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 Assessment 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, Chemical Review Manager 

 Patricia Parrott, Branch Chief 

 Risk Management and Implementation Branch 3 

 Pesticide Re-evaluation Division 

The Environmental Fate and Effects Division (EFED) has completed the (attached) ecological 

risk assessment to be conducted as part of the Registration Review of the herbicide, flumicloracpentyl (PC Code 128724). Based on currently registered uses and labeled rates, this preliminary 

assessment is focused on species that are not federally listed as threatened or endangered 

(referred to as “listed). For taxa where there may be risks of concern, specific determinations for 

listed species are considered uncertain at this time. Currently labeled rates 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 distance from treated fields for which spray drift 

exposure to terrestrial plants is below the toxicity 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 application site. In general, AgDRIFT 

distance estimations are affected by application rates, number of annual applications, application 

methods (i.e., ground versus aerial), buffers, and spray droplet size. 
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Attachment: The Environmental Fate, Ecological Risk, and Endangered Species Assessment in 

Support of the Registration Review of Flumiclorac-pentyl.
3 of 87 

 

 

Preliminary Environmental Fate and Ecological Risk 

Assessment in Support of the Registration Review of 

Flumiclorac-pentyl 

F

Cl

O

O

O

N

O

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Flumiclorac-pentyl (CAS 87546-18-7)

Prepared by:

N.E. Federoff, Wildlife Biologist 

Greg Orrick, Environmental Scientist 

U. S. Environmental Protection Agency 

Office of Pesticide Programs 

Environmental Fate and Effects Division 

Environmental Risk Branch II 

1200 Pennsylvania Ave., NW 

Mail Code 7507P 

Washington, DC 20460

Reviewed by: 

James Lin, Environmental Engineer 

Kristina Garber M.S., Senior Biologist 

Jean Holmes, DVM, MPH, RAPL 

Brian Anderson, Branch Chief
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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.............................................................................................................. 13

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
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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 current uses of flumiclorac-pentyl (i.e., flumiclorac pentyl 

ester) ................................................................................................................................................ 9

Table 2. Screening-level estimates of agricultural uses of flumiclorac-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 Residues 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 from 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* ................................................................................. 34

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). Based 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 applications 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 ........................................................................... 41

Table 21. Acute and chronic RQs for fish, aquatic invertebrates & aquatic plants ...................... 42
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Table 22. Submitted Environmental Fate Data for Flumiclorac-pentyl ....................................... 48

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

Appendices 

Appendix A. Summary of Toxicity Data 63

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

Peroxidizing Herbicides 70

Appendix C. Aquatic Model Calculations 76

Appendix D. ECOTOX 77

Appendix E. ECOSAR Estimates 84

  
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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 determinations for listed species are considered uncertain 

at this time. This risk assessment incorporates the available exposure and 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-phenylphthalimide 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 Spring burndown herbicide. For non-agricultural use 

sites (including golf courses, parks, recreational areas, residential areas, schools, Christmas tree 

farms, sod farms, ornamental nurseries, industrial areas, commercial areas, rights-of-way, and 

habitat restoration and maintenance areas), it is registered 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 IMFP-HA) are assumed to have toxicity 

similar to the parent compound and are included as residues of concern. 

1.3. Environmental Fate Summary 

Flumiclorac-pentyl (i.e., flumiclorac pentyl ester) rapidly 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 readily 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 DT50 values 

of 7.3-11 days and does not photolyze. In the field, flumiclorac-pentyl dissipates with DT50

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 KOC values of 34-

100 L/kgOC. Collectively, the flumiclorac-pentyl residues of concern are moderately persistent, 

with collective biodegradation half-lives of 25-59 days. Major transport routes 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 growth 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 risk concern. The model AgDRIFT was used to 

calculate the spray drift buffers needed to reduce terrestrial plant exposure to below the toxicity 

thresholds for listed plant species. For a ground application, the listed plant buffer is 509 feet. 

For aerial application, the calculated buffer is 876 feet. 
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Major uncertainty exists due to a lack of chronic toxicity data for fish and expected increases in 

sensitivity of these species because flumiclorac-pentyl is a light-dependent peroxidizing 

herbicide. 

Risk of effects to survival, growth and reproduction are not expected for mammals, birds, 

terrestrial-phase amphibians, reptiles, and aquatic invertebrates. 

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

Mortality is not expected for honey 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 discusses the stressor, the conceptual 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 information 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 derivative 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 action, as a light-dependent peroxidizing herbicide 

(LDPH), is through the accumulation of porphyrins in susceptible plants. In turn, the 

photosensitizing action of accumulated porphyrins may cause membrane lipid peroxidation 

which leads to irreversible damage of membrane function and structure 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 and animals and the enzyme from both 

sources has been shown to be highly sensitive to many LDPHs (Birchfield and Casida, 1997). 

2.2. Stressor Source and Distribution 

Flumiclorac-pentyl is registered for post-emergence broadcast application to field corn and 

soybeans, as a defoliant on cotton, and as a Spring burndown herbicide. For non-agricultural use 

sites (including golf courses, parks, recreational areas, residential areas, schools, Christmas tree 

farms, sod farms, ornamental nurseries, industrial areas, commercial areas, rights-of-way, and 

habitat restoration and maintenance areas), it is registered for control of broadleaf weeds 

including morning glory and velvet leaf. The registered formulations include soluble 

concentrate, dust, wettable powder, granular, liquid, and pelleted or tableted (BEAD, August, 

2008). Table 1 contains the labeled use patterns of maximum exposure. 
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Table 1. Maximum use patterns for current uses of flumiclorac-pentyl (i.e., flumiclorac pentyl ester) 

Product Label 

(EPA Reg. No.); 

Formulation 

Active Ingredient 

(%) Use Site 

Max. Single 

App. Rate

(lbs a.i./A)

Max. Annual 

App. Rate 

(lbs a.i./A) A

App. 

Interval 

(d) 

Application 

Type 

A

Resource 

(59639-82); 

Emulsifiable 

Concentrate 

Flumiclorac pentyl 

ester (10.1% by wt.) 

Field corn 0.040 0.054 

14 

Aerial or 

ground 

Aer

ex

Do n

syste

fin

Soybeans 0.081 0.11 

Spring burndown B

[proposed use directions C] 

0.027 

[0.081 C] 

Not stated 

[0.11 C]

Not stated

[7 C] 

Cotton 0.054 0.094 7 Ground 

Stellar 

(59639-92); 

Emulsifiable 

Concentrate 

Flumiclorac pentyl 

ester (7.6% by wt.) 

and lactofen (26.6% 

by wt.) 

Soybeans 0.038 0.055 14 Ground Do n

Resource 80 WP 

(59639-100); 

Wettable Powder 

Flumiclorac pentyl 

ester (80% by wt.) 

Field corn 0.054 0.054 

14 Ground Do n

Soybeans 0.081 0.11 

V-10097 

(59639-122); 

Emulsifiable 

Concentrate 

Flumiclorac pentyl 

ester (0.576% by 

wt.) and glyphosate 

(40.700% by wt.) 

Field corn 0.014 0.028 

14 

Aerial or 

ground 

Do n

Cut 

made 

Do no

Soybeans 0.042 0.042 

Spring burndown B

[proposed use directions C] 0.028 Not stated [0.056 C] Not stated [7 C] 

Golf courses, parks, recreational 

areas, residential areas, schools, 

Christmas tree farms, sod farms, 

ornamental nurseries, industrial 

areas, commercial areas, rightsof-way, habitat restoration and 

maintenance areas 

[proposed use directions C] 

0.028 Not stated [0.056 C] Not stated [7 C] 

A Labels provide seasonal application rate limits that approximate annual limits. B Spring burndown uses may occur prior to or immediately after planting cotton, field corn, or soybeans. C Proposed [bracketed and footnoted] label directions are intended for the next stamped label. The current label directions are not brac
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The herbicide was first registered in 1994. There are a total of five FIFRA 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 Experimental Use Permit (EUP) and a Special Local 

Need (SLN) label that was issued to the State of Missouri. 

Flumiclorac-pentyl is applied via aircraft, ground 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 containing flumiclorac-pentyl have a wide range of 

active ingredient concentrations ranging from 0.576% ai to 80.0% ai. 

Table 2 provides estimates of the national-level agricultural usage of flumiclorac-pentyl from 

2001 to 2007 (provided by the Biological and Economic Analysis Division in OPP (BEAD)). 

Most usage was on soybeans. The uses marked with 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 application amounts that span over a 7 year period 

(2001 to 2007). As a result, cancelled uses may appear in the table. 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 percent 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 flumiclorac-pentyl in 2011, as reported by the USGS 

NAWQA program (USGS, 2014). Soybeans are consistently the use site with highest usage. 
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Figure 1. Agricultural usage of flumiclorac-pentyl in 2011 (USGS, 2014) 
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2.3. Nature of Regulatory Action 

Under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), all pesticides 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 registered, EPA evaluates its 

safety to non-target species based on a wide range 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 review1

. The 

Registration Review program is intended to ensure that, as the ability to assess risk evolves and 

as policies and practices change, all 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 reevaluates pesticides to make sure that as change 

occurs, products in the marketplace can be used safely. 

As part of the implementation of the Registration Review program pursuant to Section 3(g) of 

FIFRA, EPA is evaluating the use of flumiclorac-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 which serve as the basis for this preliminary risk 

assessment include the following: 

 October 31, 2005 EFED Risk Assessment for 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 scope; 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 may receive drift or runoff during flooding. Areas 

adjacent to the treated areas could include cultivated fields, fencerows and hedgerows, meadows, 

fallow fields or grasslands, woodlands, riparian habitats and other uncultivated areas. 

Aquatic ecosystems potentially at risk include water 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/
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waterways such as streams or rivers. For uses in coastal areas, aquatic habitat also includes 

marine ecosystems, including estuaries. 

