Document ID: EPA-HQ-OPP-2007-0596-0004
Agency: epa
Document Type: Rule
Title: (Z)-7,8-epoxy-2-methyloctadecane (Disparlure); Exemption from the Requirement of a Tolerance
Posted Date: 2008-06-13T04:00Z

[Federal Register: June 13, 2008 (Volume 73, Number 115)]
[Rules and Regulations]               
[Page 33708-33714]
From the Federal Register Online via GPO Access [wais.access.gpo.gov]
[DOCID:fr13jn08-17]                         

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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[EPA-HQ-OPP-2007-0596; FRL-8367-7]

 
(Z)-7,8-epoxy-2-methyloctadecane (Disparlure); Exemption from the 
Requirement of a Tolerance

AGENCY: Environmental Protection Agency (EPA).

ACTION: Final rule.

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SUMMARY: This regulation establishes an exemption from the requirement 
of a tolerance for residues of the (Z)-7,8-epoxy-2-methyloctadecane on 
all food and feed crops when used to treat trees, shrubs, and pastures 
resulting in unintentional spray and drift from application as well as 
unintentional

[[Page 33709]]

spray and drift to non-target vegetation including non-food, food, and 
feed crops. Aberdeen Road Company d/b/a Hercon Environmental submitted 
a petition to EPA under the Federal Food, Drug, and Cosmetic Act 
(FFDCA), as amended by the Food Quality Protection Act of 1996 (FQPA), 
requesting an exemption from the requirement of a tolerance. This 
regulation eliminates the need to establish a maximum permissible level 
for residues of (Z)-7,8-epoxy-2-methyloctadecane. This active 
ingredient (AI) is also known as Disparlure.

DATES: This regulation is effective June 13, 2008. Objections and 
requests for hearings must be received on or before August 12, 2008, 
and must be filed in accordance with the instructions provided in 40 
CFR part 178 (see also Unit I.C. of the SUPPLEMENTARY INFORMATION).

ADDRESSES: EPA has established a docket for this action under docket 
identification (ID) number EPA-HQ-OPP-2007-0596. To access the 
electronic docket, go to http://www.regulations.gov, select ``Advanced 
Search,'' then ``Docket Search.'' Insert the docket ID number where 
indicated and select the ``Submit'' button. Follow the instructions on 
the regulations.gov website to view the docket index or access 
available documents. All documents in the docket are listed in the 
docket index available in regulations.gov. Although listed in the 
index, some information is not publicly available, e.g., Confidential 
Business Information (CBI) or other information whose disclosure is 
restricted by statute. Certain other material, such as copyrighted 
material, is not placed on the Internet and will be publicly available 
only in hard copy form. Publicly available docket materials are 
available in the electronic docket at http://www.regulations.gov, or, 
if only available in hard copy, at the OPP Regulatory Public Docket in 
Rm. S-4400, One Potomac Yard (South Bldg.), 2777 S. Crystal Dr., 
Arlington, VA. The Docket Facility is open from 8:30 a.m. to 4 p.m., 
Monday through Friday, excluding legal holidays. The Docket Facility 
telephone number is (703) 305-5805.

FOR FURTHER INFORMATION CONTACT:  Andrew Bryceland, Biopesticides and 
Pollution Prevention Division (7511P), Environmental Protection Agency, 
1200 Pennsylvania Ave., NW., Washington, DC 20460-0001; telephone 
number: (703) 305-6928; e-mail address: bryceland.andrew@epa.gov.

SUPPLEMENTARY INFORMATION:

I. General Information

A. Does this Action Apply to Me?

    You may be potentially affected by this action if you are an 
agricultural producer, food manufacturer, or pesticide manufacturer. 
Potentially affected entities may include, but are not limited to:
     Crop production (NAICS code 111).
     Animal production (NAICS code 112).
     Food manufacturing (NAICS code 311).
     Pesticide manufacturing (NAICS code 32532).
    This listing is not intended to be exhaustive, but rather provides 
a guide for readers regarding entities likely to be affected by this 
action. Other types of entities not listed in this unit could also be 
affected. The North American Industrial Classification System (NAICS) 
codes have been provided to assist you and others in determining 
whether this action might apply to certain entities. If you have any 
questions regarding the applicability of this action to a particular 
entity, consult the person listed under FOR FURTHER INFORMATION 
CONTACT.

B. How Can I Access Electronic Copies of this Document?

    In addition to accessing an electronic copy of this Federal 
Register document through the electronic docket at http://
www.regulations.gov, you may access this ``Federal Register'' document 
electronically through the EPA Internet under the ``Federal Register'' 
listings at http://www.epa.gov/fedrgstr. You may also access a 
frequently updated electronic version of 40 CFR part 180 through the 
Government Printing Office's pilot e-CFR site at http://
www.gpoaccess.gov/ecfr.

