[Federal Register: June 23, 2004 (Volume 69, Number 120)]
[Rules and Regulations]               
[Page 34937-34944]
From the Federal Register Online via GPO Access [wais.access.gpo.gov]
[DOCID:fr23jn04-15]                         

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ENVIRONMENTAL PROTECTION AGENCY

40 CFR Part 180

[OPP-2003-0379; FRL-7352-6]

 
C8, C10, and C12 Straight-Chain Fatty Acid Monoesters of Glycerol 
and Propylene Glycol; 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 C8, C10, and C12 straight-chain 
fatty acid monoesters of glycerol and propylene glycol on all raw 
agricultural commodities and food when applied/used in accordance with 
good agricultural practices. 3M Corporation 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 C8, C10, 
and C12 straight-chain fatty acid monoesters of glycerol and propylene 
glycol.

DATES: This regulation is effective June 23, 2004. Objections and 
requests for hearings, must be received on or before August 23, 2004.

ADDRESSES: To submit a written objection or hearing request follow the 
detailed instructions provided in Unit VIII. of the SUPPLEMENTARY 
INFORMATION. EPA has established a docket for this action under Docket 
ID number OPP-2003-0379. All documents in the docket are listed in the 
EDOCKET index at http://www.epa.gov/edocket. Although listed in the 

index, some information is not publicly available, i.e., confidential

[[Page 34938]]

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 either electronically in EDOCKET or in hard copy at the 
Public Information and Records Integrity Branch (PIRIB), Rm. 119, 
Crystal Mall 2, 1801 S. Bell St., Arlington, VA. This docket 
facility is open from 8:30 a.m. to 4 p.m., Monday through Friday, 
excluding legal holidays. The docket telephone number is (703) 305-
5805.

FOR FURTHER INFORMATION CONTACT: Carol E. Frazer, Biopesticides and 
Pollution Prevention Division (7511C), Environmental Protection Agency, 
1200 Pennsylvania Ave., NW., Washington, DC 20460-0001; telephone 
number: (703) 308-8810; e-mail address: frazer.carol@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 111), e.g., farmer.
     Animal production (NAICS 112), e.g., rancher.
     Food manufacturing (NAICS 311), e.g., restaurant.
     Pesticide manufacturing (NAICS 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 and Other 
Related Information?

    In addition to using EDOCKET (http://www.epa.gov/edocket/), you may 

access this Federal Register document electronically through the EPA 
Internet under the ``Federal Register'' listings at http://www.epa.gov/fedrgstr/.
 A frequently updated electronic version of 40 CFR part 180 

is available at E-CFR Beta Site Two at http://www.gpoaccess.gov/ecfr/.


II. Background and Statutory Findings

    In the Federal Register of December 12, 2001 (66 FR 64251) (FRL-
6809-8), EPA issued a notice pursuant to section 408(d)(3) of the 
FFDCA, 21 U.S.C. 346a(d)(3), announcing the filing of a pesticide 
tolerance petition (PP 1F6314) by 3M Corporation, 3M Center, St. Paul, 
MN 55144-1000. This notice included a summary of the petition prepared 
by the petitioner 3M Corporation. There were no comments received in 
response to the notice of filing.
    The petition requested that 40 CFR part 180 be amended by 
establishing an exemption from the requirement of a tolerance for 
residues of C8, C10, and C12 straight-chain fatty acid monoesters of 
glycerol and propylene glycol.
    Section 408(c)(2)(A)(i) of the 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 the 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), 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), 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 the 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 the 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 fatty acid monoesters of glycerol and propylene glycol are six 
closely-related monoesters of C8, C10, and C12 straight-chain fatty 
acids. There are three glycerol monoesters (glycerol monocaprylate, 
glycerol monocaprate, and glycerol monolaurate), and three propylene 
glycol monoesters (propylene glycol monocaprylate, propylene glycol 
monocaprate, and propylene glycol monolaurate).
    In vertebrate organisms (including humans), glycerol fatty acid 
monoesters are formed naturally as part of the metabolism of 
triglycerides. They also occur naturally in vegetable oils (e.g., 
coconut and palm oils) and in saw palmetto leaves and berries. Glycerol 
fatty acid monoesters are, in addition, used as direct food additives. 
Propylene glycol fatty acid monoesters, also used as direct food 
additives, are naturally metabolized in vertebrate systems in an 
identical manner to the glycerol fatty acid monoesters.
    Toxicity studies supporting this tolerance exemption are referenced 
below. More detailed analyses of these studies can be found in the 
specific Agency review of the studies (Ref. 1). Additional information 
relevant to toxicity also has been published and is cited in Ref. 2.
    Acute toxicity studies were generated to support EPA registration 
of the C8, C10, and C12 straight-chain fatty acid monoesters of 
glycerol and propylene glycol as biochemical pesticides. In all 
studies, EPA limit doses were used, and the test compounds were found 
to be non-toxic at the limit dose, but all tests were not conducted on 
each of the six active ingredients. Instead, a full acute toxicity test 
battery (6 studies) was generated for the C8 propylene glycol monoester 
(propylene glycol monocaprylate) and for the C12 glycerol ester 
(glycerol monolaurate), thereby bounding the chemical structures of all 
six active ingredients. In addition, because all six active ingredients 
are known to be identical with respect to acute toxicity and 
metabolism, a 90-day

