11760 Federal Register / Vol. 78, No. 34 / Wednesday, February 20, 2013 / Rules and Regulations 

EPA-APPROVED MISSOURI REGULATIONS—Continued 

Missouri citation Title State effective date EPA approval date Explanation 

*******

10–6.400 .......................................... Restriction of Emission of Particulate Matter from Industrial Processes.02/28/11 02/20/13 [insert FEDERAL REGISTER

page number where the document begins].

* * * * * * * 

* * * * * 

[FR Doc. 2013–03769 Filed 2–19–13; 8:45 am] 

BILLING CODE 6560–50–P 

ENVIRONMENTAL PROTECTION 

AGENCY 

40 CFR Part 180 

[EPA–HQ–OPP–2010–0065; FRL–9378–1] 

3-decen-2-one; Exemption from the 

Requirement of a Tolerance 

AGENCY: Environmental Protection 

Agency (EPA). 

ACTION: Final rule. 

SUMMARY: This regulation establishes an 

exemption from the requirement of a 

tolerance for residues of the biochemical 

pesticide, 3-decen-2-one, in or on 

potatoes when applied as a postharvest 

potato sprout inhibitor and used in 

accordance with label directions and 

good agricultural practices. On behalf of 

AMVAC Chemical Corporation 

(AMVAC), Technology Sciences Group, 

Inc. (TSG) submitted a petition to EPA 

under the Federal Food, Drug, and 

Cosmetic Act (FFDCA), requesting an 

exemption from the requirement of a 

tolerance. This regulation eliminates the 

need to establish a maximum 

permissible level for residues of 3- 

decen-2-one under the FFDCA. 

DATES: This regulation is effective 

February 20, 2013. Objections and 

requests for hearings must be received 

on or before April 22, 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–2010–0065, 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: 

Colin G. Walsh, Biopesticides and 

Pollution Prevention Division (7511P), 

Office of Pesticide Programs, 

Environmental Protection Agency, 1200 

Pennsylvania Ave. NW., Washington, 

DC 20460–0001; telephone number: 

(703) 308–0298; email address: 

walsh.colin@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 40 CFR part 180 

through the Government Printing 

Office’s e-CFR 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(g), 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–2010–0065 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 April 22, 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– 

2010–0065, 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. 


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II. Background and Statutory Findings 

In the Federal Register of March 10, 

2010 (75 FR 11171) (FRL–8810–8), EPA 

issued a document pursuant to FFDCA 

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

announcing the filing of a pesticide 

tolerance petition (PP 9F7670) by TSG, 

1150 18th Street NW., Suite 1000, 

Washington, DC 20036, on behalf of 

AMVAC, 4695 MacArthur Court, Suite 

1250, Newport Beach, CA 90660. The 

petition requested that 40 CFR part 180 

be amended by establishing an 

exemption from the requirement of a 

tolerance for residues of 3-decen-2-one. 

This notice referenced a summary of the 

petition prepared by the petitioner, TSG 

(on behalf of AMVAC), which is 

available in the docket via http:// 

www.regulations.gov. Comments were 

received on the notice of filing. EPA’s 

response to these comments is 

discussed in Unit VII.C. 

During the initial review of the 

petition, EPA determined that the data 

and/or information submitted was 

insufficient to support the use of the 

active ingredient, 3-decen-2-one, in or 

on all food commodities. The petitioner 

submitted additional data and filed a 

revised petition (PP 9F7670), proposing 

to establish an exemption from the 

requirement of a tolerance for residues 

of 3-decen-2-one in or on stored 

potatoes only. A Notice of Filing, 

allowing for a 30-day comment period, 

was published in the Federal Register of 

March 14, 2012 (77 FR 15012) (FRL– 

9335–9). No comments were received 

following this publication. 

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

allows EPA to establish an exemption 

from the requirement for a tolerance (the 

legal limit for a pesticide chemical 

residue in or on a food) only if EPA 

determines that the exemption is ‘‘safe.’’ 

Section 408(c)(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. Pursuant to 

FFDCA section 408(c)(2)(B), in 

establishing or maintaining in effect an 

exemption from the requirement of a 

tolerance, EPA must take into account 

the factors set forth in FFDCA section 

408(b)(2)(C), which require EPA to give 

special consideration to exposure of 

infants and children to the pesticide 

chemical residue in establishing a 

tolerance exemption 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. * * *’’ Additionally, 

FFDCA section 408(b)(2)(D) requires 

that EPA consider ‘‘available 

information concerning the cumulative 

effects of [a particular pesticide’s] * * * 

residues and other substances that have 

a common mechanism of toxicity.’’ 

EPA performs a number of analyses to 

determine the risks from aggregate 

exposure to pesticide residues. First, 

EPA determines the toxicity of 

pesticides. Second, EPA examines 

exposure to the pesticide through food, 

drinking water, and through other 

exposures that occur as a result of 

pesticide use in residential settings. 

III. Toxicological Profile 

Consistent with FFDCA section 

408(b)(2)(D), EPA reviewed the available 

scientific data and other relevant 

information in support of this action 

and considered its validity, 

completeness and reliability, and the 

relationship of this information to 

human risk. EPA also considered 

available information concerning the 

variability of the sensitivities of major 

identifiable subgroups of consumers, 

including infants and children. 

