United States
Environmental Protection
Agency.
Prevention, Pesticides
And Toxic Substances
(7508W)
EPA-738-F-96-021
October 1996
R.E.D. FACTS
TridecenyI Acetates
Pesticide All pesticides sold or distributed in the United States must be
Reregistration registered by EPA, based on scientific studies showing that they can be
used without posing unreasonable risks to people or the environment.
Because of advances in scientific knowledge, the law requires that
pesticides which were first registered before November 1,1984, be
reregistered to ensure that they meet today's more stringent standards.
In evaluating pesticides for reregistration, EPA obtains and reviews a
complete set of studies from pesticide producers, describing the human
health and environmental effects of each pesticide. The Agency develops
any mitigation measures or regulatory controls needed to effectively reduce
each pesticide's risks. EPA then reregisters pesticides that can be used
...-.. without posing unreasonable risks to human health or the environment
When a pesticide is eligible for reregistration, EPA explains the basis
for its decision in a Reregistration Eligibility Decision (RED) document.
This fact sheet summarizes the information in the RED document for
reregistration case 4116, tridecenyl acetates.
Use Profile
Regulatory
History
Tridecenyl acetates are sex attractant pheromones used in tomato
Jields to disrupt the mating behavior of tomato pinworms.
Formulations include the technical grade active ingredients (TGAI)
and inert ingredients inside a solid polymeric matrix known as a dispenser;
the TGAI encapsulated in beads; and the TGAI embedded into polymeric
fibers.
Tridecenyl acetate products are applied by spraying the beads or
fibers, or by distributing the solid matrix dispensers.
There are no use practice limitations. '';'
Tridecenyl acetates were first registered as a pesticide in the U.S. in
1982. Currently, eleven tridecenyl acetate products are registered with four
companies. These products employ the sex attractant pheromone of the
tomato pinworm and are applied to fields of tomatoes to disrupt the mating
behavior
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Human Health
Assessment
Toxicity
In studies using laboratory animals, tridecenyl acetates generally have
been shown to be of low acute toxicity. There is potential for dermal, eye
and inhalation exposures to the pesticide for pesticide handlers, but due to
low application rates, even lower exposure subsequent to application, and to
the fact that the TGAI is embedded in a polymeric matrix, the potential is
considered minimal. Tridecenyl acetates have been placed in Toxicity
Category IV (the lowest of four categories) for this effect.
[NOTE: For acute oral, dietary, mammalian/avian/aquatic toxicity:
Category I = very highly or highly toxic
Category n = moderately toxic
Category HI = slightly toxic
Category IV = practically non-toxic]
Dietary Exposure
This compound is not applied directly to the tomato plants nor is it
taken up or metabolized by tomato plants, but rather it is incorporated into
dispensers or as a microencapsulated material. Therefore, dietary exposure
to this compound is expected to be minimal. The Agency has established
an exemption from the requirements of a tolerance for this group of active
pesticidal ingredients (lepidopteran pheromones) when used at a rate not to
exceed 150 g. a.i./acre/year.
Occupational and Residential Exposure
Based on current use patterns, handlers (mixers, loaders, and
applicators) may be exposed to tridecenyl acetates during normal use of
bead, fiber and dispenser formulations. However the Agency believes that
the risk from this exposure is minimal.
Environmental
Assessment
Human Risk Assessment
Tridecenyl acetates generally are of low acute toxicity. Food crop use
is limited to tomatoes. Dietary exposure to tridecenyl acetate residues in
foods is extremely low.
Environmental Fate
Environmental fate Tier n studies for biochemicals are not imposed
unless adverse effects are observed in Tier I Environmental Expression
testing with wildlife, fish and aquatic invertebrates. There are no
outstanding environmental effects data requirements for the tridecenyl
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acetates. Sufficient data have been provided for an environmental fate and
effects assessment. Therefore--the Agency will not impose any
environmental fate requirements for reregislyation of the currently
registered products containing tridecenyl acetates,
Ecological Effects
All ;pf the ecological effects data requirements for tridecenyl acetates
have been adequately fulfilled. A review of all available ecological toxieity
data indicate that tridecenyl acetates are not likely to cause adverse effects
in non-target avian, fish and aquatic invertebrate species.
Additional Data
Required
Product Labeling
Changes
Required
Ecological Effects Risk Assessment
1 " - - J - . - - - ^ ' -.,,-,--._..'.._,,." , , "- ,' ,;..,;
Ecological risk is considered minimal and therefore there are no risk
mitigation measures required.
EPA is not requiring additional generic studies for tridecenyl acetates
at this time but will require revised Confidential Statements of Formula,
(CSFs), and revised labeling for reregistration.
Labeling Requirements for Manufacturing-Use Products
There are currently three manufacturing-use products registered.
These are the 3M Company's MEC Tomato Pinworm Pheromone
Concentrate (10350-34), Bedoukian'sTPW Technical Pheromone (52991-,
3) and Consep's Checkmate TPW Technical Pheromone (56336-7). To be
in compliance with FIFRA, manufacturing use product labeling must
comply with all current EPA regulations, PR Notices and applicable
policies. The MP labeling must bear the following statement under
Directions for Use:...
"Only for formulation into a pheromone for the following use: as an
attractant in a mating disrupter."
An MP registrant may, at his/her discretion, add one of the following
statements to an MP label under "Directions for Use" to permit the
reformulation of the product for a specific use or all additional uses,
supported by a fbrmulator or user group: ,
-*.' ' ,'..-'.-. ' ' - :, _ . L. ... \ ,
(a) "This product may be used to formulate products for specific use(s)
not listed on the MP label if the formulator, user group, or grower has
complied with U.S. EPA submission requirements regarding support
of suchuse(s)." _ .
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(b) "This product may be used to formulate products for any additional
use(s) not listed on the MP label if the formulator, user group, or
grower has complied with U. S. EPA submission requirements
regarding support of such use(s)."
f
End-Use Products:
All tridecenyl acetate end-use products must comply with EPA's
current pesticide product labeling requirements. For a comprehensive list
of labeling requirements, please see the tridecenyl acetates RED document
Worker Protection Standard:
The labeling of all microencapsulated end-use products containing
tridecenyl acetate must comply with EPA's current regulations and
requirements as specified in 40 CFR 156.10 and other applicable notices.
According to Pesticide Regulation (PR) Notice 93-7, "Labeling Revisions
Required by the Worker Protection Standard (WPS)", WPS does not apply
to attractants used in insect dispensers. However the microencapsulated
products are within the scope of the WPS and must bear all of the labeling
requirements stipulated in PR Notices 93-7 and 93-11.
Environmental Hazard:
The following Environmental Hazard Statement must appear on the
labeling of all products containing tridecenyl acetates:
"Do not apply directly to water, or to areas where surface water is
present or to intertidal areas below the high-water mark. Do not
contaminate water when disposing of equipment wash water or
rinsate."
Regulatory The use of currently registered products containing tridecenyl acetates
Conclusion m accordance with approved labeling will not pose unreasonable risks or
adverse effects to humans or the environment. Therefore, all uses of these
products are eligible for reregistration.
Tridecenyl acetates products will be reregistered once the required
revised Confidential Statements of Formula, and revised product labeling
are received and accepted by EPA.
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For More EPA is requesting public comments on the Reregistration Eligibility
Information Decision (RED) document for tridecenyl acetates during a 60-day time
period., as announced in a Notice of Availability published in the Federal
Register. To obtain a copy of the RED document or to submit written
comments, please contact the Pesticide Docket, Public Response and
Program Resources Branch, Field Operations Division (7506C), Office of
Pesticide Programs (OPP), US EPA, Washington, DC 20460, telephone
, 703-305-5805.
Electronic copies of the RED and this fact sheet can be downloaded
from me Pesticide Special Review and Reregistration Information System
at 703-308-7224. They also are available on the Interneton EPA's gopher
server, GOPHER.EPA.GOV,or using ftp onFTP.EPA:GO7,orusmg
WWW (World Wide Web) On WWW.EPA.GOV.
Printed copies of the RED and fact sheet can be obtained from EPA's
National Center for Environmental Publications and Information , _.
(EPA/NCEPI), PO Box 42419, Cincinnati, OH 45242-0419, telephone
513-489-8190, fax 513-489-8695. " ..'.'
Following the comment period, the tridecenyl acetates RED document
also will be available from the National Technical Information Service
(NTIS), 5285 Port Royal Road, Springfield,'VA 22161, telephone 703-487-
.......' ' 4650. . _ . . ' .'; ; :. ' . \ "; ^ , '.. .'.' '^'/'
For more information about EPA's pesticide reregistration program,
the tridecenyl acetates RED, or reregistration of individual products
. containing tridecenyl acetates, please contact the Special Review and
, Reregistration Division (7508W), OPP, US EPA, Washington, DC 20460,
telephone 703-308-8000.
