### Page | 1 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY WASHINGTON D.C., 20460 Office of Chemical Safety And Pollution Prevention

MEMORANDUM Date: 06.01.11 Subject: Registration Review

– Preliminary Problem Formulation for Ecological Risk and

Environmental Fate, Endangered Species, and Drinking Water Assessments for Flumioxazin (PC Code 12 9034 ; D 386128 ) To: Jack Brennan, RiskManager Reviewer

Robert McNally, Risk Manager Risk Manageme nt and Implementation Branch (RMIB 4) Pesticide Re

- evaluation Division (PRD) Office of Pesticide Programs From: Joseph DeCant, Ecologist

Larry Liu, Chemist Environmental Risk Branch 5 Environmental Fate and Effects Division (EFED) Office of Pes ticide Programs Through: Mah Shamim, PhD, Chief

Environmental Risk Branch 5 Environmental Fate and Effects Division (EFED) Office of Pesticide Programs The Environmental Fate and Effects Division (EFED) has completed the preliminary problem formulation (attached) for the ecological risk, environmental fate, endangered species, and drinking water assessments to be conducted as part of the Registration Rev iew of the herbicide, flumioxazin . The problem formulation draws on information from both open literature and studies submitted by the technical registrants in response to data requirements. This document is intended to provide an overview of what is currently known regarding the environmental fate and ecological ef

fects associated with flumi oxazin and all of its degradates and outlines uncertainties regarding attributes of the parent compound and its transformation products. It describes the preliminary ecological risk hypothesis and the processes that will be used during the completion of d rinking water and ecological risk assessments in support of registration review. This document also recommends studies that should be included in a data call

- in (DCI) to address uncertainties surrounding the environmental fate and potential ecological eff ects of flumioxazin

.

### Page | 2 

# Problem Formulation for the Environmental Fate and Ecological Risk, Endangered Species, and Drinking Water Assessments in Support of the R egistration Review of Flumioxazin

PC 129034, D386128

Flumioxazin (CAS 103361 - 09 - 7 )

Date: 06.01.11 Pr epared by: Joseph DeCant, Ecologist Larry Liu, Chemist U. S. Environmental Protection Agency Office of Pesticide Programs Environmental Fate and Effects Division Environmental Risk Branch IV 1200 Pennsylvania Ave., NW Mail Code 7507P Washington, DC 20460 Reviewed by: Mah Shamim, PhD, Branch Chief

### Page | 3 Table of Contents

I. Purpose

................................ ................................ ................................ ................................ ....... 5 II. Problem Formulation

................................ ................................ ................................ ................. 5 A. Nature of Regulatory Action

................................ ................................ ................................ . 5 B. Conclusions from Previous Risk Assessments

................................ ................................ ...... 6 1. Flumioxazin Ecologic al Risk Assessments

................................ ................................ ........ 6 2. Drinking Water Exposure Assessments

................................ ................................ ............ 6 III. Stressor Source and Distribution

................................ ................................ .............................. 7 A. Mechanism of Action

................................ ................................ ................................ ............ 7 B. Overview of Pesticide Usage

................................ ................................ ................................ 7 C. Environmental Fate and Transport

................................ ................................ ........................ 9 1. Summary

................................ ................................ ................................ .......................... 9 2. General Physical

- Chemical and Fate Properties

................................ .......................... 10 3. Abioti c Degradation

................................ ................................ ................................ ....... 11 4. Biotic Degradation

................................ ................................ ................................ ......... 14 5. Sorption and Soil Column Leaching

................................ ................................ .............. 18 6. Terrestrial Field Dissipation

................................ ................................ ......................... 20 7. Aquatic Field Dissipation

................................ ................................ .............................. 23 8. Bioconcentration (BCF)

................................ ................................ ................................ . 24 9. Method Validation

................................ ................................ ................................ ......... 24 10. Degradate Profile and Metabolism Pathways

................................ ............................... 25 IV. Receptors

................................ ................................ ................................ ............................... 25 A. Effects to Aquatic Animals

................................ ................................ ................................ . 29 1. Freshwater Fish

................................ ................................ ................................ ............. 29 2. Freshwater Invertebrates

................................ ................................ ............................... 29 3. Estuarine/Marine Fish

................................ ................................ ................................ ... 29 4. Estuarine/Marine Invertebrates

................................ ................................ ..................... 29 B. Effects to Terrestrial Animals

................................ ................................ ............................. 30 1. Mammalian Species

................................ ................................ ................................ ....... 30 2. Avian Species

................................ ................................ ................................ ................. 30 3. Non

- target Insects

................................ ................................ ................................ .......... 30 C. Effects to Plants

................................ ................................ ................................ ................... 30 D. Degradate toxicity

................................ ................................ ................................ ............... 31 E. Ecological Incidents

................................ ................................ ................................ ............ 32 F. Ecosystems Potentially at Risk

................................ ................................ ............................ 33 V. Assessment Endpoints

................................ ................................ ................................ ............. 33 VI. Conceptual Model

................................ ................................ ................................ ................... 33 A. Risk Hypothesis

................................ ................................ ................................ .................. 34 B. Conceptual Diagram

................................ ................................ ................................ ............ 34 VII. Analysis Plan

................................ ................................ ................................ ........................ 37 A. Stressors of Concern

................................ ................................ ................................ ........... 38 B. Measures of Exposure

................................ ................................ ................................ ......... 38 C. Measures of Effect

................................ ................................ ................................ .............. 40 D. Integration of Exposure and Effects

................................ ................................ .................... 41 1. Deterministic and Probabil istic Assessment Methods

................................ ..................... 41 E. Endangered Species Assessments

................................ ................................ ....................... 42

### Page | 4

F. Endocrine Disruptor Screening Program

................................ ................................ ............. 42 G. Drinking Water Assessment

................................ ................................ ................................ . 43 H. Screening Imbibition Program

................................ ................................ ............................. 43 I. Screening Tool for Inhala tion Risk

................................ ................................ ...................... 44 J. Preliminary Identification of Data Gaps

................................ ................................ .............. 44 1. Fate

................................ ................................ ................................ ................................ .. 44 2 . Effects

................................ ................................ ................................ ............................... 47 VIII. References

................................ ................................ ................................ ........................... 49 Appendix 1. ECOTOX Accepted and Rejected Papers

................................ ............................... 55 Appendix 2. The Risk Quotient Method and Levels of Concern

................................ ................ 65 Appendix 3. Results from the Screening Imbibition Program

................................ ..................... 67 Appendix 4. Results from the Screening Tool for Inhalation Risk

................................ .............. 68

List of Tables Table 1. Application methods and rates for use of flumioxazin as an aquatic h erbicide.

............. 8 Table 2. General physical

- chemical and environmental fate properties of flumioxazin.

............ 10 Table 3. Major degradates detecte d at the end of 30

- day hydrolysis study for flumioxazin.

...... 11 Table 4. Adsorption coefficients for flumioxazin, estimated from column leaching studies.

..... 19 Table 5. Adsorption coefficients for two degradates of flumioxazin.

................................ ......... 19 Table 6. Most sensitive test species evaluated for assessing potential ecological effects of flumioxaz in and the associated acute toxicity classification.

................................ ....................... 27 Table 7. Flumioxazin toxicity reference values for terrestrial organisms.

................................ .. 28 Table 8. Available environmental fate data for flumioxazin and remaining data gaps.

.............. 45 Table 9. Ecological effects data requirements for flumioxazin and remaining data gaps.

.......... 48 List of Figures Figure 1. National flumioxazin use (in pounds per square mile) by major use category as of 2002..

................................ ................................ ................................ ................................ ............... 9 Figur e 2. Proposed degradation pathway of flumioxazin in an aquati c anaerobic metabolism system
................................ ................................ ................................ ................................ ........... 26 Figure 3. Conceptual model depicting stressors, exposure pathways, and potential effects to aquatic organisms from the use of flumioxazin

................................ ................................ ............ 35 Figure 4. Conceptual model depicting stressors, generic exposure pathways, and potential effects to terrestrial organisms (terrestrial plants, terrestri al invertebrates, and dietary routes of exposure for terrestrial vertebrates) from the use of flumioxazin.