A. Overview 

3-decen-2-one is a naturally occurring 

biochemical substance, as defined in 40 

CFR 158.2000(a)(1), with a history of 

unremarkable human exposure. 3- 

decen-2-one functions as a plant growth 

regulator, affecting plant growth by 

increasing tuber respiration. Data on file 

indicate that 3-decen-2-one interferes 

with membrane integrity, which results 

in increased oxidative stress, 

desiccation, and rapid necrosis of the 

meristems and surrounding sprout 

tissues. Thus, 3-decen-2-one inhibits 

sprouting with no observed effects on 

the potato, potato sweetening, or 

processing quality. Based on this 

information, EPA considers the mode of 

action to be non-toxic (Ref. 1). 

3-decen-2-one is approved by the U.S. 

Food and Drug Administration (FDA) as 

a synthetic flavoring agent and adjuvant 

that may be directly added to food (21 

CFR 172.515). A report by an 

independent panel of experts retained 

by the Flavor and Extract 

Manufacturer’s Association (FEMA) 

states 3-decen-2-one is considered safe 

for its intended use when added at an 

average maximum level of 19 ppm in 

baked goods, 7.8 ppm in soft candy, 5.8 

ppm in frozen dairy products, 4.8 ppm 

in gelatins and puddings, 4.3 ppm in 

non-alcoholic beverages, and 4.0 ppm in 

alcoholic beverages (Oser & Ford, 1978) 

(Ref. 2). 

3-decen-2-one has been well 

characterized and studied with respect 

to its metabolism and, more 

importantly, its natural occurrence in 

many foods that are common in the 

human diet including yogurt, skipjack 

tuna, edible porcini mushrooms and 

Iberian ham (Ref. 2). Additionally, the 

Joint FAO/WHO Expert Committee on 

Food Additives (JECFA) has reported 

that 3-decen-2-one, a structural class II 

flavoring agent, is one in a group of 

compounds that have been identified in 

fruits, vegetables, spices, cocoa, coffee 

and tea. JECFA concluded that there are 

no safety concerns at current intake 

levels when 3-decen-2-one is used as a 

flavoring agent (Ref. 2). 

As stated previously in this unit, 3- 

decen-2-one is a substance that exhibits 

a non-toxic mode of action. In humans, 

this substance readily metabolizes into 

innocuous compounds (Ref. 1). Based 

on information submitted in support of 

this petition (summarized in Unit III.B.) 

and the comprehensive risk assessment 

conducted by the Agency, EPA 

concludes that there is a reasonable 

certainty of no harm from aggregate 

exposures to 3-decen-2-one, including 

the consumption of potatoes treated 

with this active ingredient in 

accordance with label directions and 

good agricultural practices. EPA has 

made this determination for the 

following reasons: 

1. Available toxicology data and 

information indicate that the active 

ingredient is of low acute toxicity (with 

the exception that it is an eye and skin 

irritant) and is not a developmental 

toxicant, a mutagen, or toxic via repeat 

oral exposure; 

2. Available information from the 

scientific literature indicate humans are 

already exposed to 3-decen-2-one in the 

diet from foods that naturally contain 

the chemical and from foods to which 

the chemical has been added as a food 

additive at levels higher than what will 

occur from pesticide use; 

3. Metabolism data and information 

on the chemical indicate that it is 

metabolized into innocuous substances 

in humans that present no toxicological 

or dietary concern; and 

4. Deterministic exposure analyses 

suggest that dietary exposure to the 

chemical as a pesticide is likely to be 

less than dietary exposure to the 

chemical as a food additive, thus as a 

natural constituent in foods, the 

pesticidal use of 3-decen-2-one is not 

likely to result in a significant increase 

in overall dietary exposure (Ref. 2). 


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B. Toxicity 

The following is a summary of EPA’s 

review of the toxicity profile of this 

biochemical. 

1. Acute toxicity (OCSPP Guideline 

Nos. 870.1100, 870.1200, 870.1300, 

870.2400, 870.2500, and 870.2600; 

Master Record Identification (MRID) 

Nos. 47942609, 47942610, 47942611, 

47942612, 47942613, and 47942614). 

The petitioner submitted acute toxicity 

studies conducted on the technical 

grade material to EPA. Results of the 

acute toxicity testing indicate that 3- 

decen-2-one is of low acute toxicity 

with the exception that the substance is 

an eye and skin irritant. Acute oral 

toxicity (rat): LD50 > 5,000mg/kg; Acute 

dermal toxicity (rat): LD50 > 5,000mg/kg; 

Acute inhalation toxicity (rat): LC50 = 

0.52–2.04 mg/L (male) and LC50 > 2.04 

mg/L (female); Primary eye irritation 

(rabbit): moderately irritating; Primary 

dermal irritation (rabbit): Severely 

irritating; Dermal sensitization (guinea 

pig): not a dermal sensitizer (Ref. 3). 

2. 90-day oral toxicity (OCSPP 

Guideline No. 870.3100; MRID Nos. 

