Federal Register / Vol. 76, No. 251 / Friday, December 30, 2011 / Rules and Regulations 82157 

V. Conclusion 

Therefore, tolerances are established 

for residues of cyhalofop-butyl, 

including its metabolites and 

degradates, as set forth in the regulatory 

text. 

VI. Statutory and Executive Order 

Reviews 

This final rule establishes tolerances 

under section 408(d) of FFDCA in 

response to a petition submitted to the 

Agency. The Office of Management and 

Budget (OMB) has exempted these types 

of actions from review under Executive 

Order 12866, entitled Regulatory 

Planning and Review (58 FR 51735, 

October 4, 1993). Because this final rule 

has been exempted from review under 

Executive Order 12866, this final rule is 

not subject to Executive Order 13211, 

entitled Actions Concerning Regulations 

That Significantly Affect Energy Supply, 

Distribution, or Use (66 FR 28355, May 

22, 2001) or Executive Order 13045, 

entitled Protection of Children from 

Environmental Health Risks and Safety 

Risks (62 FR 19885, April 23, 1997). 

This final rule does not contain any 

information collections subject to OMB 

approval under the Paperwork 

Reduction Act (PRA), 44 U.S.C. 3501 et 

seq., nor does it require any special 

considerations under Executive Order 

12898, entitled Federal Actions to 

Address Environmental Justice in 

Minority Populations and Low-Income 

Populations (59 FR 7629, February 16, 

1994). 

Since tolerances and exemptions that 

are established on the basis of a petition 

under section 408(d) of FFDCA, such as 

the tolerance in this final rule, do not 

require the issuance of a proposed rule, 

the requirements of the Regulatory 

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

seq.) do not apply. 

This final rule directly regulates 

growers, food processors, food handlers, 

and food retailers, not States or tribes, 

nor does this action alter the 

relationships or distribution of power 

and responsibilities established by 

Congress in the preemption provisions 

of section 408(n)(4) of FFDCA. As such, 

the Agency has determined that this 

action will not have a substantial direct 

effect on States or tribal governments, 

on the relationship between the national 

government and the States or tribal 

governments, or on the distribution of 

power and responsibilities among the 

various levels of government or between 

the Federal Government and Indian 

tribes. Thus, the Agency has determined 

that Executive Order 13132, entitled 

Federalism (64 FR 43255, August 10, 

1999) and Executive Order 13175, 

entitled Consultation and Coordination 

with Indian Tribal Governments (65 FR 

67249, November 9, 2000) do not apply 

to this final rule. In addition, this final 

rule does not impose any enforceable 

duty or contain any unfunded mandate 

as described under Title II of the 

Unfunded Mandates Reform Act of 1995 

(UMRA) (Pub. L. 104–4). 

This action does not involve any 

technical standards that would require 

Agency consideration of voluntary 

consensus standards pursuant to section 

12(d) of the National Technology 

Transfer and Advancement Act of 1995 

(NTTAA), Public Law 104–113, section 

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

VII. Congressional Review Act 

The Congressional Review Act, 5 

U.S.C. 801 et seq., generally provides 

that before a rule may take effect, the 

agency promulgating the rule must 

submit a rule report to each House of 

the Congress and to the Comptroller 

General of the United States. EPA will 

submit a report containing this rule and 

other required information to the U.S. 

Senate, the U.S. House of 

Representatives, and the Comptroller 

General of the United States prior to 

publication of this final rule in the 

Federal Register. This final rule is not 

a ‘‘major rule’’ as defined by 5 U.S.C. 

804(2). 

List of Subjects in 40 CFR Part 180 

Environmental protection, 

Administrative practice and procedure, 

Agricultural commodities, Pesticides 

and pests, Reporting and recordkeeping 

requirements. 

Dated: December 19, 2011. 

Lois Rossi, 

Director, Registration Division, Office of 

Pesticide Programs. 

Therefore, 40 CFR chapter I is 

amended as follows: 

PART 180—[AMENDED] 

■ 1. The authority citation for part 180 

continues to read as follows: 

Authority: 21 U.S.C. 321(q), 346a and 371. 

■ 2. Section 180.576 is amended by 

revising paragraph (a) to read as follows: 

§ 180.576 Cyhalofop-butyl; tolerances for 

residues. 

(a) General. Tolerances are 

established for residues of cyhalofopbutyl, including its metabolites and 

degradates, in or on the commodities 

listed in the table below. Compliance 

with the tolerance levels specified 

below is to be determined by measuring 

cyhalofop butyl [R-(+)-n-butyl-2-(4(4- 

cyano-2-fluorophenoxy)- 

phenoxy)propionate], cyhalofop acid [R- 

(+)-2-(4(4-cyano-2-fluorophenoxy)- 

phenoxy)propionic acid], and the diacid metabolite [(2R)-4-(4-(1- 

carboxyethoxy)phenoxy)-3- 

fluorobenzoic acid]. 

Commodity Parts per 

million 

Rice, grain ................................ 0.40 

Wild rice, grain .......................... 0.40 

* * * * * 

[FR Doc. 2011–33480 Filed 12–29–11; 8:45 am] 

BILLING CODE 6560–50–P 

ENVIRONMENTAL PROTECTION 

AGENCY 

40 CFR Part 180 

[EPA–HQ–OPP–2010–0959; FRL–9328–6] 

Difenoconazole; Pesticide Tolerances 

AGENCY: Environmental Protection 

Agency (EPA). 

ACTION: Final rule. 

SUMMARY: This regulation establishes 

tolerances for residues of 

difenoconazole in or on oat and rye 

commodities, and wheat, hay. Syngenta 

Crop Protection, Incorporated requested 

these tolerances under the Federal Food, 

Drug, and Cosmetic Act (FFDCA). 

DATES: This regulation is effective 

December 30, 2011. Objections and 

requests for hearings must be received 

on or before February 28, 2012, and 

must be filed in accordance with the 

instructions provided in 40 CFR part 

178 (see also Unit I.C. of the 

SUPPLEMENTARY INFORMATION). 

ADDRESSES: EPA has established a 

docket for this action under docket 

identification (ID) number EPA–HQ– 

OPP–2010–0959. All documents in the 

docket are listed in the docket index 

available at http://www.regulations.gov. 

