[Federal Register Volume 60, Number 100 (Wednesday, May 24, 1995)]
[Rules and Regulations]
[Pages 27419-27421]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 95-12743]



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ENVIRONMENTAL PROTECTION AGENCY
40 CFR Part 180

[PP 2F4154/R2136; FRL-4955-3]
RIN 2070-AB78


Fenbuconazole; Pesticide Tolerances

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes a time-limited tolerance for 
combined residues of the fungicide fenbuconazole, alpha-[2-(4-
chlorophenyl)ethyl]-alpha-phenyl-3-(1H-1,2,4-triazole)-1-
propanenitrile, and its metabolites cis-5-(4-chlorophenyl)dihydro-3-
phenyl-3-(1H-1,2,4-triazole-1-ylmethyl)-2-3H-furanone and trans-5-(4-
chlorophenyl)dihydro-3-phenyl-3-(1H-1,2,4-triazole-1-ylmethyl)-2-3H-
furanone, expressed as fenbuconazole, in or on the raw agricultural 
commodity bananas (whole fruit) at 0.3 ppm of which not more than 0.05 
ppm is contained in the banana pulp. Rohm & Haas Co. submitted 
petitions for this regulation to establish a maximum permissible level 
for residues of the fungicide.

EFFECTIVE DATE: This regulation becomes effective May 24, 1995..

ADDRESSES: Written objections and hearing requests, identified by the 
document control number, [PP 2F4154/R2136], may be submitted to: 
Hearing Clerk (1900), Environmental Protection Agency, Rm. M3708, 401 M 
St., SW., Washington, DC 20460. Fees accompanying objections shall be 
labeled ``Tolerance Petition Fees'' and forwarded to: EPA Headquarters 
Accounting Operations Branch (Tolerance Fees), P.O. Box 360277M, 
Pittsburgh, PA 15251. A copy of any objections and hearing request 
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 (7505C), Office of Pesticide 
Programs, Environmental Protection Agency, 401 M St., SW., Washington, 
DC 20450. In person, bring copy of objections and hearing request to: 
Rm. 1132, CM #2, 1921 Jefferson Davis Hwy., Arlington, VA 22202.
    A copy of objections and hearing requests filed with the Hearing 
Clerk may also be submitted electronically by sending electronic mail 
(e-mail) to: [email protected]. Copies of objections and 
hearing requests must be submitted as an ASCII file avoiding the use of 
special characters and any form of encryption. Copies of objections and 
hearing requests will also be accepted on disks in WordPerfect in 5.1 
file format or ASCII file format. All copies of objections and hearing 
requests in electronic form must be identified by the docket number [PP 
2F4154/R2136]. No Confidential Business Information (CBI) should be 
submitted through e-mail. Electronic copies of objections and hearing 
requests 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: James M. Stone, Acting 
Product Manager (PM) 22, Registration Division, Environmental 
Protection Agency, 401 M St., SW., Washington, DC 20460. Office 
location and telephone number: Rm. 229, CM #2, 1921 Jefferson Davis 
Hwy., Arlington, VA 22202, (703)- 305-5540; e-mail: 
[email protected].

