37468 Federal Register / Vol. 78, No. 120 / Friday, June 21, 2013 / Rules and Regulations 

[FR Doc. C1–2013–12729 Filed 6–20–13; 8:45 am] 

BILLING CODE 1505–01–D 

ENVIRONMENTAL PROTECTION 

AGENCY 

40 CFR Part 180 

[EPA–HQ–OPP–2012–0177; FRL–9387–3] 

Cyproconazole; Pesticide Tolerances 

AGENCY: Environmental Protection 

Agency (EPA). 

ACTION: Final rule. 

SUMMARY: This regulation establishes 

tolerances for residues of cyproconazole 

in or on peanut and peanut, hay. 

Syngenta Crop Protection, LLC. 

requested these tolerances under the 

Federal Food, Drug, and Cosmetic Act 

(FFDCA). 

DATES: This regulation is effective June 

21, 2013. Objections and requests for 

hearings must be received on or before 

August 20, 2013, 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: The docket for this action, 

identified by docket identification (ID) 

number EPA–HQ–OPP–2012–0177, is 

available at http://www.regulations.gov 

or at the Office of Pesticide Programs 

Regulatory Public Docket (OPP Docket) 

in the Environmental Protection Agency 

Docket Center (EPA/DC), EPA West 

Bldg., Rm. 3334, 1301 Constitution Ave. 

NW., Washington, DC 20460–0001. The 

Public Reading Room is open from 8:30 

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

Friday, excluding legal holidays. The 

telephone number for the Public 

Reading Room is (202) 566–1744, and 

the telephone number for the OPP 

Docket is (703) 305–5805. Please review 

the visitor instructions and additional 

information about the docket available 

at http://www.epa.gov/dockets. 

FOR FURTHER INFORMATION CONTACT: 

Shaunta Hill, Registration Division 

(7505P), Office of Pesticide Programs, 

Environmental Protection Agency, 1200 

Pennsylvania Ave. NW., Washington, 

DC 20460–0001; telephone number: 

(703) 347–8961; email address: 

hill.shaunta@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. The following 

list of North American Industrial 

Classification System (NAICS) codes is 

not intended to be exhaustive, but rather 

provides a guide to help readers 

determine whether this document 

applies to them. Potentially affected 

entities may include: 

• Crop production (NAICS code 111). 

• Animal production (NAICS code 

112). 

• Food manufacturing (NAICS code 

311). 

• Pesticide manufacturing (NAICS 

code 32532). 

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 eCFR 

site at http://www.ecfr.gov/cgi-bin/textidx?&c=ecfr&tpl=/ecfrbrowse/Title40/ 

40tab_02.tpl. To access the OCSPP test 

guidelines referenced in this document 

electronically, please go to http:// 

www.epa.gov/ocspp and select ‘‘Test 

Methods and Guidelines.’’ 

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–2012–0177 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 August 20, 2013. 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 (excluding 

any Confidential Business Information 

(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 the non-CBI copy of your 

objection or hearing request, identified 

by docket ID number EPA–HQ–OPP– 

2012–0177, by one of the following 

methods: 

• Federal eRulemaking Portal: http:// 

www.regulations.gov. Follow the online 

instructions for submitting comments. 

Do not submit electronically any 

information you consider to be CBI or 

other information whose disclosure is 

restricted by statute. 

• Mail: OPP Docket, Environmental 

Protection Agency Docket Center (EPA/ 

DC), (28221T), 1200 Pennsylvania Ave. 

NW., Washington, DC 20460–0001. 

• Hand Delivery: To make special 

arrangements for hand delivery or 

delivery of boxed information, please 

follow the instructions at http:// 

www.epa.gov/dockets/contacts.htm. 

Additional instructions on commenting 

or visiting the docket, along with more 

information about dockets generally, is 

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

dockets. 

II. Summary of Petitioned-for Tolerance 

In the Federal Register of May 23, 

2012 (77 FR 30481) (FRL–9347–8), EPA 

issued a document pursuant to FFDCA 

section 408(d)(3), 21 U.S.C. 346a(d)(3), 

announcing the filing of a pesticide 

petition (PP 1F7956) by Syngenta Crop 

Protection, LLC., P.O. Box 18300, 

Greensboro, NC 24719. The petition 

requested that 40 CFR 180.485 be 

amended by establishing tolerances for 

residues of the fungicide cyproconazole, 

in or on peanut, hay at 6.0 parts per 

million (ppm), and peanut, nutmeat; 

peanut, meal; peanut, butter; and 

peanut, refined oil at 0.03 ppm. That 

document referenced a summary of the 

petition prepared by Syngenta Crop 

Protection, the registrant, which is 

available in the docket, http:// 

www.regulations.gov. There were no 

substantive comments received in 

response to the notice of filing. 