Although listed in the index, some 

information is not publicly available, 

e.g., Confidential Business Information 

(CBI) or other information whose 

disclosure is restricted by statute. 

Certain other material, such as 

copyrighted material, is not placed on 

the Internet and will be publicly 

available only in hard copy form. 

Publicly available docket materials are 

available in the electronic docket at 

http://www.regulations.gov, or, if only 

available in hard copy, at the OPP 

Regulatory Public Docket in Rm. 

S–4400, One Potomac Yard (South 

Bldg.), 2777 S. Crystal Dr., Arlington, 

VA. The Docket Facility is open from 

8:30 a.m. to 4 p.m., Monday through 


tkelley on DSK3SPTVN1PROD with RULES
82158 Federal Register / Vol. 76, No. 251 / Friday, December 30, 2011 / Rules and Regulations 

Friday, excluding legal holidays. The 

Docket Facility telephone number is 

(703) 305–5805. 

FOR FURTHER INFORMATION CONTACT: 

Tony Kish, Registration Division, Office 

of Pesticide Programs, Environmental 

Protection Agency, 1200 Pennsylvania 

Ave. NW., Washington, DC 20460–0001; 

telephone number: (703) 308–9443; 

email address: kish.tony@epa.gov. 

SUPPLEMENTARY INFORMATION: 

I. General Information 

A. Does this action apply to me? 

You may be potentially affected by 

this action if you are an agricultural 

producer, food manufacturer, or 

pesticide manufacturer. Potentially 

affected entities may include, but are 

not limited to those engaged in the 

following activities: 

• Crop production (NAICS code 111). 

• Animal production (NAICS code 

112). 

• Food manufacturing (NAICS code 

311). 

• Pesticide manufacturing (NAICS 

code 32532). 

This listing is not intended to be 

exhaustive, but rather to provide a guide 

for readers regarding entities likely to be 

affected by this action. Other types of 

entities not listed in this unit could also 

be affected. The North American 

Industrial Classification System 

(NAICS) codes have been provided to 

assist you and others in determining 

whether this action might apply to 

certain entities. If you have any 

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 electronic access to 

other related information? 

You may access a frequently updated 

electronic version of EPA’s tolerance 

regulations at 40 CFR part 180 through 

the Government Printing Office’s e-CFR 

site at http://ecfr.gpoaccess.gov/cgi/t/ 

text/text-idx?&c=ecfr&tpl=/ecfrbrowse/ 

Title40/40tab_02.tpl. 

C. How can I file an objection or hearing 

request? 

Under FFDCA section 408(g), 21 

U.S.C. 346a, any person may file an 

objection to any aspect of this regulation 

and may also request a hearing on those 

objections. You must file your objection 

or request a hearing on this regulation 

in accordance with the instructions 

provided in 40 CFR part 178. To ensure 

proper receipt by EPA, you must 

identify docket ID number EPA–HQ– 

OPP–2010–0959 in the subject line on 

the first page of your submission. All 

objections and requests for a hearing 

must be in writing, and must be 

received by the Hearing Clerk on or 

before February 28, 2012. Addresses for 

mail and hand delivery of objections 

and hearing requests are provided in 40 

CFR 178.25(b). 

In addition to filing an objection or 

hearing request with the Hearing Clerk 

as described in 40 CFR part 178, please 

submit a copy of the filing that does not 

contain any CBI for inclusion in the 

public docket. Information not marked 

confidential pursuant to 40 CFR part 2 

may be disclosed publicly by EPA 

without prior notice. Submit a copy of 

your non-CBI objection or hearing 

request, identified by docket ID number 

EPA–HQ–OPP–2010–0959, by one of 

the following methods: 

• Federal eRulemaking Portal: http:// 

www.regulations.gov. Follow the on-line 

instructions for submitting comments. 

• Mail: Office of Pesticide Programs 

(OPP) Regulatory Public Docket (7502P), 

Environmental Protection Agency, 1200 

Pennsylvania Ave. NW., Washington, 

DC 20460–0001. 

• Delivery: OPP Regulatory Public 

Docket (7502P), Environmental 

Protection Agency, Rm. S–4400, One 

Potomac Yard (South Bldg.), 2777 S. 

Crystal Dr., Arlington, VA. Deliveries 

are only accepted during the Docket 

Facility’s normal hours of operation 

(8:30 a.m. to 4 p.m., Monday through 

Friday, excluding legal holidays). 

Special arrangements should be made 

for deliveries of boxed information. The 

Docket Facility telephone number is 

(703) 305–5805. 

II. Summary of Petitioned-For 

Tolerances 

In the Federal Register of Wednesday, 

July 20, 2011 (76 FR 43231) (FRL–8880– 

1), EPA issued a notice pursuant to 

section 408(d)(3) of FFDCA, 21 U.S.C. 

346a(d)(3), announcing the filing of a 

pesticide petition (PP 0F7785) by 

Syngenta Crop Protection, Inc., P.O. Box 

18300, Greensboro, NC 27419. The 

petition requested that 40 CFR 180.475 

be amended by establishing tolerances 

for residues of the fungicide, 

difenoconazole, [1-[2-[2-chloro-4-(4- 

chlorophenoxy)phenyl]-4-methyl-1,3- 

dioxolan-2-ylmethyl]-1H-1,2,4-triazole], 

in or on oats, forage at 0.1ppm; oats, hay 

at 0.1 ppm; oats, straw at 0.1 ppm; oats, 

grain at 0.1 ppm; rye, forage at 0.1 ppm; 

rye, straw at 0.1 ppm; rye, grain at 0.1 

ppm; and wheat, hay at 0.1 ppm. That 

notice referenced a summary of the 

petition prepared by Syngenta Crop 

Protection, Inc., the registrant, which is 

available in the docket, http:// 

www.regulations.gov. 

One comment on the notice of filing 

was received from an anonymous 

submitter. EPA’s response to these 

comments is discussed in Unit IV.C. 

Based upon review of the data 

supporting this petition, EPA has 

revised the proposed tolerance levels for 

oat, grain; oat, forage; oat, hay; oat, 

straw; rye, grain; rye, forage; rye, straw; 

and wheat, hay. In addition, EPA 

modified commodity definitions 

submitted by the registrant, Syngenta 

Crop Protection, Inc. The reasons for 

these changes are explained in Unit 

IV.D. 