SUPPLEMENTARY INFORMATION: EPA issued a notice, published in the 
Federal Register of December 30, 1992 (57 FR 62334), which announced 
that Rohm & Haas, Agricultural Chemicals, Independence Mall West, 
Philadelphia, PA 19105, had submitted a pesticide petition (PP) 2F4154, 
to EPA requesting that the Administrator, pursuant to section 408(d) of 
the Federal Food, Drug and Cosmetic Act (FFDCA), 21 U.S.C. 346a(d), 
amend 40 CFR part 180 by establishing a regulation to permit residues 
of fenbuconazole, alpha-[2-(4-chlorophenyl)ethyl]-alpha-phenyl-3-(1H-
1,2,4-triazole)-1-propanenitrile, and its metabolites [5-(4-
chlorophenyl)-dihydro-3-phenyl-3-(methyl-1H-1,2,4-triazole-1-yl)-2-3H-
furanone] in or on bananas (pulp) at 0.05 part per million (ppm) and 
bananas (peel) at 0.3 ppm. Subsequently, on June 29, 1994 (59 FR 
33503), EPA announced that Rohm & Haas had amended the petition to 
propose amending 40 CFR part 180 by establishing a regulation to permit 
residues of fenbuconazole, alpha-(2-(4-chlorophenyl)ethyl)-alpha-
phenyl-3-(1H-1,2,4-triazole)-1-propanenitrile, and its metabolites cis-
5-(4-chlorophenyl)dihydro-3-phenyl-3-(1H-1,2,4-triazole-1-4-ylmethyl)-
2-3H-furanone and trans-5-(4-chlorophenyl)dihydro-3-phenyl-3-(1H-1,2,4-
triazole-1-ylmethyl)-2-3H-furanone in or on bananas (whole fruit) at 
0.3 ppm of which not more than 0.05 ppm is contained in banana pulp.
    There were no comments or requests for referral to an advisory 
committee received in response to these notices of filing.
    The scientific data submitted in the petitions and all other 
relevant material have been evaluated. The toxicology data considered 
in support of the tolerances include:
    1. A rat acute oral study with an LD50 greater than 2 grams 
(g)/kilogram (kg).
    2. A 13-week rat feeding study with a no-observed-effect level 
(NOEL) of 20 ppm (1.3 milligrams(mg)/kg/day males and 1.5 mg/kg/day 
females) and a lowest-observed-effect level (LOEL) of 80 ppm (5.1 mg/
kg/day males and 6.3 mg/kg/day females) based on hepatotoxicity.
    3. A 3-month mouse feeding study with a NOEL of 20 ppm (3.8 mg/kg/
day males and 5.7 mg/kg/day females) and a LOEL of 60 ppm (11.1 mg/kg/
day males and 17.6 mg/kg/day females) based on hepatotoxicity.
    4. A 3-month dog feeding study with a NOEL of 100 ppm (3.3 mg/kg/
day males and 3.5 mg/kg/day females) and LOEL of 400 ppm (13.3 mg/kg/
day males and 14.0 mg/kg/day females), based hepatocellular 
hypertrophy.
    5. A 21-day rat dermal study with a NOEL greater than 1,000 mg/kg/
day (limit dose).
    6. A 78-week dietary carcinogenicity study in mice with a NOEL of 
1.43 mg/kg/day and a LOEL of 28.6 mg/kg/day (males) and 92.9 mg/kg/day 
(females) based on hepatocellular enlargement and a greater incidence 
and severity of hepatocellular vacuolation. There was evidence of 
carcinogenicity based on the occurrence of increased trend for 
malignant liver tumors in males and an increase in benign and malignant 
liver tumors in females. The carcinogenic effects observed are 
discussed below.
    7. A 24-month rat chronic feeding/carcinogenicity study with a NOEL 
of 80 ppm (3.03 mg/kg/day for males and 4.02 mg/kg/day for females) for 
systemic effects and an LEL of 800 ppm (30.62 mg/kg/day for males and 
43.07 mg/kg/day for females) based on decreased in body weights in 
females, and increased liver weighs in females and males along with 
hepatocellular enlargement and [[Page 27420]] vacuolization. There was 
also an increase in thyroid weights with slight increases in thyroid 
focal cystic hyperplasia and follicular cell neoplasia in both sexes. A 
LOEL was not established for males. There was evidence of 
carcinogenicity based on the increased occurrence of thyroid follicular 
cell benign and malignant tumors in males. The carcinogenic effects 
observed are discussed further below.
    8. A 24-month male rat chronic feeding/carcinogenicity study with a 
NOEL of less than 800 ppm (30.41 mg/kg/day) and a LOEL is 800 ppm 
(30.41 mg/kg/day) based on increased liver with centrilobular to 
midzonal hepatocellular enlargement and vacuolization, decreased body 
weight gain, and increased thyroid weights. There was evidence of 
carcinogenicity based on the increased occurrence of thyroid follicular 
cell benign and malignant tumors. The carcinogenic effects observed are 
discussed further below.
    9. A 1-year dog chronic feeding study with a NOEL of 150 ppm (3.75 
