[Federal Register Volume 60, Number 85 (Wednesday, May 3, 1995)]
[Rules and Regulations]
[Pages 21736-21739]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 95-10861]



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ENVIRONMENTAL PROTECTION AGENCY
40 CFR Parts 180 and 185

[PP 2F4116 and FAP 2H5644/R2124; FRL-4949-3]
RIN 2070-AB78


Myclobutanil; Pesticide Tolerances and Food Additive Regulation

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This rule establishes permanent tolerances for the combined 
residues of the fungicide myclobutanil and a metabolite in or on the 
raw agricultural commodities stone fruits (except cherries) at 2.0 
parts per million (ppm) and cherries at 5.0 ppm and establishes a food 
additive regulation for the combined residues in or on the processed 
food commodity dried plums at 8.0 ppm. The Rohm & Haas Co. requested 
establishment of these tolerances and food additive regulation.

EFFECTIVE DATE: This regulation became effective on March 30, 1995.

ADDRESSES: Written objections and hearing requests, identified by the 
document control number, [PP 2F4116 and FAP 2H5644/R2124], may be 
submitted to : Hearing Clerk (1900), Environmental Protection Agency, 
Rm. M3708, 401 M St., SW., Washington, DC 20460. A copy of any 
objections and hearing requests filed with the Hearing Clerk should be 
identified by the document control number and submitted to: Public 
Response and Program Resources Branch, Field Operations Division 
(7506C), Office of Pesticide Programs, Environmental Protection Agency, 
401 M St., SW., Washington, DC 20460. In person, bring a copy of the 
objections and hearing requests to Rm. 1132, CM #2, 1921 Jefferson 
Davis Hwy., Arlington, VA 22202. Fees accompanying objections shall be 
labeled ``Tolerance Petition Fees'' and forwarded to: EPA Headquarters 
Accounting Operations Branch, OPP (Tolerance Fees), P.O. Box 360277M, 
Pittsburgh, PA 15251.
    A copy of objections and requests for hearings filed with the 
Hearing Clerk may also be submitted electronically by sending 
electronic mail (e-mail) to: [email protected]. Copies of 
objections and requests for hearings must be submitted as an ASCII file 
avoiding the use of special characters and any form of encryption. 
Copies of objections and requests for hearings will also be accepted on 
disks in WordPerfect in 5.1 file format or ASCII file format. All 
copies of objections and requests for hearings in electronic form must 
be identified by the docket number [PP 2F4116 and FAP 2H5644/R2124]. No 
Confidential Business Information (CBI) should be submitted through e-
mail. Electronic copies of objections and requests for hearings on this 
rule may be filed online at many Federal Depository Libraries. 
Additional information on electronic submissions can be found below in 
this document.

FOR FURTHER INFORMATION CONTACT: By mail: Connie B. Welch, Product 
Manager (PM) 21, Registration Division (7505C), Office of Pesticide 
Programs, Environmental Protection Agency, 401 M St., SW., Washington, 
DC 20460. Office location and telephone number: Rm. 227, CM #2, 1921 
Jefferson Davis Hwy., Arlington, VA 22202, (703)-305-6900; e-mail: 
[email protected].

