OFFICE OF CHEMICAL SAFETY
AND POLLUTION PREVENTION 

### UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON

, D.C. 20460

June 17, 2014

PC Code: 128724

MEMORANDUM DP Barcode: 409810

Subject: Preliminary Ecological Risk Assessme nt for the Registration Review of Flumiclorac-pentyl

From: N.E. Federoff, Wildlife Biologist Greg Orrick, Environmental Scientist

Environmental Risk Branch 2

Environmental Fate and Effects Division

Through: James Lin, Environmental Engineer Kristina Garber M.S., Senior Biologist Jean Holmes, DVM, MPH, Risk Assessment Process Leader Brian Anderson, Branch Chief

Environmental Risk Branch 2

Environmental Fate and Effects Division

To: Eric Miederhoff, Ch emical Review Manager Patricia Parrott, Branch Chief Risk Management and Implementation Branch 3

Pesticide Re-evaluation Division

The Environmental Fate and Effects Division (E FED) has completed the (attached) ecological risk assessment to be conducted as part of the Re gistration Review of the herbicide, flumicloracpentyl (PC Code 128724). Based on currently registered uses and la beled rates, this preliminary assessment is focused on species that are not fe derally listed as threatened or endangered (referred to as “listed). For taxa where there ma y be risks of concern, specific determinations for listed species are considered uncertain at this time. Currently labeled rate s of flumiclorac-pentyl pose a potential for direct adverse effects , (i.e ., risk) to non-target listed dicot terrestrial plants as well as listed and non-listed fish and aquatic phase amphibians (due to a lack of data). The model AgDRIFT was used to calculate the distan ce from treated fields for which spray drift exposure to terrestrial plants is below the toxici ty thresholds for listed plant species. For a ground application, effects to plants could occur up to 509 feet from application sites. For aerial application, effects could occur up to 876 feet from the applicati on site. In general, AgDRIFT

distance estimations are a ffected by application rates, number of annual applica tions, application methods ( i.e. , ground versus aerial), buffers , and spray droplet size.

### 2 of 87 Attachment: The Environmental Fate, Ecological Risk, and Endangered Species Assessment in Support of the Registration Revi ew of Flumiclorac-pentyl.

### 3 of 87 

# Preliminary Environmental Fate and Ecological Risk Assessment in Support of the Registration Review of Flumiclorac-pentyl

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Flumiclorac-pentyl (CAS 87546-18-7)

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repared by:



### N .E. Federoff, Wildlife Biologist Greg Orrick, Environmental Scientist U. S. Environmental Protection Agency Office of Pesticide Programs

E nvironmental Fate and Effects Division

E nvironmental Risk Branch II 1200 Pennsylvania Ave., NW

M

ail Code 7507P Washington, DC 20460 R eviewed by: 

### James Lin, Environmental Engineer Kristina Garber M.S., Senior Biologist Jean Holmes, DVM, MPH, RAPL Brian Anderson, Branch Chief

### 4 of 87 Table of Contents

1. EXECUTIVE SUMMARY .................................................................................................... 7

1.1. Purpose of Assessment ..................................................................................................... 7

1.2. Nature of the Stressor ....................................................................................................... 7

1.3. Environmental Fate Summary .......................................................................................... 7

1.4. Summary of Effects and Risk Conclusions ...................................................................... 7

2. PROBLEM FORMULATION ............................................................................................... 8

2.1. Pesticide Type, Class, and Mode of Action ..................................................................... 8

2.2. Stressor Source and Distribution ...................................................................................... 8

2.3. Nature of Regulatory Action .......................................................................................... 12

2.4. Previous Risk Assessments ............................................................................................ 12

2.5. Ecosystems Potentially at Risk ...................................................................................... 12

2.6. Assessment Endpoints .................................................................................................... 13

2.7. Receptors ..................................................................................................................... ... 13

2.8. Risk Hypothesis.............................................................................................................. 1 3

2.9. Stressors of Concern....................................................................................................... 14

2.10. Measures of Exposure ................................................................................................ 15

2.11. Measures of Effect ...................................................................................................... 16

3. ANALYSIS ...................................................................................................................... ..... 17

3.1. Environmental Fate and Transport ................................................................................. 17

3.1.1 Residues of Concern ............................................................................................... 28

3.2. Aquatic Exposure ........................................................................................................... 29

3.2.1 Bioaccumulation ..................................................................................................... 31

3.2.2 Monitoring Data ...................................................................................................... 31

3.3. Terrestrial Exposure ....................................................................................................... 32

3.4. Effects Characterization ................................................................................................. 32

3.4.1 Effects to Aquatic Organisms ................................................................................. 32

3.4.2 Effects to Terrestrial Organisms ............................................................................. 35

4. RISK CHARACTERIZATION ............................................................................................ 37

4.1. Terrestrial Environment ................................................................................................. 37

4.1.1 Avian and Mammalian Dietary Residues ............................................................... 37

4.1.2 Avian & Mammalian Exposure From Drinking Water .......................................... 40

4.1.3 Terrestrial Plants ..................................................................................................... 41

4.1.4 Beneficial insects .................................................................................................... 42

4.2. Aquatic Environment ..................................................................................................... 42

4.3. Incident Database Review .............................................................................................. 43

4.4. Endocrine Disruptor Screening Program ....................................................................... 43

4.5. Risk Description ............................................................................................................. 44

4.5.1 Terrestrial Environment .......................................................................................... 44

4.5.2 Aquatic Environment .............................................................................................. 45

4.5.3 Endangered Species Assessment ............................................................................ 46

5. DATA GAPS ..................................................................................................................... ... 48

5.1. Fate .......................................................................................................................... ....... 48

5.2. Effects ....................................................................................................................... ...... 49

6. REFERENCES .................................................................................................................... . 50

### 5 of 87 6.1. Open Literature .............................................................................................................. 50

6.2. Submitted Environmental Fate and Product Chemistry Studies .................................... 52

6.3. Submitted Effects Studies .............................................................................................. 55

List of Tables

Table 1. Maximum use patterns for curre nt uses of flumiclorac-pentyl ( i.e. , flumiclorac pentyl ester) ........................................................................................................................ ........................ 9

Table 2. Screening-level estimates of agri cultural uses of flum iclorac-pentyl ............................. 10

Table 3. Chemical Properties and Environmental Fate Parameters of Flumiclorac-pentyl .......... 18

Table 4. Environmental Fate Parameters of Degradates of Flumiclorac-pentyl ........................... 20

Table 5. Flumiclorac-pentyl and Its Environmental Degradates A 

### ............................................... 23

Table 6. Environmental Fate Parameters of Flumiclorac-pentyl Residues of Concern ................ 28

Table 7. PE Chemical Input Parameters for Flumiclorac-pentyl Re sidues of Concern ................ 29

Table 8. PRZM Scenarios and Input Parameters Describing Maximum Patterns of Flumicloracpentyl Use on Representative Use Sites........................................................................................ 30

Table 9. Aquatic Exposure Estimates fr om Flumiclorac-pentyl Use Sites A 

### ................................ 31

Table 10. Summary of sensitive endpoints for aquatic organisms under consideration for use in the risk assessment for flumiclorac-pentyl* ................................................................................. 3 4

Table 11. Summary of sensitive toxicity endpoints for terrestrial organisms under consideration

for use in risk assessment* ................................................................................................... ......... 36

Table 12. Estimated environmental concentrations (dietary-based) and RQs of flumiclorac-pentyl on avian food items (Kenaga Values). Based on LC50 of >5322 ppm and NOAEC of 220 ppm

............................................................................................................................... ........................ 38

Table 13. Estimated environmental concentrations (dietary-based) and RQs of flumiclorac-pentyl on avian food items (Kenaga Values). Based on LC50 of >5322 ppm and NOAEC of 220 ppm. A 35 day default halflife was used. ........................................................................................... .... 39

Table 14. Estimated environmental concentrations (dietary-based) and RQs of flumiclorac-pentyl on mammalian food items (Kenaga Values). Ba sed on rat LD50 of >5000 ppm and reproductive NOAEC of 200 ppm. ............................................................................................................. ....... 39

Table 15. Dose-based Avian and Mammalian EECs ( 0.081 lbs ai/A x 2 applic ations at a 14 day interval) ..................................................................................................................... .................... 39

Table 16. Dose-based Avian RQs (0.081 lbs ai/A x 2 applications at a 14 day interval) ............. 40

Table 17. Dose-based Mammalian RQs (0.081 lbs ai/A x 2 applications at a 14 da interval) ..... 40

Table 18. Mammalian Results ................................................................................................... ... 40

Table 19. Avian Results ....................................................................................................... ......... 41

Table 20. Acute RQs for listed terrestrial plants ........................................................................... 4 1

Table 21. Acute and chronic RQs for fish, a quatic invertebrates & aquatic plants ...................... 42

### 6 of 87 Table 22. Submitted Environmental Fate Data for Flumiclorac-pentyl ....................................... 48

Table 23. Submitted Environmental Fate Data fo r Degradates of Flumiclorac-pentyl ................ 49

Appendices

Appendix A. Summary of Toxicity Data 63

Appendix B. Memorandum: Request for Photot oxicity Study Protocol for Light-Dependent Peroxidizing Herbicides 70

Appendix C. Aquatic Model Calculations 76

Appendix D. ECOTOX 77

Appendix E. ECOSAR Estimates 84

### 7 of 87 1. EXECUTIVE SUMMARY

1.1. Purpose of Assessment

The purpose of this assessment is to evaluate the potential risks of flumiclorac-pentyl’s registered uses on non-target organisms. This assessment is focused on non-listed species and does not fully consider risks to federally listed endangered and threatened (listed) species. For taxa where there may be risk, specific determina tions for listed species are considered uncertain at this time. This risk assessment incorporates the available exposure a nd effects data and most current modeling and risk methodologies, some of which may not have been available at the time previous risk assessments were conducted.

1.2. Nature of the Stressor

Flumiclorac-pentyl is an N-phenylphthalimid e derivative herbicide and a light-dependent peroxidizing herbicide (LDPH), meaning it may be more toxic under higher light intensity. In agricultural settings, this chemical is registered for post-emergence application to field corn and soybeans, as a defoliant on cotton, and as a Sp ring burndown herbicide. For non-agricultural use sites (including golf courses, park s, recreational areas, residential areas, schools, Christmas tree farms, sod farms, ornamental nurseries, indus trial areas, commercial areas, rights-of-way, and habitat restoration and maintenance areas), it is re gistered for control of broadleaf weeds. The compound’s six major degradates with an intact imido/amide bridge (IMCA (flumiclorac acid), 031-HA, IMCA-HA, IMFP, IMFP-HA, and SAT IM FP-HA) are assumed to have toxicity similar to the parent compound and ar e included as residues of concern.

1.3. Environmental Fate Summary

Flumiclorac-pentyl ( i.e. , flumiclorac pentyl ester) rapidl y degrades to flumiclorac acid ( i.e.

, IMCA) and 031-HA, both of which further degrade to a suite of 12 additional (14 total) major degradates, most of which are not persistent. Flumiclorac-pentyl re adily hydrolyzes in the presence of moisture, especially in alkaline conditions (hydrolysis half-lives of 12 minutes at pH 9, 18 hours at pH 7, and 4.5 days at pH 5). The compound biodegrades in soil with DT 50 

### values of 7.3-11 days and does not photolyze. In the field, flumiclorac-pentyl dissipates with DT 50 

### values less than 2-5 days. The mobility in soil of the parent compound is unknown due to its instability in the presence of moisture. Fl umiclorac acid is mobile in soil, with K OC 

### values of 34- 100 L/kg OC 

### . Collectively, the flumiclorac-pentyl resi dues of concern are m oderately persistent, with collective biodegradation half-lives of 25-59 days. Major transport r outes for the residues of concern include spray drift and runoff and exclude volatilization.

1.4. Summary of Effects and Risk Conclusions

The major risk concern for flumiclorac-pentyl is for decreases in grow th of listed non-target dicot plants. This conclusion is expected since the chemical is registered as an herbicide. Exposure resulting from spray drift poses a ri sk concern. The model AgDRIFT was used to calculate the spray drift buffers n eeded to reduce terres trial plant exposure to below the toxicity thresholds for listed plant species. For a ground application, the listed plant buffer is 509 feet. For aerial applicati on, the calculated buf fer is 876 feet.

### 8 of 87 Major uncertainty exists due to a lack of chronic toxicity data fo r fish and expected increases in sensitivity of these species because flumiclora c-pentyl is a light-dependent peroxidizing

herbicide.

Risk of effects to survival, growth and re production are not expected for mammals, birds, terrestrial-phase amphibians, rept iles, and aquatic invertebrates.

Mortality is not expected for e xposed fish. Growth effects are not expected for aquatic plants.

Mortality is not expected for hone y bees directly sprayed with the chemical; however, data are unavailable to determine the oral toxicity of this chemical to bees.

2. PROBLEM FORMULATION

The problem formulation for this assessment discu sses the stressor, the c onceptual models used to estimate exposures to non-target organisms, and the tools and methods with which EPA will assess potential risk. It is based on the Preliminary Problem Formulation for the Registration Review of Flumiclorac-pentyl (DP barcode 362087), which was completed July 10, 2009. The following sections reiterate the salient info rmation from the 2009 Problem Formulation and indicate any new data or assessment methods that may have changed since it was prepared.

2.1. Pesticide Type, Class, and Mode of Action

Flumiclorac-pentyl is a N-phenylphthalimide deri vative herbicide used for the control of broadleaf weeds. Flumioxazin is the only other such herbicide registered for use in the United States. Flumiclorac-pentyl’s mode of acti on, as a light-dependent peroxidizing herbicide (LDPH), is through the accumulation of porphyrin s in susceptible plants. In turn, the photosensitizing action of accumu lated porphyrins may cause membrane lipid peroxidation

which leads to irreversible dama ge of membrane function and stru cture in the target plant. Porphyrins accumulate because LDPH chemicals inhibit the enzyme protoporphyrinogen oxidase (protox), which is the last common enzyme in the heme and chlorophyll biosynthetic pathways (Matringe et al. , 1989). Protox exists in both plants a nd animals and the enzyme from both sources has been shown to be highly sensit ive to many LDPHs (Birch field and Casida, 1997).

2.2. Stressor Source and Distribution

Flumiclorac-pentyl is register ed for post-emergence broadcast application to field corn and soybeans, as a defoliant on cotton, and as a Sp ring burndown herbicide. For non-agricultural use sites (including golf courses, park s, recreational areas, residential areas, schools, Christmas tree farms, sod farms, ornamental nurseries, indus trial areas, commercial areas, rights-of-way, and habitat restoration and maintenance areas), it is registered for contro l of broadleaf weeds including morning glory and velvet leaf. Th e registered formulations include soluble concentrate, dust, wettable powder, granular, liq uid, and pelleted or tableted (BEAD, August, 2008). Table 1 contains the labeled use pa tterns of maximum exposure.9 of 87Table 1. Maximum use patterns for current uses of flumiclorac-pentyl (i.e., flumiclorac pentyl ester)Product Label(EPA Reg. No.);FormulationActive Ingredient(%)Use SiteMax. SingleApp. Rate(lbs a.i./A)Max. AnnualApp. Rate(lbs a.i./A)AApp.Interval(d)ApplicationTypeAdditional ApplicationDirectionsResource(59639-82);EmulsifiableConcentrateFlumiclorac pentylester (10.1% by wt.)Field corn0.0400.05414Aerial orgroundAerial applications may notexceed 0.054 lbs a.i./A.Do not apply by any irrigationsystem. Produce medium, notfine, spray droplet sizes.Soybeans0.0810.11Spring burndownB[proposed use directionsC]0.027[0.081C]Not stated[0.11C]Not stated[7C]Cotton0.0540.0947GroundStellar(59639-92);EmulsifiableConcentrateFlumiclorac pentylester (7.6% by wt.)and lactofen (26.6%by wt.)Soybeans 0.038 0.055 14 GroundDo not apply by air or by anyirrigation system.Resource 80 WP(59639-100);Wettable PowderFlumiclorac pentylester (80% by wt.)Field corn0.0540.05414GroundDo not apply by air or by anyirrigation system.Soybeans0.0810.11V-10097(59639-122);EmulsifiableConcentrateFlumiclorac pentylester (0.576% bywt.) and glyphosate(40.700% by wt.)Field corn0.0140.02814Aerial orgroundDo not apply by any irrigationsystem.Cut stump treatments may bemade on any site listed on thislabel.Do not apply directly to or overornamentals.Soybeans0.0420.042Spring burndownB[proposed use directionsC]0.028Not stated[0.056C]Not stated[7C]Golf courses, parks, recreationalareas, residential areas, schools,Christmas tree farms, sod farms,ornamental nurseries, industrialareas, commercial areas, rightsof-way, habitat restoration andmaintenance areas[proposed use directionsC]0.028Not stated[0.056C]Not stated[7C]ALabels provide seasonal application rate limits that approximate annual limits.BSpring burndown uses may occur prior to or immediately after planting cotton, field corn, or soybeans.CProposed [bracketed and footnoted] label directions are intended for the next stamped label. The current label directions are not bracketed.

### 10 of 87 The herbicide was first registered in 1994. There are a total of five FIFR A Section 3 labels, one technical product and the four end-use products listed in Table 1 . All labels are registered by Valent USA Corp. In addition, there is one E xperimental Use Permit (EUP) and a Special Local Need (SLN) label that was issu ed to the State of Missouri.

Flumiclorac-pentyl is applied via aircraft, gr ound spray, back pack sprayer, ground boom, hand held, and band sprayer at various application rates depending on the application method, crop, and applicable label. The end-use products cont aining flumiclorac-pentyl have a wide range of active ingredient concentrations ra nging from 0.576% ai to 80.0% ai.

Table 2 provides estimates of the na tional-level agricultural usage of flumiclorac-pentyl from 2001 to 2007 (provided by the Biolog ical and Economic Analysis Di vision in OPP (BEAD)). Most usage was on soybeans. The uses marked w ith the “+” symbol represent crops that were

not known to be listed on active end use product registrations when this report was run. The lbs A.I. values listed in the table are average a pplication amounts that span over a 7 year period (2001 to 2007). As a result, cancel led uses may appear in the tabl e. Note that non-agricultural usage data are not listed because they are not available.

Table 2. Screening-level estimates of agricultural uses of flumiclorac-pentyl Crop Lbs. A.I. Percent Crop Treated Avg. Max.

1 Corn 1,000 <1 <2.5

2 Cotton 1,000 <1 <2.5

3 Potatoes + <500 <1 <2.5

4 Rice + <500 <1 <2.5
5 Soybeans 10,000 <1 <2.5

All numbers rounded. '<2.5' indicates less than 2.5 percen t of crop is treated.
'<1' indicates less than 1 percent of crop is treated



### . + = These crops were not known to be listed on active end use product registrations when this report was run.

SLUA data sources include:

USDA-NASS (United States Department of Agriculture's National Agricultural Statistics Service); 2001-2007

Private Pesticide Market Research, 2001-2007 NPUD 2002 (National Pesticide Use Database of the CropLife America Foundation)

California DPR



### Figure 1 displays the agricultural usage of flumic lorac-pentyl in 2011, as reported by the USGS NAWQA program (USGS, 2014). Soybeans are consis tently the use site with highest usage.

### 11 of 87 Figure 1. Agricultural usage of flum iclorac-pentyl in 2011 (USGS, 2014)

### 12 of 87 2.3. Nature of Regulatory Action

Under the Federal Insecticide, F ungicide, and Rodenticide Act (FIF RA), all pesticid es distributed or sold in the United States must be registered or approved by the United States Environmental Protection Agency (EPA). To determine whether a pesticide can be regist ered, EPA evaluates its safety to non-target species based on a wide rang e of environmental and health effects studies. In 1996, FIFRA was amended by the Food Quality Protection Act, and EPA was mandated to implement a new program for the periodic review of pesticides, i.e ., registration review 1 

### . The Registration Review program is intended to ensure that, as the ability to assess risk evolves and as policies and practices change, al l registered pesticides continue to meet the statutory standard

of no unreasonable adverse effects to human health and the environment. Changes in science, public policy, and pesticide use practices will occur over time. Through the new registration review program, the Agency periodically reevalua tes pesticides to make sure that as change occurs, products in the market place can be used safely.

As part of the implementation of the Registratio n Review program pursuant to Section 3(g) of FIFRA, EPA is evaluating the use of flumiclor ac-pentyl to determine whether it continues to meet the FIFRA standard for registration.

2.4. Previous Risk Assessments

The risk assessments available in the docket whic h serve as the basis for this preliminary risk assessment include the following:

 October 31, 2005 EFED Risk Assessment fo r the Proposed New Use of Flumicloracpentyl on Cotton, DP 311964 (US EPA, 2005a)

 March 14, 1994 EEB Hazard Assessment Science Chapter V-23031, DP 165814+

The conclusion of the 2005 risk assessment was that adverse risk to listed and non-listed terrestrial dicot plants is expected.

2.5. Ecosystems Potentially at Risk

The ecosystems at risk are often extensive in scop e; therefore, it may not be possible to identify specific ecosystems during the development of a nation-wide ecological risk assessment. However, in general terms, terrestrial ecosystems potentially at risk could include the areas that are immediately adjacent to treated areas that ma y receive drift or runoff during flooding. Areas adjacent to the treated areas could include cultiv ated fields, fencerows and hedgerows, meadows, fallow fields or grasslands, woodlands, ripari an habitats and other uncultivated areas.

Aquatic ecosystems potentially at risk include wa ter bodies adjacent to or downstream from, the treated areas and could include impounded bodies such as ponds, lakes and reservoirs, or flowing

1 http://www.epa.gov/oppsrrd1/registration_review/

### 13 of 87 waterways such as streams or rivers. For uses in coastal areas, aquati c habitat also includes marine ecosystems, including estuaries.

2.6. Assessment Endpoints

Assessment endpoints represent the ac tual environmental value that is to be protected, defined by an ecological entity (species, community, or other entity) and its attribute or characteristics (U.S. EPA 1998). For flumiclorac-pentyl, the ecologica l entities may include the following: birds, mammals, terrestrial-phase amphibian s, reptiles, freshwater fish a nd invertebrates, aquatic-phase amphibians, estuarine/marine fish and invertebrates, terrestrial plants, inse cts, and aquatic plants and algae. The attributes evaluated for each of these entities may include growth, reproduction,

and survival.

2.7. Receptors

The receptor is the biological entity that is e xposed to the stressor (U.S . EPA 1998). Consistent with the process described in the Overview Do cument (U.S. EPA 2004), the risk assessment for flumiclorac-pentyl relies on a surrogate species approach. Toxicological data generated from surrogate test species, which are intended to be representative of br oad taxonomic groups, are used to extrapolate to potential effects on a vari ety of species (receptor s) included under these taxonomic groupings.

Acute and chronic toxicity data from studies submitted by pesticide registrants along with the available open literature are used to evaluate the potential direct and indirect effects of flumiclorac-pentyl to aquatic and terrestrial rece ptors. Additional studies, including toxicity on the technical grade active ingredient, degradates , and when available, formulated products ( e.g. , “Six-Pack” studies). The open literature studies are identif ied through EPA’s ECOTOXicology (ECOTOX) database (U.S. EPA 2009), which empl oys a literature search engine for locating chemical toxicity data for aquatic life, terrestr ial plants, and wildlife. The evaluation of both sources of data may also provide insight into the direct and indirect effects of flumiclorac-pentyl on biotic communities from loss of species that are sensitive to the chemical and from changes in

structure and functional characteri stics of the affected communiti es. Open literature citations from ECOTOX on flumiclorac-pentyl were revi ewed and were found to contain no acceptable

studies for inclusion in the ri sk assessment at this time.

A summary of the aquatic and terrest rial toxicity data used to de rive a preliminary evaluation of risk for flumiclorac-pentyl is provided in Section 3.4. In addition, a summary of ecological incidents associated with flumiclorac-pentyl a nd a description of ecosyst ems potentially at risk are provided in Sections 4.3 and 4.5, respectively.

2.8. Risk Hypothesis

A risk hypothesis describes the predicted re lationship among the stre ssor, exposure, and assessment endpoint response along with the rati onale for their selection. For flumicloracpentyl, the following overall ecologi cal risk hypothesis is being em ployed for this ecological risk

assessment:

### 14 of 87 Based on the application methods, m ode of action, fate and transport, and the sensitivity of nontarget aquatic and terrestrial sp ecies, flumiclorac-pentyl and it s six major degradates with an intact imido/amide bridge (IMCA (flumiclor ac acid), 031-HA, IMCA-HA, IMFP, IMFP-HA, and SAT IMFP-HA) have the potential to reduce surviv al and growth in non-targ et terrestrial plants

when used in accordance with the current labe l. These non-target organisms include Federally listed threatened and endangered species as well as non-listed species. Based on flumicloracpentyl’s mode of action (light dependent pero xidizing herbicide), and known sensitivity of nontarget aquatic and terrestrial spec ies to this class of chemical s, flumiclorac-pentyl and its six major degradates with an intact imido/amide bridge have the potential to reduce survival, growth and reproduction of non-targ et aquatic and terrestrial animals.

The specific exposure routes quantitatively evalua ted include water concentrations resulting from and runoff and spray drift and consumption of plan ts and invertebrates directly on the treated field by non-target terrestria l wildlife. The following hypotheses reflect these exposure pathways.

 Flumiclorac-pentyl residue of concern con centrations in water may affect aquatic vertebrates, inverteb rates, and plants.

 Flumiclorac-pentyl residues on plants and ot her dietary surfaces deposited with spray drift may affect terrestrial organisms, and r unoff of the residues of concern may affect terrestrial plants duri ng seedling emergence.

2.9. Stressors of Concern

Toxicity data have not been submitted for degradates of flumiclorac-pentyl other than for its acid, IMCA. Degradates with a cleaved imido/amid e bridge, such as the phthalic acids, are not structurally similar to and are expected to be much less toxic relative to the parent compound. Degradates with an intact imi do/amide bridge are too structural ly similar to the parent compound to expect differential toxicity with an adequate measure of certainty. Th erefore, in the absence of toxicity data, the six major degradates with an intact imido/amide bridge (IMCA (flumiclorac acid), 031-HA, IMCA-HA, IMFP, IMFP-HA, and SA T IMFP-HA) are assumed to have toxicity similar to the parent compound a nd are included as residues of c oncern for the assessed taxa.

It is uncertain whether the degr adates of concern are herbicidal . Flumiclorac-pentyl tends to rapidly degrade to acid derivativ es including the structurally sim ilar degradates of concern. In many cases, this indicates that the acid deriva tives are herbicidal. However, cell membrane disrupting herbicides such as flumiclorac-pent yl tend to require folia r contact and a lipophilic chemical structure in order to sorb through the waxy leaf cuticle (K-State Research and Extension, 2013; OSU Extension, undated). Degrad ates of concern other than 031-HA are likely to have reduced herbicidal activity because th ey are less lipophilic than flumiclorac-pentyl.