................................ ................ 36 Figure 5. Conceptual model depicting stressors, drinking water and inhalation exposur e pathways, and potential effects to terrestrial anim als from the use of flumioxazin

..................... 37

### Page | 5



## I. Purpose The purpose of this problem formulation is to provide an understanding of the environmental fate and ecological effects of the registered uses of flu mioxazin . Flu mioxazin is a light

- dependent peroxidizing herbicide (LDPH) which acts by blocking heme and chlorophyll biosynthesis resulting in an endogenous accumulation of photo

- toxic porphyrins. This class of herbicides is kn own to have a photo

- toxic mode of action in plants and possibly in fish. Standard toxicity testing may not include light with the same wavelength or intensity as natural sunlight. LDPHs may be more toxic when exposed to natural sunlight, such as exposure conditions in the field. Thus, the results of this assessment may actually underestimate risk to an unknown extent. Flumioxazin is currently registered for various agricultural commodities a nd non - agricultural uses . It can be applied using a variety of methods including: band treatment, broadcast sprayer, burndown treatment, chemigation, impregnated dry bulk fertilizer, soil band , spot sprayer , and a water treatment. This document will provide a plan for analy zing data relevant to flumioxazin and for c onducting environmental fate and ecological risk, endangered species and drinking water assessments for its registered uses. Additionally, this problem formulation is intended to identify data gaps, uncertainties, and potential assumptions used to address those uncertainties, relative to characterizing the ecological risk associated with t he registered uses of flumioxazin

. 

## II. Problem Formulation A. Nature of Regulatory Action The Food Quality Protection Act of 1996 mandated EPA to implement a new p rogram for assessing the risks of pesticides, i.e ., registration review 1 

### . All pesticides distributed or sold in the United States generally must be registered by EPA. The decision to register a pesticide is based on the consideration of scientific data a nd other factors showing that it will not cause unreasonable risks to human health, workers, or the environment when used as directed on product labeling. 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 ensure that as change occurs, products in the marketplace can be used safely. As part of the implementation of the new Registration Review program pursuant to Section 3(g) of the Federal Insecticide, Fungicide and Rodenticide Act (FIFRA), the Agency is beginning its evaluation to determine whether f lumioxazin continues to meet the FIFRA standard for registration. This problem formulation for the environmental fate and ecological risk assessment chapter in support of the registration review is intended for the initial docket opening the public phase of the review process.

1 http://www.epa.gov/oppsrrd1/registration_r eview/

### Page | 6



## B. Conclusions from Previous Risk Assessments
Flu mioxazin was first registered in 2001

. The Agency conducted multiple subsequent assessments includ ing section 3 new chemical/new use (S3NU) and section 18 emergency exemptions (S18), as well as several drinking water assessments and experimental use permits (EUP) . These assessments serve as a basis for this problem formulation, and have primarily focused on risk concerns to plants , chronic risk to freshwater fish and estuarine/marine invertebrates , and chronic concerns for small herbivorous mammals. For aquatic uses, the major concerns are fr eshwater fish, invertebrates, and plants.

1

. Flumioxazin Ecological Risk Assessments Three experimental use permits were completed before the product was registered. Two EUP assessments w ere reviewed in 1993 (D194585, 194592 and D189771, respectivel y). O ne EUP was undated and unsigned; however , the DP barcode is listed as D222276. Ecological risk assessments completed for flu mioxazin include two emergency exemption (FIFRA Section 18) assessments . The first was conducted in 2001 for the use on cott on in Mississippi to control pigweed and in Louisiana on sugarcane to control morning glory (D274551

– MS; D274686

– LA)

. T he second was conducted in 2005 for use on alfalfa in Arizona to control common groundsel (D307331). The first S18 in 2001 identifi ed risk to terrestrial and aquatic plants, but not to any wildlife. Similarly, t he 2005 S18 assessment for use on alfalfa identified risk only to terrestrial and aquatic plants

. Seven section 3 risk assessments were conducted , 2 new chemical screens, a nd one aquatic EEC modeling exercise. The first S3NU in 2001 (D237259+) found risk for terrestrial and aquatic plants alone

. The next S3NU in 2003 (D274658+) showed chronic risk to small mammals as well as terrestrial and aquatic plants. It also identif ied chronic concerns for freshwater fish and estuarine/marine invertebrates. D274658 was an addendum to a previous risk assessment that revised the risk picture and found an exceedance of the LOC for small mammals and terrestrial and aquatic plants , as we ll as some chronic concern for freshwater fish and estuarine/marine invertebrates . Similarly, the S3NU in 2005 (D310413+) , 2007 (D338590+), and 2008 (D336090+) showed chronic risk for small herbivorous animals and terrestrial and aquatic plants. The aqua tic use S3NU showed acute and chronic risk to freshwater fish and invertebrates as well as aquatic plants.

2. Drinking Water Exposure Assessments Five drinking water exposure assessments were conducted, one in 1998 (D241401), 2003 (no DP barcode listed , dated July 7 2003), 2004 (D296445+), 2007 (D336195+), and 2010 (D357184) in support of human health risk assessments. In the first assessment for peanuts and soybeans, screening parent flumioxazin concentrations (based on the application rate of 0.1 lb ai/A) were 3.63 ppb and 0.13 ppb for respective acute and chronic exposures in surface water and 0.018 ppb for exposure in ground water. The second assessment from 2004 referred to a previous S3NU risk assessment from 2003 (D274658+). The 2007 drinking w ater assessment, which relied on the 2003 drinking water assessment (based on the yearly application rate of 0.76 lbs ai/A) shows

### Page | 7

screening concentrations for the parent flumioxazin and each of the three major degradates: 482

- HA, APF, and THPA at pH 7 (see below).

Peak Conc. in Surface Water Conc. in Groundwater Flumioxazin 1.03 ppb negligible 482

- HA 6.87 ppb 45.27 ppb APF 26.46 ppb 2.66 ppb THPA 27.67 ppb 182.28 ppb 

## III. Stressor Source and Distribution A. Mechanism of Action
Flumioxazin is a low use pre

- emergent herbicide proposed for the control o f a variety of weed species in both agrigultural and non

- agricultural settings. It is classified as a light dependent peroxidizing herbicide. It b elongs to a class of compounds called the protox inhibitors that act by inhibiting the enzyme protoporphyrinogen oxidase (protox), which is the last common enzyme in the heme and chlorophyll biosynthetic pathways (Matringe, 1989). Protox inhibition in plants results in a rapid accumulation of protoporp hyrin IX, a phototoxic heme and chlorophyll precursor. In the present of ultraviolet light, protoporphyrin IX can become a powerful source of singlet oxygen which in plants causes lipid membrane peroxidation leading to a rapid loss of turgidity and foliar burns. Protox exists in both plants and animals and the enzyme from both sources has be e n shown to be highly sensitive to many LDPHs (Birchfield and Casida , 1997). 

## B. Overview of Pesticide Usage Current labels allow the use of flumioxazin under the te rrestrial, aquatic, forestry, and indoor use groups. The labeled single maximum application rate ranges from 0.05 lbs ai/A (such as for potato) to 0. 38 l bs a.i./A (such as for apple) . The maximum application rate per crop cycle or per year is 0. 76 lbs ai /A (such as for grapefruits). Although the maximum application frequency was not reported for every use, it is reasonable to believe that the current labels allow up to two applications per crop cycle or per year with the application intervals ranging fro m 14 days (such as for sugarcane) to 60 days (such as for lemon). Current labels include four formulations: Water Dispersible Granules (Dry Flowable. DF), Emulsifiable Concentrate (EC), Granules (G), Soluble Concentrate (SC/S), and Wettable Powder (WP). It can be applied by aircraft, ground equipment, or chemigation. It should be noted that f

lumioxazin, the active ingredient of the herbicide CLIPPER (Reg. 59639

- 161), has been registered for control of aquatic weeds in bayous, canals, drainage ditches, la kes, marshes, fresh water ponds, and reservoirs throughout the U.S. Single active ingredient

### Page | 8

formulation is a water dispersible granule containing 51% active ingredient. The pesticide may be applied to waters with limited or no outflow by surface or subs urface application methods. The product should not be used in or near estuarine/marine areas or to any flowing waters. Application information for this aquatic use is listed in Table 1

. Table 1 . Application methods and rates for use of flumioxazin as an aquatic herbicide. Application method Single application rate (lb ai/A of water surface area) Application

interval (days) Maximum

application number per year Maximum application

rate per year (lb ai/A of water surface area/year) Surface application (aerial, ground, watercraft) 0.19

- 0.38 28 6 2.3 Subsurface application (use weighted trailing hoses to place chemical under the surface) 0.27

- 7.55 (Footnote 1) 28 6 45.3

Footnote 1 : In order to achieve 100 ppb flumioxazin in an o ne - foot deep water column, 0.27 lb ai/A of water surface area should be used. In order to achieve 400 ppb flumioxazin in a 7

- foot deep water column, 7.55 lb ai/A of water surface area should be used. It should be noted that the following statement was no t in the proposed label that was used in the ecological risk assessment and the drinking water assessment completed in 2010. The final label (59639

- 161) states that “when making applications to water bodies greater than 7 feet deep, do not exceed 7.55 lbs ai per surface acre”. 