III. Aggregate Risk Assessment and 

Determination of Safety 

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

allows EPA to establish a tolerance (the 

legal limit for a pesticide chemical 

residue in or on a food) only if EPA 

determines that the tolerance is ‘‘safe.’’ 

Section 408(b)(2)(A)(ii) of FFDCA 

defines ‘‘safe’’ to mean that ‘‘there is a 

reasonable certainty that no harm will 

result from aggregate exposure to the 

pesticide chemical residue, including 

all anticipated dietary exposures and all 

other exposures for which there is 

reliable information.’’ This includes 

exposure through drinking water and in 

residential settings, but does not include 

occupational exposure. Section 

408(b)(2)(C)(ii)(I) of FFDCA requires 

EPA to give special consideration to 

exposure of infants and children to the 

pesticide chemical residue in 

establishing a tolerance and to ‘‘ensure 

that there is a reasonable certainty that 

no harm will result to infants and 

children from aggregate exposure to the 

pesticide chemical residue * * *’’. 

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

of FFDCA, and the factors specified in 

section 408(b)(2)(D) of FFDCA, EPA has 

reviewed the available scientific data 

and other relevant information in 

support of this action. EPA has 

sufficient data to assess the hazards of 

and to make a determination on 

aggregate exposure for difenoconazole 

including exposure resulting from the 

tolerances established by this action. 

EPA’s assessment of exposures and risks 

associated with difenoconazole follows. 

A. Toxicological Profile 

EPA has evaluated the available 

toxicity data and considered its validity, 

completeness, and reliability as well as 

the relationship of the results of the 

studies to human risk. EPA has also 

considered available information 

concerning the variability of the 

sensitivities of major identifiable 

subgroups of consumers, including 

infants and children. 


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Difenoconazole possesses low acute 

toxicity by the oral, dermal and 

inhalation routes of exposure. It is not 

an eye or skin irritant and is not a 

sensitizer. Subchronic and chronic 

studies with difenoconazole in mice and 

rats showed decreased body weights, 

decreased body weight gains and effects 

on the liver. In an acute neurotoxicity 

study in rats, reduced fore-limb grip 

strength was observed on day 1 in males 

and clinical signs of neurotoxicity were 

observed in females at the limit dose of 

2000 milligrams/kilograms (mg/kg). In a 

subchronic neurotoxicity study in rats, 

decreased hind limb strength was 

observed in males only at the mid- and 

high-doses. However, the effects 

observed in acute and subchronic 

neurotoxicity studies are transient, and 

the dose-response is well characterized 

with identified no-observed-adverseeffects-levels (NOAELs). No systemic 

toxicity was observed at the limit dose 

in the most recently submitted 28-day 

rat dermal toxicity study. 

There is no concern for increased 

qualitative an/or quantitative 

susceptibility after exposure to 

difenoconazole in developmental 

toxicity studies in rats and rabbits, and 

a reproduction study in rats as fetal/ 

offspring effects occurred in the 

presence of maternal toxicity. There are 

no indications in the available studies 

that organs associated with immune 

function, such as the thymus and 

spleen, are affected by difenoconazole. 

In accordance with the Agency’s 

current policy, difenoconazole is 

classified as ‘‘Suggestive Evidence of 

Carcingenic Potential’’ and EPA is using 

the Margin of Exposure (MOE) approach 

to assess cancer risk. Difenoconazole is 

not mutagenic, and no evidence of 

carcinogenicity was seen in rats. 

Evidence for carcinogenicity was seen 

in mice (liver tumors), but statistically 

significant carcinomas tumors were only 

induced at excessively-high doses. 

Adenomas (benign tumors) and liver 

necrosis only were seen at 300 parts per 

million (ppm) (46 and 58 mg/kg/day in 

males and females, respectively). Based 

on excessive toxicity observed the two 

highest doses in the study, the presence 

of only benign tumors and necrosis at 

the mid-dose, the absence of tumors at 

the study’s lower doses, and the absence 

of genotoxic effects, EPA has concluded 

that the chronic point of departure 

(POD) from the chronic mouse study 

will be protective of any cancer effects. 

The POD from this study is the NOAEL 

of 30 ppm (4.7 and 5.6 mg/kg/day in 

males and females, respectively) which 

was chosen based upon only those 

biological endpoints which were 

relevant to tumor development (i.e., 

hepatocellular hypertrophy, liver 

necrosis, fatty changes in the liver and 

bile stasis). 

Specific information on the studies 

received and the nature of the adverse 

effects caused by difenoconazole as well 

as the NOAEL and the lowest-observedadverse-effect-level (LOAEL) from the 

toxicity studies can be found at http:// 

www.regulations.gov in document 

entitled, ‘‘Difenoconazole Human 

Health Risk Assessment for Amended 

Section 3 Registration to Add Seed 

Treatment Use on Oats and Rye and 

Establish a Tolerance in/on Wheat 

Hay,’’ dated October 27, 2011 at page 

number 25 in docket ID number EPA– 

HQ–OPP–2010–0959–0007. 

B. Toxicological Points of Departure/ 

Levels of Concern 

Once a pesticide’s toxicological 

profile is determined, EPA identifies 

toxicological points of departure (POD) 

and levels of concern to use in 

evaluating the risk posed by human 

exposure to the pesticide. For hazards 

that have a threshold below which there 

is no appreciable risk, the toxicological 

POD is used as the basis for derivation 

of reference values for risk assessment. 

PODs are developed based on a careful 

analysis of the doses in each 

toxicological study to determine the 

dose at which the NOAEL and the 

LOAEL. Uncertainty/safety factors are 

used in conjunction with the POD to 

calculate a safe exposure level— 

generally referred to as a populationadjusted dose (PAD) or a reference dose 

(RfD)—and a safe margin of exposure 

(MOE). For non-threshold risks, the 

Agency assumes that any amount of 

exposure will lead to some degree of 

risk. Thus, the Agency estimates risk in 

terms of the probability of an occurrence 

of the adverse effect expected in a 

lifetime. For more information on the 

general principles EPA uses in risk 

characterization and a complete 

description of the risk assessment 

process, see http://www.epa.gov/ 

pesticides/factsheets/riskassess.htm. 