Based upon review of the data 

supporting the petition, EPA has 

modified the requested tolerance levels 

and crops for which tolerances were 

needed. The reasons for these changes 

are explained in Unit IV.C. 

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) of FFDCA requires EPA to 

give special consideration to exposure 

of infants and children to the pesticide 

chemical residue in establishing a 


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Federal Register / Vol. 78, No. 120 / Friday, June 21, 2013 / Rules and Regulations 37469 

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 FFDCA section 

408(b)(2)(D), and the factors specified in 

FFDCA section 408(b)(2)(D), 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 cyproconazole 

including exposure resulting from the 

tolerances established by this action. 

EPA’s assessment of exposures and risks 

associated with cyproconazole 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. 

The acute studies demonstrate that 

cyproconazole is moderately toxic by 

the oral, dermal, and inhalation routes. 

It is neither an eye nor dermal irritant. 

Cyproconazole did not cause dermal 

sensitization. Consistent with similar 

anti-fungal pesticide active ingredients 

in this class (e.g., tetraconazole), the 

critical toxicological effects for 

cyproconazole in mammals appear to be 

indicative of hepatotoxicity. These 

effects include elevated levels of the 

liver enzymes lactate dehydrogenase 

(LDH) and aspartate aminotransferase, 

increased liver weight (relative and 

absolute), vacuolization, fatty changes, 

hepatocytomegaly, hypertrophy, and 

single-cell necrosis. For both subchronic 

and chronic durations, hepatotoxicity 

was observed in rats, mice and dogs, 

and all of these species appeared to be 

equally sensitive to cyproconazole 

toxicity with regards to the range of the 

doses tested (∼0.5 to 130 milligrams/ 

kilogram/day (mg/kg/day)). Other 

notable effects seen in rat subchronic 

oral feeding studies included increased 

macrophages in the lung, increased 

white blood cell counts and globulins, 

decreased spleen weights, histocytosis 

of the spleen, and spleen 

micropathology. 

There are two dermal toxicity studies 

submitted for cyproconazole, both 

showing effects similar to the oral 

studies. In the 21-day study, dermal 

exposure to cyproconazole resulted in 

decreased body-weight gain and food 

consumption (males), increased 

aspartate aminotransferase (males), 

increased creatinine (females), and 

increased cholesterol in both sexes at 

the highest dose tested (1,250 mg/kg/ 

day). In the 28-day study, toxicity 

occurred at the mid-dose (100 mg/kg/ 

day). These effects included increased 

plasma globulin, protein and 

cholesterol, and hemosiderin deposition 

in the spleen in females (1,000 mg/kg/ 

day in males), hypertrophy of the 

thyroid follicular epithelium in both 

males and females, and increased 

incidences of centrilobular 

hepatocellular hypertrophy in males 

(1,000 mg/kg/day in females). 

The developmental studies indicate 

that cyproconazole causes 

developmental toxicity. There are two 

developmental toxicity studies in 

rabbits, which were more sensitive for 

developmental effects than the rat. In 

the older study using chinchilla rabbits, 

the pups showed increased 

susceptibility with toxicity occurring at 

the lowest dose tested (2 mg/kg/day, the 

developmental no observed adverse 

effect level (NOAEL) was not 

established). These effects included 

increased incidences of hydrocephalus 

internus (abnormal accumulation of 

cerebral spinal fluid in the ventricles of 

the brain). The maternal lowest 

observed adverse effect level (LOAEL) 

was 10 mg/kg/day. This developmental 

toxicity study was classified 

unacceptable and does not satisfy the 

guideline requirement for a 

developmental toxicity study (OPPTS 

Guideline 870.3700; OECD 414) in the 

rabbit because the concentrations of test 

material were not within the acceptable 

range (±15% of nominal concentration) 

for the mid- and high-dose suspensions 

immediately after preparation. In the 

most recent study using New Zealand 

white rabbits, cyproconazole produced 

increased incidences of malformed 

fetuses and litters with malformed 

fetuses (hydrocephalus and kidney 

agenesis) at doses lower than the doses 

that produced maternal toxicity (50 mg/ 

kg/day for dams and 10 mg/kg/day for 

fetuses). In rats, cyproconazole 

increased the incidences of 

supernumerary ribs at the same doses at 

which maternal adverse effects 

(decreased body-weight gain) were 

observed (12 mg/kg/day). There was no 

evidence of reproductive toxicity in the 

2-generation reproduction toxicity 

study. The parental toxicity in the 2- 

generation reproduction study was 

manifested as increased lipid storage 

and relative liver weights in males and 

increased relative liver weights in 

females (8.29 mg/kg/day). No offspring 

toxicity was observed at any of the 

doses tested. 