[[Page 34939]]

rat oral toxicity study was conducted on propylene glycol monocaprylate 
only. The registrant requested and was granted waivers from toxicity 
testing for the additional monoesters (Ref. 3), since the metabolism 
and toxicity of the active ingredients have been well-documented for 
many years in the scientific literature. This represented all six 
active ingredients.
    1. Acute oral toxicity for glycerol monolaurate (OPPTS Harmonized 
Guideline 870.1100; 152-10; MRID 45405505): Non-toxic. Fasted rats 
(three male and three female) received a single oral gavage of glycerol 
monolaurate formulated in corn oil and administered at a dose level of 
5,000 milligrams/kilogram of body weight (mg/kg bwt). All rats survived 
and gained weight throughout the study with the exception of one female 
with a slight weight loss on the final day. Piloerection and increased 
salivation were observed in all rats within minutes of dosing. Normal 
salivation resumed shortly after dosing and piloerection resolved by 
day 3 in males and day 4 in females. No abnormalities were revealed in 
any rats at the macroscopic examination at study termination on day 15. 
The acute oral lethal dose (LD)50 for rats was >5,000 mg/kg. 
Classification: Acceptable; Toxicity Category IV (Ref. 4).
    2. Acute oral toxicity for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.1100; 152-10; MRID 45428501): Non-toxic. 
Fasted rats (three males and three females) received a single oral 
gavage of propylene glycol monocaprylate administered at a dose of 
5,000 mg/kg bwt. All rats survived and gained weight throughout the 
study. Piloerection (all rats) and increased salivation (one female 
only) were evident within a few minutes of dosing, with piloerection 
persisting for the remainder of day 1. Piloerection was resolved by day 
2 in females and by day 4 in males. No abnormalities were revealed in 
any animal at the macroscopic examination at study termination on day 
15. The acute oral LD50 for rats was >5,000 mg/kg. 
Classification: Acceptable; Toxicity Category IV (Ref. 5).
    3. Acute dermal toxicity for glycerol monolaurate (OPPTS Harmonized 
Guideline 870.1200; 152-11; MRID 45428501): Non-toxic. Ten rats (five 
males and five females) received a single topical application of 
glycerol monolaurate formulated in corn oil and administered at a dose 
of 5,000 mg/kg bwt. All rats survived and had normal weight gains 
throughout the study, with the exception of two females with low or no 
weight gain during week 1. No clinical signs of reaction to treatment 
were observed in any animal throughout the study, and no macroscopic 
abnormalities were observed in any animal at study termination on day 
15. The acute dermal LD50 for rats was >5,000 mg/kg. 
Classification: Acceptable; Toxicity Category IV (Ref. 6).
    4. Acute dermal toxicity for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.1200; 152-11; MRID 45428503): Non-toxic. Ten 
rats (five males and five females) received a single topical 
application of propylene glycol monocaprylate at a dose of 5,000 mg/kg 
bwt. All rats survived and gained weight, with the exception of one 
female with a slight weight loss during week 2. No macroscopic 
abnormalities were observed in any animal at study termination on day 
15. The acute dermal LD50 for rats was >5,000 mg/kg. 
Classification: Acceptable; Toxicity Category IV (Ref. 7).
    5. Acute inhalation for glycerol monolaurate (OPPTS Harmonized 
Guideline 870.1300; 152-12; MRID 45405506): Harmless by inhalation. In 
all instances, the aerosol generator was blocked following the start of 
generation. The waxiness of glycerol monolaurate made it impossible to 
generate aerosols. Because respirable particles cannot be produced from 
such low-melting waxy materials, the test substance is considered 
harmless by the inhalation route of exposure under normal handling 
conditions. Classification: Acceptable; Toxicity Category IV (Ref. 8).
    6. Acute inhalation for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.1300; 152-12; MRID 45405507): Non-toxic. Ten 
rats (five males and five females) were exposed for 4 hours to a 
droplet aerosol generated from propylene glycol monocaprylate at a 
target concentration of 5 mg/liter (L). Another group (five males and 
five females), exposed to clean dry air only, were controls. The mass 
median aerodynamic (MMAD) was 2.0 microns and was within the ideal 
range (1 micron to 4 microns) for an acute inhalation study. 
Approximately 88% of the particles were considered a respirable size 
(less than 7 microns in aerodynamic diameter). The lethal concentration 
(LC)5O (4-hour inhalation) for propylene glycol 
monocaprylate was >4.92 mg/L (4,920 ppm) in air. EPA's limit dose for 
this test is 2 mg/L. Classification: Acceptable; Toxicity Category IV 
(Ref. 9).
    7. Eye irritation for glycerol monolaurate (OPPTS Harmonized 
Guideline 870.2400, 152-13, MRID 45405508): Slight irritant. Each of 
three rabbits was administered a single ocular dose of 0.1 milliliter 
(mL) (mean weight 60 mg) of glycerol monolaurate and observed for up to 
7 days after instillation. The instillation in one animal elicited a 
corneal lesion and iritis (both Grade 1) 48 hours post-dose. All 
rabbits exhibited transient conjunctival inflammation (up to Grade 3). 
Resolution was complete in two instances within approximately 72 hours 
of dosing and, in one animal, 7 days after dosing. Glycerol monolaurate 
is considered a slight eye irritant. Classification: Acceptable; 
Toxicity Category III (Ref. 10).
    8. Eye irritation for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.2400, 152-13, MRID 45405509): Slight irritant. 
Three rabbits were each administered a single ocular dose of 0.1 mL of 
propylene glycol monocaprylate and observed for up to 7 days after 
instillation. The test substance elicited a transient, slight to well-
defined conjunctival irritation in two rabbits. Propylene glycol 
monocaprylate is not considered a major ocular irritant. 
Classification: Acceptable; Toxicity Category III (Ref. 11).
    9. Skin irritation for glycerol monolaurate (OPPTS Harmonized 
Guideline 870.2500, 152-14, MRID 45405510): Non-Irritant. Each of three 
rabbits was administered a single dermal dose of 0.5 g of glycerol 
monolaurate under semi-occlusive conditions for 4 hours and observed 
for up to 7 days. The test material produced transient slight erythema 
in 2 animals that resolved by 72 hours; the third animal had well-
defined erythema at 48 hours that resolved by day 7. Glycerol 
monolaurate is not considered a dermal irritant. Classification: 
Acceptable; Toxicity Category IV (Ref. 12).
    10. Skin irritation for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.2500, 152-14, MRID 45405511): Non-irritant. 
Each of three rabbits was administered a single dermal dose of 0.5 mL 
of propylene glycol monocaprylate under semi-occlusive conditions for 4 
hours and observed for up to 11 days. The test substance produced only 
slight erythema in all animals. Propylene glycol monocaprylate is not 
considered a dermal irritant. Classification: Acceptable; Toxicity 
Category IV (Ref. 13).
    11. Skin sensitization for glycerol monolaurate (OPPTS Harmonized 
Guideline 870.2600, 152-15, MRID 45428504): Non-sensitizer. Guinea pigs 
(10 test and 5 control) were dosed by intradermal injection and topical