A summary of the toxicological 

endpoints for difenoconazole used for 

human risk assessment is discussed in 

Unit III. B. of the final rule published in 

the Federal Register of June 15, 2011 

(76 FR 34877) (FRL–8876–4). 

C. Exposure Assessment 

1. Dietary exposure from food and 

feed uses. In evaluating dietary 

exposure to difenoconazole, EPA 

considered exposure under the 

petitioned-for tolerances as well as all 

existing difenoconazole tolerances in 40 

CFR 180.475. EPA assessed dietary 

exposures from difenoconazole in food 

as follows: 

i. Acute exposure. Quantitative acute 

dietary exposure and risk assessments 

are performed for a food-use pesticide, 

if a toxicological study has indicated the 

possibility of an effect of concern 

occurring as a result of a 1-day or single 

exposure. 

Such effects were identified for 

difenoconazole. In estimating acute 

dietary exposure, EPA used food 

consumption information from the 

United States Department of Agriculture 

(USDA) 1994–1996 and 1998 

Nationwide Continuing Surveys of Food 

Intake by Individuals (CSFII). As to 

residue levels in food, EPA used 

tolerance-level residues, 100 percent 

crop treated (PCT), and the available 

empirical or DEEMTM (ver. 7.81) default 

processing factors. 

ii. Chronic exposure. In conducting 

the chronic dietary exposure assessment 

EPA used the food consumption data 

from the USDA 1994–1996 and 1998 

CSFII. As to residue levels in food, EPA 

assumed tolerance-level residues for 

some commodities, average field trial 

residues for the majority of 

commodities, the available empirical or 

DEEMTM (ver. 7.81) default processing 

factors, and 100 PCT. 

iii. Cancer. Based on the data 

summarized in Unit III.A., EPA has 

concluded that a nonlinear RfD 

approach is appropriate for assessing 

cancer risk to difenoconazole. A 

separate quantitative cancer exposure 

assessment is unnecessary since the 

NOAEL (4.7 and 5.6 mg/kg/day in males 

and females, respectively) to assess 

cancer risk is higher than the NOAEL 

(0.96 and 1.27 mg/kg/day in males and 

females, respectively) to assess chronic 

risks and exposure for the purpose of 

assessing cancer risk would be no 

higher than chronic exposure. 

Therefore, the chronic dietary risk 

estimate will be protective of potential 

cancer risk. 

iv. Anticipated residue and percent 

crop treated (PCT) information. EPA did 

not use PCT information in the dietary 

assessment for difenoconazole. EPA 

used anticipated residues in the form of 

average field trial residues for the 

majority of commodities. 

Section 408(b)(2)(E) of FFDCA 

authorizes EPA to use available data and 

information on the anticipated residue 

levels of pesticide residues in food and 

the actual levels of pesticide residues 

that have been measured in food. If EPA 

relies on such information, EPA must 

require pursuant to FFDCA section 

408(f)(1) that data be provided 5 years 

after the tolerance is established, 

modified, or left in effect, demonstrating 


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that the levels in food are not above the 

levels anticipated. For the present 

action, EPA will issue such data call-ins 

as are required by FFDCA section 

408(b)(2)(E) and authorized under 

FFDCA section 408(f)(1). Data will be 

required to be submitted no later than 

5 years from the date of issuance of 

these tolerances. 

2. Dietary exposure from drinking 

water. The Agency used screening level 

water exposure models in the dietary 

exposure analysis and risk assessment 

for difenoconazole in drinking water. 

These simulation models take into 

account data on the physical, chemical, 

and fate/transport characteristics of 

difenoconazole. Further information 

regarding EPA drinking water models 

used in pesticide exposure assessment 

can be found at http://www.epa.gov/ 

oppefed1/models/water/index.htm. 

Based on the Pesticide Root Zone 

Model/Exposure Analysis Modeling 

System (PRZM/EXAMS) for the 

registered and proposed new uses and 

Screening Concentration in Ground 

Water (SCI–GROW) models, the 

estimated drinking water concentrations 

(EDWCs) of difenoconazole for acute 

exposures are estimated to be 15.8 parts 

per billion (ppb) for surface water and 

0.0128 ppb for ground water. 

For chronic exposures for non-cancer 

assessments are estimated to be 10.4 

ppb for surface water and 0.0128 ppb for 

ground water. 

Modeled estimates of drinking water 

concentrations were directly entered 

into the dietary exposure model. 

For acute dietary risk assessment, the 

water concentration value of 15.8 ppb 

was used to assess the contribution to 

drinking water. 

For chronic dietary risk assessment, 

the water concentration of value 10.4 

ppb was used to assess the contribution 

to drinking water. 

3. From non-dietary exposure. The 

term ‘‘residential exposure’’ is used in 

this document to refer to nonoccupational, non-dietary exposure 

(e.g., for lawn and garden pest control, 

indoor pest control, termiticides, and 

flea and tick control on pets). 

Difenoconazole is currently registered 

for the following uses that could result 

in residential exposures: Ornamentals. 

EPA assessed residential exposure using 

the following assumptions: Adults may 

be exposed to difenoconazole from its 

currently registered use on ornamentals. 

Residential pesticide handlers may be 

exposed to short-term duration (1–30 

days) only. The dermal and inhalation 

(short-term) residential exposure was 

assessed for ‘‘homeowners’’ mixer/ 

loader/applicator wearing short pants 

and short-sleeved shirts as well as shoes 

plus socks using garden hose-end 

sprayer, ‘‘pump-up’’ compressed air 

sprayer, and backpack sprayer. 

Residential post-application exposure 

may occur from use of difenoconozole 

on golf course turf. Short-term dermal 

exposure was assessed for postapplication exposure to golf course turf. 

Further information regarding EPA 

standard assumptions and generic 

inputs for residential exposures may be 

found at http://www.epa.gov/pesticides/ 

trac/science/trac6a05.pdf. 

4. Cumulative effects from substances 

with a common mechanism of toxicity. 

Section 408(b)(2)(D)(v) of FFDCA 

requires that, when considering whether 

to establish, modify, or revoke a 

tolerance, the Agency consider 

‘‘available information’’ concerning the 

cumulative effects of a particular 

pesticide’s residues and ‘‘other 

substances that have a common 

mechanism of toxicity.’’ 

