exchange proposes to remove all references to BOX-
Top Orders in the Exchange rules. First, the Exchange proposes to amend
Rule 7130(b) (Filtering of BOX In-Bound Orders) to remove references to
[sic] BOX-Top Order. All inbound orders to BOX (with the exception of
Improvement Orders and Primary Improvement Orders submitted during a
PIP, Directed Orders, and Intermarket Sweep Orders) are filtered by the
Trading Host prior to entry on the BOX Book to ensure that these orders
will not, in the case of a sell (buy) order, execute at a price below
(above) the NBBO price.\8\
---------------------------------------------------------------------------

    \8\ See Rule 7130(b).
---------------------------------------------------------------------------

    Once BOX-Top Orders are removed the Exchange will continue to
filter all inbound orders (with the exception of Improvement Orders and
Primary Improvement Orders submitted during a PIP, Directed Orders, and
Intermarket Sweep Orders) to ensure that these orders will not, in the
case of a sell (buy) order, execute at a price below (above) the NBBO
price.\9\ Further, since these inbound orders to BOX will continue to
be filtered, Participants will remain protected when entering orders.
Therefore, the Exchange believes that the removal of the BOX-Top Order
as an order type will not have any impact on Participants or the
Exchange's systems.
---------------------------------------------------------------------------

    \9\ Id.
---------------------------------------------------------------------------

    Second, the Exchange proposes to amend Rule 7150 (Price Improvement
Period) to remove references to the BOX-Top Order. Currently, Options
Participants, both OFPs and Market Makers, executing agency orders may
designate BOX-Top Orders for price improvement and submission to the
PIP.\10\ Under the current PIP rules the submission of a BOX-Top Order
or Market Order on the same side as a PIP Order will prematurely
terminate the PIP when, at the time of the submission of the BOX-Top
Order or Market Order, the best Improvement Order is equal to or better
than the NBBO on the same side of the market as the Best Improvement
Order.\11\
---------------------------------------------------------------------------

    \10\ See Rule 7150(f).
    \11\ See Rule 7150(i).
---------------------------------------------------------------------------

    Once references to BOX-Top Orders are removed from the Exchange's
rules Participants will be able to access the PIP by submitting Market
Orders and marketable limit Customer Orders.\12\ Further, the
submission of a Market Order on the same side as a PIP Order will
continue to prematurely terminate the PIP when, at the time of the
submission of the Market Order, the best Improvement Order is equal to
or better than the NBBO on the same side of the market as the Best
Improvement Order. Therefore, the Exchange believes that the removal of
the BOX-Top Order from the PIP will not have any impact on Participants
or the Exchange's systems.
---------------------------------------------------------------------------

    \12\ See Rule 7150(f).
---------------------------------------------------------------------------

    Third, the Exchange proposes to amend Rule 7240 (Complex Orders) to
remove references to the BOX-Top Order. Currently, Options Participants
may enter Complex Orders as BOX-Top Orders.\13\ BOX-Top Complex Orders
are executed at the best price available on the market for the total
quantity available from any contra bid (offer). Any residual volume
left after part of a BOX-Top Complex Order has been executed is
automatically converted to a limit order on the Complex Order Book at
the net Strategy price at which the original BOX-Top Complex Order was
executed.\14\ All inbound Complex Orders to BOX, including BOX-Top
Complex Orders, are filtered to ensure that each leg of the Complex
Order will be executed at a price that is equal to or better than the
NBBO and the BOX BBO for each of the component series.\15\ If an
inbound BOX-Top Complex Order or Market Complex Order is not executable
on BOX but is executable against cNBBO, the BOX-Top Complex Orders or
Market Complex Orders will be exposed on the Complex Order Book at cNBB
(in the case of a sell order) or cNBO (in the case of a buy order) for
a period of up to one second.\16\ Any executable, opposite side orders
received during the exposure period, including interest on the BOX
Book, will immediately execute against the exposed Complex Order.\17\
Any unexecuted quantity remaining at the end of the exposure period
will be cancelled.\18\
---------------------------------------------------------------------------

    \13\ See Rule 7240(b)(4).
    \14\ Id.
    \15\ See Rule 7240(b)(3)(iii).
    \16\ See Rule 7240(b)(3)(iii)(B). The exposure period is
currently set at 100 milliseconds.
    \17\ Id.
    \18\ See Rule 7240(b)(3)(iii)(C).
---------------------------------------------------------------------------