In its ecological risk assessments, the Agency does not routinely include an evaluation of mixtures of active ingredients, either those mi xtures of multiple activ e ingredients in product formulations or those in the applicator’s tank. In the case of the product formulations of active ingredients (that is, a registered product containing more than one active ingredient), each active ingredient is subject to an indi vidual risk assessment for regula tory decision regarding the active

### 15 of 87 ingredient on a particular use site. If eff ects data are available for a formulated product containing more than one active ingredient, the da ta may be used qualitatively or quantitatively in accordance with the Agency’s Overview Document and the Services’ Evaluation Memorandum (U.S. EPA 2004; U.S. FWS/NMFS 2004).

2.10. Measures of Exposure

In order to estimate risks of flumiclorac-pentyl exposures in aquatic and terrestrial environments, all exposure modeling and resul ting risk conclusions are based on maximum application rates for flumiclorac-pentyl. Measures of exposure ar e based on aquatic and terrestrial models that predict estimated environmental concentrations of flumiclorac-pentyl using maximum labeled application rates and methods, as well as any m itigation measures specif ically indicated on the label ( e.g. spray drift buffers).

PRZM and EXAMS are screening simulation mode ls coupled with the input shell PE5 (Nov. 15, 2006) to generate daily exposures and 1-in-10 ye ar EECs of flumiclorac- pentyl residues of concern that may occur in surface water bodie s adjacent to application sites receiving flumiclorac-pentyl through runoff and spray drif t. PRZM simulates pesticide application,

movement and transformation on an agricultural field as well as off-site pesticide loadings via runoff, erosion and spray drift. EXAMS simula tes the fate of the pesticide and resulting concentrations in a receiving wa ter body. The standard scenario used for ecological pesticide assessments assumes application to a 10-hectare ag ricultural field that drains into an adjacent 1- hectare water body that is 2 meters deep (20,000 m 3 

### volume) with no outlet. PRZM/EXAMS is used to estimate screening-level exposure of aquatic organisms to flumiclorac-pentyl. The measure of exposure for aquatic species is the 1-in-10 year return peak or rolling mean concentration. The 1-in-10 year peak is used fo r estimating acute exposures of direct effects to aquatic organisms. The 1-in-10-year 60-day mean is used for assessing chronic exposure to fish and aquatic-phase amphibians. The 1-in-10-year 21-day mean is used for assessing aquatic invertebrate chronic exposure.

For ground and aerial spray applications, the T-REX model (Terrestrial Residue EXposure model) is used to predict dietary exposure to flumiclorac-pentyl residues on foliar surfaces and insects using the Kenaga nomogram as modifi ed by Fletcher (Hoerg er and Kenaga 1972;

Fletcher et al. 1994). Exposure estimates for terrestrial an imals assumed to be in the target area or in an area exposed to spray drift are derived using the T-REX model. This model incorporates the Kenaga nomograph, as modified by Fletcher et al. (1994), which is base d on a large set of actual field residue data. The upper limit values from the nomograph represent the upper bound

residue values from actual field measurements (Hoerger and Kenega 1972). The Fletcher et al. (1994) modifications to the Ke nega nomograph are based on m easured field residues from 249 published research papers, including informati on on 118 species of plants, 121 pesticides, and 17

chemical classes.

Estimated Environmental Concentrations (EECs) for terrestrial plants inhabiting dry and wetland areas are derived using TerrPlant. This model uses estimates of pesticides in runoff and in spray drift to calculate EECs. EECs are based upon solubility, application rate and minimum incorporation depth.

### 16 of 87 The AgDRIFT spray drift model is used to assess exposures of terrestrial plants to flumicloracpentyl deposited on terrestria l habitats by spray drift.

2.11. Measures of Effect

Ecological effects data are used as measures of di rect and indirect effects to biological receptors. Data are obtained from registrant-submitted studies or from literature studies identified by ECOTOX. The ECOTOX database (U.S. EPA 2009) pr ovides more ecological effects data in an attempt to bridge existing data gaps. ECOTOX is a source for locating single chemical toxicity data and potential chemical mixture toxicity data for aquatic life, terrestrial plants, and

wildlife. ECOTOX was created and is maintain ed by the U.S. EPA, Office of Research and Development, and the National Health and Envi ronmental Effects Research Laboratory's MidContinent Ecology Division. Based on the current s earch of flumiclorac-pentyl in the ECOTOX database, no acceptable open literature studies were found.

Information on the potential effects of flumiclorac- pentyl on non-target animals is also collected from the Ecological Incident Information System (EIIS). 2 

### The EIIS is a database containing adverse effect (typically mortalit y) reports on non-target organisms where such effects have been associated with the use of pesticides.

Where available, sublethal effects observed in both registrant-submitted and open literature studies will be evaluated qualitatively. Such effects may include behavioral changes ( e.g. , lethargy and changes in colora tion). Quantitative assessments of risks, though, are limited to those endpoints that can be di rectly linked to the Agency’s assessment endpoints of impaired survival, growth and reproduction.

The assessment of risk for direct effects to non-target organisms makes the assumption that toxicity of flumiclorac-pentyl to birds is simila r to terrestrial-phase amphi bians and reptiles. The same assumption is made for fish and aquatic-phase amphibians.

The acute measures of effect used fo r animals in this assessment are the LD 50 

### , LC 50 

### and EC 50



### . LD stands for "Lethal Dose", and LD 50 

### is the amount of a material, given all at once, that is

estimated to cause the death of 50% of the test organisms. LC st ands for “Lethal Concentration”

and LC 50 

### is the concentration of a chemical that is estimated to kill 50% of the test organisms.

EC stands for “Effective Concentration” and the EC 50 

### is the concentration of a chemical that is estimated to produce a specific effect in 50% of the test organisms. Endpoints for chronic measures of exposure for listed and non-liste d animals are the NOAEL/NOAEC and NOAEC.

NOAEL stands for “No Observed-Adverse-Effect-Level ” and refers to the hi ghest tested dose of a substance that has been reported to have no harm ful (adverse) effects on test organisms. The NOAEC ( i.e. , “No-Observed-Adverse-Effect-Concentration” ) is the highest test concentration at

which none of the observed effects were statistically different fr om the control. The NOAEC is

the No-Observed-Effects-Concentration. Fo r non-listed plants, only acute exposures are assessed ( i.e. , EC 25 

### for terrestrial plants and EC 50 

### for aquatic plants); for listed plants either the

NOAEC or EC 05 

### is used.

2 http://www.epa.gov/oppefed1/general/databasesdescription.htm#eiis

### 17 of 87 3. ANALYSIS

3.1. Environmental Fate and Transport

Flumiclorac-pentyl rapidly de grades to flumiclorac acid ( i.e. , IMCA) and 031-HA, both of which further degrade to a suite of 12 additional (14 total) major degradates, most of which are ionic and not persistent. Flumiclorac- pentyl readily hydrol yzes, especially in alkaline conditions (hydrolysis half-lives of 12 minutes at pH 9, 18 hours at pH 7, and 4.5 days at pH 5). The compound biodegrades in soil with DT 50 

### values of 7.3-11 days and does not photolyze. In the field, flumiclorac-pent yl dissipates with DT 50 

### values less than 2-5 days. The mobility in soil of the parent compound is unknown due to its instability in the presence of moisture. Flumiclorac acid is mobile in soil, with K OC 

### values of 34-100 L/kg OC 

### . Major transport routes for flumicloracpentyl residues of concern include spray drift and runoff and exclude volatilization.

Because flumiclorac-pentyl read ily hydrolyzes in the presence of moisture, its biodegradation and photolysis rates were difficult to measure. The compound is considered stable to photolysis because its degradation rates under light in the aqueous photolysis and soil photolysis studies

were not faster than in dark conditions.

Flumiclorac-pentyl’s biodegradation rates are particularly uncertaindue to hydrolysis. Degradation rates in the biodegr adation studies were bi-phasic, likely involving both hydrolytic and microbial degradation. In water, representative DT 50 

### values ranged from 1.1 to 1.7 hours in

aerobic conditions and were 3.7 hours in anaerobic conditions, all of which can be explained by hydrolysis, except that IMCA (which wasn’t found in appreciable amounts in the abiotic hydrolysis study) was formed as well as othe r hydrolytic degradates. In aerobic soil, representative DT 50 

### values were longer (7.3-11 days) than in water.

In the field, flumiclorac-pentyl dissipated with DT 50 

### values of less than 2-5 days. Quantities were uncertain because steps were not taken to st abilize flumiclorac-pentyl in storage or during analysis. Therefore, qua ntities measured often included the pe ntyl ester and its acid combined. Either way, dissipation DT 50 

### values were relatively consistent with the initial phase of the biphasic degradation pattern in the laboratory soil studies.

Flumiclorac-pentyl is less mobile in soil than its degradates (in a soil column study); however, soil-water partition coefficients ( i.e. , K d 

### values) in acidic conditions were not measured. The compound is non-volatile, soluble in wate r up to 0.189 mg/L, and oleophilic (log K OW 

### of 4.99). Flumiclorac-pentyl has no dissoci ation constants below pH 7; above pH 7 is uncertain because

measurements were not conducted due to the compound’s instability.

Flumiclorac-pentyl bioconcentrates in fish up to 372-430x and depurates by ≥ 88% in 3-14 days. The compound’s residues of con cern are not expected to bioa ccumulate because the parent compound hydrolyzes within hours to ionic degradates with K OW 

### values orders of magnitude lower than that of the parent compound, with one exception (see Table 4 ). The half-acid 031-

HA is estimated to have a K OW 

### above that of the parent co mpound; however, similar to the parent compound, it is rapidly degr aded within hours (MRID 49063001). Table 3 summarizes the chemical properties and environmental fate pa rameters of flumiclorac- pentyl (and not its acid

### 18 of 87 or other degradates). Table 6 summarizes the environmental fate parameters of the residues of

concern. Chemical structures of flumiclor ac-pentyl and its degrad ates are listed in Table 5

.

Table 3. Chemical Properties and Environmenta l Fate Parameters of Flumiclorac-pentyl

Parameter Value Source

Selected Physical/Chemical Parameters

Molecular mass (molecular formula) 423.87 g/mol (C 21 

### H 23 

### ClFNO 5 

### ) (Calculated)

Vapor pressure (22.4 °C) <1 x 10 -7 

### torr MRID 42187405

Aqueous solubility (25  C, pH 5.6) 0.189 mg/L MRID 42187405

Henry’s Law Constant (22.4 °C) <3.0 x10 -7 

### atm-m 3 

### /mol (Calculated)

Log octanol-to-water partition coefficient (log K O W 

### ) (20-21  C, pH 5.9) 4.99 MRID 42187405

Dissociation constants (pKa, pKb) None at pH ≤ 7; decomposition at pH ≥ 9 MRID 42187405

Persistence in Water

Hydrolysis half-life (25  C) pH 5: 4.5 d pH 7: 18 hrs pH 9: 12 min MRID 42169842

Aqueous photolysis half-life (25  C, pH 5) including hydrolysis 4 d MRID 42825824,

42825825 excluding hydrolysis no substantial degradation

Anaerobic aquatic

metabolism half-life (25°C, pH 6.83) including hydrolysis 3.7 hrs MRID 42825829/

42825830 excluding hydrolysis uncertain due to hydrolysis

Aerobic aquatic

metabolism half-life (25  C; pH 6.84-8.64) including hydrolysis 1.1-1.7 hrs MRID 49063001

excluding hydrolysis uncertain due to hydrolysis

Persistence in Soil

Soil photolysis halflife (25 °C, pH 6.7) including hydrolysis 30-37 hrs MRID 42825826,

42825827 excluding hydrolysis no substantial degradation

Aerobic soil

metabolism half-life (26°C; kinetics model in parentheses A 

### ) DFOP half-lives (residue proportions) 12 hrs (80%), 115 d (20%) (DFOP) 4.3 hrs (58%), 7.3 d (42%) (DFOP) MRID 42169844,

43304601

T REP 

### for modeling 11 d (IORE) 7.3 d (DFOP)

Mobility

No batch equilibrium data

Unaged column leaching Flumiclorac-pentyl is less mobile in soil than its degradates. MRID 42169848

Aged column leaching IMCA and AFCA are mobile in soil. MRID 42825832/ 42986502,

42825833/42986501

### 19 of 87 Parameter Value Source

Field Dissipation

Terrestrial field dissipation half-life <5 d (ester; Mississippi) MRID 42825836

5.5 d (ester; Iowa) MRID 42825837

1.9 d (ester plus acid; California) MRID 46563601

Field lysimeter half-life <5 d (ester; North Carolina) MRID 42825839

<5 d (ester; Kentucky) MRID 43063601

Fish Bioconcentration

Fish bioconcentration factors (steady-state, total residues); depuration rate 21-88 (edible), 837-958 (inedible), 372-430 (whole fish);

≥ 88% depuration in 3-14 days MRID 42169809/ 42825812,

42169810/ 42825813

A DFOP means “double first-order in parallel;” IORE means “indeterminate order rate equation.”



### As stated above, microbial biodegradation rates for flumiclorac-pentyl were uncertain because the compound hydrolyzes in minutes to hours at th e pH values tested. In the aerobic aquatic metabolism study (MRID 49063001; in which the water and sediment were suboxic through portions or all of the study), the pH of the water layers was mainly just below to just above pH 8. At these pH values, the degradation ob served in the study (representative DT 50 

### values of 1.1-1.7 hours) cannot be distinguished from hydrolysis, especially since the stability of the test compound during storage and anal ysis was not established.

In the anaerobic aquatic metabolism study (MRI Ds 42825829 and -30; in which a hydrosoil was studied with ultra-purifie d water rather than its associated water), pH values during the study were not reported and compound stability during an alysis was not established. The soil was pH 6.83 initially, which was similar to the pH of the Deer Creek sediment in MRID 49063001 (6.9) upon which the water pH rose above pH 8. Therefor e, the degradation observed in the anaerobic aquatic metabolism study (representative DT 50 

### value of 3.7 hours) cannot be distinguished from hydrolysis. However, the bi-phasi c degradation rates and the form ation of flumiclorac acid in the aerobic and anaerobic aquatic studies, which didn’t form in the hydrolysis study, are

indications that microbial degradation was occurring as well as hydrolysis.

Degradation rates in the aerobic soil metabolism studies (representative DT 50 

### values of 7.3-11 days; MRIDs 42169844 and 43304601) were also bi-phasi c and longer than those in the aquatic

studies. Flumiclorac acid was formed in simila r amounts (53-60% of the applied) as in the aquatic studies (41-64% of the applied), indicat ing microbial degradati on contributing to the overall degradation.

Field data indicate that flumiclorac-pentyl and its degradates do not leach substantially in the tested conditions. Although flumiclorac-pentyl de grades to compounds that are mobile in soil, these compounds appear to be short-lived in th e soil such that they degrade further before leaching a substantial distance. However, the fate of flumiclorac-pentyl re sidues at the surface is less clear. In radiolabeled lysimeter studies, ne arly 50% of the applied radioactivity appears to have dissipated to the atmosphere in the course of studies ranging from 112 to 120 days, with the fastest dissipation occurring in 14 days. This fa r exceeds the rate of mineralization reported in

### 20 of 87 the laboratory, and raises the possibility that some of the degradates may be volatilizing. This possible volatilization is based only on one study and it cannot be determined if volatilization is occurring, and if so, what degradates are contributing.

Table 4 provides the environmental fate parameters fo r degradates of flumiclorac-pentyl. There are few of these parameters available; just one study on a degradate was submitted, on the soil mobility of flumiclorac acid (MRID 42169845/49175801). KOWWIN v1.68 estimates of log

K OW 

### for degradates of flumiclorac-pentyl are also listed.

Table 4. Environmental Fate Parameters of Degradates of Flumiclorac-pentyl

Parameter Value Source

Mobility

Organic carbon-normalized soil-water partition coefficients (K OC 

### ) Flumiclorac acid: 34, 49, 72, 100 MRID 42169845/

49175801

Log octanol-to-water partition coefficient (log K OW 

### ) (SAR estimates) 031-HA: 5.49

Flumiclorac acid: 2.70

IMCA-HA: 2.65

IMFP: 1.71

IMFP-HA: 3.07

SAT IMFP-HA: 2.00 KOWWIN v1.68



### The study author initially considered MRID 42169845 a failure because the test compound degraded with a half-life of 18 hours. Rather than conduct a new study in acidic conditions, the registrant opted to submit data from the initial st udy that were not provide d in the initial report (MRID 49175801) and that supported the calculation of soil-water partition coefficients ( i.e. , K d 

### values). K d 

### values following 2 hours of equilibration we re used, although equilibration is likely to have been incomplete at this time, because the test compound had degraded approximately 10% or less at this time in all systems. Th ese values, therefore, may be conservative but reasonable for exposure assessment.

Organic carbon-normalized coefficients (K OC 

### values) for flumiclorac acid ranged from 34 to 100 L/kg OC 

### , indicating that the compound is mobile in soil. K OC 

### values are appropriate to use

because their coefficient of variation (45%) is less than that for the K d 

### values (52%).

Table 5 lists the degradates of flumiclorac-pentyl and the amounts formed in the submitted environmental fate studies. Under hydrolysis at pH 9, the phthalimido ring is hydrolyzed open to produce 031-HA, which further hydrolyzes to IM CA-HA. At pH 5, the parent compound is cleaved into AFE and THPA. At pH 7, both de gradation pathways occur, with AFE further hydrolyzing to form AFCA. Interestingly, flumic lorac acid (IMCA) only appears to form due to microbial degradation.

Under aerobic conditions, flumic lorac acid, IMCA-HA, and 031-HA are major degradates that cleave to form the major cleavage products AF E, AFCA, and CFA as well as THPA (often complexed to sodium) and 1-OH-HPA, eventually forming un-extracted residues and carbon

dioxide.

### 21 of 87 Under anaerobic conditions, flumiclorac acid and IMCA-HA are major degradates, further hydrolyzing to form major degradates IMFP, IM FP-HA, and SAT IMFP-HA, all five degradates of which are structurally similar to the parent compound in that the amide bridge is preserved. Finally, the amide bridge is cleaved to form the major cleavage pr oducts THPA, AFCA, and AMFP. Degradates structurally similar to flum iclorac-pentyl do not pers ist, with the exception

of SAT IMFP-HA under anaerobic conditions. Figure 2 shows the probable degradation pathway of flumiclorac-pentyl re sidues in aerobic conditions. Figure 3 shows the probable degradation pathway in anaerobic conditions.

Figure 2. Aerobic degradation pathway of flumiclorac-pentyl (MRID 49063001, Figure 30).

### 22 of 87 Figure 3. Anaerobic degradation pathway of flumiclorac-pentyl (MRID 42825830, Figure 38).23 of 87Table 5. Flumiclorac-pentyl and Its Environmental DegradatesACode Name/SynonymChemical NameChemical StructureStudy TypeRef.(MRID)Maximum%AR (day)Final %AR(study length)PARENTFlumicloracpentylS-23031V-23031Pentyl 2-chloro-4-fluoro-5-(3,4,5,6-tetrahydrophthalimido)phenoxyacetateCAS No.:87546-18-7Formula:C21H23ClFNO5MW:423.87 g/molSMILES:FC1=C(C=C(C(=C1)Cl)OCC(=O)OCCCCC)N3C(=O)C2=C(CCCC2)C3=OFClOOONOOTRANSFORMATION PRODUCTS031-HAPentyl 2-chloro-4-fluoro-5-(2-carboxycyclohexenylcarboxanido)phenoxyacetateFormula:C21H25ClFNO6MW:441.89 g/molSMILES:C1(=C(CCCC1)C(=O)O)C(NC2=CC(=C(C=C2F)Cl)OCC(=O)OCCCCC)=OFClOOONOOOHHydrolysis –pH 5Hydrolysis –pH 7Hydrolysis –pH 9421698428.0% (1 d)86%(3 d)97%(55 min)nd (31 d)19%(31 d)0.30% (31 d)Aq. photo.– darkAq. photo.– light428258256.0% (1 d)6.8% (1 d)1.1% (14 d)5.6% (14 d)Aerobic soil 43304601 1.0% (56, 168 d) 1.0% (168 d)Aerobic aquatic 4906300126%(0.17 d) 0.1% (58 d)FlumicloracacidIMCA2-chloro-4-fluoro-5-(3,4,5,6-tetrahydrophthalimido)phenoxyaceticacidCAS No.:87547-04-4Formula:C16H13ClFNO5MW:353.74 g/molSMILES:FC1=C(C=C(C(=C1)Cl)OCC(=O)O)N3C(=O)C2=C(CCCC2)C3=OFClOOOHNOOHydrolysis –pH 5Hydrolysis –pH 7Hydrolysis –pH 942169842nd2.7% (17 d)ndnd1.3% (31 d)ndSoil photo.– darkSoil photo.– light4282582670%(2 d)39%(2 d)33%(21 d)10%(21 d)Soil photo.– darkSoil photo.– light42825827--43%(2 d)--5.0% (30 d)Aerobic soil4216984453%(1 d) 1.8% (85 d)4330460160%(6 hrs) 1.4% (168 d)Anaerobic aquatic4282582964%(6 hrs) 0.8% (45 d)4282583063%(6 hrs) 1.2% (30 d)Aerobic aquatic 4906300141%(0.13 d) 1.5% (100 d)Field studies42825836 100% (1 d) nd (14 d)42825837 70% (1 d) nd (84 d)46563601 71% (0 d) nd (14 d)24 of 87Code Name/SynonymChemical NameChemical StructureStudy TypeRef.(MRID)Maximum%AR (day)Final %AR(study length)IMCA-HAN-(5-carboxymethoxy-4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalamic acidFormula:C16H15ClFNO6MW:371.75 g/molSMILES:C1(=C(CCCC1)C(=O)O)C(NC2=CC(=C(C=C2F)Cl)OCC(=O)O)=OFClOOOHNOOOHHydrolysis –pH 5Hydrolysis –pH 7Hydrolysis –pH 942169842nd24%(31 d)100%(3-7 d)nd24%(31 d)98%(31 d)Aerobic soil 4330460110%(4 d) nd (168 d)Anaerobic aquatic4282582924%(1 d)nd (45 d)4282583029%(1 d)nd (30 d)Aerobic aquatic 4906300158%(3 d) 0.6% (100 d)IMFPN-(4-chloro-2-fluoro-5-hydroxyphenol)-3,4,5,6-tetrahydrophthalimideFormula:C14H11ClFNO3MW:295.70 g/molSMILES:C13=C(CCCC1)C(N(C2=CC(=C(C=C2F)Cl)O)C3=O)=OFClOHNOOAnaerobic aquatic4282582927%(3 d)9.1% (45 d)4282583025%(9 d)13%(30 d)IMFP-HAN-(4-chloro-2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalamic acidFormula:C14H13ClFNO4MW:313.72 g/molSMILES:C1(=C(CCCC1)C(=O)O)C(NC2=CC(=C(C=C2F)Cl)O)=OFClOHNOOOHAnaerobic aquatic4282582925%(3 d)0.3% (45 d)4282583032%(3 d) 1.8% (30 d)SAT IMFPHAN-(4-chloro-2-fluoro-5-hydroxyphenyl)hexahydrophthalamic acidFormula:C14H15ClFNO4MW:315.73 g/molSMILES:C1(CCCCC1C(=O)O)C(NC2=CC(=C(C=C2F)Cl)O)=OFClOHNOOOHAnaerobic aquatic4282582914%(45 d)14%(45 d)4282583015%(30 d)15%(30 d)25 of 87Code Name/SynonymChemical NameChemical StructureStudy TypeRef.(MRID)Maximum%AR (day)Final %AR(study length)AFEPentyl 5-amino-2-chloro-4-fluorophenoxyacetateFormula:C13H17ClFNO3MW:289.74 g/molSMILES:C1=C(C(=CC(=C1OCC(=O)OCCCCC)Cl)F)NFClOOONH2Hydrolysis –pH 5Hydrolysis –pH 7Hydrolysis –pH 94216984294%(28-31 d)15%(7 d)nd94%(31 d)nd (31 d)ndAq. photo.– darkAq. photo.– light4282582499%(14 d)B19% (3 d)B99%(14 d)B6.2% (14 d)BAnaerobic aquatic 42825830 1.1% (16 d) 0.7% (30 d)Aerobic aquatic 4906300138%(0.17 d) 0.1% (58 d)AFCA5-amino-2-chloro-4-fluorophenoxyaceticacidFormula:C8H7ClFNO3MW:219.60 g/molSMILES:C1=C(C(=CC(=C1OCC(=O)O)Cl)F)NFClOOOHNH2Hydrolysis –pH 5Hydrolysis –pH 7Hydrolysis –pH 9421698422.0% (31 d)68%(31 d)1.7% (31 d)2.0% (31 d)68%(31 d)1.7% (31 d)Soil photo.– darkSoil photo.– light4282582615%(21 d)11%(21 d)15%(21 d)11%(21 d)Aerobic soil 4216984420%(7 d) 1.5% (85 d)Anaerobic aquatic 42825830 9.2% (3 d) 1.3% (30 d)Aerobic aquatic 4906300145%(3 d) 3.5% (58 d)CFACFPA(2-chloro-4-fluorophenoxy)acetic acidCAS No.:399-41-7Formula:C8H6ClFO3MW:204.59 g/molSMILES:c1cc(c(cc1F)Cl)OCC(=O)OFClOOOHAerobic aquatic 4906300124%(3 d) 0.8% (100 d)AMFP5-amino-2-chloro-4-fluorophenolFormula:C6H5ClFNOMW:161.56 g/molSMILES:C1=C(C(=CC(=C1O)Cl)F)NFClOHNH2Anaerobic aquatic 4282583017%(9 d) 8.0% (30 d)26 of 87Code Name/SynonymChemical NameChemical StructureStudy TypeRef.(MRID)Maximum%AR (day)Final %AR(study length)THPA3,4,5,6-tetrahydrophthalic acidFormula:C8H10O4MW:170.17 g/molSMILES:C1(=C(CCCC1)C(=O)O)C(=O)OOOOHOHHydrolysis –pH 5Hydrolysis –pH 7Hydrolysis –pH 94216984296%(26 d)71%(31 d)nd94%(31 d)71%(31 d)ndAq. photo.– darkAq. photo.– light4282582592%(14 d)57%(10 d)92%(14 d)36%(14 d)Soil photo.– darkSoil photo.– light42825827--22%(10 d)--15%(30 d)Aerobic soil 4330460127%(14 d) 0.5% (168 d)Anaerobic aquatic 4282582958%(30 d)55%(45 d)Aerobic aquatic 4906300125%(3 d) nd (58 d)THPA-2-NaDisodium 3,4,5,6-tetrahydrophthalicacidFormula:C8H8O4. 2 NaMW:214.13 g/molSMILES:C1CCC(=C(C1)C(=O)O[Na])C(=O)O[Na]OO-O-ONa+Na+Aerobic aquatic 4906300181%(3 d)1.9% (100 d)1-OH-HPA1-hydroxy-trans-1,2-cyclohexanedicarboxylic acidFormula:C8H12O5MW:188.18 g/molSMILES:C1(C(CCCC1)C(=O)O)(C(=O)O)OOOOHOHOHAerobic soil 4330460134%(85 d)21%(168 d)Aerobic aquatic 4906300116%(62 d) 5.4% (100 d)Unidentifiedresidues(unknown)(unknown)Aq. photo.– darkAq. photo.– light428258245.0% (14 d)C57%(14 d)C5.0% (14 d)C57%(14 d)CAq. photo.– light 4282582522%(14 d)C22%(14 d)CSoil photo.– darkSoil photo.– light4282582611%(21 d)C32%(7 d)C11%(21 d)C22%(21 d)CSoil photo.– darkSoil photo.– light42825827--13%(11 d)C--8.1% (30 d)CAerobic soil 4330460128%(4 d)D21%(168 d)DUnknown AEAerobic aquatic 4906300112%(14 d)1.1% (100 d)Unknown CE37%(0.13 d)0.0% (100 d)27 of 87Code Name/SynonymChemical NameChemical StructureStudy TypeRef.(MRID)Maximum%AR (day)Final %AR(study length)Unextractedresidues(not applicable)(not applicable)Soil photo.– darkSoil photo.– light4282582630%(21 d)35%(21 d)30%(21 d)35%(21 d)Soil photo.– darkSoil photo.– light4282582715%(11 d)35%(30 d)9.4% (30 d)35% (30 d)Aerobic soil4216984473%(85 d)73%(85 d)4330460131%(28 d)23%(168 d)Anaerobic aquatic42825829 3.3% (45 d)3.3% (45 d)4282583023%(23 d)20%(30 d)Aerobic aquatic 4906300154%(58 d)54%(58 d)CarbondioxideCarbon dioxideFormula:CO2MW:44.01 g/molSMILES:O=C=OOOAq. photo.– light 4282582423%(14 d)23%(14 d)Aq. photo.– darkAq. photo.– light428258250.04% (1 d)0.59% (1 d)0.04% (1 d)0.59% (1 d)Soil photo.– darkSoil photo.– light428258260.02% (21 d)7.3% (21 d)0.02% (21 d)7.3% (21 d)Soil photo.– darkSoil photo.– light428258270.02% (30 d)14%(30 d)0.02% (30 d)14%(30 d)Aerobic soil42169844 2.0% (85 d) 2.0% (85 d)4330460136%(168 d)36%(168 d)Anaerobic aquatic42825829 0.6% (45 d) 0.6% (45 d)42825830 0.7% (30 d) 0.7% (30 d)Aerobic aquatic 4906300150%(100 d)50%(100 d)And means “not detected”. AR means “applied radioactivity”. MW means“molecular weight”. Code names of residues of concern are underlined. Bolded percentages arelaboratory study values >10%AR.BAFE in MRID 42825824 was AFE plus 031-HA, the latter of whichwas not a major degradate at pH 5 in MRID 42169842 or 42825825.CThese unidentified residues were a collection of polar compounds. In MRIDs 42825824, 42825826, and 42825827, none of the polar compounds exceeded 10% of the applied(no product exceeded 5% of the applied in MRID 42825827). InMRID 42825825, none of the polar compounds exceeded 20% of the applied.DThese unidentified residues were organo-soluble.EThese unidentified residues were transient.Additional efforts to identify unknown C failed.