C. Can I File an Objection or Hearing Request?

    Under section 408(g) of FFDCA, as amended by FQPA, any person may 
file an objection to any aspect of this regulation and may also request 
a hearing on those objections. The EPA procedural regulations which 
govern the submission of objections and requests for hearings appear in 
40 CFR part 178. 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-2007-0596 in the subject line on the first page of 
your submission. All requests must be in writing, and must be mailed or 
delivered to the Hearing Clerk on or before August 12, 2008.
    In addition to filing an objection or hearing request with the 
Hearing Clerk as described in 40 CFR part 178, please submit a copy of 
the filing that does not contain any CBI for inclusion in the public 
docket that is described in ADDRESSES. Information not marked 
confidential pursuant to 40 CFR part 2 may be disclosed publicly by EPA 
without prior notice. Submit your copies, identified by docket ID 
number EPA-HQ-OPP-2007-0596, by one of the following methods.
     Federal eRulemaking Portal: http://www.regulations.gov. 
Follow the on-line instructions for submitting comments.
     Mail: Office of Pesticide Programs (OPP) Regulatory Public 
Docket (7502P), Environmental Protection Agency, 1200 Pennsylvania 
Ave., NW., Washington, DC 20460-0001.
     Delivery: OPP Regulatory Public Docket (7502P), 
Environmental Protection Agency, Rm. S-4400, One Potomac Yard (South 
Bldg.), 2777 S. Crystal Dr., Arlington, VA. Deliveries are only 
accepted during the Docket's normal hours of operation (8:30 a.m. to 4 
p.m., Monday through Friday, excluding legal holidays). Special 
arrangements should be made for deliveries of boxed information. The 
Docket Facility telephone number is (703) 305-5805.

II. Background and Statutory Findings

    In the Federal Register of August 1, 2007 (72 FR 42070) (FRL-8141-
5), EPA issued a notice pursuant to section 408(d)(3) of FFDCA, 21 
U.S.C. 346a(d)(3), announcing the filing of a pesticide tolerance 
petition (PP 6F7141) by Aberdeen Road Company d/b/a Hercon 
Environmental, P.O. Box 453, Emigsville, PA 17318-0435. The petition 
requested that 40 CFR part 180 be amended by establishing an exemption 
from the requirement of a tolerance for residues of (Z)-7,8-epoxy-2-
methyloctadecane. This notice included a summary of the petition 
prepared by the petitioner Aberdeen Road Company d/b/a Hercon 
Environmental.
    There was only one comment received in response to the notice of 
filing. The commenter suggested that there should not be an exemption 
for (Z)-7,8-epoxy-2-methyloctadane because the commenter felt that 
``plants should not have to grow with toxic chemicals on them;'' that 
the Agency ``is not protecting the public health of the American public 
which is dying from all kinds of cancers;'' and further of not properly 
evaluating pesticides in general.
    Agency Response: (Z)-7,8-epoxy-2-methyloctadecane is a naturally

[[Page 33710]]

