
[Federal Register Volume 78, Number 39 (Wednesday, February 27, 2013)]
[Rules and Regulations]
[Pages 13252-13257]
From the Federal Register Online via the Government Printing Office [www.gpo.gov]
[FR Doc No: 2013-04559]


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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.

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SUMMARY: This regulation establishes tolerances for residues of 
pyroxasulfone

[[Page 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/text-idx?&c=ecfr&tpl=/ecfrbrowse/Title40/40tab_02.tpl.

C. How can I file an objection or hearing request?

    Under FFDCA section 408(g), 21 U.S.C. 346a, any person may file an 
objection to any aspect of this regulation and may also request a 
hearing on those objections. You must file your objection or request a 
hearing on this regulation in accordance with the instructions provided 
in 40 CFR part 178. To ensure proper receipt by EPA, you must identify 
docket ID number EPA-HQ-OPP-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-1H-pyrazol-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

[[Page 13254]]

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-observed-adverse-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

[[Page 13255]]

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 non-occupational, 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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    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 short-term 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)-
1H-pyrazol-4-yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole, and 
its metabolites, 5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-
pyrazol-4-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

[[Page 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]

0
1. The authority citation for part 180 continues to read as follows:

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


0
2. In Sec.  180.659:
0
a. Add alphabetically the following commodities to the table in 
paragraph (a)(2).
0
b. Add a new paragraph (a)(3).
    The additions read as follows.


Sec.  180.659  Pyroxasulfone; tolerances for residues.

    (a) * * *
    (2) * * *

------------------------------------------------------------------------
                                                               Parts per
                          Commodity                             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.

------------------------------------------------------------------------
                                                               Parts per
                          Commodity                             million
------------------------------------------------------------------------
Soybean, seed...............................................        0.06
------------------------------------------------------------------------

* * * * *
[FR Doc. 2013-04559 Filed 2-26-13; 8:45 am]
BILLING CODE 6560-50-P


