[Federal Register Volume 65, Number 185 (Friday, September 22, 2000)]
[Notices]
[Pages 57338-57344]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 00-24436]


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ENVIRONMENTAL PROTECTION AGENCY

[PF-961; FRL-6737-8]


Notice of Filing Pesticide Petitions to Establish Tolerances for 
Certain Pesticide Chemicals in or on Food

AGENCY: Environmental Protection Agency (EPA).

ACTION: Notice.

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SUMMARY: This notice announces the initial filing of pesticide 
petitions proposing the establishment of regulations for residues of 
certain pesticide chemicals in or on various food commodities.

DATES: Comments, identified by docket control number PF-961, must be 
received on or before October 23, 2000.

ADDRESSES: Comments may be submitted by mail, electronically, or in 
person. Please follow the detailed instructions for each method as 
provided in Unit I.C. of the SUPPLEMENTARY INFORMATION. To ensure 
proper receipt by EPA, it is imperative that you identify docket 
control number PF-961 in the subject line on the first page of your 
response.

FOR FURTHER INFORMATION CONTACT: By mail: Mary L. Waller, Registration 
Division (7505C), Office of Pesticide Programs, Environmental 
Protection Agency, 1200 Pennsylvania Ave., NW., Washington, DC 20460; 
telephone number: (703) 308-9354; e-mail address: [email protected].

SUPPLEMENTARY INFORMATION:

I. General Information

A. Does this Action Apply to Me?

    You may be affected by this action if you are an agricultural 
producer, food manufacturer or pesticide manufacturer. Potentially 
affected categories and entities may include, but are not limited to:

 
------------------------------------------------------------------------
                                                          Examples of
           Categories                 NAICS codes         potentially
                                                       affected entities
------------------------------------------------------------------------
Industry                          111...............  Crop production
  ..............................  112...............  Animal production
                                  311                 Food manufacturing
  ..............................  32532.............  Pesticide
                                                       manufacturing
------------------------------------------------------------------------

    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

[[Page 57339]]

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 PF-961. The official record 
consists of the documents specifically referenced in this action, any 
public comments received during an applicable comment period, 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 Highway, 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.

C. How and to Whom Do I Submit Comments?

    You may submit comments through the mail, in person, or 
electronically. To ensure proper receipt by EPA, it is imperative that 
you identify docket control number PF-961 in the subject line on the 
first page of your response.
    1. By mail. Submit your comments to: Public Information and Records 
Integrity Branch (PIRIB), Information Resources and Services Division 
(7502C), Office of Pesticide Programs (OPP), Environmental Protection 
Agency, 1200 Pennsylvania Ave., NW., Washington, DC 20460.
    2. In person or by courier. Deliver your comments to: Public 
Information and Records Integrity Branch (PIRIB), Information Resources 
and Services Division (7502C), Office of Pesticide Programs (OPP), 
Environmental Protection Agency, Rm. 119, Crystal Mall #2, 1921 
Jefferson Davis Highway, Arlington, VA. The PIRIB is open from 8:30 
a.m. to 4 p.m., Monday through Friday, excluding legal holidays. The 
PIRIB telephone number is (703) 305-5805.
    3. Electronically. You may submit your comments electronically by 
e-mail to:``[email protected]'', or you can submit a computer disk as 
described above. Do not submit any information electronically that you 
consider to be CBI. Avoid the use of special characters and any form of 
encryption. Electronic submissions will be accepted in Wordperfect 6.1/
8.0 or ASCII file format. All comments in electronic form must be 
identified by docket control number PF-961. Electronic comments may 
also be filed online at many Federal Depository Libraries.

D. How Should I Handle CBI That I Want to Submit to the Agency?

    Do not submit any information electronically that you consider to 
be CBI. You may claim information that you submit to EPA in response to 
this document as CBI 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. In addition to one complete 
version of the comment that includes any information claimed as CBI, a 
copy of the comment that does not contain the information claimed as 
CBI must be submitted for inclusion in the public version of the 
official record. Information not marked confidential will be included 
in the public version of the official record without prior notice. If 
you have any questions about CBI or the procedures for claiming CBI, 
please consult the person identified under FOR FURTHER INFORMATION 
CONTACT.

E. What Should I Consider as I Prepare My Comments for EPA?

    You may find the following suggestions helpful for preparing your 
comments:
    1. Explain your views as clearly as possible.
    2. Describe any assumptions that you used.
    3. Provide copies of any technical information and/or data you used 
that support your views.
    4. If you estimate potential burden or costs, explain how you 
arrived at the estimate that you provide.
    5. Provide specific examples to illustrate your concerns.
    6. Make sure to submit your comments by the deadline in this 
notice.
    7. To ensure proper receipt by EPA, be sure to identify the docket 
control number assigned to this action in the subject line on the first 
page of your response. You may also provide the name, date, and Federal 
Register citation.