### 28 of 87 3.1.1 Residues of Concern

The flumiclorac-pentyl residues of concern include the parent compound and the six major degradates with an intact imido/carboxamido bridge (flumiclorac acid, 031-HA, IMCA-HA, IMFP, IMFP-HA, and SAT IMFP-HA). These compounds are assumed to be of similar toxicityas flumiclorac-pentyl. Toxicity data have not been submitted for degradates of flumicloracpentyl other than for flumiclorac acid. ECOSAR v1.11 estimates for flumiclorac-pentyl and its

acid did not correlate well with measured toxici ty values that were often non-definitive ( Appendix E ). Therefore, they were not useful pr edictors of toxicity. Degradates with a cleaved imido or carboxamido bridge, such as the phthalic acids, are not structurally similar to the parent compound and are, thus, assumed to be less toxic. In contrast , degradates with an intact imido or carboxamido bridge are considered to have toxicity profiles similar to that of flumiclorac-pentyl on the basis of the structural similarities. Therefore, in the absence of toxicity data indicating otherw ise, the six major degradates with an intact imido/carboxamidobridge are assumed to be of similar toxicity to aquatic and terrestrial organisms as flumicloracpentyl. The same residues are of concern for eco logical risk assessment as for drinking water exposure assessment in support of human health dietary risk assessm ent (U.S. EPA, 2014).

Table 6 provides the environmental fate parameters for the flumiclorac-pentyl residues of concern (ROC). Degradation half -lives were calculated using the sums of the residues of concern at each study interval. Note that biodegradation half-liv es for the ROC are substantially longer (25-59 days) than for the parent compound and that the data were not specific enough to allow the subtraction of hydrolysis from the degradation rates. The ROC hydrolysis half-life at pH 5 is not substantially differe nt from that for the parent compound. However, at pH 7, the ROC half-life is 20 days, which is much longer th an 18 hours. And at pH 9, at which the parent compound is unstable in minutes, the ROCs are relatively stable, forming IMCA-HA that does not further degrade under abiotic conditions.

Table 6. Environmental Fate Parameters of Flumiclorac-pentyl Residues of Concern

Parameter Value Source

Persistence in Water

Hydrolysis half-life (25  C) pH 5: 4.9 d pH 7: 20 d pH 9: 3000 d MRID 42169842

Aqueous photolysis half-life (25  C) No substantial degradation of parent compound MRID 42825824,

42825825

Anaerobic aquatic metabolism half-life (25°C, pH 6.83) 59 d (including hydrolysis) MRID 42825829/

42825830

Aerobic aquatic metabolism half-life (25  C; pH 6.84-8.64) 25-39 d (including hydrolysis) MRID 49063001

Persistence in Soil

Soil photolysis half-life (25 °C) No substantial degradation of parent compound MRID 42825826,

42825827

### 29 of 87 Parameter Value Source

Aerobic soil metabolism half-life (26°C) (kinetics model in parentheses) 26, 34 d (IORE) MRID 42169844,

43304601

Mobility

Organic carbon-normalized soil-water partition coefficients (K OC 

### ) 34, 49, 72, 100 (values for flumiclorac acid) MRID 42169845/

49175801

A IORE means “indeterminate order rate equation.”



### EPI Suite (v4.10) indicates that flum iclorac acid is more mobile than or as mobile as most of the degradates of flumiclorac-pentyl (the cl eavage products AFCA a nd 1-OH-HPA are the exceptions). Because flumiclorac acid is a promin ent degradate of flumiclorac-pentyl and it is one of the more mobile residues of concern, K OC 

### values for flumiclorac acid are a reasonably conservative representation of the soil mobility of flumiclorac-pentyl’s residues of concern.

3.2. Aquatic Exposure

The Total Residue of Concern (TRC) modeling appr oach was used to estimate aquatic exposure with the ROC half-lives (from Table 6 ), the soil mobility of flumiclorac acid (from Table 6 ), and the physical/chemical propertie s of flumiclorac-pentyl (from Table 3 ). The TR approach is appropriate because there are multiple degrad ates of concern, for none of which a full environmental fate data profile is available, and the toxic moiety of flumiclorac-pentyl appears to potentially be intact. TRC calculations are in Appendix C

.

PE chemical inputs for the ROC are listed in Table 7 . PE only accepts first-order degradation half-lives. Therefore, non-firs t-order representative half-liv es based on the study data were treated as first-order half-lives. For example, the non-first-order aquatic metabolism half-lives in

Table 6 were treated as first-order half-lives when adjusted for the first-order hydrolysis rate at pH 7. Upper bound input values based on the resulti ng hydrolysis-adjusted half-lives were then calculated according to current guidance (U SEPA, 2009) to produce the input values in Table 7

.

Table 7. PE Chemical Input Parameters fo r Flumiclorac-pentyl Residues of Concern

Input Parameter Value Justification Source

Molecular Mass (g/mol) 423.87 Produc t chemistry data (Calculated)

Henry’s Law Constant (atm m 3 

### /mol) 3.0 × 10 -7 

### Ratio of vapor pressure to water solubility (Calculated from MRID 42187405)

Solubility in Water (mg/L) 0.189 Study va lue for flumiclorac-pentyl MRID 42187405

Organic Carbon Partition Coefficient (K OC 

### ) (L/kg OC 

### ) 64 Mean value for flumiclorac acid, a prominent degradate of concern MRIDs 42169845/

49175801

Aerobic Soil Metabolism Half-life (days) 42 90 th 

### percentile confidence bound on the

mean TRC value for two soils MRIDs 42169844,

43304601

Aerobic Aquatic Metabolism Half-life (days) 153 90 th 

### percentile confidence bound on the mean TRC value for two systems,

adjusted for hydrolysis at pH 7 MRID 49063001

### 30 of 87 Input Parameter Value Justification Source

Anaerobic Aquatic Metabolism Half-life (days) 88.5 Single available anaerobic aquatic metabolism value adjusted for hydrolysis at pH 7, times three MRIDs 42825829/

42825830

Hydrolysis Half-life at pH 7 (days) 20 Single first-order value at pH 7 MRID 42169842

Aqueous Photolysis Half-life (days) 0 No substantial degradation of parent compound MRIDs 42825824,

42825825



### PRZM use pattern inpu ts are listed in Table 8 . Modeled application rates and numbers of applications per year include the maximum allowed on a label. For each use, multiple PRZM scenarios ( e.g. , FL turf and PA turf) may have been modeled as well as aerial and ground application methods, with applicab le application rates, for uses on soybeans and field corn. The PRZM scenarios, application efficienci es, and spray drift factors listed in Table 8 , however, represent the single modeling scen arios for each use that resulted in highest exposure (including consideration of Sp ring burndown uses).

Dates of initial application were selected with in the scenario crop season and characterized by vulnerability to runoff. Runoff vulnerability was explored by modeling a range of initial application dates falling on the 1 st 

### or 15 th 

### of months within the crop season and selecting the date for which exposure estimates were highest. Th is was expected to produce high-end exposure estimates that are conservative but that may not represent the highest possible exposure. If exposure estimates resulting from these high-e nd exposure scenarios do not result in risk concerns, then there are no ri sk concerns from less-high-e nd exposure scenarios either.

Table 8. PRZM Scenarios and Input Parame ters Describing Maximum Patterns of Flumiclorac-pentyl Use on Representative Use Sites

Use Site PRZM

Scenario Date of

Initial App. App. Rate in

lbs a.i./A (kg a.i./ha) App.

per Year App.

Interval

(days) CAM Input IPSCND Input Application Efficiency/ Spray

Drift

Field corn KS corn Jun. 15 0.054 (0.0605) 1 N/A 2 1 0.99/0.01

Cotton MS cotton Sep. 1 0.054 (0.0605), 0.040 (0.045) A 2 A 7 2 1 0.99/0.01

Soybeans MS soybean Jun. 1 0.054 (0.0605) 2 14 2 1 0.95/0.05

Sod farms &

non-ag areas PA turf Sep. 1 0.028 (0.031) 2 7 2 1 0.95/0.05

A Two applications per year were modeled for cotton: one at 0.054 lbs a.i./A, the maximum single application rate, the other at 0.040 lbs a.i./A, which is the balance be tween the maximum single and annual application rates.



### Surface water exposure estimates per use site for flumiclorac-pentyl residues of concern are

listed in Table 9 . Model input and output files are attached in Appendix C . The maximum use pattern on field corn results in the highest en vironmental exposure concentrations (EEC).

### 31 of 87 Table 9. Aquatic Exposure Estimates fr om Flumiclorac-pentyl Use Sites A



### Use Site PRZM Scenario 1-in-10-year Peak (μg/L) 1-in-10-year 21- day Mean (μg/L) 1-in-10-year 60- day Mean (μg/L)

Field corn KS corn 

### 3.4 2.4 1.4

Cotton MS cotton 

### 2.7 1.8 1.1

Soybeans MS soybean 

### 1.7 1.1 0.77

Sod farms & non-ag areas PA turf 

### 0.74 0.50 0.29

A Maximum values are in bold.



### 3.2.1 Bioaccumulation

Flumiclorac-pentyl residues of concern are not ex pected to appreciably bioaccumulate in aquatic or terrestrial organisms because the parent compound hydrolyzes within hours to ionic degradates with K OW 

### values orders of magnitude lower th an that of the parent compound, with one exception (see Table 4 ). The half-acid 031-HA is estimated to have a K OW 

### above that of the parent compound; however, similar to the parent compound, it is rapidly degraded within hours (MRID 49063001). With a log K OW 

### of 4.99, however, flumiclorac-pe ntyl meets the criteria for

chemicals that are modeled with KABAM fo r bioaccumulation in birds and mammals.

KABAM (v.1.0; Apr. 7, 2009) was used to estimat e potential bioaccumulation of flumicloracpentyl residues in a freshwat er aquatic food web and subseque nt risks these residues pose to terrestrial organisms via consumpti on of contaminated aquatic prey ( i.e. , aquatic invertebrates and fish). The model was run in default mode (s ee user’s guide for full description), with a log

K OW 

### of 4.99, a K OC 

### of 4,430 L/kg OC 

### (estimated with EPISuite v4.11), and a surface water and pore water EEC of 3.4 μ g/L, which is the 1-in-10-year peak concentration of flumiclorac-pentyl ROCs using PRZM/EXAMS for the use pattern of maximum exposure. This EEC was selected because its exposure duration is similar to flumic lorac-pentyl’s time to reach 90% of steady state in the submitted fish BCF studies of 2.5-3.0 days (MRIDs 42169809 and 42169810). These inputs are conservative because mo st residues of concern have a K OW 

### value orders of magnitude lower than that of flumiclorac-pentyl. A metabolism rate constant (k M 

### ) was not input for fish because the estimated depurati on rate in KABAM was higher th an the rates observed in the

submitted fish BCF studies.

The resulting exposure estimates of flumiclorac- pentyl in mammals and birds ingesting fish contaminated by the compound were used to deri ve RQs based on dose-based or dietary-based exposures of birds, terrestrial phase amphibians, reptiles, and mammals to flumiclorac-pentyl through consumption of contaminated aquatic prey. No RQs exceeded risk LOCs for any organism, which strengthens the ex pectation that flumiclorac-pent yl and its residues of concern will not appreciably bioaccumulate in aquatic or terrestrial orga nisms. Exposure estimates and RQs are in the attached KABAM file in Appendix C

.

3.2.2 Monitoring Data

Flumiclorac-pentyl and its acid are not analytes in the following water monitoring programs: the California Department of Pesticide Re gulation (CDPR) surface water database ( http://www.cdpr.ca.gov/docs/ emon/surfwtr/surfcont.htm , the USGS NAWQA surface and

### 32 of 87 ground water database ( http://cida.usgs.gov/nawq a_public/apex/f?p=nawqa: ), the USEPA STORET Data Warehouse ( http://www.epa.gov/storet/ ), and the USDA Pesticide Data Program drinking water monitoring analyses ( http://www.ams.usda.gov/AMSv1.0/ams.fetchTem plateData.do?template=TemplateG&navID= &rightNav1=&topNav=&leftNav=ScienceandLa boratories&page=PDPDownloadData/Reports& resultType=&acct=pestcddataprg ).

3.3. Terrestrial Exposure

The Agency used the Terrestrial Residue EX posure model (T-REX) model to estimate the terrestrial animal exposure values resulting from possible dietary ingestion of residues on vegetative matter and insects present on non-food a nd food crops from single as well as multiple exposures to flumiclorac. In all screening- level assessments, the organisms are assumed to consume 100% of their diet as one food type. This model incorporates the Kenaga nomograph, as modified by Fletcher et al. (1994), which is based on a large set of actual field residue data. The upper limit values from the nomograph represented the upper bound residue values from actual field measurements (Hoe rger & Kenaga, 1972). The m odel was employed to estimate EECs for different food items for birds and mammals. These EECs were then compared to available acute and chronic toxicity data to calcu late Rick Quotients (RQs) for estimation of risk for these species. Birds are also used as a surroga te for reptiles and terres trial-phase amphibians.

The TERRPLANT model can be used to estimat e risk from runoff to monocot and dicot terrestrial plants in ar eas adjacent to the treated field (she et runoff), wetland areas (channelized runoff), and from spray drift.

3.4. Effects Characterization

3.4.1 Effects to Aquatic Organisms

A summary of sensitive aquatic toxicity data fr om registrant-submitted studies is provided in

Table 10. Appendix A includes a table summarizing toxicity data submitted to the Agency.

The reported solubility of flumiclorac-pent yl is 0.189 mg/L (MRID 42187405). In discussions with The Agency on January 18, 1989 and on Febr uary 27, 1992, the registrant indicated that preliminary aquatic animal testing with flum iclorac-pentyl indicat ed they had problems achieving solubility within the pa rameters outlined in guideline te sting. They were unable to achieve solubility greater than 0.1 mg flumiclorac-pentyl/L w ith the guideline recommended cosolvents at a concentration of 0.1 mL solvent/L te st solution. They also indicated that no fish mortality was observed at 0.1 mg/L of flumiclorac- pentyl. Therefore, alte rnative co-solvents and solvent concentrations for use in aquatic animal testing were requested by the registrant. Agency

staff at the time indicated that th e registrant should provide justif ication for these extra measures and would view favorably a well designed st udy which resulted in a dose response. The registrant provided information for the us e of dimethyl formamide: polyoxyethylene hydrogenated castor oil (1:1, DMF:HCO-40), and toxi city data for bluegill sunfish and rainbow trout from this solvent mixture (MRID 42169808) . Based on this information, the aquatic studies were conducted using a DMF:HCO-40 so lvent concentration range of 0.56 mL/L – 4

### 33 of 87 mL/L for the fish studies, and 4 mL/L for the Daphnia magna toxicity study. The 96-hour acute mysid and oyster toxicity studies were conducte d at solvent concentrat ions of 0.5 mL DMF/L only, as HCO-40 was found to be toxic to oysters.

Even with the use of this alternative co-solve nt mixture and increased solvent concentrations, precipitate was observed in some of the aquatic toxicity studies. Precipitate was observed either

in the test chambers or the de livery system. No precipitate was reported in the 96-hour acute mysid toxicity study. Test solution appearance was not reported for e ither the acute rainbow trout or bluegill toxicity study. So while a pres ence of precipitate was not mentioned in these reports, the absence of precipita te cannot be assumed based on the known solubility of the chemical and presence of precipitate in the othe r toxicity studies. Fo r all studies in which precipitate was observed, an attempt to remove th e precipitate from the an alytical samples prior to analysis (ex. centrifugation, filt ering) was not reported. Theref ore, it is not known what the actual dissolved flumiclorac-pentyl concentration in the test sy stems were, as the presence of precipitate during analysis could overestimate th e actual exposure concentration. All of these studies were conducted above the reported solub ility of 0.189 mg/L for flumiclorac-pentyl, and therefore, the NOAEC level for al l aquatic studies are above this reported water solubility. LC 50 

### values were obtained for the blue gill sunfish, rainbow trout and my sid invertebrate, but with the exception of the mysid toxicity data, actual aqua tic exposure concentrations are uncertain. A LC, EC 50 

### concentration could not be determ ined for the sheepshead minnow or Daphnia magna toxicity study, respectively, due to a lack of dose response. Since th is uncertainty exists for these aquatic studies in which precipita te was observed these studies are classified as supplemental. Also, the 96-hour oyster shell gr owth deposition study was classifi ed as supplemental since there was minimal new shell growth in the control treatment groups, substantial decrease in measured test solution concentration and dissolved oxygen fell below the required 60% of saturation for the four highest treatment groups. Since the dissolved oxygen was greater than 60% for the lowest treatment group (0.61 mg ai/L, mean measur ed), and the growth was comparable to the controls, it appears that flumiclorac-pentyl does not inhibit oyster shell growth at the reported limit of solubility (0.189 mg/L). Also, since th ere is an acceptable mysid toxicity study, that study will be used to evaluate estuarine-marine invertebrate risk to flumiclorac-pentyl. Therefore, the oyster deposition study will not need to be repeated at this time.

Based on the limited mobility of flumiclorac-pe ntyl and its degradation to IMCA, aquatic

vascular and non-vascular studies were conducted with IMCA at one concentration. This was

based on information that IMCA is mobile in soil and expected to runoff, and its similar chemical structure to parent flumiclorac-pentyl indicates it may be phytotoxic. The

concentration of IMCA tested was based on the maximum application of flumiclorac-pentyl and the degradate IMCA comprising 53% of the pa rent flumiclorac-pent yl (up to 1 day posttreatment), therefore, the maximum application rate of IMCA was determined. When this amount is applied into 6 inches of water, a conc entration of IMCA in water was determined and

used as the limit concentration. The aquatic vascular plant, Lemna gibba, toxicity study using

IMCA at one concentration showed a 3.3 and 12% increase in frond nu mber and dry weight when compared to the negative control. The nonvascular, green algae toxicity study at the

IMCA limit concentration showed a 4.1% decrease in cell dens ity compared to the negative

control.

### 34 of 87 There are no chronic toxicity data for freshwater or estuarine-mari ne fish. Flumiclorac-pentyl is a light-dependent peroxidizing herbicide (LDPH), a nd may be very toxic to aquatic organisms. Therefore, the Aquatic Biology Tech Team (AB TT) recommends that phot otoxicity studies be

conducted on herbicides with this mode of acti on to determine if animals exposed to LDPHs and intense light (similar to sunlight) show increased toxicity relative to co ntrols exposed to LDPHs and low intensity light with the suggested test species, the fathead minnow (See Appendix C Memorandum: Request for Phototoxicity Study Protocol for Light-Dependent Peroxidizing Herbicides, Dated March 7, 2001). A data call- in (DCI) was issued on January 25, 2006 for a fish early life-cycle study using enha nced lighting (GDCI-128724-26284). This DCI requirement has been satisfied by surrogate data submitted on other LDPH herbicides. However, the standard fish early life-cycle study was never required for flumiclorac-pentyl as it was for the other herbicides in the LDPH gr oup. Thus, the Agency does not have a toxicity endpoint derived from the standard, non-enhanced lighting study to apply an LDPH safety factor (currently 29X)

to for estimation of chronic risk to fish. Base d on flumiclorac-pentyl’s mode of action, adverse effects to aquatic organisms under natural sunlight are expected to occur at lower levels than shown in studies conducted using lower light inte nsity. Effects to estuarine-marine fish and aquatic-phase amphibians are also possible based on surrogacy to freshwater fish.

Table 10. Summary of sensitive endpoints fo r aquatic organisms under consideration for use in the risk assessment for flumiclorac-pentyl*

Common Name (Species)

TGAI Duration End-point (effect) Mean

concentration in mg a.i./L (effect) Citation or

MRID/status or

review Acute Toxicity

Classification

Freshwater Vertebrates

Rainbow Trout ( Onchorhyncus mykiss )

TGAI 96 hours LC 50 > 0.189 1

1.1 2 (mortality) 42169806 Acceptable Moderately Toxic 3

Fathead Minnow (Pimephales promelas)

TGAI Full Lifecycle NOAEC No Data No Data No Data

Fathead Minnow (Pimephales promelas)

TGAI Early Life Stage under

enhanced UV lighting NOAEC No Data No Data No Data

Estuarine Marine Vertebrates

Sheepshead Minnow (Cyprinodon variegates)

TGAI 96 hours LC 50 > 0.189 1

> 24 2 (mortality) 42825809 Supplemental NA 4

Sheepshead Minnow (Cyprinodon variegates)

TGAI Early Life Stage under

enhanced UV lighting NOAEC No Data No Data No Data

Freshwater Invertebrates

Waterflea (Daphnia magna)

TGAI 48 hours EC50 > 0.189 1

> 38 2 (mortality) 42169808 Acceptable NA 4

Waterflea (Daphnia magna) Full Lifecycle NOAEC 0.67 (IMCA) (no effects) 48848801 Acceptable N/A

Estuarine Marine Invertebrates

Mysid Shrimp ( Americamysis bahia )

TGAI 96 hours LC 50 0.56 (mortality) 42825801 Acceptable Highly Toxic

### 35 of 87 Common Name (Species)

TGAI Duration End-point (effect) Mean

concentration in mg a.i./L (effect) Citation or

MRID/status or

review Acute Toxicity

Classification

Mysid Shrimp ( Americamysis bahia )

TGAI Full Lifecycle NOAEC 0.22 (IMCA)

F 0 pre-pairing and

overall survival 48848701 Acceptable N/A

Aquatic Nonvascular and Vascular Plants

Freshwater Diatom Navicula pelliculosa 96 hours NOAEC

EC50 0.88 (IMCA) >0.88 (IMCA) 48864401 Acceptable NA 4

Marine Diatom

Skeletonema costatum 96 hours NOAEC

EC50 0.41 (IMCA) >0.41 (IMCA) 48864501 Acceptable NA 4

Freshwater Blue-green Algae Anabaena flos-aquae 96 hours NOAEC

EC50 0.82 (IMCA) >0.82 (IMCA) 48804301 Acceptable NA 4

Green Algae Selenastrum capricornutum 96 hours NOAEC

EC50 0.035 (IMCA) > 0.035 (IMCA) 43240800 Acceptable NA 4

Duckweed Lemna gibba 14 day NOAEC

EC50 0.035 (IMCA) > 0.035 (IMCA) 43251201 Acceptable NA 4

TGAI=technical grade active ingredient; LC 50 = median lethal concentration; NOAEL=no observabl e adverse effect level; a.i. active ingredient * Data in this table may be used in the risk assessment, but it will not necessarily be used to calculate risk quotients.

1 No toxicity up to the reported limit of solubility (0.189 mg a i/L). Actual test concentrati on not known due to the presence o f precipitates in test solution or exclusion of test solution appearance and removal of possible precipitate from test solutions prior to analysis not reported.

2 Measured concentration reported in study.

3 Classification class based on reported meas ured test concentration and not greater than value based on reported solubility.

4 Due to no toxicity at both reported limit of solubility (0.189 mg ai/L), and measured test concentration, or limit test (aquat ic nonvascular and vascular plants with IMCA) toxicity classification could not be determined.



### 3.4.2 Effects to Terrestrial Organisms

A summary of sensitive terrestrial toxicity data from registrant-submitted studies is provided in

Table 11. Appendix A includes a table summarizing toxicity data submitted to the Agency. Flumiclorac-pentyl is classified as practica lly nontoxic to birds, mammals, and terrestrial

invertebrates.

Acute, subchronic, and chronic t oxicity studies are available for mammals. According to the HED chapter of the 2005 TRED (USEPA 2005d), in mammals, technical flumiclorac-pentyl has low acute toxicity via th e oral, dermal and inhalation routes of exposure

. 

### Flumiclorac-pentyl did not cause developmental toxicity in rat or rabbi t fetuses. Reproductive parameters were not adversely affected in rats in a reproducti on study. No evidence of neurotoxicity or carcinogenicity was observed.

No mortality was observed in acute oral-dose or subacute dietary avia n studies. Reduced egg laying, regressed ovaries and small testes were ob served in the chronic study with the mallard

duck. There were no adverse effects obser ved in the chronic bobwhite quail study.