For information about the health effects of pesticides, or for assistance.
v in recognizing and managing pesticide poisoning symptoms, please contact
theNational Pesticides Telecommunications Network^(NPTN). Call 'toil-- -
. free 1-800-858-7378, between 9:30 am and 7:30 pm Eastern Standard
Time, Monday through Friday.
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1 *
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. . . , . , .
UNITED STATES ENVIRONMENTAL PROTECTION AGENCY
WASHINGTON, D.C. 20460
.- -' - . OFF1CEOF '' ' '
PREVENTION. PESTICIDES
AND TOXIC SUBSTANCES
CERTIFIED MAIL
Dear Registrant: - .'.',' -.--
I am pleased to announce that the Environmental Protection Agency has completed its
reregistration eligibility review and decisions on the pesticide chemical case tridecenyl
acetates which includes the active ingredients (E)^-tridecen-l-yl acetate arid (Z)-4-tridecen-
1-yl acetate. The enclosed Reregistration Eligibility Decision fRED^ contains the Agency's
evaluation of the data base of these chemicals, its conclusions of the potential human health
and environmental risks of the current product uses, and its decisions arid conditions under
which these uses and products will be eligible for reregistration. The RED includes the data
and labeling requirements for products for reregistration. It may also include requirements for
additional data (generic) on the active ingredients to confirm the risk assessments.
Please note that this RED was finalized and signed prior to August 3,1996. On that
date, the Food Quality Protection Act of 1996 ("FQPA") became effective, amending portions
of bbth the pesticide law (FJFRA) arid the food and drug law (FFDCA). This RED does not
address any issues raised by FQPA, and any tolerance-related statements in the RED did not
take into account any changes in tolerance assessment procedures required under FQPA. To
the extent that FQPA requires reassessments of any existing tolerances for the tridecenyl
acetates, me Agency will reassess those tolerances in the future pursuant to the new
requirements of FQPA.
To assist you with a proper response, read Hie enclosed document entitled "Summary
of Instructions for Responding to the RED." This summary also refers to, other enclosed
documents which include further instructions. You must follow all instructions and submit
complete and timely responses. The first set of required responses is due 90 days from the
receipt of this letter. The second set of required responses is due 8 months from the date
of this letter. Complete and timely ^responses will avoid the Agency taking the enforcement
action of suspension against ybuf products.;
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If you have questions about our decision or the requirements set forth in this
document, please contact the reregistration representative for the Biopesticides and Pollution
Prevention Division, Anne R. Leslie, 703-308-8727.
Sincerely yours,
Janet Andersen, Acting Director
Biopesticides and Pollution
Prevention Division (7501W)
Enclosures:
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SUMMARY OF INSTRUCTIONS FOR RESPONDING TO
THE REREGISTRATION ELIGIBILITY DECISION (REDTt
1. DATA CALL-IN (PCD OR "90-DAY RESPONSE"-If generic data are required for
reregistratipn, a DCI letter will be enclosed describing such data! If product specific data are
required, a DCI letter will be enclosed listing such requirements. If both generic and
product specific data are required, a combined Generic and Product Specific DCI letter will
be enclosed describing such data. However, if you are an end-use product registrant only and
have been granted a generic data exemption (GDE) by EPA, you are being sent only the
product specific response forms (2 forms) with the RED. Registrants responsible for generic
data are being sent response forms for both generic and product specific data requirements (4
forms). You must submit the appropriate response forms (following the instructions
provided) within 90 days of the receipt of this RED/DCI letter; otherwise, your product
may be suspended.
2. TIME EXTENSIONS AND DATA WAIVER REOUESTS-No time extension requests
will be granted for the 90-day response. Time extension requests may be submitted only with
respect to actual data submissions. Requests for time extensions for product specific data
should be submitted in the 90-day response. Requests for data waivers must be submitted as
part of the 90-day response. All data waiver and time extension requests must be
accompanied by a full justification. All waivers and time extensions must be granted by EPA
in order to go into effect.
,''.-" . ' " ' .; ^ " ."" . . .. '. ... .
3. APPLICATION FOR REREGISTRATION OR "8-MONTH RESPONSE"-You
must submit the following items for each product within eight months of the date of this
letter (RED issuance date).
a. Application for Reregistration (EPA Form 8570-1). Use only an original
application form. Mark it "Application for Reregistration." Send your Application for
Reregistration (along with the other forms listed in b-e below) to the address listed in item 5.
b: Five copies of draft labeling .which complies with the RED and current regulations
and requirements. Only make labeling changes which are required by the RED and current
regulations (40 CFR 156.10) and policies. Submit any other amendments (such as
formulation changes, or labeling changes not related to reregistration) separately. You may,
but are not required to, delete uses which the RED says are ineligible for reregistration. For
further labeling guidance, refer to the labeling section of the EPA publication "General
Information on Applying for Registration in the U.S., Second Edition. August 1992"
(available from the National Technical Information Service, publication #PB92-221811;
telephone number 703-487-4650).
c. Generic or Product Specific Data. Submit all data in a format which complies
with PR Notice 86-5, and/or submit citations of data already submitted and give the EPA
identifier (MRID) numbers. Before citing these studies, you must make sure that they meet
the Agency's acceptance criteria (attached to the DCI).
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d. Two conies of the Confidential Statement of Formula (CSF) for each basic and
each alternate formulation. The labeling and CSF which you submit for each product must
comply with P.R. Notice 91-2 by declaring the active ingredient as the nominal
concentration. You have two options for submitting a CSF: (1) accept the standard certified
limits (see 40 CFR ง158.175) or (2) provide certified limits that are supported by the analysis
of five batches. If you choose the second option, you must submit or cite the data for the five
batches along with a certification statement as described in 40 CFR ง158.175(e). A copy of
the CSF is enclosed; follow the instructions on its back.
e. Certification With Respect to Data Compensation Requirements. Complete
and sign EPA form 8570-31 for each product.
4. COMMENTS IN RESPONSE TO FEDERAL REGISTER NOTICE-Comments
pertaining to the content of the RED may be submitted to the address shown in the Federal
Register Notice which announces the availability of this RED.
5. WHERE TO SEND PRODUCT SPECIFIC PCI RESPONSES (90-DAY1 AND
APPLICATIONS FOR REREGISTRATION (8-MONTH RESPONSES)
BvTJ.S.Mail;
Document Processing Desk (RED-BPPD)
Office of Pesticide Programs (7504C)
EPA, 401 M St. S.W.
Washington, D.C. 20460-0001
Bv express; .
Document Processing Desk (RED-BPPD)
Office of Pesticide Programs (7504C)
Room 266A, Crystal Mall 2
1921 Jefferson Davis Hwy.
Arlington, VA 22202
6. EPA'S REVIEWSEPA will screen all submissions for completeness; those which are
not complete will be returned with a request for corrections. EPA will try to respond to data
waiver and time extension requests within 60 days. EPA will also try to respond to all 8-
month submissions with a final reregistration determination within 14 months after the RED
has been issued.
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REREGISTRATION ELIGIBILITY DECISION
TRIDECENYL ACETATES
.;. '. ;:-.;;..: -. LISTD ; ..
CASE4116 I'..'