    Once BOX-Top Orders are removed from the Exchange's rules, inbound
Market Complex Orders that are not executable on BOX but are executable
against cNBBO will continue to be exposed on the Complex Order Book at
cNBB (in the case of a sell order) or cNBO (in the case of a buy
order).\19\ Further, since all inbound Complex Orders are filtered to
ensure that each leg of a Complex Order is executed at a price that is
equal to or better than the NBBO and the BOX BBO for each of the
component series, Participants will remain protected when entering
Complex Orders. Therefore, the Exchange believes that the removal of
BOX-Top Orders as a type of Complex Orders will not have any impact on
Participants or the Exchange's systems.
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    \19\ See Rule 7240(b)(3)(iii)(B).
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    Fourth, the Exchange proposes to amend Rule 7245 (Complex Order
Price Improvement Period (``COPIP'')) to remove references to BOX-Top
Orders. Consistent with the PIP, Options Participants, both OFPs and
Market Makers, executing agency orders may designate Complex Orders
that are BOX-Top Orders for price improvement and submission to the
COPIP.\20\ The submission to BOX of a BOX-Top Complex Order or Market
Complex Order on the same side as a COPIP Order will prematurely
terminate the COPIP when, at the time of the submission of such orders,
the best Complex Order or BOX Book Interest is equal to or better than
the cNBBO on the opposite side of the COPIP Order.\21\ Once BOX-Top
Orders are removed from the Exchange's rules, Participants will
continue to be able to access the COPIP by submitting Market Orders and
marketable limit orders.\22\ Further, the submission of a Market Order
on the same side as a COPIP Order will continue to prematurely
terminate the COPIP when, at the time of the submission of the Market
Order, the best Complex Order or BOX Book Interest is equal to or
better than the cNBBO on the same side of the COPIP Order.
Additionally, the Exchange is proposing to make a number of non-
controversial changes and technical corrections to its rules. Such
corrections include: removing references to BOX Top Orders in Rule 7070
(Opening the Market) and Interpretive Material to Rule 7080 (IM-7080-1
Trading Conditions During Limit State or Straddle State); removing
references to BOX Top Orders in and renumbering Rule 7110 (Order
Entry); and updating rule references in and renumbering Rule 7130
(Execution and Price/Time Priority); and updating a rule reference in
Rule 8040 (Obligations of Market Makers).
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    \20\ See Rule 7245(f).
    \21\ See Rule 7245(h).
    \22\ See Rule 7245(f).
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    The Exchange believes that the removal of BOX-Top Orders from the
COPIP will not have any impact on Participants or the Exchange's
systems. The Exchange is removing this order

type because it has become obsolete and is rarely used by Options
Participants. The Exchange is proposing to remove any references to the
BOX-Top Order from the BOX Rules and decommission this order type.
After the notice of effectiveness of the proposed rule change, and at
least one week prior to the operative date, the Exchange will issue an
informational circular to inform BOX Participants of the operative date
for the removal of the BOX-Top Order. BOX believes this will give
Participants the opportunity to make any necessary changes to order
entry methodology to coincide with the implementation date.
2. Statutory Basis
    The Exchange believes that the proposal is consistent with Section
6(b) of the Act,\23\ in general, and furthers the objectives of Section
6(b)(5) of the Act,\24\ in particular, by eliminating an outdated and
obsolete order type from the Exchange's rules. Specifically, the
Exchange believes that deleting all references to the BOX-Top Order
will promote just and equitable principles of trade and protect
investors and the public interest, because it will help insure that
investors are not confused by the functionality of different order
types available for trading on the Exchange. As stated above, the BOX-
Top Order is an order type only available on the Exchange, and is
rarely used by Participants. Instead of using the BOX-Top Order to
trade on BOX, Participants prefer to use the Market Order, an order
type that is also traded on other options exchanges and is very similar
to the BOX-Top Order. The Exchange believes that the continued presence
of BOX-Top Orders is confusing to some Participants, particularly new
Participants, who question the functionality of this order type.
Further, the Exchange believes that the proposal removes impediments to
and perfects the mechanism of a free and open market by simplifying the
Exchanges rules, ensuring that Participants, regulators and the public
can more easily navigate the Exchange's rulebook and better understand
the order types available for trading on the Exchange.
---------------------------------------------------------------------------

    \23\ 15 U.S.C. 78f(b).
    \24\ 15 U.S.C. 78f(b)(5).
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    As such, BOX believes the proposed rule change is in the public
interest, and therefore, consistent with the Act.

