13252 Federal Register / Vol. 78, No. 39 / Wednesday, February 27, 2013 / Rules and Regulations 

(1) UL 1191, Components for Personal 

Flotation Devices. 

(2) UL 1517, Standard for Hybrid 

Personal Flotation Devices (November 

12, 1984), incorporation by reference 

approved for 46 CFR 160.077–5(e)(2); 

160.077–11(a)(5)(ii) and(g)(1); 160.077– 

15(b)(12); 160.077–17(b)(9); 160.077– 

19(a)(5) and (b)(1) through (18); 

160.077–21(c)(1) through (5); 160.077– 

23(h)(4) through (7); 160.077–27(e)(1) 

and (4); and 160.077–29(c)(5), (7), and 

(9), and (d)(1) and (5). 

■ 29. Revise § 160.176–4 to read as 

follows: 

§ 160.176–4 Incorporation by reference. 

(a) Certain material is incorporated by 

reference into this part with the 

approval of the Director of the Federal 

Register in accordance with 5 U.S.C. 

552(a). To enforce any edition other 

than that specified in paragraph (b) of 

this section, the Coast Guard must 

publish a notice of change in the 

Federal Register and make the material 

available to the public. All approved 

material is on file at the U.S. Coast 

Guard, Office of Design and Engineering 

Standards (CG–ENG), 2100 2nd Street 

SW., Stop 7126, Washington, DC 20593– 

7126 or at the National Archives and 

Records Administration (NARA). For 

information on the availability of this 

material at NARA, call 202–741–6030, 

or go to: http://www.archives.gov/

federal_register/code_of_federal_

regulations/ibr_locations.html. All 

material is available from the sources 

listed below. 

(b) ASTM International, 100 Barr 

Harbor Drive, P.O. Box C700, West 

Conshohocken, PA 19428–2959, 877– 

909–2786, http://www.astm.org. 

(1) ASTM B 117–97, Standard 

Practice for Operating Salt Spray (Fog) 

Apparatus, incorporation by reference 

approved for §§ 160.176–8; 160.176–13. 

(2) ASTM D 751–95, Standard Test 

Methods for Coated Fabrics, 

incorporation by reference approved for 

§ 160.176–13. 

(3) ASTM D 975–98, Standard 

Specification for Diesel Fuel Oils, 

incorporation by reference approved for 

§ 160.176–13. 

(4) ASTM D1434–82 (Reapproved 

2009)e1, Standard Test Method for 

Determining Gas Permeability 

Characteristics of Plastic Film and 

Sheeting—(approved May 1, 2009), 

incorporation by reference approved for 

§ 160.176–13. 

(c) Federal Aviation Administration, 

Aircraft Certification Service, 800 

Independence Avenue SW., 

Washington, DC 20591, 202–385–6346, 

http://www.faa.gov/aircraft/air_cert/

design approvals/tso. 

(1) TSO–C13d, Federal Aviation 

Administration Standard for Life 

Preservers, January 3, 1983, 

incorporation by reference approved for 

§ 160.176–8. 

(2) [Reserved] 

(d) DLA Document Services, 700 

Robbins Avenue, Building 4/D, 

Philadelphia, PA 19111–5094, 215–697– 

6396, http://www.asistdocs.com. 

(1) In Federal Test Method Standard 

No. 191A (dated July 20, 1978) the 

following methods: 

(i) Method 5100, Strength and 

Elongation, Breaking of Woven Cloth; 

Grab Method, incorporation by 

reference approved for § 160.176–13. 

(ii) Method 5132, Strength of Cloth, 

Tearing; Falling-Pendulum Method, 

incorporation by reference approved for 

§ 160.176–13. 

(iii) Method 5134, Strength of Cloth, 

Tearing; Tongue Method, incorporation 

by reference approved for § 160.176–13. 

(iv) Method 5804.1, Weathering 

Resistance of Cloth; Accelerated 

Weathering Method, incorporation by 

reference approved for § 160.176–8. 