2.6. Assessment Endpoints 

Assessment endpoints represent the actual 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 ecological entities may include the following: birds, 

mammals, terrestrial-phase amphibians, reptiles, freshwater fish and invertebrates, aquatic-phase 

amphibians, estuarine/marine fish and invertebrates, terrestrial plants, insects, 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 exposed to the stressor (U.S. EPA 1998). Consistent 

with the process described in the Overview Document (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 broad taxonomic groups, are 

used to extrapolate to potential effects on a variety of species (receptors) 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 receptors. 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 identified through EPA’s ECOTOXicology 

(ECOTOX) database (U.S. EPA 2009), which employs a literature search engine for locating 

chemical toxicity data for aquatic life, terrestrial 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 characteristics of the affected communities. Open literature citations 

from ECOTOX on flumiclorac-pentyl were reviewed and were found to contain no acceptable 

studies for inclusion in the risk assessment at this time. 

A summary of the aquatic and terrestrial toxicity data used to derive 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 and a description of ecosystems potentially at risk 

are provided in Sections 4.3 and 4.5, respectively. 

2.8. Risk Hypothesis 

A risk hypothesis describes the predicted relationship among the stressor, exposure, and 

assessment endpoint response along with the rationale for their selection. For flumicloracpentyl, the following overall ecological risk hypothesis is being employed for this ecological risk 

assessment: 
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Based on the application methods, mode of action, fate and transport, and the sensitivity of nontarget aquatic and terrestrial species, flumiclorac-pentyl and its six major degradates with an 

intact imido/amide bridge (IMCA (flumiclorac acid), 031-HA, IMCA-HA, IMFP, IMFP-HA, and 

SAT IMFP-HA) have the potential to reduce survival and growth in non-target terrestrial plants 

when used in accordance with the current label. 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 peroxidizing herbicide), and known sensitivity of nontarget aquatic and terrestrial species to this class of chemicals, flumiclorac-pentyl and its six 

major degradates with an intact imido/amide bridge have the potential to reduce survival, 

growth and reproduction of non-target aquatic and terrestrial animals. 

The specific exposure routes quantitatively evaluated include water concentrations resulting from 

and runoff and spray drift and consumption of plants and invertebrates directly on the treated 

field by non-target terrestrial wildlife. The following hypotheses reflect these exposure 

pathways. 

 Flumiclorac-pentyl residue of concern concentrations in water may affect aquatic 

vertebrates, invertebrates, and plants. 

 Flumiclorac-pentyl residues on plants and other dietary surfaces deposited with spray 

drift may affect terrestrial organisms, and runoff of the residues of concern may affect 

terrestrial plants during 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/amide 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 imido/amide bridge are too structurally similar to the parent compound 

to expect differential toxicity with an adequate measure of certainty. Therefore, 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 SAT IMFP-HA) are assumed to have toxicity 

similar to the parent compound and are included as residues of concern for the assessed taxa. 

It is uncertain whether the degradates of concern are herbicidal. Flumiclorac-pentyl tends to 

rapidly degrade to acid derivatives including the structurally similar degradates of concern. In 

many cases, this indicates that the acid derivatives are herbicidal. However, cell membrane 

disrupting herbicides such as flumiclorac-pentyl tend to require foliar contact and a lipophilic 

chemical structure in order to sorb through the waxy leaf cuticle (K-State Research and 

Extension, 2013; OSU Extension, undated). Degradates of concern other than 031-HA are likely 

to have reduced herbicidal activity because they 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 mixtures of multiple active 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 individual risk assessment for regulatory decision regarding the active 
15 of 87 

ingredient on a particular use site. If effects data are available for a formulated product 

containing more than one active ingredient, the data 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 resulting risk conclusions are based on maximum application rates for 

flumiclorac-pentyl. Measures of exposure are 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 mitigation measures specifically indicated on the 

label (e.g. spray drift buffers). 

PRZM and EXAMS are screening simulation models coupled with the input shell PE5 (Nov. 15, 

2006) to generate daily exposures and 1-in-10 year EECs of flumiclorac-pentyl residues of 

concern that may occur in surface water bodies adjacent to application sites receiving 

flumiclorac-pentyl through runoff and spray drift. 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 simulates the fate of the pesticide and resulting 

concentrations in a receiving water body. The standard scenario used for ecological pesticide 

assessments assumes application to a 10-hectare agricultural field that drains into an adjacent 1-

hectare water body that is 2 meters deep (20,000 m3

 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 for 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 modified by Fletcher (Hoerger and Kenaga 1972; 

Fletcher et al. 1994). Exposure estimates for terrestrial animals 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 based 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 Kenega nomograph are based on measured field residues from 249 

published research papers, including information 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 terrestrial habitats by spray drift. 

2.11. Measures of Effect 

Ecological effects data are used as measures of direct 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) provides 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 maintained by the U.S. EPA, Office of Research and 

Development, and the National Health and Environmental Effects Research Laboratory's MidContinent Ecology Division. Based on the current search 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 mortality) 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 coloration). Quantitative assessments of risks, though, are limited to 

those endpoints that can be directly 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 similar to terrestrial-phase amphibians and reptiles. The 

same assumption is made for fish and aquatic-phase amphibians. 

The acute measures of effect used for animals in this assessment are the LD50, LC50 and EC50. 

LD stands for "Lethal Dose", and LD50 is the amount of a material, given all at once, that is 

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

and LC50 is the concentration of a chemical that is estimated to kill 50% of the test organisms. 

EC stands for “Effective Concentration” and the EC50 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-listed animals are the NOAEL/NOAEC and NOAEC. 

NOAEL stands for “No Observed-Adverse-Effect-Level” and refers to the highest tested dose of 

a substance that has been reported to have no harmful (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 from the control. The NOAEC is 

the No-Observed-Effects-Concentration. For non-listed plants, only acute exposures are 

assessed (i.e., EC25 for terrestrial plants and EC50 for aquatic plants); for listed plants either the 

NOAEC or EC05 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 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 ionic 

and not persistent. Flumiclorac-pentyl readily hydrolyzes, 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 DT50 values of 7.3-11 days and does not photolyze. In the 

field, flumiclorac-pentyl dissipates with DT50 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 KOC values of 34-100 L/kgOC. Major transport routes for flumicloracpentyl residues of concern include spray drift and runoff and exclude volatilization. 

Because flumiclorac-pentyl readily 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 uncertain due to hydrolysis. 

Degradation rates in the biodegradation studies were bi-phasic, likely involving both hydrolytic 

and microbial degradation. In water, representative DT50 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 other hydrolytic degradates. In aerobic soil, 

representative DT50 values were longer (7.3-11 days) than in water. 

In the field, flumiclorac-pentyl dissipated with DT50 values of less than 2-5 days. Quantities 

were uncertain because steps were not taken to stabilize flumiclorac-pentyl in storage or during 

analysis. Therefore, quantities measured often included the pentyl ester and its acid combined. 

Either way, dissipation DT50 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., Kd values) in acidic conditions were not measured. The 

compound is non-volatile, soluble in water up to 0.189 mg/L, and oleophilic (log KOW of 4.99). 

Flumiclorac-pentyl has no dissociation 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 concern are not expected to bioaccumulate because the parent 

compound hydrolyzes within hours to ionic degradates with KOW 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 KOW above that of the parent compound; however, similar to the 

parent compound, it is rapidly degraded within hours (MRID 49063001). Table 3 summarizes 

the chemical properties and environmental fate parameters 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 flumiclorac-pentyl and its degradates are listed in Table 5. 

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

Parameter Value Source

Selected Physical/Chemical Parameters

Molecular mass (molecular formula) 423.87 g/mol (C21H23ClFNO5) (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-m3/mol (Calculated)

Log octanol-to-water partition coefficient

(log KOW) (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

TREP 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 the 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 observed in the study (representative DT50 values of 1.1-1.7 

hours) cannot be distinguished from hydrolysis, especially since the stability of the test 

compound during storage and analysis was not established. 

In the anaerobic aquatic metabolism study (MRIDs 42825829 and -30; in which a hydrosoil was 

studied with ultra-purified water rather than its associated water), pH values during the study 

were not reported and compound stability during analysis 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. Therefore, the degradation observed in the anaerobic 

aquatic metabolism study (representative DT50 value of 3.7 hours) cannot be distinguished from 

hydrolysis. However, the bi-phasic degradation rates and the formation 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 DT50 values of 7.3-11 

days; MRIDs 42169844 and 43304601) were also bi-phasic and longer than those in the aquatic 

studies. Flumiclorac acid was formed in similar amounts (53-60% of the applied) as in the 

aquatic studies (41-64% of the applied), indicating microbial degradation 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 degrades to compounds that are mobile in soil, 

these compounds appear to be short-lived in the soil such that they degrade further before 

leaching a substantial distance. However, the fate of flumiclorac-pentyl residues at the surface is 

less clear. In radiolabeled lysimeter studies, nearly 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 far 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 for 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 

KOW 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 (KOC) 

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

49175801 

Log octanol-to-water partition coefficient 

(log KOW) (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 study that were not provided in the initial report 

(MRID 49175801) and that supported the calculation of soil-water partition coefficients (i.e., Kd

values). Kd values following 2 hours of equilibration were 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. These values, therefore, may be conservative but 

reasonable for exposure assessment. 

Organic carbon-normalized coefficients (KOC values) for flumiclorac acid ranged from 34 to 100 

L/kgOC, indicating that the compound is mobile in soil. KOC values are appropriate to use 

because their coefficient of variation (45%) is less than that for the Kd 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 IMCA-HA. At pH 5, the parent compound is 

cleaved into AFE and THPA. At pH 7, both degradation pathways occur, with AFE further 

hydrolyzing to form AFCA. Interestingly, flumiclorac acid (IMCA) only appears to form due to 

microbial degradation. 