II. What Action is the Agency Taking?

    EPA has received a pesticide petition as follows proposing the 
establishment and/or amendment of regulations for residues of certain 
pesticide chemical in or on various food commodities under section 408 
of the Federal Food, Drug, and Cosmetic Act (FFDCA), 21 U.S.C. 346a. 
EPA has determined that this petition contains data or information 
regarding the elements set forth in section 408(d)(2); however, EPA has 
not fully evaluated the sufficiency of the submitted data at this time 
or whether the data support granting of the petition. Additional data 
may be needed before EPA rules on the petition.

List of Subjects

    Environmental protection, Agricultural commodities, Feed additives, 
Food additives, Pesticides and pests, Reporting and recordkeeping 
requirements.


    Dated: September 6, 2000.

James Jones,

Director, Registration Division, Office of Pesticide Programs.

I. BASF Corporation Agricultural Products

7E4885

    EPA has received a pesticide petition 7E4885 from BASF Corporation, 
Agricultural Products, P.O. Box 13528, Research Triangle Park, NC 27709 
proposing, pursuant to section 408(d) of the FFDCA, 21 U.S.C. 346a(d), 
to amend 40 CFR part 180 by establishing tolerances for residues of 
epoxiconazole, (2RS,3SR)-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2-(1H-
1,2,4-triazol-1-yl)methyl oxirane in or on bananas at 0.5 parts per 
million (ppm) and in or on banana pulp at 0.2 ppm. EPA has determined 
that the petition contains data or information regarding the elements 
set forth in section 408(d)(2) of the FFDCA; however, EPA has not fully 
evaluated the sufficiency of the submitted data at this time or whether 
the data support granting of the petition. Additional data may be 
needed before EPA rules on the petition.

A. Residue Chemistry

    1. Plant metabolism. The metabolism in bananas was investigated 
using 14C labeled epoxiconazole. On average 70% of the total residue 
could be identified as parent. This corresponds to approximately 80% of 
the residue extractable from the peel and

[[Page 57340]]

approximately 90% of the residue extractable from the edible portion, 
pulp. Based on this result, a parent only method was developed to 
analyze residues from the magnitude of the residue trials.
    Under worst case practices (unbagged bananas) residue in the whole 
fruit ranged from the limit of quantitation (LOQ) (0.025 milligrams/
kilograms (mg/kg) to a maximum of 0.41 mg/kg. Banana pulp residues from 
bagged bananas ranged from < the LOQ (0.025 mg/kg) to 0.17 mg/kg and 
averaged 0.036 mg/kg. The average value was calculated by assuming all 
values below the LOQ were equal to one half the LOQ or 0.0125 mg/kg.
    2. Analytical method. The method of analysis includes extraction, 
liquid/liquid partition, column clean-up quantitation by gas 
chromatography/electron capture detection. Forty-three whole banana 
samples were fortified with epoxiconazole at levels ranging from 0.025 
mg/kg to 0.5 mg/kg. Recovery averaged 89.3% +/- 12.4%. Forty-one banana 
pulp samples were fortified with epoxiconazole at levels ranging from 
0.025 mg/kg to 0.25 mg/kg. Recovery averaged 88.8% +/- 9.2.%.
    3. Magnitude of residues. Fifteen crop residue trials were 
conducted in the banana growing regions of Mexico, South and Central 
America including three sites in Colombia, four sites in Costa Rica, 
four sites in Ecuador, one site in Guataemala, two sites in Hondouras, 
and one site in Mexico. Four sequential applications were made at the 
90 g/ha, slightly higher than the maximum use rate 75 g/ha to both 
bagged and unbagged bananas at each site. Fruit from both the bagged 
and unbagged treatments were harvested at 0 days following the last 
application.
    Whole fruit (peel and pulp) samples and pulp only samples were 
analyzed from all treatments at all sites. Under typical practices 
(bagged bananas) residue in the whole fruit ranged from < the LOQ 
(0.025 mg/kg) to a maximum of 0.082 mg/kg. Banana pulp residues from 
bagged bananas ranged from < the LOQ (0.025 mg/kg) to 0.05 mg/kg and 
averaged 0.013 mg/kg. The average value was calculated by assuming all 
values below the LOQ were equal to one half the LOQ or 0.0125 mg/kg.