(v) Method 5762, Mildew Resistance 

of Textile Materials; Soil Burial Method, 

incorporation by reference approved for 

§ 160.176–8. 

(2) Federal Standard No. 751a, 

Stitches, Seams, and Stitching, January 

25, 1965, incorporation by reference 

(3) MIL–L–24611—Life Preserver 

Support Package For Life Preserver, MK 

4, dated May 18, 1982, incorporation by 

reference approved for § 160.176–8. 

(e) National Institute of Standards and 

Technology (NIST) (formerly National 

Bureau of Standards), c/o 

Superintendent of Documents, U.S. 

Government Printing Office, 

Washington, DC 20402, 202.512.1800, 

http://www.gpo.gov. 

(1) Special Pub. 440, Color: Universal 

Language and Dictionary of Names; 

‘‘The Universal Color Language’’ and 

‘‘The Color Names Dictionary’’, 1976, 

incorporation by reference approved for 

§ 160.176–9. 

(2) [Reserved] 

(f) Underwriters Laboratories Inc. 

(UL), 12 Laboratory Drive, Research 

Triangle Park, NC 27709–3995, 919– 

549–1400, http://www.ul.com. 

(1) UL 1191, ‘‘Components for 

Personal Flotation Devices’’, November 

11, 1984, incorporation by reference 

approved for §§ 160.176–8; 160.176–13. 

(2) [Reserved] 

PART 162—ENGINEERING 

EQUIPMENT 

■ 30. The authority citation for part 162 

continues to read as follows: 

Authority: 33 U.S.C. 1321(j), 1903; 46 

U.S.C. 3306, 3703, 4104, 4302; E.O. 12234, 45 

FR 58801, 3 CFR, 1980 Comp., p. 277; E.O. 

12777, 56 FR 54757, 3 CFR, 1991 Comp., p. 

351; Department of Homeland Security 

Delegation No. 0170.1. 

■ 31. In § 162.027–1, revise paragraph 

(b) to read as follows: 

§ 162.027–1 Incorporation by reference. 

* * * * * 

(b) ASTM International, 100 Barr 

Harbor Drive, P.O. Box C700, West 

Conshohocken, PA 19428–2959, 877– 

909–2786, http://www.astm.org. 

(1) ASTM F1546/F1546 M–96 

(Reapproved 2012), Standard 

Specification for Fire Hose Nozzles 

(ASTM F 1546) (approved May 1, 2012), 

incorporation by reference approved for 

§§ 162.027–2; 162.027–3. 

(2) [Reserved] 

PART 193—FIRE PROTECTION 

EQUIPMENT 

■ 32. The authority citation for part 193 

continues to read as follows: 

Authority: 46 U.S.C. 2213, 3102, 3306; E.O. 

12234, 45 FR 58801, 3 CFR, 1980 Comp., p. 

277; Department of Homeland Security 

Delegation No. 0170.1. 

■ 33. In § 193.01–3, revise paragraph (b) 

introductory text and paragraph (b)(1) to 

read as follows: 

§ 193.01–3 Incorporation by reference. 

* * * * * 

(b) ASTM International, 100 Barr 

Harbor Drive, P.O. Box C700, West 

Conshohocken, PA 19428–2959, 877– 

909–2786, http://www.astm.org. 

(1) ASTM F1121–87 (Reapproved 

2010), Standard Specification for 

International Shore Connections for 

Marine Fire Applications, (approved 

March 1, 2010), incorporation by 

reference approved for § 193.10–10. 

* * * * * 

Dated: February 11, 2013. 

Kathryn A. Sinniger, 

Chief, Office of Regulations and 

Administrative Law U.S. Coast Guard. 

[FR Doc. 2013–03724 Filed 2–26–13; 8:45 am] 

BILLING CODE 9110–04–P 

ENVIRONMENTAL PROTECTION 

AGENCY 

40 CFR Part 180 

[EPA–HQ–OPP–2012–0308; FRL–9379–9] 

Pyroxasulfone; Pesticide Tolerances 

AGENCY: Environmental Protection 

Agency (EPA). 