47942617 and 48422301). A subchronic 

90-day oral toxicity study on the 

technical grade material was not 

conducted. In lieu of the study, EPA 

used a weight-of-the-evidence (WOE) 

approach to estimate the likelihood of 

potential of toxicity from repeat oral 

exposure to this substance (Ref. 2). EPA 

considered the following evidence: 

i. Lack of toxicological endpoints; 

ii. Metabolic pathways; 

iii. Lack of incidents associated with 

naturally occurring levels of 3-decen-2- 

one in foods; and 

iv. FDA’s approval of this biochemical 

as a direct food additive. 

First, using an expert system 

computer program (DEREK Nexus), EPA 

identified two potential toxicological 

endpoints for 3-decen-2-one (potential 

dermal sensitization and in vitro 

chromosome damage); however, followup studies did not support these as 

toxicological endpoints. Second, the 

metabolic pathways of 3-decen-2-one 

have been characterized and 

demonstrate that the biochemical is 

metabolized into innocuous compounds 

that are either excreted or further 

metabolized in the fatty acid pathway or 

citric acid cycle. Third, 3-decen-2-one 

occurs naturally in some foods and has 

been used as a food additive without 

specific reports of adverse effects. 

Finally, as noted in this unit, FDA has 

approved the use of 3-decen-2-one as a 

synthetic flavoring agent and adjuvant 

that may be directly added to food. 

Based on this evidence, EPA concludes 

that 3-decen-2-one has relatively low 

toxicity. 

3. Prenatal developmental toxicity 

(OCSPP Guideline No. 870.3700; MRID 

No. 48970303). An acceptable prenatal 

developmental toxicity study was 

submitted. In the study, Crl:CD SpragueDawley rats were administered doses of 

AMV–1018 (99.81% purity 3-decen-2- 

one) by gavage at 0, 100, 300 or 1,000 

mg/kg/day from day 6 to day 19 of 

gestation. Each treatment group 

consisted of 24 female rats: 

i. The control group which received 

corn oil and 

ii. The test substance vehicle group. 

No maternal deaths or clinical signs 

related to treatment were observed in 

the study. Salivation was observed in all 

animals in the intermediate- and highdose groups during the treatment 

period. Chin rubbing, which is 

associated with salivation, was observed 

in some animals in the high-dose group. 

These observations were considered to 

be attributable to the palatability of the 

test substance and not toxicologically 

significant. Bodyweight gain in the lowand intermediate-dose groups was not 

affected by treatment. When compared 

to the control group, overall mean 

bodyweight gain in the high-dose group 

was slightly low during gestation, which 

was associated with slightly lower food 

consumption in the high-dose group. 

The bodyweight gain effect is 

considered to be attributable to the 

palatability of the test substance and not 

toxicologically significant. Food 

consumption in the low- and 

intermediate-dose groups was 

unaffected by treatment. Gravid uterine 

weights were not affected by treatment 

in any group. There were no maternal 

treatment-related macroscopic effects. 

All females in each test group were 

pregnant. Mean corpora lutea, 

implantations, early, late and total 

resorption counts, live young, sex ratio, 

pre- and post-implantation loss, litter 

weight, placental weight, male and 

female fetal weight and overall fetal 

weight were all considered to be 

unaffected by treatment at all doses. In 

all dose groups, no relationship to 

treatment was observed in the incidence 

of major and minor fetal abnormalities 

and skeletal variants. There was a slight 

increase in the percentage of incidences 

of fetuses with 13/14 and 14/14 ribs in 

all dose groups when compared to the 

control group, but the incidences were 

similar to historical control data, and in 

the absence of other related findings in 

the study, the observations were not 

considered to be treatment related. 

Based on the lack of systemic maternal 

and fetal toxicity, the no-observedadverse-effect-level (NOAEL) for 

maternal and fetal (developmental) 

toxicity is 1,000 mg/kg/day (Ref. 2). 

4. Mutagenicity (OCSPP Guideline 

Nos. 870.5100, 870.5300, and 870.5395; 

MRID Nos. 47942616, 47942615, and 

48412402). Three mutagenicity studies 

were submitted. In a reverse mutation 

assay, AMV–1018, containing 98% of 

the active ingredient 3-decen-2-one, was 

investigated for its potential to induce 

gene mutations via a plate incorporation 

test and a pre-incubation test. Each 

experiment was conducted with five 

tester strains of Salmonella 

typhimurium, six different test 

substance concentrations (0.0316, 0.100, 

0.316, 1.0, 2.5 and 5.0 mL/plate, and 

control scenario), and with and without 

metabolic activation. According to the 

results of this study, no biologically 

relevant increases in revertant colony 

numbers of any of the five tester strains 

were observed following treatment with 

AMV–1018 at any concentration level, 

neither in the presence or absence of 

metabolic activation, in either 

experiment. In the pre-incubation 

experiments, cytotoxicity was noted in 

all five tester strains at a dose 

concentration of 5.0 mL/plate without 

metabolic activation and in tester strain 

TA 102 at a dose concentration of 5.0 

mL/plate with metabolic activation. The 

reference mutagens employed in the 

control scenarios induced a distinct 

increase in revertant colonies, 

indicating the validity of the 

experiments. Therefore, the test 

substance is considered to be nonmutagenic in this bacterial reverse 

mutation assay (Ref. 3). 