Although there was evidence of 

carcinogenicity found in a mouse study, 

EPA has determined that cyproconazole 

is ‘‘not likely to be carcinogenic to 

humans’’ at doses that do not cause a 

mitogenic response in the liver (Ref. 1). 

In contrast to rodent cells, there are 

some limited data to suggest that 

constitutive androstane receptor (CAR) 

activation does not stimulate cell 

proliferation or inhibit apoptosis in 

human cells. However, the literature 

does not yet support the conclusion that 

CAR activation is not biologically 

plausible in humans. This conclusion is 

based on the weight of evidence that 

supports a non-genotoxic mitogenic 

mode of action for cyproconazole. The 

activation of the CAR receptor, the 

required initiating event, leads to a 

cascade of key events resulting in liver 

tumor development in mice. The data 

did not support: (1) Peroxisome 

proliferation, (2) mutagenesis, or (3) 

cytotoxicity followed by sustained 

regenerative proliferation as alternative 

modes of action. The quantification of 

carcinogenic potential is not required. 

The current reference dose (RfD) of 0.01 

mg/kg/day is based on a 1-year dog 

study in which hepatotoxicity and organ 

weight changes were seen at 3.2 mg/kg/ 

day and no adverse effects were 

observed at 1 mg/kg/day (NOAEL). This 

RfD would be protective of any liver 

effects caused by cyproconazole in the 

mouse toxicity studies or mode of action 

studies at higher doses. 

There is no evidence of targeted 

neurotoxicity in the toxicity database. 

There were no central nervous system 

(CNS) malformations present in the 

developmental toxicity studies in rats 

and rabbits. In a 2-generation 

reproduction study in rats, there were 

no findings in pups that were suggestive 

of changes in neurological development. 

Additionally, there was no evidence of 

neurotoxicity in other studies. 

Finally, there is no evidence that 

cyproconazole is an immunotoxicant. 

Although there is no immunotoxicity 

study currently available for 

cyproconazole, the available data 

indicate that cyproconazole does not 

have immunotoxic effects. This is 

consistent with the fact that the target 

organ is the liver, which is similar to the 

other triazole fungicides, which do not 

have immunotoxic effects. 

Specific information on the studies 

received and the nature of the adverse 

effects caused by cyproconazole as well 

as the NOAEL and the LOAEL from the 

toxicity studies can be found at http:// 

www.regulations.gov in document 

‘‘Cyproconazole. Tolerance Petition for 


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Residues in/on Peanuts, Human-Health 

Risk Assessment’’ in docket ID number 

EPA–HQ–OPP–2012–0177. 

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 no adverse effects are 

observed (the NOAEL) and the lowest 

dose at which adverse effects of concern 

are identified (the LOAEL). Uncertainty/ 

safety factors are used in conjunction 

with the POD to calculate a safe 

exposure level—generally referred to as 

a population-adjusted 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 cyproconazole used for 

human risk assessment is shown in 

Table 1 of this unit. 

TABLE 1—SUMMARY OF TOXICOLOGICAL DOSES AND ENDPOINTS FOR CYPROCONAZOLE FOR USE IN HUMAN HEALTH RISK

ASSESSMENT

Exposure scenario POD Uncertainty/FQPA SF RfD, PAD, LOC for 

risk assessment Study and toxicological effects 

Acute Dietary (General population, including infants and 

children).

N/A ............................. N/A ............................. N/A ............................. A dose and endpoint attributable to a single 

dose were not identified in the database 

including the developmental toxicity studies. 

Acute Dietary (Females 13–49 years 

of age).

NOAEL = 2 mg/kg/day UFA = 10X .................

UFH = 10X 

FQPA SF = 1X 

aPAD = aRfD = 0.02 

mg/kg/day.

Prenatal Developmental toxicity Study—New 

Zealand white rabbits 

Developmental LOAEL = 10 mg/kg/day 

based on increased incidence of malformed fetuses and litters with malformed 

fetuses. 