ACTION: Final rule. 

SUMMARY: This regulation establishes 

tolerances for residues of pyroxasulfone 


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Federal Register / Vol. 78, No. 39 / Wednesday, February 27, 2013 / Rules and Regulations 13253 

in or on soybeans. K–I Chemical U.S.A., 

Inc., requested these tolerances under 

the Federal Food, Drug, and Cosmetic 

Act (FFDCA). 

DATES: This regulation is effective 

February 27, 2013. Objections and 

requests for hearings must be received 

on or before April 29, 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–2012–0308, 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: 

Kathryn Montague, Registration 

Division (7505P), Office of Pesticide 

Programs, Environmental Protection 

Agency, 1200 Pennsylvania Ave. NW., 

Washington, DC 20460–0001; telephone 

number: (703) 305–1243; email address: 

montague.kathryn@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 e-CFR 

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

40tab_02.tpl. 

C. How can I file an objection or hearing 

request? 

Under FFDCA section 408(g), 21 

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

objection to any aspect of this regulation 

and may also request a hearing on those 

objections. You must file your objection 

or request a hearing on this regulation 

in accordance with the instructions 

provided in 40 CFR part 178. To ensure 

proper receipt by EPA, you must 

identify docket ID number EPA–HQ– 

OPP–2012–0308 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 29, 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– 

2012–0308, 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 2F8005) by K–I Chemical 

U.S.A., Inc., c/o Landis International, 

Inc., 3185 Madison Hwy., P.O. Box 

5126, Valdosta, GA 31603–5126. The 

petition requested that EPA establish 

tolerances in 40 CFR part 180 for 

residues of the herbicide pyroxasulfone, 

3-[(5-(difluoromethoxy)-1-methyl-3- 

(trifluoromethyl) pyrazole-4- 

ylmethylsulfonyl]-4,5-dihydro-5,5- 

dimethyl-1,2-oxazole, and its 

metabolites M–3, 5-difluoromethoxy-1- 

methyl-3-trifluoromethyl-1H-pyrazol-4- 

carboxylic acid; M–25, 5- 

difluoromethoxy-3-trifluoromethyl-1Hpyrazol-4-yl)methanesulfonic acid; and 

M–28, 3-[1-carboxy-2-(5,5-dimethyl-4,5- 

dihydroisoxazol-3-ylthio)ethylamino]-3- 

oxopropanoic acid, calculated as the 

stoichiometric equivalent of 

pyroxasulfone, in or on soybean, seed at 

0.07 parts per million (ppm). The 

petition also requested that tolerances 

be established for residues of 

pyroxasulfone, 3-[(5-(difluoromethoxy)- 

1-methyl-3-(trifluoromethyl) pyrazole-4- 

ylmethylsulfonyl]-4,5-dihydro-5,5- 

dimethyl-1,2-oxazole, and its 

metabolites M–1, 5-difluoromethoxy-1- 

methyl-3-trifluoromethyl-1H-pyrazol-4- 

ylmethanesulfonic acid; M–3, 5- 

difluoromethoxy-1-methyl-3- 

trifluoromethyl-1H-pyrazol-4-carboxylic 

acid; and M–25, 5-difluoromethoxy-3- 

trifluoromethyl-1H-pyrazol-4- 

yl)methanesulfonic acid, calculated as 

the stoichiometric equivalent of 

pyroxasulfone in or on soybean, forage 

at 1.5 ppm and soybean, hay at 2.0 ppm. 

That document referenced a summary of 

the petition prepared by K–I Chemical 

U.S.A., Inc., the registrant, which is 

available in the docket, http:// 

www.regulations.gov. There were no 

comments received in response to the 

notice of filing. 