Under aerobic conditions, flumiclorac acid, IMCA-HA, and 031-HA are major degradates that 

cleave to form the major cleavage products AFE, 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, IMFP-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 products THPA, AFCA, and 

AMFP. Degradates structurally similar to flumiclorac-pentyl do not persist, with the exception 

of SAT IMFP-HA under anaerobic conditions. Figure 2 shows the probable degradation 

pathway of flumiclorac-pentyl residues 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 87 

Table 5. Flumiclorac-pentyl and Its Environmental Degradates A

Code Name/ Synonym Chemical Name Chemical Structure Study Type Ref. (MRID) Maxim

%AR 

PARENT

Flumicloracpentyl S-23031 V-23031 

Pentyl 2-chloro-4-fluoro-5-(3,4,5,6-tetrahydrophthalimido)phenoxyacetate CAS No.: 87546-18-7 Formula: C21H23ClFNO5

MW: 423.87 g/mol SMILES:FC1=C(C=C(C(=C1)Cl)OCC(=O)OCCCCC)N3C(=O)C2=C(CCCC2)C3=O 

F

Cl

O

O

O

N

OO

TRANSFORMATION PRODUCTS 

031-HA Pentyl 2-chloro-4-fluoro-5-(2-

carboxycyclohexenylcarboxanido)phenoxyacetate Formula: C21H25ClFNO6

MW: 441.89 g/mol SMILES:C1(=C(CCCC1)C(=O)O)C(NC2=CC(=C(C=C2F)Cl)OCC(=O)OCCCCC)=O 

F

Cl

O

O

O

N

O

O HO

Hydrolysis –pH 5 Hydrolysis –pH 7 Hydrolysis –pH 9 

42169842 

8.0% 

86% 

97% (5

Aq. photo.– dark Aq. photo.– light 42825825 6.0% 

6.8% 

Aerobic soil 43304601 1.0% (56Aerobic aquatic 49063001 26% (0

Flumiclorac 

acid 

IMCA 

2-chloro-4-fluoro-5-(3,4,5,6-tetrahydrophthalimido)phenoxyacetic acid CAS No.: 87547-04-4 Formula: C16H13ClFNO5

MW: 353.74 g/mol SMILES:FC1=C(C=C(C(=C1)Cl)OCC(=O)O)N3C(=O)C2=C(CCCC2)C3=O 

F

Cl

O

O

OH

N

OO

Hydrolysis –pH 5 Hydrolysis –pH 7 Hydrolysis –pH 9 

42169842 

nd 

2.7% (

nd 

Soil photo.– dark Soil photo.– light 42825826 70% 

39% 

Soil photo.– dark Soil photo.– light 42825827 -- 43% Aerobic soil 42169844 53% 

43304601 60% (

Anaerobic aquatic 42825829 64% (

42825830 63% (

Aerobic aquatic 49063001 41% (0Field studies 

42825836 100% 42825837 70% (46563601 71% (
24 of 87 

Code Name/ Synonym Chemical Name Chemical Structure Study Type Ref. (MRID) Maxim

%AR 

IMCA-HA N-(5-carboxymethoxy-4-chloro-2-

fluorophenyl)-3,4,5,6-tetrahydrophthalamic acid Formula: C16H15ClFNO6

MW: 371.75 g/mol SMILES:C1(=C(CCCC1)C(=O)O)C(NC2=CC(=C(C=C2F)Cl)OCC(=O)O)=O 

F

Cl

O

O

OH

N

O

O HO

Hydrolysis –pH 5 Hydrolysis –pH 7 Hydrolysis –pH 9 

42169842 

nd 

24% (

100% (

Aerobic soil 43304601 10% Anaerobic aquatic 42825829 24% 

42825830 29% 

Aerobic aquatic 49063001 58% 

IMFP N-(4-chloro-2-fluoro-5-hydroxyphenol)-

3,4,5,6-tetrahydrophthalimide Formula: C14H11ClFNO3

MW: 295.70 g/mol SMILES:C13=C(CCCC1)C(N(C2=CC(=C(C=C2F)Cl)O)C3=O)=O 

F

Cl

HO

N

OO

Anaerobic aquatic

42825829 27% 42825830 25% 

IMFP-HA N-(4-chloro-2-fluoro-5-hydroxyphenyl)-

3,4,5,6-tetrahydrophthalamic acid Formula: C14H13ClFNO4

MW: 313.72 g/mol SMILES:C1(=C(CCCC1)C(=O)O)C(NC2=CC(=C(C=C2F)Cl)O)=O 

F

Cl

HO

N

O

O HO

Anaerobic aquatic

42825829 25% 42825830 32% 

SAT IMFPHA N-(4-chloro-2-fluoro-5-hydroxyphenyl) hexahydrophthalamic acid 

Formula: C14H15ClFNO4

MW: 315.73 g/mol SMILES:C1(CCCCC1C(=O)O)C(NC2=CC(=C(C=C2F)Cl)O)=O 

F

Cl

HO

N

O

O HO

Anaerobic aquatic

42825829 14% (42825830 15% (
25 of 87 

Code Name/ Synonym Chemical Name Chemical Structure Study Type Ref. (MRID) Maxim

%AR 

AFE Pentyl 5-amino-2-chloro-4-

fluorophenoxyacetate Formula: C13H17ClFNO3

MW: 289.74 g/mol SMILES:C1=C(C(=CC(=C1OCC(=O)OCCCCC)Cl)F)N 

F

Cl

O

O

O

NH2

Hydrolysis –pH 5 Hydrolysis –pH 7 Hydrolysis –pH 9 

42169842 

94% (28

15% 

nd 

Aq. photo.– dark Aq. photo.– light 42825824 99% (1

19% (3 

Anaerobic aquatic 42825830 1.1% (Aerobic aquatic 49063001 38% (0

AFCA 5-amino-2-chloro-4-fluorophenoxyacetic 

acid Formula: C8H7ClFNO3MW: 219.60 g/mol SMILES:C1=C(C(=CC(=C1OCC(=O)O)Cl)F)N 

F

Cl

O

O

OH

NH2

Hydrolysis –pH 5 Hydrolysis –pH 7 Hydrolysis –pH 9 

42169842 

2.0% (

68% (

1.7% (

Soil photo.– dark Soil photo.– light 42825826 15% (

11% (

Aerobic soil 42169844 20% Anaerobic aquatic 42825830 9.2% Aerobic aquatic 49063001 45% 

CFA CFPA 

(2-chloro-4-fluorophenoxy)acetic acid CAS No.: 399-41-7 Formula: C8H6ClFO3

MW: 204.59 g/molSMILES: c1cc(c(cc1F)Cl)OCC(=O)O 

F

Cl

O

O

OH

Aerobic aquatic 49063001 24% 

AMFP 5-amino-2-chloro-4-fluorophenol 

Formula: C6H5ClFNO MW: 161.56 g/mol SMILES: C1=C(C(=CC(=C1O)Cl)F)N 

F

Cl

HO

NH2 Anaerobic aquatic 42825830 17% 
26 of 87 

Code Name/ Synonym Chemical Name Chemical Structure Study Type Ref. (MRID) Maxim

%AR 

THPA 3,4,5,6-tetrahydrophthalic acid 

Formula: C8H10O4

MW: 170.17 g/mol SMILES:C1(=C(CCCC1)C(=O)O)C(=O)O 

OO

HOHO

Hydrolysis –pH 5 Hydrolysis –pH 7 Hydrolysis –pH 9 

42169842 

96% (71% (

nd 

Aq. photo.– dark Aq. photo.– light 42825825 92% (

57% (

Soil photo.– dark Soil photo.– light 42825827 -- 22% (Aerobic soil 43304601 27% (Anaerobic aquatic 42825829 58% (Aerobic aquatic 49063001 25% 

THPA-2-Na Disodium 3,4,5,6-tetrahydrophthalic 

acid Formula: C8H8O4 . 2 Na 

MW: 214.13 g/molSMILES: C1CCC(=C(C1)C(=O)O[Na])C(=O)O[Na] 

OO

-O

Na -O

+

Na

+ Aerobic aquatic 49063001 81% 

1-OH-HPA 1-hydroxy-trans-1,2-

cyclohexanedicarboxylic acid Formula: C8H12O5

MW: 188.18 g/mol SMILES:C1(C(CCCC1)C(=O)O)(C(=O)O)O 

OO

HOHO

OH Aerobic soil 43304601 34% (

Aerobic aquatic 49063001 16% (

Unidentified 

residues 

(unknown) 

(unknown) 

Aq. photo.– dark Aq. photo.– light 42825824 5.0% (1

57% (1

Aq. photo.– light 42825825 22% (1Soil photo.– dark Soil photo.– light 42825826 11% (2

32% (

Soil photo.– dark Soil photo.– light 42825827 -- 13% (1Aerobic soil 43304601 28% (

Unknown A E Aerobic aquatic 49063001 12% (Unknown C E 37% (0
27 of 87 

Code Name/ Synonym Chemical Name Chemical Structure Study Type Ref. (MRID) Maxim

%AR 

Unextracted 

residues 

(not applicable) 

(not applicable) 

Soil photo.– dark Soil photo.– light 42825826 30% (

35% (

Soil photo.– dark Soil photo.– light 42825827 15% (

35% (

Aerobic soil 42169844 73% (

43304601 31% (

Anaerobic aquatic 42825829 3.3% (

42825830 23% (

Aerobic aquatic 49063001 54% (

Carbon 

dioxide

Carbon dioxide Formula: CO2

MW: 44.01 g/mol SMILES: O=C=O 

O O

Aq. photo.– light 42825824 23% (

Aq. photo.– dark Aq. photo.– light 42825825 0.04% 

0.59% 

Soil photo.– dark Soil photo.– light 42825826 0.02% 

7.3% (

Soil photo.– dark Soil photo.– light 42825827 0.02% 

14% (

Aerobic soil 42169844 2.0% (

43304601 36% (1

Anaerobic aquatic 42825829 0.6% (

42825830 0.7% (

Aerobic aquatic 49063001 50% (1

A nd means “not detected”. AR means “applied radioactivity”. MW means “molecular weight”. Code names of residues of concern are underlined. B

laboratory study values >10%AR. 

B AFE in MRID 42825824 was AFE plus 031-HA, the latter of which was not a major degradate at pH 5 in MRID 42169842 or 42825825. C These unidentified residues were a collection of polar compounds. In MRIDs 42825824, 42825826, and 42825827, none of the polar compounds ex

(no product exceeded 5% of the applied in MRID 42825827). In MRID 42825825, none of the polar compounds exceeded 20% of the applied. 