mg/kg/day) and the LOEL, based on decreases in body weight gain and 
increased liver weight, of 1,200 ppm (30 mg/kg/day).
    10. A two generation reproduction study in rats with a parental 
NOEL of 4 mg/kg/day (80 ppm) and a LOEL of 40 mg/kg/day (800 ppm), 
based on decreased body weight, decreased food consumption, increased 
number of dams not delivering viable or delivering nonviable offspring, 
and increases in adrenal and thyroid weights. The reproductive NOEL is 
greater than 40 mg/kg/day (800 ppm) [(highest dose tested (HDT)].
    11. A developmental toxicity study in rabbits with a maternal NOEL 
of 10 mg/kg/day, and a developmental NOEL of 30 mg/kg/day, and a 
maternal LOEL of 30 mg/kg/day due to only 1/19 (5%) of the pregnant 
does producing a viable fetus, and no developmental LOEL (greater than 
30 mg/kg/day).
    12. A developmental toxicity study in rats with a maternal NOEL and 
developmental NOEL of 30 mg/kg/day and a LEL of 75 mg/kg/day due to 
decrease in maternal body weight compared to controls and increase in 
early and late resorption with a decrease in number of live fetuses per 
dam.
    13. No evidence of gene mutation was observed in a test for 
induction of gene mutation at the HGPRT locus in Chinese hamster ovary 
cells. No increase in the number of cells with aberrations or 
observations per cell were noted in an in vivo cytogenetics assay using 
bone marrow from treated rats. No increase in unscheduled DNA synthesis 
in rat primary hepatocyte study was observed.
    14. A rat metabolism study showed that radiolabeled fenbuconazole 
is rapidly absorbed, distributed, and excreted following oral 
administration in rats. Biliary excretion data indicated that systemic 
absorption of fenbuconazole was high for all dosing groups. The feces 
was the major route of excretion. Tissue distribution and 
bioaccumulation of fenbuconazole appeared to be minimal.
    The Health Effects Division Carcinogenicity Peer Review Committee 
has concluded that the available data provide limited evidence of the 
carcinogenicity of fenbuconazole in mice and rats and has classified 
fenbuconazole as a Group C (possible human carcinogen with limited 
evidence of carcinogenicity in animals) in accordance with Agency 
guidelines, published in the Federal Register in 1986 (51 FR 33992; 
Sept. 24, 1986) and recommended that for the purpose of risk 
characterization a low-dose extrapolation model should be applied to 
the experimental animal tumor data for quantification for human risk 
(Q1*). This decision was based on the induction of thyroid 
follicular cell adenomas and/or combined adenomas-carcinomas in male 
rats in two studies, both by pairwise comparison with controls and by 
trend analysis. The studies were combined for the purpose of deriving 
the Q1*. The Q1* for fenbuconazole based on a recalculation 
with a 3/4's power safety factor is 1.06 X 10-2 (mg/kg/day)-1 
in human equivalents.
    Based on (1) the established pecan and stone fruit group (except 
plums and prunes) tolerances, (2) the limitation of production of the 
only fenbuconazole product registered under the Federal Insecticide, 
Fungicide, and Rodenticide Act (FIFRA) for use on stone fruit to 28,500 
pounds of active ingredient per year (calculated to be equivalent to 
treating 12.8% of the total U.S acreage of apricots, cherries, 
nectarines, and peaches per year), and (3) the proposed banana 
tolerances, the upper-bound limit of the dietary carcinogenic risk is 
calculated in the range of 1 incidence in 1 million (9 X 10-7).
    Processing studies for bananas are not required. Therefore, food/
feed additive tolerances are not needed in conjunction with these uses.
    Using the NOEL of 3.0 mg/kg/day from the most sensitive species in 
the rat chronic feeding study with a 100-fold safety factor, the 
Reference Dose (RfD) for systemic effects is 0.03 mg/kg/day. The 
theoretical maximum residue contribution (TMRC) from the established 
and proposed tolerances is 0.000616 mg/kg/day and utilizes 2 percent of 
the RfD for the overall U.S. population. For exposure of the most 
highly exposed subgroups in the population, non-nursing infants (less 
than 1-year old), the TMRC is 0.00522 mg/kg/day and utilizes 17 percent 
of the RfD.
    The metabolism of fenbuconazole in plants is adequately understood. 
Due to the following chemistry data gap, magnitude of the residue: Crop 
