33472 Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations

rule is not a ‘‘major rule’’ as defined by

5 U.S.C. 804(2).

List of Subjects in 40 CFR Part 180

Environmental protection,

Administrative practice and procedure,

Agricultural commodities, Pesticides

and pests, Reporting and recordkeeping

requirements.

Dated: May 5, 2000.

Peter Caulkins,

Acting Director, Registration Division, Office

of Pesticide Programs.

Therefore, 40 CFR chapter I is

amended as follows:

PART 180—[AMENDED]

1. The authority citation for part 180

continues to read as follows:

Authority: 21 U.S.C. 321(q), 346(a) and

371.

§ 180.176 [Amended]

2. In § 180.176, amend the table in

paragraph (b) by revising the date ‘‘12/

31/99’’ to read ‘‘12/31/01’’.

[FR Doc. 00–12524 Filed 5–23–00; 8:45 am]

BILLING CODE 6560–50–F

ENVIRONMENTAL PROTECTION

AGENCY

40 CFR Part 180

[OPP–300999; FRL–6555–1]

RIN 2070–AB78

Tebufenozide; Benzoic Acid, 3,5-

dimethyl-1-(1,1-dimethylethyl)-2-(4-

ethylbenzoyl) hydrazide; Pesticide

Tolerance

AGENCY: Environmental Protection

Agency (EPA).

ACTION: Final rule.

SUMMARY: This regulation establishes

tolerances for residues of tebufenozide

[benzoic acid, 3,5-dimethyl-1-(1,1-

dimethylethyl)-2-(4-

ethylbenzoyl)hydrazide], in or on the

tree nut crop group (including

pistachios) at 0.1 part per million (ppm)

and on almond hulls at 25 ppm. Rohm

and Haas Company requested this

tolerance under the Federal Food, Drug,

and Cosmetic Act, as amended by the

Food Quality Protection Act of 1996.

DATES: This regulation is effective May

24, 2000. Objections and requests for

hearings, identified by docket control

number OPP–300999, must be received

by EPA on or before July 24, 2000.

ADDRESSES: Written objections and

hearing requests may be submitted by

mail, in person, or by courier. Please

follow the detailed instructions for each

method as provided in Unit VI. of the

‘‘SUPPLEMENTARY INFORMATION.’’

To ensure proper receipt by EPA, your

objections and hearing requests must

identify docket control number OPP–

300999 in the subject line on the first

page of your response.

FOR FURTHER INFORMATION CONTACT: By

mail: Joseph Tavano, Registration

Division (7505C), Office of Pesticide

Programs, Environmental Protection

Agency, Ariel Rios Bldg., 1200

Pennsylvania Ave., NW.,Washington,

DC 20460; telephone number: (703)

305–6411 and e-mail address:

tavano.joseph@epa.gov.

SUPPLEMENTARY INFORMATION:

I. General Information

A. Does This Action Apply to Me?

You may be affected by this action if

you sell, distribute, manufacture, or use

pesticides for agricultural applications,

process food, distribute or sell food, or

implement governmental pesticide

regulations. Potentially affected

categories and entities may include, but

are not limited to:

Categories NAICS

codes

Examples of potentially affected

entities

Industry 111 Crop production

112 Animal production

311 Food manufacturing

32532 Pesticide manufacturing

Agricultural

Stakeholders

Growers/Agricultural Workers,

Contractors

(Certified/Commercial Applicators, Handlers,

Advisors, etc.),

Commercial

Processors,

Pesticide Manufacturers, User

Groups, Food

Consumers

Food DistributorsWholesale Contractors, Retail

Vendors, Commercial Traders/Importers

Inter governmental

Stakeholders

State, Local, and/

or Tribal Government Agencies

Foreign

Entities

Governments,

Growers, Trade

Groups, Exporters

Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations 33473

This listing is not intended to be

exhaustive, but rather provides a guide

for readers regarding entities likely to be

affected by this action. Other types of

entities not listed in the table could also

be affected. The North American

Industrial Classification System

(NAICS) codes have been provided to

assist you and others in determining

whether or not this action might apply

to certain entities. If you have questions

regarding the applicability of this action

to a particular entity, consult the person

listed under ‘‘FOR FURTHER

INFORMATION CONTACT.’’

B. How Can I Get Additional

Information, Including Copies of this

Document and Other Related

Documents?

1. Electronically. You may obtain

electronic copies of this document, and

certain other related documents that

might be available electronically, from

the EPA Internet Home Page at http://

www.epa.gov/. To access this

document, on the Home Page select

‘‘Laws and Regulations’’ and then look

up the entry for this document under

the ‘‘Federal Register—Environmental

Documents.’’ You can also go directly to

the Federal Register listings at http://

www.epa.gov/fedrgstr/.

2. In person. The Agency has

established an official record for this

action under docket control number

OPP–300999. The official record

consists of the documents specifically

referenced in this action, and other

information related to this action,

including any information claimed as

Confidential Business Information (CBI).

This official record includes the

documents that are physically located in

the docket, as well as the documents

that are referenced in those documents.

The public version of the official record

does not include any information

claimed as CBI. The public version of

the official record, which includes

printed, paper versions of any electronic

comments submitted during an

applicable comment period is available

for inspection in the Public Information

and Records Integrity Branch (PIRIB),

Rm. 119, Crystal Mall #2, 1921 Jefferson

Davis Hwy., Arlington, VA, from 8:30

a.m. to 4 p.m., Monday through Friday,

excluding legal holidays. The PIRIB

telephone number is (703) 305–5805.

II. Background and Statutory Findings

In the Federal Register of August 19,

1998 (63 FR 44439) (FRL 6019–6), and

February 17, 1999 (64 FR 7883) (FRL

6060–1), EPA issued a notice pursuant

to section 408 of the Federal Food, Drug,

and Cosmetic Act (FFDCA), 21 U.S.C.

346a as amended by the Food Quality

Protection Act of 1996 (FQPA) (Public

Law 104–170) announcing the filing of

a pesticide petition (PP) 7F4815 for a

tolerance by Rohm and Haas Company,

100 Independence Mall West,

Philadelphia, 19106–2399. This notice

included a summary of the petition

prepared by Rohm and Haas Company,

the registrant. There were no comments

received in response to the notice of

filing.