D These unidentified residues were organo-soluble. E These 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 toxicity 

as 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 toxicity values that were often non-definitive 

(Appendix E). Therefore, they were not useful predictors 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 otherwise, the six major degradates with an intact imido/carboxamido 

bridge are assumed to be of similar toxicity to aquatic and terrestrial organisms as flumicloracpentyl. The same residues are of concern for ecological risk assessment as for drinking water 

exposure assessment in support of human health dietary risk assessment (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-lives 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 different from that for the parent compound. However, at pH 7, the 

ROC half-life is 20 days, which is much longer than 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 (KOC)

34, 49, 72, 100 (values for 

flumiclorac acid)

MRID 42169845/ 

49175801 A IORE means “indeterminate order rate equation.” 

EPI Suite (v4.10) indicates that flumiclorac acid is more mobile than or as mobile as most of the 

degradates of flumiclorac-pentyl (the cleavage products AFCA and 1-OH-HPA are the 

exceptions). Because flumiclorac acid is a prominent degradate of flumiclorac-pentyl and it is 

one of the more mobile residues of concern, KOC 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 approach 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 properties of flumiclorac-pentyl (from Table 3). The TR approach is 

appropriate because there are multiple degradates 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-first-order representative half-lives 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 resulting hydrolysis-adjusted half-lives were then 

calculated according to current guidance (USEPA, 2009) to produce the input values in Table 7. 

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

Input Parameter Value Justification Source

Molecular Mass (g/mol) 423.87 Product chemistry data (Calculated) 

Henry’s Law Constant 

(atm m3

/mol) 3.0 × 10-7 Ratio of vapor pressure to water 

solubility 

(Calculated from 

MRID 42187405)

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

Organic Carbon Partition 

Coefficient (KOC) (L/kgOC) 64 Mean value for flumiclorac acid, a 

prominent degradate of concern 

MRIDs 42169845/ 

49175801 

Aerobic Soil Metabolism 

Half-life (days) 42 90th percentile confidence bound on the mean TRC value for two soils 

MRIDs 42169844, 

43304601 

Aerobic Aquatic Metabolism 

Half-life (days) 153 

90th 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 inputs 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 applicable application rates, for uses on soybeans and field corn. The 

PRZM scenarios, application efficiencies, and spray drift factors listed in Table 8, however, 

represent the single modeling scenarios for each use that resulted in highest exposure (including 

consideration of Spring burndown uses). 

Dates of initial application were selected within 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 1st or 15th of months within the crop season and selecting the date 

for which exposure estimates were highest. This 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-end exposure scenarios do not result in risk 

concerns, then there are no risk concerns from less-high-end exposure scenarios either. 

Table 8. PRZM Scenarios and Input Parameters 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 between 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 environmental exposure concentrations (EEC). 
31 of 87 

Table 9. Aquatic Exposure Estimates from 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 expected to appreciably bioaccumulate in aquatic 

or terrestrial organisms because the parent compound hydrolyzes within hours to ionic 

degradates with KOW 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 KOW above that of the 

parent compound; however, similar to the parent compound, it is rapidly degraded within hours 

(MRID 49063001). With a log KOW of 4.99, however, flumiclorac-pentyl meets the criteria for 

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

KABAM (v.1.0; Apr. 7, 2009) was used to estimate potential bioaccumulation of flumicloracpentyl residues in a freshwater aquatic food web and subsequent risks these residues pose to 

terrestrial organisms via consumption of contaminated aquatic prey (i.e., aquatic invertebrates 

and fish). The model was run in default mode (see user’s guide for full description), with a log 

KOW of 4.99, a KOC of 4,430 L/kgOC (estimated with EPISuite v4.11), and a surface water and 

pore water EEC of 3.4 μg/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 flumiclorac-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 most residues of concern have a KOW value orders of magnitude 

lower than that of flumiclorac-pentyl. A metabolism rate constant (kM) was not input for fish 

because the estimated depuration rate in KABAM was higher than 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 derive 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 expectation that flumiclorac-pentyl and its residues of concern 

will not appreciably bioaccumulate in aquatic or terrestrial organisms. 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 Regulation (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/nawqa_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.fetchTemplateData.do?template=TemplateG&navID=

&rightNav1=&topNav=&leftNav=ScienceandLaboratories&page=PDPDownloadData/Reports&

resultType=&acct=pestcddataprg). 

3.3. Terrestrial Exposure 

The Agency used the Terrestrial Residue EXposure 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 and 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 (Hoerger & Kenaga, 1972). The model 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 calculate Rick Quotients (RQs) for estimation of risk 

for these species. Birds are also used as a surrogate for reptiles and terrestrial-phase amphibians. 

The TERRPLANT model can be used to estimate risk from runoff to monocot and dicot 

terrestrial plants in areas adjacent to the treated field (sheet 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 from 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-pentyl is 0.189 mg/L (MRID 42187405). In discussions 

with The Agency on January 18, 1989 and on February 27, 1992, the registrant indicated that 

preliminary aquatic animal testing with flumiclorac-pentyl indicated they had problems 

achieving solubility within the parameters outlined in guideline testing. They were unable to 

achieve solubility greater than 0.1 mg flumiclorac-pentyl/L with the guideline recommended cosolvents at a concentration of 0.1 mL solvent/L test solution. They also indicated that no fish 

mortality was observed at 0.1 mg/L of flumiclorac-pentyl. Therefore, alternative co-solvents and 

solvent concentrations for use in aquatic animal testing were requested by the registrant. Agency 

staff at the time indicated that the registrant should provide justification for these extra measures 

and would view favorably a well designed study which resulted in a dose response. The 

registrant provided information for the use of dimethyl formamide: polyoxyethylene 

hydrogenated castor oil (1:1, DMF:HCO-40), and toxicity 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 solvent 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 conducted at solvent concentrations 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-solvent 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 delivery system. No precipitate was reported in the 96-hour acute 

mysid toxicity study. Test solution appearance was not reported for either the acute rainbow 

trout or bluegill toxicity study. So while a presence of precipitate was not mentioned in these 

reports, the absence of precipitate cannot be assumed based on the known solubility of the 

chemical and presence of precipitate in the other toxicity studies. For all studies in which 

precipitate was observed, an attempt to remove the precipitate from the analytical samples prior 

to analysis (ex. centrifugation, filtering) was not reported. Therefore, it is not known what the 

actual dissolved flumiclorac-pentyl concentration in the test systems were, as the presence of 

precipitate during analysis could overestimate the actual exposure concentration. All of these 

studies were conducted above the reported solubility of 0.189 mg/L for flumiclorac-pentyl, and 

therefore, the NOAEC level for all aquatic studies are above this reported water solubility. LC50

values were obtained for the bluegill sunfish, rainbow trout and mysid invertebrate, but with the 

exception of the mysid toxicity data, actual aquatic exposure concentrations are uncertain. A 

LC, EC50 concentration could not be determined for the sheepshead minnow or Daphnia magna 

toxicity study, respectively, due to a lack of dose response. Since this uncertainty exists for these 

aquatic studies in which precipitate was observed these studies are classified as supplemental. 

Also, the 96-hour oyster shell growth deposition study was classified 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 measured), 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 there 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-pentyl 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 parent flumiclorac-pentyl (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 concentration 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 number 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 density compared to the negative 

control. 
34 of 87 

There are no chronic toxicity data for freshwater or estuarine-marine fish. Flumiclorac-pentyl is a 

light-dependent peroxidizing herbicide (LDPH), and may be very toxic to aquatic organisms. 

Therefore, the Aquatic Biology Tech Team (ABTT) recommends that phototoxicity studies be 

conducted on herbicides with this mode of action to determine if animals exposed to LDPHs and 

intense light (similar to sunlight) show increased toxicity relative to controls 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 enhanced 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 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 for estimation of chronic risk to fish. Based 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 intensity. Effects to estuarine-marine fish and 

aquatic-phase amphibians are also possible based on surrogacy to freshwater fish. 

Table 10. Summary of sensitive endpoints for 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 LC50 

> 0.189 1

1.12

(mortality) 

42169806 

Acceptable Moderately Toxic3

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 LC50

> 0.189 1

> 24 2

(mortality) 

42825809 

Supplemental NA4 

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 NA4 

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 LC50 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) 

F0 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 NA4

Marine Diatom 

Skeletonema costatum 96 hours NOAEC 

EC50 

0.41 (IMCA) 

>0.41 (IMCA) 

48864501 

Acceptable NA4

Freshwater Blue-green Algae 

Anabaena flos-aquae 96 hours NOAEC 

EC50 

0.82 (IMCA) 

>0.82 (IMCA) 

48804301 

Acceptable NA4

Green Algae 

Selenastrum capricornutum 96 hours NOAEC 

EC50 

0.035 (IMCA) 

> 0.035 (IMCA)

43240800 

Acceptable NA4 

Duckweed 

Lemna gibba 14 day NOAEC 

EC50 

0.035 (IMCA) 

> 0.035 (IMCA) 

43251201 

Acceptable NA4

TGAI=technical grade active ingredient; LC50 = median lethal concentration; NOAEL=no observable 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 ai/L). Actual test concentration not known due to the presence of 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 measured 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 (aquatic 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 practically nontoxic to birds, mammals, and terrestrial 

invertebrates. 

Acute, subchronic, and chronic toxicity 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 the oral, dermal and inhalation routes of exposure. Flumiclorac-pentyl did 

not cause developmental toxicity in rat or rabbit fetuses. Reproductive parameters were not 

adversely affected in rats in a reproduction study. No evidence of neurotoxicity or 

carcinogenicity was observed. 