occurring substance produced by the female gypsy moth (Lymantria 
dispar) as a pheromone to attract the male gypsy moth. The activity of 
this pesticide is specific to the Gypsy moth, and when applied to 
forests, it confuses the male gypsy moth searching for a mate; this 
reduces the moth population's ability to successfully reproduce itself 
without killing individuals in the population. The Agency's assessment 
of the naturally occurring pheromone's specific, non-toxic mode of 
action, its low acute toxicity and exposure profiles (see Unit III.), 
and its intended non-food uses indicate negligible dietary risks 
associated with the unintended application of (Z)-7,8-epoxy-2-
methyloctadecane to areas adjacent to agricultural areas (Refs. 2 and 
3).
    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 section 408(c)(2)(B) of FFDCA, in 
establishing or maintaining in effect an exemption from the requirement 
of a tolerance, EPA must take into account the factors set forth in 
section 408(b)(2)(C) of FFDCA, which require 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.... 
'' Additionally, section 408(b)(2)(D) of FFDCA requires that 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 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 section 408(b)(2)(D) of FFDCA, EPA has 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 has also 
considered available information concerning the variability of the 
sensitivities of major identifiable subgroups of consumers, including 
infants and children.
    The AI, (Z)-7,8-epoxy-2-methyloctadecane (also known as 
Disparlure), is an aliphatic hydrocarbon compound containing 19 carbons 
and a single epoxide bond. It is a naturally occurring lepidopteran 
pheromone produced by female gypsy moths (Lymantria dispar) to attract 
males. When used as a pesticide, the pheromone is intended to disrupt 
mating by disorienting males during their in-flight search for females. 
(Z)-7,8-epoxy-2-methyloctadecane was registered by the Agency in 1986 
as a non-food use pesticide to lower the incidences of gypsy moth 
mating in residential, municipal, and shade tree areas; recreational 
areas such as campgrounds, golf courses, parks and parkways; ornamental 
and shade tree forest planting; shelter belts, rights of way and other 
easements. While (Z)-7,8-epoxy-3-methyloctadecane is not intended to be 
sprayed directly on food or feed crops, the Agency has expressed 
concern that there may be a potential for regular and significant 
exposure from residues of the pesticide on food and feed crops as a 
result of unintentional spray or drift. Therefore, at the 
recommendation of the Agency, a request to establish an exemption for 
the requirement of a tolerance has been made by the applicant.
    This tolerance exemption is supported by toxicity data on a 
structurally related substance, epoxylated soybean oil (ESO), in 
anticipation of frequent and significant exposure to food and feed 
crops near treated areas. All the data normally required to support a 
tolerance exemption are not available for (Z)-7,8-epoxy-2-
methyloctadecane; therefore, the data on ESO was submitted to address 
concerns about inadvertent residues on food or feed crops. The Agency 
has agreed to consider the toxicity data on epoxylated soybean oil, 
since it is chemically similar to (Z)-7,8-epoxy-2-methyloctadecane 
(Disparlure), and the data requirements normally required for a food 
use can support an assessment of potential dietary risks associated 
with possible residues of the pesticide from spray drift (Refs. 1, 2 
and 3).
    Historically the AI, (Z)-7,8-epoxy-2-methyloctadecane, has been 
used as a non food use pesticide and, therefore, no data that address 
the data requirements required by the Agency in support of food use 
pesticides have been generated using this AI. Therefore, in order to 
satisfy these data requirements and address the issue of whether or not 
food and feed crops that are inadvertently affected by residues of (Z)-
7,8-epoxy-2-methyloctadecane are safe, the Agency has bridged from 
toxicity data generated on a structurally related substance, epoxylated 
soybean oil, to both satisfy the food use toxicity data requirements 
for (Z)-7,8-epoxy-2-methyloctadecane and to conduct a risk assessment. 
As stated in this Unit, data normally required for a food use can 
support an assessment of potential dietary risks associated with 
possible residues of the pesticide from spray drift (Refs. 1 and 3).
    ESO is a compound that is structurally related to (Z)-7,8-epoxy-2-
methyloctadecane and has already been fully assessed by the Agency as 
an inert ingredient. ESO and (Z)-7,8-epoxy-2-methyloctadecane are 
similar, from a structural perspective, in that both compounds contain 
one or more epoxide bonds, thus the basis for the Agency's decision to 
allow the bridging of toxicity data from ESO to (Z)-7,8-epoxy-2-
methyloctadecane. Epoxide bonds are three-membered rings, made up of 2 
carbons and 1 oxygen, bonded together in a triangular shape. The 
epoxide bond is very unstable in the environment and this instability 
makes the bond very reactive such that it reacts to whatever is in the 
environment (i.e. proteins, nucleophiles) (Refs. 3 and 4). This 
information is key in determining the potential risks to the (Z)-7,8-
epoxy-2-methyloctadecane compound since it is the reactive epoxide 
groups in both compounds that mostly contribute to the toxicological 
activity itself (Refs. 3 and 4). Epoxides in general are formed outside 
of the body (environmental epoxides) or they are synthesized in the 
body. Environmental epoxides are generally less toxic than epoxides 
that are synthesized in the body (Refs. 3 and 4). Both epoxides behave 
in the environment in the same way. The epoxide content of (Z)-7,8-
epoxy-2-methyloctadecane is double that of ESO. While this information 
does suggest that (Z)-7,8-epoxy-2-methyloctadecane could be more 
reactive than ESO, this potential toxicity is essentially attributed to 
the fact that (Z)-7,8-epoxy-2-methyloctadecane has more epoxide groups 
(16%) than ESO (8%). Even