B. Self-Regulatory Organization's Statement on Burden on Competition

    The proposed rule change would allow the Exchange to remove an
obsolete order type that has been replaced by a more efficient and
functional order type. As such, the Exchange does not believe that the
proposed rule change will impose any burden on competition not
necessary or appropriate in furtherance of the purposes of the Act.

C. Self-Regulatory Organization's Statement on Comments on the Proposed
Rule Change Received From Members, Participants, or Others

    The Exchange has neither solicited nor received comments on the
proposed rule change.

III. Date of Effectiveness of the Proposed Rule Change and Timing for
Commission Action

    The Exchange has filed the proposed rule change pursuant to Section
19(b)(3)(A) of the Act \25\ and Rule 19b-4(f)(6) thereunder.\26\
Because the proposed rule change does not: (i) Significantly affect the
protection of investors or the public interest; (ii) impose any
significant burden on competition; and (iii) become operative prior to
30 days from the date on which it was filed, or such shorter time as
the Commission may designate, if consistent with the protection of
investors and the public interest, the proposed rule change has become
effective pursuant to Section 19(b)(3)(A) of the Act \27\ and Rule 19b-
4(f)(6) thereunder.\28\
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    \25\ 15 U.S.C. 78s(b)(3)(A).
    \26\ 17 CFR 240.19b-4(f)(6).
    \27\ 15 U.S.C. 78s(b)(3)(A).
    \28\ 17 CFR 240.19b-4(f)(6). In addition, Rule 19b-4(f)(6)
requires the Exchange to give the Commission written notice of the
Exchange's intent to file the proposed rule change, along with a
brief description and text of the proposed rule change, at least
five business days prior to the date of filing of the proposed rule
change, or such shorter time as designated by the Commission. The
Exchange has satisfied this requirement.
---------------------------------------------------------------------------

    At any time within 60 days of the filing of such proposed rule
change, the Commission summarily may temporarily suspend such rule
change if it appears to the Commission that such action is necessary or
appropriate in the public interest, for the protection of investors, or
otherwise in furtherance of the purposes of the Act.

IV. Solicitation of Comments

    Interested persons are invited to submit written data, views and
arguments concerning the foregoing, including whether the proposed rule
change is consistent with the Act. Comments may be submitted by any of
the following methods:

Electronic Comments

     Use the Commission's Internet comment form (http://www.sec.gov/rules/sro.shtml ); or
     Send an email to<EMAIL_ADDRESS>Please include
File Number SR-BOX-2014-05 on the subject line.

Paper Comments

     Send paper comments in triplicate to Elizabeth M. Murphy,
Secretary, Securities and Exchange Commission, 100 F Street NE.,
Washington, DC 20549-1090.

All submissions should refer to File Number SR-BOX-2014-05. This file
number should be included on the subject line if email is used. To help
the Commission process and review your comments more efficiently,
please use only one method. The Commission will post all comments on
the Commission's Internet Web site (http://www.sec.gov/rules/sro.shtml
). Copies of the submission, all subsequent amendments, all written
statements with respect to the proposed rule change that are filed with
the Commission, and all written communications relating to the proposed
rule change between the Commission and any person, other than those
that may be withheld from the public in accordance with the provisions
of 5 U.S.C. 552, will be available for Web site viewing and printing in
the Commission's Public Reference Room, 100 F Street NE., Washington,
DC 20549, on official business days between the hours of 10:00 a.m. and
3:00 p.m. Copies of such filing also will be available for inspection
and copying at the principal office of the Exchange. All comments
received will be posted without change; the Commission does not edit
personal identifying information from submissions. You should submit
only information that you wish to make available publicly. All
submissions should refer to File Number SR-BOX-2014-05 and should be
submitted on or before February 19, 2014.

    For the Commission, by the Division of Trading and Markets,
pursuant to delegated authority.\29\
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    \29\ 17 CFR 200.30-3(a)(12).
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Elizabeth M. Murphy,
Secretary.
[FR Doc. 2014-01658 Filed 1-28-14; 8:45 am]
BILLING CODE 8011-01-P


[Federal Register Volume 79, Number 14 (Wednesday, January 22, 2014)]
[Notices]
[Page 3662]
[FR Doc No: 2014-01147]

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DEPARTMENT OF TRANSPORTATION

National Highway Traffic Safety Administration

[Docket No. DOT-NHTSA-2013-0142]

Reports, Forms, and Recordkeeping Requirements

AGENCY: National Highway Traffic Safety Administration (NHTSA), U.S.
Department of Transportation (DOT).