No mortality was observed in acute oral-dose or subacute dietary avian studies. Reduced egg 

laying, regressed ovaries and small testes were observed in the chronic study with the mallard 

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

Based on the degradation of parent flumiclorac-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 maximum application rate of flumiclorac-pentyl 

and the expected maximum concentration of the degradate IMCA (53% of the flumiclorac-
36 of 87 

pentyl) to be present. The study was conducted with both a negative and solvent control 

(acetone), but percent emergence and shoot height comparisons between the negative control and 

treatment group is more appropriate than a comparison using pooled controls. Based on a 

reduction in shoot lengths, the onion and oat were statistically significant compared to the 

negative control and the shoot height reductions ranged from -9.8 to 15% compared to the 

negative control. Decreases in seedling emergence 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 emergence study which is generally a 

sensitive endpoint for evaluating toxicity. The vegetative vigor study was conducted using 

parent flumiclorac-pentyl. The most sensitive 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 

LD50

> 5,000 mg/kg (mortality) 42169812/ 

Acceptable 

Practically 

Nontoxic 

Rat 

(Rattus 

norvegicus) 

V-23031 0.83 EC 

LD50

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 NA1 

Birds

Bobwhite Quail

(Colinus 

virginianus) 

TGAI 

Zebra Finch 

(Taeniopygia 

guttata) 

TGAI 

LD50

> 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 

LC50

>5322 mg ai/kg-diet (no mortality) 

42169803, 

42169804/ 

Acceptable 

NA1 

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 NA1 
37 of 87 

Terrestrial Invertebrates 

Honey Bee 

(Apis mellifera)

TGAI 

Contact 

LD50

> 106 μg/bee 

(no mortality) 

42169841/ 

Acceptable 

Practically 

Nontoxic 

Terrestrial Plants 

Seedling 

Emergence 

Seedling 

Emergence 

EC25 > 0.046 lb IMCA/Acre

43258001/ 

Acceptable NA1 

NOAEC < 0.046 lb IMCA/Acre2

Vegetative vigor 

Vegetative vigor 

EC25

0.027 lb ai/Acre 

(Based on dry weight for lettuce) 43347401/ 

Acceptable NA1 

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 not applicable for study. 2 Due to study conducted as a limit test, and 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 hypothesis, the potential for adverse effects on the environment is 

estimated. The use, environmental fate, and ecological effects of flumiclorac-pentyl residues of 

concern are characterized and integrated to assess the risks. This is accomplished using a risk 

quotient (RQ; ratio of exposure concentration to effects 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 when acute or chronic risk LOCs are exceeded, the need for 

regulatory action may be considered. These criteria are used to indicate when the use of a 

pesticide, as directed on the label, has the potential to cause adverse effects to non-target 

organisms. For acute and chronic risks to animals, 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 additional data and lines of evidence. 

Although risk is often defined as the likelihood and magnitude of adverse ecological effects, the 

risk quotient-based approach does not provide a quantitative estimate of likelihood and/or 

magnitude of an adverse effect. However, as outlined in the Overview Document (U.S. EPA 

2004), the likelihood of effects to individual organisms from particular uses of flumicloracpentyl is estimated using the 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 immediately 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 flumiclorac-pentyl are not expected 
38 of 87 

to pose a risk of mortality or reproductive effects 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 rates and no further RQs were calculated. 

Single Application: 

Table 12. Estimated environmental concentrations (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) Max 

DietaryBased 

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 concentrations (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 Max 

DietaryBased 

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 concentrations (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 Max 

DietaryBased 

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 chronic (0.04-0.78) RQs based on dietary-based 

exposures of birds and dose-based or dietary-based exposures of mammals to flumiclorac-pentyl 

ROCs through consumption of contaminated aquatic 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 bioaccumulation 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 water using flumiclorac pentyl’s solubility 

(0.189 ppm), the most sensitive acute and chronic avian toxicity endpoints (Avian LD50 >2131 

mg/kg-bw and 220 ppm, respectively) and the most sensitive acute mammalian toxicity 

endpoints (Rat LD50 >5000 mg/kg-bw & Rat NOAEC of 200 ppm). Drinking water exposure 

alone was determined not to be a potential acute or chronic pathway of concern for avian or 

mammalian species. Results for mammalian and avian species are presented 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 was 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 plants with respect to vegetative vigor for the 

proposed maximum application rate (0.081 lbs ai/A for ground applications and 0.054 lbs ai/A 

for aerial applications) for soybean applications. For listed species, there are RQs of 2.61 and 

8.71 for ground spray drift and drift from 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 assessed for seedling emergence because no NOAEC or EC05 is 

available. However, using the limit test level (0.046 lbs ai/A) as a conservative endpoint, no risk 

of concern was calculated. The endpoints selected 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 plants. Rates for ground 
42 of 87 

applications would need to be <0.03 lbs ai/A and <0.006 lbs ai/A for aerial applications to reduce 

risk below the LOC for listed dicots. 

Applications may impact sensitive species in terrestrial habitats. These risks may be reduced 

through label changes, including decreases in maximum single applications, decreases in the 

number of applications allowed per year, removal of aerial applications, 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 treatment 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 

LD50 >106 μg/bee. In this study, no significant mortality was observed at the highest test dose. 

Using the exposure methodology for foliar sprays as presented in the pollinator white paper3, 

where an application rate of 1 lb a.i./A generates a contact dose of 2.7 μg 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 expected for honey bees exposed to flumicloracpentyl from direct spray. Given that no oral toxicity data are available for adult and larval bees 

exposed to this chemical, there is uncertainty in the risks 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 estuarine/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 Protection Agency, Office of Pesticide Programs, Washington DC. Pest Management 

Regulatory Agency, Health Canada, Ottawa. California Department of Pesticide Regulation, Sacramento, CA. 
43 of 87 

There are no chronic toxicity tests for fish (freshwater and estuarine/marine) for Flumicloracpentyl, which leads to uncertainty in the evaluation of chronic aquatic organism risk. This 

uncertainty is compounded by the fact that this chemical is an LDPH, which would suggest that 

chronic toxicity would be increased for fish in areas 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 that incident, there was damage to a soybean crop after application 

of a product containing flumiclorac-pentyl. However the report notes that the damage was 

believed to have been caused by residual contamination from a prior use of the tank involving 

2,4-D, and therefore was not due to flumiclorac-pentyl. Thus, the incident data give no evidence 

of this active ingredient causing any problems to non-target species. However, given that the 

number of incidents thought to occur in the environment relative to the number of incidents 

reported to the Agency is so low, lack of reported 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 numerous studies to assess potential adverse 

outcomes from exposure to chemicals. Collectively, these studies include acute, subchronic and 

chronic toxicity, including assessments of carcinogenicity, neurotoxicity, developmental, 

reproductive, and general or systemic toxicity. These studies include endpoints which may be 

susceptible to endocrine influence, including effects on endocrine target organ histopathology, 

organ weights, estrus cyclicity, sexual maturation, fertility, pregnancy rates, reproductive loss, 

and sex ratios in offspring. For ecological hazard assessments, EPA evaluates acute tests and 

chronic studies that assess growth, developmental and reproductive effects in different 

taxonomic groups. As part of its most recent registration decision for flumiclorac-pentyl, EPA 

reviewed these data and selected 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 the Endocrine Disruptor 

Screening Program (EDSP). 

EPA has developed the EDSP to determine whether 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 other such endocrine effects as the Administrator 

may designate.” The EDSP employs a two-tiered approach to making the 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 estrogen, androgen, or thyroid (E, A, or T) hormonal 

systems. Chemicals that go through Tier 1 screening and are found to have the potential to 

interact with E, A, or T hormonal systems will proceed to the next stage of the EDSP where EPA 

will determine which, if any, of the Tier 2 tests are necessary based on the available data. Tier 2 
44 of 87 

testing is designed to identify any adverse endocrine-related effects 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 pesticide active ingredients and 9 inert ingredients. A second list 

of chemicals identified for EDSP screening was published on June 14, 20134

 and includes some 

pesticides scheduled for registration review and chemicals found in water. Neither of these lists 

should be construed as a list of known or likely endocrine disruptors. 

For further information on the status of the EDSP, the policies and procedures, the lists of 

chemicals, future lists, the test guidelines and the Tier 1 screening battery, please visit our 

website.5

4.5. Risk Description 

Risk characterization is the integration of exposure and ecological effects characterization to 

determine the potential ecological risk from the use of flumiclorac-pentyl as a herbicide and the 

likelihood of direct and indirect effects to non-target organisms in aquatic and terrestrial habitats. 

The exposure and toxicity effects data are integrated in order to evaluate the risks of adverse 

ecological effects on non-target species. For the assessment of flumiclorac-pentyl risks, the risk 

quotient (RQ) method is used to compare exposure 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 the 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 concern 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. Flumiclorac-pentyl shows low toxicity to germinating seeds in seedling 

emergence tests (MRID 43104701). The primary degradate of flumiclorac-pentyl, IMCA, is also 

not toxic to germinating seeds (MRID 43240801). Vegetative vigor toxicity tests on lettuce, 

radish, tomato, cucumber, cabbage, ryegrass, corn, and onion showed phytotoxic effects but did 

not on soybean and oats. Only the parent compound, 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 terrestrial 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 and 0.054 lbs ai/A for 

aerial applications) for soybean & corn applications, respectively. For listed species, there 

are RQs of 2.61 and 8.71 for ground spray drift and drift from aerial application of 

flumiclorac-pentyl, respectively. 

The model AgDRIFT (v2.1.1) was used to calculate the spray drift buffers needed to reduce 

terrestrial plant exposure to below the toxicity thresholds for listed plant species (tomato 

Lycopersicon esculentum, NOAEC = 0.00031 a.i. lb/acre). A Tier 1 analysis was performed. 

For ground application buffers, the following input parameters were used. A high-boom sprayer, 

producing very fine to fine spray droplets and the 90th 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 (appearing on EPA Reg. 59639-100), the listed plant buffer 

is 509 feet. 

For aerial application, ASAE medium to coarse spray and an application 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 for aerial applications. 

For listed plant species, the calculated buffer is 876 feet. Applications may impact sensitive 

species of plants in terrestrial habitats. In general, 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 applications 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 and chronic risk to aquatic invertebrates as well as 

risk to aquatic plants). Since there were no risks 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 addition, no data using enhanced lighting were available. 

Since flumiclorac-pentyl may be more toxic 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-pentyl and its degradates. The QSAR estimates 

didn’t track well with the measured values (there were only a few definitive tox values for 

comparison). Another phthalimide herbicide similar to flumiclorac-pentyl that is registered in 

the United States is flumioxazin (chemical structure is in Appendix B, Table B.1). However, it 

has a nitrile group that may give it toxicity characteristics different than flumicloracpentyl. Other LDPH chemicals with structural similarities, such as fluthiacet-methyl, are also 

structurally different enough such that 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 and no usable surrogate data, risk could not be 

calculated for those organisms. 