The petition requested that 40 CFR

180.482 be amended by establishing

tolerances for residues of the insecticide

tebufenozide in or on the tree nut crop

group (including pistachios) at 0.1 ppm

and on almond hulls at 25 ppm.

Section 408(b)(2)(A)(i) of the FFDCA

allows EPA to establish tolerances (the

legal limit for a pesticide chemical

residue in or on a food) only if EPA

determines that the tolerance is ‘‘safe.’’

Section 408(b)(2)(A)(ii) defines ‘‘safe’’ to

mean that ‘‘there is a reasonable

certainty that no harm will result from

aggregate exposure to the pesticide

chemical residue, including all

anticipated dietary exposures and all

other exposures for which there is

reliable information.’’ This includes

exposure through food and drinking

water and in residential settings, but

does not include occupational exposure.

Section 408(b)(2)(C) requires EPA to

give special consideration to exposure

of infants and children to the pesticide

chemical residue in establishing a

tolerance and to ‘‘ensure that there is a

reasonable certainty that no harm will

result to infants and children from

aggregate exposure to the pesticide

chemical residue * * *.’’

EPA performs a number of analyses to

determine the risks from aggregate

exposure to pesticide residues. For

further discussion of the regulatory

requirements of section 408 and a

complete description of the risk

assessment process, see the final rule on

Bifenthrin Pesticide Tolerances (62 FR

62961, November 26, 1997) (FRL–5754–

7).

III. Aggregate Risk Assessment and

Determination of Safety

Consistent with section 408(b)(2)(D),

EPA has reviewed the available

scientific data and other relevant

information in support of this action.

EPA has sufficient data to assess the

hazards of and to make a determination

on aggregate exposure, consistent with

section 408(b)(2), for tolerances for

residues of tebufenozide on the tree nut

crop group (including pistachios) at 0.1

ppm and on almond hulls at 25 ppm.

EPA’s assessment of the exposures and

risks associated with establishing the

tolerance follows.

A. Toxicological Profile

EPA has evaluated the available

toxicity data and considered its validity,

completeness, and reliability as well as

the relationship of the results of the

studies to human risk. EPA has also

considered available information

concerning the variability of the

sensitivities of major identifiable

subgroups of consumers, including

infants and children. The nature of the

toxic effects caused by tebufenozide are

discussed in this unit.

B. Toxicological Endpoints

1. Acute toxicity— i. Acute toxicity

studies with technical grade: Oral LD50

in the rat is > 5 grams for males and

females—Toxicity Category IV; dermal

LD50 in the rat is = 5,000 milligrams/

kilogram (mg/kg) for males and

females—Toxicity Category III;

inhalation LC50 in the rat is >4.5

milligram/Liter (mg/L) - Toxicity

Category III; primary eye irritation study

in the rabbit is a non-irritant; primary

skin irritation in the rabbit >5 mg/kg—

Toxicity Category IV. Tebufenozide is

not a sensitizer.

ii. In a 21–day dermal toxicity study,

Crl:CD rats (6/sex/dose) received

repeated dermal administration of either

the technical (96.1%) product (RH–

75,992) at 1,000 (mg/kg/day) (LimitDose) or the formulation (23.1% active

ingredient (a.i.)) product (RH–755,992

2F) at 0, 62.5, 250, or 1,000 milligram/

kilogram/day (mg/kg/day), 6 hours/day,

5 days/week for 21 days. Under

conditions of this study, RH–75,992

Technical or RH–75,992 2F

demonstrated no systemic toxicity or

dermal irritation at the highest dose

tested (HDT) 1,000 mg/kg during the

21–day study. Based on these results,

the no-observed adverse effect level

(NOAEL) for systemic toxicity and

dermal irritation in both sexes is 1,000

mg/kg/day HDT. A lowest-observed

33474 Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations

adverse effect level (LOAEL) for

systemic toxicity and dermal irritation

was not established.

iii. A 1–year dog feeding study with

a LOAEL of 250 ppm (9 mg/kg/day for

male and female dogs) based on

decreases in RBC, HCT, and HGB,

increases in Heinz bodies,

methemoglobin, MCV, MCH,

reticulocytes, platelets, plasma total

bilirubin, spleen weight, and spleen/

body weight ratio, and liver/body

weight ratio. Hematopoiesis and

sinusoidal engorgement occurred in the

spleen, and hyperplasia occurred in the

marrow of the femur and sternum. The

liver showed an increased pigment in

the Kupffer cells. The NOAEL for

systemic toxicity in both sexes is 50

ppm (1.9 mg/kg/day).

iv. An 18–month mouse

carcinogenicity study with no

carcinogenicity observed at dosage

levels up to and including 1,000 ppm.

v. A 2–year rat carcinogenicity study

with no carcinogenicity observed at

dosage levels up to and including 2,000

ppm (97 mg/kg/day and 125 mg/kg/day

for males and females, respectively)

vi. In a prenatal developmental

toxicity study in Sprague-Dawley rats

(25/group), tebufenozide was

administered on gestation days 6–15 by

gavage in aqueous methyl cellulose at

dose levels of 50, 250, or 1,000 mg/kg/

day and a dose volume of 10 ml/kg.

There was no evidence of maternal or

developmental toxicity; the maternal

and developmental toxicity NOAEL was

1,000 mg/kg/day.

vii. In a prenatal developmental

toxicity study conducted in New

Zealand white rabbits (20/group),

tebufenozide was administered in 5 ml/

kg of aqueous methyl cellulose at gavage

doses of 50, 250, or 1,000 mg/kg/day on

gestation days 7–19. No evidence of

maternal or developmental toxicity was

observed; the maternal and

developmental toxicity NOAEL was

1,000 mg/kg/day.

viii. In a 1993 2-generation

reproduction study in Sprague-Dawley

rats, tebufenozide was administered at

dietary concentrations of 0, 10, 150, or

1,000 ppm (0, 0.8, 11.5, or 154.8 mg/kg/

day for males and 0, 0.9, 12.8, or 171.1

mg/kg/day for females). The parental

systemic NOAEL was 10 ppm (0.8/0.9

mg/kg/day for males and females,

respectively) and the LOAEL was 150

ppm (11.5/12.8 mg/kg/day for males and

females, respectively) based on

decreased body weight, body weight

gain, and food consumption in males,

and increased incidence and/or severity

of splenic pigmentation. In addition,

there was an increased incidence and

severity of extramedullary

hematopoiesis at 2,000 ppm. The

reproductive NOAEL was 150 ppm.