Difenoconazole is a member of the 

triazole-containing class of pesticides. 

Although conazoles act similarly in 

plants (fungi) by inhibiting ergosterol 

biosynthesis, there is not necessarily a 

relationship between their pesticidal 

activity and their mechanism of toxicity 

in mammals. Structural similarities do 

not constitute a common mechanism of 

toxicity. Evidence is needed to establish 

that the chemicals operate by the same, 

or essentially the same, sequence of 

major biochemical events (EPA, 2002). 

In conazoles, however, a variable 

pattern of toxicological responses is 

found. Some are hepatotoxic and 

hepatocarcinogenic in mice. Some 

induce thyroid tumors in rats. Some 

induce developmental, reproductive, 

and neurological effects in rodents. 

Furthermore, the conazoles produce a 

diverse range of biochemical events 

including altered cholesterol levels, 

stress responses, and altered DNA 

methylation. It is not clearly understood 

whether these biochemical events are 

directly connected to their toxicological 

outcomes. Thus, there is currently no 

evidence to indicate that conazoles 

share common mechanisms of toxicity 

and EPA is not following a cumulative 

risk approach based on a common 

mechanism of toxicity for the conazoles. 

For information regarding EPA’s 

procedures for cumulating effects from 

substances found to have a common 

mechanism of toxicity, see EPA’s Web 

sites at: http://www.epa.gov/pesticides/ 

cumulative and http://www.epa.gov/ 

fedrgstr/EPA_PEST/2002/January/ 

Day_16/. 

Difenoconazole is a triazole-derived 

pesticide. This class of compounds can 

form the common metabolite 1,2,4- 

triazole and two triazole conjugates 

(triazolylalanine and triazolylacetic 

acid). To support existing tolerances 

and to establish new tolerances for 

triazole-derivative pesticides, including 

difenoconazole, EPA conducted a 

human health risk assessment for 

exposure to 1,2,4-triazole, 

triazolylalanine, and triazolylacetic acid 

resulting from the use of all current and 

pending uses of any triazole-derived 

fungicide. The risk assessment is a 

highly conservative, screening-level 

evaluation in terms of hazards 

associated with common metabolites 

(e.g., use of a maximum combination of 

uncertainty factors) and potential 

dietary and non-dietary exposures (i.e., 

high end estimates of both dietary and 

non-dietary exposures). In addition, the 

Agency retained the additional 10× 

FQPA safety factor for the protection of 

infants and children. The assessment 

includes evaluations of risks for various 

subgroups, including those comprised 

of infants and children. The Agency’s 

risk assessment is found in the 

propiconazole reregistration docket at 

http://www.regulations.gov, Docket 

Identification (ID) Number EPA–HQ– 

OPP–2005–0497 and the most recent 

update that assessed additional new 

commodities for triazoles may be found 

in docket ID number EPA–HQ–OPP– 

2010–0959 in the document titled 

‘‘Common Triazole Metabolites: 

Updated Aggregate Human Health Risk 

Assessment to Address Tolerance 

Petitions for Metconazole’’, dated April 

27, 2011. The requested amended uses 

of difenoconazole did not result in an 

increase in dietary exposure estimates 

for free triazole or conjugated triazoles. 

Therefore, the last dietary exposure 

analyses cited above addresses potential 

exposures resulting from commodities 

discussed in this action. 

D. Safety Factor for Infants and 

Children 

1. In general. Section 408(b)(2)(C) of 

FFDCA provides that EPA shall apply 

an additional tenfold (10×) margin of 

safety for infants and children in the 

case of threshold effects to account for 

prenatal and postnatal toxicity and the 

completeness of the database on toxicity 

and exposure unless EPA determines 

based on reliable data that a different 

margin of safety will be safe for infants 

and children. This additional margin of 

safety is commonly referred to as the 

FQPA Safety Factor (SF). In applying 

this provision, EPA either retains the 

default value of 10×, or uses a different 

additional safety factor when reliable 

data available to EPA support the choice 

of a different factor. 

2. Prenatal and postnatal sensitivity. 

EPA determined that the available data 


tkelley on DSK3SPTVN1PROD with RULES
Federal Register / Vol. 76, No. 251 / Friday, December 30, 2011 / Rules and Regulations 82161 

indicated no increased susceptibility of 

rats or rabbits to in utero and/or 

postnatal exposure to difenoconazole. In 

the prenatal developmental toxicity 

studies in rats and rabbits and the 2- 

generation reproduction study in rats, 

toxicity to the fetuses/offspring, when 

observed, occurred at equivalent or 

higher doses than in the maternal/ 

parental animals. In the prenatal 

developmental toxicity study in rats, 

maternal toxicity was manifested as 

decreased body weight gain and food 

consumption at the LOAEL of 85 mg/kg/ 

day; the NOAEL was 16 mg/kg/day. The 

developmental toxicity was manifested 

as alterations in fetal ossifications at 171 

mg/kg/day; the developmental NOAEL 

was 85 mg/kg/day. In a developmental 

toxicity study in rabbits, maternal and 

developmental toxicity were seen at the 

same dose level (75 mg/kg/day). 

Maternal toxicity in rabbits was 

manifested as decreased body weight 

gain and decreased food consumption, 

while developmental toxicity was 

manifested as decreased fetal weight. In 

a 2-generation reproduction study in 

rats, there were decreases in maternal 

body weight gain and decreases in body 

weights of F1 males at the LOAEL of 

12.5 mg/kg/day; the parental systemic 

and off spring toxicity NOAEL was 1.25 

mg/kg/day. 