SUPPLEMENTARY INFORMATION: EPA issued notices, published in the Federal 
Register of December 30, 1992 (57 FR 62333), which announced that the 
Rohm & Haas Co., Independence Mall West, Philadelphia, PA 19105, had 
submitted pesticide petition (PP) 2F4116 proposing to amend 40 CFR 
180.443 by establishing permanent tolerances for the residues of the 
fungicide myclobutanil, [alpha-butyl-alpha-(3-hydroxybutyl)-1H-1,2,4-
triazole-1-propanenitrile], and both the free and bound forms of its 
metabolite, alpha-(3-hydroxybutyl)-alpha-(4-chlorophenyl)-1H-1,2,4-
triazole-1-propanenitrile, in or on stone fruits group (except 
cherries) at 2.0 ppm and cherries at 5.0 ppm and food additive petition 
(FAP) 2H5644 proposing to amend 40 CFR 185.4350 by establishing a 
tolerance for the combined residues of myclobutanil and its metabolite 
in or on the food additive commodity dried plums at 8.0 ppm. Rohm & 
Haas Co. also requested that previous petitions submitted for stone 
fruits (PP 9F3811, PP 1F3954, and FAP 1H5608) be combined in these 
petitions.
    Time-limited tolerances were established for myclobutanil in or on 
the raw agricultural commodities nectarines and peaches at 2.0 ppm and 
cherries (sweet and sour) at 4.0 ppm with an expiration date of October 
1, 1994, in response to PP 9F3811 in a document in the Federal Register 
of February 5, 1992 (57 FR 4368). These tolerances were extended to 
April 1, 1995, on September 30, 1994.
    There were no comments received in response to the notices of 
filing of any of the petitions. The data submitted in support of the 
petitions and other relevant material have been evaluated. The 
pesticide is considered useful for the purpose for which the tolerances 
are sought. The toxicological data [[Page 21737]] considered in support 
of the tolerances include the following:
    1. A 1-year dog feeding study using doses of 0, 10, 100, 400, and 
1,600 ppm (equivalent to doses of 0, 0.34, 3.09, 14.28, and 54.22 
milligrams/kilogram (mg/kg) body weight (bwt)/day in males and 0, 0.40, 
3.83, 15.68, and 58.20 mg/kg bwt/day in females). The no-observed-
effect level (NOEL) is 100 ppm (3.09 mg/kg/day for males and 3.83 mg/
kg/day for females) based upon hepatocellular hypertrophy, increases in 
liver weights, ``ballooned'' hepatocytes, and increases in alkaline 
phosphatase, SGPT, and GGT, and possible slight hematological effects. 
The lowest-observed-effect level (LOEL) is 400 ppm (14.28 mg/kg/day for 
males and 15.68 mg/kg/day for females).
    2. A 2-year chronic feeding/carcinogenicity study in rats using 
dietary concentrations of 0, 50, 200, and 800 ppm (equivalent to doses 
of 0, 2.49, 9.84, and 39.21 mg/kg bwt/day in males and 0, 3.23, 12.86, 
and 52.34 mg/kg bwt/day in females). The NOEL for chronic effects other 
than carcinogenicity is 2.49 mg/kg/day, and the LOEL is 9.84 mg/kg/day 
based on testicular atrophy in males. No other significant effects were 
observed in either sex at the stated dose levels over a 2-year period. 
In addition, no carcinogenic effects were observed in either sex at any 
of the dose levels tested. Based on the toxicological findings, the 
maximum tolerated dose (MTD) selected for testing (based on the 90-day 
feeding study) was not high enough to fully characterize the compound's 
carcinogenic potential.
    The study was repeated at dose levels of 0 and 2,500 ppm (125 mg/
kg/day) in the diet, which approaches the MTD, in order to characterize 
the carcinogenic potential. At 2,500 ppm, the observed effects 
included: decreases in absolute and relative testes weights, increases 
in the incidences of centrilobular to midzonal hepatocellular 
enlargement and vacuolation in the liver of both sexes, increases in 
bilateral aspermatogenesis in the testes, increases in the incidence of 
hypospermia and cellular debris in the epididymides, and increased 
incidence of arteritis/periarteritis in the testes. In this study, a 
NOEL could not be established because there were effects at the only 
dose level tested. Myclobutanil was not oncogenic when tested under the 
conditions of the study.
    3. A 2-year carcinogenicity study in mice using dietary 
concentrations of 0, 20, 100, and 500 ppm (equivalent to 0, 2.7, 13.7, 
and 70.2 mg/kg/day in males and 0, 3.2, 16.5 and 85.2 mg/kg/day in 
females). The NOEL for chronic effects other than carcinogenicity was 
20 ppm (2.7 mg/kg/day in males and 3.2 mg/kg/day in females). The LOEL 
was 100 ppm (13.7 mg/kg/day in males and 16.5 mg/kg/day in females) 
based on a slight increase in liver mixed-function oxidase (MFO). 
Microscopic changes in the liver were evident in both sexes at 500 ppm 
(70.2 mg/kg/day in males and 85.2 mg/kg/day in females). There were no 
carcinogenic effects in either sex at any dose level tested. The 
highest selected dose was satisfactory for evaluating carcinogenic 
potential in male mice, but was lower than the MTD in females.
    The above study was reevaluated since the increase in the MFO at 3 
months in females was not considered to be significant enough to 
establish an LOEL. The LOEL was raised to 500 ppm (70.2 mg/kg/day for 
males and 85.2 mg/kg/day for females) based on increases in MFO in both 
sexes, increases in SGPT values in females and in absolute and relative 
liver weights in both sexes at 3 months, increased incidences and 
severity of centrilobular hepatocytic hypertrophy, Kupffer cell 
pigmentation, periportal punctate vacuolation and individual 
hepatocellular necrosis in males, and increased incidences of focal 
hepatocellular alteration and multifocal hepatocellular vacuolation in 
both sexes. The NOEL has been raised to 100 ppm (13.7 mg/kg/day for 
males and 16.5 mg/kg/day for females).
    An 18-month study was conducted with female mice using a dose level 
of 2,000 ppm, which approaches the MTD, to evaluate the carcinogenic 
potential in female mice. In this study, a NOEL could not be 
established because there were effects at the only dose level tested. 
These effects included: decreases in body weight and body weight gain, 
increases in liver weights, hepatocellular hypertrophy, hepatocellular 
vacuolation, necrosis of single hypertrophied hepatocytes, yellow-brown 
pigment in the Kupffer cells, and cytoplasmic eosinophilia and 
hypertrophy of the cells of the zona fasciculata area of the adrenal 
cortex. Myclobutanil was not oncogenic when tested under the conditions 
of the study.