(11.5/12.8 mg/kg/day for males and

females, respectively) and the LOAEL

was 2,000 ppm (154.8/171.1 mg/kg/day

for males and females, respectively)

based on an increase in the number of

pregnant females with increased

gestation duration and dystopia. Effects

in the offspring consisted of decreased

number of pups per litter on postnatal

days 0 and/or 4 at 2,000 ppm (154.8/

171.1 mg/kg/day for males and females,

respectively) with a NOAEL of 150 ppm

(11.5/12.8 mg/kg/day for males and

females, respectively).

ix. In a 1995 2-generation

reproduction study in rats, tebufenozide

was administered at dietary

concentrations of 0, 25, 200, or 2,000

ppm (0, 1.6, 12.6, or 126.0 mg/kg/day

for males and 0, 1.8, 14.6, or 143.2 mg/

kg/day for females). For parental

systemic toxicity, the NOAEL was 25

ppm (1.6/1.8 mg/kg/day in males and

females, respectively), and the LOAEL

was 200 ppm (12.6/14.6 mg/kg/day in

males and females), based on

histopathological findings (congestion

and extramedullary hematopoiesis) in

the spleen. Additionally, at 2,000 ppm

(126.0/143.2 mg/kg/day in M/F),

treatment-related findings included

reduced parental body weight gain and

increased incidence of hemosiderinladen cells in the spleen. Columnar

changes in the vaginal squamous

epithelium and reduced uterine and

ovarian weights were also observed at

2,000 ppm, but the toxicological

significance was unknown. For

offspring, the systemic NOAEL was 200

ppm (12.6/14.6 mg/kg/day in males and

females), and the LOAEL was 2,000

ppm (126.0/143.2 mg/kg/day in M/F)

based on decreased body weight on

postnatal days 14 and 21.

x. Several mutagenicity tests which

were all negative. These include an

Ames assay with and without metabolic

activation, an in vivo cytogenetic assay

in rat bone marrow cells, and in vitro

chromosome aberration assay in CHO

cells, a CHO/HGPRT assay, a reverse

mutation assay with E. Coli, and an

unscheduled DNA synthesis assay

(UDS) in rat hepatocytes.

xi. The pharmacokinetics and

metabolism of tebufenozide were

studied in female Sprague-Dawley rats

(3–6/sex/group) receiving a single oral

dose of 3 or 250 mg/kg of RH–5992, 14C

labeled in one of three positions (A-ring,

B-ring or N-butylcarbon). The extent of

absorption was not established. The

majority of the radio labeled material

was eliminated or excreted in the feces

within 48 hours; small amounts (1 to

7% of the administered dose) were

excreted in the urine and only traces

were excreted in expired air or

remained in the tissues. There was no

tendency for bioaccumulation.

Absorption and excretion were rapid. A

total of 11 metabolites, in addition to

the parent compound, were identified in

the feces; the parent compound

accounted for 96 to 99% of the

administered radioactivity in the high

dose group and 35 to 43% in the low

dose group. No parent compound was

found in the urine; urinary metabolites

were not characterized. The identity of

several fecal metabolites was confirmed

by mass spectral analysis and other fecal

metabolites were tentatively identified

by cochromatography with synthetic

standards. A pathway of metabolism

was proposed based on these data.

Metabolism proceeded primarily by

oxidation of the three benzyl carbons,

two methyl groups on the B-ring and an

ethyl group on the A-ring to alcohols,

aldehydes or acids. The type of

metabolite produced varies depending

on the position oxidized and extent of

oxidation. The butyl group on the

quaternary nitrogen also can be cleaved

(minor), but there was no fragmentation

of the molecule between the benzyl

rings.

No qualitative differences in

metabolism were observed between

sexes, when high or low dose groups

were compared or when different

labeled versions of the molecule were

compared.

xii. The absorption and metabolism of

tebufenozide were studied in a group of

males and female bile-duct cannulated

rats. Over a 72–hour period, biliary

excretion accounted for 30% females to

34% males of the administered dose

while urinary excretion accounted for

ù55% of the administered dose and the

carcass accounted for <0.5% of the

administered dose for both males and

females. Thus, systemic absorption

(percent of dose recovered in the bile,

urine and carcass) was 35% females to

39% males. The majority of the

radioactivity in the bile (20% females to

24% males of the administered dose)

was excreted within the first 6 hours

postdosing indicating rapid absorption.

Furthermore, urinary excretion of the

metabolites was essentially complete

within 24 hours postdosing. A large

amount (67% males to 70% females) of

the administered dose was unabsorbed

and excreted in the feces by 72 hours.

Total recovery of radioactivity was

105% of the administered dose.

A total of 13 metabolites were

identified in the bile; the parent

compound was not identified (i.e. -

unabsorbed compound) nor were the

primary oxidation products seen in the

Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations 33475

feces in the pharmacokinetics study.

The proposed metabolic pathway

proceeded by primary oxidation of the

benzylic carbons to alcohols, aldehydes

or acids. Bile contained most of the

other highly oxidized products found in

the feces. The most significant

individual bile metabolites accounted

for 5% to 18% of the total radioactivity

(males and/or females). Bile also

contained the previously undetected (in

the pharmacokinetics study) ‘‘A’’ Ring

ketone and the ‘‘B’’ Ring diol. The other

major components were characterized as

high molecular weight conjugates. No

individual bile metabolite accounted for

>5% of the total administered dose.

Total bile radioactivity accounted for

≈17% of the total administered dose. No

major qualitative differences in biliary

metabolites were observed between

sexes. The metabolic profile in the bile

was similar to the metabolic profile in

the feces and urine.

2. Short- and intermediate-term

toxicity. No dermal or systemic toxicity

was seen in rats receiving 15 repeated

dermal applications of the technical

(97.2%) product at 1,000 mg/kg/day

(Limit-Dose) as well as a formulated

(23% active ingredient (a.i)) product at

0, 62.5, 250, or 1,000 mg/kg/day over a

21–day period. The Agency noted that

in spite of the hematological effects seen

in the dog study, similar effects were

not seen in the rats receiving the

compound via the dermal route

indicating poor dermal absorption. Also,

no developmental endpoints of concern

were evident due to the lack of

developmental toxicity in either rat or

rabbit studies. This risk is considered to

be negligible.