Based upon review of the data 

supporting the petition, EPA is 

establishing tolerances for residues of 

the herbicide pyroxasulfone and its 

metabolites as requested by the 

petitioner, except that the tolerance for 

residues in or on soybean, forage is 

lowered to 1.0 ppm and the tolerance 

for residues in or on soybean, seed is 

lowered to 0.06 ppm. 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 


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13254 Federal Register / Vol. 78, No. 39 / Wednesday, February 27, 2013 / Rules and Regulations 

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 

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 pyroxasulfone 

including exposure resulting from the 

tolerances established by this action. 

EPA’s assessment of exposures and risks 

associated with pyroxasulfone 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. 

Pyroxasulfone acute toxicity to 

mammals is low by all routes of 

exposure. Subchronic and chronic oral 

toxicity testing of pyroxasulfone in 

mice, rats, and dogs produced a variety 

of adverse effects in several target 

organs. Effects seen in animal studies 

included cardiac toxicity (increased 

cardiomyopathy in mice and rats), liver 

toxicity (centrilobular hepatocellular 

hypertrophy, histopathological, and/or 

clinical pathological indicators), 

neurotoxicity characterized by axonal/ 

myelin degeneration in the sciatic nerve 

(dog, mouse, and rat) and spinal cord 

sections (dog), skeletal muscle 

myopathy, kidney toxicity (increased 

incidence of chronic progressive 

nephropathy in dogs and retrograde 

nephropathy in mice), urinary bladder 

mucosal hyperplasia, inflammation, and 

urinary bladder transitional cell 

papillomas (rats). Decreased body 

weight and enzyme changes were noted 

in some studies. Immunotoxicity studies 

in rats and mice showed no evidence of 

immunotoxic effects from 

pyroxasulfone. 

Pyroxasulfone was moderately toxic 

to rats following a 4-week dermal 

exposure producing local inflammation 

and systemic effects of minimal to mild 

cardiac myofiber degeneration at the 

limit dose. No adverse effects were 

noted in a 28-day inhalation study at the 

highest-dose tested. 

Pyroxasulfone did not exhibit 

developmental toxicity in the rat 

developmental toxicity study and 

exhibited only slight developmental 

toxicity in rabbits (reduced fetal weight 

and resorptions) at the limit dose. 

However, developmental effects were 

noted in post-natal day (PND) 21 

offspring in the rat developmental 

neurotoxicity (DNT) study characterized 

as decreased brain weight and 

morphometric changes. Developmental 

effects in the rabbit developmental 

study and DNT study occurred in the 

absence of maternal toxicity, indicating 

potential increased quantitative 

susceptibility of offspring. In a 

reproductive toxicity in rats reduced 

pup weight and body weight gains 

during lactation occurred at similar or 

higher doses causing pronounced 

maternal toxicity (reduced body weight, 

body weight gain, and food 

consumption and increased kidney 

weight, cardiomyopathy, and urinary 

bladder mucosal hyperplasia with 

inflammation). 

In cancer studies in mice and rats, 

renal tubular adenomas were observed 

in male mice and urinary bladder 

transitional cell papillomas were 

observed in male rats. The kidney 

adenomas in male mice were 

determined to be spontaneous and not 

treatment-related based on the following 

considerations: 

1. Absence of any cytotoxicity 

(degeneration or individual cell 

necrosis) in studies ranging from 14 

days to 18 months at doses up to 15,000 

ppm. 

2. Absence of cell regeneration 

leading to precursor lesions such as 

atypical tubular hyperplasia at all time 

points and doses up to 15,000 ppm. 

3. Lack of exacerbation of chronic 

progressive nephropathy, a spontaneous 

disease in rodents that results in cell 

regeneration which can result in renal 

tubule tumors in chronic studies. 

4. Lack of a clear dose response in the 

distribution of tumors between test 

substance treated groups. 

The urinary bladder tumors seen in 

male rats were determined to be a 

threshold effect. Pyroxasulfone 

exposure causes the growth of crystals 

in the urinary tract with subsequent 

calculi formation resulting in cellular 

damage. Crystal formation in the 

absence of calculi is not associated with 

hyperplasia or urinary bladder tumors; 

therefore, the formation of urinary 

bladder calculi is the prerequisite for 

subsequent hyperplasia and neoplasia. 