    4. A rabbit developmental toxicity study at dosages of 0, 20, 60, 
and 200 mg/kg/day administered by oral gavage. The LOEL for maternal 
toxicity was 200 mg/kg/day, and the maternal toxicity NOEL was 60 mg/
kg/day based on reduced body weight and body weight gain during the 
dosing period, clinical signs of toxicity, and possibly abortions. THE 
LOEL for developmental toxicity is 200 mg/kg/day and NOEL for 
developmental toxicity is 60 mg/kg/day based on increases in 
resorptions, decreases in litter size, and a decrease in the viability 
index.
    5. A developmental toxicity study on rats treated with dosages of 
0, 31.26, 93.77, 312.58, and 468.87 mg/kg/day. The maternal toxicity 
LOEL was 312.6 mg/kg/day, and maternal toxicity NOEL was 93.8 mg/kg/day 
based on clinical signs of toxicity. The developmental toxicity LOEL 
was 312.6 mg/kg/day, and the developmental toxicity NOEL was 93.8 mg/
kg/day based on increased incidences of 14th rudimentary and 7th 
cervical ribs.
    6. A two-generation rat reproduction study with dosage rates of 0, 
50, 200, and 1,000 ppm (equivalent to 0, 2.5, 10, and 50 mg/kg/day). 
The parental (systemic) toxicity LOEL was 200 ppm (10 mg/kg/day) and 
the parental (systemic) toxicity NOEL was 50 ppm (2.5 mg/kg/day) based 
on hepatocellular hypertrophy and increases in liver weights. The 
reproductive toxicity LOEL was 1,000 ppm (50 mg/kg/day), and 
reproductive toxicity NOEL was 200 ppm (10 mg/kg/day) based on an 
increased incidence in the number of stillborns and atrophy of the 
testes and prostate. The developmental toxicity LOEL was 1,000 ppm (50 
mg/kg/day), and the developmental toxicity NOEL was 200 ppm (10 mg/kg/
day) based on a decrease in pup body weight gain during lactation.
    7. A reverse mutation assay (Ames), point mutation in CHO/HGPRT 
cells, in vitro and in vivo (mouse) cytogenetic assays, unscheduled DNA 
synthesis, and a dominant-lethal study in rats, all of which were 
negative for mutagenic effects.
    The Reference Dose (RfD) based on the 2-year rat chronic feeding 
study (NOEL of 2.49 mg/kg bwt/day) and using a hundredfold uncertainty 
factor is calculated to be 0.025 mg/kg bwt/day. The theoretical maximum 
residue contribution (TMRC) from previously established tolerances and 
tolerances established here is 0.002319 mg/kg bwt/day for the general 
population and utilizes 9% of the RfD. The percentages of the RfD for 
the most highly exposed subgroups, nonnursing infants (less than 1 year 
old) and children (1 to 6 years old), are 58% and 25%, respectively. 
The TMRC was calculated based on the assumption that myclobutanil 
occurs at the maximum legal limit in all of the dietary commodities for 
which tolerances are proposed. Even with this probable large 
overestimate of exposure/risk, the TMRC is well below the RfD for the 
population as a whole and for each of the 22 subgroups considered. 
Thus, the dietary risk from exposure to myclobutanil appears to be 
minimal for the use on stone fruits.
    The nature of the residues is adequately understood and adequate 
[[Page 21738]] analytical methods, gas liquid chromatography using 
nitrogen/phosphorus and electron capture detectors, are available for 
enforcement. Prior to their publication in the Pesticide Analytical 
Manual, Vol. II, the enforcement methodology is being made available in 
the interim to anyone who is interested in pesticide enforcement when 
requested from: Calvin Furlow, Public Information Branch, Field 
Operations Division (7505C), Office of Pesticide Programs, 
Environmental Protection Agency, 401 M St., SW., Washington, DC 20460. 
Office location and telephone number: Rm 1128C, CM #2, 1921 Jefferson 
Davis Hwy, Arlington, VA 22202, (703)-305-5232.
    The pesticide is considered useful for the purpose for which the 
tolerances are sought. Based on the information and data considered, 
the Agency has determined that the tolerances established by amending 
40 CFR parts 180 and 185 will protect the public health. Therefore, the 
tolerances are established as set forth below. By way of public 
reminder, this document also reiterates the registrant's responsibility 
under section 6(a)(2) of FIFRA, to submit additional factual 
information regarding adverse effects on the environment and to human 
health by these pesticides.
    Any person adversely affected by this regulation may, within 30 
days after publication of this document in the Federal Register, file 
written objections to the regulation and may also request a hearing on 
those objections. Objections and hearing requests must be filed with 
the Hearing Clerk, at the address given above (40 CFR 178.20). A copy 
of the objections and/or hearing requests filed with the Hearing Clerk 
should be submitted to the OPP docket for this rulemaking. The 
objections submitted must specify the provisions of the regulation 
deemed objectionable and the grounds for the objections (40 CFR 
178.25). Each objection must be accompanied by the fee prescribed by 40 
CFR 180.33 (i). 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). A request for a 
hearing will be granted if the Administrator determines that the 
material submitted shows the following: There is 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 issues(s) in the manner sought by the 
requestor would be adequate to justify the action requested (40 CFR 
178.32).
     A record has been established for this rulemaking under docket 
number [PP 2F4116 and FAP 2H5644/R2124] (including any objections and 
hearing requests submitted electronically as described below). A public 
version of this record, including printed, paper versions of electronic 
comments, which does not include any information claimed as CBI, is 
available for inspection from 8 a.m. to 4:30 p.m., Monday through 
Friday, excluding legal holidays. The public record is located in Room 
1132 of the Public Response and Program Resources Branch, Field 
Operations Division (7506C), Office of Pesticide Programs, 
Environmental Protection Agency, Crystal Mall #2, 1921 Jefferson Davis 
Highway, Arlington, VA.
    Written objections and requests for hearings, identified by the 
document control number [PP 2F4116 and FAP 2H5644/R2124], may be 
submitted to the Hearing Clerk (1900), Environmental Protection Agency, 
Rm. 3708, 401 M St., SW., Washington, DC 20460.
    A copy of electronic objections and requests for hearings can be 
sent directly to EPA at:
    opp-D[email protected]


