### Docke t N um ber EPA- HQ-OPP -20 14-0616 W\VW. r egu lati o n s.gov



### 4-(or 5) Chloro-2-Methylcyclohexanecarboxlic Acid, I ,1-Dimethyl Ester (Trimedlure) Combined Work Plan , Summary Document , and Proposed Interim Registration Review Decision Case Number 6045

December , 2015



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### Table of Co ntents Introduction 3 Statutory and Regulatory Authority 3 Trimedlure Che mical Facts 4 Use and Usage Information 4 Recent Actions 5 Sc ientific Assessments 5 Co mbin ed Work Plan , S ummary Document , and Proposed Interim Registration Review Decision 9 Nex t Steps and Timeline 9 References 10 Appendix A- Additional Areas Considered in the Trimedlure Registration Review 11

2

### I NTROD UCT IO N T h e docket for 4-(or 5) chloro

- 2 -m ethylc yclo hexanecarboxlic acid, l , !-dimethyl ester (t

rim edl ure) is now open (EPA- HQ-OPP- 2015-06 16), i nitiating the first public co mment period for thi s registrat ion rev iew. This document is the E nvironmental Pro t ect io n Agency's (E PA or the Age ncy) combined 

### Work Plan , Summary Document, and Propo sed Int erim Registration Review Decision for trimedlure

. 

### It is being issued pursuant to 40 CFR Sec tion s 155.50 , 155.56, and 155.58. This document explains w hat E P A·s Office of Pesticide Programs knows about trimedlure, highli ghting antic ipated data and assessment needs and prov iding an anticipated timeline for completing trimedlure registration review. It a lso includes the Age nc y's Proposed Interim Registration Review Decision for trimedlure. In addition to genera l areas on wh ic h the pub li c may wish to comment, the Appendix hi g hli gh t s topics of special inte r est to the Age ncy where addition a l information co uld be of par ti cula r use. A regi stration revi ew decision is the Agency's determination of whether a pesticide meets, or doe s not meet , the s tandard for registration under the Federal In sec ticide , F ungicide, and R odenticid e Act (F IFRA )
. The Agency may issue, w hen it determines it to be appropriate, an interim regi stration review dec isio n before completing registration review. The interim registration review decision may requir e new ri sk mitigation measures , imp ose interim risk mitigation measures , id entify data or information required to comp lete th e review, and include sched ules for submitt i ng the required data, conducting a new risk assessment and comp letin g registration review. The active ingred ie nt trimedlure i s a sy nth et ic arthropod pheromone that is registered for use in manufacturing of e nd-u se pheromone produc t s intended for agricu ltural use for the control of the insect pest. Mediten·anean Fruit Fly. Currently

. there are no registered end

- use products containing trimedlure. The pheromone is intended for use in traps and lures to attrac t fruit flies in infested fruits and nuts orchards and vegetable crops. Th e EPA

- approved manufacturing

- use product label restricts the product to being formulated only into end-use products that are polymeric-matrix removable dispensers. If these dispensers are contained in traps and lures, and contain trim e dlure as th e ir so le active ingred ien t , these end-use product s are exe mpt from reg ist ration per 40 CFR part 1 52
. 25(b). The Biopesticide R ereg i stration Action D ocume nt ( BRAD ) for trimed l ure was comp leted on J u ly 26 , 2001 , and is ava il ab le at: http: //\\ww3 .epa.gov / pes t icides/ chem search/ reg act ions/ registration/decision PC

- 112603 26- J ul-0 !
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. 136704888.95198873 1 .1440526185

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### STATUTORY AND R EGU LATORY AUT HORIT Y Th e Food Quality Protection Act (FQPA) of 1996 mandated a reg istration rev iew program. All pesticides distributed or sold in the U .S. gene rall y mu st be registered by EPA, based on scientific data showi ng that they will not cau se unreasonab le ri sks to human health or the enviro nment when used as directed on product labeling. The registration review program is intended to make sure that , as the ability to assess ri s k evo lves and a s polic ies and practices


### 3change, all reg iste red pesticides continu e to meet the s tatutory standard of no unreasonable ad ve rs e effects to hwnan he a lth or the environment. C hanges in sc ienc e, public policy , and pe s ticide use practices wi ll occur over time. Throu g h the registration review program , the Agency periodical ly reeva luates pesticides to m ake sure that as chang e occ urs, products in the marketplace are safe to u se . Information on thi s program is provided at W\.vw