In a mammalian cell gene mutation 

assay, mouse lymphoma cells cultured 

in vitro were exposed to AMV–1018 (3- 

decen-2-one; 98.57% active ingredient) 

in dimethyl sulfoxide (DMSO) at the 

various concentrations for 4 and 24 

hours with and without metabolic 

activation. The S9 fraction (for 

metabolic activation) was derived from 

the livers of male Wistar rats induced 

with phenobarbital (80 mg/kg bw) and 

b-Naphthoflavone (100 mg/kg bw). The 

solvent DMSO served as a negative 

control in the presence and absence of 

S9. Benzo(a)pyrene (BP) served as a 

positive control in the presence of S9. 

Ethylmethanesulfonate (EMS) and 

methylmethanesulfonate (MMS) served 

as positive controls in the absence of S9. 

Selection of test substance 

concentrations were based on a preexperiment for cytotoxicity. No 

precipitation of the test substance was 

noted in the experiments. Growth 

inhibition was noted in all experiments 

(+/¥ S9), with marked cytotoxicity seen 

in several cases (one incident less than 

10%, several less than 20%). The pH 

values for the highest concentrations 


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tested were within the physiological 

range. The osmolality for the solvent 

controls as well as for the highest test 

concentrations was found to be 465 

mosmol/kg. Thus, the osmolality was 

above the physiological range. Test 

substance was positive for mutagenicity 

in the 24 hour exposure without 

metabolic activation and equivocal 

results with metabolic activation. The 

mouse lymphoma results are considered 

equivocal because it is not clear whether 

the positive results would translate into 

an in vivo system based on the increased 

osmotic pressure and marked 

cytotoxicity noted during the 

experiment (Ref. 3). 

A Tier II in vivo mammalian 

erythrocyte micronucleus test guideline 

study was submitted due to the 

equivocal results found in the mouse 

lymphoma assay. The test substance for 

the study was AMV–1018, containing 

98.0% 3-decen-2-one. The test 

substance was prepared with cottonseed 

oil and the volume administered 

intraperitoneal to the 5 male and 5 

female mice was 10 mL/kg bw. A range 

finding study was performed prior to 

the experiment to determine the 

maximum tolerable dose (MTD). The 

MTD was determined to be 50%/kg bw, 

which is equivalent to an application of 

10 mL/kg bw of 5% v/v test item 

solution. The three dose levels used in 

the experiment were 1 MTD, 0.5 MTD, 

and 0.2 MTD, which is equivalent to 

50%/kg bw, 25%/kg bw, and 10%/kg 

bw, respectively. The animals treated 

with a dose of 0.2 MTD showed no signs 

of systemic toxicity after treatment, 

whereas the animals at 1 MTD and 0.5 

MTD showed signs of toxicity including 

reduction of spontaneous activity, prone 

position, clonic convulsion, ataxia, 

constricted abdomen, piloerection, half 

eyelid closure, diarrhea, cramps, and 

loss of weight. Peripheral blood samples 

were taken at 44 and 68 hours after a 

single application of the test item 

solution for micronuclei analysis. All 

mean values of micronuclei were within 

range or decreased compared to the 

corresponding negative control in all 

dose groups. The positive control used 

cyclophosphamide (40 mg/kg bw), 

which showed significant increase in 

micronucleus frequency and was used 

to validate the assay. A nonparametric 

Mann-Whitney Test was performed and 

showed no statistically significant 

increase (p<0.05) of micronuclei cells in 

any dose group. The test material, 

AMV–1018 (98% 3-decen-2-one), is 

considered non-mutagenic with respect 

to clastogenicity and aneugenicity based 

on the test item material showing no 

signs of induction of structural or 

numerical chromosomal damage in the 

immature erythrocytes of the mice (Ref. 

1). 

IV. Aggregate Exposures 

In examining aggregate exposure, 

FFDCA section 408 directs EPA to 

consider available information 

concerning exposures from the pesticide 

residue in food and all other nonoccupational exposures, including 

drinking water from ground water or 

surface water and exposure through 

pesticide use in gardens, lawns, or 

buildings (residential and other indoor 

uses). 

A. Dietary Exposure 

In addition to the natural presence 

and the deliberate addition of 3-decen2-one in other foods, people will be 

exposed 3-decen-2-one through the 

consumption of treated potatoes. A 

qualitative risk assessment was 

conducted for the chemical to assess 

potential risks (if any) from dietary 

exposure. 

1. Food. Dietary exposure to 3-decen2-one is already occurring, given that 

this substance is a component of and/or 

is used as a flavoring agent in many 

foods that are commonly consumed by 

humans. When 3-decen-2-one is applied 

as a potato sprout inhibitor and used in 

accordance with good agricultural 

practices and label directions, the 

aforementioned dietary exposure is not 

likely to be substantially increased. 