B. Toxicological Profile

    1. Acute toxicity. The acute toxicity studies place technical 
epoxiconazole in acute toxicity category III for acute oral, dermal, 
and inhalation; and in acute toxicity category IV for skin and eye 
irritation; and the technical material is not a skin sensitizer.
    2. Genotoxicty. A modified Ames test (3 studies; point mutation): 
Negative; E. coli reverse mutation assay (1 study; point mutation): 
Negative; in vitro chinese hampster ovary/hypoxanthine guanine 
phophoribosyl transferase (CHO/HGPRT) mammalian cell mutation assay (1 
study; point mutation): Negative; in vitro Cytogentics--CHO cells (1 
study; chromosome aberrations): Negative; mouse micronucleus assay (1 
study; chromosome aberrations): Negative; in vitro unscheduled DNA 
synthesis (UDS) test using rat hepatocytes (1 study; DNA damage and 
repair): Negative; in vivo DNA binding in rats and mice (1 study; DNA 
binding): Negative.
    3. Reproductive and developmental toxicity. i. A developmental 
study via oral gavage in rabbits resulted in dosages of 0, 20, 50, and 
80 mg/kg/day highest dose tested (HDT) with a developmental toxicity no 
observed adverse effect level (NOAEL) of 80 mg/kg/day and a maternal 
toxicity of 20 mg/kg/day based on the following:
    a. Decreased body weight (bwt), food consumption, uterus weight, 
and increased resorption rate and post-implantation losses in the 80 
mg/kg/day dose level.
    b. Slight decreases of body weight and food consumption was seen in 
the 50 mg/kg/day dose level.
    c. No substance-related findings were observed in any fetus at all 
dose levels.
    ii. A developmental study was conducted via oral gavage in rats 
resulted in dosages of 0, 5, 15, and 45 mg/kg/day HDT with a 
developmental toxicity NOAEL of 5 mg/kg/day and a maternal toxicity of 
5 mg/kg/day based on the following:
    a. Signs of maternal toxicity, in the form of decreased body 
weights, food consumption, and increased placental weights observed at 
the highest dose tested.
    b. Maternal animals in the 45 mg/kg/day showed an increase in the 
number of late resorptions as compared to controls.
    c. Increased placental weights in the 15 mg/kg/day dose level.
    d. A significant number of fetuses with skeletal variations 
(especially rudimentary cervical and/or accessory 14th rib(s)) in the 
high dose group tested were observed. However, no malformations were 
observed in any pups in this study.
    iii. In a second developmental study in rats via dermal exposure 
for 6 hours/day on intact skin with dosages of 0, 100, 400, and 1,000 
mg/kg/day (HDT) with a development toxicity NOAEL of 400 mg/kg/day and 
a maternal toxicity of 400 mg/kg/day based on increased placental 
weights and a slight increase in the number of fetuses with skeletal 
variations was observed at the highest dose tested.
    iv. A combination of two multi-generation rat reproduction studies 
(study A dose levels were 0, 3.0, 30, and 145 mg/kg/day and study B 
dose levels were 0, 0.9, 2.3, and 23 mg/kg/day). Study A was 
discontinued after extreme systemic toxicity was observed at 145 mg/kg/
day. The following discussion summarizes the results from both studies. 
A reproductive NOAEL of 2.3 mg/kg/day and with a parental NOAEL of 2.3 
mg/kg/day were determined based on:
    a. Dose levels 23 mg/kg/day resulted in maternal death, 
clinical signs, clinical chemical effects, liver effects (i.e., 
damage), histopathology, and limited number of pregnancy and pups with 
reduced body weights which increased in severity to the upper dose 
levels, this also indicated that doses above 23 mg/kg/day were 
considered to be beyond the maximum tolerated dose (MTD) for pregnant 
rats.
    b. Questionable effects were observed in the 3.0 mg/kg/day dose 
level.
    c. No treatment-related clinical signs, body weight changes, 
parameters of fertility and gestation, or macro- or histopathological 
changes were observed for the parental F0, F1, and F2 at dose levels 
equal to and below 2.3 mg/kg/day.
    4. Chronic toxicity. i. A series of two 1-year dog studies (study A 
dose levels were 0, 1.6, 15, and 49 mg/kg/day for which a NOAEL was 
established in females, and study B dose levels were 0, 0.3, 0.6, 0.9, 
and 1.1 mg/kg/day to determine a NOAEL in males. The NOAEL was 
established as 1.1 mg/kg/day based on the following effects:
    a. Mortality in the 49.0 mg/kg/day dose group with severe clinical 
signs and evidence of liver damage in those dogs which were sacrificed 
for humane reasons.
    b. Hematological examinations demonstrated effects in either male 
or female dogs at dose levels 1.6 mg/kg/day.
    c. Clinical chemical effects of varying types were seen in either 
male and female dogs at dose levels 15.0 mg/kg/day.
    d. No effects were observed in male animals at levels of 
1.1 or female dogs at dose levels of 1.6 mg/kg/
day.
    ii. Separate chronic feeding and oncogenicity studies in rats were 
performed to assess the chronic toxicity and oncogenic potential of 
epoxiconazole. The chronic toxicity study was conducted at dose levels 
of 0 and approximately 2, 8, 38, and 78 mg/

[[Page 57341]]