[[Page 34940]]

application. Based on the results of a preliminary study, and in 
compliance with regulatory guidelines, the following dose levels were 
selected:
    Intradermal injection: 2.5% w/v (weight/volume) in sterile water.
    Topical application: 10% w/v in sterile water.
    Challenge applications: 0.5% and 1% w/v in sterile water.
Following the first challenge application, negative responses were 
observed in six test animals, inconclusive responses in three animals 
and a positive response was observed in the remaining test animal. A 
second challenge was conducted to clarify these reactions. Following 
the second challenge application, glycerol monolaurate did not produce 
dermal reactions in any test or control animal. Glycerol monolaurate is 
not thought to cause skin sensitization. The sensitivity of the guinea 
pig strain used by the laboratory is checked periodically with a weak/
moderate sensitizer - hexyl cinnamic aldehyde (HCA). In this study, HCA 
produced evidence of skin sensitization (delayed contact 
hypersensitivity) in 9 of the 10 animals, thus confirming the 
sensitivity and reliability of the experimental technique. 
Classification: Acceptable. (Ref. 14)
    12. Skin sensitization for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.2600, 152-15, MRID 45448201): Potential 
sensitizer. The guinea pigs (10 test and 5 control) were dosed by 
intradermal injection and topical application. Based on the results of 
a preliminary study and in compliance with the regulatory guidelines, 
the following dose levels were selected:
    Intradermal injection: 0.5% v/v in sterile water.
    Topical application: as supplied.
    Challenge application: 25% and 50% v/v in sterile water.
In this study, propylene glycol monocaprylate produced evidence of skin 
sensitization (delayed contact hypersensitivity) in all of the test 
animals. Propylene glycol monocaprylate may cause skin sensitization in 
humans. Propylene glycol itself is known to cause allergic reactions in 
patients receiving medical treatments containing this substance. The 
sensitivity of the guinea pig strain used is checked periodically by 
the laboratory with a weak to moderate sensitizer-HCA. In this study, 
HCA produced evidence of skin sensitization (delayed contact 
hypersensitivity) in 9 of the 10 animals, thus confirming the 
sensitivity and reliability of the experimental technique. This risk, 
however, is mitigated as long as the products are used according to the 
precautionary statements on the label, which advise washing thoroughly 
with soap and water after handling and that prolonged or frequently 
repeated skin contact may cause allergic reactions in some individuals. 
Classification: Acceptable (Ref. 15).
    13. 28-Day oral for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.3050, MRID 45441101): Non-toxic. The effects 
of propylene glycol monocaprylate (T-7475.8) were assessed in rats 
(groups of five males and five females) by oral gavage administration 
once a day for 4 weeks, employing dose levels of 0, 500, 750, or 1,000 
mg/kg/day. Doses up to 1,000 mg/kg/day were well tolerated with the 
only effects noted being higher protein and albumin values and a higher 
lung and liver weight, all in females. In the absence of 
histopathological examination, the toxicological importance of these 
findings is unclear. However, it was considered that 1,000 mg/kg/day 
was well tolerated and that it would be suitable for use as a high dose 
level in the subsequent 13-week toxicity study. Classification: 
Acceptable (Ref. 16).
    14. 13-Week oral for propylene glycol monocaprylate (OPPTS 
Harmonized Guideline 870.3100 and 870.7800, MRID 45428505): Non-toxic. 
The systemic toxicity of propylene glycol monocaprylate (T-7475.8) was 
assessed in groups of rats (20 males and 20 females per group) by oral 
gavage administration at 0, 100, 500, or 1,000 mg/kg/day dose levels 
for 13 weeks. There were no unscheduled deaths in any of the groups and 
clinical observation, neurotoxicity, metabolic parameters, and organ 
histopathology indicated no changes of toxicological significance. It 
was concluded that a dosage of 1,000 mg/kg/day was considered to be a 
no observable adverse effect level (NOAEL) for either sex. 
Classification: Acceptable (Ref. 17).
    15. Genotoxicity. Fatty acid monoesters of glycerol and propylene 
glycol in vertebrate systems are immediately metabolized to polyols and 
free fatty acids. Upon ingestion these compounds become 
indistinguishable from those in living systems. Polyols and free fatty 
acids in living systems are not genotoxic. Hence, waivers were 
requested and granted for all genotoxicity testing requirements on the 
basis that conducting such tests would not be of value to EPA in its 
evaluation of risks. The fatty acid monoesters of glycerol and 
propylene glycol are already known not to be genotoxic from a metabolic 
standpoint.
    16. Reproductive and developmental toxicity. On their metabolic 
basis, fatty acid monoesters of glycerol and propylene glycol and their 
natural breakdown products are known not to be reproductive or 
developmental toxicants. Waivers therefore were requested and granted 
for all such testing requirements on the basis that conducting such 
tests would not be of value to EPA in its evaluation of risks (for both 
the registration action and this tolerance exemption action).
    17. Scientific literature on toxicity and metabolism. Basic 
toxicity testing on mono- and diacylglycerols and saturated fatty acids 
was conducted in the 1930-1960 period and included intermediate-term 
and long-term studies. Less work has been published on propylene glycol 
saturated fatty acid esters, but the available data are adequate to 
demonstrate equivalence between propylene glycol esters and 
acylglycerols. Comprehensive reviews of these chemicals prepared by a 
number of sources including the Food and Drug Administration (FDA) and 
the Food and Agricultural Organization of the United Nations (FAO) and 
the World Health Organization (WHO) are available through the Joint 
FAO/WHO Expert Committee on Food Additives (JECFA). The no observed 
adverse effect levels (NOAELs) for monoacylglycerols, regardless of the 
saturated fatty acid, are similar. Rats can be fed from 10-15% in the 
diet for a lifetime without ill effects, dose levels corresponding to 5 
g/kg bwt/day. Rats fed propylene glycol monosuccinate and monostearate 
at levels up to 10% of the diet for 6 months showed no evidence of 
gross or histological pathology attributable to treatment. Dogs fed at 
the same levels for 6 months showed no signs of toxicity.
    The fatty acid moiety in monoacylglycerols is of no consequence 
because vertebrate systems are capable of metabolizing each of the 
acids in the range of C8 to C18 with equal facility. In fact, oxidation 
of fatty acids is a primary source of energy in vertebrate systems. 
Fatty acids are supplied in the diet in the form of triacylglycerols 
(fats) which are hydrolyzed by pancreatic lipase enzymes to form free 
fatty acids, glycerol and monoacylglycerols. The glycerol monoester 
active ingredients are indistinguishable from the natural acylglycerols 
and fatty acids found in the intestine following ingestion of fats. 
Specificity of the pancreatic lipase enzyme is independent of the 
nature of the fatty acid. It is also not stereospecific in its action 
and glycerol esters and propylene glycol esters are hydrolyzed by it 
with equal facility.