3. Chronic toxicity. EPA has

established the chronic population

adjusted dose (cPAD) for tebufenozide

at 0.018 mg/kg/day. This reference dose

(RfD) is based on a NOAEL of 1.8 mg/

kg/day and an uncertainty factor (UF) of

100. The NOAEL was established from

the chronic toxicity study in dogs where

the NOAEL was 1.8 mg/kg/day based on

growth retardation, alterations in

hematology parameters, changes in

organ weights, and histopathological

lesions in the bone, spleen and liver at

8.7 mg/kg/day. EPA determined that the

10x factor to protect children and

infants (as required by FQPA) should be

reduced to 1x. Therefore, the cPAD is

the same as the RfD: 0.018 mg/kg/day.

4. Carcinogenicity. Tebufenozide has

been classified as a Group E, ‘‘no

evidence of carcinogenicity for

humans,’’ chemical by EPA.

C. Exposures and Risks

1. Dietary— i. From food and feed

uses. Tolerances have been established

(40 CFR 180.482) for the residues of

tebufenozide, in or on a variety of raw

agricultural commodities. In today’s

action tolerances will be established for

the residues of tebufenozide in or on the

tree nut crop group including pistachios

at 0.1 ppm, and on almond hulls at 25.0

ppm. Risk assessments were conducted

by EPA to assess dietary exposures from

tebufenozide as follows:

Section 408(b)(2)(F) states that the

Agency may use data on the actual

percent of food treated for assessing

chronic dietary risk only if the Agency

can make the following findings:

Condition 1, that the data used are

reliable and provide a valid basis to

show what percentage of the food

derived from such crop is likely to

contain such pesticide residue;

Condition 2, that the exposure estimate

does not under estimate exposure for

any significant subpopulation group;

and Condition 3, if data are available on

pesticide use and food consumption in

a particular area, the exposure estimate

does not understate exposure for the

population in such area. In addition, the

Agency must provide for periodic

evaluation of any estimates used. To

provide for the periodic evaluation of

the estimate of percent crop treated

(PCT) as required by section

408(b)(2)(F), EPA may require

registrants to submit data on PCT.

a. Acute exposure and risk. Acute

dietary risk assessments are performed

for a food-use pesticide if a toxicological

study has indicated the possibility of an

effect of concern occurring as a result of

a 1-day or single exposure. Neither

neurotoxicity nor systemic toxicity was

observed in rats given a single oral

administration of tebufenozide at 0, 500,

1,000 or 2,000 mg/kg. No maternal or

developmental toxicity was observed

following oral administration of

tebufenozide at 1,000 mg/kg/day (LimitDose) during gestation to pregnant

rabbits. This risk is considered to be

negligible.

b. Chronic exposure and risk. In

conducting the DEEM (Dietary Exposure

Evaluation Model) analysis for chronic

exposure to and risk from tebufenozide

residues in food, the Agency used

tolerance level residues and some PCT

(Tier 2). For the subject crops, the

tolerances used are: 0.1 ppm for tree

nuts (including pistachios) and 25.0

ppm for almond hulls. The analysis

evaluates individual food consumption

as reported by respondents in the

USDA, Continuing Surveys of Food

Intake by Individuals conducted in 1989

through 1992. Summaries of the

exposures and their representations as

percentages of the cPAD for the general

population and subgroups of interest are

presented in Table 1.

TABLE 1. CHRONIC EXPOSURE ANALYSIS BY THE DEEM SYSTEM FOR

TEBUFENOZIDE

Population subgroup

Exposure

(mg/kg/

day)

cPAD%

U.S. population (48

continguous

states).

0.0026 14%

Non-nursing infants

(<1 years old).

0.0097 54%

Females (13+/nursing).0.0024 13%

In the table, ‘‘cPAD%’’ means cPAD%

= Exposure x 100% divide by cPAD.

The subgroups listed above are: (1)

The U.S. population (48 continguous

states ); (2) highest exposed population

subgroup that includes infants and

children; and (3) females 13+.

This chronic dietary (food only) risk

assessment should be viewed as

conservative. Further refinement using

anticipated residue values and

additional PCT information would

result in a lower estimate of chronic

dietary exposure from food.

The estimates of PCT were used as

follows. In all cases the maximum

estimates were used.

Crop Average Maximum

Almonds ................ <1% ........ <1%

Apples ................... 1% .......... 2%

Beans/Peas, Dry .. 0% .......... 1%

Cabbage, Fresh .... 2% .......... 3%

Cole Crops ........... 1% .......... 2%

Cotton ................... 1% .......... 4%

Spinach, Fresh ..... 2% .......... 3%

Spinach, Processed.20% ........ 29%

Sugarcane ............ 3% .......... 5%

Walnuts ................. 10% ........ 16%

ii. From drinking water— a. Acute

exposure and risk. Because no acute

dietary endpoint was determined, the

Agency concludes that there is a

reasonable certainty of no harm from

acute exposure from drinking water.

b.Chronic exposure and risk. The

Agency calculated the Tier I Estimated

Environmental Concentrations (EECs)

for tebufenozide using generic expected

environmental concentration (GENEEC)

(surface water) and screening

concentration in ground water (SCI–

GROW) (ground water) models for use

in the human health risk assessment.

For chronic exposure, the worst case

EECs for surface water and ground water

33476 Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations

were 16.5 parts per billion (ppb) and

1.04 ppb, respectively. These values

represent upper-bound estimates of the

concentrations that might be found in

surface and ground water. These

modeling data were compared to the

chronic drinking water levels of

comparison (DWLOC) for tebufenozide

in ground and surface water (SOP for

Drinking Water Exposure and Risk

Assessments, November 20, 1997).

For purposes of chronic risk

assessment, the estimated maximum

concentration for tebufenozide in

surface and ground waters (16.5

ppb=16.5 μg/L) was compared to the

back-calculated human health DWLOCs

for the chronic (non-cancer) endpoint.

These DWLOCs for various population

categories are summarized in Table 2.