. epa . gov/ oppsrrd 1 / registration review /
. The Age ncy is implementing the regi strati o n rev iew program pursuant to Section 3(g) of F IFRA , and will rev iew eac h registered p es ticid e eve ry 15 years to determine whether it co ntinues to meet th e FI FRA s tandard for r eg is trati o n. The regulation s gove rning registration re v iew begin at 40 C FR 

### § 155.40. The Agency will consider benefit s information and data as required by FIFRA. The public phase of registrati o n review begins when the initial docket is opened for each case. T he docket is the Agency 's o pportunity to state what it knows about the pe s ticide and what add itional risk analyses and data or information it b e li eves are needed to make a re gistration re v iew decision. Trimedlure C HEM I CAL FACTS

PC code 112603 Case Nwnber 6045 CAS N umb er 12002-53-8 Year first re gistered 2001 Pesticide Type Biopesticid e C he mical Chemical clas s Pheromone Bi opes ticide Jul y 26 , 2001 R e registrati on Act io n D oc ument ( BRAD ) Cu mulative Group E PA has not made a co mmon mechani s m of tox icity finding as to trimedlure and any o th e r s ub stances , and trimedlure does not appear to produce a toxic metabolite produc e d by other su b stance s. 40 CFR Citation 40 CFR 

### § 180.1124 Arthropod pheromone s, exem ption from the requirement of a to le ranc e Dual-use Biochemical pes ticidal u ses only. Non -p esticidal u ses No non-pe s ticidal u ses of trimedlure. Reg ulatory Action L eader Gina Burnett , burnett.gina @ epa.gov , 703-605-0513 Biopesticide and Andy Bryceland , br yce land.andy @epa.go v, 70 3 -305-6928 Pollution Pr evention Division , Team Leade r USE AND USAGE INFORMATIO N Trimedlure is r egis te r e d for use in the manufacturing and formulating of e nd-use pheromone p roducts intended for agricultural u se fo r the control of the in sec t pest , Mediten·anean Fruit Fly. Below is a s umm ary of the u se / u sage oftrimedlure.



### 4Summary ofUse The pesticide trimedlure is a synthetic arthropod pheromone regi s tered for u se in th e manufacturing of e nd-u se pheromone products intended fo r a g ri c ultur al use for the contro l of the in sect pest. Mediterranean Fruit Fly

. The pheromone i s intended for use in traps and lures to attract fru it flies in infested fruit and nut orchards and vegetable crop s . Per the EPA approved product label , the registered manufacturing-use pro duc t may only be formulated into e nd-use products that are r emovable di s p e n se r s. The dispensers mu st b e comprised of polymer that is impre g nated with the active ingredient , trimed lurc. fn accordance with 40 CF R 

### § 1 80
. 1124 , arthropod pheromone s , when us e d in retrievab ly s ize d po l ymeric matrix dispen se rs , are exe mpt from the r equ ire me nt of a toleranc e in o r on all ra w agricultural commod itie s w hen appl ied to growing crops at a rat e not to exceed 150 grams ac ti ve ingredient/acre / year in acco rdance with good agricultural practices. Use S ite s Commerc ial and residen ti a l fruit and nut orchards and vegetable crops . S ummary of Usage No annual usa ge dat a has b ee n reported for tri med lure. Fo rmu lation Type (s) Pol y meric

- matrix r e movable d ispe n sers . T ec hnical Registrant( s) l SP Fine Chemicals Inc. No. ofRegistrations One manufacturin g-use product. Res tri cte d Use No


### RECENT ACTI O NS There are no recent actions for trim e dlure. 

### SC I EN TIFI C ASSESSMENTS A summary of the Age nc y ' s human healt h , env ironmental fate and eco logical ris k a ss e s sments , 4-(or 5 ) chloro

- 2 -me th ylcyclohexanecarbox li c acid , 1 , 1-dimethyl ester (tri medlure) Biopest ic id e Reregistration Act io n Do cume nt ( B RAD) (July 26 , 2001 ) is presented b elow. F or the detailed ri sk asse s smenrs , see the trimedlure public docket (EP A -HQ- O PP- 20 15-0616) at www . reg ulati o n s . gov . 