Chronic Dietary (All 

populations).

NOAEL = 1.0 mg/kg/ 

day.

UFA = 10X .................

UFH = 10X 

FQPA SF = 1X 

cPAD = cRfD = 0.01 

mg/kg/day.

Chronic oral toxicity study—dog 

LOAEL = 3.2 mg/kg/day based on liver effects (P450 induction in females and 

histopathology, laminar eosinophilic 

intrahepatocytic bodies in males). 

Short (1–30 days)- 

and Intermediate 

(1–6 months)-Term 

Dermal.

NOAEL = 10 mg/kg/ 

day.

UFA = 10X .................

UFH = 10X 

FQPA SF = 1X 

Residential LOC for 

MOE = 100.

28-Day Dermal Study—rat 

LOAEL = 100 mg/kg/day, based on increased plasma globulin, protein and cholesterol, and hemosiderin deposition in the 

spleen in females, and hypertrophy of the 

thyroid follicular epithelium in both males 

and females. 

Cancer (oral, dermal, 

inhalation).

EPA has classified cyproconazole as ‘‘not likely to be carcinogenic to humans’’, according to EPA Proposed Guidelines 

for Carcinogen Risk Assessment (April 10, 1996). 

FQPA SF = Food Quality Protection Act Safety Factor. LOAEL = lowest-observed-adverse-effect-level. LOC = level of concern. mg/kg/day = 

milligrams/kilogram/day. MOE = margin of exposure. NOAEL = no-observed-adverse-effect-level. PAD = population adjusted dose (a = acute, c = 

chronic). RfD = reference dose. UF = uncertainty factor. UFA = extrapolation from animal to human (interspecies). UFH = potential variation in 

sensitivity among members of the human population (intraspecies). 

C. Exposure Assessment 

1. Dietary exposure from food and 

feed uses. In evaluating dietary 

exposure to cyproconazole, EPA 

considered exposure under the 

petitioned-for tolerances as well as all 

existing cyproconazole tolerances in 40 

CFR 180.485. EPA assessed dietary 

exposures from cyproconazole 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. In conducting the acute 

dietary exposure assessment, EPA used 

the food consumption data from the 

U.S. Department of Agriculture’s 

(USDA) National Health and Nutrition 

Examination Survey, What We Eat in 

America, (NHANES/WWEIA). This 

dietary survey was conducted from 2003 

to 2008. As to residue levels in food, an 

unrefined acute dietary exposure and 

risk analysis was performed assuming 

tolerance-level residues, 100% crop 

treated, DEEM (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’s 

NHANES/WWEIA. This dietary survey 

was conducted from 2003 to 2008. An 

unrefined chronic dietary exposure and 

risk analysis was performed assuming 

tolerance-level residues, 100% crop 

treated, DEEM (ver. 7.81) default 

processing factors. 

iii. Cancer. Based on the data 

summarized in Unit III.A., EPA has 

concluded that cyproconazole does not 

pose a cancer risk to humans. Therefore, 

a dietary exposure assessment for the 

purpose of assessing cancer risk is 

unnecessary. 

iv. Anticipated residue and percent 

crop treated (PCT) information. EPA did 

not use anticipated residue and/or PCT 

information in the dietary assessment 

for cyproconazole. Tolerance-level 


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residues and 100% crop treated was 

assumed for all food commodities. 

2. Dietary exposure from drinking 

water. The Agency used screening-level 

water exposure models in the dietary 

exposure analysis and risk assessment 

for cyproconazole in drinking water. 

These simulation models take into 

account data on the physical, chemical, 

and fate/transport characteristics of 

cyproconazole. 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 First Index Reservoir 

Screening Tool (FIRST) and Screening 

Concentration in Ground Water (SCI– 

GROW) models, the estimated drinking 

water concentrations (EDWCs) of 

cyproconazole for acute exposures are 

estimated to be 113 parts per billion 

(ppb) for surface water and 1.52 ppb for 

ground water. For chronic exposures for 

non-cancer assessments are estimated to 

be 43 ppb for surface water and 1.52 

ppb for ground water. 

Modeled estimates of drinking water 

concentrations were directly entered 

into the dietary exposure model. Since 

the EDWC estimates from surface water 

were higher than those from ground 

water, EDWC estimates in surface water 

were used in both acute and chronic 

dietary risk assessments. 

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). 

Cyproconazole is not registered for 

any specific use patterns that would 

result in residential handler exposure. 