TABLE 2. DRINKING WATER LEVELS OF COMPARISON FOR CHRONIC EXPOSURE TO TEBUFENOZIDE1

Population Category2 Chronic RfD

(mg/kg/day)

Food exposure

(mg/kg/day)

Max. water

exposure3

(mg/kg/day)

DWLOC 4,5,6

(μg/L)

EEC7 calc.

max. (μg/L)

U.S. population (48 continguous states) ................................................. 0.018 0.0026 0.0154 540 16.5

Females (13+ years) ................................................................................ 0.018 0.0024 0.0156 470 16.5

Non-nursing infants (<1 year) .................................................................. 0.018 0.0097 0.0083 83 16.5

1Values are expressed to 2 significant figures.

2Within each of these categories, the subgroup with the highest food exposure was selected.

3Maximum water exposure (chronic) (mg/kg/day) = Chronic PAD (mg/kg/day)—Food exposure (mg/kg/day).

4DWLOC(μg/L) = Max. water exposure (mg/kg/day) x body wt (kg) ÷ [(10-3 mg/μg) x water consumed daily (L/day)]. 5HED Default body weights are: General U.S. population, 70 kg; females (13+ years old), 60 kg; other adult populations, 70 kg; and, all infants/children, 10 kg. 6HED Default daily drinking rates are 2 L/day for adults and 1 L/day for children.

7EEC: Estimated Environmental Concentration. (Chronic 56-day value).

2. From non-dietary exposure. There

is a potential for occupational exposure

to tebufenozide during mixing, loading,

and application activities. However, the

Agency did not identify dermal or

inhalation endpoints for tebufenozide

and determined that risks from these

routes of exposure are negligible.

3. Cumulative exposure to substances

with a common mechanism of toxicity.

Section 408(b)(2)(D)(v) requires that,

when considering whether to establish,

modify, or revoke a tolerance, the

Agency consider ‘‘available

information’’ concerning the cumulative

effects of a particular pesticide’s

residues and ‘‘other substances that

have a common mechanism of toxicity.’’

EPA does not have, at this time,

available data to determine whether

tebufenozide has a common mechanism

of toxicity with other substances or how

to include this pesticide in a cumulative

risk assessment. Unlike other pesticides

for which EPA has followed a

cumulative risk approach based on a

common mechanism of toxicity,

tebufenozide does not appear to

produce a toxic metabolite produced by

other substances. For the purposes of

this tolerance action, therefore, EPA has

not assumed that tebufenozide has a

common mechanism of toxicity with

other substances. For information

regarding EPA’s efforts to determine

which chemicals have a common

mechanism of toxicity and to evaluate

the cumulative effects of such

chemicals, see the final rule for

Bifenthrin Pesticide Tolerances (62 FR

62961, November 26, 1997).

D. Aggregate Risks and Determination of

Safety for U.S. Population

1. Acute risk. The Agency did not

identify an acute dietary toxicological

endpoint, therefore, the risk from this

route of exposure is negligible.

2. Chronic risk. Using the exposure

assumptions described above, and

taking into account the completeness

and reliability of the toxicity data, the

Agency has concluded that dietary (food

only) exposure to tebufenozide will

utilize 14% of the cPAD for the U.S.

population, and 54% of the cPAD for

the most highly exposed population

subgroup (non- nursing infants <1 yr).

EPA generally has no concern for

exposures below 100% of the cPAD.

Submitted environmental fate studies

suggest that tebufenozide is moderately

persistent to persistent and mobile;

thus, tebufenozide could potentially

leach to ground water and runoff to

surface water under certain

environmental conditions. The

modeling data for tebufenozide indicate

levels less than the Agency’s DWLOCs.

There are no chronic non- occupational/

residential exposures expected for

tebufenozide. Therefore, the Agency

concludes that there is a reasonable

certainty that no harm will result to

adults, infants and children from

chronic aggregate exposure to

tebufenozide residues.

3. Short- and intermediate-term risk.

There are potential non-occupational/

residential short-term post application

exposures (incidental non-dietary

ingestion) to toddlers from the use of

tebufenozide on ornamentals. However,

since the Agency did not identify acute

dietary endpoint, the short-term post

application exposure risk assessment is

expected to be negligible. Intermediateterm incidental non-dietary exposures

are not expected.

4. Determination of safety. Based on

these risk assessments, EPA concludes

that there is a reasonable certainty that

no harm will result from aggregate

exposure to tebufenozide residues.

E. Aggregate Risks and Determination of

Safety for Infants and Children

1. Safety factor for infants and

children. In assessing the potential for

additional sensitivity of infants and

children to residues of tebufenozide,

EPA considered data from

developmental toxicity studies in the rat

and rabbit and a 2-generation

reproduction study in the rat. The

developmental toxicity studies are

designed to evaluate adverse effects on

the developing organism resulting from

maternal pesticide exposure gestation.

Reproduction studies provide

information relating to effects from

exposure to the pesticide on the

reproductive capability of mating

animals and data on systemic toxicity.

FFDCA section 408 provides that EPA

shall apply an additional tenfold margin

of safety for infants and children in the

case of threshold effects to account for

prenatal and postnatal toxicity and the

completeness of the data base unless

EPA determines that a different margin

of safety will be safe for infants and

children. Margins of safety are

incorporated into EPA risk assessments

either directly through use of a margin

of exposure (MOE) analysis or through

using uncertainty (safety) factors in

calculating a dose level that poses no

appreciable risk to humans. EPA

Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations 33477

believes that reliable data support using

the standard uncertainty factor (usually

100 for combined interspecies and

intraspecies variability) and not the

additional tenfold MOE/uncertainty

factor when EPA has a complete data

base under existing guidelines and

when the severity of the effect in infants

or children or the potency or unusual

toxic properties of a compound do not

raise concerns regarding the adequacy of

the standard MOE/safety factor.

2. Conclusion. There is a complete

toxicity data base for tebufenozide and

exposure data are complete or are

estimated based on data that reasonably

accounts for potential exposures. For

the reasons summarized above, the

Agency concludes that an additional

safety factor is not needed to protect the

safety of infants and children.

3. Acute risk. Since no acute

toxicological endpoints were

established, it is unlikely that acute

aggregate risk exists.

4. Chronic risk. Using the exposure

assumptions described above, and

taking into account the completeness

and reliability of the toxicity data, the

Agency has concluded that dietary (food

only) exposure to tebufenozide will

utilize 14% of the cPAD for the U.S.

population, and 54% of the cPAD for

the most highly exposed population

subgroup (non-nursing infants <1 yr).