ENVIRONMENTAL PROTECTION AGENCY
OFFICE OF PESTICIDE PROGRAMS
BIOPESTIODE AND POLLimON PREVENTION DIVISION
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TABLE OF CONTENTS
TRTOECENYL ACETATES REREGISTRATION ELIGIBILITY DECISION TEAM
.'.-',.. ..... ..'.:............ ..:.;'.-....:...-..... i
EXECUTIVE SUMMARY ..... .',.'.''. ..,..,.:.. . ..'. . v. ..,. .... /.".....i.. .,,'..,...,, .y
I. INTRODUCTION . . . ............. . .V....... . .. . .. 1
n. CASE OVERVIEW ........."... ..-;..'..,:.'................................".. .2
.- A. Chemical Overview ...:... .. ... ............... 2
B. Use Profile ........:.:...:....'-.'.-.. r..... ................;.... ,3
C. Estimated Usage of Pesticide 4
D. Regulatory History 4
HI. , SCIENCE ASSESSMENT...............-. 7..'.............. 5
A.. Product Chemistry Assessment .''....'.'... ... ........ 5,
B. Human Health Assessment 7
1. Toxicology Assessment *.............:.......?
-a. AcuteTpxicity. ;...;.;.......... 7
b. Mutagenicity ......................!....... ^...;.... 7
, c. SubchronicAssessment .....8
2. Exposure Assessment ........1............................. 8
'' a. Dietary Exposure 8
. b. Occupational and Residential Exposure 9
3. Human Risk Assessment ,.,.......'... ..>,............. .9
1 C. Environmental Assessment 10
1. Ecological Toxicity Data ,.......... 10
2. Environmental Fate ..................................... 11
IV. RISK MANAGEMENT AND REREGISTRATION DECISION ...:. .. . ..... 12
A. Determination of Eligibility .12
1. Eligibility Decision ... V...,...,,; ................ 12
.^2. Eligible and Ineligible Uses ..13
B. Regulatory Position .., .13
1. Tolerance Reassessment .......;...,......., .13
2. Endangered Species Statement ............................ 13
3o Labeling Rationale . ......... '..-.!.!..... . .. 13
V. ACTIONS REQUIRED OF REGISTRANTS ...:. .. . . .. ..-..". '. . . 14
A. Manufacturing-Use Products 14
1. Additional Generic Data Requirements .... 14
2. Labeling Requirements for Manufacturing-Use Products .14
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B. End-Use Products 15
1. Additional Product-Specific i .. Requirements 15
2. Labeling Requirements for EJ- Jse Products: 15
C. Existing Stocks 16
VT. APPENDICES .17
APPENDIX A. Table of Use Patterns Subject to Reregistration 1$
APPENDIX B. Table of the Generic Data Requirements and Studies Used to
Make the Reregistration Decision .25
APPENDIX C. Citations Considered to be Part of the Data Base Supporting
the Reregistration of Tridecenyl Acetates '.... 29
APPENDIX D. List of Available Related Documents 35
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TRIDECENYL ACETATES REREGISTRATION ELIGmiLITY DECISION.TEAM
Office of Pesticide Programs: r-
- -. .: . , .'.', . . . .j
Biopesticides and Pollution Prevention Division "'_.''>
J. Thomas McClintock
Freshteh Toghrol , ,
FrankEllis :-,-'. V
Anne Leslie
RichardKing
Biological and Economic Analysis Division
WilfbrdBurr
Frank Hernandez :
Dave Thomas
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11
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GLOSSARY OF TERMS AND ABBREVIATIONS
ADI Acceptable Daily Intake. A now defunct term for reference dose (RfD).
AE Acid Equivalent . '...*
a.i. Active Ingredient \ >.'-'
ARC Anticipated Residue Contribution . ,
CAS Chemical Abstracts Service
CI Cation , .'.......:
CNS Central Nervous System
CSF Confidential Statement of Formula
DFR j Dislodgeable Foliar Residue
DRES Dietary Risk Evaluation System ;
DWEL Drinking Water Equivalent Level (DWEL) the DWEL represents a medium specific (i.e.
drinking water) lifetime exposure at which adverse, non carcinogenic health effects are not
anticipated to occur. \ . '
EEC Estimated Environmental Concentration. The estimated pesticide concentration in an
environment, such as a terrestrial ecosystem. ; > ' ." -
EP, End-Use Product ' _ '.
EPA .U.S. Environmental Protection Agency
FAO/WHO, Food and Agriculture Organization/World Health Organization
FDA Food and Drag Administration
FIFRA Federal Insecticide, Fungicide, and Rodenticide Act :
FFDCA r. Federal Food, Drug, and Cosmetic Act
FOB .Functional Observation Battery . ' ;'
GLC ; Gas Liquid Chromatography
GM ' Geometric Mean -
GRAS Generally Recognized as Safe as Designated by FDA .-.."..
HA Health Advisory, (HA). The HA values are used as informal guidance to mumicipalities and ,
other organizations when emergency spills or contamination situations occur.
HDT.-...; -. Highest Dose Tested ^ ,
LCM Median Lethal Concentration. A statistically derived concentration of a substance that can be
expected to cause death in 50% of test animals. It is usually expressed as the weight of
substance per weight or volume of water, air or feed, e.g., mg/1, mg/kg or ppm. , .
LDSO, Median Lethal Dose. A statistically derived single dose that can be expected to cause death in
50% of me test ammals when administered by the route indicated (oral, deraaal, inhalation). It
is expressed as a weight of substance per unit weight of;animal, e.g., mg/kg.
LD,0 Lethal Dose-low. Lowest Dose at which lethality occurs.
LEL Lowest Effect Level
LOG Level of Concern , . . .
LOD Lunit of Detection
LOEL Lowest Observed Effect Level ' .
MATG Maximum Acceptable Toxicant Concentration
MCLG, Maximum Contaminant Level .Goal (MGLG) The MCLG is used by the Agency to regulate
contaminants in drinking water under the Safe Drinking Water Acป
fig/g Micrograms PerGram '
mg/L Milligrams Per Liter
MOE Margin of Exposure ' - ' , >
MP Manufacturing-Use Product , / ,-.. ' ,
MPI Maximum,Permissible Intake _ . ^ . ,
MRTD Master Record Identification (number). EPA's system of recording and tracking studies
submitted. ' , :. . -
N/A ... NotApplicable .,
1U-
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GLOSSARY OF TERMS AND ABBREVIATIONS
NOEC No effect concentration
NPDES National Pollutant Discharge Elimination System
NOEL No Observed Effect Level
NOAEL No Observed Adverse.Effect Level
OP Organophosphate
OPP Office of Pesticide Programs
PADI Provisional Acceptable Daily Intake ' ,
PAG Pesticide Assessment Guideline ,
PAM Pesticide Analytical Method
PHED Pesticide Handler's Exposure Data
PHI Preharvest Interval
ppb Parts Per Billion j.
PPE Personal Protective Equipment
ppm Parts Per Million
PRN Pesticide Registration Notice ,
Q*, The Carcinogenic Potential of a Compound, Quantified by the EPA's Cancer Risk Model
RBC Red Blood Cell
RED ; Reregistration Eligibility Decision
REI Restricted Entry Interval
RfD Reference Dose
RS Registration Standard
RUP Restricted Use Pesticide
SLN Special Local Need (Registrations Under Section 24ฉ of FIFRA)
TC Toxic Concentration. The concentration at which a substance produces a toxic effect.
TD Toxic Dose. The dose at which a substance produces a toxic effect
TEP Typical End-Use Product
TGAI Technical Grade Active Ingredient _
TLC Thin Layer Chromatography
TMRC Theoretical Maximum Residue Contribution
torr A unit of pressure needed to support a column of mercury 1 mm high under standard conditions.
ug/L Micrograms per liter
WP Wettable Powder
WPS Worker Protection Standard
IV
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EXECUTIVE SUMMARY .- :;., \,"'; ..,:' \'.. ,; ;.. ;,, . ; \".' ;: .-;.
The U. S. Environmental Protection Agency has completed its reregistration eligibility
decision of the pesticide tridecenyl acetates, which pertain to the active ingredients
(Z)-4-tridecen-l-yl acetate and (E)-4-tridecen-l-yl acetate. This decision includes a
comprehensive reassessment of the required data for the use patterns of currently registered
products. Tridecenyl acetates are sex attractant pheromones used in tomato fields to disrupt '
the mating behavior of tomato pinworms. .These pheromones, which mimic those released by
the female moths, attract the male moths to impregnated fibers, dispensers, or sprayable beads
rather than female moths, thereby reducing the likelihood of successful matings. This, in turn,
can reduce fertile, egg laying and subsequent larval infestations. The Agency has concluded
that all uses as described in this document^ will not cause unreasonable risks to humans or the
environment and therefore, all products are eligible for reregistration. The Agency is not
requiring any additional studies.
Before reregistering the products containing tridecenyl acetates, the Agency is
requiring that product-specific data, revised Confidential Statements of Formula (CSF) and
revised labeling be submitted within eight months of the issuance of this document. These
data include product chemistry for each registration. After reviewing these data and any
revised labels and finding them acceptable in accordance with Section 3 (c)(5) of FIFRA, the .
Agency will reregister a product Those products which contain other active ingredients will
be eligible for reregistration only when the other active ingredients are determined to be
eligible for reregistration.
v. ,
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I. INTRODUCTION
In 1988, the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) was
amended to accelerate the reregistration of products with active ingredients registered prior to
November 1, 19,84. The amended Act provides a schedule for the reregistration process to be
completed in nine years. There are five phases to the reregistration process. The first four
phases of the process focus oh identification of data requirements to support the reregistration
of an active ingredient and the generation and submission of data to fulfill.the requirements.