Cyproconazole is proposed for use on 

golf course turf, which may result in 

post-application dermal exposure to 

golfers (both adults and children). No 

chemical-specific data were available to 

assess potential short-term dermal postapplication exposures to adult and 

youth golfers. Therefore, a series of 

assumptions and exposure factors 

served as the basis for completing the 

residential post-application risk 

assessment. Each assumption and factor 

is detailed in the 2012 Residential SOPs 

(http://www.epa.gov/pesticides/science/ 

residential-exposure-sop.html). Postapplication oral and inhalation 

exposures, as well as residential handler 

exposures, are not expected based on 

the current use patterns for 

cyproconazole. 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.’’ 

Cyproconazole is a member of the 

triazole-containing class of pesticides. 

Although conazoles act similarly in 

plants 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 (Ref. 2). 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 

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

cumulative. 

Cyproconazole 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 

cyproconazole, 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 10X 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 complete risk assessment 

is found in the propiconazole 

reregistration docket at http:// 

www.regulations.gov, docket 

identification (ID) number EPA–HQ– 

OPP–2005–0497. 

An updated dietary exposure and risk 

analysis for the common triazole 

metabolites 1,2,4-triazole (T), 

triazolylalanine (TA), triazolylacetic 

acid (TAA), and triazolylpyruvic acid 

(TP) was conducted and completed in 

August 2012, in association with a 

registration request for the triazole 

fungicide, propiconazole. Residue data 

demonstrated that there was no increase 

in exposure to the common triazole 

metabolites with the proposed use. The 

tolerances for cyproconazole in/on 

peanuts covered by this action are not 

expected to change the risk of exposure 

to the triazoles determined in that risk 

analysis. The document, titled 

‘‘Common Triazole Metabolites: 

Updated Aggregate Human Health Risk 

Assessment to Address the Amended 

Propiconazole Section 3 Registration to 

Add Use on Sugarcane’’ may be found 

in docket ID number EPA–HQ–OPP– 

2012–0427. 

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 (10X) 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 10X, 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. 

There are no residual uncertainties with 

regard to prenatal and postnatal toxicity, 

and the database is complete for 

purposes of assessing prenatal and 

postnatal toxicity. There is evidence 

that cyproconazole is a developmental 


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37472 Federal Register / Vol. 78, No. 120 / Friday, June 21, 2013 / Rules and Regulations 

toxicant; however, the LOC is low since: 

(1) The effects in fetuses are wellcharacterized with a clear NOAEL and 

(2) the developmental toxicity study 

where increased susceptibility was 

observed is being used for the acute 

dietary endpoint (females 13–49 years), 

which will be protective of effects in 

infants and children. There is no 

evidence of reproductive toxicity or 

neurotoxicity in the cyproconazole 

database. 

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 1X. That decision is 

based on the following findings: 

i. The toxicity database for 

cyproconazole is complete, except for 

an immunotoxicity study. As noted in 

Unit III.A., the concern for the lack of 

this study is low because there is no 

evidence that cyproconazole causes 

immunotoxic effects. EPA does not 

believe that an immunotoxicity study 

will result in a lower point of departure 

(POD) than that which is currently in 

use for overall risk assessment. As such, 

a database uncertainty factor is not 

necessary to account for the lack of an 

immunotoxicity study. 

ii. There is no indication that 

cyproconazole is a neurotoxic chemical 

and there is no need for a 

developmental neurotoxicity study or 

additional UFs to account for 

neurotoxicity. 

iii. While there is evidence that 

exposure to cyproconazole results in 

increased susceptibility in in utero 

rabbits, EPA does not believe that the 

FQPA safety factor of 10X is necessary 

to protect infants and children for the 

reasons stated in Unit III.D.2. above. 

iv. There are no residual uncertainties 

identified in the exposure databases. 

EPA made conservative (protective) 

assumptions in the ground water and 

surface water modeling used to assess 

exposure to cyproconazole in drinking 

water. These assessments will not 

underestimate the exposure and risks 

posed by cyproconazole. 

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 acute PAD (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 

cyproconazole will occupy 32% of the 

aPAD for females 13–49 years old. The 

acute dietary exposure and risk analysis 

was conducted only for females 13–49 

years old since an endpoint of concern 

attributable to a single dose for the 

general population was not identified. 

2. Chronic risk. Using the exposure 

assumptions described in this unit for 

chronic exposure, EPA has concluded 

that chronic exposure to cyproconazole 

from food and water will utilize 28% of 

the cPAD for infants (<1 years old), the 

population group receiving the greatest 

exposure. There are no residential uses 

for cyproconazole. 