3. Conclusion. EPA has determined 

that reliable data show the safety of 

infants and children would be 

adequately protected if the FQPA SF 

were reduced to 1× . That decision is 

based on the following findings: 

i. The toxicity database is complete 

except for an immunotoxicity study 

which is now required as a part of new 

data requirements in the 40 CFR part 

158 for conventional pesticide 

registration. However, the toxicology 

database for difenoconazole does not 

show any evidence of treatment-related 

effects on the immune system. The 

overall weight of evidence suggests that 

this chemical does not directly target 

the immune system. Accordingly, the 

Agency does not believe that conducting 

a functional immunotoxicity study will 

result in a lower point of departure POD 

than that currently in use for overall risk 

assessment, and therefore, a database 

uncertainty factor is not needed to 

account for lack of this study. 

ii. The acute and subchronic 

neurotoxicity studies in rats are 

available. These data show that 

difenoconazole exhibits some evidence 

of neurotoxicity, but the effects are 

transient or occur at the limit dose. EPA 

concluded that difenoconazole is not a 

neurotoxic compound. Based on the 

toxicity profile, and lack of 

neurotoxicity, a developmental 

neurotoxicity study in rats is not 

required. 

iii. There is no evidence that 

difenoconazole results in increased 

susceptibility of rats or rabbit fetuses to 

in utero and/or postnatal exposure in 

the developmental and reproductive 

toxicity data. 

iv. There are no residual uncertainties 

identified in the exposure databases. A 

conservative dietary food exposure 

assessment was conducted. Acute 

dietary food exposure assessments were 

performed based on tolerance-level 

residues, 100 PCT, and the available 

empirical or DEEM (ver. 7.81) default 

processing factors. 

Chronic dietary exposure assessments 

were based on tolerance-level residues 

for some commodities, average field 

trial residues for the majority of 

commodities, the available empirical or 

DEEM (ver. 7.81) default processing 

factors, and 100 PCT. These are 

conservative approaches and are 

unlikely to understate the residues in 

food commodities. 

EPA also made conservative 

(protective) assumptions in the ground 

water and surface water modeling used 

to assess exposure to difenoconazole in 

drinking water. Post-application 

residential exposure of children is not 

expected. These assessments will not 

underestimate the exposure and risks 

posed by difenoconazole. 

E. Aggregate Risks and Determination of 

Safety 

EPA determines whether acute and 

chronic dietary pesticide exposures are 

safe by comparing aggregate exposure 

estimates to the aPAD and chronic PAD 

(cPAD). For linear cancer risks, EPA 

calculates the lifetime probability of 

acquiring cancer given the estimated 

aggregate exposure. Short-, 

intermediate-, and chronic-term risks 

are evaluated by comparing the 

estimated aggregate food, water, and 

residential exposure to the appropriate 

PODs to ensure that an adequate MOE 

exists. 

1. Acute risk. Using the exposure 

assumptions discussed in this unit for 

acute exposure, the acute dietary 

exposure from food and water to 

difenoconazole will occupy 19% of the 

aPAD for children 1 to 2 years old, the 

population group receiving the greatest 

exposure. 

2. Chronic risk. Using the exposure 

assumptions described in this unit for 

chronic exposure, EPA has concluded 

that chronic exposure to difenoconazole 

from food and water will utilize 46% of 

the cPAD for children 1 to 2 years old, 

the population group receiving the 

greatest exposure. Based on the 

explanation in Unit III.C.3., regarding 

residential use patterns, chronic 

residential exposure to residues of 

difenoconazole is not expected. 

3. Short-term risk. Short-term 

aggregate exposure takes into account 

short-term residential exposure plus 

chronic exposure to food and water 

(considered to be a background 

exposure level). 

Difenoconazole is currently registered 

for uses on ornamentals that could 

result in short-term residential 

exposure, and the Agency has 

determined that it is appropriate to 

aggregate chronic exposure through food 

and water with short-term residential 

exposures to difenoconazole. 

Using the exposure assumptions 

described in this unit for short-term 

exposures, EPA has concluded the 

combined short-term food, water, and 

residential exposures result in aggregate 

MOEs of 260 or greater. Because EPA’s 

level of concern for difenoconazole is a 

MOE of 100 or below, these MOEs 

resulting from short-termed exposure to 

difenoconazole are not of concern. 

4. Intermediate-term risk. 

Intermediate-term aggregate exposure 

takes into account intermediate-term 

residential exposure plus chronic 

exposure to food and water (considered 

to be a background exposure level). 

An intermediate-term adverse effect 

was identified; however, difenoconazole 

is not registered for any use patterns 

that would result in intermediate-term 

residential exposure. Intermediate-term 

risk is assessed based on intermediateterm residential exposure plus chronic 

dietary exposure. Because there is no 

intermediate-term residential exposure 

and chronic dietary exposure has 

already been assessed under the 

appropriately protective cPAD (which is 

at least as protective as the POD used to 

assess intermediate-term risk), no 

further assessment of intermediate-term 

risk is necessary, and EPA relies on the 

chronic dietary risk assessment for 

evaluating intermediate-term risk for 

difenoconazole. 

5. Aggregate cancer risk for U.S. 

population. As discussed in Unit III.A., 

the chronic dietary risk assessment is 

protective of any potential cancer 

effects. 

6. Determination of safety. Based on 

these risk assessments, EPA concludes 

that there is a reasonable certainty that 

no harm will result to the general 

population, or to infants and children 

from aggregate exposure to 

difenoconazole residues. 


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82162 Federal Register / Vol. 76, No. 251 / Friday, December 30, 2011 / Rules and Regulations 

IV. Other Considerations 

A. Analytical Enforcement Methodology 

An adequate enforcement method, gas 

chromatography with nitrogen/ 

phosphorus detection (GC/NPD) method 

AG–575B, is available for the 

determination of residues of 

difenoconazole per se in/on plant 

commodities. An adequate enforcement 

method, liquid chromatography coupled 

with tandem mass spectrometry (LC/ 

MS/MS) method REM 147.07b, is 

available for the determination of 

residues of difenoconazole and CGA– 

205375 in livestock commodities. 

The methods may be requested from: 

Chief, Analytical Chemistry Branch, 

Environmental Science Center, 701 

Mapes Rd., Ft. Meade, MD 20755–5350; 

telephone number: (410) 305–2905; 

email address: 

residuemethods@epa.gov. 

B. International Residue Limits 

In making its tolerance decisions, EPA 

seeks to harmonize U.S. tolerances with 

international standards whenever 

possible, consistent with U.S. food 

safety standards and agricultural 

practices. EPA considers the 

international maximum residue limits 

(MRLs) established by the Codex 

Alimentarius Commission (Codex), as 

required by FFDCA section 408(b)(4). 

The Codex Alimentarius is a joint U.N. 

Food and Agriculture Organization/ 

World Health Organization food 

standards program, and it is recognized 

as an international food safety 

standards-setting organization in trade 

agreements to which the United States 

is a party. EPA may establish a tolerance 

that is different from a Codex MRL; 

however, FFDCA section 408(b)(4) 

requires that EPA explain the reasons 

for departing from the Codex level. 