### Figure 1 presents the national usage patt ern of flumioxazin in 2002. Usage was concentrated in the midwestern U.S., primarily in regions where corn and soybeans are grown (USGS 20 11 ). While this map shows the usage pattern, the data may not reflect current usage patterns

. Therefore this map should be seen as a snap

- shot in time for the usage of flumioxazin. The screening

- level use assessment (SLUA) national level estimates of agricultural uses of f l umioxazin indicate that the m ajor uses are soybeans ( 40%), corn (4%), peanuts (4%), pistachio (9%), grapes (13%), cotton (9%), and almonds (13%) (USEPA 2010 ). These uses account for roughly 92% of the total amount of flumioxazin that i s applied. State specific data for California sh ow that 68,000 pounds of flumioxazin was applied in 2006, 76,000 pounds in 2007, and 72,000 pounds in 2008 (CALDPR 2010) . Almonds, grape, pistachio, peach, alfalfa, cotton, and rights

- of

- way represented the major uses.

### Page | 9

Figure 1 . National fl umioxazin use (in pounds per square mile) by major use category as of 2002. Due to limitations in the data as it is from 2002, the uses have likely changed. This map provides a somewhat dated but still useful snapshot in time of flumioxaz in use. Source: U. S. Geological Survey ( http://water.usgs.gov/nawqa/pnsp/usage/maps/show_map.php?year=02&map=m9113 ). 

## C. Environmental Fate and Transport
1. Summary The following environmental fate assessment for f lumioxazin was based on the data submitte d by the registrant to support the Environmental Fate data requirements for the Terrestrial Food/Non

- Food Crop uses. Based on these data, f lumioxazin can be characterized as follows:

* Flumioxazin is relatively unstable to hydrolysis, especially in alka line media (half

- lives = 4.2, 1, and 0.01 days, respectively, at pH 5, 7, and 9). The three major degradates detected in the hydrolysis study are APF, THPA, and 482

- HA. * Flumioxazin photodegrades very rapidly in water and on soil (half

- lives = 1 and 5.8 days, respectively).

### Page | 10

* Flumioxazin degrades very rapidly under the soil metabolism and the aquatic metabolism conditions. * Flumioxazin is classified as having medium soil mobility potential. * Its two major degradates (APF and THPA) are expected to be mo re mobile than the parent compound in the environment (Koc = 410 and 155, respectively)

. * Although no mobility information on 482

- HA were available, based on its chemical structure, this degradate is expected to be very mobile, especially in the alkaline environment. * According to Henry‟s Law Constant, f lumioxazin volatilizes slowly. It is classified between “non

- volatile“ and “intermediate to high volatility” on dry non

- adsorbing surfaces under field conditions, based on its vapor pressure. * Flumioxaz in is not expected to bioaccumulate in fish (Kow = 355).

2. General Physical

- Chemical and Fate Properties Physico

- chemical properties of f lumioxazin are listed in Table 2 below. Based on the environmental fate properties for f lumioxazin, with consideration of the product formulation and application rates, EFED believes that the parent compound does not have the physical/chemical characteristics in common with pesticides that are known to leach to ground water or to move offsite to surface water. It should be noted that the Kd and Koc used in the water assessment for the parent compound were generated from the column leaching study (instead of the batch equilibrium study) due to the unstable nature of the parent compound in water. Physical and chemical pro perties for flumioxazin are listed below: Common Name: Flumioxazin Chemical Name (IUPAC): N

- (7

- fluoro

- 3,4

- dihydro

- 3

- oxo - 4

- prop - 2

- ynyl

- 2 H

- 1,4

- benzoxazin

- 6

- yl)cyclohex

- 1

- ene 1,2

- dicarboxamide CAS No.: 103361

- 09

- 7 PC Code: 129034
Table 2 . General physic al - chemical and environmental fate properties of flumioxazin.

Parameter Value Source Molecular Weight 354 g/mole Product Chemistry Melting Point 203C Product Chemistry Solubility (25C) 1.8 mg/L Product Chemistry Vapor Pres sure (22C) 2.4x10 - 6 mmHg Product Chemistry Henry‟s Law Constant (atm

- m 3 /mol) 6.2 x10 - 7 Estimated from Water Solubility and Vapor Pressure (also reported in MRID 45375512) Octanol

- Water Partition Coefficient (K ow ) (20C) 355 Product Chemistry Hydrolysis (pH 5) (t1/2)

(pH 7) (t1/2) (pH 9) (t1/2) 4.2 days 1 day 0.01 days 42697501

42684905 Aqueous photolysis (pH 5) (t1/2) 1 day 44295036 44295037

### Page | 11 45914601

Soil photolysis (t1/2) 3.2 and 8.4 days 44295038 44295039 Aerobi c soil metabolism (t1/2) 11.9 and 17.5 days 42684906 42884009 44295040 Anaerobic soil metabolism (t1/2) 0.2 and 0.2 days 44295041 Aerobic aquatic metabolism (t1/2) 3

- 5 days 47761801 Anaerobic aquatic metabolism (t1/2) 40.1 and 45.9 days 45914602 Adsor ption

- Flumioxazin (based on column leaching studies) 112, 271, 656, 1190 42684907 42684908 42684909 42884010 Adsorption

- APF (based on adsorption study) 201, 336, 391, 502, 620 45309202 Adsorption

- THPA (based on adsorption study) 13, 66, 75, 191, 248, 3 39 45309201



### 3. Abiotic Degradation Hydrolysis Flumioxazin hydrolyzes very rapidly. The hydrolysis rate increases as the pH of the solution increases. Two hydrolysis studies were submitted (MRID 42697501 and 42684905). The average half

- lives from the [Ph

14 

### C]

- S

- 53482 (uniformly ring labeled), and [THP

14 

### C]

- S

- 53482 (labeled at the 1

- and 2

- positions of the 3,4,5,6

- tetrahydro

- phthalimide moiety) hydrolysis studies were 4.2 days, 23 hours, and 18.3 minutes for the pH 5, 7, and 9 buffered solutio ns, respectively. Four degradates were observed; 7

- Fluoro

- 6[(2

- carboxy

- cyclohexenoyl)amino]

- 4

- (2

- propynyl)

- 1,4

- benzoxazin

- 3(2H)

- one (482

- HA), 6

- Amino

- 7

- fluoro

- 4

- (2

- propynyl)

- 1,4,

- benzoxazin

- 3(2H)

- one (APF), 3,4,5,6

- tetrahydrophthalic acid (THPA), and 3,4, 5,6

- Tetrahydrophthalic acid anhydride Delta

- TPA). Degradate 482

- HA was found at high concentrations (97.3% of the applied) in the pH 9 solution. APF and THPA were not detected in the pH 9 solutions, but were important components in the pH 5 and 7 solutio ns. Δ

- TPA was a minor component (8.8% of the applied) in the pH 5 and 7 solutions. Table 3 lists the major degradates detected in the hydrolysis study at pH 5, 7, and 9.
Table 3 . Major degradates detected at the end of 30 - day hyd rolysis study for flumioxazin. % of Applied Radioactivity Chemical pH 5 pH 7 pH 9 Flumioxazin Negligible 4.7 negligible 482

- HA Negligible 9.3 97.3 APF 41.8 40.0 negligible THPA 47.7 41.8 negligible 

### Aqueous Photolysis Flumioxazin photodegrades very rapidly in water. In the first study (MRID 44295036), uniformly phenyl ring

- labeled [ 14 

### C]Flumioxazin, at 0.1 ppm, degraded with a half

- life of 20.9 hours (r 2 

### = 0.99; 0

- 48 hour data) in sterilized pH 5 aqueous buffer solution which was irradiated with a xenon lamp (12 hour light/dark cycle) and maintained at 25 o 

### C for up to 720 hours. An

### Page | 12

unidentified major degradate (designated as Unknown 1), was initially 8.9% of the applied radioactivity at 2 hours post

- treatment, was a maximum of 74.6% at 96 hours, and was 23.7% at 720 hours. Another unidentified major degradate (designated as Unknown 3) reached a maximum of 16.8% at 720 hours post

- treatment. The minor degradate APF was detected twice, at 0.6% of the applied radioactivity at 8 hours post

- treatment and at 3.1% at 24 hours. Uncharacterized origin material initially (48 hours) accounted for 10.4% of the applied and was a maximum of 41.3% at 720 hours post

- treatment. In the second study (MRID 44295037), tetrahydrophthalimido ring

- labeled [1,2

- 14 

### C]Fl umioxazin, at 0.1 ppm, degraded with a half

- life of 26.3 hours (r 2 

### = 0.94; 0

- 48 hour data) in sterilized pH 5 aqueous buffer solution which was irradiated with a xenon lamp (12 hour light/dark cycle) and maintained at 25 o 

### C for up to 720 hours. The major degradate THPA was initially (5 hours) 3.7% of the applied radioactivity, was a maximum of 23.0% at 264 hours, and was 13.4% at 720 hours post