[[Page 33711]]

though there are more reactive epoxide groups that belong to (Z)-7,8-
epoxy-2-methyloctadecane, these reactive epoxides are environmental 
epoxides (i.e. found outside the body), and based on the literature, 
and as stated in Unit IV., the second paragraph, environmental epoxides 
are less toxic than those synthesized in the body (Refs. 3 and 4).
    As stated in this Unit, environmental epoxides, such as (Z)-7,8-
epoxy-2-methyloctadecane react in the environment. When the AI is 
released into the environment the epoxide groups of the AI will most 
likely interact with nucleophilic sites in the environment, such as 
proteins in food, and will not be absorbed in their active form (Refs. 
3 and 4). Based on the behavior of environmental epoxides, such as this 
AI, the Agency has extrapolated the potential risks (if any) to humans 
and animals from consuming food and/or feed commodities the contain 
residues of (Z)-7,8-epoxy-2-methyloctadecane as a result of indirect or 
unintended spray or drift. The Agency has determined that even if 
residues of the AI were to occur on food/feed commodities, the reaction 
of epoxides in (Z)-7,8-epoxy-2-methyloctadecane (Disparlure) would in 
all probability react with proteins (such as those already found in 
foods) during digestion and would not be absorbed in their active form 
to cause any toxicological effects (Refs. 3 and 4). Additionally, there 
are also a number of ways the body can detoxify epoxides like 
Disparlure if they are absorbed in an active form (Ref. 4). These are:
    1. Spontaneous decomposition,
    2. Nonenzymatic reaction with glutathione,
    3. Reaction with glutathione catalyzed by glutathione transferase,
    4. Hydration by epoxide hydrolase, and
    5. Minor mechanisms such as cytochrome P450 hydrolysis (Refs. 3 and 
4).
    Further, acute oral toxicity studies on both substances indicated 
that their toxicity is low (Toxicity Category IV) which is consistent 
with these general characteristics of environmental epoxides. 
Therefore, use of toxicity data on ESO to define endpoints for the 
assessment of dietary exposure estimates associated with inadvertent 
treatment of food or feed crops with (Z)-7,8-epoxy-2-methyloctadecane 
(Disparlure) is reasonable. ESO data - including application of maximum 
uncertainty factors - define endpoints used in risk characterization 
for (Z)-7,8-epoxy-2-methyloctadecane, and data requirements to support 
the petition for exemption from the requirement of tolerances for the 
AI have been waived by the Agency based on the negligible risks 
described in this Unit.

A. Acute Toxicity

    Acute oral toxicity (rat) (OPPTS GLN 870.1100): Based on acute oral 
toxicity studies in rats, (Z)-7,8-epoxy-2-methyloctadecane has very low 
toxicity and is classified into Toxicity Category IV. No adverse 
effects or deaths were seen in rats that received an oral dose of 
undiluted (Z)-7,8-epoxy-2-methyloctadecane at 5,000 milligram per 
kilogram of bodyweight (mg/kg/bw) (Master Record Identification (MRID) 
Number 45529801). ESO also has very low acute oral toxicity lethal dose 
(LD)50 > 5,000 mg/kg (Toxicity Category IV; Refs. 2 and 3).

B. Chronic Toxicity and Carcinogenicity (OPPTS GLN 870.3100; 870.4100 
and 870.4200)

    Information from The Scientific Panel on Food Additives (European 
Commission on Food Safety) was considered which included a two-year 
chronic oral toxicity study in rats given diets containing up to 5% 
ESO. The no observed adverse effect level (NOAEL) was approximately 140 
mg/kg/day and the lowest observed adverse effect level (LOAEL) was 
approximately 1,400 mg/kg/day. Observed effects were slight changes in 
liver, kidney and uterus weights. The published summary also concluded 
that ESO was not carcinogenic when fed to rats. Based on the data, a 
tolerable daily intake of 1 mg/kg/day was determined for ESO (Refs. 1, 
2, and 3).

C. Developmental Toxicity (OPPTS GLN 870.3700 and 870.3800)

    The European Food Safety Authority (EFSA) report (2004) also 
described a developmental toxicity study in which ESO was given to 
pregnant rats during gestation at daily oral doses of 0, 100, 300 or 
1,000 mg/kg/day (Ref. 1). No maternal or developmental effects were 
noted at any dose level according to the summary submitted (Ref. 3).

D. Reproductive Toxicity (OPPTS GLN 870.3800)

    The EFSA review indicated that ESO was administered daily by oral 
gavage to rats at the 100, 300 and 1,000 mg/kg bw/day dose levels for 
71 and 15 days before mating in males and females, respectively, until 
day 21 post-partum of F1 litters; no toxic effects were noted in 
parental animals or their offspring (Ref. 1). Under the experimental 
conditions, the highest tested dose of 1,000 mg/kg bw/day was found to 
be the NOAEL, and no LOAEL was reported (Ref. 3).

E. Genotoxicity (OPPTS GLN 870.5000; MRID 45309502)

    A bacterial reverse mutation assay using Salmonella typhimurium and 
Escherichia coli was conducted on (Z)-7,8-epoxy-2-methyloctadecane with 
and without activation. The study concluded that (Z)-7,8-epoxy-2-
methyloctadecane was not mutagenic in bacteria under the conditions of 
the study.