kg/day. The oncogenicity study was conducted at dose levels of 0 and 
approximately 2, 7, 40, and 80 mg/kg/day.
    The results from the 2 studies are combined and summarized as 
follows:
    The NOAEL was determined to be 2.0 mg/kg/day based on the following 
effects:
    a. Decreases in body weights and food consumption were observed in 
both male and female rats at dose levels 38 mg/kg/day dose 
groups with a very slight progression of severity to the upper level.
    b. Varying clinical chemical and hematological effects were 
observed in either male and/or female rats at dose levels 
8mg/kg/day with a very slight progression of severity to the 
upper levels.
    c. Increased absolute and relative liver weights were seen for 
males and/or females at dose levels 38 mg/kg/day.
    d. Microscopic findings were observed in the liver for male and/or 
female rats at dose levels 38 mg/kg/day, in female adrenals 
at the highest dose test, and in the ovaries at dose levels 
38 mg/kg/day.
    e. An increased incidence of neoplasms occurred at dose levels 
greater than the MTD of 8 mg/kg/day in the females for the adrenals and 
ovaries. No increased number of neoplasms were seen in male rats due to 
the fact that the MTD in male rats was the HDT as opposed to the female 
rat which was significantly lower. Taking into account the results 
obtained in these studies, it is concluded that the reduction in body 
weight gain at 38 and 78 mg/kg/day levels met the criteria for a 
maximum tolerated dose. It has been determined that effects observed at 
the 10 mg/kg/day dose level achieved or approximated the MTD.
    The effects on the ovaries were as follows:
     Decreasing aromatase enzyme activity which, is a response 
from converting both testosterone and adrostendione (male sex-steroids) 
into female sex steroids (e.g., estradiol). This action would result in 
decreased estradiol (i.e., estrogen and prolactin) and increased 
androgen levels (i.e., testosterone). As a consequence of reduced 
estradiol levels, measured LH and FSH concentrations are slightly 
altered.
     The increased incidences of neoplasms in the ovaries are 
considered to be the result of a continuous cell proliferation by these 
stimulating hormones of the pituitary-gonadal axis (LH and FSH).
    The effects on the adrenals were as follows:
     Decreasing adrenal-cortical enzyme activity. This action 
would result in decreased adrenal hormones such as corticosterone 
levels. As a consequence of reduced corticosterone levels, pronounced 
ACTH concentrations are found.
     The increased incidences of neoplasms in the adrenals are 
considered to be the result of a continuous cell proliferation by these 
stimulating hormones of the pituitary-adrenal axis (ACTH).
    For risk assessment purposes the results obtained at 38 and 78 mg/
kg/day dose levels should not be used because an extrapolation to lower 
dose levels is not justified due to the unphysiological conditions in 
animals treated at dose levels near or at the MTD. Under these 
circumstances neoplastic and non-neoplastic mechanisms may be induced 
which will not occur at dose levels in which the animals are able to 
maintain their normal physiological homeostasis.
    The increases in tumor incidence in endocrine organs due to 
hormonal imbalance are considered to have a threshold value, because at 
dose levels which do not induce cellular alterations via hormone levels 
in these organs, a subsequent proliferation and hence tumor formation 
cannot occur.
    iii. An oncogenicity study in mice fed dosages of 0, 0.17, 0.81, 
35.3, and 70.4 (males) or 205.4 (females) mg/kg/day with a NOAEL of 
0.81 mg/kg/day for male and female mice based on the following effects:
    a. Highly significant decreased body weights were observed in both 
male and/or female mice at the mid-high and highest dose tested.
    b. Clinical sign of deteriorated state of general health were 
observed in high dose female mice.
    c. Increased liver weights and microscopic findings were observed 
for male and female mice at dose the highest dose tested.
    d. An increased incidence of neoplasms occurred at dose levels 
(70.4/205.4 mg/kg/day) greater than the MTD of 35.3 mg/kg/day in the 
male and female mice for the liver.
    Taking into account the results obtained in this study, the 
following conclusions are drawn: The severe reduction in body weight 
and body weight gain at dose levels 35.3 mg/kg/day indicates 
that these dose levels exceeded the criteria for a MTD. It has been 
determined that liver tumor effects observed at the 70.4 and 205.4 mg/
kg/day dose levels clearly exceeded the MTD. The liver necrosis 
observed in the male and female mice, further support the finding that 
the MTD was exceeded in the 70.4 and 205.4 mg/kg/day dose levels.
    A series of mechanistic studies were performed to elucidate and 
define the liver promotion properties of epoxiconazole. The following 
conclusions can be drawn from the data:
     The material is a potent inducer of the hepatic cytocrome 
P-450 enzyme system, similar to the drug-phenobarbital.
     The material induced proliferation of the smooth 
endoplasmatic reticulum in the liver centrolobular hypertrophy and 
induction of phase 1 and phase 2 enzymes of the xenobiotic metabolism.
     The material was determined not to be an initiator of the 
carcinogenic process, but a promoter of initiated cells in the 
tumorgenesis as has been similarly shown with drug--phenobarbital.
    As stated above, for risk assessment purposes the results obtained 
at 70.4 and 205.4 mg/kg/day dose levels should not be used because an 
extrapolation to lower dose levels is not justified due to the 
unphysiological conditions in animals treated at dose levels exceeding 
the MTD. Under these circumstances, neoplastic and non-neoplastic 
mechanisms may be induced which will not occur at dose levels in which 
the animals are able to maintain their normal physiological 
homeostasis.
    5. Animal metabolism. Since there are no animal feed items 
associated with bananas, there is no likelihood of secondary residues 
in meat, milk, poultry or eggs. Therefore, data concerning metabolism 
in livestock is not required.
    6. Metabolite toxicology. Residues of the parent molecule, 
epoxiconazole are the only residues of concern.
    7. Endocrine disruption. A series of mechanistic studies were 
performed to elucidate and define the aromatase enzyme inhibition 
properties of epoxiconazole. The following conclusions can be drawn 
from the in vivo data: The effects on the ovaries are assessed to be 
the result of the following:
     Decreasing aromatase enzyme activity which is responsible 
for converting both testosterone and adrostendione (male sex-steroids) 
into female sex steroids (e.g., estradiol). This action would result in 
decreased estradiol (i.e., estrogen) and increased androgen. As a 
consequence of reduced estradiol levels, measured LH and FSH 
concentrations are slightly altered.
     The increased incidences of neoplasms in the ovaries are 
considered to be the result of a continuous cell proliferation by these 
stimulating