ACTION: Notice and request for comments.

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SUMMARY: The Department of Transportation invites public comments about
our intention to request the Office of Management and Budget (OMB)
approval to renew an information collection. The collection involves
labeling information from manufacturers of brake hoses, end fittings,
and brake hose assemblies. The information to be collected will be used
to and/or is necessary to satisfy the requirements of Federal Motor
Vehicle Safety Standard (FMVSS) No. 106, Brake Hoses. We are required
to publish this notice in the Federal Register by the Paperwork
Reduction Act of 1995, Public Law 104-13.

DATES: Written comments should be submitted by March 24, 2014.

ADDRESSES: You may submit comments [identified by Docket No. DOT-NHTSA-
2013-0142] through one of the following methods:
    Federal eRulemaking Portal: http://www.regulations.gov. Follow the
online instructions for submitting comments.
    Fax: 1-202-493-2251.
    Mail or Hand Delivery: Docket Management Facility, U.S. Department
of Transportation, 1200 New Jersey Avenue SE., West Building, Room W12-
140, Washington, DC 20590, between 9 a.m. and 5 p.m., Monday through
Friday, except on Federal holidays.

FOR FURTHER INFORMATION CONTACT: Joshua Fikentscher, Office of Vehicle
Safety Compliance (NVS-120), National Highway Traffic Safety
Administration, West Building--4th Floor--Room W43-467, 1200 New Jersey
Avenue SE., Washington, DC 20590. Mr. Fikentscher's phone number is
(202) 366-1688.
    Please identify the relevant collection of information by referring
to its OMB Control Number.

SUPPLEMENTARY INFORMATION:
    OMB Control Number: 2127-0052.
    Title: Brake Hose Manufacturers Identification.
    Form Numbers: None.
    Type of Review: Extension of a currently approved information
collection.
    Background: 49 U.S.C. 30101 et seq., as amended (``the Safety
Act''), authorizes NHTSA to issue FMVSSs. The Safety Act mandates that
in issuing any FMVSSs, the agency is to consider whether the standard
is reasonable and appropriate for the particular type of motor vehicle
or item of motor vehicle equipment for which it is prescribed. Using
this authority, FMVSS No. 106, Brake Hoses, was issued. This standard
specifies labeling and performance requirements which apply to all
manufacturers of brake hoses and brake hose end fittings, and to those
who assemble brake hoses. Prior to assembling or selling brake hoses,
these entities must register their identification marks with NHTSA to
comply with the labeling requirements of this standard. In accordance
with the Paperwork Reduction Act, the agency must obtain OMB approval
to continue collecting labeling information. Currently, there are 1,944
manufacturers of brake hoses and end fittings, and brake hose
assemblers, registered with NHTSA. However, only approximately 20
respondents annually request to have their symbol added to or removed
from the NHTSA database. To comply with this standard, each brake hose
manufacturer or assembler must contact NHTSA and state that they want
to be added to or removed from the NHTSA database of registered brake
hose manufacturers. This action is usually initiated by the
manufacturer with a brief written request via U.S. mail, facsimile, an
email message, or a telephone call. Currently, a majority of the
requests are received via U.S. mail and the follow-up paperwork is
conducted via facsimile, U.S. mail, or electronic mail. The estimated
cost for complying with this regulation is $100 per hour. Therefore,
the total annual cost is estimated to be $3,000 (time burden of 30
hours x $100 cost per hour).
    Respondents: Business or other for profit.
    Number of Respondents: 20.
    Number of Responses: 20.
    Total Annual Burden: 30 hours.
    Public Comments Invited: You are asked to comment on any aspect of
this information collection, including (a) Whether the proposed
collection of information is necessary for the Department's
performance; (b) the accuracy of the estimated burden; (c) ways for the
Department to enhance the quality, utility and clarity of the
information collection; and (d) ways that the burden could be minimized
without reducing the quality of the collected information. The agency
will summarize and/or include your comments in the request for OMB's
clearance of this information collection.

    Authority: The Paperwork Reduction Act of 1995; 44 U.S.C.
Chapter 35, as amended; and 49 CFR 1:48.

David Hines,
Director, Office of Crash Avoidance Standards.
[FR Doc. 2014-01147 Filed 1-21-14; 8:45 am]
BILLING CODE 4910-59-P