F. Hazard Characterization

    In assessing the hazard associated with (Z)-7,8-epoxy-2-
methyloctadecane, its has been characterized in terms of epoxylated 
soybean oil. All toxicological effects were observed at or above limit 
doses (>=5,000 mg/kg/bw for acute oral toxicity and >=1,000 mg/kg/bw/
day for reproductive, developmental and chronic toxicity studies) (Ref. 
3). Based upon the Agency's standard hazard assessment protocol, if 
there is an incomplete data set for assessment of developmental 
toxicity (studies in two species) and a one-generation reproduction 
toxicity study (rather than a multi-generation reproduction study), an 
uncertainty factor of 3X is retained for consideration of the 
sensitivity of infants and children (Ref. 3). Moreover, there is 
uncertainty regarding the structure-activity relationship between 
Disparlure and ESO (16% versus 7-8% epoxide by weight, respectively) 
and the lack of repeated-dose studies on both substances to adequately 
support bridging from ESO data to Disparlure (at least one repeated-
dose study on both substances) for purposes of assessing the dietary 
risks associated with use of the mating disruptor (Ref. 3). To account 
for this, an additional 10X uncertainty factor is applied (Ref 3). 
Therefore, the 1,000 mg/kg/day endpoint was divided by 1,000 for 
general population risk characterizations (uncertainty factors of 10X 
for interspecies extrapolation, 10X for intraspecies variation, and 10X 
for uncertainties regarding bridging from data on a surrogate 
substance) to determine a reference dose (RfD) of 1 mg/kg/day; a 
population adjusted dose (PAD) of 0.33 mg/kg/day for infants and 
children is determined when the FQPA safety factor (3X) is retained 
(Ref. 3).
    Comparing this with the maximum estimated exposure for pesticidal 
use of Disparlure, the result does not exceed the Agency's level of 
concern (LOC) because the estimated exposure is less than 1% of the RfD 
(Ref. 3). Based on the behavior of epoxides in the environment and 
during ingestion, we conclude that toxicologically significant

[[Page 33712]]

residues will not result (refer to Unit III.; Refs. 3 and 4). Even when 
the maximum potential for inadvertent residues from the non-food uses 
of this pesticide are compared with the most conservative estimate of 
hazard, there is reasonable certainty that no harm will result to the 
U.S. population from exposure to this pesticide when used according to 
label instructions (Ref. 3). In the event that a food-use is requested, 
the Agency would require repeated-dose studies such as a 90-day 
subchronic feeding study (OPPTS 870.3100) and a prenatal developmental 
toxicity study (OPPTS 870.3700) on Disparlure.

IV. Aggregate Exposures

    In examining aggregate exposure, section 408 of FFDCA directs EPA 
to consider available information concerning exposures from the 
pesticide residue in food and all other non-occupational 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).
    In general, the epoxide (oxirane ring formed by an oxygen and two 
carbon atoms) is the reactive group in (Z)-7,8-epoxy-2-methyloctadecane 
and other epoxides, and is expected to contribute the most to 
biological or toxicological activity of (Z)-7,8-epoxy-2-
methyloctadecane (Ref. 4; see Ref. 3). The unstable oxirane ring can 
open and react with DNA, protein, or other nucleophilic substances. 
This means that if (Z)-7,8-epoxy-2-methyloctadecane were to be ingested 
then most likely the epoxide would react with the proteins in food 
during digestion (i.e. it would be digested). As stated in the 
literature (deBethizy and Hayes (Ref. 4), epoxides formed in animals 
are apparently more toxic than those present in the environment because 
they react with proteins and DNA in the animal's tissue (Refs. 3 and 
4). If the AI were to result on food/feed commodities, the epoxide or 
reactive group of that AI is more likely to break down and react with 
nucleophiles and proteins that are found in food and would not be 
absorbed in their active form (Refs. 3 and 4). However, even if they 
are absorbed in their active form, epoxides can be detoxified in the 
human body via:
    1. Spontaneous decomposition,
    2. Nonenzymatic reaction with glutathione,
    3. Reaction with glutathione catalyzed by glutathione transferase,
    4. Hydration by epoxide hydrolase, and
    5. Minor mechanisms such as cytochrome P450 hydrolysis (Ref.s 3 and 
4).
    In general, these considerations are expected to reduce the 
potential risk.