The toxicity and exposure profiles of flumiclorac-pentyl residues 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-lives range from 25 to 59 days, indicating that they 

may be present in water bodies for a sufficient duration to result in chronic exposure. 

Concentrations of flumiclorac-pentyl in acute toxicity tests were greater than the compound’s 

solubility limit in water (0.189 mg/L), complicating acute to chronic endpoint value 

comparisons. However, a comparison was conducted comparing the acute toxicity value for 

Rainbow Trout (1,100 μg/L) to the maximum chronic 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 order to exceed the risk level of concern. For non-LDPH chemicals, 

this may be a large enough acute-to-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 potentially 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 this uncertainty and to quantitatively evaluate 

the chronic risk to fish. 

4.5.3 Endangered Species Assessment 

Based on this screening-level assessment, there are potential risks of direct effects to listed 

terrestrial plants (and possibly freshwater and estuarine/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 Registration Review process, it is premature to make 

effects determinations for listed species until further scientific analysis and refinements are 

conducted, based on recommendations received from the National Academy of Sciences’ (NAS) 

National Research Council (NRC) April 2013 report, available at

http://www.nap.edu/catalog.php?record_id=18344. The NAS report outlines recommendations 

on specific scientific and technical issues related 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 Service (USFWS), the National Marine Fisheries 

Service (NMFS) (collectively, the Services), and the U.S. Department of Agriculture (USDA), 

released a summary of their implementation plan for assessing risks of pesticides to listed species 

ahead of the stakeholder workshop held on November 15, 2013. This plan was developed in 
47 of 87 

response to the NAS’ recommendations, including a common approach to risk assessment as a 

way of addressing scientific differences between 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 implementation 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 determination portion of this risk assessment. 

To make effects determinations for individual listed species, useful refinements may include, but 

are not limited to, analyses of: 1) more detailed, species-specific ecological and biological data; 

2) more detailed and accurate information 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 expected to further refine the assessment and are 

designed to support effects determinations for individual federally listed species and their 

designated critical habitats (where applicable). Scientific information obtained from the 

Services, and other reliable sources 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 repository 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 document repository that contains supporting documents 

(e.g., USFWS recovery plans) and electronic information (e.g., GIS data files). For terrestrial 

taxa, biological information relevant to the assessment (e.g., diet and body weight) will be used 

to parameterize exposure estimates using a method consistent 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 Adversely Affect” (LAA) or “Not Likely to Adversely 

Affect” (NLAA) determinations for federally listed species. The analyses may include more 

information on where, when, and how flumiclorac-methyl is used on all use sites. Actual usage 

data (when available) and national land-cover datasets that indicate potential use sites [e.g., 

National Land Cover Dataset (NLCD), Cropland Data 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 more in-depth exploration of agronomic practices 

for flumiclorac-methyl may be included as part of the refinement. 

The refinements based on individual species data; additional, detailed usage information, when 

available; and recommendations from the NRC report 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 designated 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 order to support risk assessment. 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 requested in the Problem Formulation stage of 

Registration Review. Therefore, the risk assessment 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 42169842 Acceptable Yes -- 

835.2240 Aqueous 

photolysis 

42825824 Acceptable Yes -- 

42825825 Acceptable 

835.2410 Soil photolysis 42825826 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 uncertainties 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 

42825832/42986502 Acceptable 

42825833/42986501 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 42825834 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 Acceptable Yes -- 

42169810/42825813 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 provide 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 fish toxicity studies (Guideline 850.1400) under 

normal and UV enhanced light with the fathead and sheepshead minnow, respectively. 

Enhanced toxicity to organisms may occur due to flumiclorac-pentyl being a light dependent 

peroxidizing herbicide. Therefore 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, plants, and terrestrial birds and mammals. This study was already 

required in GDCI-128724-26284. The registrant Valent USA Corporation has joined the 

registrant light dependent peroxidizing herbicide workgroup (LDPH WG), and has 

technically satisfied the aforementioned DCI with 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 LDPH 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 for 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 conditions. Thus, the Agency is expecting a study 

to address this uncertainty. 

6. REFERENCES 

6.1. Open Literature 

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. 

CFR 40. 2007. Code of Federal Regulations, Title 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 instrument for estimating pesticide residues on 

plants. Environ. Tox. Chem. 13:1383-1391. 

Hoerger, F. and E. E. Kenaga, 1972. Pesticide Residues on Plants: Correlation of Representative 

Data as a Basis for Estimation of their Magnitude in the Environment. In F. Coulston and 

F. Korte, eds., Environmental Quality and Safety: Chemistry, Toxicology, and 

Technology, Georg Thieme Publ., Stuttgart, 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. Publication 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. Protoporphyrinogen oxidase as a 

molecular target for diphenyl ether herbicides. Biochem. J. 260: 231-235. 

OSU Extension. Undated. K.L. Smith. Weed Control 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 and 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 Parameters in Modeling the 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 Agency, 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, Registration 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 Pesticide 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 Pesticide 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-pentyl Residue Chem for the TRED. EPA-HQ-OPP-2005-0229-

0005. September 15, 2005. Office of Pesticide Programs. Washington, D.C. 

U.S. EPA. 2005g. Flumiclorac-pentyl TRED Product Chem Considerations. EPA-HQ-OPP2005-0229-0006. September 15, 2005. Office of Pesticide 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 Pesticide Programs. Washington, D.C. 

U.S. EPA. 2005i. Flumiclorac-pentyl EFED Addendum No. 1 to MRID#42169844. EPA-HQOPP-2005-0229-0008. September 15, 2005. Environmental Fate and Effects Division. 

Washington, D.C. 

U.S. EPA. 2005j. Flumiclorac-pentyl EFED Addendum No. 1 to MRID 43304601. EPA-HQOPP-2005-0229-0009. September 15, 2005. Environmental 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; Data Requirements for Conventional Chemicals: 

Final Rule. 72 FR 60934. October 26, 2007. 

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

Programs. Washington, DC. 

U.S. EPA. 2009. ECOTOXicology Database. Office 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. Memorandum 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: Procedures 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 Fisheries Service of an approach to assessing the ecological risks of 

pesticide products. From Steve Williams and William Hogarth to Susan Hazen. January 

26, 2004. 

6.2. Submitted Environmental Fate and Product Chemistry Studies 

MRID Citation Reference 

42169809 Ohshima, M.; Mikami, N. (1991) Uptake, Depuration and Bio- concentration of 14C-PH-S-23031 to 

Bluegill Sunfish (Lepomis macrochirus): Lab Project Number: ACC90001A. Unpublished study 

prepared by Sumitomo Chemical Co., Ltd. 41 p. 

42169810 Ohshima, M.; Mikami, N. (1991) Uptake, Depuration and Bioconcentration of 14C-THP-S-23031 

to Bluegill Sunfish (Lapomis macrochirus): Lab Project Number: ACC90001B. Unpublished study 

prepared by Sumitomo Chemical 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-14C-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 Desorption 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-14C-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 Chemical 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. (1993) Characterization of 14C Residues in Bluegill Sunfish Treated with 14C-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. (1993) Characterization of 14C Residues in Bluegill Sunfish Treated with 14C-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-14C-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-14C-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-14C-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-14C-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-14C-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-14C-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 Leaching Study with THP-14C-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-14C-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 Ricerca, 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-23031 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 14C-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 Leaching Study with PH-14C-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 Leaching Study with THP-14C-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 14C-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-14C 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 Dissipation 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, IMCA 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 Adsorption 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 ester 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 14C-PH-S-23031 to 

Bluegill Sunfish (Lepomis macrochirus): Lab Project Number: ACC90001A. Unpublished study 

prepared by Sumitomo Chemical 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 Dietary 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.; Hoxter, 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 Acute 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 Toxicity 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 Toxicity 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 Toxicity 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: 42825810 

Bettencourt, 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 (Crassostrea 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 Chemical 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 Chemical 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 Toxicity 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) Primary Eye Irritation Study with Resource 80 WP in Rabbits: Lab Project 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 the 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 Irritation 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 Repeated 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 Guinea 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 Analyses: Lab Project Number: 1632. Unpublished study 

prepared by Sumitomo Chemical 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 Female 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 Article Entitled "A Micro- dissection Method 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: 42169835 

Nemec, 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 Toxicity/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 Chemical 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: Revised: 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 Germination/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 (Selenastrum capricornutum): 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 87 

Appendix A. Summary of Toxicity Data Table A1. Summary of Submitted Aquatic Toxicity Data for Flumiclorac-pentyl Reported Solubility of flumiclorac-pentyl is 0.189 mg/L 

Study 

Type 

Test Species 

(Genus 

Species)/ Flowthrough/ 

Static 

% a.i. 

Toxicity Endpoint 

(Measured/ 

Nominal) 

Effect 

MRID (Year) 

Classification 

or Source 

Com

Freshwater Vertebrates

Acute 

850.1075 

72-3 

Bluegill Sunfish 

(Lepomis 

macrochirus)/ 

Flow-Through 

TGAI 

94.7 

96-hr LC50= 17.4 mg/L 

(measured)1 (16.5 mg ai/L) 

 LOAEC = 13 mg/L 

NOAEC = 7.8 mg/L 

96-hr LC50 > 0.189 mg/L2

Mortality 42169807 

(1989) 

Acceptable 

DER 4/29/92 

 Test solution appearanc

water solubility and oth

have been present. W

filtered before mea

DMF:HCO-40 (1:1) solv

concentrations of 32

concentrations cannot 

effects included abn

equilibrium and lethargy

observed at 7.8 mg/

concentrations ranged fr

mortality occurred a

Acute 

850.1075 

72-3 

Rainbow Trout 

(Salmo gairneri)/ 

Flow-Through 

TGAI 

94.7 

96-hr LC50= 1.1 mg/L 

(measured)1 (1.0 mg ai/L) 

 LOAEC = 0.87 mg/L 

NOAEC = 0.51 mg/L 

96-hr LC50 > 0.189 mg/L2

Mortality 42169806 

(1989) 

Acceptable 

DER 4/29/92 

Test solution appearanc

water solubility and oth

have been present. W

filtered before mea

DMF:HCO-40 (1:1) solv

concentrations of 5

concentrations cannot 

effects included swim

bottom orientation, loss 

No sublethal effects w

Measured concentratio

nominal and mortality 

above. N
64 of 87 

Study 

Type 

Test Species 

(Genus 

Species)/ Flowthrough/ 

Static 

% a.i. 