- treatment. An unidentified major degradate (designated as Area 1) was initially (2 hours) 25.2% of the applied r adioactivity, was a maximum of 54.1% at 48 hours, and was 6.8% at 720 hours post

- treatment. Another unidentified major degradate (designated as Area 3) was initially (408 hours) 19.4% of the applied radioactivity, and was a maximum of 35.1% at 720 hours p ost

- treatment. Uncharacterized origin material initially accounted for 13.7% of the applied radioactivity at 48 hours post

- treatment, increased to a maximum of 40.4% by 504 hours, and was 35.2% at 720 hours. In the third study (MRID 45914601), the aqueous phototransformation of [phenyl

14 

### C]

- and [tetrahydrophthaloyl

14 

### C]

- labeled flumioxazin was studied at 25 ± 1 C in sterile aqueous acetate buffer at pH 5 (0.01M acetate) at a nominal concentration of 1.0 μg a.i./mL under a 12

- hour light/12

- hour dark cycle using a UV

- filtered xenon lamp (290

- 800 nm) for 72 and 168 hours, respectively. For both labels, [ 14 

### C]flumioxazin degraded in a similar manner in the dark controls and irradiated solutions. In the irradiated buffer solution, [phenyl

14 

### C]

- and [THP

14 

### C]

- labeled flumioxazin decreased from averages of 96.30% and 96.14% of the applied at 0 hours, to 50.64% and 47.57% at 1 hour, and 2.23% and 2.42% at 6 hours, respectively; and was last detected in the [phenyl

14 

### C]

- label at 0.54% at 48 hours and in the [THP

14 

### C]

- label at 0.32% at 72 hours. Three major transformation products were identified associated with irradiated [phenyl

14 

### C]

- labeled flumioxazin: 482

- PHO averaged a maximum of 69.49% of the applied at 4 hours, decreasing to 0.30% at 72 hours (study termi nation); 482

- PHO

- ISO averaged a maximum of 14.98% at 24 hour, decreasing to 0.53% at 72 hours; 482

- PHO

- DC averaged a maximum of 9.98% at 48 hours (one sample 10.53%), decreasing to 4.78% at 72 hours. No minor transformation products were identified. The multiple peaks reported together and labeled as “others” were a maximum average of 69.71% of the applied with an average of 34 total peaks, and no one peak containing >6.4% of the applied at any sampling interval. At 72 hours, CO 2 

### was a maximum of 14.70% and volatile organics were 0.4% of the applied. Five major transformation products were identified and one unknown isolated that were associated with irradiated [THP

14 

### C]

- labeled flumioxazin: 482

- PHO averaged a maximum of 65.71% of the applied at 4 hour s, and was not detected at 168 hours; 482

- PHO

- ISO averaged a

### Page | 13

maximum of 11.35% at 24 hours, and was not detected at 168 hours; 482

- PHO

- DC averaged a maximum of 10.43% at 48 hours, decreasing to 1.12% at 168 hours; THPA and adipic acid averaged maximums of 17.92% and 10.48%, respectively at 168 hours (study termination). The unidentified major transformation product (Unknown 1) was an average maximum of 10.66% of the applied at 72 hours. No minor transformations products were identified. The multiple unid entified peaks reported together and labeled as “others” were a maximum average of 66.32% of the applied, with an average of 38 total peaks, and no one peak containing >8.9% of the applied at any sampling interval. At 72 and 168 hours, CO 2 

### was a maximum o f 0.6% and volatile organics were 0.4% of the applied. [Phenyl

14 

### C]

- and [THP

14 

### C]

- labeled flumioxazin were 12.7 and 10.1 hours (0

- 72 hour data), respectively. The observed half

- life in the irradiated buffer solution for the combined labels was between 0 and 1 hour. In the dark controls, the half

- life of the combined labels was 72.96 hours (0

- 72 hour data). [Phenyl

14 

### C]

- and [THP

14 

### C]

- labeled flumioxazin were 71.46 and 74.53 hours (0

- 72 hour data), respectively. Flumioxazin, degrades slowly via hydr olysis to 482

- HA which degrades to APF, or to THPA which degrades to adipic acid and on to minor polar compounds. Flumioxazin can also degrade quickly via photolysis to 482

- PHO which degrades to either 482

- PHO

- HA or 482

- PHO

- DC; 482

- PHO can also degrade t o 482

- PHO

- ISO which becomes 482

- PHO

- APF, or 482

- PHO can degrade directly to 482

- PHO

- APF as can 482

- PHO

- HA; 482

- PHO

- ISO can degrade to both 482

- PHO

- HA and 482

- PHO

- DC which can further degrade to THPA. Further degradation occurs forming CO 2 

### and minor polar degradates. Soil Photolysis In contrast to aqueous photolysis, Flumioxazin photodegrades relatively slowly on the soil surface. Two soil photolysis studies were submitted. In the first stud y (MRID 44295038), uniformly phenyl ring

- labeled [ 14 

### C]Flumioxa zin, at a nominal application rate of 2.5 ug/g (dry soil), degraded with a half

- life of 3.2 days (r 2 

### = 0.96) in sandy loam soil maintained at 25 o 

### C and irradiated with a xenon arc lamp on a 12

- hour light/dark cycle for up to 6 days. In the irradiated soil samples, the parent compound was initially 96.9% of the applied, decreased to 55.3% by 2 days and 34.5% by 4 days post

- treatment, and was 29.1

- 29.8% at 5

- 6 days. The minor degradate IMOXA was initially (time 0) 0.8% of the applied radioactivity, and incr eased to 3.1% by 6 days post

- treatment (the last sampling interval). The combined minor degradates APF and 482

- HA were initially (time 0) 1.4% of the applied radioactivity the irradiated samples, and were 0.6% at 6 days post

- treatment. Nonextractable [ 14 

### C] residues were initially (time 0) 3.0% of the applied radioactivity, increased to 16.4% by 1 day post

- treatment, and were 43.3% at 6 days. Evolved 14 

### CO 2 

### and [ 14 

### C] organic volatiles were negligible for the irradiated samples. In the second study (MRID 4 4295039), tetrahydrophthalimido ring

- labeled [1,2

- 14 

### C]Flumioxazin, at 2.5 ug/g (dry soil), degraded with a half

- life of 8.4 days (r 2 

### = 0.95) in sandy loam soil maintained at 25 o 

### C and irradiated with a xenon arc lamp on a 12

- hour light/dark cycle for up to 14 days. In the irradiated soil samples, the parent compound was initially 99.2% of the applied radioactivity, decreased to 82.2% by 7 days post

- treatment, and was 36.9

- 37.0% at 9

- 14 days. In the irradiated soil, the major degradate Delta

- TPA was initia lly (day 1) 0.3% of the applied radioactivity, was a maximum of 21.6% at 9 days post

- treatment, and was 8.6% at 14

### Page | 14

days. The major degradate THPA was initially (day 2) 2.7% of the applied radioactivity, increased to 7.4% by 9 days post

- treatment, and was a maximum of 12.9% at 14 days. The minor degradate 1

- OH

- HPA was detected twice, at 3.0% of the applied radioactivity at 9 days post

- treatment and 4.4% at 14 days. Uncharacterized residual radioactivity in the irradiated samples was initially (day 4) dete cted at 1.2% of the applied radioactivity, was a maximum of 17.3% at 9 days, and was 15.1% at 14 days. Evolved 14 

### CO 2 

### and [ 14 

### C] organic volatiles were not detected during the incubation period.

4. Biotic Degradation Parent Flumioxazin degraded relatively r apidly in soil under aerobic conditions and very rapidly in sediment/natural water systems under anaerobic conditions (half

- lives varied from 4.2 hours in the anaerobic aquatic metabolism study to 14.7 days in the aerobic soil metabolism study). Three rad ioactive studies were submitted. Aerobic Soil Metabolism Three aerobic soil metabolism studies were reviewed (MRID 42684906, 42884009 and 44295040). [ 14 

### C]

- Flumioxazin (uniformly phenyl ring labeled), at 0.26 ug/g, degraded with a half

- life of 11.9 days in a California sandy loam soil incubated in the dark at 22

- 26C. Flumioxazin was 92.9% of the applied at day 0 and decreased to 18.0% by day 28 and was 3.7% of the applied from day 89 post

- treatment. Four minor degradates were detected (482

- CA, 482

- HA, APF, and IMOXA). 14 

### CO 2 

### comprised 2.3% of the applied at day 0 and 11.5% of the applied at day 181 post

- treatment. Soil

- bound residues increased from 0.7% of the applied at day 0 to 52.7% by day 28 and 73.6% of the applied by day 181. The humic acid, fulv ic acid, and humin fractions in the soil