A. Dietary Exposure

    In examining aggregate exposure, section 408 of the FFDCA directs 
EPA to consider available information concerning exposures from the 
pesticide residue in food and on all other non-occupational 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).
    Given the use pattern of this AI, residues of the AI on food/feed 
crops as a result of unintentional spray or drift, as stated throughout 
this document, is not expected. However, the Agency has determined that 
even if residues of the AI were to occur on food/feed commodities, the 
reactive groups of the active would not be absorbed in their active 
form to cause any toxicological effects. While it is reasonable to 
assume that no toxicological effects would occur given the unliklihood 
of absorption and the low toxicity of the AI, the EPA has further 
examined the potential for dietary exposure from unintentional spray or 
drift and absorption and has estimated the potential risks (if any) to 
humans, including infants and children, from the consumption of food 
commodities that have been inadvertently treated with the AI. Assuming 
that dietary exposure has occurred the Agency considered potential 
exposure estimates for two representative scenarios including pasture 
grass and apple orchards.
    1. Food -- i. Apples. The Agency used apples as one representative 
in conducting its food assessment since apples are a significant 
commodity by a sensitive subpopulation (infants and children). For the 
apple exposure analysis, the Agency obtained a kg apples/A value from 
U.S. Department of Agriculture (USDA) statistics and used the worst-
case application rate of 60 grams (g) (Z)-7,8-epoxy-2-methyloctadecane/
Acre (A) (two applications of 30 g/A per season) for an apple orchard 
(unintentional application). The maximum potential concentration of 
(Z)-7,8-epoxy-2-methyloctadecane was estimated to be 6 mg/AI/kg of 
apples (i.e., 6 parts per million (ppm); Ref 3). This 6 ppm value is an 
overestimate because its determination assumes: All the (Z)-7,8-epoxy-
2-methyloctadecane is directly applied to an apple orchard (a misuse) 
and all of the AI applied will be on or in the apples (not sticking to 
foliage or other inedible plant parts). (Z)-7,8-epoxy-2-
methyloctadecane residues are also likely to be reduced by their 
reactivity, the AI's physical/chemical properties, and washing or 
processing treated apples before their consumption (Ref. 3).
    Based on the amount of the AI/kg of crop it was determined that the 
amount of (Z)-7,8-epoxy-2-methyloctadecane consumed from treated apples 
for the general population, children, and adults would be 0.005, 0.03 
and 0.002 mg/A.I./kg/bw per day, respectively (Ref. 3). As noted in the 
introduction to this Unit IV. Aggregate Exposures, by the time 
Disparlure-treated apples are consumed, the epoxides in the AI are 
likely to have broken down or reacted with nucleophiles such as 
proteins in the apples and would not be absorbed in their active form 
(Refs. 3 and 4).
    ii. Pasture. A pasture grass exposure analysis was presented in the 
applicant's petition, which was based on maximum recommended single 
application rates (30 g/AI/A) and a model for estimating potential 
exposure for grazing cattle (described at http://www.epa.gov/oppefed1/
ecorisk_ders/toera_analysis_exp.htm). The largest estimate was 
determined to be 0.14 mg Disparlure/kg cattle body weight per day (Ref. 
3). This estimate of the potential exposure was based on the assumption 
that all the Disparlure applied to an acre of short grass would be 
consumed as if the AI was intentionally applied to the pasture rather 
than drifting from a nearby treated area (Ref. 3). A more realistic 
assumption in the exposure analysis was that 10% or less of the pasture 
grass would be impacted by spray drift, thereby reducing the exposure 
estimate to 0.014 mg Disparlure/kg cattle bw/day (Ref. 3). Also, 
applications in any given area would not be done more than one or two 
days each year which further reduces the potential exposure to cattle. 
As noted in the second paragraph of Unit IV., the metabolic pathways 
that break down epoxides in animals are expected to further reduce the 
potential for dietary exposure preventing detection or bioaccumulation 
of Disparlure residues in cattle feeding on inadvertently treated 
pasture grass. Therefore, a dietary assessment for meat, milk and meat 
by-products was not conducted by the Agency (Ref 3).
    2. Drinking water exposure. Exposure to residues of (Z)-7,8-epoxy-
2-methyloctadecane in consumed drinking water is unlikely because of 
the reactivity of such epoxides in the environment (see discussion 
under Unit IV. Aggregate Exposure; Refs. 3 and 4),

[[Page 33713]]

and the AI is not directly applied to water. Therefore, drinking water 
exposure is not expected to pose any quantifiable risks due to a lack 
of residues of toxicological concern.

B. Other Non-Occupational Exposure

    There are no residential, school, or day care uses proposed for 
(Z)-7,8-epoxy-2-methyloctadecane (Disparlure). Since the proposed use 
is for agricultural non-food crops the potential for non-occupational, 
non-dietary exposures to (Z)-7,8-epoxy-2-methyloctadecane by the 
general population, including infants and prolonged inhalation exposure 
to non-sticking flakes in unlikely (Ref. 2).