The fifth phase is a review by the U.S. Environmental Protection Agency (referred to as "the
Agency") of all data submitted to support reregistration. '
FIFRA Section 4(g)(2)(A) states that in Phase 5 "the Admimsti-ator shall determine
whether pesticides containing such active ingredient are eligible for reregistration" before
calling in data on products and either reregistering products or taking " other appropriate
regulatory action." Thus, reregistration involves a thorough review of the scientific data base
underlying a pesticide's registration. The purpose of the Agency's review is to reassess the
potential hazards arising from the currently registered uses of the pesticide; to determine the
need for additional data on health and environmental effects; and to determine whether the
pesticide meets the "no unreasonable adverse effects" criterion of FIFRA.
This document presents the Agency's decision regarding the reregistration eligibility of
the registered uses of tridecenyl acetates. The document consists of six sections. Section I is
the introduction. Section II describes tridecenyl acetate, its uses, data requirements and ,
regulatory history. Section HI discusses the human health and environmental assessment
based on the dataavailable to the Agency. Section IV presents the reregistration decision for
tridecenyl acetate. Section V discusses the reregistration requirements for tridecenyl acetate.
Finally, Section VI is the Appendices which support this Reregistration Eligibility Decision.
Additional details concerning the Agency's review of applicable data are available on request.
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H. CASE OVERVIEW
A. Chemical Overview
The following active ingredients are covered by this Reregistration Eligibility
Decision:
Common Name: Tridecenyl acetates .
Chemical Names: (E)-4-tridecen-l-yl acetate
(Z)-4-tridecen-l-yl acetate
Chemical Family: Lepidopteran pheromone
CAS Registry Numbers: 65954-19-0 and 72269-48-8
OPP Chemical Codes: , 12901 and 12902
Empirical Formula: C1^S.2g^2
Trade and Other Names:
Bedoukian: TPW Technical Pheromone
Consep: CheckMate TPW Technical Pheromone
CheckMate TPW
SPR1 Tomato Pinworm Sprayable Bead Pheromone
biosys: NoMateTPWMEC
Technical Lycopersilure
NoMate TPW Spiral
NoMate TPW Fiber
Technical Pheromone E/2-4-TDA
Agrisense Decoy TPW Clips
3M: MEC-Tomato Pinworm Pheromone
Basic Manufacturers:
Consep, Inc. .
213 Southwest Columbia St., PO Box 6059
Bend, OR 97702-1018
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Bedoukian
21 Finance Drive
Danbury,CT 06810
biosys -,-. ..',... ' ' .. .-'. , '- :. ' ' ' .' : ' " ''.. ' -
10150 Old Columbia Rd.
. Columbia, MD 21046. , .
3M Animal Care Products
3M Center, Bldg. 270-2N-p3
St. Paul, MN 55144-lQOo" , ,-; ;
B. UseProfile
The following is information on the currently registered uses with an overview
of use sites and application methods. A detailed table of these .uses, of tomato pinworm
technical pheromone (E)-4-Tridecen^l-yl acetate and (Z)-4-Tridecen-l-yl acetate can,
be found in Appendix A.
Type of Pesticide: Tridecenyl acetate is a biochemical insect pheromone.
Use Sites: Terrestrial food/feed crops: tomato plants '("
Target Pests: Tomato pinworm (TPW) (Keiferia lycopersicello).
Formulation Types Registered:
The technical grade active ingredients consist of two isomers:(E)-4-tridecen-l-
yl acetate and (Z)-4-trid^cen-l-yl acetate. There are three types of formulations
registered as end-use products. One formulation, the TGAI and, inert ingredients are
inside of a solid polymeric matrix known as a dispenser. A second formulation
consists of the TGAI encapsulated in beads, and a third formulation consists of the
TGAI embedded into polymeric fibers.
Method and Rates.of Application:
~ ' ' . v -
The end-use dispenser products are applied at rates of 200 dispensers per acre;
endiuse spray able bead products are applied at rates of 8 to 25 grams of product per
acre; and the end-use fiber products are applied at rates of 54 grams per acre. The
actual application rates of the active ingredient (tridecenyl aqetates) in all of these
formulations does not exceed 150 grams/acre/season. ,
3
-------
Equipment - Spray equipment is necessary for sprayable bead and fiber
formulations. No equipment is necessary for solid matrix
dispensers.
Timing - Two weeks after transplant of tomatoes, or if monitoring traps
capture 2-5 tomato pinworms per day.
Use Practice Limitations: None
C. Estimated Usage of Pesticide
According to Agency's database on biochemicals, in 1993, an insignificant
amount of tridecenyl acetate pheromone was applied to less than 5% of the national
acreage of tomatoes, mainly on those grown in California. ri- c"
~ r* ?.
D. Regulatory History ..-
Pesticide products containing tridecenyl acetates were initially registered in the
United States in 1982. Currently, there are eleven products registered to four
companies. These products employ the sex-attractant pheromone of the tomato
pinworm and are applied to fields of tomatoes to disrupt the mating behavior.
This reregistration case contains two active ingredients, which are currently
used in registered products. The two registered ingredients are: (E)-4-tridecen-l-yl
acetate (chemical number 12901), and (Z)-4-tridecen-l-yl acetate (chemical number
12902).
All of the tridecenyl acetate formulations are contained, embedded,
encapsulated or impregnated in a solid polymeric matrix or shell.
During Phase 3 of the reregistration process, the toxicology and ecological data
bases for tridecenyl acetates were evaluated and determined to adequately satisfy the
data requirements for biochemical control agents. , .
A number of actions have been taken by the Agency to provide regulatory
relief for pheromones. In February of 1993, the Agency published in the Federal
Register, a final rule exempting inert materials in polymeric matrix dispensers from the
requirements of a tolerance (58 FR 64493)'. ,
In March of 1994, the Agency published in the Federal Register, a final rule
exempting from the requirement of a tolerance, residues of arthropod pheromones
resulting from the use of these substances in retrievably-sized polymeric matrix
-------
dispensers with an annual application limitation of 150 grams active ingredient per
acre for pest control in or on all raw agricultural commodities (59 FR14757).
The experimental use permit (EUP) limit was raised to 250 acres for
pheromones in polymeric matrix dispensers, for testing of non-food use broadcast
pheromones and for straight-chained lepidopteran pheromones (sprayables). These,
actions were completed in 1994 and published in the Federal Register (59 FR 3681, 59
FR 34182 and 60 FR 168). . /. "' .
Tolerance exemptions for straight-chained lepidopteran pheromones
(sprayables) and for inert polymers in sprayable formulations (beads) Were published
in the Federal Register [8/31/95 (60 FR 45060) and 2/21/96 (61 FR 6550)].
This ReregistrationEligibiliiy Decision reflects a reassessment of all data '
which have been submitted in response to the reregistration process.
SCIENCE ASSESSMENT ''- ." ' ;. ' ,' 'v :-j... ; ;'/ - :"
A. Product Chemistry Assessment
All product chemistry data requirements are satisfied for the technical active
ingredient containing 93.00%(E)-4-trideceh-l-yl acetate and 2.96% (Z)-4-tridecen-l-yl
acetate. These data will support a Reregistratipn Eligibility Decision (RED).
1. Product Identity and Mode of Action
The technical grade active ingredient for this biochemical pesticide,
. consists of (E)-4-tridecen-l-yl acetate and (Z)-4rtrideeen-l-yl acetate.
Trideqenyl acetate is a sex attractant pheromone produced by female tomato
pinworms (Ketferia lycopersicelld) to attract males for mating. This
pheromone may be chemically synthesized and used as a biochemical
insecticide in polymeric dispensers, fibers, and beads. When the synthetic
pheromone is released it attracts adult^TPW males. Since the male TPW moths
cannot distinguish the artificially released pheromone from that released by a
female TPW moth, mating is disrupted and propagation is greatly reduced.
Thus eliciting a non-toxic mode of pesticidal action.
2. Tolerance Exemption and Food/Non-Food Use
Tridecenyl acetates are pheromone sex attractaiits and are not applied
directiy to crop(s), but rather impregnated onto polymeric dispensers, fibers,
and beads which are ultimately, applied within or on tomato fields. These
compounds belong to the class of lepidopteran pheromones which are
-------
Table I:
exempted from the requirement of a tolerance when used at application rates of
less than 150 grams of active ingredient per acre per season in or on all raw
agricultural commodities (FR 8/30/95 40 CFR ง180.1153). Additionally, an
exemption from the requirement of a tolerance has been established for the
tomato pinworm pheromone insecticides (E)-4-tridecen-l-yl acetate and (Z)-4-
tridecen-1-yl acetate, when applied to tomato plants (preharvest) from a tape
dispenser and by chopped fibers (40 CFR ง180.1064). .