- bound residues ranged from 3.1

- 12.9%, 2.3

- 7.6%, and 7.4

- 24.9% of the applied, respectively. Material balances ranged from 88.9% to 104.5% of the applied throughout the study. [ 14 

### C]

- Flumioxazin (THP

- ring labeled) , at 0.245 ug/g, degraded with a half

- life of 17.5 days in a California sandy loam soil incubated in the dark at 24

- 26C. Flumioxazin was 97.3% of the applied at day 0 and decreased to 28.9% by day 30 and was 11.8% of the applied at day 91 post

treatment. 14 

### CO 2 

### comprised 0.2% of the applied at day 1 and 55.1% of the applied at day 91 post

- treatment. Four minor degradates were isolated and identified: THPA, Delta

- TPA, IMOXA, and 482

- CA. These compounds were present at concentrations of 6.6% of the applie d. Soil

- bound residues increased from 2.7% of the applied at day 0 to 20.0% by day 30 and 29.0% of the applied by day 91. The humic acid, fulvic acid, and humin fractions in the soil

- bound residues ranged from 0.9

- 7.0%, 3.5

- 8.0%, and 2.5

- 13.1% of the app lied, respectively. Material balances ranged from 96.4% to 101.3% of the applied throughout the study. Nonradiolabeled Flumioxazin, at a nominal application rate of 0.1 ppm, degraded with half

- lives of 5.0 days (r 2 

### = 0.96) in Wheeling sandy loam, 18.6 da ys (r 2 

### = 0.98) in Drummer clay loam, 18.9 days (r 2 

### = 0.88) in Dothan sand, and 15.6 days (r 2 

### = 0.96) in Webster loam soils incubated in darkness at 25.1 o 

### C for up to 44 days. Soil samples were adjusted to 79

- 84% of 0.33 bar moisture content and homogenize d by stirring, and the test vessels were capped. In the sandy loam soil, the parent was initially 0.1 ppm, decreased to 0.054 ppm by 6 days and 0.023 ppm by 13 days post

- treatment, and was below the LOQ by 16 days. In the clay loam soil, the parent

### Page | 15

was i nitially 0.098 ppm, decreased to 0.051 ppm by 16 days post

- treatment, was 0.046 ppm at 21 days, and was 0.017 ppm at 44 days. In the sand soil, the parent was initially 0.097 ppm, decreased to 0.053 ppm by 9 days and 0.043 ppm by 13 days post

- treatment, a nd was last detected at 0.034 ppm at 28 days. In the loam soil, the parent was initially 0.097 ppm, was 0.054 ppm at 9 days post

- treatment, and was last detected at 0.026 ppm at 28 days. Degradate compounds were not monitored. Anaerobic Soil Metabolism Uniformly phenyl ring

- labeled [ 14 

### C]Flumioxazin and tetrahydrophthaloyl ring

- labeled [1,2

- 14 

### C]Flumioxazin, at a nominal concentration of 50 ng/g, degraded with half

- lives of 4.2 hours (r 2 

### = 0.88; 0

- 6 hour data) and 4.3 hours (r 2 

### = 0.77; 0

- 6 hour data) in f looded sandy loam soil incubated anaerobically in darkness at 25 o 

### C for up to 182 days, respectively(MRID 44295041). Uniformly phenyl ring

- labeled [ 14 

### C]Flumioxazin, in the total system, was initially 90.2% of the applied, decreased to 48.1% by 2 hours a nd 32.9% by 6 hours post

- treatment, was 2.8

- 11.1% from 24 hours to 120 days, and was not detected following 120 days. In the water phase, the parent was initially 82.4% of the applied, decreased to 43.2% by 2 hours post

- treatment, was 4.8% at 24 hours, a nd was last detected at 1.2% at 7 days. In the water phase, the major degradate 482

- HA was initially 6.8% (time 0) of the applied, increased to 26.8% by 2 hours post

treatment, was a maximum of 45.4% at 24 hours, was 14.4% at 42 days, and generally decrea sed to 0.8% by 182 days. The major degradate SAT

- 482

- HA

- 2 was initially (hour 48) 0.6% of the applied, increased to 8.3% by 56 days post

- treatment, and was a maximum of 16.2% at 182 days. Uncharacterized radioactivity (designated as the PH

- polar fractio n) was initially (hour 2) 21.6% of the applied radioactivity, was a maximum of 46.6% at 48 hours post

- treatment, and generally decreased to 11.6% (5.6 ppb) by 182 days. Non

- extractable [ 14 

### C] residues in the soil were 10.6% of the applied at 7 days post

- t reatment, were 26.5% of the applied at 28 days, and increased to 60.4% by 182 days. Same degradates were detected in the second study in which tetrahydrophthaloyl ring

- labeled [1,2

- 14 

### C]Flumioxazin was used. Anaerobic Aquatic Metabolism The biotransforma tion of [phenyl

14 

### C]

- and [tetrahydrophthaloyl

14 

### C]

- labeled flumioxazin was studied in a pond water

- clay sediment (water pH 8.4, organic carbon not reported; sediment pH 6.4, organic matter 5.0%) from Mississippi for 360 days under anaerobic conditions in darkness at 25 ± 1 C. [ 14 

### C]Residues appeared to rapidly partition into the sediment, in both labels. However, over the course of the study, the partitioning was variable in the [phenyl

14 

### C]

- label, with the majority of the radioactivity in the sediment at 360 days, while radioactivity in the sediment of the [THP

14 

### C]

- labeled flumioxazin steadily declined, with the majority of the radioactivity in the water at 360 days. In the [phenyl

14 

### C]

- flumioxazin, the water:sediment ratio was approximately 1:3 from 0 to 7 hours, 1:1 at 1 to 3 days, 1:3 at 21 days, and finally 1:5 at 360 days (study termination). In [THP

14 

### C]

- flumioxazin, the water:sediment ratio was approximately 1:3 at 0 to 7 hours, 1:1 at 1 to 21days, 1:0.5 at 42 days, and finally 1:0.3 at 360 day s (MRID 45914602). In the [phenyl

14 

### C]flumioxazin solutions, flumioxazin in the total system decreased from 98.7% of the applied at time 0, to 89.0% at 7 hours, 41.9% at 1 day, 24.1% at 10 days, 2.6% at 59 days, and was 0.48% at 360 days (study terminati on). In the water layer, [ 14 

### C]flumioxazin was 20.7

-

### Page | 16

26.2% at 0

- 7 hours, 9.5% at 1 day, 5.3% at 7 days, 1.0% at 21 days, and not detected thereafter. In sediment extracts, [ 14 

### C]flumioxazin decreased from 74.1% at time 0, 68.3% at 7 hours, 32.4% at 1 day, 2 0.2% at 10 days, 8.6% at 42 days, 0.48% at 360 days. T hree major transformation products were identified, 6

- amino

- 7

- fluoro

- 4

- (2

- propenyl)

- 2H

- 1,4

- benzoxazin (APF), dihydro

APF (DAPF) and SAT

- 482

- HA. APF was detected in the water layer, sediment and total system at maximums of 49.1% of the applied (2 days), 19.3% (21 days) and 59.2% (2 days), respectively, and was not detected at 360 days. DAPF was detected in the water, sediment and total system at maximums of 8.88% of the applied (268 days), 13.5% (360 d ays) and 20.7

- 20.9% (268

- 360 days). SAT

- 482

- HA was detected in the water, sediment and total system at maximums of 8.60% (59 days), 8.97% (182 days) and 16.9% (182 days), respectively, and was 6.62%, 4.04% and 10.7%, respectively, at study termination (36 0 days). One minor unknown polar transformation product, UP

- 3, was reportedly detected only in the sediment at a maximum at 5.5% of the applied at 42 days. The peak, UP

- 1, was detected only in the sediment, and was not a single compound and contained at least 14 compounds 4.2%; at days 59 and 120 the largest peaks were Peak 4 (retention time 30.3 minutes) at a maximum of 4.2% of the applied and Peak 3 (retention time 19.4 minutes) at a maximum 1.7% of the applied, respectively. “Others” was detected in the water, sediment and total system at maximums of 4.64% of the applied (3 days), 5.48% (360 days) and 8.34% (3 days). Extractable sediment [ 14 

### C]residues decreased from 76.3% of the applied at time 0 to 45.4% at 1 day, and 32.9% at 360 days, while nonext ractable residues increased from 1.37% at time 0 to 2.08 at 1 day, and 48.3% at 360 days. Organic matter fractionation of 7

- 360 day extracted sediment found 8.01

- 43.1% and 2.80

- 8.29% of the applied associated with the humin and fulvic acids, respectively. Formation of volatilized 14 

### CO 2 

### was not significant totaling 0.25% of the applied at study termination; CH 4 

### was 0.25% of the applied at study termination. In the [THP

14 

### C]flumioxazin , flumioxazin in the total system decreased from 90.4% of the applied at time 0, to 85.7% at 7 hours, 38.5% at 1 day, 12.1% at 21 days, 0.4% at 268