A deterministic quantitative 

evaluation of potential dietary exposure 

to children (1 to 2 years) from 

consumption of pesticide-treated 

potatoes was conducted and compared 

to estimated dietary exposure to 3- 

decen-2-one as a natural constituent of 

food and as a food additive. Based on 

the results of the analysis, EPA has 

concluded that dietary exposure to 

residues of 3-decen-2-one when used as 

a pesticide will be considerably less 

than dietary exposure to the chemical as 

a naturally occurring constituent in food 

and/or as a food additive. This 

conclusion is supported by data 

obtained from the residue study 

specifically on baked potatoes, which 

demonstrated that residues of 3-decen2-one decline over time and are reduced 

when potatoes are cooked (Ref. 2). 

Based on the information in this unit, 

which includes an estimation of 

potential dietary exposure to 3-decen-2- 

one from the consumption of treated 

potatoes, the Agency concludes that 

there is a reasonable certainty that no 

harm will result to the U.S. population, 

including infants and children, from 

dietary exposure to the pesticidal 

residues of 3-decen-2-one in food. 

2. Drinking water exposure. Based on 

the proposed use pattern of the active 

ingredient as a potato sprout inhibitor 

used in indoor settings, residues in 

drinking water are not anticipated if 

products are used according to good 

agricultural practices and label 

instructions. Products containing the 

active ingredient will be used in indoor 

commercial settings only; therefore, 3- 

decen-2-one residues in drinking water 

are highly unlikely. In the unlikely 

event that exposure via drinking water 

does occur, the health risk would be 

expected to be minimal based on the 

low acute oral toxicity of 3-decen-2-one. 

B. Other Non-Occupational Exposure 

Non-occupational exposure is not 

expected from the postharvest use of 3- 

decen-2-one on stored potatoes via a 

closed system. Any exposure is 

expected to be occupational in nature. 

V. 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 exemption, EPA consider 

‘‘available information concerning the 

cumulative effects of [a particular 

pesticide’s] * * * residues and other 

substances that have a common 

mechanism of toxicity.’’ 

EPA has not found 3-decen-2-one to 

share a common mechanism of toxicity 

with any other substances, and 3-decen2-one does not appear to produce a toxic 

metabolite produced by other 

substances. For the purposes of this 

tolerance action, therefore, EPA has 

assumed that 3-decen-2-one does not 

have a common mechanism of toxicity 

with other substances. For information 

regarding EPA’s efforts to determine 

chemicals that have a common 

mechanism of toxicity and to evaluate 

the cumulative effects of such 

chemicals, see EPA’s Web site at 

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

cumulative. 

VI. Determination of Safety for U.S. 

Population, Infants and Children 

FFDCA section 408(b)(2)(C) provides 

that, in considering the establishment of 

a tolerance or tolerance exemption for a 

pesticide chemical residue, EPA shall 

assess the available information about 

consumption patterns among infants 

and children, special susceptibility of 

infants and children to pesticide 

chemical residues, and the cumulative 

effects on infants and children of the 

residues and other substances with a 

common mechanism of toxicity. In 

addition, FFDCA section 408(b)(2)(C) 

provides that EPA shall apply an 


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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 

that a different margin of safety will be 

safe for infants and children. This 

additional margin of safety is commonly 

referred to as the Food Quality 

Protection Act Safety Factor. In 

applying this provision, EPA either 

retains the default value of 10X, or uses 

a different additional or no safety factor 

when reliable data are available to 

support a different additional or no 

safety factor. 

Because there are no threshold effects 

associated with this biochemical, an 

additional margin of safety for infants 

and children is not necessary. 

EPA has determined that there are no 

foreseeable dietary risks to the U.S. 

population, including infants and 

children, from the use of 3-decen-2-one 

as a pesticide on stored potatoes when 

label instructions and good agricultural 

practices are followed. The available 

data and information indicate that the 

chemical: 

1. Is of low toxicity and is not a 

developmental toxicant; 

2. Naturally occurs in the human diet; 

3. Has been approved by FDA for use 

in foods as a food additive without 

limitation; and 

4. Is metabolized into innocuous 

substances. 

Additionally, basic exposure analyses 

that were specifically conducted for 

children aged 1–2 years suggest that 

dietary exposure from ingestion of the 

chemical as a pesticide is likely to be 

less than dietary exposure from 

ingestion of the chemical as a food 

additive and/or as a constituent that 

naturally occurs in foods (Ref. 2). When 

compared to the amount of 3-decen-2- 

one that is likely already consumed in 

the human diet, dietary exposure from 

pesticidal use is not anticipated to 

significantly increase overall dietary 

exposure of infants and children. 

Therefore, EPA concludes that there is 

a reasonable certainty that no harm will 

result to the U.S. population, including 

infants and children, from aggregate 

exposure to the residues of 3-decen-2- 

one when it is used as labeled and in 

accordance with good agricultural 

practices. Such exposure includes all 

anticipated dietary exposures and all 

other exposures for which there is 

reliable information. EPA has arrived at 

this conclusion because the data and 

information available on 3-decen-2-one 

do not demonstrate significant toxic 

potential to mammals, including infants 

and children. 

VII. Other Considerations 

A. Analytical Enforcement Methodology 

An analytical method is not required 

for enforcement purposes for the 

reasons stated in Unit VI. and because 

EPA is establishing an exemption from 

the requirement of a tolerance without 

any numerical limitation. 