EPA generally has no concern for

exposures below 100% of the cPAD.

Despite the potential for exposure to

tebufenozide in drinking water and from

non-dietary, non- occupational

exposure, EPA does not expect the

aggregate exposure to exceed 100% of

the RfD.

5. Short- or intermediate-term risk.

Short- and intermediate-term risks are

judged to be negligible due to the lack

of significant toxicological effects

observed.

6. Determination of safety. Based on

these risk assessments, EPA concludes

that there is a reasonable certainty that

no harm will result to infants and

children from aggregate exposure to

tebufenozide residues.

IV. Other Considerations

A. Metabolism in Plants and Animals

1. Nature of the residue—Plants. The

qualitative nature of the residue in

plants is adequately understood based

upon acceptable apple, sugar beet, and

rice metabolism studies. The Agency

has concluded that the residue of

regulatory concern is tebufenozide per

se.

2. Nature of the residue—Animal. The

results of the ruminant and poultry

metabolism studies have been reviewed

by the Agency and the determination

was made that the tebufenozide residues

of regulatory concern in animals are the

parent tebufenozide and the four

metabolites designated: RH–2703

[benzoic acid, 3,5-dimethyl-1-(1,1-

dimethylethyl)-2-((4-

carboxymethyl)benzoyl)hydrazide], RH–

9886 [benzoic acid, 3-hydroxymethyl,5-

methyl-1-(1,1-dimethylethyl)-2-(4-

ethylbenzoyl)hydrazide], the stearic

acid conjugate of RH–9886, and RH–

0282 [benzoic acid, 3-hydroxymethyl-5-

methyl-1-(1,1- dimethylethyl)-2-(4-(1-

hydroxyethyl) benzoyl)hydrazide].

B. Analytical Enforcement Methodology

1. Analytical methods—Plant tissues.

The Rohm and Haas method TR 34–95–

20, with minor modifications, was used

to determine tebufenozide residue levels

in/on pecans and almonds (MRID

44414304). This method has been

validated by EPA and was submitted to

the Food and Drug Administration

(FDA) for inclusion in PAM II. The

method limit of quantitation (LOQ) and

limit of detection (LOD) for

tebufenozide are 0.01 ppm and 0.003

ppm, respectively.

2. Analytical methods—Animal

tissues. A submitted HPLC/UV Method,

Rohm and Haas Method TR 34–96–109,

has been determined to be adequate for

collecting data on residues of

tebufenozide in animal tissues. The

validated LOQ for tebufenozide in

animal tissue is 0.02 ppm. The LOQ for

each of the metabolites studied are as

follows: RH–2703 in liver, 0.02 ppm;

RH–9886 and RH–0282 in meat, 0.02

ppm; RH–9526 in fat, 0.02 ppm. The

LODs for the analytes are 0.006 ppm in

tissues.

3. Multi-residue methods. Rohm and

Haas has previously submitted data

involving multi-residue method testing.

Adequate enforcement methodology

(example—gas chromatography) is

available to enforce the tolerance

expression. The method may be

requested from: Calvin Furlow, PRRIB,

IRSD (7502C), Office of Pesticide

Programs, Environmental Protection

Agency, Ariel Rios Bldg., 1200

Pennsylvania Ave., NW., Washington,

DC 20460; telephone number: (703)

305–5229; e-mail address:

furlow.calvin@epa.gov.

C. Magnitude of Residues

1. The petitioner submitted data from

tests on pecans, almonds, and almond

hulls. A bridging study was also

submitted showing that there were no

differences in the amount of RH–5992

residues on pecans (nutmeat) from the

two formulations. Residues of

tebufenozide were determined in/on

nuts harvested 11–14 days following the

last of 4 foliar applications of

tebufenozide for a total of ∼2.0 lbs ai/

acre per season (1x the proposed

seasonal rate). Tebufenozide residues

in/on pecans were below the LOQ of

0.01 ppm: values ranged from <0.003

ppm (the LOD) to 0.0058 ppm.

Tebufenozide residues in/on almonds

were < 0.003–0.052 ppm, and in/on

almond hulls were 7.880–19.9 ppm.

2. The inclusion of pistachios into the

tree nut crop group without a change in

the representative crops, pecans and

almonds, has been recommended but

has not as yet been published. The

submitted pecan, almond, and almond

hull field trial residue studies are

adequate to support the proposed 0.1

ppm tolerance for the tree nut crop

group including pistachios and the 25.0

ppm tolerance for almond hulls.

3. Processed food/feed. There are no

tree nut (including pistachio) processed

commodities of regulatory interest.

D. International Residue Limits

Codex MRLs have been established

for residues of tebufenozide in/on pome

fruit (1.0 ppm), husked rice (0.1 ppm)

and walnuts (0.05 ppm). Tebufenozide

is registered in Canada, and a tolerance

for residues in/on apples is established

at 1.0 ppm. EPA has set the pome fruit

tolerance at 1.0 ppm to harmonize with

the Codex and Canadian levels.

E. Rotational Crop Restrictions

Since tree nuts and pistachios are

perennial crops, rotational crop

restrictions are not required for the tree

nut crop group and pistachios.

V. Conclusion

Therefore, the tolerances are

established for residues of tebufenozide,

in or on the tree nut crop group

(including pistachios) at 0.1 ppm, and

on almond hulls at 25 ppm.

VI. Objections and Hearing Requests

Under section 408(g) of the FFDCA, as

amended by the FQPA, any person may

file an objection to any aspect of this

regulation and may also request a

hearing on those objections. The EPA

procedural regulations which govern the

submission of objections and requests

for hearings appear in 40 CFR part 178.

Although the procedures in those

regulations require some modification to

reflect the amendments made to the

FFDCA by the FQPA of 1996, EPA will

continue to use those procedures, with

appropriate adjustments, until the

necessary modifications can be made.

The new section 408(g) provides

essentially the same process for persons

to ‘‘object’’ to a regulation for an

33478 Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations

exemption from the requirement of a

tolerance issued by EPA under new

section 408(d), as was provided in the

old FFDCA sections 408 and 409.

However, the period for filing objections

is now 60 days, rather than 30 days.