Toxicity Endpoint 

(Measured/ 

Nominal) 

Effect 

MRID (Year) 

Classification 

or Source 

Com

Estuarine/Marine Vertebrates 

Acute 

850.1075 

72-3 

Sheepshead 

Minnow 

(Cyprinodon 

variegatus)/ 

Flow-Through 

TGAI 

94.6 

96-hr LC50 > 24 mg ai/L 

(measured)1

 LOAEC > 24 mg ai/L 

NOAEC = 24 mg ai/L 

96-hr LC50 > 0.189 mg/L2

Mortality 42825809 

(1992) 

Supplemental 

DER 2/10/94 

Precipitate was observed 

was not centrifuged or 

concentrations. DMF:

present at maximum 

DMF:HCO-40/L. Tru

cannot be determined. 

observed in any treatmen

in the solvent control a

Solvent Control concent

tolerable concentration

averaged 95% of n

Freshwater Invertebrates

Acute 

850.1010 

72-3 

Waterflea 

(Daphnia 

magna)/ 

Flow-Through 

TGAI 

94.6 

48-hr EC50 > 38.0 mg/L 

(measured)1 (35.9 mg ai/L) 

LOAEC = 3.98 mg/L 

NOAEC = 1.88 mg/L 

48-hr EC50 > 0.189 mg/L2

Mortality 42169808 

(1991) 

Acceptable 

DER 5/26/92 

Precipitate was observed 

was not centrifuged or 

concentrations. DMF:

present at maximum 

DMF:HCO-40/L. Tru

cannot be determined. 

lethargy, and white prec

in high treatment group

ranged 75 to 102% of 

Chronic 

Life-cycle 

Waterflea  (Daphnia magna) 

IMCA 

99.3 

LOAEC = >0.67 mg/L 

NOAEC = 0.67 mg/L 

None 48848801 

Acceptable 

Estuarine/Marine Invertebrates

Acute 

850.1025 

72-3 

Eastern Oyster 

(Crassostrea 

virginica)/ 

Flow Through 

TGAI 

94.6 

96-hr EC50 > 1.8 mg ai/L 

(measured)1

96-hr EC50 > 0.189 mg/L2

Shell 

Growth 

42825811 

(1992) 

Invalid 

DER 2/10/94 

The test solution 

concentrations was clo

(DMF) was 0.5 mL DM

decreased substantially 

31% of nominal. DO 

study and was 28 to 1

deposition in controls w
65 of 87 

Study 

Type 

Test Species 

(Genus 

Species)/ Flowthrough/ 

Static 

% a.i. 

Toxicity Endpoint 

(Measured/ 

Nominal) 

Effect 

MRID (Year) 

Classification 

or Source 

Com

Acute 

850.1035 

72-3 

Mysid Shrimp 

(Mysidopsis 

bahia)/ 

Flow Through 

<24-hr old 

TGAI 

94.6 

96-hr LC50 = 0.56 mg ai/L 

(measured) 

NOAEC = 0.11 mg ai/L 

Mortality 42825810 

(1993) 

Acceptable 

DER 1/28/94 

No undissolved test m

diluter system or an

Concentration was 0.5m

were loss of equilibriu

darkened pigmen

concentrations ranged 

Low measured test conc

to degradation of flu

rep

Chronic 

Life-Cycle 

Mysid Shrimp 

(Mysidopsis 

bahia) 

IMCA 99.3 

LOAEC = 0.44 mg/L 

NOAEC = 0.22 mg/L 

prepairing 

and 

overall 

survival 

48848701 

Acceptable 

Aquatic Vascular and Nonvascular Plants 

Acute Freshwater 

Diatom 

(Navicula 

pelliculosa) 

IMCA NOAEC=0.88 (IMCA) 

EC50 >0.88 (IMCA) 

Growth 48864401 

Acceptable 

Acute Marine Diatom 

(Skeletonema 

costatum) 

IMCA NOAEC=0.41 (IMCA) 

EC50 >0.41 (IMCA) 

Growth 48864501 

Acceptable 

Acute Freshwater Bluegreen Algae 

(Anabaena flosaquae) 

IMCA NOAEC=0.82 (IMCA) 

EC50 >0.82 (IMCA) 

Growth 48804301 

Acceptable 

Acute 

850.4400 

122-2 

Duckweed 

(Lemna gibba)/ 

Static-renewal 

IMCA3

98.0 

EC50 > 0.035 mg IMCA/L 

(measured) 

Increase of 3.3% and 12.8% 

for frond number and dry 

weight, respectively, for 

treatment compared to 

negative control 

Growth 43251201 

(1994) 

Acceptable 

DER 10/24/94 

Study conducted for 14 

on days 3, 6, 9 and 12

nominal conc. o
66 of 87 

Study 

Type 

Test Species 

(Genus 

Species)/ Flowthrough/ 

Static 

% a.i. 

Toxicity Endpoint 

(Measured/ 

Nominal) 

Effect 

MRID (Year) 

Classification 

or Source 

Com

Acute 

850.5400 

122-2 

Green Algae 

(Selenastrum 

capricornutum) 

IMCA3

98.0 

EC50 > 0.035 mg IMCA/L 

(measured) 

Decrease of 4.1% in cell 

density compared to negative 

control 

Growth 43240800 

(1994) 

Acceptable 

DER 10/24/94 

Study conducted for 120 

at nominal conc. 

Abbreviations: TGAI = technical grade active ingredient; conc.=concentration 1 Based on mean measured test concentrations, but due to presence of precipitate or lack of reported test solution, true test concentration 2 LC or EC50 greater than reported water solubility of 0.189 mg/L flumiclorac-pentyl. 3 Due to rapid degradation of flumiclorac-pentyl and major degradate IMCA being mobile in soils and possibly bioactive, study conduc

herbicide Resource is applied at 0.0806 lb ai/A and degradate IMCA is 53% of parent, the maximum application rate for IMCA was 0.0

amount 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-pentyl 

Study Type Test Species TGAI or TEP 

Toxicity Endpoint 

(95% C.I.) 

(Measured/ 

Nominal)/ 

Slope 

Effect 

MRID (Year) 

Classification, 

DER date or 

source 

870.11 

Acute Oral 

Rat TGAI LD50 > 5000 mg/kg Mortality 42169812 

U.S. EPA 2005d 

870.11 

Acute Oral 

Rat TEP 

0.83 EC 

LD50 = 4100 mg/kg male 

LD50 = 3200 mg/kg female LD50 = 3600 mg/kg both 

Mortality 42169813 

U.S. EPA 2005d 

870.3100 

Subchronic Oral 

(90 day oral) 

Rat TGAI NOAEL = > 1359/1574 

mg/kg/day (M/F) 

LOAEL= not identified 

 42169823, 

42310801 

(1990) 

Acceptable 

U.S. EPA 2005d 

870.4300 

Chronic/Carcinog

-enicity Toxicity 

Rat TGAI NOAEL = > 744.9/919.4 mg/kg/day (M/F) 

LOAEL = not identified 

No evidence of carcinogenicity 

42883906 

(1992) 

Acceptable 

U.S. EPA 2005d 
67 of 87 

Study Type Test Species TGAI or TEP 

Toxicity Endpoint 

(95% C.I.) 

(Measured/ 

Nominal)/ 

Slope 

Effect 

MRID (Year) 

Classification, 

DER date or 

source 

870.4100b 

Chronic Toxicity 

Dog TGAI NOAEL = 100 mg/kg/day 

LOAEL = 1000 mg/kg/day 

Decreased body weight gain in male, 

increased clotting time, increased globulin 

levels, increased alpha-2 fraction of the 

serum protein electrophoresis in females 

42825817 

(1992) 

Acceptable 

U.S. EPA 2005d 

870.3800 

Reproduction and 

Fertility Effects 

Rat TGAI Reproductive NOAEL = 200 ppm 

LOAEL = 10,000 ppm Based on increases in pup death on day 0 

42169835 

(1991) 

Acceptable 

U.S. EPA 2005d 

Reproduc

affect

rep

Avian

850.2100 

Acute Oral 

Bobwhite Quail 

(Colinus 

virginianus) 

Age=16 wks. 

Bw= 170-186 g 

TGAI 

94.7 

LD50 > 2250 mg/kg-bw 

(nominal) (2131 mg 

ai/kg-bw) 

None observed 42169802 

(1990) 

Acceptable 

DER 4/28/92 

10 birds 

treatment. 

Group w

in

850.2100 

Acute oral 

Passerine 

Zebra Finch 

(Taeniopygia 

guttata)

TGAI 

98.3 

LD50 > 2000 mg/kg-bw None observed 48603301 

Acceptable 

Administe

850.2200 

Acute Dietary 

Bobwhite Quail 

(Colinus 

virginianus) 

Age = 10 days 

TGAI 

94.7 

8-day LC50 > 5620 

mg/kg-diet (nominal) 

(5322 mg ai/kg-diet) 

NOAEC = 5620 mg/kgdiet 

None observed 42169803 

(1991) 

Acceptable 

10 bird

Measured 

prepared 

101% of 

instead 

Necropsie

less th

temperatu

greater t

850.2200 

Acute Dietary 

Mallard Duck 

(Anas 

platyrhynchos) 

Age = 10 day 

TGAI 

94.7 

8-day LC50 > 5620 

mg/kg-diet (nominal) 

(5322 mg ai/kg-diet) 

NOAEC = 5620 mg/kgdiet 

None observed 42169804 

(1991) 

Acceptable 

DER 4/28/92 

10 bird

Measured 

prepared 

101% of 

instead 

Necr
68 of 87 

Study Type Test Species TGAI or TEP 

Toxicity Endpoint 

(95% C.I.) 