[[Page 34941]]

Studies with 14C-labeled propylene glycol show that it is readily 
absorbed from the gastrointestinal tract and rapidly converted in the 
liver to 14C-glycogen or 14CO2. Similarly, when 14C-glycerol is 
administered to rats, radiolabel appears in expired CO2, blood glucose, 
liver glycogen, liver fat and liver phosphatides within 15 minutes. 
Within 6 hours, 40% of the label is contained in expired CO2 and the 
remainder is distributed through the test animal. Very small amounts 
are excreted.
    FDA has looked at metabolism of propylene glycol mono- and 
distearates as model compounds to represent propylene glycol fatty 
acids. In studies on radiolabeled propylene glycol distearate the rate-
limiting factor in the metabolism was found to be hydrolysis of the 
ester, which is complete in about 3 hours. In 5 hours, 94% of the 
propylene glycol is absorbed and 94% of the absorbed material is found 
in expired CO2 in 72 hours. The fatty acid portion of the ester is 
absorbed and metabolized more slowly than the propylene glycol. Only 
51% of the stearic acid label was expired as CO2 in the same period.
    In addition, there is a long history of consumption by humans of 
fatty acids and their monoesters in food and the Agency knows of no 
instance where these have been associated with any toxic effects 
related to the consumption of food. Due to this knowledge of fatty acid 
monoesters' presence and function in the human system (Ref. 2) and the 
recent acute testing, EPA believes the fatty acid monoesters are 
unlikely to be carcinogenic or have other long-term toxic effects.
    The data from the toxicity studies (Ref. 1) and the additional 
information from the scientific literature submitted by the registrant 
(Ref. 2) are sufficient to support the current waiver requests, and to 
demonstrate that no substantial risks to human health are expected from 
the use of glycerol or propylene glycol fatty acid monoesters, when 
used in accordance with good agricultural practices and in accordance 
with all relevant labeling.

IV. Aggregate Exposures

    In examining aggregate exposure, section 408 of the 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).