### Human H ea lth Assess m ent 

### Hazard C har acte ri zation an d Ri s k The toxicological database is considered comple t e for characteri z in g hazard and assessing risk from trimedlu re. No additional studies are an ticip ated to be needed f or regi s trat ion review.



### 5

### The mode of action for pheromones is target specific. Pheromones act by modifying behavior of the target pest species, are applied at low concentrations close to those found in nature and dissipate rap idl y (OECD , 2002). The toxicological database for trimed lure is considered complete. The data requirements for acute toxicity studies for trimed lure were fulfi ll ed by data presented in a technical journal article which indicate low toxicity via the ora l , dermal and inhalation routes of exposure (Toxicity Category III for oral and dermal , Tox ic ity Category IV for inhalation). It is not irritating to the skin or eyes (Toxicity Category IV) (U.S. EPA, 2001)
. The Agency waived the requirements for subchronic studies (90-day oral , dermal and inhalation , mutagenicity, and developmental toxicity) studies for tr imed lure. The studies were waived based on the results of two subchronic toxicity studies (90-day oral and developmental ) used as bridging data for the safety assessment of other structurally similar pheromone products (OECD 2002), and on the demonstrated low acute toxicity oftrimedlure

. The findings of the bridged data indicated that there were no significant health effects from subchronic exposure to this group of compounds. 

### Dietary Exposure and Risk Assessment A dietary (food and drinking water) exposure and risk assessment was not conducted since the product is impregnated into a polymeric matrix dispenser that is conta ined within the trap and s l ow ly emitted over time to control fruit flies. The product is not applied directly to the agricultural commodities and is therefore limited. Based on this limited exposure, residues of trimedlure are expected to be below the Agency's level of concern for the general population and all population subgroups

. No new registration applications have been submitted since the initial registration of trimedlure , and no new risks have been id entified

. Further, due to the known low mammalian toxicity of arthropod pheromones and the low app li cation rate of end-use products , EPA has determined that dietary exposure and risk are not of concern for trimedlure. Therefore , EPA ' s conclusions as reported in the 2001 BRAD are sti ll current: any potential pesticidal residues of trimedlure in food and drinking water are anticipated to be negligible and the continued use of trimedlure as a pesti c id e does not present any concern to the Agency. 

### Food Tolerances In accordance with CFR 

### § 180.1124, arthropod pheromones , when used in retrievable sized polymeric matrix dispensers (within traps) are exempt from the requirement of a tolerance in or on all raw agricultural commodities when applied to grow in g crops only at a rate not to exceed 150 grams active ingredient (a.i.)/ acre/ year in accordance with good agri cultural practices. Therefore, all exist ing polymeric matrix dispensers products which contain the a.i. , trimedlure , and are appl ied at a rate equal to or below 150 grams a.i ./ acre / year, are exempt from the requirement of a tolerance on raw agricultural commodities. 

### Residential and Occupational Exposure and Risk The potential for exposure during application and handling of dispensers containing trimedlure is anticipated to be minimal (U.S. EPA , 2001). The end-use products may only be formu lated into polymeric-matrix removable dispensers and applied at a low rate not to exceed 150 grams active ingredient (a.i.)/ acre/ year in accordance with good agricultural practices. Dispensers typically consist of polymeric adhesive panels , wh ich conta in the olfactory attractant , trimedlure , enclosed within a paperboard trap. Traps and dispensers are commercially available as ready to use items thereby significantly limiting the potential for app li cator dermal and inhalation exposure. 6The potent ial for post-application dennal a nd inh al ati on exposure resulting from entry into treated areas is anticipated to be negligible (U
. S. EPA, 200 1). The polymeric matrix dispensers (within traps) are for use outdoors in orchards and gardens and require no additional post
- application treatment or handling other than to remo ve th em for disposal or replacement approximately every 3 to 6 weeks

. 1 At this tim e , it is highJy likely that all of th e active ingred ient will have completely dissipated. Although the r e is a remote potentia l for in c i dental non - dietary exposure to you ng children, the li keli h ood of an adverse effect is anticip ated to be very low