3. Short-term risk. Short-term 

aggregate exposure is calculated by 

aggregating short-term residential 

exposure plus chronic exposure to food 

and water (considered to be a 

background exposure level). A shortterm adverse effect was identified; 

however, cyproconazole is not currently 

registered for any use patterns that 

would result in short-term residential 

exposure. In consideration of a pending 

turf use for cyproconazole, a short-term 

aggregate assessment was completed. 

The pending golf course use is the only 

use that may result in residential 

exposure. The golfer exposure (dermal) 

represents the highest residential 

exposure of all potential adult exposure 

scenarios. Therefore, the short-term 

assessment is protective of all potential 

exposures resulting from the pending 

golf course use. For the short-term 

aggregate assessment, the short-term 

oral NOAEL of 1.5 mg/kg/day (from the 

90-day oral rat study) is compared to the 

total (dietary + residential) exposure to 

calculate risk. Since the aggregate MOEs 

are greater than 100, the calculated risks 

do not exceed the Agency’s LOCs. 

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). 

There are no residential scenarios that 

result in intermediate-term exposure; 

therefore, an intermediate-term 

aggregate exposure and risk assessment 

is not required. 

5. Aggregate cancer risk for U.S. 

population. Although there was 

evidence of carcinogenicity found in a 

mouse study, EPA has determined that 

cyproconazole is ‘‘not likely to be 

carcinogenic to humans’’ at doses that 

do not cause a mitogenic response in the 

liver (Ref. 1). As a result, an aggregate 

cancer exposure and risk assessment is 

not required, as cyproconazole is not 

expected to pose a cancer risk to 

humans. 

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 

cyproconazole residues. 

IV. Other Considerations 

A. Analytical Enforcement Methodology 

Adequate enforcement methodology 

(gas chromatograph/nitrogenphosphorus detection) is available to 

enforce the tolerance expression. The 

method 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 

United Nations 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. The Codex has not 

established a MRL for cyproconazole. 

C. Revisions to Petitioned-for Tolerances 

The Agency is correcting the 

commodity terminology for peanut by 

establishing a tolerance for peanut, 

rather than peanut, nutmeat. In 

addition, the Agency has modified the 

levels for which tolerances are being 

established for peanut (0.03 to 0.01 

ppm). Based on an analysis of the 

residue data using the OECD tolerance 

calculation procedures, the tolerance for 

peanut is based on the limit of 

quantitation (0.01 ppm). Following 

exaggerated-rate applications of 

cyproconazole, average residues of 


TKELLEY on DSK3SPTVN1PROD with RULES
Federal Register / Vol. 78, No. 120 / Friday, June 21, 2013 / Rules and Regulations 37473 

cyproconazole were below the limit of 

quantitation in/on peanut, meal, refined 

oil, and butter; therefore, processing 

factors could not be calculated. 

Accordingly, separate tolerances for 

residues of cyproconazole are not 

required for peanut, meal, refined oil, 

and peanut butter. 

Also, EPA has revised the tolerance 

expression for cyproconazole 40 CFR 

180.485 to clarify: 

1. That as provided in FFDCA section 

408(a)(3), the tolerance covers 

metabolites and degradates of 

cyproconazole. 

2. That compliance with the specified 

tolerance levels is to be determined by 

measuring only the specific compounds 

mentioned in the tolerance expression. 

V. Conclusion 

Therefore, tolerances are established 

for residues of cyproconazole, in or on 

peanut and peanut, hay at 0.01 and 6.0 

ppm, respectively. 

VI. References 

The following is a listing of the 

documents that are specifically 

referenced in this rule. 

1. J. Kidwell, et al., December 4, 2007. 

Cyproconazole: Fourth Report of the 

Cancer Assessment Review Committee 

PC Code: 128993. 

2. Environmental Protection Agency. January 

14, 2002. Guidance on Cumulative Risk 

Assessment of Pesticide Chemicals That 

Have a Common Mechanism of Toxicity. 

VII. Statutory and Executive Order 

Reviews 

This final rule establishes tolerances 

under FFDCA section 408(d) 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 FFDCA section 408(d), 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 FFDCA section 408(n)(4). 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) (2 U.S.C. 1501 et seq.). 

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

VIII. Congressional Review Act 

Pursuant to the Congressional Review 

Act (5 U.S.C. 801 et seq.), 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 the rule in the Federal 

Register. This action 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: June 11, 2013. 