[[Page 57342]]

hormones of the regulating hormones of the pituitary-gonadal axis (LH 
and FSH).
    The changes adrenals are assessed to be the result of the 
following:
     Decreasing adrenal-cortical enzyme activity. This action 
would result in decreased adrenal hormones such as corticosterone 
levels. As a consequence of reduced corticosterone levels, pronounce 
ACTH concentrations are found.
     The increased incidences of neoplasms in the adrenals are 
considered to be the result of a continuos cell proliferation by these 
stimulating hormones of the pituitary-adrenal axis ACTH.

C. Aggregate Exposure

    1. Dietary exposure. For the purpose of assessing the potential 
chronic dietary exposure, BASF has estimated aggregate exposure based 
on theoretical maximum residue contribution (TMRC) from the tolerance 
of epoxiconazole in or on bananas at 0.2 ppm the maximum residue found 
in banana pulp. The TMRC is a ``worst case'' estimate of dietary 
exposure since it is assumed that 100% of all the crops for which the 
tolerances are established are treated and that pesticide residues are 
always found at tolerance levels. Based on the expected reference dose 
(RfD) of 0.011 mg/kg/day (from the NOAEL determined in the chronic dog 
study and a 100-fold safety factor) and the tolerance level residue 
chronic dietary exposure of the general population is less than 1% of 
the RfD.
    i. Food. This is a new chemical and there are no other food uses 
except for the proposed use on bananas.
    ii. Drinking water. No exposure is expected from drinking water as 
this is an import tolerance and no U.S. registrations are expected.
    2. Non-dietary exposure. There are no non-occupational sources of 
exposure to epoxiconazole for the general population due to fact the 
action being requested is to establish a tolerance for import purposes 
only.

D. Cumulative Effects

    BASF has considered the potential for cumulative effects of 
epoxiconazole and other substances which may have a common mechanism of 
toxicity. BASF is aware of other triazole fungicides but has no 
reliable toxicology information concerning those other materials which 
would allow a determination regarding similarity of toxicity 
mechanisms. Therefore, BASF has considered only the potential risks of 
epoxiconazole in its exposure assessment.

E. Safety Determination

    1. U.S. population. Using the exposure assumptions described above, 
based on the completeness and the reliability of the toxicity data, 
BASF has estimated that aggregate exposure to epoxiconazole will 
utilize less than 1% of the RfD for the U.S. population. EPA generally 
has no concern for exposure below 100% of the RfD. Therefore, based on 
the completeness and reliability of the toxicity data, and the exposure 
assessment discussed above, BASF concludes that there is a reasonable 
certainty that no harm will result from aggregate exposure to residues 
of epoxiconazole, including all anticipated dietary exposure and all 
other non-occupational exposures.
    2. Infants and children. The findings in the rat and rabbit are 
most likely as a result of excessive maternal toxicity, treatment of 
pregnant rats and rabbits with epoxiconazole induced embryotoxic 
effects which manifested themselves in the form of early resorptions 
and structural anomalies in the offspring. In both the rat and rabbit, 
the dose-effect relationship was rather steep and showed clear 
threshold levels. At dose levels below the threshold of maternal 
toxicity, reproductive parameters as well as the offsprings remained 
entirely unaffected.
    This data demonstrate that the rat and rabbit are similarly 
sensitive to epoxiconazole. Additionally, the NOAEL of 1.1 mg/kg/day 
from the chronic dog study used to set the RfD is 4.5x and 72.7x lower 
than the maternal developmental NOAELs established in the rat and 
rabbit teratology studies, respectively. The developmental effects 
observed in either the rat or rabbit occurred only at maternally toxic 
doses. Therefore, no additional safety factor is needed for children.
    Using the assumption stated for the general population, BASF 
concluded that the most sensitive child population group is that of 
children <1-year. Using the same RfD and the same conservative exposure 
assumptions employed in the dietary risk analysis for the general 
population, it was calculated that the exposure to this group is to be 
approximately 2% of the RfD for the use proposed in this document. 
Therefore, based on the completeness and reliability of the toxicity 
data, and the exposure assessment discussed above, BASF concludes that 
there is a reasonable certainty that no harm will result to infants and 
children from aggregate exposure to residues of epoxiconazole, 
including all anticipated dietary exposure and all other non-
occupational exposures.

F. International Tolerances

    A maximum residue level has not been established by the Codex 
Alimentarius Commission for epoxiconazole in bananas.