A. Dietary Exposure

    Aggregate dietary exposure estimates were generated using EPA's 
Dietary Exposure Potential Model (DEPM) customarily used by the agency. 
The model is designed to generate dietary exposure estimates by 
combining food consumption and residue data. In this case, food 
consumption data came from the 10th National Food 
Consumption Survey conducted during the 3-year period of 1994-1996 by 
the Agricultural Research Service of the U.S. Department of 
Agriculture. These data are also known as the Continuing Survey of Food 
Intake by Individuals, 1994-1996 (CSFII 1994-1996).
    1. Food. Food residue estimates were generated for use in the DEPM 
analysis to simulate broad use of the fatty acid monoesters of glycerol 
and propylene glycol. Specifically, residue estimates were constructed 
for all food commodities corresponding to 18 raw agricultural 
commodities (RACs) for which residue data were generated for the 
following major food groups: Fruits; vegetables; beverages; and infant 
food. In keeping with the worst case nature of the analysis, residue 
data for a tested commodity was used also for similar commodities not 
tested (e.g., spinach values were used for other delicate greens; kale 
values were used for other heavy greens such as collard; peach values 
were used for apricots). It was also assumed residue levels are not 
changed by cooking and that fruit and vegetable mixtures contain 50% of 
one or more RAC, unless the composition of the mixture is specified. 
Total dietary exposure estimates were generated using the model for the 
U.S. population and 20 subpopulations, including non-nursing infants 
and children. The subpopulation groups were defined by age, gender, 
geographic location, ethnicity and income level. All calculations 
represented residue levels assuming treatment of 100% of every 
commodity consumed in the U.S. for which residue estimates could be 
generated, another severe worst-case assumption. The model produced 
data tables containing the consumption of each food, its assumed 
residue level and the calculated exposure from that consumption in 
[mu]g/kg-bwt/day for each of the subpopulations. For all subpopulation 
groups, the commodity that contributed in the analysis the most to 
exposure was cooked green beans. This result reflects the fact that 
green beans absorbed an unexpectedly large amount of treatment solution 
in the experimental procedure used to generate RAC residue estimates. 
Based upon the worst-case data and assumptions described above, the 
model calculated the highest exposure of 0.5 mg/kg bwt/day for non-
nursing infants. Dietary exposure for the total U.S. population was 
less than 0.2 mg/kg bwt/day. These levels are below the FDA approved 
dosage for addition to prepared foods, and the highest dose accepted as 
a chronic NOAEL for either sex was 5,000 times higher (Ref. 17).
    2. Drinking water exposure. All anticipated or proposed uses of 
glycerol and propylene glycol fatty acid monoesters will be indoors and 
the compounds are not soluble in water. Hence, drinking water is not a 
feasible route of exposure.

B. Other Non-Occupational Exposure

    Glycerol fatty acid monoesters are natural components of dietary 
fats and natural breakdown products from metabolism of fat 
(triacylglycerol) in all living systems. Additionally, fatty acid 
esters of both glycerol and propylene glycol occur as direct food 
additives.
    1. Dermal exposure. Results of the acute dermal toxicity studies 
for glycerol monolaurate and propylene glycol monocaprylate indicated 
no toxicity (Toxicity Category IV) at the maximum dose tested (5,000 
mg/kg) with no significant dermal irritation (Toxicity Category IV). 
Based on these results, the anticipated risks from dermal exposure are 
minimal. Dermal sensitization may occur with the propylene glycol 
monoesters as the caprylate is a potential sensitizer. This risk, 
however, is mitigated as long as the products are used according to the 
precautionary statements on the label, which advise washing thoroughly 
with soap and water after handling and that prolonged or frequently 
repeated skin contact may cause allergic reactions in some individuals.
    2. Inhalation exposure. Because the inhalation toxicity study for 
propylene glycol monocaprylate showed no toxicity (Toxicity Category 
IV), and the glycerol fatty acid monoesters are waxy solids at room 
temperature (not present as respirable particles), the risks 
anticipated for this route of exposure are minimal.

V. Cumulative Effects

    Section 408(b)(2)(D)(v) of FFDCA requires the Agency, when 
considering whether to establish, modify, or revoke a tolerance, to 
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.

[[Page 34942]]

    In assessing their cumulative effects, the fatty acid monoesters of 
glycerol and propylene glycol are members of a much larger class of 
compounds that are toxicologically and metabolically equivalent. All 
vertebrate systems deal with this class of compounds as food rather 
than toxicants. Glycerol fatty acid monoesters are natural components 
in dietary fats and natural breakdown products from metabolism of fat 
(triacylglycerol) in all living systems. Fatty acid esters of propylene 
glycol also occur as direct food additives in the human diet in 
substantial quantities. The use of fatty acid monoesters of glycerol 
and propylene glycol as pesticides will contribute a negligible amount 
(total U.S. population worst case estimate less than 0.2 mg/kg/day) to 
the existing cumulative exposure to the class of compounds when 
compared to natural levels of such compounds and their metabolites in 
tissue and foods (50-100 g/day in humans for glycerol esters), and to 
the levels permitted in food as direct additives (grams per day). 
Accordingly, exposure to these monoesters as a result of their label 
directed use as pesticides on raw agricultural food or feed commodities 
will result in a negligible increase in the cumulative exposure to this 
class of compounds over the present exposure, occurring as a result of 
daily consumption by the human population of this class of compounds 
from both naturally occurring sources and processed foods.