3. Physical and Chemical Property Assessment ,
The structural formulas of (E)-4-tridecen-l-yl acetate and (Z)-4-
tridecen-1-yl acetate are:
CH3(CH2)7CH=CH(CH2)3CO2CH3
Empirical formulation:
Molecular Weight: 240.38^
CAS Registry Nos.: 72269-48-8 and 65954-19-0
(for E and Z respectively)
The Generic Physical and Chemical Data Requirements for Tridecenyl
Acetates TGAI:
tJ iJ ' > ' '>>
GaideUheNo. iSlB-lt '5
Color
Physical State
Odor
Melting point
Boiling point
Density, specific gravity
Solubility
Vapor pressure
Dissociation constant
Octanol/watcr partition coefficient
pH
Stability
."'- ;..<".-. !.. I"'1.. JPropeirties : '*.'".,
Colorless to faint yellow
Oily liquid
Mild, fruity
N/A
(Z): 120ฐ C; 1.03 mmHg
(E): 120ฐ C; 0.99 mmHg
0.876
Insoluble in water, soluble in hexane and
ethanol
<1.8 x lO'2 at 25ฐ C and 1.00 mmHg
N/A
0.929
N/A
Stable in heat and light
"....'. MRTDNo,
41647902
41647902
41647902
41647902
41647902
41647902
41647902
41647902
41647902
-------
B. Human Health Assessment
1. Toxicology Assessment
Adequate mammalian toxicology (iata are available on (E,Z)-4-tridecen-
1-yl acetates and will support a RED for the active pesticidal ingredients.
a. Acute Toxicity
All acute toxicology studies have been submitted and adequately
satisfy the requirements as set forth jn 40 CFR 158.690 for food/feed
.'. use. The following toxicology studies have been submitted to support
the reregistration of the active ingredient:
Table II: Acute Mammalian Toxicity Requirements for Tridecenyl Acetates
1 - '-- / Guideline ^ _ ^ -
"'.? '-. ^ " * > ' ' ""
152B-10 Acute oral tpx.(rat)
152B-1 1 Acutb dermal tox.(rabbit)
152B-12 Acute inhalation (rat)
152B-12 Acute intratracheal (rat)
152B-13 Primary eye irritation
(rabbit)
152B-14 Primary dermal irritation
. (rabbit)
152B-15 Dermal sensitization
'" ,' Results
f ,f ,ซ, "J ' ff J ff i ," ' ^
LD50>5g^cg
LD50>5g/kg
LD50>2.5mg/L
LC50>
450mg/animal
(5mปL)
None to Slight
Irritalion* '
Slight Erythema
Not a sensitizer**
,,,Toxic%,,,
, Category ,
IV
IV
IV
IV
m
IV
, N/A
; -,- -" " >'*, " ' '" -f
< , , MRi&'&a. '-", ' __ '
^ - , '-' ,'" 'Xf. r" .. ' ,
41928001, 42193803,
41594005,
42193804,41594006
41928005,41594007
41594007
41928004,42193805,
41594008
41928003,42193806,
41594009
41928006, 42192903
* Slight iritis and conjunctival irritation.
** Based on the Buehler Method.
b. Mutagenicity
The following mutagenicity studies support the reregistration of
the active ingredient:
-------
Table IH: Mutagenicity Requirements for Tridecenyl Acetates
^'.^^siy^^ &y.
Adeline &2B-&. ->' ^ '. < -V- . -^ "\
Ames Assay
Unscheduled DNA Synthesis
Chromosomal Aberration (CHO Cells)
, -'/ป' \' " i>'" ,'-'.f" ,'*;'
'" '/* t, *< ' /'*'/; V
".* J ft t , .-i_ t-..t ** f t t
v " . Results .,'. ... v / .'-.
Not mutagenic*
Negative
Negative
>!*flsibf&^ '.
41928007
41928008
41928009
The test substance was non-toxic and negative for mutagenicity to any of the five Salmonella
typhimurium tester strains with or with metabolic activation.
c.
Subchronic Assessment
Data from sub chronic toxicology studies evaluating compounds
(i.e., six to sixteen carbon unbranched alcohols, acetates and aldehydes)
similar in structure to the lepidopteran pheromones are available in the
public literature (Daughtrey et al. 1990, Subchronic toxicity evaluation
of tridecyl acetate in rats. Fundam.Appl. Toxicol. 14: 104-112). The
results indicate that there were no significant signs of toxicity in rats
other than those expected with longer term exposure to high doses of a
hydrocarbon. The findings were indicative of an overall low degree of
systemic toxicity following subchronic oral administration of tridecenyl
acetate at doses up to 1 g/kg body weight. It should be noted that no
significant acute toxicity effects were associated with the primary
alcohols, acetates or aldehydes evaluated. Based on the results from the
submitted acute mammalian toxicity studies which demonstrate low, if
any, toxicity and because adequate data exist in the public domain, no
additional data and/or information will be required.
2. Exposure Assessment
a. Dietary Exposure
An exemption from the requirements of a tolerance has been .
established for residues of arthropod pheromones when used in
retrievable-sized polymeric matrix dispensers in or on the raw
agricultural commodities when applied to growing crops at a rate not to
exceed 150 g/a.i./acre/year in accordance with good agricultural
practices (See 40 CFR 180.1124). The exemption was extended to
broadcast applications for lepidopteran pheromones on August 31,1995
(60 FR 45060). The Agency was unable to make a no-unreasonable-
adverse effects finding for other arthropod pheromone pesticides for use
on food crops. However, based on the data and/or information
submitted to support the registration of straight-chained lepidopteran
-------
pheromones, the Agency concluded thai the potential for such residues
is hot a dietary hazard. This conclusion was based on the lack of Sec.
6(a)(2) incident reports and the low acute mammalian toxiciry observed
in the lepidbpteran pheromones registered to date, the known ,
, metabolism of long-chain fatty acids, low application rates, low
exposure subsequent to application due to volatilization (MRJD
43509702), arid the results of the field residue studies (MRID
43509701). This compound is not applied directiy to tiie tomato plants
nor is it taken up or metabolized by tomato plants, but rather it is
; incorporated into dispensers or as a microencapsulated material.
Therefore, dietary exposure to this compound is expected to be minimal.
Consequently^ the Agency has determined that,; when used in
accordance with.good agricultural practices, a food tolerance for the
defined subset of lepidopteran pheromones, which includes (E,Z)^4-.
tridecen-1-yl acetates, is not necessary to protect the public health;
therefore, the Agency established an exemption from the requirement
of a tolerance for this group of active pesticidal ingredients when used
at less than 150 g/a.i./acre/year (40 CFR 18p.l 153).
b. Occupational and Residential Exposure
- Based on thfe application methods (i.e., encapsulated and fiber
formulations), tiie potential for dermal, eye, and inhalation exposures to
the pesticide foppesticide handlers exists. Because of the lack of
mammalian toxicity, as demonstrated in the acute and subchronic
toxicity studies, worker exposure data to the active ingredient are not
required.
3, Human Risk Assessment '
Although the potential for dermal and inhalation exposures to the
pesticide for pesticide handlers exists, the potential is addressed by appropriate
labeling. Eye irritation remains an area of concern for the final products and
should-be addressed with the appropriate precautionary label statements. There
are no subchronic or chronic risks expected for, exposure to the TGAI.
Moreover, the Agency has not received any 6(a)(2) reports or Incidences of
poisoning (for the E and Z isomers of tridecenyl acetates).
The potential risks to humans from both nbndietary and dietary routes
are considered negligible for those pheromones, given the lack of adverse *
effects presented by existing mammalian toxicology data. Lack of adverse
effects is demonstrated in the submitted acute mammalian toxicology studies,
low application rates, even lower exposure subsequent.tp application due.to .
-------
volatilization, the results of the field residue studies, and known metabolism of
long-chain fatty acids. Therefore, no* additional information and/or toxicology.
data are required. In the event that the technology for manufacturing and/or
synthesizing the compound and/or use pattern changes such as to increase
toxicity from manufacturing impurities or the likelihood of exposure, the
Agency may reevaluate the need for additional toxicology testing on the
technical grade material.
C. Environmental Assessment
There are no outstanding environmental effects data requirements. Sufficient
data have been provided for an environmental fate and effects assessment.
1. Ecological Toxicity Data
All of the ecological effects data requirements for tridecenyl acetates
have been adequately fulfilled. A review of all available ecological toxicity
data indicate that tridecenyl acetates are not likely to cause adverse effects in
non-target avian, fish and aquatic invertebrate species.