- 360 days. In the water layer, [ 14 

### C]flumioxazin was 18.4% at time 0, 16.8% at 7 hours, 9.1% at 1 day, 3.7% at 7 days, 0.7% at 21 days and not detected thereafter. In sediment ex tracts, [ 14 

### C]flumioxazin decreased from 72.0% at time 0 to 68.9% at 7 hours, 29.4% at 1 day, 11.4% at 21 days, 4.6% at 42 days, 0.4% at 268

- 360 days. Two major transformation products were identified THPA and HPA. THPA was detected in the water layer, se diment and total system at maximums of 41.9% of the applied, 7.6% and 49.5% on day 1, respectively, and was not detected after 59 days. HPA was detected in the water, sediment and total system at maximums of 72.8% of the applied (360 days), 17.0% (42 days ) and 78.4

- 85.9% (182

- 360 days). Two minor transformation products were identified, 1

- OH

- HPA and SAT

- 482

- HA. 1

- OH

- HPA was detected in only in the water at a maximum of 4.71

- 4.76% (7

- 21 days). SAT

- 482

- HA was detected in the water, sediment and total syst em at maximums of 5.57% of the applied (268 days), 3.80% (42 to 59 days) and 8.65% (268 days). A polar unknown, TU

- 1, was detected only in the sediment at a maximum of 5.5% (10 days) of the applied. “Others” was detected in the water, sediment and total system at maximums of 3.95% of the applied (7 days), 4.23% (10 days) and 8.06% (10 days). Extractable sediment [ 14 

### C]residues decreased from 80.4% of the applied at time 0 to 19.4

- 19.6% at 268

- 360 days, while nonextractable residues were 1.67

- 7.19% during the 360 study period. No data was provided for organic matter fractionation. Formation of volatilized 14 

### CO 2 

### was not significant at 2.61% of the applied at 268 days; CH 4 

### was 1.38% of the applied at study termination.

### Page | 17

Based on first

- order linear regressi on analysis, flumioxazin in the total system (combined labels) dissipated with a calculated half

- life of 42.8 days; the individual half

- lives were 45.9 and 40.1 days for the phenyl and THP labels (0

- 360 days), respectively. Aerobic Aquatic Metabolism The biotransformation of [phenyl

- U

14 

### C]

- and [tetrahydrophthaloyl (THP)

- 1,2

- 14 

### C]

- labeled flumioxazin was studied in stream water

- clay loam sediment (water pH 7.80, dissolved organic carbon 16.8 mg/L; sediment pH 7.28

- 7.7, organic carbon 8.0%) and lake water

- s andy clay loam sediment (water pH 6.32, dissolved organic carbon 16.9 mg/L; sediment pH 5.3

- 6.4, organic carbon 3.6%) systems from the United Kingdom for 98 days under aerobic conditions in darkness at 20 2 C. Flumioxazin dissipated at similar rates in the two sediment systems. Calculated nonlinear half

- lives were 2 hours, 42

- 53 days and 3

- 5 days in the water layers, sediments and total systems, respectively. In general, the chromatographic profiles for each label were qualitatively and quantitatively similar for the two systems (MRID 47761801). Clay loam sediment systems (labels combined) . Following application of [ 14 

### C]flumioxazin to the water layer, mean (n = 2) distribution ratios (water:sediment) were 8:1 at day 0, 2:1 at 7 days, 1:1 at 14 days, 1:2 at 29 days, 1:3 at 60 days and 1:4 at study termination. Flumioxazin in the total system decreased from a mean 80.81% of the applied at day 0 to 21.17% at 7 days, 9.72% at 60 days and was 5.23% at study termination. In the water layer, flumioxazin d ecreased from 70.32% at day 0 to 2.10

- 3.31% at 7

- 14 days, 1.20% at 29 days and was 0.34

- 0.49% at 60

- 98 days. In the sediment, flumioxazin increased from 10.50% at day 0 to 19.07% at 7 days, and then was 9.38% at 60 days and 4.75% at study termination. In the system treated with the phenyl label, APF was detected at maximums (n = 1) of 42.02%, 4.99% and 47.01% of the applied in the water layer, sediment and total system, respectively, at 7 days, decreasing to 4.08%, 2.40% and 6.48%, respectively, at study termination. In the system treated with the THP label, THPA + Δ 1 

### TPA were detected at combined maximums of 49.16%, 18.60% and 65.81% in the water layer, sediment and total system, respectively, at 7

- 14 days, decreasing to 5.71%, 1.26% and 6.97%, respective ly, at study termination. SAT

- 482

- HA

- 2 was detected at maximums of 5.55% (98 days), 7.01% (60 days) and 12.13% (98 days) in the water layer, sediment and total system, respectively. IMOXA was detected at maximums of 2.72%, 4.06% and 5.65% in the water la yer, sediment and total system, respectively. 482

- HA was detected only in the water layer at a maximum 0.56%. SAT

- 482 was detected (TLC) at maximums of 0.79%, 0.46% and 1.25% in the water layer, sediment and total system, respectively. Unk@23.8 was dete cted at maximums of 21.82% in the water layer and total system, but only 1.67% in the sediment. Unk@5.5 was detected at maximums of 5.59%, 3.17% and 8.76% in the water layer, sediment and total system, respectively. Extractable sediment [ 14 

### C]residues wer e similar for both labels and increased from a mean 11.35% of the applied at day 0 to a maximum 33.75% at 14 days and were 17.45% at study termination. Nonextractable sediment [ 14 

### C]residues increased from ≤0.10% at day 0 (both labels) to maximums of 61.30% and 28.90% for the phenyl

- and THP

- label treated systems, respectively, at study termination. Organic matter fractionation of 60

- day extracted sediment found 22.90%, 8.40% and 1 4.10% of the applied associated with the humin, fulvic acids and humic acids, respectively, for phenyl

- label treated systems, and 6.20%, 13.70% and 7.30%, respectively, for THP

- label systems. Partition of the 60

- day fulvic acids found 77.38

- 93.43% and 6.5 7

- 22.62% of the sample radioactivity associated with the aqueous and organic phases, respectively.

### Page | 18

Sandy clay loam sediment systems (labels combined) . Following application of [ 14 

### C]flumioxazin to the water layer, mean (n = 2) distribution ratios (water:s ediment) were 9:1 at day 0, 3:1 at 7 days, 2:1 at 14 days, 1:1 at 29 days, 1:6 at 60 days and 1:15 at study termination. Flumioxazin in the total system decreased from a mean 84.26% of the applied at day 0 to 12.04% at 7 days, 10.88% at 60 days and was 4. 68% at study termination. In the water layer, flumioxazin decreased from 74.49% at day 0 to 2.22

- 2.84% at 7

- 14 days, 1.13% at 60 days and was not detected at study termination. In the sediment, flumioxazin increased from 9.77% at day 0 to 15.57% at 29 da ys, then was 9.75% at 60 days and 4.68% at study termination. In the system treated with the phenyl label, APF was detected at maximums (n = 1) of 57.68% of the applied in the water layer and total system at 7 days, decreasing to 2.95%, 4.90% and 7.85% in the water layer, sediment and total system, respectively, at 14 days, and was in the water laye r only at 0.50

- 1.19% at 60

- 98 days. In the system treated with the THP label, THPA + Δ 1 

### TPA were detected at combined maximums of 62.82%, 13.49% and 73.91% in the water layer, sediment and total system, respectively, at 7

- 14 days, decreasing to 2.40%, 0.26 % and 2.66%, respectively, at 60 days, and was in the water layer only at 0.68% at study termination. SAT

482

- HA

- 2 was detected at maximums of 4.34%, 5.23% and 9.57% in the water layer, sediment and total system, respectively. IMOXA was detected at maxim ums of 1.62%, 1.72% and 3.34% in the water layer, sediment and total system, respectively. 482

- CA was detected only in the water layer at a maximum 1.88%. SAT

- 482 was detected (TLC) at maximums of 0.14%, 0.24% and 0.29% in the water layer, sediment and t otal system, respectively. Unk@23.8 was detected at maximums of 6.76%, 3.41% and 8.92% in the water layer, sediment and total system, respectively. Unk@5.5 was detected at maximums of 17.25%, 2.74% and 18.30% in the water layer, sediment and total system , respectively. Extractable sediment [ 14 

### C]residues were similar for both labels and increased from a mean 10.25% of applied at day 0 to a maximum 25.95% at 29 days and were 12.75% at study termination. Nonextractable sediment [ 14 

### C]residues increased from 0.10% at day 0 (both labels) to a maximum 60.00% at study termination for the phenyl

label treated systems, but were a maximum 58.00% at 60 days for the THP

- label treated systems, decreasing to 47.00% at 98 days. Organic matter fractionation of 60