Codex maximum residue limits 

(MRLs) for residues of difenoconazole 

have been established. However, since 

no Codex MRLs have been established 

for residues of difenoconazole in/on oat 

commodities, rye commodities, and 

wheat hay, harmonization with Codex is 

not an issue. Canadian MRLs for 

residues of difenoconazole have been 

established at 0.01 ppm for oat grain 

and 0.01 ppm for rye grain and U.S. 

tolerances for oat grain and rye grain are 

harmonization with these established 

Canadian MRLs. Mexican MRLs for 

residues of difenoconazole have been 

established; however, no Mexican MRLs 

have been established for any of the 

cereal grain commodities. 

C. Response to Comments 

One comment was received from a 

private citizen who opposed 

authorization by EPA to allow pesticide 

use on oats and other petitioned-for uses 

that would result in any pesticide 

residue on food. The Agency has 

received this same comment on 

numerous previous occasions and 

rejects it for the reasons previously 

stated in the Federal Register at 70 FR 

1349, January 7, 2005. 

D. Revisions to Petitioned-For 

Tolerances 

EPA determined that the proposed 

tolerance for oat, grain at 0.1 ppm 

should be established at 0.01 ppm. This 

decision was based on the translation 

and re-evaluation of available barley 

grain data. No detectable residues of 

difenoconazole are expected in/on oat 

grain from the maximum seed treatment 

use under consideration. Therefore, the 

tolerance should be established at the 

limit of quantitation (LOQ) of the 

current enforcement method, 0.01 ppm 

in/on oat grain. EPA increased the 

proposed tolerance in/on oat, forage 

from 0.1 ppm to 0.15 ppm based on the 

translation and re-evaluation of 

available wheat forage data; using the 

Organization for Economic Cooperation 

and Development (OECD) MRL 

calculator, a tolerance of 0.15 ppm is 

appropriate. For both oat, hay and oat, 

straw EPA decreased the proposed 

tolerances of 0.1 ppm to 0.05 ppm based 

on the translation and re-evaluation of 

available wheat hay and wheat straw 

data; residues of difenoconazole are not 

expected to exceed the LOQ of the 

current enforcement method, 0.05 ppm 

in/on oat straw or hay. 

EPA determined that the proposed 

tolerance for rye, grain at 0.1 ppm 

should be established at 0.01 ppm. This 

decision was based on the translation 

and re-evaluation of available wheat 

grain data. No detectable residues of 

difenoconazole are expected in/on rye 

grain; therefore, the tolerance should be 

established at the LOQ of the current 

enforcement method, 0.01 ppm in/on 

rye grain. Also, the EPA recommended 

tolerance for rye, grain at 0.01 ppm 

replaces the existing difenoconazole 

import only tolerance for rye, grain 0.1 

ppm. EPA increased the proposed 

tolerance for rye, forage from 0.1 ppm to 

0.15 ppm based on the translation and 

re-evaluation of available wheat forage 

data; using the OECD MRL calculator, a 

tolerance of 0.15 ppm is appropriate. 

For rye, straw, EPA decreased the 

proposed tolerance of 0.1 ppm to 0.05 

ppm based on the translation and reevaluation of available wheat straw 

data; residues of difenoconazole are not 

expected to exceed the LOQ of the 

current enforcement method, 0.05 ppm 

in/on rye straw. 

For wheat, hay, EPA decreased the 

proposed tolerance of 0.1 ppm to 0.05 

ppm based on the re-evaluation of 

available wheat hay data; residues of 

difenoconazole are not expected to 

exceed the LOQ of the current 

enforcement method, 0.05 ppm in/on 

wheat hay. 

V. Conclusion 

Therefore, tolerances are established 

for residues of difenoconazole, 

including its metabolites and 

degradates, in or on the commodities 

listed in the table at the end of this 

document. Compliance with the 

tolerance levels specified in the table 

below is to be determined by measuring 

only difenoconazole, 1-[2-[2-chloro-4-(4- 

chlorophenoxy)phenyl]-4-methyl-1,3- 

dioxolan-2-ylmethyl]-1H–1,2,4-triazole, 

in or on oat, forage at 0.15 ppm; oat, 

grain at 0.01 ppm; oat, hay at 0.05 ppm; 

oat, straw at 0.05 ppm; rye, forage at 

0.15 ppm; rye, grain at 0.01 ppm; rye, 

straw at 0.05 ppm; and wheat, hay at 

0.05 ppm. 

VI. Statutory and Executive Order 

Reviews 

This final rule establishes tolerances 

under section 408(d) of FFDCA in 

response to a petition submitted to the 

Agency. The Office of Management and 

Budget (OMB) has exempted these types 

of actions from review under Executive 

Order 12866, entitled Regulatory 

Planning and Review (58 FR 51735, 

October 4, 1993). Because this final rule 

has been exempted from review under 

Executive Order 12866, this final rule is 

not subject to Executive Order 13211, 

entitled Actions Concerning Regulations 

That Significantly Affect Energy Supply, 

Distribution, or Use (66 FR 28355, May 

22, 2001) or Executive Order 13045, 

entitled Protection of Children from 

Environmental Health Risks and Safety 

Risks (62 FR 19885, April 23, 1997). 

This final rule does not contain any 

information collections subject to OMB 

approval under the Paperwork 

Reduction Act (PRA), 44 U.S.C. 3501 et 

seq., nor does it require any special 

considerations under Executive Order 

12898, entitled Federal Actions to 

Address Environmental Justice in 

Minority Populations and Low-Income 

Populations (59 FR 7629, February 16, 

1994). 

Since tolerances and exemptions that 

are established on the basis of a petition 

under section 408(d) of FFDCA, such as 

the tolerance in this final rule, do not 

require the issuance of a proposed rule, 

the requirements of the Regulatory 

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

seq.) do not apply. 