Based on the degradation of parent flumiclor ac-pentyl to IMCA and IMCA’s potential for mobility in soils, a seedling emergence limit test was conducted using IMCA. The concentration of IMCA used in this study was based on the ma ximum application rate of flumiclorac-pentyl and the expected maximum concentration of th e degradate IMCA (53% of the flumiclorac-

### 36 of 87 pentyl) to be present. The study was conduc ted with both a negative and solvent control (acetone), but percent emergence and shoot heig ht comparisons between the negative control and treatment group is more appropriate than a co mparison using pooled controls. Based on a reduction in shoot lengths, the onion and oat we re statistically signifi cant compared to the negative control and the shoot height reductions ranged from -9.8 to 15% compared to the negative control. Decreases in seedling emergen ce for the limit concentration ranged from -12 to 12% compared to the negative control. No adverse effects were observed for phytotoxic symptoms. Dry weight was not measured in the seedling emerge nce study which is generally a sensitive endpoint for evaluating toxicity. The vegetative vigor study was conducted using parent flumiclorac-pentyl. The most sensitiv e species based on phytotoxicity was the tomato.

Table 11. Summary of sensitive toxicity endpoints for terrestrial organisms under

consideration for use in risk assessment*

Common Name (Species)

TGAI /TEP End-point Mean Concentration and Effect Citation or

MRID /

Status Acute Toxicity

Classification

Mammals

Rat (Rattus norvegicus)

TGAI LD 50 > 5,000 mg/kg (mortality) 42169812/ Acceptable Practically

Nontoxic

Rat (Rattus norvegicus)

V-23031 0.83 EC LD 50 4,100 mg/kg (mortality) (males) 3,200 mg/kg (mortality) (females)

3,600 mg/kg (mortality) (both) 42169813/ Acceptable Practically

Nontoxic

Rat (Rattus norvegicus)

TGAI 2 generation reproduction

NOAEC/

LOAEC Reproductive NOAEL = 200 ppm LOAEL = 10,000 ppm Based on increases pup death on day 0 42169835/ Acceptable NA 1

Birds Bobwhite Quail (Colinus virginianus)

TGAI

Zebra Finch ( Taeniopygia

guttata )

TGAI LD 50 > 2131 mg ai/kg-bw (no mortality)

>2000 mg ai/kg-bw (no mortality) 42169802/ Acceptable

48603301/ Acceptable Practically

Nontoxic

Bobwhite Quail (Colinus virginianus) /

Mallard Duck ( Anas platyrhynchos )

TGAI 8-day

LC 50 >5322 mg ai/kg-diet (no mortality) 42169803,

42169804/ Acceptable NA 1

Mallard Duck ( Anas platyrhynchos )

TGAI Chronic reproduction

NOAEC/

LOAEC 220/432 mg ai/kg-diet (Based on reduction in egg laying and

regressing ovaries and small testes) 42825806/ Acceptable NA 1

### 37 of 87 Terrestrial Invertebrates
Honey Bee (Apis mellifera)

TGAI Contact

LD 50 > 106 μg/bee (no mortality) 42169841/ Acceptable Practically

Nontoxic

Terrestrial Plants

Seedling Emergence Seedling Emergence EC 25 > 0.046 lb IMCA/Acre 43258001/ Acceptable NA 1

NOAEC < 0.046 lb IMCA/Acre 2

Vegetative vigor Vegetative vigor EC 25 0.027 lb ai/Acre (Based on dry weight for lettuce) 43347401/ Acceptable NA 1

NOAEC 0.00031 lb ai/Acre (Based on phytotoxicity for tomato)

* Data in this table may be used in the risk assessment, but it will not necessarily be used to calculate risk quotients.

1 Toxicity Classification no t applicable for study.

2 Due to study conducted as a limit test, a nd differences greater than 5% compared to control for both emergence and shoot height, a definitive NOAEC could not be determined

.



### 4. RISK CHARACTERIZATION

In order to address the risk hypot hesis, the potential for adverse effects on the environment is estimated. The use, environmental fate, and ecol ogical effects of flumiclo rac-pentyl residues of concern are characterized and integrated to assess the risks. This is accomplished using a risk quotient (RQ; ratio of exposure co ncentration to effect s concentration) approach. The resulting RQs are compared to the Agency’s risk levels of concern (LOC), which are the Agency’s interpretive policy such that wh en acute or chronic risk LOCs are exceeded, the need for regulatory action may be considered. These crit eria are used to indicate when the use of a pesticide, as directed on the label, has the pot ential to cause adverse effects to non-target organisms. For acute and chronic risks to anim als, the LOCs are 0.5 and 1.0, respectively, and for plants, the LOC is 1.0. For each taxa, RQs are generated and risks are discussed. This

discussion includes consideration of a dditional data and lines of evidence.

Although risk is often defined as the likelihood a nd magnitude of adverse ecological effects, the risk quotient-based approach does not provide a quantitative estimat e of likelihood and/or magnitude of an adverse effect. However, as outlined in the Overvi ew Document (U.S. EPA 2004), the likelihood of effects to individual organisms from part icular uses of flumicloracpentyl is estimated using th e probit dose-response slope and either the level of concern (discussed below) or the actual calculated risk quotient value.

4.1. Terrestrial Environment

4.1.1 Avian and Mammalian Dietary Residues

The predicted maximum residues of flumiclorac-pentyl that may be expected to occur on

selected avian and mammalian food items imme diately following one application and multiple applications are presented in the following tables (12-17). Maximum EECs were calculated based on maximum label use rates. For all uses, no mammalian or avian RQs exceed LOCs for acute or chronic exposures. This indicates that exposures of flum iclorac-pentyl are not expected

### 38 of 87 to pose a risk of mortality or reproductive eff ects to mammals or birds and the taxa for which they are surrogates (i.e., terrestrial-phase amphibians and reptiles).When maximum application rates were used to calculate RQs and no risk of concern was found, it was assumed that there

were no risks of concern at lower rate s and no further RQs were calculated.



## Single Application:

Table 12. Estimated environmental concentratio ns (dietary-based) and RQs of flumicloracpentyl on avian food items (Kenaga Values). Based on LC50 of >5322 ppm and NOAEC of 220 ppm

Use Site Applicati

on Rate (lbs ai/A) Food Item (multiplier) MaxDietaryBased

EEC (ppm) Acute RQ Chronic RQ

Soybean 0.081 short grass (240 ppm)

tall grass (135 ppm)

broadleaf plants/sm insects (110 ppm)

fruits/pods/seeds/lg insects (15 ppm) 19.44

10.94

8.91

1.22 <0.01

<0.01

<0.01

<0.01 0.09

0.05

0.04

<0.01

Cotton

Corn 0.054 short grass (240 ppm)

tall grass (135 ppm)

broadleaf plants/sm insects (110 ppm)

fruits/pods/seeds/lg insects (15 ppm) 12.96

7.30

5.94

0.81 <0.01

<0.01

<0.01

<0.01 0.05

0.03

0.03

<0.01

Golf

course

Non-crop

Residential 0.028 short grass (240 ppm)

tall grass (135 ppm)

broadleaf plants/sm insects (110 ppm)

fruits/pods/seeds/lg insects (15 ppm) 6.72

3.78

3.08

0.42 <0.01

<0.01

<0.01

<0.01 0.03

0.01

<0.01

<0.01

### 39 of 87 

## Multiple Applications:

Table 13. Estimated environmental concentratio ns (dietary-based) and RQs of flumicloracpentyl on avian food items (Kenaga Values). Based on LC50 of >5322 ppm and NOAEC of 220 ppm. A 35 day default halflife was used.

Use Site Applicati

on Rate (lbs ai/A) Food Item MaxDietaryBased

EEC (ppm) Acute RQ Chronic RQ

Soybean 0.055 x 2 short grass 240 ppm

tall grass 135 ppm

broadleaf plants/sm insects 110 ppm

fruits/pods/seeds/lg insects 15 ppm 8.22

4.35

3.48

0.68 <0.01

<0.01

<0.01

<0.01 0.04

0.02

0.02

0.00



### Table 14. Estimated environmental concentratio ns (dietary-based) and RQs of flumicloracpentyl on mammalian food items (Kenaga Values). Based on rat LD50 of >5000 ppm and reproductive NOAEC of 200 ppm.

Use Site Applicati

on Rate (lbs ai/A) Food Item MaxDietaryBased

EEC (ppm) Acute RQ Chronic RQ

Soybean 0.055 x 2 short grass 240 ppm

tall grass 135 ppm

broadleaf plants/sm insects 110 ppm

fruits/pods/seeds/lg insects 15 ppm 8.22

4.35

3.48

0.68 <0.01

<0.01

<0.01

<0.01 0.04

0.02

0.02

0.00



### Table 15. Dose-based Avian and Mammalian EECs (0.081 lbs ai/A x 2 applications at a 14 day interval)

Dose Based

EECs (mg/kg-bw) Avian Classes and Body Weights (grams) Mammalian Classes and Body weight (grams)

Small

20 Mid

100 Large

1000 15 35 1000

Short Grass

Tall Grass Broadleaf plants Fruits/pods Arthropods

Seeds 9.36

3.96

4.96

0.77

7.16

0.17 5.34

2.26

2.83

0.44

4.08

0.10 2.39

1.01

1.27

0.20

1.83

0.04 7.84

3.32

4.15

0.65

5.99

0.14 5.42

2.29

2.87

0.45

4.14

0.10 1.26

0.53

0.66

0.10

0.96

0.02

### 40 of 87 Table 16. Dose-based Avian RQs (0.081 lbs ai/A x 2 applications at a 14 day interval)

Dose Based RQs

(Dose-based EEC/adjusted LD50) Avian Acute RQs Size Class (grams)

20 100 1000

Short Grass

Tall Grass Broadleaf plants Fruits/pods Arthropods

Seeds 0.01

0.00

0.00

0.00

0.00

0.00 0.00

0.00

0.00

0.00

0.00

0.00 0.00

0.00

0.00

0.00

0.00

0.00



### Table 17. Dose-based Mammalian RQs (0.081 lbs ai/A x 2 applications at a 14 da interval)

Dose-based RQs
(dose-based EEC/LD50 or NOAEL) Small Mammal 15 grams Medium Mammal 35 grams Large Mammal 1000 grams

Acute Chronic Acute Chronic Acute Chronic

Short Grass

Tall Grass Broadleaf plants Fruits/pods Arthropods

Seeds 0.00

0.00

0.00

0.00

0.00

0.00 0.22

0.09

0.12

0.02

0.17

0.00 0.00

0.00

0.00

0.00

0.00

0.00 0.19

0.08

0.10

0.02

0.15

0.00 0.00

0.00

0.00

0.00

0.00

0.00 0.10

0.04

0.05

0.01

0.08

0.00



### KABAM-estimated acute (0.001-0.009) and chro nic (0.04-0.78) RQs based on dietary-based exposures of birds and dose-based or dietary-ba sed exposures of mammals to flumiclorac-pentyl ROCs through consumption of contaminated aqua tic prey (using conservative model inputs) did not exceed the Agency’s LOCs (see Section 3.2.1 ). Therefore, there were no acute or chronic

risk levels of concern exceedances due to bioa ccumulation from any labeled use of flumicloracpentyl.

4.1.2 Avian & Mammalian Exposure From Drinking Water

The Screening Imbibition Program (SIP v.1.0, Released June 15, 2010) was used to calculate an upper bound estimate of exposure from drinking wa ter using flumiclorac pentyl’s solubility (0.189 ppm), the most sensitive acute and chronic avian toxicity endpoints (Avian LD 50 

### >2131 mg/kg-bw and 220 ppm, respectively) and th e most sensitive acute mammalian toxicity endpoints (Rat LD 50 

### >5000 mg/kg-bw & Rat NOAEC of 20 0 ppm). Drinking water exposure alone was determined not to be a potential acut e or chronic pathway of concern for avian or mammalian species. Results for mammalian and av ian species are presen ted in the following

tables.

Table 18. Mammalian Results

Parameter Acute Chronic
Upper bound exposure (mg/kg-bw) 0.0325 0.0325
Adjusted toxicity value (mg/kg-bw) 3845.8028 246.1314
Ratio of exposure to toxicity 0.0000 0.0001

Conclusion* Drinking water exposure alone is NOT a potential

acute concern for mammals Drinking water exposure alone is NOT a potential

chronic concern for

mammals

### 41 of 87 Table 19. Avian Results

Parameter Acute Chronic
Upper bound exposure (mg/kg-bw) 0.1531 0.1531
Adjusted toxicity value (mg/kg-bw) 1535.2353 10.9148
Ratio of exposure to acute toxicity 0.0001 0.0140

Conclusion* Drinking water exposure alone is NOT a potential

acute concern for birds Drinking water exposure alone is NOT a potential

chronic concern for birds

*Conclusion is for drinking water exposure alone. This does not combine all routes of exposure. Therefore, when aggregated with other routes ( i.e ., diet, inhalation, dermal), pesticide exposure through drinking water may contribute to a total exposure that has potential for effects to non-target animals.



### 4.1.3 Terrestrial Plants

The TERRPLANT model was used to estimate risk from runoff to terrestrial plants in areas adjacent to the treated field (sheet runoff) , wetland areas (channelized runoff) and from spray drift.

Table 20. Acute RQs for listed terrestrial plants

Use Site

and Applicati

on Rate Application

Method Emergence RQs Adjacent Areas * Emergence RQs Semi-Aquatic Areas * Drift RQs Vegetative Vigor

Monocot Dicot Monocot Dicot Monocot Dicot

Soybean

0.081 ground unincorporated 0.11 0.11 0.90 0.90 <0.1 2.61

Corn

0.054 aerial 0.12 0.12 0.65 0.65 <0.1 8.71

*The NOAEC (<0.046 lbs ai/A) or EC25 (>0.046 lbs ai/A) available for seedling emergence were the

results from a one level limit test. 0.046 lbs ai/A w as used as the endpoint for RQ values. The limit test

used IMCA and had no effects over 25%.



### The LOC (1.0) was exceeded for listed terrestrial pl ants with respect to vegetative vigor for the proposed maximum application ra te (0.081 lbs ai/A for ground applications and 0.054 lbs ai/A for aerial applications) for soyb ean applications. For listed sp ecies, there are RQs of 2.61 and 8.71 for ground spray drift and drift fr om aerial application of flumiclorac-pentyl to listed dicots, respectively. For endangered terrestrial plant species, the risk in adjacent areas and semi-aquatic areas cannot be properly asse ssed for seedling emergence because no NOAEC or EC05 is available. However, using the limit test level (0.046 lbs ai/A) as a cons ervative endpoint, no risk of concern was calculated. The endpoints sele cted for vegetative vigor were the NOAEC of

0.00031 lbs ai/A for the dicot tomato and NOAEC of 0.040 lbs ai/A for the monocot onion. There is an LOC exceedance to dicot endangered plant species for aerial and ground applications of flumiclorac-pentyl. There were no exceedances for non-listed terrestrial pl ants. Rates for ground

### 42 of 87 applications would need to be <0.03 lbs ai/A a nd <0.006 lbs ai/A for aerial applications to reduce

risk below the LOC for listed dicots.

Applications may impact sensitive species in te rrestrial habitats. Thes e risks may be reduced through label changes, including decreases in maximum single applications, decreases in the number of applications allowed pe r year, removal of aerial applica tions, use of spray drift buffers and specification of coarse droplet spectra to reduce spray drift.

The Seedling Emergence study was a 14-day study. The limit test was conducted at a nominal concentration of 0.032 mg IMCA/L. No treatme nt mortalities or morphological abnormalities

were observed so low risk is assumed.

4.1.4 Beneficial insects

Flumiclorac-pentyl as practically non-toxic to honeybees, based on the honey bee acute contact

LD 50 

### >106 μg/bee. In this study, no signi ficant mortality was observed at the highest test dose. Using the exposure methodology for foliar sprays as presented in the pollinator white paper 3



### , where an application rate of 1 lb a. i./A generates a c ontact dose of 2.7 μ g a.i./bee, the highest application rate registered for this chemical (i .e., 0.081 lb a.i./A), translates to an EEC of 0.22 μg/bee. Since this value is orders of magnitude below the highest test dose of 106 μg/bee where no mortality was observed, mortality is not expe cted for honey bees exposed to flumicloracpentyl from direct spray. Given that no oral toxicity data are av ailable for adult and larval bees exposed to this chemical, there is uncertainty in the ri sks associated with oral exposures to honey

bees.

4.2. Aquatic Environment

Peak EECs were compared to acute measures of effect for flumiclorac-pentyl to derive acute RQs for fish and invertebrates (freshwater and estu arine/marine) as well as aquatic plants. Acute RQs for animals and RQs for plants do not exceed LOCs ( Table 21 ).

Table 21. Acute and chronic RQs for fish, aquatic invertebrates & aquatic plants

Acute Effects Chronic Effects

Use site Taxa Toxicity

Reference Value (ppm) Peak

EEC RQ Toxicity

Reference Value (ppm) Chronic

EEC Chronic

Max. rate Freshwater fish 1.1 0.003 No data 0.0014 n/a

ground Freshwater invertebrate >0.189 0.00336 0.017 0.67 0.0024 0.003

Estuarine fish >24 <0.001 No data 0.0014 n/a

Estuarine invertebrate 0.56 0.006 0.22 0.0024 0.011

Aquatic plant 0.035 0.096 0.035 0.0034 0.097

3 USEPA, PMRA, and CADPR (2012) White paper in support of the proposed risk assessment process for bees.

United States Environmental Protectio n Agency, Office of Pesticide Program s, Washington DC. Pest Management Regulatory Agency, Health Canada, Ottawa. California Department of Pesticide Regulation, Sacramento, CA.

### 43 of 87 There are no chronic toxicity te sts for fish (freshwater and estuarine/marine) for Flumicloracpentyl, which leads to uncertainty in the evalua tion of chronic aquatic organism risk. This uncertainty is compounded by the fact that this chemical is an LDPH, wh ich would suggest that chronic toxicity would be increased for fish in ar eas with intense light (similar to sunlight). The degree to which toxicity could be enhanced by higher intensity light is unclear, but toxicity could be sufficiently enhanced to affect risk conclusions.

4.3. Incident Database Review

Incidents are maintained and catalogued by EFED in the Ecological Incident Information System (EIIS). There is only one ecological incident in the EIIS database that was associated in any way with flumiclorac-pentyl. In th at incident, there was damage to a soybean crop after application of a product containing flumiclora c-pentyl. However the report notes that the damage was believed to have been caused by residual contam ination from a prior use of the tank involving 2,4-D, and therefore was not due to flumiclorac-pe ntyl. Thus, the incident data give no evidence of this active ingredie nt causing any problems to non-target species. However, given that the number of incidents thought to occur in the environm ent relative to the number of incidents reported to the Agency is so low, lack of reporte d incidents does not necessarily reflect lack of risk to non-target species.

4.4. Endocrine Disruptor Screening Program

As required by FIFRA and FFDCA, EPA reviews num erous studies to asse ss potential adverse outcomes from exposure to chemicals. Collectiv ely, these studies includ e acute, subchronic and chronic toxicity, including asse ssments of carcinogenicity, ne urotoxicity, developmental, reproductive, and general or systemic toxicity. These studies include e ndpoints which may be susceptible to endocrine influe nce, including effects on endocri ne target organ histopathology, organ weights, estrus cyclicity, sexual maturatio n, fertility, pregnancy rates, reproductive loss, and sex ratios in offspring. For ecological hazard assessments, EPA evaluates acute tests and chronic studies that assess gr owth, developmental and reprod uctive effects in different taxonomic groups. As part of its most recent registration de cision for flumiclorac-pentyl, EPA

reviewed these data and select ed the most sensitive endpoints for relevant risk assessment scenarios from the existing hazard database. However, as required by FFDCA section 408(p), flumiclorac-pentyl is subject to the endocrine screening part of th e Endocrine Disruptor Screening Program (EDSP).

EPA has developed the EDSP to determine whet her certain substances (including pesticide active and other ingredients) may have an effect in humans or wildlife similar to an effect produced by a “naturally occurring estrogen, or ot her such endocrine effect s as the Administrator may designate.” The EDSP employs a two-tiered approach to making th e statutorily required

determinations. Tier 1 consists of a battery of 11 screening assays to identify the potential of a chemical substance to interact with the estrog en, androgen, or thyroid (E, A, or T) hormonal systems. Chemicals that go th rough Tier 1 screening and are found to have the potential to interact with E, A, or T hormonal systems will proceed to the next stag e of the EDSP where EPA will determine which, if any, of th e Tier 2 tests are necessary base d on the available data. Tier 2

### 44 of 87 testing is designed to identify a ny adverse endocrine-related eff ects caused by the substance, and establish a dose-response relationship between the dose and the E, A, or T effect.

Under FFDCA section 408(p), the Agency must screen all pesticide chemicals. Between October 2009 and February 2010, EPA issued test orders/data call-ins for the first group of 67 chemicals, which contains 58 pest icide active ingredient s and 9 inert ingredients. A second list

of chemicals identified for EDSP sc reening was published on June 14, 2013 4 

### and includes some pesticides scheduled for registration review and chemicals found in water

. Neither of these lists

should be construed as a list of know n or likely endocri ne disruptors.

For further information on the status of the ED SP, the policies and procedures, the lists of chemicals, future lists, the test guidelines and the Tier 1 screening batt ery, please visit our

website. 5



### 4.5. Risk Description

Risk characterization is the integration of e xposure and ecological effects characterization to determine the potential ecological risk from the us e of flumiclorac-pentyl as a herbicide and the

likelihood of direct and indirect e ffects to non-target organisms in a quatic and terrestrial habitats. The exposure and toxicity effects data are integrated in order to evaluate the risks of adverse ecological effects on non-target spec ies. For the assessment of flum iclorac-pentyl risks, the risk quotient (RQ) method is used to compare exposur e and measured toxicity values. EECs are divided by acute and chronic toxicity values. The resulting RQs are then compared to the Agency’s Levels of Concern (LOCs) (U.S. EPA 2004) . These criteria are used to indicate when flumiclorac-pentyl’s uses, as directed on the label, have the potential to cause adverse direct or indirect effects to non-target organisms. In addition, incident data from the EIIS will be considered as part of th e risk characterization.

4.5.1 Terrestrial Environment

No avian or mammalian acute or chronic LOCs were exceeded from any maximum single or multiple application of flumiclorac-pentyl. Drinking water exposure alone was determined not to be a potential acute pathway of c oncern for either avian or mammalian species.

Flumiclorac-pentyl will be applied by ground and aerial application that may result in drift to non-target plant species. Flumiclo rac-pentyl shows low toxicity to germinating seeds in seedling emergence tests (MRID 43104701). The primary degrad ate of flumiclorac-pentyl, IMCA, is also not toxic to germinating seeds (MRID 43240801). Vegetative vigor toxi city tests on lettuce, radish, tomato, cucumber, cabbage, ryegrass, co rn, and onion showed phytotoxic effects but did not on soybean and oats. Only the parent com pound, flumiclorac-pentyl, was addressed in the terrestrial plant risk assessment.

4 See http://www.regulations.gov/#!documentDetail;D=EPA-HQ-OPPT-2009-0477-0074 for the final second list of

chemicals.

5 http://www.epa.gov/endo/

### 45 of 87 Risks were not of concern for non-listed terr estrial plants. However, the LOC (1.0) was exceeded for listed terrestrial plants with respect to vegetative vigor for the proposed maximum application rate (0.081 lbs ai/A for ground applications a nd 0.054 lbs ai/A for aerial applications) for soybean & corn applicat ions, respectively. For listed species, there are RQs of 2.61 and 8.71 for ground spray drift and drift from aeria l application of flumiclorac-pentyl, respectively.

The model AgDRIFT (v2.1.1) was used to calculat e the spray drift buffe rs needed to reduce terrestrial plant exposure to be low the toxicity thresholds fo r listed plant species (tomato Lycopersicon esculentum , NOAEC = 0.00031 a.i. lb/acre). A Ti er 1 analysis was performed.

For ground application buffers, the following input pa rameters were used. A high-boom sprayer, producing very fine to fine spray droplets and the 90 th 

### percentile of drift was assessed (default assumptions). For a ground application rate of 0.081 lb/A, the highest single application rate without spray droplet size restrictions (appe aring on EPA Reg. 59639-100), the listed plant buffer

is 509 feet.

For aerial application, ASAE medium to coarse spray and an app lication rate of 0.054 lbs ai.A were assessed because EPA Reg. 59639-82, the only registered label that allows aerial application, requires medium droplet sizes and this application rate limit fo r aerial applications. For listed plant species, the calculated buffer is 876 feet. Applications may impact sensitive species of plants in terrestrial habitats. In ge neral, AgDRIFT distance estimations are affected by application rates, number of annual applications, application methods ( i.e. , ground versus aerial), buffers, and spray droplet size.

4.5.2 Aquatic Environment

Maximum EECs for ground applications of field corn (ground applicatio ns are allowed at a higher application rate, resulting in higher EECs for field corn use) were used to calculate RQs for aquatic organisms (acute risk to fish, acute an d chronic risk to aquatic invertebrates as well as risk to aquatic plants). Since there were no ri sks of concern to any aquatic organisms, no other lower application rates were assessed. However, there were no submitted chronic data for either

freshwater or estuarine/marine fish. In additi on, no data using enhanced lighting were available. Since flumiclorac-pentyl may be more toxi c under enhanced UV lighting and no chemicalspecific data were available, the potential risk to these organisms is uncertain.

Because of this limited data set, other avenues to assess risk were explored. ECOSAR was used to generate QSAR estimates for flumiclorac-pe ntyl and its degradates. The QSAR estimates didn’t track well with the measured values (the re were only a few definitive tox values for comparison). Another phthalimide herbicide similar to flumiclorac-pentyl that is registered in

the United States is flumioxazi n (chemical structure is in Appendix B, Table B.1 ). However, it has a nitrile group that may give it toxicitycharacteristics different than flumicloracpentyl. Other LDPH chemicals with structural similarities, such as fluthiacet-methyl, are also structurally different enough such th at their toxicity profiles cannot be assumed to be similar to that of flumiclorac-pentyl (chemical structures are in Appendix B, Table B.1 ). Therefore, there are no structurally similar herbicides with data submitted to EPA that can be used to infer

### 46 of 87 toxicity values for flumiclorac- pentyl residues of concern with any measure of confidence. In the absence of chronic data for fish species a nd no usable surrogate data, risk could not be calculated for those organisms.

The toxicity and exposure profile s of flumiclorac-pentyl resi dues of concern were also

considered to evaluate whether the chronic risk to fish can be assumed lower than concern levels. Flumiclorac-pentyl is relatively unstable in moist conditions and its degradates of concern do not persist. However, residues of concern half-liv es range from 25 to 59 da ys, indicating that they may be present in water bodies for a suffici ent duration to result in chronic exposure.

Concentrations of flumiclorac-pentyl in acute toxicity tests were gr eater than the compound’s solubility limit in water (0.189 mg/L), comp licating acute to chronic endpoint value comparisons. However, a comparison was conducte d comparing the acute toxicity value for Rainbow Trout (1,100 μg/L) to the maximum chroni c EEC (1.4 μg/L), the chronic toxicity value of flumiclorac-pentyl residues to Rainbow Trout would have to be approximately 786x that of the acute toxicity value in orde r to exceed the risk level of co ncern. For non-LDPH chemicals, this may be a large enough acute-t o-chronic ratio (ACR) to assume that chronic risk to fish is low. Due to the potential increase in toxicity in the presence of UV light (which may range from a factor of one to hundreds), this ACR is potentia lly reduced, resulting in a chronic toxicity value within an order of magnitude of the chronic risk LOC. Therefore, early life-cycle freshwater UV enhanced light studies are needed to reduce th is uncertainty and to quantitatively evaluate

the chronic risk to fish.