A. What Do I Need to Do To File an

Objection or Request a Hearing?

You must file your objection or

request a hearing on this regulation in

accordance with the instructions

provided in this unit and in 40 CFR part

178. To ensure proper receipt by EPA,

you must identify docket control

number OPP–300999 in the subject line

on the first page of your submission. All

requests must be in writing, and must be

mailed or delivered to the Hearing Clerk

on or before July 24, 2000.

1. Filing the request. Your objection

must specify the specific provisions in

the regulation that you object to, and the

grounds for the objections (40 CFR

178.25). If a hearing is requested, the

objections must include a statement of

the factual issue(s) on which a hearing

is requested, the requestor’s contentions

on such issues, and a summary of any

evidence relied upon by the objector (40

CFR 178.27). Information submitted in

connection with an objection or hearing

request may be claimed confidential by

marking any part or all of that

information as CBI. Information so

marked will not be disclosed except in

accordance with procedures set forth in

40 CFR part 2. A copy of the

information that does not contain CBI

must be submitted for inclusion in the

public record. Information not marked

confidential may be disclosed publicly

by EPA without prior notice.

Mail your written request to: Office of

the Hearing Clerk (1900), Environmental

Protection Agency, Ariel Rios Bldg.,

1200 Pennsylvania Ave., NW.,

Washington, DC 20460. You may also

deliver your request to the Office of the

Hearing Clerk in Rm. C400, Waterside

Mall, 401 M St., SW., Washington, DC

20460. The Office of the Hearing Clerk

is open from 8 a.m. to 4 p.m., Monday

through Friday, excluding legal

holidays. The telephone number for the

Office of the Hearing Clerk is (202) 260–

4865.

2. Tolerance fee payment. If you file

an objection or request a hearing, you

must also pay the fee prescribed by 40

CFR 180.33(i) or request a waiver of that

fee pursuant to 40 CFR 180.33(m). You

must mail the fee to: EPA Headquarters

Accounting Operations Branch, Office

of Pesticide Programs, P.O. Box

360277M, Pittsburgh, PA 15251. Please

identify the fee submission by labeling

it ‘‘Tolerance Petition Fees.’’

EPA is authorized to waive any fee

requirement ‘‘when in the judgement of

the Administrator such a waiver or

refund is equitable and not contrary to

the purpose of this subsection.’’ For

additional information regarding the

waiver of these fees, you may contact

James Tompkins by phone at (703) 305–

5697, by e-mail at

tompkins.jim@epa.gov, or by mailing a

request for information to Mr. Tompkins

at Registration Division (7505C), Office

of Pesticide Programs, Environmental

Protection Agency, Ariel Rios Bldg.,

1200 Pennsylvania Ave., NW.,

Washington, DC 20460.

If you would like to request a waiver

of the tolerance objection fees, you must

mail your request for such a waiver to:

James Hollins, Information Resources

and Services Division (7502C), Office of

Pesticide Programs, Environmental

Protection Agency, Ariel Rios Bldg.,

1200 Pennsylvania Ave., NW.,

Washington, DC 20460.

3. Copies for the Docket. In addition

to filing an objection or hearing request

with the Hearing Clerk as described in

Unit VI.A., you should also send a copy

of your request to the PIRIB for its

inclusion in the official record that is

described in Unit I.B.2. Mail your

copies, identified by docket control

number OPP–300999, to: Public

Information and Records Integrity

Branch, Information Resources and

Services Division (7502C), Office of

Pesticide Programs, Environmental

Protection Agency, Ariel Rios Bldg.,

1200 Pennsylvania Ave., NW.,

Washington, DC 20460. In person or by

courier, bring a copy to the location of

the PIRIB described in Unit I.B.2. You

may also send an electronic copy of

your request via e-mail to: oppdocket@epa.gov. Please use an ASCII

file format and avoid the use of special

characters and any form of encryption.

Copies of electronic objections and

hearing requests will also be accepted

on disks in WordPerfect 6.1/8.0 file

format or ASCII file format. Do not

include any CBI in your electronic copy.

You may also submit an electronic copy

of your request at many Federal

Depository Libraries.

B. When Will the Agency Grant a

Request for a Hearing?

A request for a hearing will be granted

if the Administrator determines that the

material submitted shows the following:

There is a genuine and substantial issue

of fact; there is a reasonable possibility

that available evidence identified by the

requestor would, if established resolve

one or more of such issues in favor of

the requestor, taking into account

uncontested claims or facts to the

contrary; and resolution of the factual

issue(s) in the manner sought by the

requestor would be adequate to justify

the action requested (40 CFR 178.32).

VII. Regulatory Assessment

Requirements

This final rule establishes a tolerance

under FFDCA section 408(d) in

response to a petition submitted to the

Agency. The Office of Management and

Budget (OMB) has exempted these types

of actions from review under Executive

Order 12866, entitled Regulatory

Planning and Review (58 FR 51735,

October 4, 1993). This final rule does

not contain any information collections

subject to OMB approval under the

Paperwork Reduction Act (PRA), 44

U.S.C. 3501 et seq., or impose any

enforceable duty or contain any

unfunded mandate as described under

Title II of the Unfunded Mandates

Reform Act of 1995 (UMRA) (Public

Law 104–4). Nor does it require any

prior consultation as specified by

Executive Order 13084, entitled

Consultation and Coordination with

Indian Tribal Governments (63 FR

27655, May 19, 1998); special

considerations as required by Executive

Order 12898, entitled Federal Actions to

Address Environmental Justice in

Minority Populations and Low-Income

Populations (59 FR 7629, February 16,

1994); or require OMB review or any

Agency action under Executive Order

13045, entitled Protection of Children

from Environmental Health Risks and

Safety Risks (62 FR 19885, April 23,

1997). This action does not involve any

technical standards that would require

Agency consideration of voluntary

consensus standards pursuant to section

12(d) of the National Technology

Transfer and Advancement Act of 1995

(NTTAA), Public Law 104–113, section

12(d) (15 U.S.C. 272 note). Since

tolerances and exemptions that are

established on the basis of a petition

under FFDCA section 408(d), such as

the tolerance in this final rule, do not

require the issuance of a proposed rule,

the requirements of the Regulatory

Flexibility Act (RFA) (5 U.S.C. 601 et

seq.) do not apply. In addition, the

Agency has determined that this action

will not have a substantial direct effect

on States, on the relationship between

the national government and the States,

or on the distribution of power and

responsibilities among the various

levels of government, as specified in

Executive Order 13132, entitled

Federalism (64 FR 43255, August 10,

1999). Executive Order 13132 requires

EPA to develop an accountable process

to ensure ‘‘meaningful and timely input

by State and local officials in the

Federal Register / Vol. 65, No. 101 / Wednesday, May 24, 2000 / Rules and Regulations 33479