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Federal Register / Vol. 76, No. 251 / Friday, December 30, 2011 / Rules and Regulations 82163 

This final rule directly regulates 

growers, food processors, food handlers, 

and food retailers, not States or tribes, 

nor does this action alter the 

relationships or distribution of power 

and responsibilities established by 

Congress in the preemption provisions 

of section 408(n)(4) of FFDCA. As such, 

the Agency has determined that this 

action will not have a substantial direct 

effect on States or tribal governments, 

on the relationship between the national 

government and the States or tribal 

governments, or on the distribution of 

power and responsibilities among the 

various levels of government or between 

the Federal Government and Indian 

tribes. Thus, the Agency has determined 

that Executive Order 13132, entitled 

Federalism (64 FR 43255, August 10, 

1999) and Executive Order 13175, 

entitled Consultation and Coordination 

with Indian Tribal Governments (65 FR 

67249, November 9, 2000) do not apply 

to this final rule. In addition, this final 

rule does not impose any enforceable 

duty or contain any unfunded mandate 

as described under Title II of the 

Unfunded Mandates Reform Act of 1995 

(UMRA) (Pub. L. 104–4). 

This action does not involve any 

technical standards that would require 

Agency consideration of voluntary 

consensus standards pursuant to section 

12(d) of the National Technology 

Transfer and Advancement Act of 1995 

(NTTAA), Public Law 104–113, section 

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

VII. Congressional Review Act 

The Congressional Review Act, 5 

U.S.C. 801 et seq., generally provides 

that before a rule may take effect, the 

agency promulgating the rule must 

submit a rule report to each House of 

the Congress and to the Comptroller 

General of the United States. EPA will 

submit a report containing this rule and 

other required information to the U.S. 

Senate, the U.S. House of 

Representatives, and the Comptroller 

General of the United States prior to 

publication of this final rule in the 

Federal Register. This final rule is not 

a ‘‘major rule’’ as defined by 5 U.S.C. 

804(2). 

List of Subjects in 40 CFR Part 180 

Environmental protection, 

Administrative practice and procedure, 

Agricultural commodities, Pesticides 

and pests, Reporting and recordkeeping 

requirements. 

Dated: December 21, 2011. 

Lois Rossi, 

Director, Registration Division, Office of 

Pesticide Programs. 

Therefore, 40 CFR chapter I is 

amended as follows: 

PART 180—[AMENDED] 

■ 1. The authority citation for part 180 

continues to read as follows: 

Authority: 21 U.S.C. 321(q), 346a and 371. 

■ 2. In § 180.475 the table to paragraph 

(a) is amended by alphabetically adding 

oat, forage; oat, grain; oat, hay; oat, 

straw; rye, forage; rye, straw; and wheat, 

hay and by revising the entry for rye, 

grain to read as follows: 

§ 180.475 Difenoconazole; tolerance for 

residues. 

(a) * * * 

(1) * * * 

Commodity Parts per 

million 

* * * * * 

Oat, forage ................................ 0.15 

Oat, grain .................................. 0.01 

Oat, hay .................................... 0.05 

Oat, straw ................................. 0.05 

* * * * * 

Rye, forage ............................... 0.15 

Rye, grain ................................. 0.01 

Rye, straw ................................. 0.05 

* * * * * 

Wheat, hay ............................... 0.05 

* * * * * 

[FR Doc. 2011–33482 Filed 12–29–11; 8:45 am] 

BILLING CODE 6560–50–P 

DEPARTMENT OF TRANSPORTATION 

Pipeline and Hazardous Materials 

Safety Administration 

49 CFR Parts 172, 173, 175, and 176 

[Docket No. PHMSA–2009–0126 (HM–215K)] 

RIN 2137–AE76 

Hazardous Materials: Harmonization 

With the United Nations 

Recommendations on the Transport of 

Dangerous Goods: Model Regulations, 

International Maritime Dangerous 

Goods Code, and the International 

Civil Aviation Organization Technical 

Instructions for the Safe Transport of 

Dangerous Goods by Air 

AGENCY: Pipeline and Hazardous 

Materials Safety Administration 

(PHMSA), DOT. 

ACTION: Final rule. 

SUMMARY: This document responds to 

administrative appeals, provides 

clarifications, and corrects 

typographical and other minor errors 

adopted in an international 

harmonization final rule published 

January 19, 2011 (HM–215K; 76 FR 

3308). The final rule amended the 

Hazardous Materials Regulations (HMR) 

by revising, removing or adding proper 

shipping names, the hazard class of a 

material, packing group assignments, 

special provisions, packaging 

authorizations, packaging sections, air 

transport quantity limitations, and 

vessel stowage requirements. The 

amendments were necessary to align the 

HMR with recent revisions to 

international standards for the transport 

of hazardous materials by all modes. 

DATES: Effective Date: January 1, 2012. 

Voluntary compliance date: PHMSA 

is authorizing voluntary compliance 

beginning December 30, 2011. 

ADDRESSES: For access to the docket to 

read background documents, including 

those referenced in this document, or to 

read comments received, go to http:// 

www.regulations.gov at any time and 

insert ‘‘PHMSA–2009–0126’’ in the 

‘‘Keyword’’ box, and then click 

‘‘Search.’’ You may also view the docket 

online by visiting the Docket 

Management Facility in Room W12– 

140, DOT Building, 1200 New Jersey 

Avenue SE., Washington, DC, between 9 

a.m. and 5 p.m., e.t. Monday through 

Friday, except Federal holidays. 

Anyone is able to search the 

electronic form for all comments 

received into any of our dockets by the 

name of the individual submitting the 

comment (or signing the comment, if 

submitted on behalf of an association, 

business, labor union, etc.). You may 

review the U.S. Department of 

Transportation’s (DOT) complete 

Privacy Act Statement in the Federal 

Register published on January 17, 2008 

(73 FR 3316), or you may visit http:// 

edocket.access.gpo.gov/2008/pdf/E8- 

785.pdf. 

FOR FURTHER INFORMATION CONTACT: 

Michael Stevens, telephone (202) 366– 

8553, or Shane Kelley, telephone (202) 

366–0656, Standards and Rulemaking 

Division, telephone (202) 366–8553, 

Pipeline and Hazardous Materials Safety 

Administration, U.S. Department of 

Transportation, 1200 New Jersey 

Avenue SE., 2nd Floor, Washington, DC 

20590–0001. 

SUPPLEMENTARY INFORMATION: 

I. Background 

II. Administrative Appeals Filed in Response 

to the HM–215K Final Rule 


tkelley on DSK3SPTVN1PROD with RULES