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. In this context, 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 3-decen-2-one. 

C. Response to Comments 

In response to a Notice of Filing that 

published in the Federal Register of 

March 10, 2010, EPA received a 

comment from Michael J. Keim (Keim 

Aerosol Technologies) in docket ID 

number EPA–HQ–OPP–2010–0065. Mr. 

Keim believes that EPA has not been 

adequately informed [by the petitioner] 

with respect to the use of chemicals for 

the postharvest treatment of stored 

potatoes and that such use poses a risk 

to humans and the environment. His 

conclusion is based on his experience 

with the use of chlorpropham (CIPC), a 

conventional chemical that is applied 

(via thermal fog generator) in the same 

manner as the proposed product. Mr. 

Keim states that half of CIPC applied to 

stored potatoes does not deposit on the 

potatoes and, therefore, is expelled to 

the outside environment. As a result of 

this application method, Mr. Keim 

contends that EPA has not adequately 

assessed the risks to non-target 

organisms and worker/handlers. 

EPA notes that the comment from Mr. 

Keim pertains mainly to the application 

equipment used on the proposed label, 

which would be more applicable to the 

Notice of Receipt (see the Federal 

Register of March 10, 2010 (75 FR 

11175) (FRL–8811–6)) for 3-decen-2- 

one, and to the conventional chemical, 

CIPC, which, from a toxicological 

perspective, is quite different from 3- 

decen-2-one. Nonetheless, EPA will 

address Mr. Keim’s comment in this 

document. 

EPA would first direct the commenter 

to the documents in the docket for the 

Registration Review of CIPC (docket ID 

number EPA–HQ–OPP–2010–0923) as 

the Agency’s Health Effects Division 

(HED) and Environmental Fate and 

Effects Division (EFED) have already 

responded to Mr. Keim’s comments 

regarding the application equipment 

used for CIPC products and the 

potential for exposure based on the 

displacement and degradation of CIPC. 

As stated in the EPA memoranda 

listed in Unit IX., the Agency received 

and reviewed product chemistry, 

residue, mammalian toxicity, and nontarget organism data and/or information 

for this new active ingredient, 3-decen2-one, as outlined in 40 CFR 158.2030, 

158.2040, 158.2050, and 158.2060. The 

data and information submitted to EPA 

indicate that 3-decen-2-one is of low 

toxicity (with the exception that it is an 

eye and dermal irritant), no 

developmental effects were found at the 

highest dose tested (NOAEL = 1,000 mg/ 

kg/day), and 3-decen-2-one is not 

mutagenic. With regard to worker 

exposure, the thermal fogging 

application method on the proposed 

product label used for stored potatoes is 

an automated system and, as such, EPA 

considers this method a closed-delivery 

system and does not expect 

occupational handler exposure. The 

only occupational exposure expected is 

the handling of the product prior to 

application, which is mitigated by 

appropriate precautionary statements 

and personal protective equipment 

(PPE) requirements listed on the label. 

EPA has not identified any toxic 

endpoints for non-target mammals, 

birds, plants, aquatic, or soil organisms 

and has no concerns for any non-target 

organisms exposed to 3-decen-2-one 

when used in accordance with approved 

label directions. The petitioner did 

submit information that estimated the 

physical and chemical properties for 3- 

decen-2-one by using QSAR modeling 

based on the Estimation Programs 

Interface Model (EPI SuiteTM 4.0). Using 

Henry’s Law, which states that the 

solubility of a gas in a liquid is directly 

proportional to the partial pressure of 

the gas above the liquid, 3-decen-2-one 

is estimated to be 5.4 × 10¥4 atm·m3/ 

mol and indicates that the active 

ingredient has a potential for volatility 

from water or moist soil. In soil, the 

estimated Koc of 165.2–860.9 L/kg 


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Federal Register / Vol. 78, No. 34 / Wednesday, February 20, 2013 / Rules and Regulations 11765 

indicates that 3-decen-2-one would have 

medium to low mobility in soil. In 

water, an estimated log Kow of 3.28 and 

an estimated bioconcentration factor 

(BCF) of 67.41 L/kg wet-wt indicate that 

bioaccumulation in aquatic organisms is 

unlikely. In the air, atmospheric 

oxidation by hydroxyl radicals’ reaction 

is expected to occur with estimated halflives of 1.9–2.2 hours. The probability of 

biodegradation of 3-decen-2-one was 

evaluated using EPI SuiteTM 4.0 in the 

BIOWIN module. Various models in the 

BIOWIN module predicted rapid 

biodegradation of 3-decen-2-one. Based 

on a total air volume in a potato 

warehouse of 1,910 m3 and the total 

applied 3-decen-2-one of 122,475 g 

calculated by the petitioner, the 

maximum air concentration of 3-decen2-one in a potato warehouse was 

estimated to be 64.14 mg/L of air. With 

an estimated ventilation rate of 825 m3

of air/min, the air volume in a potato 

warehouse will be exchanged within 2.5 

minutes when the vents to the outdoors 

are opened. Thus, the concentration 

emitted will be rapidly diluted in the 

outside air, which further demonstrates 

insignificant exposure to non-target 

organisms. In summary, given that 3- 

decen-2-one is applied indoors in a 

closed system, has low toxicity, is 

naturally occurring in foods that are 

common in the human diet, and 

presents little, if any, risk to non-target 

organisms, EPA concludes that pesticide 

products containing this new active 

ingredient, 3-decen-2-one, are not 

expected to cause unreasonable adverse 

effects on the environment (includes 

consideration of risks to workers/ 

handlers and non-target organisms). 