development of regulatory policies that

have federalism implications.’’ ‘‘Policies

that have federalism implications’’ is

defined in the Executive Order to

include regulations that have

‘‘substantial direct effects on the States,

on the relationship between the national

government and the States, or on the

distribution of power and

responsibilities among the various

levels of government.’’ This final rule

directly regulates growers, food

processors, food handlers and food

retailers, not States. This action does not

alter the relationships or distribution of

power and responsibilities established

by Congress in the preemption

provisions of FFDCA section 408(n)(4).

VIII. Submission to Congress and the

Comptroller General

The Congressional Review Act, 5

U.S.C. 801 et seq., as added by the Small

Business Regulatory Enforcement

Fairness Act of 1996, generally provides

that before a rule may take effect, the

agency promulgating the rule must

submit a rule report, which includes a

copy of the rule, to each House of the

Congress and to the Comptroller General

of the United States. EPA will submit a

report containing this rule and other

required information to the U.S. Senate,

the U.S. House of Representatives, and

the Comptroller General of the United

States prior to publication of this final

rule in the Federal Register. This final

rule is not a ‘‘major rule’’ as defined by

5 U.S.C. 804(2).

List of Subjects in 40 CFR Part 180

Environmental protection,

Administrative practice and procedure,

Agricultural commodities, Pesticides

and pests, Reporting and recordkeeping

requirements.

Dated: May 10, 2000.

James Jones,

Director, Registration Division, Office of

Pesticide Programs.

Therefore, 40 CFR chapter I is

amended as follows:

PART 180—[AMENDED]

1. The authority citation for part 180

continues to read as follows:

Authority: 21 U.S.C. 321(q), (346a)

and 371.

2. In § 180.482, by alphabetically

adding the following entries to the table

in paragraph (a)(1) to read as follows.

§ 180.482 Tebufenozide; tolerances for

residues.

*****

(a) General. (1) ***

Commodity

Parts

per million

*****

Almond hulls ..................................... 25

*****

Tree nut crop group including pistachios ........................................... 0.1

*****

[FR Doc. 00–13071 Filed 5–23–00; 8:45 am]

BILLING CODE 6560–50–F

FEDERAL MARITIME COMMISSION

46 CFR Part 515, 545

[Docket No. 00–06]

Interpretations and Statements of

Policy Regarding Ocean

Transportation Intermediaries

AGENCY: Federal Maritime Commission.

ACTION: Interpretive rule.

SUMMARY: The Federal Maritime

Commission amends its regulations for

interpretive statements of policy to

interpret a section of its regulations

regarding ocean transportation

intermediaries to clarify the claim

settlement procedures.

DATES: This rule is effective June 23,

2000.

FOR FURTHER INFORMATION CONTACT:

Thomas Panebianco, General Counsel,

Federal Maritime Commission, 800

North Capitol St. NW, Room 1018,

Washington, DC 20573–0001; (202) 523–

5740.

SUPPLEMENTARY INFORMATION: On March

8, 1999, the Federal Maritime

Commission published a final rule and

interim final rule to add new regulations

at 46 CFR part 515 to implement

changes made by the Ocean Shipping

Reform Act of 1998 (‘‘OSRA’’), Public

Law 105–258, 112 Stat. 1902, to the

Shipping Act of 1984 (‘‘Shipping Act’’),

46 U.S.C. app. 1701 et seq., relating to

ocean transportation intermediaries

(‘‘OTIs’’). 64 FR 11156–11183. Section

515.23(b) sets forth the claim settlement

procedure for claimants seeking to

pursue a claim against an OTI. The

Interpretive Rule seeks to clarify the

Commission’s intention with respect to

this procedure, as there have been

reported misunderstandings in the

industry as to the responsibilities

inherent in this requirement.

Section 515.23(b)(1) sets forth the

claim settlement procedures and

provides, in part, that:

If a party does not file a complaint with the

Commission pursuant to section 11 of the

Act, but otherwise seeks to pursue a claim

against an ocean transportation intermediary

bond, insurance or other surety for damages

arising from its transportation-related

activities, it shall attempt to resolve its claim

with the financial responsibility provider

prior to seeking payment on any judgment for

damages obtained.

It is the Commission’s intention that a

claimant seeking to settle a claim in

accordance with this section should

promptly provide to the financial

responsibility provider all documents

and information relating to and

supporting its claim for the purpose of

evaluating the validity and subject

matter of the claim. The information

relevant to the claim settlement

procedure includes documents such as

bills of lading, as well as the existence

of pending court claims or judgments

obtained.

In addition, the financial

responsibility provider is allowed to

evaluate the validity of the claim during

the settlement process in § 515.23(b)(1).

However, if the parties do not reach a

settlement of the claim, the financial

responsibility provider, in accordance

with section 19 of the Shipping Act, 46

U.S.C. app. 1718 (1999), and 46 CFR

515.23(b)(2), must pay on a final

judgment and may only inquire into the

extent that the damages claimed arise

from the transportation-related activities

of the OTI, under section 3(17) of the

Shipping Act, 46 U.S.C. app. 1702(17).

Furthermore, if settlement of the

claim is not reached, the financial

responsibility provider may not

unilaterally reduce the amount awarded

in a final court judgment; Congress has

determined that, at that point, a

financial responsibility provider must

pay on a final judgment for damages

arising from the transportation-related

activities of the OTI, and the

Commission cannot nullify that

statutory requirement. However, the

financial responsibility provider and the

claimant are not precluded from

mutually agreeing to compromise the

amount awarded in a final judgment. In

the event that the financial

responsibility provider believes that a

judgment against its OTI bond principal

was obtained fraudulently, or that the

claim underlying the judgment is itself

fraudulent, the financial responsibility

provider is not precluded from

challenging a judgment if permitted in

the jurisdiction where it was obtained.