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 180.485 is amended as 

follows: 

■ a. Revise paragraph (a)(1) introductory 

text. 

■ b. Add alphabetically the entries 

‘‘peanut’’ and ‘‘peanut, hay’’ to the table 

in paragraph (a)(1). 

■ c. Revise paragraph (a)(2) introductory 

text. 

■ d. Revise paragraph (a)(3) 

introductory text. 

The amendments read as follows: 

§ 180.485 Cyproconazole; tolerances for 

residues. 

(a) * * * (1) Tolerances are 

established for residues of the free and 

conjugated forms of the fungicide 

cyproconazole, including its metabolites 

and degradates, in or on the 

commodities in the table below. 

Compliance with the proposed tolerance 

levels specified below is to be 

determined by measuring only 

cyproconazole (a-(4-chlorophenyl)-a-(1- 

cyclopropylethyl)-1H-1,2,4-triazole-1- 

ethanol) in or on the following 

commodities: 

Commodity Parts per million 

* * * * * 

Peanut ................................ 0 .01 

Peanut, hay ........................ 6 .0 

* * * * * 

* * * * * 

(2) A tolerance is established for the 

combined residues of the free and 

conjugated forms of the fungicide 

cyproconazole, including its metabolites 

and degradates, in or on the commodity 

in the table below. Compliance with the 

tolerance level specified below is to be 

determined by measuring only the sum 

of cyproconazole (a-(4-chlorophenyl)-a- 

(1-cyclopropylethyl)-1H-1,2,4-triazole-1- 

ethanol) and its metabolite d-(4- 

chlorophenyl)-b,d-dihydroxy-g-methyl1H-1,2,4-triazole-1-hexenoic acid, 

calculated as the stoichiometric 

equivalent of cyproconazole, in or on 

the following commodity: 

* * * * * 


TKELLEY on DSK3SPTVN1PROD with RULES
37474 Federal Register / Vol. 78, No. 120 / Friday, June 21, 2013 / Rules and Regulations 

(3) Tolerances are established for the 

combined residues of the free and 

conjugated forms of the fungicide 

cyproconazole, including its metabolites 

and degradates, in or on the 

commodities in the table below. 

Compliance with the tolerance level 

specified below is to be determined by 

measuring only the sum of 

cyproconazole (a-(4-chlorophenyl)-a-(1- 

cyclopropylethyl)-1H-1,2,4-triazole-1- 

ethanol) and its metabolite 2-(4- 

chlorophenyl)-3-cyclopropyl-1- 

[1,2,4]triazol-1-yl-butane-2,3-diol, 

calculated as the stoichiometric 

equivalent of cyproconazole, in or on 

the following commodities: 

* * * * * 

[FR Doc. 2013–14914 Filed 6–20–13; 8:45 am] 

BILLING CODE 6560–50–P 

FEDERAL COMMUNICATIONS 

COMMISSION 

47 CFR Part 13 

[WT Docket No. 10–177; FCC 13–4] 

Commercial Radio Operators 

AGENCY: Federal Communications 

Commission. 

ACTION: Final rule; announcement of 

effective date. 

SUMMARY: In this document, the Federal 

Communications Commission (FCC) 

announces that the Office of 

Management and Budget (OMB) has 

approved, for a period of three years, the 

information collection associated with 

commercial radio licenses, as well as for 

Commercial Operator License 

Examination Managers (COLEM(s)) that 

administer commercial radio operator 

licenses across the United States. 

DATES: The amendments to 47 CFR 13.9, 

13.13(c), 13.17(b), 13.211(e) and 13.217 

published at 78 FR 23150, April 18, 

2013 became effective June 7, 2013. 

FOR FURTHER INFORMATION CONTACT: 

Stana Kimball, Mobility Division, 

Wireless Telecommunications Bureau, 

(202) 418–1306 or via the Internet at: 

stanislava.kimball@fcc.gov. 

SUPPLEMENTARY INFORMATION: This 

document announces that on June 7, 

2013 OMB approved, for a period of 

three years, the information collection 

requirements contained in the 

Commission’s Report and Order, FCC 

13–4, published at 78 FR 23150, April 

18, 2013. The OMB Control Number is 

3060–0537. The Commission publishes 

this notice as an announcement of such 

approval. 

Synopsis 

As required by the Paperwork 

Reduction Act of 1995 (44 U.S.C. 3507), 

the FCC is notifying the public that on 

June 7, 2013 it received OMB approval 

for the information collection 

requirements contained in the 

modifications to the Commission’s rules 

found in 47 CFR 13.9, 13.13(c), 13.17(b), 

13.211(e) and 13.217. 