VIII. Conclusion 

EPA concludes that there is a 

reasonable certainty that no harm will 

result to the U.S. population, including 

infants and children, from aggregate 

exposure to residues of 3-decen-2-one. 

Therefore, an exemption from the 

requirement of a tolerance is established 

for residues of the biochemical 

pesticide, 3-decen-2-one, in or on 

potatoes when applied as a postharvest 

potato sprout inhibitor and used in 

accordance with label directions and 

good agricultural practices. 

IX. References 

The references used in this document 

are available as ‘‘Supporting & Related 

Material’’ within docket ID EPA–HQ– 

OPP–2010–0065 at 

www.regulations.gov. 

1. U.S. EPA. 2011. Memorandum from Colin 

G. Walsh thru Angela L. Gonzales to Linda 

A. Hollis. Joint Science Review with 

Health Canada Pest Management 

Regulatory Agency (PMRA) in Support of 

the Registration of AMV–1018 Technical 

(EPA File Symbol No. 5481–LAI), a 

Manufacturing-Use Product (MP), 

Containing 98.0% of 3-decen-2-one as its 

Active Ingredient and Tolerance 

Exemption Petition Review in Support of 

3-decen-2-one. U.S. Environmental 

Protection Agency, Office of Pesticide 

Programs. December 20, 2011. 

2. U.S. EPA. 2013. Memorandum from 

Angela L. Gonzales thru Felecia A. Fort to 

Colin G. Walsh. Joint Science Review with 

Health Canada Pest Management 

Regulatory Agency (PMRA) in Support of 

the Registration of AMV–1018 Technical 

Containing 98.0% of 3-decen-2-one as its 

Active Ingredient. U.S. Environmental 

Protection Agency, Office of Pesticide 

Programs. January 3, 2013. 

3. U.S. EPA. 2010. Memorandum from Gina 

M. Casciano and Colin G. Walsh thru 

Russell S. Jones to Driss Benmhend. 

Revised Hazard Assessment for Tier I 

Human Health Toxicity in Support of the 

Registration of AMV–1018 Technical, 

Containing 3-decen-2-one as its Active 

Ingredient (Amends EPA Memorandum 

from Gina M. Casciano and Colin G. Walsh 

through Russell S. Jones to Driss 

Benmhend dated June 16, 2010). U.S. 

Environmental Protection Agency, Office 

of Pesticide Programs. December 7, 2010. 

X. Statutory and Executive Order 

Reviews 

This final rule establishes a tolerance 

exemption under FFDCA section 408(d) 

in response to a petition submitted to 

EPA. 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 exemption 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. 

As a result, this action does not alter the 

relationships or distribution of power 

and responsibilities established by 

Congress in the preemption provisions 

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

EPA 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, EPA 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 

EPA 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). 

XI. 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: February 5, 2013. 

Steven Bradbury, 

Director, 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: 


wreier-aviles on DSK5TPTVN1PROD with RULES
11766 Federal Register / Vol. 78, No. 34 / Wednesday, February 20, 2013 / Rules and Regulations 

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

■ 2. In subpart D, add § 180.1318 to read 

as follows: 

§ 180.1318 3-decen-2-one; exemption from 

the requirement of a tolerance. 

An exemption from the requirement 

of a tolerance is established for residues 

of the biochemical pesticide, 3-decen-2- 

one, in or on potatoes when applied as 

a potato sprout inhibitor and used in 

accordance with label directions and 

good agricultural practices. 

[FR Doc. 2013–03758 Filed 2–19–13; 8:45 am] 

BILLING CODE 6560–50–P 

DEPARTMENT OF THE INTERIOR 

Fish and Wildlife Service 

50 CFR Part 17 

[Docket No. FWS–R7–ES–2012–0009; 

4500030113] 

RIN 1018–AY40 

Endangered and Threatened Wildlife 

and Plants; Special Rule for the Polar 

Bear Under Section 4(d) of the 

Endangered Species Act 

AGENCY: Fish and Wildlife Service, 

Interior. 

ACTION: Final rule; availability of 

environmental assessment and Finding 

of No Significant Impact. 

SUMMARY: We, the U.S. Fish and 

Wildlife Service (Service), amends it 

regulations which implement the 

Endangered Species Act of 1973, as 

amended (ESA), to create a special rule 

under authority of section 4(d) of the 

ESA that provides measures that are 

necessary and advisable to provide for 

the conservation of the polar bear (Ursus 

maritimus), while also including 

appropriate prohibitions from section 

9(a)(1) of the ESA. 

DATES: This rule becomes effective on 

March 22, 2013. 