    A copy of electronic objections and requests for hearings must be 
submitted as an ASCII file avoiding the use of special characters and 
any form of encryption.
    The official record for this rulemaking, as well as the public 
version, as described above will be kept in paper form. Accordingly, 
EPA will transfer any copies of objections and requests for hearings 
received electronically into printed, paper form as they are received 
and will place the paper copies in the official rulemaking record which 
will also include all comments submitted directly in writing. The 
official rulemaking record is the paper record maintained at the 
address in ``ADDRESSES'' at the beginning of this document.
    Under Executive Order 12866 (58 FR 51735, October 4, 1993), the 
Agency must determine whether the regulatory action is ``significant'' 
and therefore subject to all the requirements of the Executive Order 
(i.e., Regulatory Impact Analysis, review by the Office of Management 
and Budget (OMB)). Under section 3(f), the order defines 
``significant'' as those actions likely to lead to a rule (1) having an 
annual effect on the economy of $100 million or more, or adversely and 
materially affecting a sector of the economy, productivity, 
competition, jobs, the environment, public health or safety, or State, 
local or tribal governments or communities (also known as 
``economically significant''); (2) creating serious inconsistency or 
otherwise interfering with an action taken or planned by another 
agency; (3) materially altering the budgetary impacts of entitlement, 
grants, user fees, or loan programs; or (4) raising novel legal or 
policy issues arising out of legal mandates, the President's 
priorities, or the principles set forth in this Executive Order.
    Pursuant to the terms of this Executive Order, EPA has determined 
that this rule is not ``significant'' and is therefore not subject to 
OMB review.
    Pursuant to the requirements of the Regulatory Flexibility Act 
(Pub. L. 96-354, 94 Stat. 1164, 5 U.S.C. 601-612), the Administrator 
has determined that regulations establishing new tolerances or raising 
tolerance levels or establishing exemptions from tolerance requirements 
do not have a significant economic impact on a substantial number of 
small entities. A certification statement to this effect was published 
in the Federal Register of May 4, 1981 (46 FR 24950).