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

    1. U.S. population. It is doubtful harm will result from aggregate 
exposure to residues of the fatty acid monoesters of glycerol or 
propylene glycol in the U.S. population. This includes all anticipated 
dietary exposures and all other exposures for which there is reliable 
information. The Agency has arrived at this conclusion based on the 
very low levels of mammalian toxicity (no toxicity at the maximum doses 
tested, Toxicity Category IV) associated with the fatty acid monoesters 
of glycerol and propylene glycol and the long history of their 
consumption.
    2. Infants and children. FFDCA section 408 provides that EPA shall 
apply an additional tenfold margin of exposure (safety) for infants and 
children in the case of threshold effects to account for prenatal and 
postnatal toxicity and the completeness of the data base unless EPA 
determines a different margin of exposure will be safe for infants and 
children. Margins of exposure (safety) are often referred to as 
uncertainty factors. The registrant used the NOAEL of 1,000 mg/kg bwt/
day determined in the 90-day oral toxicity study in rats to calculate 
an estimated exposure of the active ingredients to the U.S. population 
of 0.13 mg/kg bwt/day and to non-nursing infants of 0.44 mg/kg bwt/day. 
The corresponding margins of exposure were calculated to be 7,690 for 
the U.S. population and 2,270 for non-nursing infants (Ref. 2).
    In this instance, based on all the available information, the 
Agency concludes that the C8, C10, and C12 monoesters of glycerol and 
propylene glycol are virtually non-toxic to mammals, including infants 
and children. Further, the provisions of consumption patterns, special 
susceptibility, and cumulative effects do not apply. Since no toxic 
endpoints have been identified, any hazard is impossible to determine. 
As a result, EPA has not used a margin of exposure approach to assess 
the safety of the C8, C10, and C12 monoesters of glycerol and propylene 
glycol. Based on their abundance in nature and long history of use by 
humans without deleterious effects, there is reasonable certainty that 
no harm will result from aggregate exposure to the U.S. population, 
including infants and children, to residues of these glycerol and 
propylene glycol straight-chain fatty acid monoesters. This includes 
all anticipated dietary exposures and all other exposures for which 
there are reliable information. Thus, the Agency has determined that 
the additional margin of safety is not necessary to protect infants and 
children and that not adding any additional margin of safety will be 
safe for infants and children.

VII. Other Considerations

A. Endocrine Disruptors

    EPA is required under the FFDCA, as amended by FQPA, to develop a 
screening program to determine whether certain substances (including 
all pesticide active and other ingredients) may have an effect in 
humans that is similar to an effect produced by a naturally-occurring 
estrogen, or other such endocrine effects as the Administrator may 
designate. Following the recommendations of its Endocrine Disruptor 
Screening and Testing Advisory Committee (EDSTAC), EPA determined that 
there was scientific basis for including, as part of the program, the 
androgen- and thyroid hormone systems, in addition to the estrogen 
hormone system. EPA also adopted EDSTAC's recommendation that the 
Program include evaluations of potential effects in wildlife. For 
pesticide chemicals, EPA will use FIFRA and, to the extent that effects 
in wildlife may help determine whether a substance may have an effect 
in humans, FFDCA authority to require the wildlife evaluations. As the 
science develops and resources allow, screening of additional hormone 
systems may be added to the Endocrine Disruptor Screening Program 
(EDSP).
    Based on the weight of the evidence of available data, no endocrine 
system-related effects are identified for the C8, C10, or C12 fatty 
acid monoesters of glycerol or propylene glycol and none is expected 
since they are natural components of vertebrate systems. Thus, there is 
no impact via endocrine-related effects on the Agency's safety finding 
set forth in this Final Rule for C8, C10, or C12 fatty acid monoesters 
of glycerol or propylene glycol.

B. Analytical Method(s)

    The Agency proposes to establish an exemption from the requirement 
of a tolerance for the C8, C10, and C12 straight-chain fatty acid 
monoesters of glycerol and propylene glycol without any numerical 
limitation, based on their lack of mammalian toxicity. Their use will 
create only minuscule exposures (< 1 mg/kg bwt/day) when compared to the 
natural levels of such compounds in living tissue and in foods (50-100 
grams (g)/day), and compared to the levels permitted in food as direct 
additives (g/day). Based on this, the Agency has concluded that an 
analytical method is not required for enforcement purposes for the 
fatty acid monoesters of glycerol or propylene glycol.

C. Codex Maximum Residue Level

    There are no CODEX values for the C8, C10, and C12 straight-chain 
saturated fatty acid monoesters of glycerol or propylene glycol.

D. Conclusions

    Based on the toxicology data submitted and other information 
available to the Agency, there is reasonable certainty no harm will 
result to the U.S. population, including infants and children, from 
aggregate exposure of residues of the C8, C10, and C12 straight-chain 
fatty acid monoesters of glycerol or propylene glycol when the product 
is used in accordance with good agricultural practices and in 
accordance with all relevant labeling. This includes all anticipated 
dietary exposures and all other exposures about which there is reliable 
information. As a result, EPA is establishing an exemption from 
tolerance requirements pursuant to FFDCA 408(c) and (d) for residues of 
the C8, C10, and C12 straight-chain fatty acid monoesters of glycerol 
and

[[Page 34943]]

propylene glycol in or on all food commodities.

VIII. Objections and Hearing Requests

    Under section 408(g) of the FFDCA, as amended by the 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. Although the procedures in those 
regulations require some modification to reflect the amendments made to 
the FFDCA by the FQPA, EPA will continue to use those procedures, with 
appropriate adjustments, until the necessary modifications can be made. 
The new section 408(g) of the FFDCA provides essentially the same 
process for persons to ``object '' to a regulation for an exemption 
from the requirement of a tolerance issued by EPA under new section 
408(d) of the FFDCA, as was provided in the old sections 408 and 409 of 
the FFDCA. However, the period for filing objections is now 60 days, 
rather than 30 days.