ADDRESSES: Document Availability: The 

final rule, final environmental 

assessment, and finding of no 

significant impact are available for 

viewing on http://www.regulations.gov 

under Docket No. FWS–R7–ES–2012– 

0009. Supporting documentation we 

used in preparing this final rule is 

available for public inspection, by 

appointment, during normal business 

hours, at the Marine Mammal 

Management Office, U.S. Fish and 

Wildlife Service, 1011 East Tudor Road, 

Anchorage, AK 99503. 

FOR FURTHER INFORMATION CONTACT: 

Charles Hamilton, Marine Mammals 

Management Office, U.S. Fish and 

Wildlife Service, Region 7, 1011 East 

Tudor Road, Anchorage, AK 99503; 

telephone 907–786–3309. Persons who 

use a telecommunications device for the 

deaf (TDD) may call the Federal 

Information Relay Service (FIRS) at 1– 

800–877–8339, 24 hours a day, 7 days 

a week. 

SUPPLEMENTARY INFORMATION: 

Executive Summary 

Why We Need To Publish a Final Rule 

The Service was challenged via 

litigation on our December 16, 2008, 

final special rule under section 4(d) of 

the ESA (hereafter referred to as 4(d) 

special rule) (16 U.S.C. 1531 et al), for 

the polar bear. The District Court for the 

District of Columbia (Court) found that, 

although the final 4(d) special rule 

published December 16, 2008 (73 FR 

76249) for the polar bear was consistent 

with the ESA, the Service violated the 

National Environmental Policy Act (42 

U.S.C. 4321 et seq.) (NEPA) and the 

Administrative Procedure Act (5 U.S.C. 

500 et seq.) by failing to conduct a 

NEPA analysis when it promulgated the 

final rule. On November 18, 2011, the 

Court vacated the final 4(d) special rule 

and ordered that the May 15, 2008, 

interim 4(d) special rule take effect until 

superseded by a new final 4(d) special 

rule. The Service is therefore 

promulgating a new final 4(d) special 

rule with appropriate NEPA analysis. 

Through the NEPA process, the Service 

fully considered a suite of alternatives 

for the special rule. 

What is the effect of this rule? 

The 2008 listing of the polar bear as 

a threatened species under the ESA is 

not affected by this final rule. In 

addition, nothing in this rule affects 

requirements applicable to polar bears 

under any other law such as the Marine 

Mammal Protection Act of 1972, as 

amended (MMPA; 16 U.S.C. 1361 et 

seq.). On-the-ground conservation 

management of the polar bear under 

both the May 15, 2008, interim 4(d) 

special rule and the December 16, 2008, 

final 4(d) special rule, were 

substantively similar; this final 4(d) 

special rule reinstates the regulatory 

parameters afforded the polar bear 

under the December 16, 2008 rule, 

which was in place until November 18, 

2011. Because this rule adopts a 

regulatory scheme that has governed 

polar bear management for over 30 

years, the requirements placed on 

individuals, local communities, and 

industry are not substantively changed. 

The Basis for Our Action 

Under section 4(d) of the ESA, the 

Secretary of the Interior (Secretary) has 

discretion to issue such regulations as 

he deems necessary and advisable to 

provide for the conservation of 

threatened species. The Secretary also 

has the discretion to prohibit by 

regulation with respect to a threatened 

species any act prohibited by section 

9(a)(1) of the ESA. 

Exercising this discretion, which has 

been delegated to the Service by the 

Secretary, the Service has developed 

general prohibitions that are appropriate 

for most threatened species in 50 CFR 

17.31 and exceptions to those 

prohibitions in 50 CFR 17.32. But for 

the polar bear, the Service has 

determined that a 4(d) special rule is 

appropriate. This 4(d) special rule 

adopts the existing conservation 

regulatory requirements under the 

MMPA and the Convention on 

International Trade in Endangered 

Species of Wild Fauna and Flora 

(CITES; 27 U.S.T. 1087) as the primary 

regulatory provisions for the polar bear. 

If an activity is authorized or exempted 

under the MMPA or CITES, no 

additional authorization under the ESA 

regulations is required, although 

consultation under section 7 of the ESA 

will also still be required if there is a 

Federal nexus. But if the activity is not 

authorized or exempted under the 

MMPA or CITES, and that activity 

would result in an act otherwise 

prohibited under the general ESA 

regulatory prohibitions for threatened 

species, then the general prohibitions at 

50 CFR 17.31 would apply, and we 

would require a permit for the activity 

as specified in our ESA regulations. 

Under this rule, incidental take 

caused by activities within the United 

States but outside the current polar bear 

range would not be subject to the 

takings prohibition under 50 CFR 17.31 

as it is for most threatened species, but 

would remain subject to the taking 

prohibition in the MMPA and, if there 

is a Federal nexus, to the consultation 

requirement of section 7 of the ESA. 

Previous Federal Actions 

On May 15, 2008, the Service 

published a final rule listing the polar 

bear (Ursus maritimus) as a threatened 

species under the ESA (73 FR 28212). At 

the same time, the Service also 

published an interim special rule for the 

polar bear under authority of section 

4(d) of the ESA that provided measures 

necessary and advisable for the 

conservation of the polar bear and 

prohibited certain acts covered in 

section 9(a)(1) of the ESA (73 FR 28306); 


wreier-aviles on DSK5TPTVN1PROD with RULES