field trials with unbagged bananas (two in Hawaii and two in Puerto 
Rico) [GLN 171-4], EPA believes it is inappropriate to establish 
permanent tolerances for the uses of fenbuconazole at this time. 
However, based on trials with bagged bananas and one side-by-side trial 
with bagged and unbagged bananas, EPA believes that the existing data 
support time-limited tolerances to December 31, 1998.
    The nature of the residue in plants is adequately understood for 
the purposes of these time-limited tolerances. An analytical method, 
gas-liquid chromatography with a thermionic-specific detector with 
nitrogen selectivity, is available for enforcement purposes. The 
enforcement methodology has been submitted to the Food and Drug 
Administration for publication in the Pesticide Analytical Manual, Vol. 
II (PAM II). Because of the long lead time for publication of the 
method in PAM II, the analytical methodology is being made available in 
the interim to anyone interested in pesticide enforcement when 
requested from: Calvin Furlow, Public Response and Program Resources 
Branch, Field Operations Division (7506C), Office of Pesticide 
Programs, Environmental Protection Agency, 401 M St., SW., Washington, 
DC 20460. Office location and telephone number: Rm. 1132, CM #2, 1921 
Jefferson Davis Hwy., Arlington, VA 22202, (703)-305-5232.
    There is no reasonable expectation that secondary residues will 
occur in milk, eggs, or meat of livestock and poultry since there are 
no livestock feed items associated with this action. The pesticide is 
considered useful for the purpose for which the tolerance is sought. 
Based on the information and data considered, the Agency has determined 
that the time-limited tolerance established by amending 40 CFR part 180 
will protect the public health. Therefore, the tolerances are 
established as set forth below.
    Any person adversely affected by this regulation may, within 30 
days after publication of this document in the Federal Register, file 
written objections and/or request a hearing with the 
[[Page 27421]] 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 fees provided 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, and the requestor's contentions on each such issue, and a 
summary of the evidence relied upon by the objection (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 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).
     A record has been established for this rulemaking under docket 
number [PP 2F4154/R2136] (including 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 Rm. 1132, 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 hearing requests, identified by the document 
control number [PP 2F4154/R2136], 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 hearing requests filed with the 
Hearing Clerk can be sent directly to EPA at:
    opp-D[email protected]


    A copy of electronic objections and hearing requests filed with the 
Hearing Clerk 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 objections and hearing requests 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 objections and hearing requests 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 Part 180

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

    Dated: May 10, 1995.

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

    Therefore, 40 CFR part 180 is amended as follows:

PART 180--[AMENDED]

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

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

    b. In Sec. 180.480, by amending paragraph (a) in the table therein 
by adding and alphabetically inserting the raw agricultural commodity 
bananas, to read as follows:


Sec. 180.480   Fenbuconazole; tolerances for residues.

    (a) *  *  *

------------------------------------------------------------------------
             Commodity                        Parts per million         
------------------------------------------------------------------------
Bananas (whole fruit)..............  0.3 (of which not more than 0.05   
                                      ppm is contained in the banana    
                                      pulp).                            
                                                                        
                    *      *      *        *        *                   
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[FR Doc. 95-12743 Filed 5-23-95; 8:45 am]
BILLING CODE 6560-50-F