In other words, urinary bladder tumors 

do not develop at doses too low to 

produce calculi. There is also a clear 

threshold of 1,000 ppm (42.55 

milligrams/kilogram/day (mg/kg/day)) 

for development of calculi and 

tumorigenesis. The point of departure 

(POD) of 50 ppm (2.0 mg/kg/day) 

selected for chronic risk assessment is 

not expected to result in urinary bladder 

calculi formation, which is a 

prerequisite for subsequent hyperplasia 

and neoplasia. Therefore, the Agency 

has determined that the quantification 

of risk using a non-linear approach (i.e., 

Reference dose (RfD)) will adequately 

account for all chronic toxicity, 

including carcinogenicity, that could 

result from exposure to pyroxasulfone. 

There is no concern for mutagenicity. 

Specific information on the studies 

received and the nature of the adverse 

effects caused by pyroxasulfone as well 

as the no-observed-adverse-effect-level 

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

toxicity studies can be found at http:// 

www.regulations.gov in document 

‘‘Pyroxasulfone Human Health Risk 

Assessment for Use on Soybeans,’’ p. 34, 

in docket ID number EPA–HQ–OPP– 

2012–0308. 

B. Toxicological Points of Departure/ 

Levels of Concern 

Once a pesticide’s toxicological 

profile is determined, EPA identifies the 

toxicological 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 

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 


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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 pyroxasulfone used for 

human risk assessment is discussed in 

Unit III.B. of the final rule published in 

the Federal Register issue of February 

29, 2012 (77 FR 12207) (FRL–9334–2). 

C. Exposure Assessment 

1. Dietary exposure from food and 

feed uses. In evaluating dietary 

exposure to pyroxasulfone, EPA 

considered exposure under the 

petitioned-for tolerances as well as all 

existing pyroxasulfone tolerances in 40 

CFR 180.659. EPA assessed dietary 

exposures from pyroxasulfone in food as 

follows: 

i. Acute exposure. Quantitative acute 

dietary exposure and risk assessments 

are performed for a food-use pesticide, 

if a toxicological study has indicated the 

possibility of an effect of concern 

occurring as a result of a 1-day or single 

exposure. 

Such effects were identified for 

pyroxasulfone. In estimating acute 

dietary exposure, EPA used food 

consumption information from the 

United States Department of Agriculture 

(USDA) National Health and Nutrition 

Examination Survey, What We Eat in 

America, (NHANES/WWEIA). As to 

residue levels in food, EPA assumed 

100% of the crop was treated with 

pyroxasulfone and that residues of the 

parent and the relevant metabolites of 

concern on soybeans are present at 

tolerance levels. 

ii. Chronic exposure. In conducting 

the chronic dietary exposure assessment 

EPA used the food consumption data 

from the USDA (NHANES/WWEIA). As 

to residue levels in food, EPA made the 

same assumptions as in the acute 

dietary exposure assessment. 

iii. Cancer. Based on the data 

summarized in Unit III.A., EPA has 

concluded that a non-linear RfD 

approach is appropriate for assessing 

cancer risk to pyroxasulfone. Cancer 

risk was assessed using the same 

exposure estimates as discussed in Unit 

III.C.1.i. 

iv. Anticipated residue and percent 

crop treated (PCT) information. EPA did 

not use anticipated residue and/or PCT 

information in the dietary assessment 

for pyroxasulfone. Tolerance level 

residues for soybean and 100 PCT were 

assumed for soybean commodities in 

the dietary assessment. 

2. Dietary exposure from drinking 

water. The Agency used screening level 

water exposure models in the dietary 

exposure analysis and risk assessment 

for pyroxasulfone in drinking water. 

