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[Federal Register Volume 60, Number 40 (Wednesday, March 1, 1995)]
[Rules and Regulations]
[Pages 11029-11032]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 95-5019]

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ENVIRONMENTAL PROTECTION AGENCY
40 CFR Part 180

[PP1F3989, 1F3995/R2109; FRL-4938-3]

RIN 2070-AB78

Pesticide Tolerances for Fenbuconazole

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes time-limited tolerances 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 
commodities pecans at 0.1 part per million (ppm) and stone fruit crop 
group (except plums and prunes) at 2.0 ppm. Rohm & Haas Co. submitted 
petitions requesting this regulation to establish maximum permissible 
levels for residues of the fungicide.

EFFECTIVE DATE: This regulation becomes effective on March 1, 1995.

ADDRESSES: Written objections and hearing requests, identified by the 
document control number, [PP 1F3989, 1F3995/R2109], 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 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. Fees accompanying objections shall be labeled ``Tolerance 
Petition Fees'' and forwarded to: EPA Headquarters Accounting 
Operations [[Page 11030]] Branch, OPP (Tolerance Fees), P.O. Box 
360277M, Pittsburgh, PA 15251.

FOR FURTHER INFORMATION CONTACT: By mail: Cynthia Giles-Parker, 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.

SUPPLEMENTARY INFORMATION: EPA issued a notice, published in the 
Federal Register of December 13, 1991 (56 FR 65080), which announced 
that Rohm and Haas, Agricultural Chemicals, Independence Mall West, 
Philadelphia, PA 19105, had submitted pesticide petition (PP) 1F3989 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) in or on stone fruit crop group and 
dried prunes at 2.0 ppm. In the Federal Register of March 2, 1994 (59 
FR 9985), EPA announced that Rohm and Haas had amended the petition to 
propose amending 40 CFR part 180 to establish a tolerance of 2.0 ppm in 
or on stone fruit crop group for 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.
    EPA issued a notice, published in the Federal Register of December 
13, 1991 (56 FR 65081), which announced that Rohm and Haas had filed 
pesticide petition (PP) 1F3995 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-(1-H-1,2,4-triazole)-1-
propanenitrile) in or on pecans at 0.1 ppm. In the Federal Register of 
March 2, 1994 (59 FR 9985), EPA announced that Rohm and Haas had 
amended the petition to propose amending 40 CFR part 180 to establish a 
tolerance of 0.1 ppm in or on pecans for 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, and alpha-[2-[4-chlorophenyl)-2-oxoethyl]-alpha-phenyl-1H-
1,2,4-triazole-1-propanenitrile. Rohm and Haas subsequently amended the 
petition to limit the stone fruit tolerances to stone fruit crop group 
(except plums and prunes). The Agency is editorially correcting the 
tolerance expression to read: 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 commodities pecans at 0.1 part per million (ppm) 
and stone fruit crop group (except plums and prunes) at 2.0 ppm.
    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 on hepatocellular 
hypertrophy.
    5. A 21-day rabbit 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 40 ppm (3.03 mg/kg/day for females and 4.02 mg/kg/day for males) for 
systemic effects and a LEL of 800 ppm (30.62 mg/kg/day for males and 
43.07 mg/kg/day for females) based on decreases in body weight gains 
and hepatocellular enlargement and vacuolization in females, and 
thyroid weight and histopathological changes in both sexes. 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 below.
    8. A 24-month male rat chronic feeding/carcinogenicity study with a 
NOEL of 800 ppm (30.41 mg/kg/day) and a LEL of 1,600 ppm (63.94 mg/kg/
day) based on increased liver and thyroid weights and lesions. There 
was evidence of carcinogenicity based on the increased occurrence of 
thyroid follicular cell benign and malignant tumors. The carcinogenic 
effects observed are discussed 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 and 
reproductive NOEL of 4 mg/kg/day (80 ppm) and a LOEL of 40 mg/kg/day 
(800 ppm), based on decreased body weight and food consumption, 
increased number of dams not delivering viable or delivering nonviable 
offspring, and increases in adrenal and thyroid/parathyroid weights.
    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 60 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 an 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 [[Page 11031]] 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 applied to the 
experimental animal tumor data should be used 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 pair-wise comparison with controls 
and by trend analysis. The studies were combined for the purpose of 
deriving the Q1*. The Q1* for fenbuconazole is 1.65 X 
10-2 (mg/kg/day)-1 in human equivalents.
    Based on assumptions that 100 percent of the pecan crop is treated 
and that residues are at the tolerance level, the upper-bound limit of 
the dietary carcinogenic risk for pecans is calculated in the range of 
1 incidence in 100 million (9.0 X 10-9). Based on assumption that 
stone fruit residues (except plums and prunes) are at the tolerance 
level and 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), the upper-bound limit of the dietary carcinogenic 
risk for stone fruit group except plums and prunes is calculated in the 
range of 1 incidence in 1 million (1 X 10-6).
    Processing studies for pecans and stone fruit other than plums and 
prunes 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 proposed 
tolerances is 0.000604 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, nonnursing infants (less than 1 year old), 
the TMRC is 0.00516 mg/kg/day and utilizes 17 percent of the RfD.
    The metabolism of fenbuconazole in plants is adequately understood. 
Due to a chemistry data gap for storage stability of fenbuconazole in 
other raw agricultural commodities [GLN 171-4(e)], EPA believes it is 
inappropriate to establish permanent tolerances for the uses of 
fenbuconazole at this time. However, based on apparent storage 
stability, 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 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 on 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).
    Under Executive Order 12866 (58 FR 51735, Oct. 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. [[Page 11032]] 
    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, Recording and 
recordkeeping requirements.

Dated: February 15, 1995.

Daniel M. Barolo,
Director, 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. By adding Sec. 180.480, to read as follows:

Sec. 180.480   Fenbuconazole; tolerances for residues.

    (a) Time-limited tolerances, to expire on December 31, 1998, are 
established 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 following raw 
agricultural commodities:

------------------------------------------------------------------------
                                                              Parts per 
                         Commodity                             million  
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Pecans.....................................................          0.1
Stone fruit crop group (except plums and prunes)...........          2.0
------------------------------------------------------------------------

    (b) Residues in these commodities not in excess of the established 
tolerance resulting from the uses described in paragraph (a) of this 
section remaining after expiration of the time-limited tolerance will 
not be considered to be actionable if the fungicide is applied during 
the term of and in accordance with the provisions of the above 
regulation.

[FR Doc. 95-5019 Filed 2-28-95; 8:45 am]
BILLING CODE 6560-50-F
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