4.5.3 Endangered Species Assessment

Based on this screening-level assessment, there ar e potential risks of di rect effects to listed terrestrial plants (and possibly freshwater and es tuarine/marine fish because no chronic toxicity data have been submitted) from the use of flumiclorac-methyl on some of its registered use sites. Listed species taxa may also be affected through indirect effects because of the potential direct effects on listed and non-listed species. Potential direct effects on listed terrestrial plants (and possibly freshwater and estuarine/marine fish because no chronic toxicity data have been submitted) from the use of flumiclorac-methyl may be associated with modification of Primary Constituent Elements (PCEs) of designated critical habitats, where such designations have been made. However, at this current stage of the Regi stration Review process, it is premature to make effects determinations for listed species until fu rther scientific analysis and refinements are conducted, based on recommendations received fro m the National Academy of Sciences’ (NAS) National Research Council (NRC) April 2013 report, available at http://www.nap.edu/cata log.php?record_id=18344 . The NAS report outlines recommendations on specific scientific and technical issues re lated to the development of pesticide risk assessments that are compliant with the Endangered Species Act (ESA) and the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA).

The EPA along with the U.S. Fish & Wildlife Se rvice (USFWS), the National Marine Fisheries Service (NMFS) (collectively, the Services), a nd the U.S. Department of Agriculture (USDA), released a summary of their implem entation plan for assessing risks of pesticides to listed species ahead of the stakeholder workshop held on N ovember 15, 2013. This plan was developed in

### 47 of 87 response to the NAS’ recommendations, including a common approach to ri sk assessment as a way of addressing scientific differences betw een EPA and the Services. During the workshop, the agencies received feedback from the public on the interim scientific approaches that were developed as part of the initial implementati on of the NAS recommendations. These approaches will be jointly implemented and vetted as part of a phased iterative process. Once fully vetted, EPA will further refine the listed species effects de termination portion of this risk assessment.

To make effects determinations for individual listed species, us eful refinements may include, but are not limited to, analyses of: 1) more detaile d, species-specific ecological and biological data; 2) more detailed and accurate in formation on flumiclorac-methyl use patterns; and 3) sub-county level spatial proximity data for the co-occurrence of potential effects areas and listed species and any designated critical habitat. Examples of such refinements are described below.

EFED is currently developing tools that are expe cted to further refine the assessment and are designed to support effects determinations for individual federally list ed species and their designated critical habitats (w here applicable). Scientific information obtained from the Services, and other reliable s ources is being collated by EFED to address all currently listed species. This information is being stored in an Office of Pesticide Programs (OPP) Pesticide Registration Information SysteM (PRISM) listed species knowledgebase. The listed species knowledgebase consists of an information repos itory that houses biological and behavioral

information relevant to individual species ( e.g. , habitat, diet, and life history, including specific temporal and spatial associations) and a documen t repository that contains supporting documents ( e.g ., USFWS recovery plans) a nd electronic information ( e.g ., GIS data files). For terrestrial taxa, biological information re levant to the assessment ( e.g ., diet and body weight) will be used to parameterize exposure estimates using a method c onsistent with currently used methods in the

T-REX and T-HERPS models.

Refinements will also include more detailed analyses of the registered uses and specific use patterns that result in either “Likely to Advers ely Affect” (LAA) or “Not Likely to Adversely Affect” (NLAA) determinations for federally li sted species. The analyses may include more information on where, when, and how flumiclorac-me thyl is used on all use sites. Actual usage data (when available) and nati onal land-cover datasets that indicate potential use sites [ e.g ., National Land Cover Dataset (NLCD), Cropland Da ta Layer (CDL)] may be used to support a more refined analysis of where flumiclorac-methyl is reasonably expected to be used. Similarly, refinements on the timing of applications and a mo re in-depth exploration of agronomic practices for flumiclorac-methyl may be incl uded as part of the refinement.

The refinements based on individu al species data; additional, de tailed usage information, when available; and recommendations from the NRC re port are expected to help to more accurately identify potential areas of effect and to better inform effects and habitat determinations for listed species and any designate d critical habitats.

### 48 of 87 5. DATA GAPS

5.1. Fate

Tables 22 and 23 identify environmental fate studies by their Master Record Identification (MRID) number that offer data for each guideline requirement, as well as study classifications

and whether or not further data are needed in or der to support risk asse ssment. An aerobic soil metabolism study of two additional soils and an anaerobic aquatic metabolism study of two

sediments and their associated waters are needed to reduce uncertainty in the risk assessment. However, these additional studies were not re quested in the Problem Formulation stage of Registration Review. Therefore, the risk assess ment proceeded in their absence with exposure model inputs that may be more conservative.

Table 22. Submitted Environmental Fate Data for Flumiclorac-pentyl

OCSPP

Guideline Data Requirement Submitted Studies (MRID) Study

Classifications Sufficient

for

EFED? Comments

835.2120 Hydrolysis 4216 9842 Acceptable Yes --

835.2240 Aqueous photolysis 42825824 Acceptable Yes --

42825825 Acceptable

835.2410 Soil photolysis 4 2825826 Acceptable Yes --

42825827 Acceptable

835.4100 Aerobic soil

metabolism 42169843 Unacceptable Yes* * A guideline-compliant study of two

additional soils is needed to reduce uncertainties but was not requested in the Problem Formulation. Therefore, the assessment proceeded in the absence of

these data. 42169844 Acceptable

43304601 Acceptable

835.4200 Anaerobic soil

metabolism (None) (Not applicable) Yes --

835.4300 Aerobic aquatic

metabolism 49063001 Acceptable Yes --

835.4400 Anaerobic aquatic

metabolism 42825829/42825830 Supplemental Yes* * A guideline-compliant study of two

sediments and their associated waters is

needed to reduce uncer tainties but was not requested in the Problem Formulation. Therefore, the assessment proceeded in the

absence of these data.

835.1230

835.1240 Adsorption/ desorption and leaching 42169847 Unacceptable Yes --

42169848 Acceptable

42825832/4298650 2 Acceptable

42825833/4298650 1 Acceptable

48753701 Non-guideline

### 49 of 87 OCSPP

Guideline Data Requirement Submitted Studies (MRID) Study

Classifications Sufficient

for

EFED? Comments

835.6100 Terrestrial field dissipation 42825836 Supplemental Yes

-- 42825837 Supplemental

42825839 Supplemental

43063601 Supplemental

46563601 Acceptable

Storage stability 4 2825834 Acceptable

42825838 Acceptable

Analytical

method in soil 42825835 Upgradeable

48904401/48753703/

49175802 Acceptable

835.6200 Analytical

method in water 48904402/ 48753704/

49175803 Acceptable

850.1730 Fish

bioconcentration 42169809/42825812 A cceptable Yes --

42169810/4282581 3 Acceptable



### Table 23. Submitted Environmental Fate Data for Degradates of Flumiclorac-pentyl

OCSPP

Guideline Data Requirement Submitted Studies (MRID; Degradate) Study

Classifications Sufficient

for EFED? Comments

835.1230 Adsorption/ desorption 42169845/49175801; IMCA Supplemental Yes

-- 42169846; AFCA Unacceptable



### 5.2. Effects

Although many submissions have been made to provi de data on the effects of flumiclorac-pentyl to aquatic and terrestrial organisms, data gaps still exist. Data gaps include the following:

 Early life-cycle freshwater and estuarine fi sh toxicity studies (Guideline 850.1400) under normal and UV enhanced light with the fathe ad and sheepshead minnow, respectively.

Enhanced toxicity to organisms may occur due to flumiclorac-pentyl being a light dependent peroxidizing herbicide. Ther efore early life-cycle studies with flumiclorac-pentyl are requested. Due to structurally similarities to parent flumiclorac-pentyl, the major degradate IMCA may also be phototoxic. This enhanced toxicity is not limited to fish, but could occur in aquatic invertebrates, plan ts, and terrestrial birds and ma mmals. This study was already required in GDCI-128724-26284. The registrant Valent USA Corporation has joined the registrant light dependent peroxidizing herbicide wo rkgroup (LDPH WG), and has technically satisfied the aforementioned DCI w ith data generated on surrogate chemicals. However, the standard fish early life-cycle study was never required for flumiclorac-pentyl

as it was for the other herbicides in the LD PH group. Thus, the Agency does not have a toxicity endpoint derived from the standard, non-enhanced lighting study to apply an LDPH safety factor (currently 29X) to fo r estimation of chronic risk to fish.

### 50 of 87 The registrant has confirmed that they will be conducting a flumiclorac-specific study with a freshwater species under enhanced lighting cond itions. Thus, the Agency is expecting a study to address this uncertainty.

6. REFERENCES

6.1. Open Literature

Birchfield, N.B., and J.E. Casi da. 1997. Protoporphyrinogen oxidase of mouse and maize: Target site selectivity and thiol effects on peroxi dizing herbicide action. Pesticide Biochemistry and Physiology 57, 36-43.

CFR 40. 2007. Code of Federal Regulations, Ti tle 40, Parts 150 to 189. Protection of the Environment. U.S. Government Printing Office.

Fletcher, J.S., J.E. Nellessen, and T.G. Pfleeger . 1994. Literature review and evaluation of the EPA food-chain (Kenaga) nomogram, an instru ment for estimating pesticide residues on plants. Environ. Tox. Chem. 13:1383-1391.

Hoerger, F. and E. E. Kenaga, 1972. Pesticide Re sidues on Plants: Correlation of Representative Data as a Basis for Estimation of their Magnit ude in the Environment. In F. Coulston and F. Korte, eds., Environmental Quality and Safety: Chemistry, Toxicology, and Technology, Georg Thieme Publ., Stuttg art, West Germany, pp. 9-28.

K-State Research and Extension. 2013. Peterson , D.E., D.E. Shoup, C.R. Thompson, and B.L.

Olson. Herbicide Mode of Action. Public ation C-715. Kansas State University Agricultural Experiment Station and Cooperative Extension Service. April 2013. http://www.ksre.ksu.edu/bookstore/pubs/c715.pdf

Matringe, M., J.-M. Camadro, P. Labbe, and R. Scalla. 1989. Protoporphy rinogen oxidase as a molecular target for diph enyl ether herbicides. Biochem. J. 260: 231-235.

OSU Extension. Undated. K.L. Smith. Weed Cont rol Guide for Ohio Field Crops. Ohio State University Extension. http://ohioline.osu.edu/weeds/weeds_13.html

U.S. Environmental Protection Agency (U .S. EPA). 1993. Wildlife Exposure Factors Handbook. EPA/600/R-13/187a, Office of Research a nd Development, Washington, D.C.

U.S. EPA. 1994. EEB Hazard Assessment Science Chapter V23031. DP 165814, 195820 and 199998. Office of Pesticide Programs. Washington, D.C.

U.S. EPA. 1998. Guidelines for Ecological Risk Assessment. Risk Assessment Forum, Office of Research and Development, Washington, D.C. EPA/630/R-95/002F. April 1998. http://cfpub.epa.gov/ncea/cfm/recordisplay.cfm?deid=30759

### 51 of 87 U.S. EPA. 2002. Guidance for Selecting Input Pa rameters in Modeling th e Environmental Fate and Transport of Pesticides, Version II . US Environmental Protection Agency, Washington DC. Online at: http://www.epa.gov/oppefed1/models water/input_guidance2_28_02.htm.

U.S. EPA. 2004. Overview of the Ecological Risk Assessment Process in the Office of Pesticide Programs. U.S. Environmental Protection Ag ency, Office of Prevention, Pesticides and Toxic Substances, Office of Pesticide Programs, Washington DC. January 23, 2004.

U.S. EPA. 2005a. Environmental Fate and Effects Science Chapter, Environmental Fate and Ecological Risk Assessment, Registrati on for New Use for Flumiclorac-pentyl

. PC Code 128724. DP Barcode D311964. October 31, 2005. Environmental Fate and Effects

Division. Office of Pesticide Programs. Washington, D.C.

U.S. EPA. 2005b. Flumiclorac-pentyl: Tolerance Reassessment Decision for Low Risk Pesticide; Notice of Availability. EPA-HQ-OPP-2005-0229-0001. October 19, 2005. Office of Pesticide Programs. Washington, D.C.

U.S. EPA. 2005c. Report of the Food Quality Protection Act (FQPA) Tolerance Assessment Progress and Risk Management Decision (TRED)

. EPA-HQ-OPP-2005-0229-0002. September 15, 2005. Office of Pestic ide Programs. Washington, D.C.

U.S. EPA. 2005d. HED Chapter of the TRED

. EPA-HQ-OPP-2005-0229-0003. September 15,

2005. Health Effects Division. Office of Pe sticide Programs. Washington, D.C.

U.S. EPA. 2005e. Flumiclorac-pentyl Chronic Dietary Assessment for the TRED

. EPA-HQOPP-2005-0229-0004. September 15, 2005. Health Effects Division. Office of Pesticide Programs. Washington, D.C.

U.S. EPA. 2005f. Flumiclorac-pe ntyl Residue Chem for the TRED

. EPA-HQ-OPP-2005-0229- 0005. September 15, 2005. Office of Pes ticide Programs. Washington, D.C.

U.S. EPA. 2005g. Flumiclorac-pentyl TRED Product Chem Considerations

. EPA-HQ-OPP2005-0229-0006. September 15, 2005. Office of Pe sticide Programs. Washington, D.C.

U.S. EPA. 2005h. Flumiclorac-pentyl Tier 1 Drinking Water Assessment

. EPA-HQ-OPP-2005- 0229-0007. September 15, 2005. Office of Pest icide Programs. Washington, D.C.

U.S. EPA. 2005i. Flumiclorac-pent yl EFED Addendum No. 1 to MRID#42169844

. EPA-HQOPP-2005-0229-0008. September 15, 2005. Environm ental Fate and Effects Division. Washington, D.C.

U.S. EPA. 2005j. Flumiclorac-pent yl EFED Addendum No. 1 to MRID 43304601

. EPA-HQOPP-2005-0229-0009. September 15, 2005. Environm ental Fate and Effects Division. Office of Pesticide Programs. Washington, D.C.

### 52 of 87 U.S. EPA. 2007a. Ecological Incident Information System. http://www.epa.gov/espp/consultation/ecorisk-overview.pdf

U.S. EPA. 2007b. 40 CFR Part 158. Pesticides; Da ta Requirements for Conventional Chemicals: Final Rule. 72 FR 60934. October 26, 2007.

U.S. EPA. 2008. Usage/Use Report Package in S upport of Registration Review for Flumicloracpentyl. September 2008. Biological and Economic Analysis Division. Office of Pesticide Programs. Washington, DC.

U.S. EPA. 2009. ECOTOXicology Database. Offi ce of Research and Development National

Health and Environmental Effects Research Laboratory’s (NHEERL’s) Mid-Continent Ecology Division (MED). http://cfpub.epa.gov/ecotox/

U.S. EPA. 2014. Donovan, W. and J. Liccione. Flumiclorac pentyl: Recommendation for the Residue of Concern in Drinking Water. DP barcode 417544. Office of Pesticide Programs, Health Effects Division. Memorandu m to G. Orrick, Environmental Fate and Effects Division. Jan. 27, 2014.

U.S. Fish and Wildlife Service (USFWS) and National Marine Fisheries Service (NMFS). 1998. Endangered Species Consultation Handbook: Pr ocedures for Conducting Consultation

and Conference Activities Under Section 7 of the Endangered Species Act. Final Draft.

March 1998.

USFWS/NMFS. Letter providing an evaluation by the U.S. Fish and Wildlife Service and

National Marine Fisherie s Service of an approach to a ssessing the ecological risks of pesticide products. From Steve Williams and William Hogarth to Susan Hazen. January 26, 2004.

6.2. Submitted Environmental Fate an d Product Chemistry Studies

MRID Citation Reference

42169809 Ohshima, M.; Mikami, N. (1991) Uptake, Depuration and Bio- concentration of 14 C-PH-S-23031 to Bluegill Sunfish (Lepomis macrochirus): Lab Project Number: ACC90001A. Unpublished study prepared by Sumitomo Chem ical Co., Ltd. 41 p.

42169810 Ohshima, M.; Mikami, N. (1991) Uptake, Depuration and Bioconcentration of 14 C-THP-S-23031 to Bluegill Sunfish (Lapomis macrochirus): La b Project Number: ACC90001B. Unpublished study prepared by Sumitomo Chem ical Co., Ltd. 41 p.

42169842 Horvath, M.; Korsch, B. (1991) A Hydrolysis Study of S-23031 Experimental Herbicide: Lab Project Number: 89-0122. Unpublished study prepared by Ricerca, Inc. 295 p.

42169844 Hardies, D. (1991) An Aerobic Soil Metabolism Study with S-23031, an Experimental Herbicide,

Ph- 14 C-S-23031 as the Test Substance: Lab Project Number: 89-0119. Unpublished study prepared by Ricerca, Inc. 291 p.

42169845 Waller, R. (1991) Preliminary Adsorption and De sorption of IMCA to Soils: Lab Project Number: 91-0089. Unpublished study prepared by Ricerca, Inc. 76 p.

### 53 of 87 42169848 Korsch, B. (1991) An Unaged Soil Column Leaching Study with THP- 14 C-V-23031: Lab Project Number: 89-0383. Unpublished study prepared by Ricerca, Inc. 170 p.

42187405 Pesselman, R.; Yamada, H.; Sweetapple, G.; et al. (1991) Physical and Chem ical Characteristics of V-23031 Technical: Lab Project Number: 91-031-02. Unpublished study prepared by Ricerca, Inc., Sumitomo Chemical Co., Ltd., and Hazleton Labs. 335 p.

42825812 Ohshima, M.; Mikami, N. (1 993) Characterization of 14 C Residues in Bluegill Sunfish Treated with

14 C-PH-S-23031: Lab Project Number: ACC90001-C: SAM-20-0031. Unpublished study prepared by Sumitomo Chemical Co, Ltd. 127 p.

42825813 Ohshima, M.; Mikami, N. (1 993) Characterization of 14 C Residues in Bluegill Sunfish Treated with

14 C-PH-S-23031: Lab Project Number: ACC90001-D: SAM-20-0032. Unpublished study prepared by Sumitomo Chemical Co, Ltd. 147 p.

42825824 Korsch, B.; Lee, D.; Rose, K.; et al. (1992) A Photolysis Study of PH- 14 C-S-23031 in Water at pH 5: Lab Project Number: 3314-91-0137-EF-001. Unpublished study prepared by Ricerca, Inc. 111 p.

42825825 Korsch, B.; Lee, D.; Rose, K.; et al. (1992) A Photolysis Study of TPH- 14 C-S-23031 in Water at pH 5: Lab Project Number: 3314-91-0138-EF-001. Unpublished study prepared by Ricerca, Inc. 106 p.

42825826 Korsch, B.; Shah, J. (1992) A Photolysis Study of PH- 14 C-S-23031 on Soil: Lab Project Number: 3313-91-0139-EF-001. Unpublished study prepared by Ricerca, Inc. 132 p.

42825827 Korsch, B.; Shah, J. (1992) A Photolysis Study of TPH- 14 C-S-23031 on Soil: Lab Project Number: 3313-91-0140-EF-001. Unpublished study prepared by Ricerca, Inc. 128 p.

42825829 Hatzenbeler, C. (1992) An Anaerobic Aquatic Soil Metabolism Study with THP- 14 C-S-23031: Lab Project Number: 91-0216: 3444-91-0216-EF-001. Unpublished study prepared by Ricerca, Inc. 133

p.

42825830 Hatzenbeler, C. (1992) An Anaerobic Aquatic Soil Metabolism Study with Ph- 14 C-S-23031: Lab Project Number: 3444-89-0288-EF-001. Unpublished study prepared by Ricerca, Inc. 154 p.

42825832 Lee, D. (1992) An Aged Soil Column Leach ing Study with THP- 14 C-V-23031: Lab Project Number: 3422-91-0215-EF-001. Unpublished study prepared by Ricerca, Inc. 158 p.

42825833 Archer, G. (1992) An Aged Soil Column Leaching Study with PH- 14 C-V-23031: Lab Project Number: 3422-89-0252-EF-001. Unpublished study prepared by Ricerca, Inc. 155 p.

42825834 Cassidy, P.; Dillon, K. (1992) Stability of V-23031 in IMCA in Mississippi Soil (Data Through Five Months): Lab Project Number: 3970-91-0200: 3970-91-0200-CR-001: V-23031. Unpublished study prepared by Ri cerca, Inc. 54 p.

42825836 Kurtz, A. (1992) Field Dissipation Study with V-23031 Herbicide on Bare Ground in Mississippi: Lab Project Number: 3949-91-0182. Unpublished study prepared by Valent USA Corp. and Ricerca, Inc. 291 p.

42825837 Kurtz, A. (1992) Field Dissipation Study with V-23031 Herbicide on Bare Ground in Iowa: Lab Project Number: 3949-91-0183. Unpublished study prepared by Valent USA Corp and Ricerca, Inc. 353 p.

42825838 Cassidy, P.; Dillon, K. (1992) Stability of V-2 3031 and IMCA in Iowa Soil (Data Through Five Months): Lab Project Number: 3971-91-0201. Unpublished study prepared by Ricerca, Inc. 53 p.

42825839 Kurtz, A. (1993) Soil Dissipation of 14 C-V-23031 under Field Conditions in North Carolina: Lab Project Number: 10724: 599: 5025-91-0282-EF-001. Unpublished study prepared by PTRL East, Inc. and Ricerca, Inc. 315 p.

### 54 of 87 42986501 Lee, D. (1993) An Aged Soil Column Leach ing Study with PH- 14 C-V-23031: Revised ReportMRID 42825833: Lab Project Number: 3422-89-0252-EF-002. Unpublished study prepared by Ricerca, Inc. 162 p.

42986502 Lee, D. (1993) An Aged Soil Column Leach ing Study with THP- 14 C-V-23031: Revised ReportMRID 42825832: Lab Project Number: 3422-91-0215-EF-002: 3422-91-0215.F-000: Unpublished study prepared by Ricerca, Inc. 165 p.

43063601 Kurtz, A. (1993) Soil Dissipation of 14 C-V-23031 Under Field Conditions in Kentucky: Lab Project Number: 10809: 600: 5025-93-0444-EF-001. Unpublished study prepared by PTRL-East, Inc. and Ricerca, Inc. 267 p.

43304601 Huhtanen, K. (1994) An Aerobic Soil Metabolism Study with S-23031: THP- 14 C S-23031 as the Test Substance: Lab Project Number: 93/0106: 5711/93/0106/EF/001. Unpublished study prepared by Ricerca, Inc. 230 p.

46563601 Kowalsky, J. (2005) Terrestrial Field Soil Dissi pation of Flumiclorac Pentyl Ester (Resource Herbicide) on Bare Soil in California. Project Number: V/27334, 200500065. Unpublished study prepared by Valent U.S.A. Corporation. 202 p.

48753703 Nie, C. (2012) Independent Laboratory Validation of Method RM-29S-1, Determination of Flumiclorac-pentyl Ester and Its Degradate, IM CA in / on Soil. Project Number: 2012000018, 38127. Unpublished study prepared by Valent Technical Center. 72p.

48753704 Bondarenko, S. (2012) Independent Laboratory Validation of Valent's Method RM-29W-4 "Determination of Flumiclorac-pentyl Ester and Its Degradate IMCA, in Water". Project Number: 201200022, 38180. Unpublished study prepared by Valent Technical Center. 90p.

48904401 Green, C. (2012) Flumiclorac Pentyl Ester: Determination of Flumiclorac Pentyl Ester and its Degradate, IMCA, in/on Soil. Project Number: RM/29S/1, 201200276. Unpublished study prepared by Valent Dublin Laboratory. 20p.

48904402 Green, C. (2012) Flumiclorac Pentyl Ester: Determination of Flumiclorac Pentyl Ester and its Degradate, IMCA, in Water. Project Number: RM/29W/4, 201200275. Unpublished study prepared by Valent Dublin Laboratory. 20p.

49063001 Gohre, K. (2013) Flumiclorac-Pentyl Ester: Aerobic Aquatic Metabolism. Project Number: VP/38124, 201300035. Unpublished study prepared by Valent Technical Center. 298p.

49175801 Allen, R. (2013) IMCA: Calculation of Soil Ad sorption Partition Coefficients. Project Number: VP/38914. Unpublished study prepared by Valent U.S.A. Corporation. 9p.

49175802 Nie, C. (2013) Addendum: Independent Laboratory Validation of Method RM-29S-1, Determination of Flumiclorac Pentyl Ester and Its Degradate, IMCA in / on Soil. Project Number: VP/39127. Unpublished study prepared by Valent U.S.A. Corporation. 55p.

49175803 Bondarenko, S. (2013) Addendum: Independent Laboratory Validation of Valent's Method RM29W-4, Determination of Flumiclorac-pentyl este r and its Degradate, IMCA, in Water. Project Number: 38180, VP/38180, V/11/38180. Unpublished study prepared by Valent USA Corporation. 92p.

42169809 Ohshima, M.; Mikami, N. (1991) Uptake, Depuration and Bioconcentration of 14 C-PH-S-23031 to Bluegill Sunfish (Lepomis macrochirus): Lab Project Number: ACC90001A. Unpublished study prepared by Sumitomo Chem ical Co., Ltd. 41 p.

### 55 of 87 6.3. Submitted Effects Studies

Guideline: 71-1 Avian Single Dose Oral Toxicity

------------------------------------------------------------------------------------- MRID: 42169802 Llyod, D.; Hoxter, H.; Jaber, M. (1990) V-23031: Acute Oral Toxicity Study with the Bobwhite: Lab Project Number: 263-105. Unpublished study prepared by Wildlife International, Ltd. 21 p.

Guideline: 71-2 Avian Dietary Toxicity

------------------------------------------------------------------------------------- MRID: 42169803 Driscoll, C.; Foster, J.; Hoxter, K. (1991) V-23031: A Di etary LC50 Study with the Northern Bobwhite: Revised: Lab Project Number: 263-103. Unpublished study prepared by Wildlife International, Ltd. 36 p.

MRID: 42169804 Driscoll, C.; Foster, J.; Hoxt er, K.; et al. (1991) V-23031: A Dietary LC50 Study with the Mallard: Revised: Lab Project Number: 263-104. Unpublished study prepared by Wildlife International, Ltd. 36 p.

Guideline: 71-4 Avian Reproduction

------------------------------------------------------------------------------------- MRID: 42825804 Beavers, J.; Foster, J.; Grimes, J.; et al. (1992) V-23031: A Pilot Reproduction Study with the Northern Bobwhite (Colinus virginianus): Lab Project Number: 263-116. Unpublished study prepared by Wildlife International Ltd. 72

p.