These simulation models take into 

account data on the physical, chemical, 

and fate/transport characteristics of 

pyroxasulfone. Further information 

regarding EPA drinking water models 

used in pesticide exposure assessment 

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

oppefed1/models/water/index.htm. 

Based on the Pesticide Root Zone 

Model/Exposure Analysis Modeling 

System (PRZM/EXAMS) and Pesticide 

Root Zone Model Ground Water (PRZM 

GW), the estimated drinking water 

concentrations (EDWCs) of 

pyroxasulfone for acute exposures are 

estimated to be 17 parts per billion 

(ppb) for surface water and 210 ppb for 

ground water. EDWCs of pyroxasulfone 

for chronic exposures for non-cancer 

assessments are estimated to be 3.2 ppb 

for surface water and 174 ppb for 

ground water. 

Modeled estimates of drinking water 

concentrations were directly entered 

into the dietary exposure model. For 

acute dietary risk assessment, the water 

concentration value of 210 ppb was 

used to assess the contribution to 

drinking water. For chronic dietary risk 

assessment, the water concentration of 

value 174 ppb was used to assess the 

contribution to drinking water. 

3. From non-dietary exposure. The 

term ‘‘residential exposure’’ is used in 

this document to refer to nonoccupational, non-dietary exposure. 

Pyroxasulfone is not registered for any 

specific use patterns that would result 

in residential exposure. 

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.’’ 

EPA has not found pyroxasulfone to 

share a common mechanism of toxicity 

with any other substances, and 

pyroxasulfone does not appear to 

produce a toxic metabolite produced by 

other substances. For the purposes of 

this tolerance action, therefore, EPA has 

assumed that pyroxasulfone does not 

have a common mechanism of toxicity 

with other substances. For information 

regarding EPA’s efforts to determine 

which chemicals 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. 

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 

Food Quality Protection Act (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. 

The prenatal and postnatal toxicity 

database for pyroxasulfone includes 

developmental toxicity studies in rats 

and rabbits, a DNT study in rats, and a 

2-generation reproduction toxicity study 

in rats. As discussed in Unit III.A., 

evidence of increased susceptibility of 

fetuses and offspring was seen in the 

DNT study and developmental toxicity 

study in rabbits following in utero or 

postnatal exposure to pyroxasulfone. No 

increased susceptibility was seen in the 

rat developmental or reproduction 

toxicity studies. In rabbits, 

developmental toxicity was only seen at 

the limit dose of 1,000 mg/kg/day as 

reduced fetal weight and increased fetal 

resorptions with a NOAEL of 500 mg/ 

kg/day for these effects, compared to no 

maternal toxicity at these doses. In a 

DNT study in rats, offspring toxicity 

(decreased brain weight and 

orphometric changes on PND 21) was 

seen at 300 mg/kg/day compared to no 

maternal toxicity at 900 mg/kg/day. The 

degree of concern for the increased 

susceptibility seen in these studies is 

low and there are no residual 

uncertainties based on the following 

considerations: 

i. The increased susceptibility is 

occurring at high doses. 

ii. NOAELs and LOAELs have been 

identified for all effects of concern, and 

thus a clear dose response has been well 

defined. 

iii. The PODs selected for risk 

assessment are protective of the fetal/ 

offspring effects. 

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: 


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13256 Federal Register / Vol. 78, No. 39 / Wednesday, February 27, 2013 / Rules and Regulations 

i. The toxicity database for 

pyroxasulfone is complete. 

ii. Pyroxasulfone is a neurotoxic 

chemical and there is evidence of 

increased susceptibility of offspring 

with regard to neurotoxic effects in the 

rat DNT study. There is also evidence of 

increased susceptibility of fetuses/ 

offspring with regard to non-neurotoxic 

effects in the rabbit developmental 

toxicity study. However, the concern for 

the increased susceptibility is low for 

the reasons stated in Unit III.D.2., and 

EPA did not identify any residual 

uncertainties after establishing toxicity 

endpoints and traditional uncertainty 

factors (UFs) to be used in the risk 

assessment for pyroxasulfone. 

iii. There are no residual uncertainties 

in the exposure database. The dietary 

food exposure assessments were 

performed based on 100 PCT and 

tolerance-level residues), and EPA made 

conservative (protective) assumptions in 

the ground and surface water modeling 

used to assess exposure to 

pyroxasulfone in drinking water. These 

assessments will not underestimate the 

exposure and risks posed by 

pyroxasulfone. 