. The extent to which young children will be engaged with the enclosed dispenser in home gardens for prolonged periods of time is low, and significant non dietary inges tion exposure is not expec ted. Furthermore, the Agency has received no incident reports resulting from the use of pestic ida l products contai ning the active ingredient tri medlure. Therefore, EPA has concluded that occupational and residential exposures a nd ri s ks are not of conce rn. E nvironmental 

### Assessment A t the time of the first trimedlure registration, EPA conducted a qualitative environme n tal fate and effects assessment for trimedlure and determined that effects to nontarget species are unlikel y (U
. S. EPA, 2001). Trimedlur e is r egistered for usc in retrievably sized polym e ric matrix di spe n se rs enclosed within traps, w hi c h will sig nificantly lim it potential exposure t o birds, fish, non-target insects and aquatic organisms. Furthermore , its low app licati on rate wi ll limit the possibility of adverse ecological effects. As a result , environmental effects data requirements were waived; however. the registrant submitted a technical journal article 2 which tested for fre s hwater fish toxicity , gene rall y in accordance with Sub di v is ion M Guideline 1 54-8. The s tud y was accepted and reviewed by th e Agency, which concluded that trimed lure was s lightly toxic to fish

. Furthermore , the Agency has r eviewed a nd eva lu ated publicall y ava il ab le ecotoxicity data for a number of chem ica ll y si milar arthropod pheromones, and published ecotoxic i ty findings for pheromones in the Federal Register (59 FR 3681; January 26 , 1994) which conclude that pheromones are highly toxic to aquatic invertebrates and moderately toxic to fish. but practically non-toxic to birds (low toxicity to bobwh i te quaiL with an acute ora l LDs o of > 2 , 000 mg/kg of body weight and dietary LCs o of > 5.000 mg/kg). However , as noted above. because exposu r e is expec ted to be ne g ligible , EPA had detem1in ed that effects to non-target species are unlikel y. The following end-use label language has been required s inc e the product was first registered to mitigate any potential risk to aquatic organisms: " Do not discharge effluent containing this product into lakes, streams , ponds, estuaries, oceans or other waters unless in acco rdance with the req uireme nts of a National Pollutant Di sc harge Eli min ation Sys tem (NP D ES) permit and the pc rmit1ing author ity ha s been notified in writing prio r to d ischarge. D o not discharge effluent containing this product to sewer systems without previously notifying the sewage treatment plant autho rity . For guidance contact your State Water Board or Regional Office of the EPA. Do not contami nate water by cleanin g of equipme nt or disposal of waste. "

1 Trapping Guide lin es for Area-Wide Fruit Fly Pro g rams. Internation al Atomic Energy Agency. November, 2003. 2 Acut e T o xic it y Studies with Insect Auractants. M
. Bereza , et al. 19 75. Toxicology and Applied Phannacology 31:421-429 ; MRID449063-04.


### 7

### Threatened and Endangered Species There have been no r epor t s of adverse effects or incidents in nontarget organis ms exposed to trimedlure during its 14 years of pesticidal use (EPA Ecologica l In c id ent Information System version 2. 1.1 12/ 08 / 20 15). Furth ermore , based on th e type and extent of use, the low expected toxicity and low exposure predicted by the hi ghly diffuse nature of the use coupled with the target-species specificity and extr eme ly low annual usage , the Agency believes that effects on the environment are not reasonably expec ted to occur from the reg istered use of trimedlure. Therefore, the EPA anticipates making a "No Effect" determination under the Endangered Species Act (ESA) for direct and indirect effects to listed species and their habitats. 

### Endocrine Disruptor Sc re ening Program As req uire d by th e Administrator und e r the Federal Food, Drug, and Cos metic Act (FFDCA) sect ion 408(p) , the EPA has developed the Endocrine Disrupter Screening Program (EDSP) and has begun to implement the screen in g program that i s to be used to test all pesticides in order to determine whether certain substances (including pesticide active and other ingredients) may have an effect in humans or wild li fe similar to an effect produced by a "natura ll y occurr ing estrogen, or other such endocrine effects as the Administrator may des ignate." FFDCA section 408(p)(4) authorizes the Administrator , by order, to exempt from the requirements of the Estrogenic Substances Sc reeni ng Program a biologic substance o r other substance if a determination is made that the substance is not antic ipated to produce any effect in humans s imilar to an effect produced by a naturally occurring est ro gen ic substance