- day ex tracted sediment found 18.40%, 14.20% and 19.10% of the applied associated with the humin, fulvic acids and humic acids, respectively, for phenyl

- label treated systems, and 4.90%, 46.70% and 5.70%, respectively, for THP

- label systems. Partition of the 60

- day fulvic acids found 83.80

- 95.50% and 4.50

- 16.20% of the sample radioactivity associated with the aqueous and organic phases, respectively. 5. Sorption and Soil Column Leaching Mobility of Flumioxazin The potential for the parent compound to migrate into ground water and to move with surface runoff water is very low. Based on the organic carbon adsorption coefficients (K oc 

### ) obtained from the column leaching study, f lumioxazin is classified as a chemical with “moderately mobile” soil mobility potential (m ean K oc 

### = 557) (MRID 42684907, 42684908, 42684909 and 42884010) ( Table 4 ).

### Page | 19

Table 4 . Adsorption coefficients for flumioxazin, estimated from column leaching studies. Soil Kd Koc Plainfield sand 0.5 271 California College sandy loam 0.8 112 Mississippi silt loam 7.7 1,190 Kewaunee clay loam 19.3 656 

### Flumioxazin is classified between “non

- volatile“ and “intermediate to high volatility” on dry and non - adsorbing surfaces under field conditions, based on its vapor pressure (2.4x10 - 6 

### mmHg at 22C). Since this chemical is applied to the soil surface by the band or broadcast method without subsequent incorporation, volatilization could play a role in the dissipation of the chemical in the environment. Mobility of 482 - HA, APF and THPA N o mobility information of 482

- HA were available, based on its chemical structure, this degradate is expected to be more mobile in the alkaline environment than in the acidic environment. Since 482

- HA was found in the pH 7 hydrolysis study at a level much lower than the other two degradates (APF and THPA), additional adsorption study for 482

- HA is not needed. According to the adsorption studies (MRID 45303201 and 453032202), degradates APF and THPA are classified “moderately mobile” ( Table 5 ).
Table 5 . Adsorption coefficients for two degradates of flumioxazin. Soil Type (Soil number) APF THPA Kd Koc Kd Koc Sandy loam 2.8 336 0.1 13 Loam 4.2 391 2.7 248 Sandy loam 6.0 502 0.8 66 Sandy loam 1.6 620 0. 9 339 Loam (sediment) 4.9 201 1.8 75 Clay n/a n/a 5.3 191 

### The mobility of phenyl ring

- labeled [U

14 

### C]6

- amino

- 7

- fluoro

- 4

- (2

- propynyl)

- 2 H

- 1,4

- benzoxazin

- 3(4 H )

- one (APF), a degradate of Flumioxazin, at nominal concentrations of 0.047

- 0.048, 0.13, 0.24

- 0.25, and 0.48

- 0.51 μ g/mL, was investigated in four soils (three sandy loam and one loam) and one sediment that were equilibrated for 4, 16 or 17 hours (soils) or 24 hours (sediment) at 25 o 

### C. Freundlich K ads 

### values were 1.611

- 5.970 for the sandy loam soi ls, 4.218 for the loam soil, and 4.907 for the sediment; corresponding 1/n values ranged from 0.780 to 0.988. K oc 

### values were 336

- 620 for the sandy loam soils, 391 for the loam soil, and 201 for the sediment. Freundlich K des 

### values were 5.315

- 18.672 for the sandy loam soils, 6.334

- 7.608 for the loam soil, and 10.214 for the sediment; corresponding l/n values ranged from 0.609 to 0.933. Reviewer

- calculated coefficients of determinations (r 2 

### ) values for K ads 

### vs. percent organic matter, K ads 

### vs. pH, and K ad s 

### vs. percent clay content were 0.221, 0.408, and 0.028, respectively. Freundlich K des 

### values were 5.315

- 18.672 for the sandy loam soils, 6.334

- 7.608 for the loam soil, and 10.214 for the sediment; corresponding 1/n values ranged from 0.609 to 0.966. Rev iewer

calculated coefficients of determination (r 2 

### ) values for K ads 

### vs . percent organic matter, K ads 

### vs .

### Page | 20

pH, and K ads 

### vs . percent clay content were 0.221, 0.408, and 0.028, respectively. [ 14 

### C]APF was stable in the soil/sediment slurries during the adsorpt ion equilibration phase, but degraded in two sandy loam soils and the loam soil during the desorption equilibration phase, comprising 54.5

- 89.2% of the radioactivity recovered. The mobility of [1,2

- 14 

### C]THPA, at nominal concentrations of 0.026

- 0.027, 0.06

- 0.07, 0.13, and 0.26

- 0.27 ug/mL, was investigated in five soils (three sandy loam, one loam, and one clay) and one sediment that were equilibrated for 4

- 8 or 48 hours at 25 o 

### C. The soil:solution ratios were 2:7 for the sandy loam soils, 1:8 for the loam and clay soils, and 1:7.9 for the sediment. Freundlich K ads 

### values were 0.108

- 0.866 for the sandy loam soils, 2.688 for the loam soil, 5.261 for the clay soil, and 1.836 for the sediment; corresponding 1/n values ranged from 0.895 to 1.015. K oc 

### values w ere 13

- 339 for the sandy loam soils, 248 for the loam soil, 191 for the clay soi;l, and 75 for the sediment, ranging from 13 to 339 for all soil/sediment types and 1/n values ranged from 0.895 to 1.015. Freundlich K des 

### values were 0.179

- 1.135 for the san dy loam soils, 4.186 for the loam soil, 6.971 for the clay soil, and 2.870 for the sediment; corresponding l/n values ranged from 0.641 to 0.949. Reviewer

- calculated coefficients of determinations (r 2 

### ) values for K ads 

### vs. percent organic matter, K ads 

### vs. pH, and K ads 

### vs. percent clay content were 0.446, 0.36, and 0.205, respectively.

6. Terrestrial Field Dissipation Based on the findings in the environmental fate laboratory studies, the major routes of dissipation of f

lumioxazin in the environment appear to be rapid hydrolysis, photolysis, and metabolism of the parent compound. Six field dissipation studies were included in the evaluation of the fate of f lumioxazin in the environment. Mississippi Field Dissipation Study in 1996 (MRID 44295045) Flumioxazin (Sumisoya ® 

### ; V

- 53482 WDG, 50.9% a.i.), broadcast applied once as a spray at a nominal application rate of 42.5 g a.i./A, dissipated with a half

- life of 10.3 days (r 2 

### = 0.97) on a plot of silt loam soil planted with soybeans (the day after application) in Mississippi. In the 0

- to 7.5

- cm depth, the parent was 0.070

- 0.071 ppm at 0

- 1 day post

- treatment, decreased to 0.051 ppm by 5 days, was 0.031

- 0.032 ppm from 8 to 14 days, and was last detected at 0.011 ppm at 28 days. The parent compound was not detected below the 0

- to 7.5

- cm depth. Samples were not analyzed for degradates of f lumioxazin. Illinois Field Dissipation Study in 1996 (MRID 44295044) Flumi oxazin (VP

- 53482 WP, 51.4% a.i.), broadcast applied once as a spray at a nominal application rate of 43.2 g a.i./A, dissipated with a half

- life of 12.5 days (0

- 28 day data; r 2 

### = 0.85) on a no - till bare ground plot (containing crop residues) of silt loam so il in Illinois. The observed first half

- life occurred between 3 and 7 or 14 days post

- treatment. The parent compound was initially present in the 0

- to 7.5

- cm depth at 0.069 ppm, decreased to 0.064 ppm by 3 days and 0.025 ppm by 7 days (the next sampling interval), was 0.029 ppm at 14 days, was 0.014

- 0.021 ppm from 21 to 59 days, and was not detected above the limit of quantitation following 59 days with the exception of 0.011 ppm (one of three replicates) at 122 and 241 days. The parent

### Page | 21

compound was not detected above the limit of quantitation below the 0

- to 7.5

- cm depth. Samples were not analyzed for degradates of Flumioxazin. Iowa Field Dissipation Study in 1996 (MRID 44295046) Flumioxazin (VP

- 53482 WDG , 50.9% a.i.), broadcast applied once as a spray at a nominal application rate of 42.5 g a.i./A, dissipated with a half

- life of 42.0 days (0

- 112 day data; r 2 

### = 0.94) on a plot of silt loam soil planted with soybeans in Iowa. However, dissipation was obser ved to be biphasic and the apparent first half

- life of the parent occurred between 21 and 28 days post

- treatment; data were variable over time. In the 0

- to 7.5

- cm depth, the parent compound was initially 0.062

- 0.066 ppm at 0

- 1 day post

- treatment, was 0.0 54

- 0.057 ppm from 3 to 7 days, decreased to 0.044 ppm by 14 days, then was 0.060 ppm at 21 days, was 0.029