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). 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 

pyroxasulfone will occupy 3.6% of the 

aPAD for infants less than 1 year old, 

the population group receiving the 

greatest exposure. 

2. Chronic risk. Using the exposure 

assumptions described in this unit for 

chronic exposure, EPA has concluded 

that chronic exposure to pyroxasulfone 

from food and water will utilize 48% of 

the cPAD for infants less than 1 year 

old, the population group receiving the 

greatest exposure. There are no 

residential uses for pyroxasulfone. 

3. Short-term risk. Short-term 

aggregate exposure takes into account 

short-term residential exposure plus 

chronic exposure to food and water 

(considered to be a background 

exposure level). A short-term adverse 

effect was identified; however, 

pyroxasulfone is not registered for any 

use patterns that would result in shortterm residential exposure; therefore, no 

further assessment of short-term risk is 

necessary. 

4. Intermediate-term risk. 

Intermediate-term aggregate exposure 

takes into account intermediate-term 

residential exposure plus chronic 

exposure to food and water (considered 

to be a background exposure level). An 

intermediate-term adverse effect was 

identified; however, pyroxasulfone is 

not registered for any use patterns that 

would result in intermediate-term 

residential exposure; therefore, no 

further assessment of intermediate-term 

risk is necessary. 

5. Aggregate cancer risk for U.S. 

population. As explained in Unit III.A., 

the Agency has determined that the 

quantification of risk using a non-linear 

(i.e., RfD) approach will adequately 

account for all chronic toxicity, 

including carcinogenicity, that could 

result from exposure to pyroxasulfone. 

Therefore, based on the results of the 

chronic risk assessment discussed in 

Unit III.E.2., pyroxasulfone 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 

pyroxasulfone residues. 

IV. Other Considerations 

A. Analytical Enforcement Methodology 

Adequate enforcement methodology 

(a liquid chromatography/mass 

spectrometry/mass spectrometry (LC/ 

MS/MS) method) 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 pyroxasulfone. 

C. Revisions to Petitioned-for Tolerances 

EPA has revised the tolerance levels 

for soybean, forage and soybean, seed as 

based on analysis of the field trial data 

using the tolerance MRL calculator in 

accordance with the Organization for 

Economic Cooperation and 

Development’s ‘‘MRL Calculator User 

Guide Standard Operating Procedure 

(SOP).’’ Soybean, forage was decreased 

from 1.5 ppm to 1.0 ppm for residues of 

pyroxasulfone and its metabolites M–1, 

M–3, and M–25 and soybean, seed was 

decreased from 0.07 ppm to 0.06 ppm 

for residues of pyroxasulfone and its 

metabolites M–3, M–25, and M–28. 