List of Subjects in 40 CFR Parts 180 and 185

    Environmental protection, Administrative practice and procedure, 
Agricultural commodities, Pesticides and pests, Reporting and 
recordkeeping requirements.

    Dated: March 30, 1995.

Stephen L. Johnson,
Director, Registration Division, Office of Pesticide Programs.

    Therefore, chapter I of the title 40 of the Code of Federal 
Regulations is amended as follows:

PART 180--[AMENDED]

    1. In part 180:
    a. The authority citation for part 180 continues to read as 
follows:

    Authority: 21 U.S.C. 346a and 371.

    b. In Sec. 180.443(a), by revising the table therein, to read as 
follows:


Sec. 180.443   Myclobutanil; tolerances for residues.

    (a) *  *  *

------------------------------------------------------------------------
                                                              Parts per 
                         Commodity                             million  
------------------------------------------------------------------------
Apples.....................................................          0.5
Cherries (sweet and sour)..................................          5.0
Grapes.....................................................          1.0
Stone fruits (except cherries).............................          2.0
------------------------------------------------------------------------

[[Page 21739]] * * * * *

PART 185--[AMENDED]

    2. In part 185:
    a. The authority citation for part 185 continues to read as 
follows:

    Authority: 21 U.S.C. 346a and 348.

    b. In section 185.4350, by revising the table therein, to read as 
follows:


Sec. 185.4350   Myclobutanil.

* * * * *

------------------------------------------------------------------------
                                                              Parts per 
                         Commodity                             million  
------------------------------------------------------------------------
Plums, dried...............................................          8.0
Raisins....................................................         10.0
------------------------------------------------------------------------


[FR Doc. 95-10861 Filed 5-2-95; 8:45 am]
BILLING CODE 6560-50-F