. Between October 2009 and February 20 I 0, the EPA issued test orders/data call- in s for the first group of 67 chemicals , which contains 58 pesticide act ive ingredi ents and 9 inert ingredients. A second list of chemicals identified for ED SP screening was published on June 14, 2013, 3 and includes some pesticides schedu led for registration review and chemicals found in water. Trimedlure is not an1ong the group of pesticide active ingredients on the li sts to be screened und er the EDSP. The EP A, as part of this Combined Work Plan, Summary Document , and Proposed Interim Registration Review Decision , believes that trimedlure is a substance that would not likely produce any effect in humans similar to an effect produced by a naturally occurring estrogenic substance. As such , pursuant to Section 408(p)(4) , the EPA will determine in the future whether it can exempt Trimedlure from the requirem e nts of the Section 408(p) EDSP. ln the event the EPA doe s determine to exempt th is s ubstance f rom the EDSP , an order w ill be issued. For further inf ormation on the status of the EDS P , the policies and procedures , the lists of chem icals , future lists , the test guide lin es and the Tier 1 screening battery , please visit our website at hllp :// ww\1'

. epa . gov l endol
.

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### 8

### COMBINE D WORK PLAN, SUMMARY DO CUMENT , AND PROPOSED INTE RIM REGISTRATION RE VIEW D EC ISIO N In acco rd ance wit h 40 CFR Sections 155.50 , 155.56, and 1 55.58, the Agency i s issuing this combined Work Pl an, Summary D ocume nt , and Proposed In te rim R eg istration Rev iew Deci s i on. Except for the ESA and EDSP components of the trimedlure re g istration review case, the Age ncy has made the following propo sed int erim decisions: (1) no additional data are required at this time: and (2) no changes to the affected registrations o r their labeling are needed at th is time. E PA has not identified any ri sks of concern to human he alth . C urrently registered uses oftrimed l ure are not expec ted to result in adverse effects to li sted or non- li sted species , or c ritical habitat

. As s uch , EPA anticipates makj ng a "No Effect" determination under the ESA for direct and indirect effects to li sted species and their habitats. 

### NEXT STEPS AND TIMELINE A Federal Register No tice will announce the availability of this combined Work Plan and Summary D ocument and Proposed Inter im Registration Review D ecis ion for trimedlure and allow a 60

-day comment period. If there are no s ignificant comments o r addi ti onal information submitte d to the docket during the comment period that leads the Age nc y to change its propo sed decision, EPA m ay iss ue an In terim Regi stration Review Decision for tri med lure (case 6045) , in accordance with 40 CFR Sec tions 155.56 and 155.58. A final decision on th e trimedlure reg istrat ion review case will a lso occur after an EDS P FF DC A secti on 408(p) determination h as been made and an ESA de termination has been made. EP A ha s created the following estimated timeline for the completion of trimedlure registration r eview: 

### Registration Review for Trimedlure - Projected Registration Revi ew Timeline Activities Es timated D ate Opening the Docket and Combined Work Plan, S ummary Docum ent, and Interim Regi stration Review Decision Open Public D ocket and Public Comment Pe ri od for Co mbined Work December 2015 Plan , Summary D ocument, and Proposed Interim Registration Review Decision Close Public Comment Period Feb ruary 2016 

### Interim and Final Registration Review Deci s i o n s Interi m Regi stration Rev iew D ecision June 2016 Final D ecis i on (est im ated) 4 D ecember 20 16 Total (years) 1 year, 0 months

4 A final decision on the trim edlure registration review case, in accordance with 40 CF R Section 155.158, will occur after an EDS P FFDCA section 408(p) determination has been made and an ESA determination has been made. 

### 9

### Referenc es: This docum e nt s ummari zes th e Environmental Protection Agency's current position based on th e following documents: 

### 1. U.S. E PA , 2001. 4-(or 5) Chloro-2-Methylcyclohexanecarboxlic Acid , I , !-Dimethyl E s t e r (Trimedlure) Biopesticides Registrat ion Action Document. U.S
. Envi ronmental Protection Agency. July 26 , 2001. Availab l e at: http: // www3 .epa.gov / p es ticides/ chem