II. Tomen Agro, Inc.

9E06020

    EPA has received a pesticide petition 9E06020 from the TM-210 (SZX 
0722) Fungicide Task Force, comprised of Tomen Agro, Inc., 100 First 
Street, Suite 1700, San Francisco, CA 94105, and Bayer Corporation, 
8400 Hawthorn Road, Kansas City, MO 64120 proposing, pursuant to 
section 408(d) of the FFDCA, 21 U.S.C. 346a(d), to amend 40 CFR part 
180 by establishing a tolerance for residues of iprovalicarb: (1S)-2-
methyl-1-[[[1-(4-methylphenyl)ethyl] amino] carbonyl] propyl] carbamic 
acid 1-methylethyl ester in or on the raw agricultural commodity 
imported grapes at 2 ppm and on the processed commodity imported 
raisins at 3 ppm. EPA has determined that the petition contains data or 
information regarding the elements set forth in section 408(d)(2) of 
the FFDCA; however, EPA has not fully evaluated the sufficiency of the 
submitted data at this time or whether the data support granting of the 
petition. Additional data may be needed before EPA rules on the 
petition.

A. Residue Chemistry

    1. Plant metabolism. The metabolism of iprovalicarb was 
investigated in grapes, potatoes and tomatoes, and the metabolic 
pathway is similar in the three crops. The rate of degradation on 
plants is quite low, and the parent compound was always the major 
component, with quantitatively relevant metabolites formed only in 
potatoes. The metabolites observed in the potato were also observed in 
the rat. Therefore, iprovalicarb is the only residue of concern. Plant 
metabolism proceeds along three pathways:
    i. Hydroxylation/glycosylation of parent at the 4-methyl group on 
the phenyl ring, followed by further conjugations.
    ii. Cleavage of the amide group between the L-valine and p-methyl-
phenethylamine moieties.
    iii. Hydroxylation/glycosylation of parent at the phenyl-ring 3 
position.
    2. Analytical method. The proposed enforcement residue analytical 
method is an HPLC method with ultra violet (UV) detection. The limit of 
determination is 0.05 ppm in grapes, wine, juice and raisins, and the 
mean recovery is 94%. DFG multiresidue method S19 has been evaluated as 
an

[[Page 57343]]

analytical method for the determination of iprovalicarb residues in 
grapes and other commodities. The limit of quantitation (LOQ) of 
iprovalicarb in/on grapes is 0.01 ppm. Recoveries in spiked samples 
ranged from 79% to 119%, with the standard deviations ranging from 0.06 
ppm to 0.16 ppm. DFG multiresidue method S 19 (with modified 
extraction) was successfully validated as an analytical method for the 
determination of residues in/on grapes and other commodities.
    3. Magnitude of residues. The maximum measured residue resulting 
from treatment according to the proposed labels and representative 
viticulture practices was 1.40 ppm in grapes and 2.55 ppm in raisins. 
Measured residues in juice and wine were lower than the measured 
residues in grapes.