Under 5 CFR 13.20, an agency may 

not conduct or sponsor a collection of 

information unless it displays a current, 

valid OMB Control Number. 

No person shall be subject to any 

penalty for failing to comply with a 

collection of information subject to the 

Paperwork Reduction Act that does not 

display a current, valid OMB Control 

Number. The OMB Control Number is 

3060–0537. 

The foregoing notice is required by 

the Paperwork Reduction Act of 1995, 

Public Law 104–13, October 1, 1995, 

and 44 U.S.C. 3507. 

The total annual reporting burdens 

and costs for the respondents are as 

follows: 

OMB Control Number: 3060–0537. 

OMB Approval Date: June 7, 2013. 

OMB Expiration Date: June 30, 2016. 

Title: Sections 13.9, 13.13(c), 13.17(b), 

13.211(e) and 13.217, Commercial 

Operator License Examination Managers 

(COLEM) Records. 

Form Number: N/A. 

Type of Review: Revision of a 

currently approved collection. 

Respondents: Business or other forprofit entities. 

Number of Respondents and 

Responses: 9 respondents; 9 responses. 

Estimated Time per Response: 0.44 

hours up to 30 hours. 

Frequency of Response: On occasion 

and semi-annual reporting requirements 

and recordkeeping requirements. 

Obligation to Respond: Required to 

obtain or retain benefits. Statutory 

authority for this information collection 

is contained in 47 U.S.C. 154 and 303 

of the Communications Act of 1934, as 

amended. 

Total Annual Burden: 14,796 hours. 

Total Annual Cost: N/A. 

Privacy Impact Assessment: N/A. 

Nature and Extent of Confidentiality: 

There is no need for confidentiality. 

Needs and Uses: Each COLEM 

recovering fees from examinees must 

maintain records of expenses and 

revenues, frequency of examinations 

administered, and examination pass 

rates. Records must cover from January 

to December 31 of the preceding year 

and must be submitted as directed by 

the FCC. Each COLEM must retain 

records for three years and the records 

must be made available to the FCC upon 

request. 

The records are journal entries 

showing revenues collected and 

expenses incurred. The records may be 

inspected by FCC field investigators. 

The records will provide a vehicle for 

the FCC to cancel the designation of a 

person or organization as an 

examination manager. If the information 

were not collected, it is conceivable that 

fraud and abuse could occur in the 

commercial operator examination 

program. 

Federal Communications Commission. 

Marlene H. Dortch, 

Secretary. 

[FR Doc. 2013–14764 Filed 6–20–13; 8:45 am] 

BILLING CODE 6712–01–P 

FEDERAL COMMUNICATIONS 

COMMISSION 

47 CFR Part 73 

[MB Docket No. 12–352; RM–11686; DA 13– 

315] 

Radio Broadcasting Services; Dove 

Creek, Colorado 

AGENCY: Federal Communications 

Commission. 

ACTION: Final rule. 

SUMMARY: The Audio Division, at the 

request of Cochise Media Licenses, LLC, 

allots FM Channel 229C3 as a first local 

transmission service at Dove Creek, 

Colorado. Channel 229C3 can be 

allotted at Dove Creek, consistent with 

the minimum distance separation 

requirements of the Commission’s rules, 

at coordinates 37–48–05 NL and 108– 

59–33 WL. See SUPPLEMENTARY

INFORMATION infra. 

DATES: Effective July 22, 2013. 

FOR FURTHER INFORMATION CONTACT: 

Deborah Dupont, Media Bureau, (202) 

418–2180. 

SUPPLEMENTARY INFORMATION: This is a 

synopsis of the Commission’s Report 

and Order, MB Docket No. 12–352, 

adopted February 28, 2013, and released 

March 1, 2013. The full text of this 

Commission decision is available for 

inspection and copying during normal 

business hours in the FCC Information 

Center, Portals II, 445 12th Street SW., 

Room CY–A257, Washington, DC 20554. 

The complete text of this decision also 

may be purchased from the 

Commission’s duplicating contractor, 

Best Copy and Printing, Inc., 445 12th 

Street SW., Room CY–B402, 

Washington, DC 20554, (800) 378–3160, 

or via the company’s Web site, 

www.bcpiweb.com. This document does 


TKELLEY on DSK3SPTVN1PROD with RULES