MRID: 42825805 Beavers, J.; Sipler, O.; Smith, G.; et al. (1992) V-23031: A One-Generation Reproduction Study with the Northern Bobwhite (Colinus virginianus): Lab Project Number: 263-123. Unpublished study prepared by Wildlife International Ltd. 163 p.

MRID: 42825806 Beavers, J.; Sipler, O.; Smith, G.; et al. (1992) V-23031: A One-Generation Reproduction Study with the Mallard (Anas platyrhynchos): Lab Project Number: 263-124. Unpublished study prepared by Wildlife International Ltd. 161 p.

MRID: 42825807 Beavers, J.; Foster, J.; Grimes, J.; et al. (1992) V-23031: A Pilot Reproduction Study with the Mallard (Anas platyrhynchos): Lab Project Number: 263-117. Unpublished study prepared by Wildlife International Ltd. 72 p.

Guideline: 72-1 Acut e Toxicity to Freshwater Fish

------------------------------------------------------------------------------------- MRID: 42169805 Takimoto, Y. (1991) Justification of the Use of HCO-40 as a Co-Solvent in Aquatic Toxicity Tests: Lab Project Number: 91-031-04. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 6 p.

MRID: 42169806 Takimoto, Y.; Hahino, S.; Saito, S. (1989) The Acute Toxi city of S-23031 to Rainbow Trout (Salmo gairdneri): Lab Project Number: FTX-89002. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 30 p.

MRID: 42169807 Takimoto, Y.; Hagino, S.; Saito, S. (1989) The Acute Toxi city of S-23031 to Bluegill (Lepomis macrochirus): Lab Project Number: FTX-89005. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 30 p.

Guideline: 72-2 Acute To xicity to Freshwater Invertebrates

### 56 of 87 ------------------------------------------------------------------------------------- MRID: 42169808 Reed, D.; Peters, G. (1991) V-23031 Technical: A 48-Hour Flow-through Acute Toxicity Test with the Cladoceran (Daphnia Magna): Revised: Lab Project Number: 263A-108. Unpublished study prepared by Wildlife International, Ltd. 125 p.

Guideline: 72-3 Acute Toxicity to Estuarine/Marine Organisms

------------------------------------------------------------------------------------- MRID: 42568601 Flanagan, J. (1992) Letter Sent to J. Miller, Dated Nov. 6, 1992: Providing Preliminary Oyster Toxicity Data on V23031 EC Formulation. Prepared by Valent U.S.A. Corp. 3 p.

MRID: 42825809 Bettencourt, M. (1992) V-23031 Technical--Acute Toxicity to Sheepshead Minnow (Cyprinodon variegatus) Under Flow-Through Conditions: Lab Project Number: 92-5-4256. Unpublished study prepared by Springborn Lab, Inc. 61 p.

MRID: 42825810Bettencourt, M. (1993) V-23031 Technical--Acute Toxicity to Mysid Shrimp (Mysidopsis bahia) Under FlowThrough Conditions: Lab Project Number: 92-5-4272. Unpublished study prepared by Springborn Lab, Inc. 59 p.

MRID: 42825811 Dionne, E. (1992) V-23031 Technical--Acute Toxicity to Eastern Oyster (Crassostr ea virginica) Under FlowThrough Conditions: Lab Project Number: 12709-0192-6103-504: 92-7-4343. Unpublished study prepared by Springborn Lab, Inc. 62 p.

Guideline: 81-1 Acute oral toxicity in rats

------------------------------------------------------------------------------------- MRID: 42169811 Hiromori, T. (1990) Acute Oral Toxicity Study of S-23031 in Mice: Lab Project Number: 2005. Unpublished study prepared by Sumitomo Chemi cal Co., Ltd. 21 p.

MRID: 42169812 Hiromori, T. (1989) Acute Oral Toxicity Study of S-23031 in Rats: Lab Project Number: 2000. Unpublished study prepared by Sumitomo Chemi cal Co., Ltd. 21 p.

MRID: 42169813 Baldrick, P.; Healing, G. (1991) Acute Oral Toxicity to Rats of V-23031 0.83 EC: Lab Project Number: 901090D/VLT 1/AC. Unpublished study prepared by Huntingdon Research Centre Ltd. 20 p.

MRID: 43588904 Hoffman, G. (1994) Acute Oral Toxicity Study With Flumiclorac Pentyl-Lactofen 3.1 EC in Rats: Lab Project Number: 94-1001. Unpublished study prepared by Pharmaco LSR, Inc. 33 p.

MRID: 45553503 Bonnette, K. (2001) An Acute Oral Toxicity Study in Rats with V-10097: Lab Project Number: 3548.9. Unpublished study prepared by Springborn Laboratories, Inc. 43 p. {OPPTS 870.1100}

Guideline: 81-2 Acute dermal toxicity in rabbits or rats

------------------------------------------------------------------------------------- MRID: 42169814 Hiromori, T. (1989) Acute Dermal Toxicity Study of S-23031 in Rats: Lab Project Number: 2002. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 22 p.

MRID: 42169815

### 57 of 87 Baldrick, P.; Healing, G. (1991) Acute Dermal Toxicity to Rats of V-23031 0.83 EC: Lab Project Number: 901091D/VLT 2/AC. Unpublished study prepared by Huntingdon Research Centre Ltd. 17 p.

MRID: 43588905 Hoffman, G. (1994) Acute Dermal Toxicity Study With Flumiclorac Pentyl-Lactofen 3.1 EC in Rabbits: Lab Project Number: 94-1002. Unpublished study prepared by Pharmaco LSR, Inc. 24 p.

MRID: 45553501 Bonnette, K. (2001) An Acute Dermal Toxicity Study in Rats with V-10097: Lab Project Number: 3548.10. Unpublished study prepared by Springborn Laboratories, Inc. 52 p. {OPPTS 870.1200}

Guideline: 81-3 Acute inhalation toxicity in rats

------------------------------------------------------------------------------------- MRID: 42169816 Kawaguchi, S. (1990) Acute Inhalation Toxicity Study of S-23031 in Rats: Lab Project Number: 2036. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 44 p.

MRID: 42169817 Jackson, G.; Hardy, C.; Morrow, J.; et al. (1991) V-23031 0.83 EC Acute Inhalation Toxicity in Rats: Lab Project Number: VLT 12/91347. Unpublished study prepared by Huntingdon Research Centre Ltd. 101 p.

MRID: 42394401 Flanagan, J. (1992) Letter Sent to J. Miller dated June 29 , 1992: ?Concerning effects observed in an acute inhalation study conducted with V-23031 Herbicide|. Prepared by Valent U.S.A., Corp. 3 p.

MRID: 42825814 Jackson, G.; Hardy, C.; Morrow, J.; et al. (1992) V-23031 0.83 EC, Acute Inhalation Study in Rats, Four-Hour Exposure, Determination of the No-Effect Level: Supplemental: Lab Project Number: VLT 14/920395. Unpublished study prepared by Huntingdon Research Centre Ltd. 90 p.

MRID: 43588906 Hoffman, G. (1994) An Acute (4-Hour) Inhalation Toxicity Study of Flumiclorac Pentyl-Lactofen 3.1 EC in the Rat Via Nose-Only Exposure: Lab Project Number: 94-5190. Unpublished study prepared by Pharmaco LSR, Inc. 151

p.

MRID: 45553502 Bonnette, K. (2001) An Acute Nose-Only Inhalation Toxic ity Study in Rats with V-10097: Lab Project Number: 3548.11. Unpublished study prepared by Springborn Laboratories, Inc. 70 p. {OPPTS 870.1300}

Guideline: 81-4 Primary eye irritation in rabbits

------------------------------------------------------------------------------------- MRID: 42169818 Yamada, H. (1989) Primary Eye Skin Irritation Tests with S-23031 in Rabbits: Lab Project Number: 1693. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 21 p.

MRID: 42169819 Liggett, M.; McRae, L. (1991) Eye Irritation to the Rabbit of V-23031 0.83 EC: Lab Project Number: 901150D/VLT 4/SE. Un- published study prepared by Huntingdon Research Centre Ltd. 12 p.

MRID: 43588907 Hoffman, G. (1994) Primary Eye Irritation Study With Flumiclorac Pentyl-Lactofen 3.1 EC in Rabbits: Lab Project Number: 94-1003. Unpublished study prepared by Pharmaco LSR, Inc. 29 p.

MRID: 44298902 Blaszcak, D. (1997) Prim ary Eye Irritation Study with Resource 80 WP in Rabbits: Lab Proj ect Number: 96-1512: 9700125. Unpublished study prepared by Huntingdon Life Sciences. 28 p.

### 58 of 87 MRID: 45553506 Bonnette, K. (2001) A Primary Eye Irritation Study in Rabbits with V-10097: Lab Project Number: 3548.12. Unpublished study prepared by Springborn Laboratories, Inc. 42 p. {OPPTS 870.2400}

Guideline: 81-5 Primary dermal irritation

------------------------------------------------------------------------------------- MRID: 42169818 Yamada, H. (1989) Primary Eye Skin Irritation Tests with S-23031 in Rabbits: Lab Project Number: 1693. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 21 p.

MRID: 42169820 Liggett, M.; McRae, L. (1991) Skin Irritation to th e Rabbit of V-23031 0.83 EC: Lab Project Number: 901125D/VLT 3/SE. Un- published study prepared by Huntingdon Research Centre. 11 p.

MRID: 42883901 Nakanishi, T. (1992) Primary Skin Irritation Test with S- 23031 in Rabbits: Lab Project Number: 2648. Unpublished study prepared by Environmental Health Science Lab. 13 p.

MRID: 43588908 Hoffman, G. (1994) Primary Dermal Irritation Study With Flumiclorac Pentyl-Lactofen 3.1 EC in Rabbits: Lab Project Number: 94-1004. Unpublished study prepared by Pharmaco LSR, Inc. 22 p.

MRID: 44298903 Blaszcak, D. (1997) Primary Dermal Irr itation Study with Resource 80 WP in Rabbits : Lab Project Number: 96- 1511: 9700134. Unpublished study prepared by Huntingdon Life Sciences. 22 p.

MRID: 45553507 Bonnette, K. (2001) A Primary Skin Irritation Study in Rabbits with V-10097: Lab Project Number: 3548.13. Unpublished study prepared by Springborn Laboratories, Inc. 45 p. {OPPTS 870.2500}

Guideline: 81-6 Dermal sensitization

------------------------------------------------------------------------------------- MRID: 42169821 Yamada, H. (1989) Skin Sensitization Test with S-23031 in Guinea Pigs (Buehler Method): Lab Project Number: 1880. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 18 p.

MRID: 42169822 Nakanishi, T. (1989) Skin Sensitization Test with S-23031 in Guinea Pigs (Maximization Method): Lab Project Number: 1698. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 19 p.

MRID: 42169823 Parcell, B.; Healing, G. (1991) Skin Sensitization in the Guinea Pig of V-23031 0.83EC: Lab Project Number: 91722D/VLT 13/SS. Unpublished study prepared by Huntingdon Research Center Ltd. 24 p.

MRID: 42169824 Parcell, B.; Denton, S. (1991) Skin Sensitization in Guinea- Pig of V-23031 0.83 EC: Lab Project Number: 90116D/VLT 5/SS. Unpublished study prepared by Huntingdon Research Centre Ltd. 21 p.

MRID: 42169825 Piccirillo, V. (1991) Dermal Sensitization Potential of V-23031 Technical and V-23031 0.83 EC: Lab Project Number: 91-031-07. Unpublished study prepared by NPC, Inc. 5 p.

MRID: 42883902 Nakanishi, T. (1992) Skin Sensitization Test of S-23031 in Guinea Pigs: Lab Project Number: 2649. Unpublished study prepared by Environmental Health Science Lab. 17 p.

### 59 of 87 MRID: 43588909 Hoffman, G. (1994) Closed-Patch Rep eated Insult Dermal Sensitization Study With Flumiclorac Pentyl-Lactofen 3.1 EC in Guinea Pigs (Buehler Method): Lab Project Numbers: 94-1005: VP-10930. Unpublished study prepared by Pharmaco LSR, Inc. 107 p.

MRID: 45553504 Bonnette, K. (2001) A Dermal Sensitization Study in Gu inea Pigs with V-10097 Modified Buehler Method: Lab Project Number: 3548.14. Unpublished study prepared by Springborn Laboratories, Inc. 64 p. {OPPTS 870.2600}

Guideline: 82-1 Subchronic Oral Toxicity: 90-Day Study

------------------------------------------------------------------------------------- MRID: 42169826 Yoshida, Y. (1990) Three Month Subacute Toxicity Study of S-23031 by Dietary Administration in Rats: Lab Project Number: 1632. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 443 p.

MRID: 42169827 Nakano, M. (1991) Three-Month Oral Toxicity Study of S-23031 in Dogs: Lab Project Number: 1823. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 159 p.

MRID: 42310801 Yoshida, Y. (1990) Addendum to Three Month Subacute Toxicity Study of S-23031 by Dietary Administration in Rats: Abbreviations, Historical Controls, Statistical An alyses: Lab Project Number: 1632. Unpublished study prepared by Sumitomo Chem ical Co., Ltd. 9 p.

MRID: 42310802 Nakano, M. (1991) Addendum to Three-Month Oral Toxicity Study of S-23031 in Dogs: Measurements, Statistical Methods, Historical Controls: Lab Project Number: 1823. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 8 p.

MRID: 42883903 Tamano, S. (1990) 13-Week Subchronic Oral Toxicity Study of S-23031 Pure in Rats: Lab Project Number: 8803. Unpublished study prepared by Sumitomo Chemical Company, Ltd. 583 p.

MRID: 42883904 Yamada, H. (1990) Three Month Subacute Toxicity Study of S-23031 by Dietary Administration in Mice: Lab Project Number: 1650. Unpublished study prepared by Sumitomo Chemical Company, Ltd. 157 p.

Guideline: 82-2 21-day dermal-rabbit/rat

------------------------------------------------------------------------------------- MRID: 42825815 Osheroff, M. (1991) 21-Day Dermal Toxicity Study in Rats with S-23031: Lab Project Number: 343-229. Unpublished study prepared by Hazleton Labs America, Inc. 216 p.

MRID: 42825816 Moore, M. (1992) 21-Day Dermal Toxicity Study in Rats with V-23031 (0.83EC): Lab Project Number: 2615-100. Unpublished study prepared by Hazleton Washington, Inc. 273 p.

MRID: 43158801 Osheroff, M. (1991) 21-Day Dermal Toxicity Study in Rats with S-23031, MRID No. 42825815, Clinical Observation: Lab Project Number: 343-229. Unpublished study prepared by Hazleton Laboratories America, Inc. 101 p.

MRID: 43171801 Moore, M. (1992) 21-Day Dermal Toxicity Study in Rats with V-23031 (0.83 EC): Supplement: Lab Project Number: 2615-100. Unpublished study prepared by Hazleton Washington, Inc. 9 p.

### 60 of 87 Guideline: 83-1 Chronic Toxicity

------------------------------------------------------------------------------------- MRID: 42825817 Dalgard, D. (1992) Chronic Toxicity Study in Dogs with S-23031: Lab Project Number: 343-233. Unpublished study prepared by Hazleton Washington, Inc. 411 p.

MRID: 42883906 Adachi, H. (1992) Combined Chronic Toxicity and Oncogenicity Study of V-23031 by Dietary Administration in Rats: Lab Project Number: 1716. Unpublished study prepared by Environmental Health Science Lab. 1716 p.

MRID: 44299101 Goldenthal, E. (1997) Evaluation of (inert ingredient) in a One Year Chronic Dietary Toxicity Study in Dogs: Lab Project Number: 647-003. Unpublished study prepared by MPI Research. 186 p.

Guideline: 83-2 Oncogenicity

------------------------------------------------------------------------------------- MRID: 42883905 Adachi, H. (1992) Oncogenicity Study of S-23031 by Dietary Administration in Mice: Lab Project Number: 1842. Unpublished study prepared by Sumitomo Chemical Company, Ltd. 3771 p.

MRID: 42883906 Adachi, H. (1992) Combined Chronic Toxicity and Oncogenicity Study of V-23031 by Dietary Administration in Rats: Lab Project Number: 1716. Unpublished study prepared by Environmental Health Science Lab. 1716 p.

Guideline: 83-3 Teratogenicity -- 2 Species

------------------------------------------------------------------------------------- MRID: 42169828 Morseth, S. (1990) 5-Day Oral Toxicity Study in Fe male Rabbits with S-23031: Lab Project Number: HLA 343- 219. Unpublished study prepared by Hazleton Labs America, Inc. 71 p.

MRID: 42169829 Morseth, S. (1990) Range-Finding Rabbit Teratology Study with S-23031: Lab Project Number: HLA 343-220. Unpublished study prepared by Hazleton Labs America, Inc. 137 p.

MRID: 42169830 Lemen, J. (1991) Rabbit Teratology Study with S-23031: Lab Project Number: HLA 343-221. Unpublished study prepared by Hazleton Labs America, Inc. 231 p.

MRID: 42169831 Morseth, S. (1990) Dose-Finging Study for Teratology Study in Rats with S-23031: Lab Project Number: HLA 343- 222. Unpub- published study prepared by Hazleton Labs America, Inc. 193 p.

MRID: 42169832 Lemen, J. (1991) Rat Teratology Study with S-23031: Lab Project Number: HLA 343-223. Unpublished study prepared by Hazleton Labs America, Inc. 251 p.

MRID: 42169833 Nishimura, K. (1991) A Journal Artic le Entitled "A Micro- dissection Meth od for Detecting Thoracic Visceral Malformations in Mouse and Rat Fetuses": Lab Project Number: 91-031-03. Unpublished study prepared by Dainippon Pharmaceutical Co., Ltd. , Research Lab. 28 p.

Guideline: 83-4 2-generation repro.-rat

------------------------------------------------------------------------------------- MRID: 42169834

### 61 of 87 Nemec, M. (1990) A Dietary Dose Range-Finding Reproductive Toxicity Study of S-23031 in Rats: Lab Project Number: WIL-118007. Unpublished study prepared by WIL Research Labs., Inc. 513 p.

MRID: 42169835Nemec, M. (1991) A Dietary Two-generation Reproduction Study of S-23031 in Rats: Lab Project Number: WIL118008. Unpublished study prepared by WIL Research Labs., Inc. 2509 p.

Guideline: 83-5 Dietary: Combined Chronic To xicity/Oncogenicity Studies

------------------------------------------------------------------------------------- MRID: 42187406 Adachi, H. (1990) Combined Chronic Toxicity and Oncogenicity Study of S-23031 by Dietary Administration in Rats (52-Week Interim Report): Lab Project Number: 1716. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 1912 p.

Guideline: 84-2 Intreraction with Gonadal DNA

------------------------------------------------------------------------------------- MRID: 42169836 Kogiso, S. (1989) Reverse Mutation Test of S-23031 in Salmonella typhimurium and Escherichia coli: Lab Project Number: 1677. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 21 p.

MRID: 42169837 Hara, M. (1990) Micronucleus Test of S-23031 in ICR Mice: Lab Project Number: 2031. Unpublished study prepared by Sumitomo Chemi cal Co., Ltd. 23 p.

MRID: 42169838 Kogiso, S. (1989) In vitro Chromosomal Aberration Test of S-23031 in Chinese Hamster Ovary Cells (CHO-K1): Lab Project Number: 1875. Unpublished study prepared by Sumitomo Chemical Co. 29 p.

MRID: 42169839 Kogiso, S. (1989) In vitro Unscheduled DNA Synthesis (UDS) Assay of S-23031 in Rat Hepatocytes: Lab Project Number: 1929. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 53 p.

MRID: 42684942 Hara, M.; Kogiso, S. (1988) Micronucleus Test of S-23031 and S-53482: Lab Project Nos. 1168; 1169. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 8 p.

MRID: 42825818 Kogiso, S. (1992) Reverse Mutation Test of S-23031 in Salmonella typhimurium and Escherichia coli: Report Amendment Number One: Lab Project Number: 1677. Unpublished study prepared by Sumitomo Chemical Co, Ltd. 24 p.

MRID: 42825819 Kogiso, S. (1992) In Vitro Chromosomal Aberration Test of S-23031 in Chinese Hamster Ovary Cells (CHO-K1): Revised Reeport (sic) Number One: Lab Project Number: 1875. Unpublished study prepared by Sumitomo Chemical Co, Ltd. 31 p.

Guideline: 85-1 General metabolism

------------------------------------------------------------------------------------- MRID: 42169840 Isobe, N. (1991) Metabolism of S-23031 in Rats: Re vised: Amended Report: Lab Project Number: 1918. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 238 p.

MRID: 42825820 Radcliffe, M. (1993) Metabolism of S-23031 in Rats Revised: Revised Reeport (sic) Number One: Lab Project Number: 93-RES-011. Unpublished study prepared by Valent USA Corp, Inc. 5 p.

### 62 of 87 MRID: 42825821 Matsunaga, H. (1993) Bile Excretion Study of (Phenyl-(carbon 14))S-23031 in Male Rats: Lab Project Number: 2661. Unpublished study prepared by Sumitomo Chemical Co, Ltd. 85 p.

MRID: 42825822 Matsunaga, H. (1993) Metabolism of S-23031 in Rats: (Tetrahydrophthaloyl-1,2-(carbon 14))S-23031: Lab Project Number: 2474. Unpublished study prepared by Sumitomo Chemical Co, Ltd. 289 p.

MRID: 42825823 Matsunaga, H. (1993) Purification and Identification of Fecal and Urinary Metabolism of S-23031 in Rats: Lab Project Number: X0003. Unpublished study prepared by Sumitomo Chemical Co, Ltd. 66 p.

Guideline: 122-1 Seed Germina tion/Seedline Emergence and Vegetable Vigor

------------------------------------------------------------------------------------- MRID: 43104701 Hashimoto, S. (1994) Seed Germination Study with Metabolites of S-23031: Lab Project Number: 930260-M. Unpublished study pre- pared by Sumitomo Chemical Co., Ltd. 7 p.

MRID: 43258001 Hoberg, J. (1994) IMCA-Determination of Effects on Seedling Emergence of Ten Plant Species: Lab Project Number: 94-2-5175: VP-10812. Unpublished study prepared by Springborn Lab., Inc. 77 p.

Guideline: 122-2 Aquatic plant growth

------------------------------------------------------------------------------------- MRID: 43240801 Hoberg, J. (1994) IMCA-Acute Toxicity to the Freshwater Green Alga (Sel enastrum capricornut um): Lab Project Number: VP-10814: 94-4-5221: 12709.0294.6134.430. Unpublished study prepared by Springborn Labs., Inc. 58

p.

MRID: 43251201 Hoberg, J. (1994) IMCA-Acute Toxicity to Duckweed, Lemna gibba: Lab Project Number: VP-10819: 94-5-5255: 12709.0294.6135.410. Unpublished study prepared by Springborn Labs, Inc. 67 p.

Guideline: 123-1 Seed germination/seedling emergence and vegitative vigor

------------------------------------------------------------------------------------- MRID: 43347401 Chetram, R. (1994) Tier 2 Vegetative Vigor Nontarget Phytotoxicity Study Using Resource Herbicide: Lab Project Number: 94397: VP-11058. Unpublished study prepared by Pan-Agricultural Labs, Inc. 247 p.