B. Toxicological Profile

    1. Acute toxicity. The acute oral LD50 in Wistar rats is 
greater than 5,000 mg/kg body weight.
    2. Genotoxicty. Iprovalicarb was non-mutagenic or non-clastogenic 
in six of six assays:
    i. Salmonella/microsome test, with and without S9 mix.
    ii. V79-HPRT forward mutation assay, with and without metabolic 
activation.
    iii. CHO cell assay, with and without metabolic activation in 
vitro.
    iv. In vitro rat primary hepatocyte unscheduled DNA synthesis UDS 
assay.
    v. Mouse micronucleus test.
    vi. \32\P-postlabelling assay of the uterus and urinary bladder of 
rats. Based upon these studies, iprovalicarb is non-mutagenic and non-
genotoxic both in vitro and in vivo.
    3. Reproductive and developmental toxicity-- i. In a 2-generation 
reproduction study in Wistar rats receiving 0, 100, 2,000 or 20,000 ppm 
iprovalicarb in the diet, the parental NOAEL was 2,000 ppm based upon 
reduced body weight development and increased liver weight at 20,000 
ppm. The reproductive toxicity NOAEL was 2,000 ppm (100 mg/kg bwt/day) 
based upon delayed body weight development in F1 and F2 pups during 
lactation, slightly reduced mean litter weight at birth and at day 28, 
increased relative liver weights and a reduced lactation index in F1 
pups at 20,000 ppm.
    ii. In a developmental toxicity study in Wistar rats, the maternal 
and developmental NOAEL was 1,000 mg/kg bwt/day (limit dose for study 
and highest dose tested (LD/HDT)).
    iii. In a developmental toxicity study in Russian rabbits, the 
maternal and developmental NOAEL was 1,000 mg/kg bwt/day LD/HDT.
    4. Subchronic toxicity-- i. In the 13-week feeding study in Wistar 
rats, the doses were 0, 1,250, 5,000 and 20,000 ppm. The NOAEL was 
5,000 ppm (372.7 mg/kg bwt/day in males; 561.4 mg/kg bwt/day in 
females) based upon reduced body weight gain, increased feed intake 
(females only), changed clinical chemistry parameters (including liver 
enzyme induction) and elevated absolute liver weights at 20,000 ppm.)
    ii. In the 13-week feeding study in B6C3F1 mice, the doses were 0, 
280, 1,400, 7,000, and 14,000 ppm in the diet. The NOAEL in males was 
1,400 ppm (325.0 mg/kg bwt/day) based upon elevated water intake and a 
changed hematological parameter (MCV) at 7,000 ppm (1,724.6 mg/kg bwt/
day). The NOAEL in females was 7,000 ppm (3,599.5 mg/kg bwt/day) based 
upon elevated water intake, changed parameter in the red blood count, 
and increased liver weights at 14,000 ppm (6,869.0 mg/kg bwt/day).
    iii. In the 13-week feeding study in Beagle dogs, the doses were 0, 
250, 2,500 and 50,000 ppm iprovalicarb in the diet (0, 9.1, 62.5 and 
1,250 mg/kg bwt/day). The NOAEL was 250 ppm (9.1 mg/kg bwt/day) for 
males and females based upon liver effects (increased activity of 
alkaline phosphatase and hepatocellular hypertrophy in one animal) at 
2,500 ppm.
    5. Chronic toxicity-- i. Wistar rats received 0, 500, 5,000 or 
20,000 ppm iprovalicarb in the diet for 24 months. The NOAEL in females 
was 500 ppm (31.7 mg/kg bwt/day) based upon decreased body weights, 
changed clinical chemistry parameters (increased cholesterol 
concentration and decreased total bilirubin concentration), increased 
relative liver weights and histopathological findings (increased 
incidences of hepatocellular hypertrophy) at 5,000 ppm. The NOAEL in 
males was 5,000 ppm (262.5 mg/kg bwt/day) based upon decreased body 
weights, increased APh-activity, and slight increase of tumor 
incidences at 20,000 ppm. The histopathological NOAEL was 5,000 ppm 
(262.5 mg/kg bwt/day in males and 326.3 mg/kg bwt/day in females).
    To further evaluate the results of the chronic feeding study in 
rats:
    a. A special 2-day/13-week metabolism study was conducted in Wistar 
rats at 500 ppm and 20,000 ppm in the diet. Some quantitative 
differences (shift in diastereomer ratio in favor of S,R; relative 
higher amounts of p-methyl-phenethylamine, higher proportions of 
unchanged parent compound in feces) after administration of 20,000 ppm 
compared to the low dose of 500 ppm were observed.
    b. Plasma concentrations were investigated in a special 12-week 
feeding study in HsdCpb:WU rats. The plasma concentrations of parent 
compound increased to a measurable level at a dose of 20,000 ppm in the 
diet. The concentration of parent in plasma was very low due to 
extensive metabolism during the first pass in the liver. At a dose of 
20,000 ppm, the iprovalicarb-carboxylic acid (S,R) diastereomer 
increased in relation to the corresponding (S,S) diastereomer when 
compared to the low dose.
    c. A bioavailability study was conducted in Wistar rats. 
Administration of thermodynamically stable and thermodynamically labile 
modifications of iprovalicarb to Wistar rats at concentrations of 2,000 
and 20,000 ppm for 2 weeks resulted in no toxicologically relevant 
differences based upon the concentration of the main metabolite, 
iprovalicarb-carboxylic acid, in plasma. Therefore, the 
thermodynamically stable and thermodynamically labile modifications of 
iprovalicarb demonstrated no significant differences in intestinal 
absorption and bioavailability.
    d. An in vivo \32\P-postlabelling assay of uterus and urinary 
bladder epithelium was conducted in female Wistar rats dosed at 10,000 
or 20,000 ppm in the diet for 7 days. Iprovalicarb was determined to be 
inactive in the assay.
    e. A liver foci test was conducted in male Bor: WISW (SPF-Cpb) rats 
that were dosed by oral gavage with 0 or 1,000 mg/kg iprovalicarb for 
28 days, followed by a promotion treatment with phenobarbital over a 
period of 8 weeks. Iprovalicarb was determined to not have a tumor 
initiating potential.
    Based upon the 24-month chronic feeding study in rats, plus the 
special studies, a dose of 20,000 ppm exerts a continuous stress on the 
xenobiotic metabolizing capacity of the liver that is not observed at 
lower doses. Moreover, iprovalicarb has no genotoxic potential and no 
tumor initiation potential. Therefore, iprovalicarb is not carcinogenic 
in rats.
    ii. B6C3F1 mice received 0, 280, 1,400, or 7,000 ppm 
iprovalicarb in the diet for up to 105 weeks. The NOAEL in males was 
1,400 ppm (283.4 mg/kg bwt/day) based upon slightly higher food and 
water intake and slightly lower body weights at 7,000 ppm (1,566.8 mg/
kg bwt/day). The NOAEL in females was 7,000 ppm (2,544 mg/kg bwt/day), 
the HDT. No oncogenic potential was observed in mice.
    iii. Beagle dogs received 0, 80, 800 or 8,000 ppm iprovalicarb in 
the diet for 53 weeks. The NOAEL was 80 ppm (2.62