A. What Do I Need to Do to File an Objection or Request a Hearing?

    You must file your objection or request a hearing on this 
regulation in accordance with the instructions provided in this unit 
and in 40 CFR part 178. To ensure proper receipt by EPA, you must 
identify docket ID number OPP-2003-0379 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 
23, 2004.
    1. Filing the request. Your objection must specify the specific 
provisions in the regulation that you object to, and the grounds for 
the objections (40 CFR 178.25). If a hearing is requested, the 
objections must include a statement of the factual issues(s) on which a 
hearing is requested, the requestor's contentions on such issues, and a 
summary of any evidence relied upon by the objector (40 CFR 178.27). 
Information submitted in connection with an objection or hearing 
request may be claimed confidential by marking any part or all of that 
information as CBI. Information so marked will not be disclosed except 
in accordance with procedures set forth in 40 CFR part 2. A copy of the 
information that does not contain CBI must be submitted for inclusion 
in the public record. Information not marked confidential may be 
disclosed publicly by EPA without prior notice.
    Mail your written request to: Office of the Hearing Clerk (1900C), 
Environmental Protection Agency, 1200 Pennsylvania Ave., NW., 
Washington, DC 20460-0001. You may also deliver your request to the 
Office of the Hearing Clerk in Rm. 104, Crystal Mall 2, 1801 
S. Bell St., Arlington, VA. The Office of the Hearing Clerk is open 
from 8 a.m. to 4 p.m., Monday through Friday, excluding legal holidays. 
The telephone number for the Office of the Hearing Clerk is (703) 603-
0061.
    2. Tolerance fee payment. If you file an objection or request a 
hearing, you must also pay the fee prescribed by 40 CFR 180.33(i) or 
request a waiver of that fee pursuant to 40 CFR 180.33(m). You must 
mail the fee to: EPA Headquarters Accounting Operations Branch, Office 
of Pesticide Programs, P.O. Box 360277M, Pittsburgh, PA 15251. Please 
identify the fee submission by labeling it ``Tolerance Petition Fees. 
''
    EPA is authorized to waive any fee requirement ``when in the 
judgement of the Administrator such a waiver or refund is equitable and 
not contrary to the purpose of this subsection.'' For additional 
information regarding the waiver of these fees, you may contact James 
Tompkins by phone at (703) 305-5697, by e-mail at tompkins.jim@epa.gov, 
or by mailing a request for information to Mr. Tompkins at Registration 
Division (7505C), Office of Pesticide Programs, Environmental 
Protection Agency, 1200 Pennsylvania Ave., NW., Washington, DC 20460-
0001.
    If you would like to request a waiver of the tolerance objection 
fees, you must mail your request for such a waiver to: James Hollins, 
Information Resources and Services Division (7502C), Office of 
Pesticide Programs, Environmental Protection Agency, 1200 Pennsylvania 
Ave., NW., Washington, DC 20460-0001.
    3. Copies for the Docket. In addition to filing an objection or 
hearing request with the Hearing Clerk as described in Unit VIII.A., 
you should also send a copy of your request to the PIRIB for its 
inclusion in the official record that is described in Unit I.B.1. Mail 
your copies, identified by docket ID number OPP-2004-0379, to: Public 
Information and Records Integrity Branch, Information Resources and 
Services Division (7502C), Office of Pesticide Programs, Environmental 
Protection Agency, 1200 Pennsylvania Ave., NW., Washington, DC 20460-
0001. In person or by courier, bring a copy to the location of the 
PIRIB described in Unit I.B.1. You may also send an electronic copy of 
your request via e-mail to: opp-docket@epa.gov. Please use an ASCII 
file format and avoid the use of special characters and any form of 
encryption. Copies of electronic objections and hearing requests will 
also be accepted on disks in WordPerfect 6.1/8.0 or ASCII file format. 
Do not include any CBI in your electronic copy. You may also submit an 
electronic copy of your request at many Federal Depository Libraries.

B. When Will the Agency Grant a Request for a Hearing?

    A request for a hearing will be granted if the Administrator 
determines that the material submitted shows the following: There is a 
genuine and substantial issue of fact; there is a reasonable 
possibility that available evidence identified by the requestor would, 
if established resolve one or more of such issues in favor of the 
requestor, taking into account uncontested claims or facts to the 
contrary; and resolution of the factual issues(s) in the manner sought 
by the requestor would be adequate to justify the action requested (40 
CFR 178.32).