_ sea rch/reg

_ actions/ registration/deci s ion

_ P C112603 _26 -Jul

- 0 l.pd f#_ga = 1.136704888 .9519 8873 1 .1440526185 2 . IAEA , 2003. T rapp i ng Guidelines for Area -Wide Fruit Fly Programmes , International Atomic E nergy Age nc y. November , 2003. Available at: htt p ://www pub

. iaca . o rg/ M TC D / pu b li cati o n s/ PDf /TG

- FFP wcb

. pdf 3. O EC D , 2002. Organization for Econom ic Co-operat ion and Development ( OECD) Guidance for Re g i s tration Requirem e nt s for Pheromo ne s and Other Semiochemicals Used for Arthropod Pes t Co ntrol. February 26. 2002

. Available at: hn p ://wW\v

. oecd

. org/ offic ia ld ocume nts /public di s p lavdocu m ent p dfl?co te = env/jrn/ m o no(20 0 1 ) 12&doclanguage = c n

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### A pp e ndix - Additi o n a l Ar e as Co n s idered in the T rimedlur e Reg i s tr at i o n Rev iew 

### PUB LI C C O M MEN T S A ND FEE DB AC K : G uid a nc e fo r C om mente rs: The areas be l ow highl i ght topics of special interest to the Agency where your comments , data submiss ions , or refere nce to sources of additional information could be of particular use . 

### Trad e Irritants: Through the registration review process , the Agency intends to solicit information on trade irritants and, to the extent feasible, take steps toward facilitating irritant reso l uti on . The Agency will work to harmonize tole rances and i nternational maximum residue li mits (MRLs) and may modify tolerance leve ls to do so, when possible. 

### G row ers and o th e r s takeholders a re as ked t o comm e nt on any trade irritant issues res u lti ng from lack of MRLs or disparit ies between U.S. tolerances and MRLs in key export markets, providing as much spec i fic ity as possible regarding the nature of the concern . Although its registe red pestic idal uses are non - food, should trimedlure inadvertently occur in food or feed commodities 

### ( e.g. through spray drift to c rops grown adjacent to treated fields) , this act ive ingredient is exempt from the requirement of a to lerance for arthropod pheromones when applied i n a retrievable d ev ice per 40 CFR part 180.1124. Moreover , there are no known MRLs for trimedlure. Therefore , the EPA does not ant ic ipate that current uses of tri medlure will pose concerns as trade irritants. 

### Water Qualit y: Trimedlure is not ident ified as a cause of impairment for any water bod i es li sted as impaired under sect ion 303(d) of the Clean Water Act. 5 

### In add i ti on , no Total Maximum Daily Loads (TMDL) have been developed for trimedlure. 6 

### More infonnation on impaired water bodies and TMDLs can be found at the Agency's webs i te. 7 

### Th e Ag ency invites submi s sion o f wat e r quality d a ta for t hi s p es ti cid e. To the extent poss i ble , data should conform to the q uality standards in Append i x A of t he 

### OPP Standard Operating Procedur e: Inclusion of Impaired Water Body and Other Water Quality Data in OPP 's Registration Review Risk Assessment and Management Process 8 

### in order to ensure they can be used quantitatively or qualitatively in pestic i de risk assessments. 

### Environmental Justice: EPA seeks to ach ieve environmental justice , the fa ir treatment and meaningful i nvo lvement of all people, regardless of race , color, national origin, or income, in the development , implementation , and enforcement of environmental laws, regu lations , and policies.

5 hnp: // ia s pub .e pa . gov/ tmdl wat e rs I0/attain s nation c v .cau s e detail JOJd ? p cause group id = 885 6 hnp ://ia s pub

. epa . gov /tmdl wat e r s I0 / attain s nation.tmdl pollutant detail ? p pollutant group id = 885&p pollu tant !!roup name = PESTICIDES 7 http ://www . epa . gov/owow / tmdl / 8 http ://www . epa . gov/ oppsrrd ! / registration review/ water quality s op . htm 

### 11

### To help address potential environmen tal justice issues , the Agency seeks infonnation on any groups or segments of the population who , as a result of their location , cu ltural practices, or other factors, may have atyp ical, unusually high exposure to trimedlure compared to the ge neral population. P l eas e c omm e nt i f yo u are a ware o f a n y s ub-population s th at m ay h ave a ty pic a l , unu s u a lly hi g h ex po s ur e comp a red t o th e ge n e r a l populati o n .

12