Guideline: 141-1 Honey bee acute contact

------------------------------------------------------------------------------------- MRID: 42169841 Thompson, M.; Hoxter, K.; Jaber, M. (1990) V-23031: An Acute Contact Toxicity Study with the Honey Bee: Lab Project Number: 263-114. Unpublished study prepared by Wildlife International Ltd. 17 p.63 of 87Appendix A. Summary of Toxicity DataTable A1. Summary of Submitted Aquatic Toxicity Data for Flumiclorac-pentylReported Solubility of flumiclorac-pentyl is 0.189 mg/LStudyTypeTest Species(GenusSpecies)/ Flowthrough/Static% a.i.Toxicity Endpoint(Measured/Nominal)EffectMRID (Year)Classificationor SourceCommentsFreshwater VertebratesAcute850.107572-3Bluegill Sunfish(Lepomismacrochirus)/Flow-ThroughTGAI94.796-hr LC50= 17.4 mg/L(measured)1(16.5 mg ai/L)LOAEC = 13 mg/LNOAEC = 7.8 mg/L96-hr LC50> 0.189 mg/L2Mortality42169807(1989)AcceptableDER 4/29/92Test solution appearance not reported, and based onwater solubility and other studies, precipitate mayhave been present. Water was not centrifuged orfiltered before measuring concentrations.DMF:HCO-40 (1:1) solvent was present at maximumconcentrations of 3200 ppm. True exposureconcentrations cannot be determined. Sublethaleffects included abnormal respiration, loss ofequilibrium and lethargy. No sublethal effects wereobserved at 7.8 mg/L and below. Measuredconcentrations ranged from 66-78% of nominal andmortality occurred at 13 mg/L. No replicates.Acute850.107572-3Rainbow Trout(Salmo gairneri)/Flow-ThroughTGAI94.796-hr LC50= 1.1 mg/L(measured)1(1.0 mg ai/L)LOAEC = 0.87 mg/LNOAEC = 0.51 mg/L96-hr LC50> 0.189 mg/L2Mortality 42169806(1989)AcceptableDER 4/29/92Test solution appearance not reported, and based onwater solubility and other studies, precipitate mayhave been present. Water was not centrifuged orfiltered before measuring concentrations.DMF:HCO-40 (1:1) solvent was present at maximumconcentrations of 560 ppm. True exposureconcentrations cannot be determined. Sublethaleffects included swimming in surface water, onbottom orientation, loss ofequilibrium and lethargy.No sublethal effects were observed at 0.51 mg/L.Measured concentrations ranged from 87 - 94% ofnominal and mortality occurred at 0.87 mg/L andabove. No replicates.64 of 87StudyTypeTest Species(GenusSpecies)/ Flowthrough/Static% a.i.Toxicity Endpoint(Measured/Nominal)EffectMRID (Year)Classificationor SourceCommentsEstuarine/Marine VertebratesAcute850.107572-3SheepsheadMinnow(Cyprinodonvariegatus)/Flow-ThroughTGAI94.696-hr LC50> 24 mg ai/L(measured)1LOAEC > 24 mg ai/LNOAEC = 24 mg ai/L96-hr LC50> 0.189 mg/L2Mortality 42825809(1992)SupplementalDER 2/10/94Precipitate was observed in all test treatments. Waterwas not centrifuged or filtered before measuringconcentrations. DMF:HCO-40 (1:1) solvent waspresent at maximum concentrations of 4mLDMF:HCO-40/L. True exposure concentrationscannot be determined. Nosublethal effects wereobserved in any treatment group. One mortality (5%)in the solvent control and highest treatment group.Solvent Control concentration probably at maximumtolerable concentration. Measured concentrationsaveraged 95% of nominal. Two replicates.Freshwater InvertebratesAcute850.101072-3Waterflea(Daphniamagna)/Flow-ThroughTGAI94.648-hr EC50> 38.0 mg/L(measured)1(35.9 mg ai/L)LOAEC = 3.98 mg/LNOAEC = 1.88 mg/L48-hr EC50> 0.189 mg/L2Mortality 42169808(1991)AcceptableDER 5/26/92Precipitate was observed in all test treatments. Waterwas not centrifuged or filtered before measuringconcentrations. DMF:HCO-40 (1:1) solvent waspresent at maximum concentrations of 4mLDMF:HCO-40/L. True exposure concentrationscannot be determined. Sublethal effects includedlethargy, and white precipitate clinging to daphnidsin high treatment group. Measured concentrationsranged 75 to 102% of nominal. Two replicates.ChronicLife-cycleWaterflea(Daphnia magna)IMCA99.3LOAEC = >0.67 mg/LNOAEC = 0.67 mg/LNone 48848801AcceptableEstuarine/Marine InvertebratesAcute850.102572-3Eastern Oyster(Crassostreavirginica)/Flow ThroughTGAI94.696-hr EC50> 1.8 mg ai/L(measured)196-hr EC50> 0.189 mg/L2ShellGrowth42825811(1992)InvalidDER 2/10/94The test solution in the two highest testconcentrations was cloudy. Solvent concentration(DMF) was 0.5 mL DMF/L.Test concentrationsdecreased substantially during study and averaged31% of nominal. DO levels also dropped duringstudy and was 28 to 104% of saturation. Shelldeposition in controls was less than minimum 2 mm.65 of 87StudyTypeTest Species(GenusSpecies)/ Flowthrough/Static% a.i.Toxicity Endpoint(Measured/Nominal)EffectMRID (Year)Classificationor SourceCommentsAcute850.103572-3Mysid Shrimp(Mysidopsisbahia)/Flow Through<24-hr oldTGAI94.696-hr LC50= 0.56 mg ai/L(measured)NOAEC = 0.11 mg ai/LMortality 42825810(1993)AcceptableDER 1/28/94No undissolved test material was observed in thediluter system or any test solutions. SolventConcentration was 0.5mL DMF/L. Sublethal effectswere loss of equilibrium, erratic swimming anddarkened pigmentation. Measured testconcentrations ranged from 28 – 53% of nominal.Low measured test concentrations believed to be dueto degradation of flumiclorac-pentyl. Tworeplicates.ChronicLife-CycleMysid Shrimp(Mysidopsisbahia)IMCA99.3LOAEC = 0.44 mg/LNOAEC = 0.22 mg/Lprepairingandoverallsurvival48848701AcceptableAquatic Vascular and Nonvascular PlantsAcute FreshwaterDiatom(Naviculapelliculosa)IMCA NOAEC=0.88 (IMCA)EC50>0.88 (IMCA)Growth 48864401AcceptableAcute Marine Diatom(Skeletonemacostatum)IMCA NOAEC=0.41 (IMCA)EC50>0.41 (IMCA)Growth 48864501AcceptableAcute Freshwater Bluegreen Algae(Anabaena flosaquae)IMCA NOAEC=0.82 (IMCA)EC50>0.82 (IMCA)Growth 48804301AcceptableAcute850.4400122-2Duckweed(Lemna gibba)/Static-renewalIMCA398.0EC50> 0.035 mg IMCA/L(measured)Increase of 3.3% and 12.8%for frond number and dryweight, respectively, fortreatment compared tonegative controlGrowth 43251201(1994)AcceptableDER 10/24/94Study conducted for 14 days, and solutions renewedon days 3, 6, 9 and 12. Limit test conducted atnominal conc. of 0.032 mg IMCA/L.66 of 87StudyTypeTest Species(GenusSpecies)/ Flowthrough/Static% a.i.Toxicity Endpoint(Measured/Nominal)EffectMRID (Year)Classificationor SourceCommentsAcute850.5400122-2Green Algae(Selenastrumcapricornutum)IMCA398.0EC50> 0.035 mg IMCA/L(measured)Decrease of 4.1% in celldensity compared to negativecontrolGrowth 43240800(1994)AcceptableDER 10/24/94Study conducted for 120 hours. Limit test conductedat nominal conc. of 0.032 mg IMCA/L.Abbreviations: TGAI = technical gradeactive ingredient; conc.=concentration1Based on mean measured test concentrations, but due to presence of precipitate or lackof reported test solution, true test concentration not known.2LC or EC50greater than reported water solubility of 0.189 mg/L flumiclorac-pentyl.3Due to rapid degradation of flumiclorac-pentyl and major degradate IMCA being mobile in soils and possibly bioactive, study conducted with IMCA. Sinceherbicide Resource is applied at 0.0806 lbai/A and degradate IMCA is 53% of parent, the maximum application rate for IMCA was0.046 lb ai/A. When thisamount if applied to 6 inches of water a concentration of 0.032 ppm ai was calculated.Table A2. Summary of terrestrial toxicity data submitted for flumiclorac-pentylStudy TypeTest SpeciesTGAI orTEPToxicity Endpoint(95% C.I.)(Measured/Nominal)/SlopeEffectMRID (Year)Classification,DER date orsourceComments870.11Acute OralRat TGAI LD50> 5000 mg/kg Mortality 42169812U.S. EPA 2005d870.11Acute OralRat TEP0.83 ECLD50= 4100 mg/kg maleLD50= 3200 mg/kgfemaleLD50= 3600 mg/kg bothMortality 42169813U.S. EPA 2005d870.3100Subchronic Oral(90 day oral)Rat TGAI NOAEL = > 1359/1574mg/kg/day (M/F)LOAEL= not identified42169823,42310801(1990)AcceptableU.S. EPA 2005d870.4300Chronic/Carcinog-enicity ToxicityRat TGAI NOAEL = > 744.9/919.4 mg/kg/day (M/F)LOAEL = not identifiedNo evidence of carcinogenicity42883906(1992)AcceptableU.S. EPA 2005d67 of 87Study TypeTest SpeciesTGAI orTEPToxicity Endpoint(95% C.I.)(Measured/Nominal)/SlopeEffectMRID (Year)Classification,DER date orsourceComments870.4100bChronic ToxicityDog TGAI NOAEL = 100 mg/kg/dayLOAEL = 1000 mg/kg/dayDecreased body weight gain in male,increased clotting time, increased globulinlevels, increased alpha-2 fraction of theserum protein electrophoresis in females42825817(1992)AcceptableU.S. EPA 2005d870.3800Reproduction andFertility EffectsRat TGAI Reproductive NOAEL = 200 ppmLOAEL = 10,000 ppmBased on increases in pup death on day 042169835(1991)AcceptableU.S. EPA 2005dReproductive performance was notaffected in a two-generationreproduction toxicity.Avian850.2100Acute OralBobwhite Quail(Colinusvirginianus)Age=16 wks.Bw= 170-186 gTGAI94.7LD50> 2250 mg/kg-bw(nominal) (2131 mgai/kg-bw)None observed 42169802(1990)AcceptableDER 4/28/9210 birds (5 males/5 females) pertreatment. Necropsies not performed.Group weights taken rather thanindividual weights.850.2100Acute oralPasserineZebra Finch(Taeniopygiaguttata)TGAI98.3LD50> 2000 mg/kg-bw None observed 48603301AcceptableAdministered to the birds by gelatincapsule850.2200Acute DietaryBobwhite Quail(Colinusvirginianus)Age = 10 daysTGAI94.78-day LC50> 5620mg/kg-diet (nominal)(5322 mg ai/kg-diet)NOAEC = 5620 mg/kgdietNone observed 42169803(1991)Acceptable10 birds per treatment group.Measured concentration in freshlyprepared diets ranged from 83.4 to101% of nominal. Group weightsinstead of individual weights.Necropsies not conducted. Humidityless than recommended 30%,temperature was 39 ±3°C, which isgreater than recommended 35°C.850.2200Acute DietaryMallard Duck(Anasplatyrhynchos)Age = 10 dayTGAI94.78-day LC50> 5620mg/kg-diet (nominal)(5322 mg ai/kg-diet)NOAEC = 5620 mg/kgdietNone observed 42169804(1991)AcceptableDER 4/28/9210 birds per treatment group.Measured concentration in freshlyprepared diets ranged from 83.4 to101% of nominal. Group weightsinstead of individual weights.Necropsies not conducted.68 of 87Study TypeTest SpeciesTGAI orTEPToxicity Endpoint(95% C.I.)(Measured/Nominal)/SlopeEffectMRID (Year)Classification,DER date orsourceCommentsTemperature was 30 ±3°C, which islower than recommended 35°C.850.2300ReproductiveBobwhite Quail(Colinusvirginianus)Age = 32 wksTGAI94.61-generation NOAEC =439 mg ai/kg-diet(measured) (highest testconcentration tested)No mortality orreproductiveeffects attributedto treatment42825805(1992)AcceptableDER 2/4/9416 pens with one males and one female.Two mortalities in control and one intwo lowest groups, and believed to beincidental based on necropsies. Eggsstored at 13.8°C instead ofrecommended 16°C. Eggs were set at37.5°C and 56% humidity instead ofrecommended 39°C and 70%. Eighthours of light provided instead of sevenfor first seven weeks of study.Reproductive Mallard Duck(Anasplatyrhynchos)Age = 17 wksTGAI94.71-generationNOAEC= 220 mg ai/kgdiet (measured)LOAEC = 432 mg ai/kgdietDecrease in egglaying andregressed ovariesand testes42825806(1992)AcceptableDER 1/19/9416 pens with one males and one female.One mortalities lowest groups, andbelieved to be incidental based onnecropsies. Eggs stored at 13.8°Cinstead of recommended 16°C. Eggswere set at 37.5°C and 56% humidityinstead of recommended 39°C and70%. Eight hours of light providedinstead of seven for first seven weeksof study. Withdrawal period notincluded which is recommended wheneffects are observed.Terrestrial Invertebrates850.3020Acute ContactHoney Bee(Apis melliferaL.)TGAI94.7LD50> 106μg/bee No treatmentrelated mortality42169841(1990)AcceptableDER 4/14/92Bees were exposed to direct applicationof flumiclorac-pentyl in combinationwith acetone. Incidental mortalityranged from 4-12% in controls and 8-14% in treatment groups.69 of 87Study TypeTest SpeciesTGAI orTEPToxicity Endpoint(95% C.I.)(Measured/Nominal)/SlopeEffectMRID (Year)Classification,DER date orsourceCommentsTerrestrial Plants850.4100122-1SeedlingEmergenceCabbage, corncucumber,lettuce, oat,onion,perennialryegrass,soybean,tomato, turnipIMCA198.0EC25> 0.046 lb ai/ANOAEC < 0.046 lb ai/AGrowth 43258001(1994)AcceptableDER 10/24/9414-day study. Limit test conducted atnominal conc. of 0.032 mg IMCA/L.No treatment mortalities ormorphological abnormalities observedin any test species. Statisticallysignificant reduction was observed inshoot lengths of onion and oatcompared to negative control.Reduction was≤15%.850.4250123-1Vegetative VigorCorn, oat,onion,perennialryegrass,soybean,tomato,cucumber,lettuce, radishand cabbageTEP10.6EC25= 0.0027 lb ai/A –lettuce(dicot, dry weight)EC25= 0.0410 lb ai/A –onion (monocot,dryweight and height )NOAEC = 0.00031 lbai/ATomato (dicot,phytotoxicity)NOAEC = 0.040 lb ai/AOnionGrowth 43347401(1994)AcceptableDER 10/24/94EPA toxanal computer program toprovide EC50values, and slope wasused to calculate EC25values. NOAECvalues reported based on study authorsstatement since these values based onphytotoxic symptoms.1Due to rapid degradation of flumiclorac-pentyl and major degradate IMCA being mobile in soils and possibly bioactive, study conducted with IMCA. Sinceherbicide Resource is applied at 0.0806 lbai/A and degradate IMCA is 53% of parent, the maximum application rate for IMCA was0.046 lb ai/A. When thisamount if applied to 6 inches of water a concentration of 0.032 ppm ai was calculated.

### 70 of 87 

## Appendix B. Memorandum: Request for Phototoxicity Study Protocol for Light-Dependent Peroxidizing Herbicides

UNITED STATES ENVIRONMEN TAL PROTECTION AGENCY WASHINGTON, D.C. 20460

MEMORANDUM

SUBJECT: Request for Phototoxicity Study Protoc ol for Light-Dependent Peroxidizing

Herbicides

DATE: March 7, 2001

TO: Elizabeth Leovey, Acting Director

Environmental Fate and Effects Division Office of Pesticide Programs

FROM: Norman B. Birchfield, Ph.D. Thomas M. Steeger, Ph.D. Brian Montague Aquatic Biology Tech Team

The light-dependent peroxidizing herbicides (L DPHs) are a growing class of weed control chemicals (see partial listing attached). Th ey act in plants by inhibiting the enzyme protoporphyrinogen oxidase (protox), which is the last common enzyme in the heme and chlorophyll biosynthetic pathways. 6 

### Protox exists in both plants and animals and the enzyme from both sources has been shown to be highly sensitive to many LDPHs. 7

6 Matringe, M., J.-M. Camadro, P. Labbe, and R. Sca lla. 1989. Protoporphyrinogen oxidase as a molecular target for diphenyl ether herbicides. Biochem. J. 260 : 231-235.

7 Birchfield, N.B., and J.E. Casida. 1997. Protoporphyrinogen oxidase of mouse and maize: Target site selectivity and thiol effects on peroxidizing herbicide action. Pesticide Biochemistry and Physiology 57 , 36-43

.

### 71 of 87 LDPH protox inhibition in plants results in a rapid accumulation of protoporphyrin IX, a phototoxic heme and chlorophyll precursor. In the presence of light, pr otoporphyrin IX is a powerful generator of singlet oxygen which in plants causes lipid membrane peroxidation leading to a rapid loss of turgidity and folia r burns. LDPH exposure in mammals has been shown to result in excretion of porphyrins in urine (porphynuria) and f eces, increased liver weight, elevated blood porphyrin levels, developm ental abnormalities, and cancer. Humans with a hereditary protox disorder (v ariegate porphyria) which results in lowered protox activity exhibit many symptoms similar to LDPH exposure in addition to photosensitivity. However, photosensitivity is not a comm only reported symptom of LDPH exposure in animals.

An LDPH-induced occurrence of phototoxicity in rats 8 

### and increased cytotoxicity to human skin cells grown in culture in the presence of light and an LDPH 9 

### have been reported but many other LDPH toxicity studies make no mention of phototoxicity in animals. The scarcity of phototoxicity data in animals could result from physiological or biochemical distinctions from plants. For instance, animals exposed to LD PHs may not normally accumulate protoporphyrin IX in their epidermis. However, phototoxicity may not be reported in many LDPH toxicity tests because of relatively low light conditions in laboratories and/or protection afforded by the

animals' fur or feathers. Animals without fur or feathers existing in sunny environments would be expected to be at highest risk for potential phototoxic effects.

The Aquatic Biology Tech Team (ABTT) recomme nds that phototoxicity studies be conducted on herbicides with this mode of action to determ ine if animals exposed to LDPHs and intense light (similar to sunlight) show increased toxicity relative to controls ex posed to LDPHs and low intensity light. The results of these studies will help to determine if animals that are exposed to sunlight in LDPH use areas are at higher ri sk than guideline toxi city studies suggest.

The ABTT is requesting that a LDPH phototoxici ty protocol be submitted for review and agreement by EFED and the registrant prior to st udy initiation. Protocols for standard toxicity tests have also been published. 10 

### In nature, fish and other aquatic organisms are expected to be exposed to LDPHs through run-off and spray drift. Aquatic organisms inhabiting small, shallow water bodies, exposed to high levels of solar radiat ion would be expected to be at greatest risk for potential phototoxic effects. Therefore, the ABTT is requesting a small fish species be used in a phototoxicity assay to assess the potential of light to increase LDPH toxicity.

8 Halling, B.P., D.A. Yuhas, V.F. Fingar, and J.W. Winkleman. 1994. "Protoporphyrinogen oxidase inhibitors for tumor therapy" in Porphyric Pesticides: Chemistry, Toxicology, and Pharmaceutical Applications , (S.O. Duke and C.A. Rebeiz, Eds.) pp. 280-290, Ameri can Chemical Society Symposium Series 559, Am. Chem. Soc., Washington, D.C., 1994.

9 Birchfield, N.B. Protoporphyrinogen Oxidase as a Herbicide Target: Characterization of the
[ 3 H]Desmethylflumipropyn Binding Site . Dissertation. University of California, Berkeley. 1996.

10 American Society for Testing and Ma terials. 1994. Standard guide for conducting the frog embryo teratogenesis assay- Xenopus . E 1439-91. In Annual Book of ASTM Standards , Vol 11.5, pp. 825-835. Philadelphia,

PA.

### 72 of 87 The ABTT requests that the study adequately address the following issues and suggests the paper, "Photoenhanced Toxicity of a Carbamat e Insecticide to Early Life Stage Anuran Amphibians", 5 

### and other studies in the peer-reviewed sc ientific literature serve as sources of additional guidance:

Species The fathead minnow may be an appropriate test sp ecies because of existing toxicity protocols which may be adapted for this study.

Exposure duration A subchronic exposure duration would be adequate for proof of principle. A single exposure may not allow adequate time for porphyrin accu mulation, however, a life- cycle is not necessary to identify a phototoxi c effect.

Dosing A range finding study should be conducted under de fined low light conditions to identify an

LC 50 

### value and lower dose levels expected to be similar to controls. Doses used in the phototoxicity study should not be expected to result in significant mortality in low light controls.

Dissolved concentrations of the test chemical should be confirmed by an appropriate analytical

method.

Endpoints

Behavioral observations should be made in addition to measur ements of mortality, growth, weight, morphology, and appearance. Ideally, measurements of protoporphyrin and heme concentrations in the blood and protox activity in the liver of each test organisms should be

made.

Light sources Artificial light may be preferred to natural light th at will vary in different regions and seasons as

well as with weather. If artifici al light is used, the light should re semble full, natural sunlight as closely as possible, particularly around 400 nm. The most important wavelength for porphyrin induced phototoxicity in ~400 nm. No matter what the light source, the duration and intensity of UV and visible light should be reported at all wavelengths (200-800 nm). At this point EFED does not have a specific recommenda tion for an artificial light source.

Dark, light, and positive controls As this study is intended to identify potential e ffects of light on LDPH to xicity, an appropriate study protocol should include a da rk, or low light, control group. Another group not exposed to chemicals but exposed to full light should be incl uded (a full light control). In addition to the dark and light controls, a positive control group using protoporphyrin IX may be useful.

Exposure chambers and light filters Light intensity should be measured inside test ch ambers if glass or any other material is placed between the light source and the test animals. Any filters should be cured under the study light for 72-hours prior to study initiation to ensure consistent transmittance.

### 73 of 87 ATTACHMENT.

The following is a list of herbicides which ar e believed to act by inhi biting protoporphyringen

oxidase in the heme and chlo rophyll biosynthetic pathway.

acifluorfen azafenidin carfentrazone-ethyl flumiclorac-pentyl flumi oxazin fluthiacet-methyl fomesafen lactofen oxadiargyl oxadiazon oxyfluorfen sulfentrazone

thidiazimin

Table B.1. Chemical Structures of Light-Dependent Peroxidizing Herbicides

LDPH (PC code) Structure

Oxadiazon (109001)

Oxyfluorfen (111601)

Pyraflufenethyl (030090) C 3 F

Cl O O C H 2 C H 3

N O 2

### 74 of 87Flumicloracpentyl (128724) F

Cl

O

O

O N O

O



### Acifluorfen,

sodium (114402)

Carfentrazoneethyl (128712) F Cl

Cl O

O N

N N O

F F



### Flufenpyrethyl (108853)

Flumioxazin (129034)

N O N

O O F

O
C H

### 75 of 87Fluthiacetmethyl (108803)

Fomesafen (123803)

Lactofen (128888)

Sulfentrazone (129081) F F

F

Cl O N H

O S O

CH 3 

### O N + 

### O

O

### 76 of 87 

## Appendix C. Aquatic Model Calculations

PE Model Input & Output Files

128724_409810_PR A_PE_files.zip



### Total Residue of Concern Environmental Fate Calculations

128724_409810_PR A_TRcalcs.xlsx



### KABAM File

128724_409810_PRA

_KABAM_v1.0.xls

### 77 of 87 

## Appendix D. ECOTOX

Flumiclorac-pentyl Refresh Acceptable Biliography April 2013

1. Figueroa, R.; Doohan, D., and Cardina, J. Efficacy and Selectivity of Promising Herbicides for Common Groundsel Control in Newly Established Stra wberry. GRO,PHY,POPSO IL,ENV,MIXTURE; 2005; 15, (2): 261-266.

Rec #: 50 Call Number: LITE EVAL CODED (FMC), OK (MTL,PDM,SFZ,SZ)

Notes: EcoReference No.: 157325 Chemical of Concern: DMM,EFS,FMC,MTL,NPP,PDM,SFZ,SZ,TRB

2. Frans, R.; McClelland, M.; Jordan, D., and Ca rey, F. Herbicide Trials on Field Crops, 1990. PHY,POPSOIL,ENV,MIXTURE; 1991; 413, 88 p.

Rec #: 20 Call Number: LITE EVAL CODED (ATZ,FMCP), NO MIXTURE (24D,24DXY,BT,CMZ,CRM,DMB,FSF,LCF,LNR,OXF,PMT,PQT), OK (ACR,CLT,DU,FMX,MTL,NFZ,PDM,SXD,TFN), TARGET MANUAL (FNPPE), WEEDS MANUAL (FNPPE)

Notes: EcoReference No.: 73743

Chemical of Concern: 24D,24DB,24DXY,ACF,ACR,ATZ,BFL,BMN,B T,CLT,CMZ,CRM,CZE,DM B,DU,FMCP,FMU,FM X,FNPPE,FSF,FZFP,IAZ,IMQ,IZT,LCF,LNR,MB Z,MSMA,MTL,MTZ,NFZ,NSF,OXF,PDM,PMT,P QT,PTBNa,PYD,SXD,TFN,THFM

3. Nelson, K. A.; Renner, K. A., and Hammerschmidt, R. Effects of Protoporphyrinogen Oxidase Inhibitors on Soybean (Glycine max L.) Response, Sclerotinia sclerotiorum Disease Development, and Phytoalexin Production by Soybean. BCM,CEL,GRO,POP. Department of Agronomy, University of Missouri, Columbia, MO 65211//: SOIL,ENV,MIXTURE; 2002; 16, (2): 353-359.

Rec #: 10 Call Number: LITE EVAL CODED (FMC,FSF,LCF,OXF,SFZ), NO REVIEW (ACR,ALSV,ATZ,BT,CRM,DU,GYP,LN R,MOIL,PDM,PZM,SXD,SZ,TFN)

Notes: EcoReference No.: 120109

Chemical of Concern: ACF,ACR,ALSV,ATZ,BMN,BT,CRM,DU,FMC,FSF ,FTCM,GYP,IZT,LCF,LNR,MBZ,MOIL,ODZ, OXF,PDM,PZM,SFZ,SXD,SZ,TFN,THF

4. Stachler, J. M. and Kells, J. J. Wild Carrot (D aucus carota) Control in No-Tillage Cropping Systems. GRO,MOR,PHY,POPSOIL,ENV,MIXTURE; 1997; 11, (3): 444-452.

Rec #: 30 Call Number: LITE EVAL CODED (FMC,GYP), NO MIXTURE (BT,CRM,FSF,FTS,LCF,LNR,LQN,PQT), OK (ACR,ATZ,DMB,DMDP,MTL,PDM)

Notes: EcoReference No.: 117333

Chemical of Concern: 24DXY,ACF,ACO,ACR,ATZ,BMN,BT,CPR,CRM,CZE,DMB,DMDP,FMC,FSF,FTS,GYP,IMO,IM Q,IZT,LCF,LNR,LQN,MBZ,MTL,NSF,PDM,PQT,PSF,TBNU,THF

5. Ulloa, S. M. and Owen, M. D. K. Response of Asiatic Dayflower (Commelina communis) to Glyphosate and Alternatives in Soybean. BCM,GRO,PO PSOIL,ENV; 2009; 57, (1): 74-80.

Rec #: 40 Call Number: LITE EVAL CODED (CLNS,FMC,FMX,LCF,MTC), NO MIXTURE (GYPK)

Notes: EcoReference No.: 152912 Chemical of Concern: CLNS,FFC,FMC,FMX,GYPK,LCF,MBZ,MTC,PXSF

### 78 of 87 Flumiclorac-pentyl Refresh Target Bibliography April 2013

1. Altland, J. E.; Gilliam, C. H.; Oliv e, J. W.; Edwards, J. H.; Keever, G. J. ; Kessler, J. R. Jr., and Eakes, D. J. Postemergence Control of Bittercress in Contai ner-Grown Crops. GRO,PHYSOIL,ENV; 2000; 18, (1): 23-28.

Rec #: 140 Call Number: WEEDS (FMCP,IXB)

Notes: EcoReference No.: 159903 Chemical of Concern: FMCP,FTCM,IMQ,IXB

2. Brown, D. and Masiunas, J. Evaluation of Herbicides for Pumpkin (Cucurbita spp.). GRO,PHY,POP. Department of Natural Resources and Environmen tal Sciences,University of Illinois,Urbana,IL////: SOIL,ENV,MIXTURE; 2002; 16, (2): 282-292.

Rec #: 30 Call Number: OK (CMZ,SFZ), WEEDS MANUAL (FMC)

Notes: EcoReference No.: 120400 Chemical of Concern: CMZ,DMM,EFL,FMC,IZX,SFZ

3. Eyherabide, J. J. Evaluation of Flumiclorac-Pentyl in Mixtures with Low Doses of Post-Emergence Herbicides for Weed Control in Soybeans. PHY,POP. FCA,INTA,Balca rce,Argent//: SOIL,ENV; 1993; 14, 64-65.

Rec #: 150 Call Number: NO MIXTURE (BT), TARGET201 2 (BT,FMCP,FSF), WEEDS (BT,FMCP,FSF)

Notes: EcoReference No.: 159899 Chemical of Concern: 24DB,ACF,BT,FMCP,FSF

4. Fausey, J. C.; Penner, D., and Renner, K. A. Ad juvant Effects on CGA-248757 and Flumiclorac Efficacy and Crop Tolerance. PHY,POP. renner@pilot.msu. edu//Department of Crop and Soil Sciences, Michigan State University, East Lansing, MI 48824-1325, United States//: SOIL,ENV,MIXTURE; 1999; 13, (4): 783-790.

Rec #: 50 Call Number: NO MIXTURE (MTL), OK (DDVP), TARGET2012 (FMC,MTL), WEEDS (FMC,MTL)

Notes: EcoReference No.: 66128 Chemical of Concern: DDVP,FMC,FTCM,IZT,MTL

5. Fausey, J. C. and Renner, K. A. Broadleaf Weed Control in Corn (Zea mays) and Soybean (Glycine max)

with CGA-248757 and Flumiclorac Alone and in Tank Mixtures. GRO,PHY,POPSOIL,ENV,MIXTURE; 2001; 15, (3): 399-407.