IX. References

    1. USEPA. Science Review in Support of the Registration of the 
Technical Grade Active Ingredient (TGAI) Product, VMX-42 Technology 
Propylene Glycol Monocaprylate, memo from Jones, Russell S., Ph.D., to 
Carol E. Frazer, Ph.D., April 4, 2003.
    2. Dubeck, J.B., S.M. Price, and A.P. Jovanovich. Petition 
Proposing an Exemption from Tolerance for Pesticide Residues in or on 
Raw Agricultural Commodities and Processed Food. 3M, St. Paul, MN. 
April 13, 2001.
    3. Jovanovich, A.P., Ph.D., MBA. Application for Pesticide 
Registration VWX-42 Technology. Request for Waivers. May 2, 2001.
    4. Blanchard, Emma L., B.Sc. (Hons.). Acute oral toxicity study. 
MRID 45405505.
    5. Coleman, David G., B.Sc. (Hons.). Acute oral toxicity study. 
MRID 45428501.
    6. Coleman, David G., B.Sc. (Hons.). Acute dermal toxicity study. 
MRID 45428502.
    7. Coleman, David G., B.Sc. (Hons.). Acute dermal toxicity study. 
MRID 45428503.
    8. Paul, Graham R., B.Sc. (Hons.), M.Sc. Biol., M.I. Biol. Acute 
inhalation toxicity study. MRID 45405506.
    9. Paul, Graham R., B.Sc. (Hons.), M.Sc. Biol., M.I. Biol. Acute 
inhalation toxicity study. MRID 45405507.
    10. Blanchard, Emma L., B.Sc. (Hons.). Primary eye irritation 
study. MRID 45405508.
    11. Blanchard, Emma L., B.Sc. (Hons.). Primary eye irritation 
study. MRID 45405509.
    12. Blanchard, Emma L., B.Sc. (Hons.). Primary dermal irritation 
study. MRID 45405510.

[[Page 34944]]

    13. Blanchard, Emma L., B.Sc. (Hons.). Primary dermal irritation 
study. MRID 45405511.
    14. Coleman, David G., B.Sc. (Hons.). Dermal sensitization study. 
MRID 45428504.
    15. Coleman, David G., B.Sc. (Hons.). Dermal Sensitization study. 
MRID 45448201.
    16. Bottomley, Sarah M., B.Sc. (Hons.), M.Sc., C.Biol., M.I.Biol. 
28-Day oral toxicity study in rats. MRID 45441101.
    17. Bottomley, Sarah M., B.Sc. (Hons.), M.Sc., C.Biol., M.I.Biol. 
90-Day oral toxicity study in rats. MRID 45428505.

X. Statutory and Executive Order Reviews

    This final rule establishes an exemption from the tolerance 
requirement under section 408(d) of the 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 rule has been exempted from review under Executive 
Order 12866 due to its lack of significance, this 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). 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., or 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). 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); 
or OMB review or any Agency action under Executive Order 13045, 
entitled Protection of Children from Environmental Health Risks and 
Safety Risks (62 FR 19885, April 23, 1997). 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). Since 
tolerances and exemptions that are established on the basis of a 
petition under section 408(d) of the FFDCA, such as the exemption in 
this final rule, do not require the issuance of a proposed rule, the 
requirements of the Regulatory Flexibility Act (RFA) (5 U.S.C. 601 et 
seq.) do not apply. In addition, the Agency has determined that this 
action will not have a substantial direct effect on States, on the 
relationship between the national government and the States, or on the 
distribution of power and responsibilities among the various levels of 
government, as specified in Executive Order 13132, entitled Federalism 
(64 FR 43255, August 10, 1999). Executive Order 13132 requires EPA to 
develop an accountable process to ensure ``meaningful and timely input 
by State and local officials in the development of regulatory policies 
that have federalism implications.'' ``Policies that have federalism 
implications '' is defined in the Executive Order to include 
regulations that have ``substantial direct effects on the States, on 
the relationship between the national government and the States, or on 
the distribution of power and responsibilities among the various levels 
of government.'' This final rule directly regulates growers, food 
processors, food handlers and food retailers, not States. This action 
does not alter the relationships or distribution of power and 
responsibilities established by Congress in the preemption provisions 
of section 408(n)(4) of the FFDCA. For these same reasons, the Agency 
has determined that this rule does not have any ``tribal implications'' 
as described in Executive Order 13175, entitled Consultation and 
Coordination with Indian Tribal Governments (65 FR 67249, November 6, 
2000). Executive Order 13175, requires EPA to develop an accountable 
process to ensure ``meaningful and timely input by tribal officials in 
the development of regulatory policies that have tribal implications.'' 
``Policies that have tribal implications'' is defined in the Executive 
Order to include regulations that have ``substantial direct effects on 
one or more Indian tribes, on the relationship between the Federal 
Government and the Indian tribes, or on the distribution of power and 
responsibilities between the Federal Government and Indian tribes.'' 
This rule will not have substantial direct effects on tribal 
governments, on the relationship between the Federal Government and 
Indian tribes, or on the distribution of power and responsibilities 
between the Federal Government and Indian tribes, as specified in 
Executive Order 13175. Thus, Executive Order 13175 does not apply to 
this rule.

XI. Congressional Review Act

    The Congressional Review Act, 5 U.S.C. 801 et seq., as added by the 
Small Business Regulatory Enforcement Fairness Act of 1996, generally 
provides that before a rule may take effect, the agency promulgating 
the rule must submit a rule report, which includes a copy of the rule, 
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: June 10, 2004.
James Jones,
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 180.1250 is added to subpart D to read as follows:


Sec.  180.1250  C8, C10, and C12 fatty acid monoesters of glycerol and 
propylene glycol; exemption from the requirement of a tolerance.

    The C8, C10, and C12 straight-chain fatty acid monoesters of 
glycerol (glycerol monocaprylate, glycerol monocaprate, and glycerol 
monolaurate) and propylene glycol (propylene glycol monocaprylate, 
propylene glycol monocaprate, and propylene glycol monolaurate) are 
exempt from the requirement of a tolerance in or on all food 
commodities when used in accordance with approved label rates and good 
agricultural practice.

[FR Doc. 04-14222 Filed 6-22-04; 8:45 am]

BILLING CODE 6560-50-S