V. Conclusion 

Therefore, tolerances are established 

for residues of the herbicide 

pyroxasulfone, 3-[[[5-(difluoromethoxy)- 

1-methyl-3-(trifluoromethyl)-1Hpyrazol-4-yl]methyl]sulfonyl]-4,5- 

dihydro-5,5-dimethylisoxazole, and its 

metabolites, 5-(difluoromethoxy)-1- 

methyl-3-(trifluoromethyl)-1H-pyrazol4-ylmethanesulfonic acid (M–1); 5- 

(difluoromethoxy)-1-methyl-3- 

(trifluoromethyl)-1H-pyrazol-4- 

carboxylic acid (M–3); and [5- 

(difluoromethoxy)-3-(trifluoromethyl)- 

1H-pyrazol-4-yl]methanesulfonic acid 

(M–25), calculated as the stoichiometric 

equivalent of pyroxasulfone, in or on 

soybean, forage at 1.0 ppm; soybean, 

hay at 2.0 ppm; and pyroxasulfone, 3- 

[[[5-(difluoromethoxy)-1-methyl-3- 

(trifluoromethyl)-1H-pyrazol-4- 

yl]methyl]sulfonyl]-4,5-dihydro-5,5- 

dimethylisoxazole, and its metabolites, 

5-(difluoromethoxy)-1-methyl-3- 

(trifluoromethyl)-1H-pyrazol-4- 

carboxylic acid (M–3); [5- 

(difluoromethoxy)-3-(trifluoromethyl)- 

1H-pyrazol-4-yl]methanesulfonic acid 

(M–25); and 3-[1-carboxy-2-(5,5- 

dimethyl-4,5-dihydroisoxazol-3- 

ylthio)ethylamino]-3-oxopropanoic acid 

(M–28), calculated as the stoichiometric 

equivalent of pyroxasulfone in or on 

soybean, seed at 0.06 ppm. 

VI. Statutory and Executive Order 

Reviews 

This final rule establishes tolerances 

under FFDCA section 408(d) in 

response to a petition submitted to the 


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Federal Register / Vol. 78, No. 39 / Wednesday, February 27, 2013 / Rules and Regulations 13257 

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). 

VII. 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 20, 2013. 

Lois Rossi, 

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: 

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

■ 2. In § 180.659: 

■ a. Add alphabetically the following 

commodities to the table in paragraph 

(a)(2). 

■ b. Add a new paragraph (a)(3). 

The additions read as follows. 

§ 180.659 Pyroxasulfone; tolerances for 

residues. 

(a) * * * 

(2) * * * 

Commodity Parts per 

million 

* * * * * 

Soybean, forage ......................... 1.0 

Soybean, hay .............................. 2.0 

(3) Tolerances are established for 

residues of the herbicide pyroxasulfone, 

including its metabolites and 

degradates, in or on the commodities in 

the table below. Compliance with the 

tolerance levels specified below is to be 

determined by measuring only the sum 

of pyroxasulfone, 3-[[[5- 

(difluoromethoxy)-1-methyl-3- 

(trifluoromethyl)-1H-pyrazol-4- 

yl]methyl]sulfonyl]-4,5-dihydro-5,5- 

dimethylisoxazole, and its metabolites, 

5-(difluoromethoxy)-1-methyl-3- 

(trifluoromethyl)-1H-pyrazol-4- 

carboxylic acid (M–3); [5- 

(difluoromethoxy)-3-(trifluoromethyl)- 

1H-pyrazol-4-yl]methanesulfonic acid 

(M–25); and 3-[1-carboxy-2-(5,5- 

dimethyl-4,5-dihydroisoxazol-3- 

ylthio)ethylamino]-3-oxopropanoic acid 

(M–28), calculated as the stoichiometric 

equivalent of pyroxasulfone, in or on 

the commodity. 

Commodity Parts per 

million 

Soybean, seed ............................ 0.06 

* * * * * 

[FR Doc. 2013–04559 Filed 2–26–13; 8:45 am] 

BILLING CODE 6560–50–P 

ENVIRONMENTAL PROTECTION 

AGENCY 

40 CFR Part 180 

[EPA–HQ–OPP–2011–1002; FRL–9379–6] 

Pyraflufen-ethyl; Pesticide Tolerances 

AGENCY: Environmental Protection 

Agency (EPA). 

ACTION: Final rule. 

SUMMARY: This regulation establishes 

tolerances for residues of pyraflufenethyl in or on multiple commodities 

which are identified and discussed later 

in this document. Nichino America, Inc. 

requested these tolerances under the 

Federal Food, Drug, and Cosmetic Act 

(FFDCA). 

DATES: This regulation is effective 

February 27, 2013. Objections and 

requests for hearings must be received 

on or before April 29, 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–2011–1002, 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: 

Bethany Benbow, Registration Division 


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