Table IV: Ecological Toxicity - Tier I Guideline Requirements for Tridecenyl
Acetates
Guideline
: NO.
154B-6
154B-7
- 'ซ>'?'>
*ซ*' ;;;(
Avian acute oral -
bobwhite quail
Avian subacute dietary-
bobwbite quail
,v^;-"V ^ " I"***??* -X ,'ซ- ",C 1
LD5o>2250mg/kg. Tridecenyl acetate is
practically non-toxic to bobwhite quail. Test
material 99.0%.
LD50>2000mg/kg. Tridecenyl acetate is
practically non-toxic to bobwhite quail. Test
material 95.78%.
LCjo > 5620 ppm. Tridecenyl acetate is
practically non-toxic to bobwhite quail. Test
material 99.0%.
LCjg > 5620 ppm. Tridecenyl acetate is
practically non-toxic to bobwhite quail. Test
material 95.78%. '
7 HQBB""'
41928010
42193807
41928011
42193808
10
-------
^ ^ -. f v:\ w.
Guideline
^ ^ ~ NO*- :
154B-8
'
154B-9
154B-10
154B-11
_ซ'_ซ ; study ":\, ; ,;
'* ,' , '" ''
Fish toxicity - rainbow
trout
i f
Invertebrate toxicity -
Daphnia mdgna
Nontarget plants
' \
Nontarget,insects
' ^ y v^i
, '/ ItesaKa, ^ "J '" "1
' i ' ' f '
LC30 >100 mg/L. Tridecenyl acetate is practically
non-toxic to coldwater fish. Test material 99.0%.
LC30 >120 mg/L. Tridecenyl- acetate is practically.
non-toxic to coldwater fish. Test material
95.78%; . .
LG50 =^L6 mg/L. Tridecenyl acetate is moderately
toxic to Daphnia magna . Test material 99.0%.
The LCj0 of tridecenyl acetate isnot determined.
Test material 95.78%, ,
Waived because tridecenyl acetate is a sex
attractant pheromone specific to the tomato
pinworm. ,
Waived because tridecenyl acetate is a sex
attractant pheromone specific to the tomato
pinworm.
^^iBIHB'^
' , ss As " fff
41928012
42193809
41928013
42192810
1 The toxicity data, listed in the chart above, suggests that tridecenyl
acetates are practically non-toxic to avian and freshwater fish species and
moderately toxic to freshwater invertebrates. In the Agency's review of the fish
studies, it was noted that these data were collected in a static test with an oily
residue present in ali test solutions and no verification of actual concentrations.
of tridecenyl acetates in the water; thus raising concerns that the true toxicity of
the test material could be deterniined. However, based on this pesticide's non-
toxic mode of action (a sex attractant pheromone impregnated in fibers,
dispensers, and sprayable beads), its low acute mammalian toxicity, and its
limited use pattern (i.e. only in tomato fields), additional data are not required.
2.
Environmental Fate
Environmental fate Tier n studies for biochemicals are not imposed
unless adverse effects are observed in Tier I Environmental Expression testing
with wildlife, fish and aquatic invertebrates. The Agency will not impose any
environmental fate requirements for reregistration of the currently registered
products containing tridecenyl acetates.
11
-------
IV. RISK MANAGEMENT AND REREGISTRATION DECISION
A. Determination of Eligibility
Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after
submission of relevant data concerning an active ingredient, whether products
containing the active ingredients are eligible for reregistration. The Agency has
previously identified and required the submission of the generic (i.e. active ingredient
specific) data required to support reregistration of products containing tridecenyl
acetates active ingredients. The Agency has completed its review of these generic
data, and has determined that the data are sufficient to support reregistration of all
products containing tridecenyl acetates. Appendix B identifies the generic data
requirements that the Agency reviewed as part of its determination of reregistration
eligibility of tridecenyl acetates, and lists the submitted studies that the Agency found
acceptable.
The data identified in Appendix B were sufficient to allow the Agency to assess
the registered uses of tridecenyl acetates and to determine that tridecenyl acetates can
be used without resulting in unreasonable adverse effects to humans and the
environment. The Agency, therefore, finds that all products containing tridecenyl
acetates as the active ingredients are eligible for reregistration. The reregistration of
particular products is addressed in Section V of this document.
The Agency made its reregistration eligibility determination based upon the
target data base required for reregistration, the current guidelines for conducting
acceptable studies to generate such data, published scientific literature, etc. and the
data identified in Appendix B. Although the Agency has found that all uses of
tridecenyl acetates are eligible for reregistration, it should be understood that the
Agency may take appropriate regulatory action, and/or require the submission of
additional data to support the registration of products containing tridecenyl acetates, if
new information comes to the Agency's attention or if the data requirements for
registration (or the guidelines for generating such data) change.
1. Eligibility Decision
Based on the reviews of the generic data for the two active ingredients,
the Agency has sufficient information on the health effects of tridecenyl
acetates and on their potential for causing adverse effects in fish, wildlife, and
the environment. The Agency has determined that tridecenyl acetate products,
labeled and used as specified in this Reregistration Eligibility Decision, will not
pose unreasonable risks or adverse effects to humans or the environment.
Therefore, the Agency concludes that products, containing tridecenyl acetates
for all uses are eligible for reregistration.
12
-------
2. Eligible and Ineligible Uses
The Agency has determined that all currently registered uses of
tridecenyl acetates are eligible for reregistration.
B. Regulatory Position
The following is a summary of the regulatory positions and rationales for
tridecenyl acetates. Where labeling revisions are imposed, specific language is set
forth in Section V of this document.
.1. - Tolerance Reassessment
Tridecenyl acetates, as straight chain lepidbpteran pheromones, are
exempt from the requirement of a tolerance [Federal Register citation: 40 CFR
ง180.1043 and 40 CFR ง180.1153.]
2. Endangered Species Statement
Currently, the Agency is developing a program ("The Endangered
Species Protection Program") to identify all pesticides whose use may cause
adverse impacts on endangered and threatened species and to implement
mitigation measures that will eliminate the adverse impacts. The program
would require use restrictions to protect endangered and threatened species at
the county level. Consultations with the Fish and Wildlife Service may be
necessary to assess risks to newly listed species,or from proposed new uses. In
the future, the Agency plans to publish a description of the Endangered Species
Program in the Federal Register and have available voluntary county-specific
bulletins. Because the Agency is taking this approach for protecting
endangered and threatened species, it is not imposing label modifications at mis
time through the RED. Rather, any requirements for product use modifications
will occur in the future under the Endangered Species Protection Program.
3. Labeling Rationale
Precautionary Labeling:
The Agency has reexamined the toxicological data base for tridecenyl
acetates and concluded that the current precautionary labeling (/. e., Signal
Word and Statement of Practical Treatment) adequately mitigate the risks
associated with the use of these pheromones. Due to the Primary Eye irritation
response (Toxicity Categoiry ID), the Agency will require the appropriate
Signal Word (Caution) and Precautionary Statements (Causes slight eye
13
t -.-
-------
irritation. Avoid contact with eyes or clothing. Wash thoroughly with soap
and water after handling).
Worker Protection Standard:
According to Pesticide Regulation (PR) Notice 93-7, "Labeling
Revisions Required by the Worker Protection Standard (WPS)", WPS does not
apply to attractants used in insect dispensers. However the microencapsulated
products are within the scope of the WPS and must bear all of the labeling
requirements stipulated in PRNotices 93-7 and 93-11.
Environmental Hazard Statement:
To mitigate potential risks to fish and aquatic invertebrates the Agency
is requiring all microencapsulated products containing tridecenyl acetates to
bear a Precautionary Environmental Hazard Statement which prohibits direct
application to surface water. It is the opinion of the Agency that label
restrictions to prohibit direct application to bodies of water will effectively
mitigate risks to fish and aquatic invertebrates. Refer to Section V.
V. ACTIONS REQUIRED OF REGISTRANTS
This section specifies the data requirements and responses necessary for the
reregistration of both manufacturing-use and end-use products.
A. Manufacturing-Use Products
1. Additional Generic Data Requirements
The generic data base supporting the reregistration of tridecenyl acetates
for the above eligible uses has been reviewed and determined to be
substantially complete.
2. Labeling Requirements for Manufacturing-Use Products
There are currently three manufacturing-use products registered. These
are the 3M Company's MEC Tomato Pinworm Pheromone Concentrate
(10350-34), Bedoukian's TPW,Technical Pheromone (52991-3) and Consep's
Checkmate TPW Technical Pheromone (56336-7). To be in compliance with
FIFRA, manufacturing use product labeling must comply with all current EPA
regulations, PRNotices and applicable policies. The MP labeling must bear
the following statement under Directions for Use:
14
-------
"Only for formulation into a pheromone for the following use: as ah
attractant in a mating disrupter."