[[Page 57344]]

mg/kg bwt/day in males and 2.68 mg/kg bwt/day in females) based upon 
liver effects (increased serum activities of ALT and APh, cellular 
hypertrophy and periportal fatty change) at 800 ppm (24.69 mg/kg bwt/
day in males and 28.10 mg/kg bwt/day in females). A follow-up study was 
conducted in Beagle dogs that received 0, 10, 20, 40, or 80 ppm 
iprovalicarb in their diet for 28 days. The NOAEL for microsomal liver 
enzyme induction was determined to be 20 ppm (0.77 mg/kg bwt/day). 
Microsomal liver enzyme induction was observed at the higher doses, and 
reversal of induction was observed within a 4-week recovery period in 
the 80 ppm dose group (2.93 mg/kg bwt/day).
    6. Animal metabolism. Iprovalicarb is readily absorbed, and greater 
than 97.8% of the total radioactivity was eliminated in urine and feces 
within 48 hours of dosing. Iprovalicarb is extensively metabolized in 
the rat. The primary metabolites (>58% of the administered dose) were 
diastereomers of iprovalicarb-carboxylic acid. Eight minor metabolites, 
each representing less than 2% of the administered dose, were 
quantified.
    7. Metabolite toxicology. The toxicity of p-methyl-phenethylamine, 
a rat, plant and soil metabolite, was investigated in 2 studies:
    i. The acute oral LD 50 in Wistar rats was determined to 
be in the range of 300 to 500 mg/kg bw.
    ii. No mutagenic activity was observed in the Salmonella/microsome 
test. p-Methyl-phenethylamine was found at concentrations of 0.2% and 
has been determined to not be toxicologically significant.
    8. Endocrine disruption. No endocrine disruption potential was 
observed in the 2-generation reproduction study, developmental toxicity 
studies, subchronic feeding studies, and chronic feeding studies.

C. Aggregate Exposure

    1. Dietary exposure. There are no registered uses of iprovalicarb 
in the U.S., and no registrations or other tolerances are pending. 
Dietary exposure to iprovalicarb in the U.S. is limited to residues in/
on imported grapes, grape juice, wine, and raisins.
    i. Food. The anticipated residue in/on fresh grapes based upon the 
field studies is 0.50 ppm, and 35.71% of the fresh grapes consumed in 
the U.S. are imported. The anticipated residue in grape juice based 
upon the field and processing studies is 0.050 ppm, and 37.05% of the 
grape juice consumed in the U.S. is imported. The anticipated residue 
in wine based upon the field and processing studies is 0.32 ppm, and 
17.38% of the wine consumed in the U.S. is imported. The anticipated 
residue in raisins based upon the field and processing studies is 0.91 
ppm, and 8.165% of the raisins consumed in the U.S. are imported. 
Assuming 100% of the imported commodities are treated and have the 
average residue resulting from the maximum international use of 
iprovalicarb, the total anticipated residue is 0.000021 mg/kg bwt/day 
in the U.S. diet and 0.000056 mg/kg bwt/day for the most exposed sub-
population, children 1 to 6 years old.
    ii. Drinking water. Iprovalicarb is not registered for use in the 
United States. Therefore, there is no exposure to iprovalicarb through 
drinking water in the United States.
    2. Non-dietary exposure. Iprovalicarb is not used in the United 
States. Therefore, there is no non-dietary exposure to iprovalicarb in 
the United States.

D. Cumulative Effects

    Iprovalicarb is a member of a new class of chemistry and does not 
have a mode of action that is common with other registered pesticides. 
Therefore, there are no cumulative effects.

E. Safety Determination

    1. U.S. population. The reference dose (RfD) is 0.03 mg/kg bwt/day. 
Based upon anticipated residues in imported commodities and assuming 
100% of the imported commodities contain residue resulting from the 
proposed European use of iprovalicarb, the estimated chronic dietary 
margin of exposure of the U.S. population is 0.07% of the RfD. 
Therefore, there is a reasonable certainty of no harm to the U.S. 
population resulting from exposure to iprovalicarb residues in/on 
imported commodities.
    2. Infants and children. The population subgroup with the maximum 
estimated dietary exposure is children age 1 to 6 years old. For this 
subgroup, and using the same assumptions as listed for the U.S. 
population, the estimated chronic dietary margin of exposure is 0.18% 
of the RfD. Therefore, there is a reasonable certainty of no harm to 
infants and children in the U.S. resulting from exposure to 
iprovalicarb residues in/on imported commodities.

F. International Tolerances

    The following maximum residue levels are pending in the European 
Union: 2.0 mg/kg in/on grapes; 0.5 mg/kg in animal fat; 0.05 mg/kg in 
potatoes, animal meat, animal edible offal and eggs; and 0.01 mg/kg in 
milk.

[FR Doc. 00-24436 Filed 9-21-00; 8:45 a.m.]
BILLING CODE 6560-50-S