V. Cumulative Effects

    Section 408(b)(2)(D)(v) of FFDCA requires that, when considering 
whether to establish an exemption from 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.'' These considerations include the possible 
cumulative effects of such residues on infants and children. EPA has 
considered the potential for cumulative effects of (Z)-7,8-epoxy-2-
methyloctadecane and other substances in relation to common mechanism 
of toxicity. Common mechanisms of toxicity are not relevant to a 
consideration of cumulative exposure to (Z)-7,8-epoxy-2-
methyloctadecane because it is not toxic to mammalian systems. Because, 
since Disparlure is an environmental epoxides (formed outside the body) 
which are generally considered less toxic than epoxides synthesized 
inside the body (Ref. 4). The reactive epoxide in Disparlure's 
structure would most likely react with proteins in food during 
digestion and would not be absorbed in their active form to induce 
toxicological effects (Ref. 4). There are also a number of ways the 
body can detoxify epoxides like Disparlure if they are absorbed in an 
active form (Ref. 4). Also the acute oral toxicity study on Disparlure 
indicated that the toxicity is low (Toxicity Category IV). Thus, the 
Agency does not expect any cumulative or incremental effects from 
exposure to residues of (Z)-7,8-epoxy-2-methyloctadecane when applied/
used as directed on the label and in accordance with good agricultural 
practices. Additionally, when comparing the most conservative estimate 
of hazard to the maximum potential for inadvertent residues from the 
non-food uses of Disparlure, the result does not exceed the Agency's 
LOC (i.e.: Estimated exposure is less than 1% of the RfD; Ref. 3). 
Margins of Exposure (MOE) based on estimated exposure and hazard (the 
140 mg/kg/day NOAEL from a chronic toxicity study in rats) range from 
4,600 to 65,000 (Ref. 3). When the resulting MOE is greater than 100, 
the Agency's LOC is not exceeded and there is reasonable certainty of 
no harm to human health (Ref. 3).

VI. Determination of Safety for U.S. Population, Infants and Children

    1. U.S. population. The Agency has determined that there is 
reasonable certainty that no harm will result to the U.S. Population 
from aggregated exposure to residues of (Z)-7,8-epoxy-2-
methyloctadecane. This includes all dietary exposures and other 
exposures for which there is reliable information. The Agency has 
arrived at this conclusion based on the chemicals low acute toxicity, 
it is a naturally occurring lepidopteran pheromone produced by female 
gypsy moths (Lymantria dispar), is similar in chemical structure to 
compounds of low chronic toxicity (ESO), and has a very low potential 
for human exposure. (Ref. 2).
    2. Infants and children. FFDCA section 408 provides that EPA shall 
apply an additional tenfold MOE for infants and children in the case of 
threshold effects. Margins of exposure are often referred to as 
uncertainty or safety factors, and are used to account for potential 
prenatal and postnatal toxicity and any lack of completeness of the 
database. Based on available data and other information, EPA may 
determine that a different MOE will define a level of concern for 
infants and children or that a MOE approach is not appropriate. Based 
on all the available information the Agency reviewed on (Z)-7,8-epoxy-
2-methyloctadecane, including a lack of threshold effects, the Agency 
concluded that (Z)-7,8-epoxy-2-methyloctadecane is practically non-
toxic to mammals, including infants and children. Since there are no 
effects of concern, the provision requiring an additional margin of 
safety does not apply.

VII. Other Considerations

A. Endocrine Disruptors

    There is no evidence to suggest that (Z)-7,8-epoxy-2-
methyloctadecane functions in a manner similar to any known hormone, or 
that it acts as an endocrine disrupter.

B. Analytical Method

    Because this is an exemption from the requirement of a tolerance 
without numerical limitations, no analytical method is required.

C. Codex Maximum Residue Level

    There are no CODEX maximum residue levels for residues for (Z)-7,8-
epoxy-2-methyloctadecane for unintentional spray or drift from 
application when treating trees and shrubs along or within pastures, as 
well as unintentional spray and drift to non-target vegetation 
including native and ornamental species, and food and feed crops.

VIII. Conclusions

    Based on the low toxicity in animal testing, and the expected low 
exposure to humans, no risk to human health is expected from use of the 
chemical on food crops.