: . ... . ; ,."--" ,'!.'.. . '--'' . ., . ""'."- ...... _
An MPfegisfrant may, at his/her discretion, add one of the following
statements to an MP label under "Directions for Use" to permit the
reformulation of the product for a specific use or all additional uses supported
by a formulator or user group:
(a) "This product may be used to formulate products for specific
use(s) not listed on the MP labej if the formulator, user group, or
grower has complied with U.S. EPA submission requirements
, regarding support of such use(s)." ,
(b) "This product may be used to formulate products for any
additional use(s) not listed on the MP label if the formulator,
user group, or grower has complied with U.S. EPA submission
requirements regarding support of such use(s)."
B. End-Use Products v-
- '". . .1 ' , ,'*_',..,
1. Additional Product-Specific Data Requirements
Section 4(g)(2)(B) of FIFRA calls for the Agency to obtain any needed
product-specific data regarding the pesticide after a determination of eligibility
has been made. Registrants must review previous data submissions to ensure
that they meet current EPA acceptance criteria and if not, commit to conduct
new studies. If a registrant believes that previously submitted data meet current
testing standards, then study MRID numbers should be cited according to the
instructions in the Requirement Status and Registrants Response Form
provided for each product.
' - ' . . f . ' L ---,'--.-=--, ', ~~ - - - " ' - ' '-
2. Labeling Requirements for End-Use Products:
, Worker Protection Standard:
The labeling of all microencapsulated end-use products containing
tridecenyl acetate must comply with EPA's current regulations and
requirements as specified in 40 CFR 156.10 and other applicable notices.
Environmental Hazard: ^
s . - - - - . _' - ,.--_, ' _- .' -. .^__
The following Environmental Hazard Statement must appear on the
labeling of all products containing tridecenyl acetates:
15
-------
"Do not apply directly to water, or to areas where surface water is present or to
intertidal areas below the high-water mark. Do not contaminate water when .
disposing of equipment wash water or rinsate."
C. Existing Stocks ,
Registrants may generally distribute and sell products bearing old
labels/labeling for 26 months from the date of the issuance of this Reregistration
Eligibility Decision. Persons other than the registrant may generally distribute or sell
such products for 50 months from the date of the issuance of this RED. However,
existing stocks time frames will be established case-by-case, depending on the number
of products involved, the number of label changes, and other factors. Refer to
"Existing Stocks of Pesticide Products; Statement of Policy"; Federal Register.
Volume 56, No. 123, June 26,1991.
The Agency has determined that registrants may distribute and sell tridecenyl
acetate products bearing old labels/labeling for 26 months from the date of issuance of
this RED. Persons other than *!te registrant may distribute or sell such products for 50
months from the date of the kiiiiance of this RED. Registrants and persons other than
registrants remain obligated to meet pre-existing Agency imposed label changes and
existing stocks requirements applicable to products they sell or distribute.
16
-------
VI. APPENDICES
17
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GUIDE TO APPENDIX B
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Appendix B contains listings of data requirements which support the reregistration for
active ingredients within the case tridecenyl acetates covered by this Reregistration Eligibility
Decision Document It contains generic data requirements that apply to tridecenyl acetates in all
products, including data requirements for which a "typical formulation'' is the test substance.
The data table is organized in the following fprmat:
1. Data Requirement/Column 1). The data requirements are listed in the order in which
they appear in 40 CFR Part 158. the reference numbers accpmpanying each test refer to the test
protocols set in the Pesticide Assessment Guidelines, which are available from the National
Technical information Service, 5285 Port Royal Road, Springfield, VA 22161 (703) 487-4650.
2. Use Pattern (Column 2). This column indicates the use patterns for which the data
requirements apply. The following letter designations are used for me given use patterns:
A Terrestrial food
B Terrestrial feed
C Terrestrial non-food
D Aquaticfopd
E Aquatic non-food outdoor ,
. F Aquatic nonrfopd industrial
G Aquatic non-food residential
H Greenhouse food -
I - Greenhouse non-food
J Forestry .
K Residential
L Indoor food
M Indoor non-food
'' ' ^ - N Lidoormedical
O Indoor residential
3. Biblioejaphic citation (Column 3). If the Agency has acceptable data in its files, this
column lists the identifying number of each study. This normally is the Master Record
Identification (MRID) number, but may be a "GS" number if no MRJD number has been
assigned. Refer to the Bibliography appendix for a complete citation of me study.
25
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GUIDE TO APPENDIX G
1. CONTENTS OF BIBLIOGRAPHY. This bibliography contains citations of all studies
considered relevant by EPA in arriving at the positions and conclusions stated
elsewhere in the Reregistration Eligibility Document. Primary sources for studies in
this bibliography have been the body of data submitted to EPA and its predecessor
agencies in support of past regulatory decisions. Selections from other sources
including the published literature, in those instances where they have been considered,
aremcluded. , .''.,.
2. UNITS OF ENTRY. Theumtof entry in this bibliography,is called a H5tudy" In the
: case of published materials, this corresponds closely to an article. In the case of
unpublished materials submitted to the Agency, the Agency has sought to identify
documents at a level parallel to the published article from within the typically larger
volumes in .which they were submitted. The resulting "studies" generally have a
distinct title (or at least a single subject), can stand alone for purposes of review and
can be described with a conventional bibliographic citation. The Agency has also
attempted to unite basic documents and commentaries upon them, treating them as a
single study.
3... IDENTIFICATION OF ENTRIES. The entries in this bibliography are sorted
numerically by Master Record Identifier, or "MRID number". This number is unique
to the citation, and should be used whenever a specific reference is required. It is not
related to the six-digit "Accession Number" yvhich has been used to identify volumes
of submitted studies (see paragraph 4(d)(4) below for further explanation). In a few
cases, entries added to the bibliography late in the review may be preceded by a nine
character temporary identifier. These entries are listed after all MRID entries. This
temporary identifying number is also to be used whenever specific reference is
needed. ^ ^
4, FORMOF ENTRY. In addition tothe Master Record Identifier (MRID), each entry
consists of a citation containing standard elements followed, in the case of material
submitted to EPA, by a description of the earliest known submission. Bibliographic
conventions used reflect the standard of the American National Standards Institute
(ANSI), expanded to provide for certain special needs.
a Author. Whenever the author could confidently be identified, the Agency has
chosen to show a personal author. When no individual was identified, the
Agency has shown an identifiable laboratory or testing facility as the author.
When no author or laboratory could be identified, the Agency has shown the
first submitter as the author. ,, -
hl \ . ' ' , -. . . . j , . > . '-,.'_ t i ..,-. .' . ., . r ;
b. Document date. The date of the study is taken directiy from the document.
When the date is followed by a question mark, the bibliographer has deduced
the date from the evidence contained in the document. When the date appears
';. '-A- --,- ' "-' ' ; -- ;-,;.. . : '" :'..' ''.".;' . ;'---' '. .- ..---'." ;
-------
as (19??), the Agency was unable to determine or estimate the date of the
document
c. Title. Li some cases, it has been necessary for the Agency bibliographers to
create or enhance a document title. Any such editorial insertions are contained
between square brackets. '
d. Trailing parentheses. For studies submitted to the Agency in the past, the
trailing parentheses include (in addition to any self-explanatory text) the
following elements describing the earliest known submission:
(1) Submission date. Thedate of the earliest known submission appears
immediately following the word "received."
(2) Administrative number. The next element immediately following the
word "under" is the registration number, experimental use permit
number, petition number, or other administrative number associated
with the earliest known submission.
(3) Submitter. The third element is the submitter. When authorship is
defaulted to the submitter, this element is omitted.
(4) Volume Identification (Accession Numbers). The final element in the
trailing parentheses identifies the EPA accession number of the volume
in which the original submission of the study appears. The six-digit
accession number follows the symbol "CDL," which stands for
"Company Data Library." This accession number is in turn followed by
an alphabetic suffix which shows the relative position of the study
within the volume.
30
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BIBLIOGRAPHY
MRID
CITATION
41594005
41594006
41594007
41594008
41594009
41647902
41928001
41928003
41928004
41928005
41928006
Kuhn, J. (1989) Checkmate TPW: Acute Oral Toxicity Study in Rats: Lab
Project Number: 6630-89. Unpublished study prepared by Stillmeadow Inc
12p.... -..'. ; ' ; ; '' :, , ;:/;..; : - ;;;'..