(Measured/ 

Nominal)/ 

Slope 

Effect 

MRID (Year) 

Classification, 

DER date or 

source 

Temperatu

lower th

850.2300 

Reproductive 

Bobwhite Quail 

(Colinus 

virginianus) 

Age = 32 wks 

TGAI 

94.6 

1-generation NOAEC = 

439 mg ai/kg-diet 

(measured) (highest test 

concentration tested) 

No mortality or 

reproductive 

effects attributed 

to treatment 

42825805 

(1992) 

Acceptable 

DER 2/4/94 

16 pens with 

Two morta

two lowest 

incidental 

stored 

recommend

37.5°C an

recommen

hours of lig

for firs

Reproductive Mallard Duck 

(Anas 

platyrhynchos) 

Age = 17 wks 

TGAI 

94.7 

1-generation 

NOAEC= 220 mg ai/kgdiet (measured) 

LOAEC = 432 mg ai/kgdiet 

Decrease in egg 

laying and 

regressed ovaries 

and testes 

42825806 

(1992) 

Acceptable 

DER 1/19/94 

16 pens with 

One mort

believed 

necropsie

instead of 

were set at 

instead o

70%. Eig

instead of 

of study

included w

ef

Terrestrial Invertebrates

850.3020 

Acute Contact 

Honey Bee 

(Apis mellifera 

L.) 

TGAI 

94.7 

LD50 > 106 μg/bee No treatment 

related mortality 

42169841 

(1990) 

Acceptable 

DER 4/14/92 

Bees were e

of flumiclo

with acet

ranged from 

14% 
69 of 87 

Study Type Test Species TGAI or TEP 

Toxicity Endpoint 

(95% C.I.) 

(Measured/ 

Nominal)/ 

Slope 

Effect 

MRID (Year) 

Classification, 

DER date or 

source 

Terrestrial Plants 

850.4100 

122-1 

Seedling 

Emergence 

Cabbage, corn 

cucumber, 

lettuce, oat, 

onion, 

perennial 

ryegrass, 

soybean, 

tomato, turnip 

IMCA1

98.0 

EC25 > 0.046 lb ai/A 

NOAEC < 0.046 lb ai/A 

Growth 43258001 

(1994) 

Acceptable 

DER 10/24/94 

14-day stu

nominal co

No tr

morpholog

in any t

significant 

shoot l

compa

Red

850.4250 

123-1 

Vegetative Vigor 

Corn, oat, 

onion, 

perennial 

ryegrass, 

soybean, 

tomato, 

cucumber, 

lettuce, radish 

and cabbage 

TEP 

10.6 

EC25 = 0.0027 lb ai/A – 

lettuce(dicot, dry weight) 

EC25 = 0.0410 lb ai/A – 

onion (monocot,dry 

weight and height ) 

NOAEC = 0.00031 lb 

ai/A 

Tomato (dicot, 

phytotoxicity) 

NOAEC = 0.040 lb ai/A 

Onion 

Growth 43347401 

(1994) 

Acceptable 

DER 10/24/94 

EPA toxa

provide E

used to calc

values repo

statement s

phy

1 Due to rapid degradation of flumiclorac-pentyl and major degradate IMCA being mobile in soils and possibly bioactive, study conduc

herbicide Resource is applied at 0.0806 lb ai/A and degradate IMCA is 53% of parent, the maximum application rate for IMCA was 0.0

amount 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 ENVIRONMENTAL PROTECTION AGENCY 

 WASHINGTON, D.C. 20460

MEMORANDUM 

SUBJECT: Request for Phototoxicity Study Protocol 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 (LDPHs) are a growing class of weed control 

chemicals (see partial listing attached). They 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. Scalla. 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, protoporphyrin IX is a 

powerful generator of singlet oxygen which in plants causes lipid membrane peroxidation 

leading to a rapid loss of turgidity and foliar burns. LDPH exposure in mammals has been 

shown to result in excretion of porphyrins in urine (porphynuria) and feces, increased liver 

weight, elevated blood porphyrin levels, developmental abnormalities, and cancer. Humans with 

a hereditary protox disorder (variegate porphyria) which results in lowered protox activity 

exhibit many symptoms similar to LDPH exposure in addition to photosensitivity. However, 

photosensitivity is not a commonly reported symptom of LDPH exposure in animals. 

An LDPH-induced occurrence of phototoxicity in rats8

 and increased cytotoxicity to human skin 

cells grown in culture in the presence of light and an LDPH9

 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 LDPHs 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) recommends that phototoxicity studies be conducted on 

herbicides with this mode of action to determine if animals exposed to LDPHs and intense light 

(similar to sunlight) show increased toxicity relative to controls exposed 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 risk than guideline toxicity studies suggest. 

The ABTT is requesting that a LDPH phototoxicity protocol be submitted for review and 

agreement by EFED and the registrant prior to study 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 radiation 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, American 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. 

10American Society for Testing and Materials. 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 Carbamate Insecticide to Early Life Stage Anuran 

Amphibians",5

 and other studies in the peer-reviewed scientific literature serve as sources of 

additional guidance: 

Species 

The fathead minnow may be an appropriate test species 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 accumulation, however, a life-cycle is not necessary 

to identify a phototoxic effect. 

Dosing

A range finding study should be conducted under defined low light conditions to identify an 

LC50 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 measurements 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 that will vary in different regions and seasons as 

well as with weather. If artificial light is used, the light should resemble 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 recommendation for an artificial light source. 

Dark, light, and positive controls

As this study is intended to identify potential effects of light on LDPH toxicity, an appropriate 

study protocol should include a dark, or low light, control group. Another group not exposed to 

chemicals but exposed to full light should be included (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 chambers 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 are believed to act by inhibiting protoporphyringen 

oxidase in the heme and chlorophyll biosynthetic pathway. 

acifluorfen azafenidin carfentrazone-ethyl 

flumiclorac-pentyl flumioxazin 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) 

C3 F

Cl

O

OCH2CH3

NO2
74 of 87 

Flumicloracpentyl 

(128724) 

F

Cl

O

O

O

N

O

O

Acifluorfen, 

sodium 

(114402) 

Carfentrazoneethyl 

(128712) 

Cl F

Cl

O

O

N

N

N

O

F

F

Flufenpyrethyl 

(108853) 

 

Flumioxazin 

(129034) 

N

N O

O

O F

O

HC
75 of 87 

Fluthiacetmethyl 

(108803) 

Fomesafen 

(123803) 

Lactofen 

(128888) 

Sulfentrazone 

(129081) 

 

F

F

F

Cl

O

N

H

O

S

O

CH3 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 Strawberry. GRO,PHY,POPSOIL,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 Carey, 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,BT,CLT,CMZ,CRM,CZE,DMB,DU,FMCP,FMU,FM

X,FNPPE,FSF,FZFP,IAZ,IMQ,IZT,LCF,LNR,MBZ,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,LNR,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 (Daucus 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,POPSOIL,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.; Olive, J. W.; Edwards, J. H.; Keever, G. J.; Kessler, J. R. Jr., and Eakes, D. J. 

Postemergence Control of Bittercress in Container-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 Environmental 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,Balcarce,Argent//: SOIL,ENV; 

1993; 14, 64-65. 

Rec #: 150 

Call Number: NO MIXTURE (BT), TARGET2012 (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. Adjuvant 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,FMC,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 (CLT), 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 Sensitivity to Peroxidizing Herbicides Among Corn Varieties. 

MOR,PHY. Grad. Sch. Agric. Sci.,Tamagawa 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. Interaction of Glyphosate with Postemergence Soybean (Glycine 

max) Herbicides. GRO,PHY,POP. J.M. Lich, Department of Crop and Soil Science, Michigan State 

University, East Lansing, MI 48824//: SOIL,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,ENV,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) Control in Corn (Zea mays). GRO,POP. Prof. W.S. 

Curran, Department of Agronomy, Penn State University, 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 Response 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 and Pyrithiobac in Palmer Amaranth (Amaranthus 

palmeri) from Mississippi and Response to Flumiclorac. BCM,MOR,PHYSOIL,ENV,MIXTURE; 

2012; 60, (2): 179-188. 

Rec #: 160 

Call Number: OK (ALSV,MOIL), WEEDS (CRME,FMC,FMCP,FSF,GFSNH,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 Culpepper, A. S. Control of Volunteer Glyphosate-Resistant 

Cotton in Glyphosate-Resistant Soybean. POP. Department of Crop Science,North Carolina State 

University,Raleigh,NC//: SOIL,ENV,MIXTURE; 2004; 18, (3): 532-539. 

Rec #: 70 

Call Number: TARGET2012 (CLNS,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,MIXTURE; 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. Environmental 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,CLT,CMZ,DMB,FMC,FTCM,GYP,IZT,MBZ,MTL,NSF 

 6. Frans, R.; McClelland, M.; Jordan, D., and Johnson, 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,CLT,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,FMCP), 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. Glyphosate 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 Yellow 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,GYPI,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//: SOIL,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 Herbicides 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., and Scherder, E. F. Field Evaluation 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,PHMD,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. Evaluation of Contact Herbicides as a Follow-up Treatment for 

Cotton Defoliation. PHY,POP. University of Arizona,Phoenix,AZ,USA////: 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 Flumiclorac-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 AminesFW fish chronic nd 5.749 (ACR) acid 

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 

FW fish acute (14 d) nd 0.701 (Unhindered) 

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 

FW fish acute (14 d) nd 1099 (Unhindered)-acid 

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 

FW fish acute (14 d) nd 120 (Unhindered) 

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 OrganicsFW fish acute (14 d) nd 1403 acid 

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 = 

3.6x105

 mg/ L 

(estimated) 

FW fish acute nd 85460 Neutral OrganicsFW fish acute (14 d) nd 81317 acid 

FW fish chronic nd 6762 

Daphnid acute nd 40673 

Daphnid chronic nd 2403 

SW fish acute nd 1.06 x105

SW fish chronic nd 3530 

Mysid acute nd 2.94 x105

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