IX. References

    1. EFSA. (2004) Opinion of the Scientific Panel on Food Additives, 
Flavorings, Processing Aids and Materials in Contact with Food (AFC) on 
a request from the Commission related to the use of Epoxidized soybean 
oil in food contact materials. EFSA Journal 64: 1-17.
    2. Gonzales, A. (June 27, 2007) USEPA Memorandum - Tolerance 
Exemption Petition Review for (Z)-7,8-epoxy-2-methyloctadecane.
    3. Gardner, R. & A. Gonzales (January 8, 2008) USEPA Memorandum - 
Dietary Risk Considerations Supporting a Petition for Exemption from 
the Requirement of a Tolerance for (Z)-7,8-epoxy-2-methyloctadecane.
    4. de Bethizy, J.D., and J.R. Hayes. 2001. ``Metabolism: 
Determinant of Toxicity'' Ch. 3 in Principles and Methods of 
Toxicology, 4th Edition. A.W. Hayes, ed. Taylor & Francis. 
Philadelphia, PA. pp. 123-124.

 X. Statutory and Executive Order Reviews

    This final rule establishes a tolerance under section 408(d) of 
FFDCA in response to a petition submitted to the Agency. The Office of 
Management and Budget (OMB) has exempted these types of actions from 
review under Executive Order 12866, entitled Regulatory Planning and 
Review (58 FR 51735, October 4, 1993). Because this final rule has been 
exempted from review under Executive Order 12866, this final rule is 
not subject to Executive Order 13211, 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).

[[Page 33714]]

This final rule does not contain any information collections subject to 
OMB approval under the Paperwork Reduction Act (PRA), 44 U.S.C. 3501 et 
seq., nor does it require any special considerations under Executive 
Order 12898, entitled Federal Actions to Address Environmental Justice 
in Minority Populations and Low-Income Populations (59 FR 7629, 
February 16, 1994).
    Since tolerances and exemptions that are established on the basis 
of a petition under section 408(d) of FFDCA, such as the tolerance in 
this final rule, do not require the issuance of a proposed rule, the 
requirements of the Regulatory Flexibility Act (RFA) (5 U.S.C. 601 et 
seq.) do not apply.
    This final rule directly regulates growers, food processors, food 
handlers, and food retailers, not States or tribes, nor does this 
action alter the relationships or distribution of power and 
responsibilities established by Congress in the preemption provisions 
of section 408(n)(4) of FFDCA. As such, the Agency has determined that 
this action will not have a substantial direct effect on States or 
tribal governments, on the relationship between the national government 
and the States or tribal governments, or on the distribution of power 
and responsibilities among the various levels of government or between 
the Federal Government and Indian tribes. Thus, the Agency has 
determined that Executive Order 13132, entitled Federalism (64 FR 
43255, August 10, 1999) and Executive Order 13175, entitled 
Consultation and Coordination with Indian Tribal Governments (65 FR 
67249, November 9, 2000) do not apply to this final rule. In addition, 
this final rule does not impose any enforceable duty or contain any 
unfunded mandate as described under Title II of the Unfunded Mandates 
Reform Act of 1995 (UMRA) (Public Law 104-4).
    This action does not involve any technical standards that would 
require Agency consideration of voluntary consensus standards pursuant 
to section 12(d) of the National Technology Transfer and Advancement 
Act of 1995 (NTTAA), Public Law 104-113, section 12(d) (15 U.S.C. 272 
note).

XI. Congressional Review Act

    The Congressional Review Act, 5 U.S.C. 801 et seq., generally 
provides that before a rule may take effect, the agency promulgating 
the rule must submit a rule report to each House of the Congress and to 
the Comptroller General of the United States. EPA will submit a report 
containing this rule and other required information to the U.S. Senate, 
the U.S. House of Representatives, and the Comptroller General of the 
United States prior to publication of this final rule in the Federal 
Register. This final rule is not a ``major rule'' as defined by 5 
U.S.C. 804(2).

List of Subjects in 40 CFR Part 180

    Environmental protection, Administrative practice and procedure, 
Agricultural commodities, Pesticides and pests, Reporting and 
recordkeeping requirements.

    Dated: May 30, 2008.
Marty Monell,
Acting Director, Office of Pesticide Programs.

0
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. Section 180.1283 is added to subpart D to read as follows:

Sec.  180.1283  (Z)-7,8-epoxy-2-methyloctadecane (Disparlure); 
exemption from the requirement of a tolerance.

    An exemption from the requirement of a tolerance is established for 
residues of (Z)-7,8-epoxy-2-methyloctadecane on all food and feed crops 
that occur when it is used to treat trees, shrubs, and pastures and 
such use results in unintentional spray and drift to non-target 
vegetation including non-food, food, and feed crops. This active 
ingredient is also known as Disparlure.
[FR Doc. E8-13232 Filed 6-12-08; 8:45 am]

BILLING CODE 6560-50-S