Kuhn, J. (1989) Checkmate TPW: Acute Dermal Toxicity Study in Rabbits:
Lab Project Number: 6631-89. Unpublished study prepared by Stillmeadow,
Inc. 13 p. :
Holhert, M. (1989) Checkmate TPW: Acute,Pulmonary (Litratracheal)
Toxicity Study in Rats: Lab Project Number: 6633-89. Unpublished study
prepared by Stillmeadow, Inc. 13 p.
Kuhn; J. (1990) Checkmate TPW: Primary Eye Irritation Study in Rabbits: Lab
Project Number: 6791-90. Unpublished study prepared by Stillmeadow Inc
19p.
Kuhn, J. (1989) Checkmate TPW: Primary Dermal Irritation Study in Rabbits:
Lab Project Number: 6632. Unpublished study prepared by Stillmeadow Inc
13 P-;" ''. -..-.. ' ' .'... .- .. ; :.';.., ','...
: " "I .v " " " '--.'' ' . ^ , . .
Maloney, R. (1990) Product Chemistry: Analysis and Certification of
Ingredients: Bedoukian TPW Technical Pheromone. Lab Project Number
TPW/A-3. Replaced by MRID 42720901. Unpublished study prepared by
Bedoukian Research, Inc. 43 p.
' " . ."',.--'"'. " '" ". " ' ' - . ^' \.
Kuhn, J. (1991) Acute Oral Toxicity of E/Z-4-tridecen- IrYL Acetates in Rats.
Unpublished study prepared by Iain Weatherston Scentry Lie. 12 p.
Kuhn, J. (1991) Primary Dermal Irritatioh of E/Z-4-triceden-l-YL Acetates in
Rabbits. Unpublished study prepared by Iain Weatherston Scentry Inc. 14 p.
Kuhn, J. (1991) Primary Eye Irritation of E/Z-4-Tridecen-l-YL Acetates in
Rabbits. Unpublished study prepared by Iain Weather ston Scentry Inc. 20 p.
Holbert, M. (1991) Acute Pulmonary (jmtratracheal) Toxicity of
E/Z-4-Tridecen-l-YL Acetates in Rats. Unpublished study prepared by Iain
Weatherston Scentry Inc. 13 p. ,
Kuhn, J. (1991) Skin Sensitization of E/Z-4-Tridecen-l^YL Acetates in Guinea
Pigs. Unpublished study prepared by Iain Weatherston Scentry Inc. 21^ p.
31
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BIBLIOGRAPHY
MRTO
CITATION
41928007 Lawlor, T. (1991) Mutagenicity Assay on Tomato Pinworm Pheromone
jE/Z-4-l-YL Acetates] in the Salmonella/Mammalian-Microsome Reverse
Mutation Assay [Ames Test] with a Confirmatory Assay. Unpublished study
prepared by Iain Weatherston Scentry Inc. 3 5 p.
41928008 McKeon M. (1991) Assay of E/Z-4-Tridecen-l-YL Acetates for Unscheduled
DNA Synthesis in Rat Liver Primary Cell Cultures. Unpublished study
prepared by Iain Weatherston Scentry Inc. 27 p.
41928009 Murli, H. (1991) Mutagenicity Assay of E/Z-4-Tridecen-l-YL Acetates
Measuring Chromosomal Aberration in Chinese Hamster Ovary [CHO] Cells.
Unpublished study prepared by Iain Weatherston Scentry Inc., 34 p.
41928010 Campbell, J.; Grimes, J.; Smith, G. et al (1991) Acute Oral Toxicity of
E/Z-4-Tridecen-l-YL Acetates to Northern Bobwhite Quail. Unpublished
study prepared by Iain Weatherston Scentry Inc. 18 p.
41928011 Beavers, J.; Grimes, J.; Smith, G. (1991) Dietary LC50 Toxicity Study of .
E/Z-4-Tridecen-l-YL Acetates in Northern Bobwhite Quail. Unpublished
study prepared by Iain Weatherston Scentry Inc. 16 p.
41928012 Graves, W.; Peters, G. (1991) 96-Hour Static Acute Toxicity of E/Z
-4-Tridecen-l-YL Acetates to Rainbow Trout. Unpublished study prepared by
Iain Weatherston Scentry Inc. 20 p.
41928013 Holmes, C.; Peters, G. (1991) 48-Hour Static Acute Toxicity of
E/Z-4-Tridecen-l-YL Acetates to the Cladoceran [Daphnia magna]. Un-
published study prepared by Iain Weatherston Scentry Inc. 21 p.
42192903 Nitka, S. (1991) Guinea Pig Sensitization (Buehler) (FIFRA): Decoy TPW
Clips: Lab Project Number: 91198. Unpublished study prepared by
Agrisense. 31 p ,
42193803 Nitka, S. (1991) Acute Oral Toxicity in Rats (FIFRA): E-4-Tridecen-l-OL
Acetate: Final Report: Lab Project Number: 91096-3. Unpublished study
prepared by Consumer Product Testing. 10 p.
42193804 Nitka, S. (1991) Acute Dermal Toxicity in Rabbits (FIFRA): E-4-
Tridecen-1-OL Acetate: Final Report: Lab Project Number: 91096-4.
Unpublished study prepared by Consumer Product Testing, lip.
32
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BIBLIOGRAPHY
" '
MRH>
CITATION
42193805 Nitka, S. (1991) Primary Ocular Irritation in Rabbits (FIFRA):E-4-Tri
decen-1-OL Acetate: Final Report: Lab Project Number: 91096-2.
Unpublished study prepared by Consumer Product Testing. 14,p.
42193.806 TSfitka,S. (1991) Primary Dermal Irritation in Rabbits (FIFRA): E-4
Tridecen-1-OL Acetate: Final Report: Lab Project Number: 91096-1.
Unpublished study prepared by Consumer Product Testing. 15 p.
42193807 Campbell, S.; Lynn, S. (1991) Tomato Pinworm Pheromone: An Acute Oral
Toxicity Study with the Northern Bobwhite: Lab Project Number: 251-105.
Unpublished study prepared by Wildlife International Ltd. 19 p;
42193808 Lynn, S.; Grimes^ J.; Smith, G. (1991) Tomato Pinworm Pheromone: A
Dietary LC50 Study with the Northern Bobwhite: Lab .Project Number:
251-106. Unpublished study prepared by Wildlife International Ltd. 19 p.
42193809 Holmes, C.; Smith, G. (1991) Tomato Pinworm Pheromone: A 96-Hour Static
Acute Toxicity Test with the Rainbow Trout (Oncorhynchus mykiss): Final
Report: Lab Project Number: 251A-1021 Unpublished study prepared by
Wildlife International Ltd. 20 p.
42720901 Maloney, R. (1993) Product Chemistry: Analysis and^Certification of
Ingredients of Bedoukian TPW Technical Pheromone: Lab Project Number:
TPW/A-3. Replacement of MRH) 41647902. Unpublished study prepared by
Bedoukian Research, Inc. 43 p.
33
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34
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The following is a list of available documents for tridecenyl acetates that my further
assist you in responding to this Reregistration Eligibility Decision document. These -
documents may be obtained by the following methods:
Electronic' , " . '.,.' ,,, ' ; . '". , ;.,...- .'...;.-..... ;.-,... V-V ' '=: .-'
File format: Portable Document Format (.PDF) Requires Adobeฎ Acrobat or compatible
reader. Electronic copies can be downloaded from the Pesticide Special
Review and Reregistration Information System at 703-308-7224. They also are
available on the Internet on EPA's gopher server, GOPHER.EPA.GOV, or
using ftp on FTP.EPA.GOV, or using WWW :(World Wide Web) on
WWW.EPA.GOV., or contact Anne R. Leslie at (703)-308-8727.
1. PRNotice86-5. . ., '
, 2. PR Notice 91-2 (pertains to the Label Ingredient Statement);
3: A full copy of this RED document.
4. A copy of the fact sheet for tridecenyl acetates.
The following documents are part of the Administrative Record for tridecenyl acetates
and may included in the EPA's Office, of Pesticide Programs Public Docket. Copies of these
documents are not available electronically, but may be obtained by contacting the person
listed on the Chemical Status Sheet. . :
1. Health and Environmental Effects Science Chapters. \
2. .Detailed Label Usage Information System (LUIS) Report.
The following Agency reference documents are not available electronically, but may
be obtained by contacting the perspn listed on the Chemical Status Sheet pf this RED
document. - , . ' , . :
1. The Label ReviewManual.
' - / .- '...,'.:. ,.;.,',
2. EPA Acceptance Criteria
35 .
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