Rec #: 40 Call Number: TARGET2012 (24D,24DXY,ATZ,BT,DMB,FMC,LCF), WEEDS (24D,24DXY,ATZ,BT,DMB,FMC,LCF)

Notes: EcoReference No.: 67054 Chemical of Concern: 24D,24DXY,ATZ, BMN,BT,DMB,FMC,FTCM,HSF,IZT,LCF,PSF

6. Franssen, A. S. and Kells, J. J. Common Dandelion (Taraxacum officinale) Control with Postemergence Herbicides in No-Tillage Glufosinate-Resistant Corn. POPSOIL,ENV,MIXTURE; 2007; 21, (1):

14-17.

Rec #: 60 Call Number: NO MIXTURE (DMB,FTS,GFS), TARGET2012 (ATZ,BT,DMB,DMDP,FMC,FTS,GFS), WEEDS (ATZ,BT,DMB,DMDP,FMC,FTS,GFS)

Notes: EcoReference No.: 155681

Chemical of Concern: 24DXY,ATZ,BMN,BT,CPR,DMB,DMDP,FM C,FTS,GFS,HSF,NHSO4,NSF,RIM,THF

### 79 of 87 7. Gelmini, G. A.; Victoria Filho, R.; Novo, M. C. S. S., and Adoryan, M. L. Resistance of Euphorbia heterophylla L. to ALS-Inhibiting Herbicides in Soybean. PHY,POP. Coordenadoria de Defesa Agro ecuaria,Cam inas,Brazil//: SOIL ,ENV; 2005; 62, (5): 452-457.

Rec #: 120 Call Number: WEEDS (CRME,FMCP,FSF,GFSNH,GYP,LCF)

Notes: EcoReference No.: 159905 Chemical of Concern: CRME, FMCP,FSF,GFSNH,GYP,IZT,LCF

8. Han, J.; Liu, H.; Guo, P., and Hao, C. Weed Control in Summer-Sown Soybeans with Flumioxazin plus Acetochlor and Flumiclorac-Pentyl plus Clethodim. POP. College of Agronomy,Shanxi Agricultural University,Taigu, eo . Re . China ////: SOIL,ENV,MIXTURE; 2002 ; 2, (2): 120-122.

Rec #: 170 Call Number: LITE EVAL CODED (C LT), TARGET2012 (FMCP,FMX)

Notes: EcoReference No.: 157118 Chemical of Concern: ACO,CLT,FMCP,FMX

9. Hiraki, M.; Ishida, S.; Watanabe, H.; Ogawa, H.; Kohno, H.; Boger, P., and Wakabayashi, K. Variation of Protoporphyrinogen-IX Oxidase Se nsitivity to Peroxidizing Herbicides Among Corn Varieties. MOR,PHY. Grad. Sch. Agric. Sci.,Tamagaw a Univ.,Tamagawa-Gakuen, Machida-shi, Tokyo,Japan//: SOIL,ENV; 2000; 45, (1): 7-12.

Rec #: 130 Call Number: TARGET2012 (FMCP,OXF)

Notes: EcoReference No.: 159902 Chemical of Concern: FMCP,OXF

10. Lich, J. M.; Renner, K. A., and Penner, D. Inter action of Glyphosate with Po stemergence Soybean (Glycine max) Herbicides. GRO,PHY,POP. J.M. Lich, Department of Crop and Soil Science, Michigan State University, East Lansing, MI 48824//: SO IL,ENV,MIXTURE; 1997; 45, (1): 12-21.

Rec #: 10 Call Number: OK (BT,CRM,GYP), TARGET MANUAL (FMC), WEEDS MANUAL (FMC)

Notes: EcoReference No.: 72911 Chemical of Concern: BT,CRM,FMC,FTCM,GYP,IZT,THF

11. Manley, B. S.; Wilson, H. P., and Hines, T. E. Characterization of Imidazolinone-Resistant Smooth Pigweed (Amaranthus hybridus). GRO,POP. B.S. Manley, Novartis Crop Protection, Inc., 4160 Dublin Road, Hilliard, OH 43026, United States//: SOIL,E NV,MIXTURE; 1998; 12, (4): 575-584.

Rec #: 110 Call Number: WEEDS (CRM,FMC,LCF,PDM)

Notes: EcoReference No.: 156873 Chemical of Concern: CRM,FMC,IMQ ,IZT,LCF,MBZ,NSF,PDM,PSF,PTB,THF

12. Messersmith, D. T.; Curran, W. S.; Hartwig, N. L. ; Orzolek, M. D., and Roth, G. W. Evaluation of Several Herbicides for Burcucumber (Sicyos angulatus) Cont rol in Corn (Zea mays). GRO,POP. Prof. W.S. Curran, Department of Agronomy, Penn State Un iversity, University Park, PA 16802, United States//: SOIL,ENV,MIXTURE; 1999; 13, (3): 520-524.

Rec #: 180 Call Number: WEEDS (FMC)

Notes: EcoReference No.: 62636 Chemical of Concern: FMC,HSF,PSF

13. Murphy, C. A. and Lindquist, J. L. Growth Resp onse of Velvetleaf to Three Postemergence Herbicides. GRO,MOR,REPSOIL,ENV; 2002; 50, (3): 364-369.

Rec #: 100 Call Number: WEEDS (DMB,FMC)

Notes: EcoReference No.: 159906 Chemical of Concern: DMB,FMC,HSF

### 80 of 87 14. Nandula, V. K.; Reddy, K. N.; Koger, C. H.; Poston, D. H.; Rimando, A. M.; Duke, S. O.; Bond, J. A., and Ribeiro, D. N. Multiple Resistance to Glyphosate an d Pyrithiobac in Palmer Amaranth (Amaranthus palmeri) from Mississippi and Response to Fl umiclorac. BCM,MOR,PHYSOIL,ENV,MIXTURE; 2012; 60, (2): 179-188.

Rec #: 160 Call Number: OK (ALSV,MOIL), WEEDS ( CRME,FMC,FMCP,FSF,GFS NH,GYPK,MTC,PDM)

Notes: EcoReference No.: 159891

Chemical of Concern: ALSV,CRME,FMC,FMCP,FSF, GFSNH,GYPK,MOIL,MTC,NHSO4,PDM,PTB,PTBNa

15. Terra, B. R. M.; Martin, A. R., and Lindquist, J. L. Corn-Velvetleaf (Abutilon theophrasti) Interference is Affected by Sublethal Doses of Postemergence Herbicides. GRO,PHY,POP,REPSOIL,ENV; 2007; 55, (5): 491-496.

Rec #: 90 Call Number: TARGET2012 (DMB,FMC), WEEDS (DMB,FMC)

Notes: EcoReference No.: 159907 Chemical of Concern: DMB,FMC,HSF

16. Trezzi, M. M.; Felippi, C. L.; Mattei, D.; Silva, H. L.; Nunes, A. L.; Debastiani, C.; Vidal, R. A., and Marques, A. Multiple Resistance of Acetolactate Synthase and Protoporphyrinogen Oxidase Inhibitors in Euphorbia heterophylla Biotypes. GRO,MOR. Agronomy School of CEFET/PR, Pato Branco, Brazil//: SOIL,ENV; 2005; 40, (1): 101-109.

Rec #: 20 Call Number: WEEDS (CLNS,FMC,FMX,FSF,LCF,MTS,SFZ)

Notes: EcoReference No.: 106387 Chemical of Concern: ACF,CLNS,FMC,FMX,FSF,IZT,LCF,MTS,NSF,SFZ

17. Yenish, J. P. and Eaton, N. A. Weed Control in Dry Pea (Pisum sativum) Under Conventional and No-Tillage Systems. PHY,POP. Department of Crop and Soil Sciences,Washington State University, Pullman,WA//: SOIL,ENV,MIXTURE ; 2002; 16, (1): 88-95.

Rec #: 80 Call Number: TARGET MANUAL (BT,CLNS,FMC,FSF,FTS,SFZ)

Notes: EcoReference No.: 159908 Chemical of Concern: ACO,BT,CLNS,FMC,FSF,FTS,IZT,IZX,MBZ,MCPA,SFZ

18. York, A. C.; Stewart, A. M.; Vidrine, P. R., and Cu lpepper, A. S. Control of Volunteer Glyphosate-Resistant Cotton in Glyphosate-Resistant Soyb ean. POP. Department of Cr op Science,North Carolina State University,Raleigh,NC//: SOIL,ENV,MIXTURE; 2004; 18, (3): 532-539.

Rec #: 70 Call Number: TARGET2012 (C LNS,CRM,FMC,FSF,FTS,SFZ)

Notes: EcoReference No.: 159909 Chemical of Concern: 24DB,CLNS,CRM,FMC,FSF,FTS,IMQ,MBZ,SFZ

### 81 of 87 Flumiclorac-pentyl Refresh Not Acceptable Biliography April 2013

1. Beyers, J. T.; Smeda, R. J., and Johnson, W. G. Weed Management Programs in Glufosinate-Resistant Soybean (Glycine max). PHY,POP. Agronomy Department,University of Missouri,Columbia,MO,USA//: SOIL,ENV,M IXTURE; 2002; 16, (2): 267-273.

Rec #: 90 Call Number: NO MIXTURE (BT,CLNS,FMC,FMX,LCF,PDM,SFZ), OK (GFS)

Notes: EcoReference No.: 159900 Chemical of Concern: ACF,BT,CLNS,FMC,FMX,GFS,IZT,LCF,PDM,SFZ

2. Culpepper, A. S.; Carlson, D. S., and York, A. C. Pre-Plant Control of Cutleaf Eveningprimrose (Oenothera laciniata Hill) and Wild Radish (Raphanus raphanistrum L.) in Conservation Tillage Cotton (Gossypium hirsutum L.). POPSOIL,ENV,MIXTURE; 2005; 9, (4): 223-228.

Rec #: 110 Call Number: NO ENDPOINT (GYPI,PQT), NO MIXTURE (DMDP,DU,FMCP,FMX,PMT)

Notes: EcoReference No.: 159901 Chemical of Concern: CFE,DMDP,DU,FMCP,FMX,GYPI,PMT,PQT,TBNU

3. Fausey, J. C.; Penner, D., and Renner, K. A. Physiological Basis for CGA-248757 and Flumiclorac Selectivity in Five Plant Species. ACC,CEL, GROSOIL,ENV,MIXTURE; 2000; 48, 405-411.

Rec #: 50 Call Number: NO ENDPOINT (FMC)

Notes: EcoReference No.: 59417 Chemical of Concern: FMC,FTCM

4. Fausey, J. C. and Renner, K. A. Environmenta l Effects on CGA-248757 and Flumiclorac Efficacy/Soybean Tolerance. MOR,PHYSOIL,ENV; 2001; 49, 668-674.

Rec #: 70 Call Number: NO CONTROL (FMC), NO ENDPOINT (FMC)

Notes: EcoReference No.: 63725 Chemical of Concern: FMC,FTCM

5. ---. Incorporating CGA-248757 and Flumiclorac into Annual Weed Control Programs for Corn (Zea mays) and Soybean (Glycine max). GRO,POPSOIL,ENV,MIXTURE; 2001; 15, (1): 148-154.

Rec #: 150 Call Number: NO CONTROL (FMC), NO MIXTURE (24D,24DXY,ATZ,CLT,CMZ,DMB,MTL), OK (GYP)

Notes: EcoReference No.: 66827 Chemical of Concern: 24D,24DXY,ATZ,C LT,CMZ,DMB,FMC,FTCM,GYP,IZT,MBZ,MTL,NSF

6. Frans, R.; McClelland, M.; Jordan, D., and John son, B. Herbicide Trials on Field Crops, 1989. PHY,POPSOIL,ENV,MIXTURE; 1990: 110 p.

Rec #: 130 Call Number: LITE EVAL CODED (CLT,PDM), NO MIXTURE (BT,DMB,DMDP,FMCP,FNPE,FSF,LCF,LNR,OXF,PMT), OK (ACR,ATZ,CMZ,CRME,DU,FMX ,MTL,NFZ,PQT,QZFE,SXD,TFN), TARGET MANUAL (FNPPE), WEEDS MANUAL (FNPPE)

Notes: EcoReference No.: 157119

Chemical of Concern: 24DB,ACF,ACFNa,ACR,ATZ,BFL,BMN,BT,C LT,CMZ,CRME,CZE,DMB, DMDP,DU,FMCP,FM U,FMX,FNPE,FNPPE,FSF,HFPM,IMQ,IZT,LCF ,LNR,MBZ,MSMA,MTL,MTZ,NFZ,NSF,OXF,P DM,PMT,PQT,QZFE,SXD,TFN,THFM

7. Kamoshita, K.; Nagano, E.; Saito, K.; Sakaki, M.; Yoshida, R.; Sato, R., and Oshio, H. S-23031, A New Post-Emergence Herbicide for Soybeans. POPSOIL,ENV; 1992: 317-324.

### 82 of 87 Rec #: 40 Call Number: NO CONTROL (BT,FM CP), NO ENDPOINT (BT,FMCP)

Notes: EcoReference No.: 120844 Chemical of Concern: BT,FMCP,IZT

8. Langton, S. J. Field Corn Tolerance to Acetolactate Synthase Inhibiting Herbicides and Weed Control in Sethoxydim Resistant Field Corn. ACC,GRO,POPSOIL,ENV,MIXTURE; 1997: 209 p.

Rec #: 60 Call Number: LITE EVAL CODED (DMB,SXD), NO MIXTURE (24D,24DXY,24DXYEE,ATZ,BT,CPY,DMDP,FMC,FTS,PDM,SZ,TBO)

Notes: EcoReference No.: 99110

Chemical of Concern: 24D,24DXY,24DXYEE,ACO,ATZ,BMN,BT,CPR ,CPY,DMB,DMDP,DMM,FMC,FNF,FTS,MBZ, NSF,PDM,PSF,PYD,RIM,SXD,SZ,TBO,TFT,THF

9. Legleiter, T. R. and Bradley, K. W. Glyphosa te and Multiple Herbicide Resistance in Common Waterhemp (Amaranthus rudis) Populations from Missouri. GRO,POPSOIL,ENV,MIXTURE; 2008; 56, (4):

582-587.

Rec #: 120 Call Number: NO ENDPOINT (LCF), NO MIXTURE (CLNS,FMC,FSF), OK (GYP)

Notes: EcoReference No.: 152913 Chemical of Concern: 24DB,ACF,CLNS,FMC,FSF,GYP,LCF,THF

10. Nelson, K. A. Soybean (Glycine max (L.) Merr) Growth and Development, White Mold (Sclerotinia sclerotiorum (Lib.) de Bary) Incidence, and Yello w Nutsedge (Cyperus esculentus L.) Control as Affected by Glyphosate and Other Herbicides. BCM,GRO,POP,REPSOIL,ENV,INJECT,MIXTURE; 2000: 279 p. (UMI# 9971967).

Rec #: 30 Call Number: LITE EVAL CODED (CLNS,CRM,GFS,GYPI,SFZ), NO CONC (FMC,FSF,LCF,OXF), NO MIXTURE (BT,CLT,IZP,SXD), NO REVIEW (FMC,FSF,LCF,OXF)

Notes: EcoReference No.: 120063

Chemical of Concern: ACF,BT,CLNS,CLT,CRM,FMC,FSF,FTCM,GFS,G YPI,HSF,IZP,IZT,IZX,LCF,NHSO4,ODZ,OXF ,PTB,RIM,SFZ,SXD,THF

11. Nelson, K. A. and Renner, K. A. Weed Management in Wide- and Narrow-Row Glyphosate Resistant Soybean. PHY,POP. renner@pilot.msu.edu//: SO IL,ENV,MIXTURE; 1999; 12, (3): 460-465.

Rec #: 140 Call Number: NO MIXTURE (CRM,FMC,FNP,FSF,PDM), OK (GYP)

Notes: EcoReference No.: 65280 Chemical of Concern: ACF,CRM,FMC,FNP,FSF,FZFP,GYP,IZT,MBZ,PDM,THF

12. Powell, D. K. Interaction of Postemergence Herbic ides with Glyphosate in Soybeans. SOIL; 2011: 196 p. (UMI# 1495230 ).

Rec #: 80 Call Number: NO CONTROL (FMCP,GYP), NO ENDPOINT (FMCP,GYP)

Notes: Chemical of Concern: FMCP,GYP

13. Talbert, R. E.; Schmidt, L. A.; Lovelace, M. L., an d Scherder, E. F. Field Evalua tion of Herbicides on Small Fruit, Vegetable, and Ornamental Crops, 1999. PHY,POPSOIL,ENV; 2000: 1-22.

Rec #: 20 Call Number: LITE EVAL CODED (OXF), NO ENDPOINT (GYPI,GYPT), NO MIXTURE (BT,CLNS,CMZ,FMC,FMCP,FSF,FTS,GFSNH,LCF,OYZ,QZFPE,SXD,SZ), OK (DU,LNR,MTC,MTL,PHMD,SFZ,TFN)

Notes: EcoReference No.: 153250

Chemical of Concern:

### 83 of 87 AZF,BT,CFE,CLNS,CMZ,CPR,DEF,DMM,DU,FFC,FMC,FSF,FTS,FXPM,GFSNH,GYPI,GYPT,I AZ,IZT,IZX,LCF,LNR,MTC,MTL,OXF,OYZ,PHM D,PYD,QZFPE,RIM,SFZ,SXD,SZ,TFN,TPZ,T

SF

14. Warrick, B. E. Overview of PPO Inhibitor Cotton Harvest Aids in West Central Texas. GRO,PHY. Texas Cooperative Extension,San Angelo ,TX////: SOIL,ENV; 2006: 1-4.

Rec #: 10 Call Number: NO CONTROL (ACAC,EPH, FMCP,GYPK,PQT,TBF), NO ENDPOINT (ACAC,EPH,FMCP,GYPK,PQT,TBF), TARGET2012 (ACAC,EPH,GYPK,PQT,TBF)

Notes: EcoReference No.: 159910 Chemical of Concern: ACAC,BFC,CFE ,EDT,EPH,FMCP,FTCM,GYPK,PQT,TBF,TDZ

15. Young, K. M.; Clay, P. A., and Taylor, E. L. Eval uation of Contact Herbicides as a Follow-up Treatment for Cotton Defoliation. PHY,POP. University of Arizona,Phoenix,AZ,U SA////: SOIL,ENV,MIXTURE;

2006: 1727-1730.

Rec #: 100 Call Number: NO CONTROL (DU,FMCP,PQT), NO ENDPOINT (DU,FMCP,PQT), TARGET2012 (DU,PQT)

Notes: EcoReference No.: 159904 Chemical of Concern: CFE,DU,FMCP,FTCM,PQT,TDZ

### 84 of 87 

## Appendix E. ECOSAR Estimates

Table E.1 – ECOSAR v1.11 Estimates for Fl umiclorac-pentyl and Its Degradates

Chemical Taxa Measured Tox Value (ppm ai) 1 ECOSAR estimate (ppm ai) ECOSAR class

Flumiclorac-pentyl (parent)

Log Kow = 4.99

Water solubility = 0.189 mg/L FW fish acute >0.189 1.017* Esters

FW fish chronic nd 0.041 Daphnid acute >0.189 1.534* Daphnid chronic nd 0.444*

SW fish acute >0.189 1.288*

SW fish chronic nd 0.316* Mysid acute 0.56 0.290* Mysid chronic nd 0.048 Green algae acute nd 0.407*

Earthworm acute nd 600*

FW fish acute >0.189 0.712* Imides

FW fish chronic nd 0.036 Daphnid acute >0.189 0.576* Daphnid chronic nd 0.070 Mysid acute 0.56 0.063 Green algae acute nd 0.014 Green algae chronic nd 0.074

IMCA (Flumiclorac acid)

Log Kow = 2.70 (estimated)

Water solubility = 29.0 mg/ L (estimated) FW fish acute nd 84.18* Imides-acid

FW fish chronic nd 12.41* Daphnid acute nd 86.26* Daphnid chronic >0.65 20.67* Mysid acute nd 62.24* Mysid chronic >0.44 nd Green algae acute >0.035 0.877 Green algae chronic >0.035 0.155 Blue-green algae acute >1.0 nd

FW diatom acute >1.0 nd

Marine diatom acute >1.0 nd

Lemna >0.035 nd

031-HA

Log Kow = 5.49 (estimated)

Water solubility = 0.035 mg/ L (estimated) FW fish acute nd 5.444* Esters-acid

FW fish chronic nd 0.197* Daphnid acute nd 7.792* Daphnid chronic nd 1.955*

SW fish acute nd 6.690*

SW fish chronic nd 1.796* Mysid acute nd 1.181* Mysid chronic nd 0.071* Green algae acute nd 1.909* Green algae chronic nd 1.517*

Earthworm acute nd 4333*
FW fish acute nd 1.433* Acrylamides-acid

FW fish chronic nd 0.062* Daphnid acute nd 4.315* Daphnid chronic nd 0.082*

SW fish acute nd 4.612*

SW fish chronic nd 1.059 (ACR)* Mysid acute nd 0.451*

### 85 of 87 Chemical Taxa Measured Tox Value (ppm ai) 1 ECOSAR estimate (ppm ai) ECOSAR class

031-HA (cont.) Mysid chronic nd 0.000203 Green algae acute nd 0.782* Green algae chronic nd 0.316*

IMCA-HA

Log Kow = 2.65 (estimated)

Water solubility = 25.0 mg/ L (estimated) FW fish acute nd 43.30* Acrylamides-acid

FW fish chronic nd 2.075 Daphnid acute nd 119.5* Daphnid chronic nd 1.167

SW fish acute nd 106.4*

SW fish chronic nd 15.89 (ACR) Mysid acute nd 24.914 Mysid chronic nd 0.016 Green algae acute nd 3.118 Green algae chronic nd 1.103

IMFP

Log Kow = 2.89 (estimated)

Water solubility = 44.6 mg/ L (estimated) FW fish acute nd 5.682 Imides

FW fish chronic nd 0.768 Daphnid acute nd 5.713 Daphnid chronic nd 1.296 Mysid acute nd 3.585 Green algae acute nd 0.070 Green algae chronic nd 0.013

FW fish acute nd 10.89 Phenols

FW fish chronic nd 1.252 Daphnid acute nd 4.865 Daphnid chronic nd 0.924

SW fish acute nd 4.166 Green algae acute nd 20.53 Green algae chronic nd 9.537

Lemna nd 6.245

Earthworm nd 119*

IMFP-HA

Log Kow = 3.07 (estimated)

Water solubility = 24.5 mg/ L (estimated) FW fish acute nd 84.01* Phenols-acid

FW fish chronic nd 9.917 Daphnid acute nd 40.70* Daphnid chronic nd 7.730

SW fish acute nd 31.08* Green algae acute nd 168.8* Green algae chronic nd 78.21*

Lemna nd 46.05*

Earthworm nd 1066*
FW fish acute nd 21.50 Acrylamides-acid

FW fish chronic nd 1.015 Daphnid acute nd 60.11* Daphnid chronic nd 0.648

SW fish acute nd 54.99*

SW fish chronic nd 8.754 (ACR) Mysid acute nd 11.32 Mysid chronic nd 0.007 Green algae acute nd 2.090 Green algae chronic nd 0.701

### 86 of 87 Chemical Taxa Measured Tox Value (ppm ai) 1 ECOSAR estimate (ppm ai) ECOSAR class

SAT IMFP-HA

Log Kow = 2.00 (estimated)

Water solubility = 194.3 mg/ L (estimated) FW fish acute nd 548* Phenols-acid

FW fish chronic nd 55.33 Daphnid acute nd 165 Daphnid chronic nd 31.40

SW fish acute nd 247* Green algae acute nd 759* Green algae chronic nd 357*

Lemna nd 392*

Earthworm nd 2932*

FW fish acute nd 943* Amides-acid

FW fish chronic nd 1.616 Daphnid acute nd 1038* Daphnid chronic nd 58.22

SW fish acute nd 833* Mysid acute nd 52.66 Green algae acute nd 29.65 Green algae chronic nd 27.85

FW fish acute nd 119 Phenol Aminesacid FW fish chronic nd 5.749 (ACR) Daphnid acute nd 15.58 Daphnid chronic nd 3.773 Green algae acute nd 43.66 Green algae chronic nd 9.234

AFE

Log Kow = 3.51 (estimated)

Water solubility = 14.3 mg/ L (estimated) FW fish acute nd 3.678 Anilines (Unhindered) FW fish acute (14 d) nd 0.701

FW fish chronic nd 0.018 Daphnid acute nd 2.003 Daphnid chronic nd 0.013 Green algae acute nd 1.444 Green algae chronic nd 3.046

FW fish acute nd 5.107 Esters

FW fish chronic nd 0.280 Daphnid acute nd 9.034 Daphnid chronic nd 4.005

SW fish acute nd 7.084

SW fish chronic nd 1.332 Mysid acute nd 3.316 Mysid chronic nd 11.32 Green algae acute nd 3.028 Green algae chronic nd 1.266

Earthworm nd 1234*

AFCA

Log Kow = 1.26 (estimated)

Water solubility = 7265 mg/ L (estimated) FW fish acute nd 1033 Anilines (Unhindered)-acid FW fish acute (14 d) nd 1099

FW fish chronic nd 5.672 Daphnid acute nd 15.96 Daphnid chronic nd 0.440 Green algae acute nd 37.57 Green algae chronic nd 63.68

### 87 of 87 Chemical Taxa Measured Tox Value (ppm ai) 1 ECOSAR estimate (ppm ai) ECOSAR class

AMFP

Log Kow = 1.09 (estimated)

Water solubility = 7899 mg/ L (estimated) FW fish acute nd 99.19 Anilines (Unhindered) FW fish acute (14 d) nd 120

FW fish chronic nd 0.549 Daphnid acute nd 1.178 Daphnid chronic nd 0.036 Green algae acute nd 3.028 Green algae chronic nd 5.050

FW fish acute nd 138 Phenols

FW fish chronic nd 12.20 Daphnid acute nd 27.72 Daphnid chronic nd 5.280 Green algae acute nd 139 Green algae chronic nd 66.18

SW fish acute nd 73.53

Lemna nd 124

Earthworm nd 354

FW fish acute nd 14.63 Phenol Amines

FW fish chronic nd 0.986 (ACR) Daphnid acute nd 1.211 Daphnid chronic nd 0.532 Green algae acute nd 6.111 Green algae chronic nd 0.993

THPA

Log Kow = 2.02 (estimated)

Water solubility = 2879 mg/ L (estimated) FW fish acute nd 1345 Neutral Organicsacid FW fish acute (14 d) nd 1403

FW fish chronic nd 132 Daphnid acute nd 764 Daphnid chronic nd 74.97

SW fish acute nd 1694

SW fish chronic nd 186 Mysid acute nd 1243 Mysid chronic nd 107 Green algae acute nd 662 Green algae chronic nd 151

Earthworm nd 2945*

1-OH-HPA

Log Kow = 0.060 (estimated)

Water solubility =

3.6x10 5 mg/ L (estimated) FW fish acute nd 85460 Neutral Organicsacid FW fish acute (14 d) nd 81317

FW fish chronic nd 6762 Daphnid acute nd 40673 Daphnid chronic nd 2403

SW fish acute nd 1.06 x10 5

SW fish chronic nd 3530 Mysid acute nd 2.94 x10 5
Mysid chronic nd 45193 Green algae acute nd 28697 Green algae chronic nd 2532

Earthworm nd 5200

1 nd = no data *above solubility limit, no effects expected at saturation