- 0.020 ppm from 28 to 56 days, was 0.013 ppm (two of three replicates) at 112 days, and was not detected following 112 days with the exception of 0.01 4 ppm (one of three replicates) at 336 days. The parent compound was only detected once (day 14) in the 7.5

- to 15

- cm depth, at 0.012 ppm (one of three replicates), and was not detected above the LOQ at any other sampling interval or depth. Samples were not analyzed for degradates of Flumioxazin. North Carolina Field Lysimeter/Dissipation Study in 1996 (MRID 44295043) Uniformly phenyl ring

- labeled [ 14 

### C]Flumioxazin, applied at a nominal ap plication rate of 43.4 g a.i./A (0.348 mg/lysimeter) to lysimeter

- enclosed bareground plots of Dothan loamy sand soil in Clayton, NC, dissipated with a half

- life of 27 days (0

- 111 day data; r 2 

### = 0.97); the half

- life was determined from the parent compound detected in the 0

- to 3

- inch depth only. However, the observed first half

- life occurred between 17 and 27 days; only 32.4% of the applied remained as parent at 27 days. Dissipation was observed to be biphasic with the more rapid phase occurring through 1 11 days. Residue data were reported as parent equivalents. The parent compound was initially present in the 0

- to 3

- inch depth at 95.1% (0.102 ppm) of the applied radioactivity, was 59.5% (0.064 ppm) at 17 days and 32.4% (0.035 ppm) at 27 days, decreased to 13.2% (0.014 ppm) by 69 days, and was 5.1

- 5.5% (0.005

- 0.006 ppm) at 111

- 177 days. Unidentified radioactivity (designated as “Region 2"; fractions 15

- 22) was detected in the 0

- to 3

- inch depth at a maximum of 11.0

- 11.2% (0.012 ppm) from 17 to 43 days p ost

- treatment, and was 6.0

- 6.4% (0.006 ppm) from 111 to 177 days; unidentified radioactivity consisted of multiple components, each of which was <0.01 ppm. Non

- extractable [ 14 

### C] residues were 6.5% (0.007 ppm) of the applied radioactivity at 6 days post

- tr eatment, were 17.8% (0.019 ppm) at 17 days, and increased to 25.2

- 29.0% (0.027

- 0.031 ppm) by 43

- 177 days. Total [ 14 

### C] residues were not detected above 0.01 μ g/g (designated the limit of analysis) below the 3

- inch depth. [ 14 

### C]Residues were not detected in the leachate samples and were only detected once in the run

- off samples, at 0.02% (day 111) of the applied radioactivity. Indiana Field Lysimeter/Dissipation Study in 1996 (MRID 44295047) Uniformly phenyl ring

- labeled [ 14 

### C]Flumioxazin, applied as a pre

- emergent at a nominal application rate of 45 g a.i./A (0.361 mg/lysimeter) to lysimeter

- enclosed soybean plots of loam soil in Charlestown, IN, dissipated with a half

- life of 4. 8 days (0

- 16 day data; r 2 

### = 0.86); the half

life was determined only from the parent compound detected in the 0

- to 3

- inch depth. Dissipation was observed to be biphasic with the more rapid phase occurring through 16 days. The observed first half

- life oc curred between 0 and 2 days post

- treatment. Concentration data were reported as parent equivalents. The parent compound was initially present in the 0

- to 3

-

### Page | 22

inch depth at 88.5% (0.13 ppm) of the applied radioactivity, was 50.2% (0.060 ppm) at 2 days and 28.0

- 33.5% (0.032

- 0.045 ppm) from 5 to 9 days post

- treatment, and was 0.9% (0.001 ppm) at 106 days. The minor degradates APF and 482

- HA were detected at maximums of 8.2% (0.010 ppm, day 2) and 2.6% (0.004 ppm, day 0) of the applied radioactivity, respecti vely. The minor degradates 482

- CA and IMOXA were present at 1.9% (0.002 ppm, days 2 to72) and 1.3% (0.001 ppm, days 2 to 106) of the applied radioactivity, respectively. Total [ 14 

### C]residues were not detected above 0.01 ug/g (designated as the level of an alysis) below the 3

- inch depth. Nonextractable [ 14 

### C]residues were initially 7.5% of the applied radioactivity, were 28.6% at 2 days post

- treatment, increased to 51.7% by 5 days, and were a maximum of 93.1% at 316 days. California Field Lysimeter/Dissipat ion Study in 1999 (MRID 45375502) Soil dissipation/accumulation of N

- (7

- fluoro

- 3,4

- dihydro

- 3

- oxo - 4

- prop - 2

- ynyl

- 2H

- 1,4

- benzoxazin

- 6

- yl)cyclohex

- 1

- ene - 1,2

- dicarboxamide (Flumioxazin) under U.S. field conditions was conducted in a bare plot located within a mature walnut orchard at one site in Fresno, CA (ecoregion not reported). Flumioxazin was broadcast twice (30

- day interval) onto bare soil at a target application of 0.420 kg a.i./ha/application (total application rate of 0.84 kg a.i./ha) in a 7.6 x 97.5 m plot. Rainfall was supplemented with irrigation to reach 554% of the 30

- year average rainfall. The control plot was located approximately 15.2 m away from the treated plot. Soil samples were taken at 0 and 29 days following the first application and a t 0, 1, 3, 7, 10, 14, 28, 42, 60, 90, 120, 181, 239, and 365 days following the second application to a depth of 0

- 90 cm. Soil samples were extracted with acetone: 0.1N hydrochloric acid (5:1, v:v), partitioned into dichloromethane, cleaned up using flori sil column chromatography, and analyzed for Flumioxazin by gas chromatography using a nitrogen

- phosphorus detector. Soil samples were not analyzed for any degradates of Flumioxazin. The LOQ was 0.01 ppm and the LOD was 0.005 ppm. Samples were stored fro zen for up to 375 days prior to analysis. The measured zero

- time concentration of Flumioxazin in the 0

- 7.5 cm soil depth following the first application was 0.426 mg a.i./kg, which is 95.7% of the applied rate (reviewer

- calculated based on a theoretical c oncentration of 0.445 mg/kg in the 7.5

- cm soil depth). Flumioxazin dissipated to 0.053 mg a.i./kg (0

- 7.5 cm soil depth) by 29 days after the first application (one day prior to the second application). Following the second application, Flumioxazin dissip ated from a mean maximum concentration of 0.484 mg a.i./kg at 1 day after the second application to 0.298 mg a.i./kg by 10 days and 0.083 mg a.i./kg by 14 days, and was last detected at 0.015 mg a.i./kg at 239 days after the second application in the 0

- 7.5 cm soil depth. Flumioxazin was detected in the 7.5

- 15 cm soil layer at a mean maximum concentration of 0.049 mg a.i./kg immediately following the first application and was last detected above the LOQ at 0.037 mg/kg at 10 days after the second application . Flumioxazin was only detected above the LOQ once in the 15

- 30 cm soil layer, and was not detected above the LOD below that depth. Under field conditions at the test site, f lumioxazin had a half

- life value of 12.5 days. Flumioxazin was last detected in the soil above the LOD at the 239

- day posttreatment sampling interval and does not have the potential to carryover. The major route of dissipation of Flumioxazin under terrestrial field conditions could not be determined because no transformation product s were reported, the parent compound did not leach below 15 cm (with one exception), and volatilization and run

- off were not studied.

### Page | 23 7. Aquatic Field Dissipation

The aquatic field dissipation of flumioxazin (MRID 47550605) was studied using an unspecified size pond at one site in Iowa (average depth not specified; volume, 2.54 acre/ft) and a 0.469

- acre pond at one site in Florida (average depth, 4 ft; volume, 1.88 acre/ft). Water and sediment samples were collected from each test site at 0

- 2 hours, 12

- 14 h ours, and at approximately 1, 3, 5, 7, 14, 28, 60, and 90 days posttreatment. Pond water samples were collected at three depths: at 1 foot below the water surface, at mid depth, and at 1 foot above the pond bottom. Sediment samples were collected to a dept h of 10 cm. Upon collection of pond water samples, two 100

- mL samples were prepared from each composite sample, with one set of samples mixed with 10 mL of 100 mM pH 5 buffer solution. Acidified samples were used for the analysis of flumioxazin, and unalt ered samples were used for the analysis of the transformation products APF and 482

- HA. However, the major degradate (THPA) detected in the hydrolysis study was not determined in this aquatic field dissipation study. Results from the Iowa site are presente d below. Flumioxazin was detected in the pond water at a maximum mean concentration of 233 ppb (58.3% of the target rate; reviewer

- calculated) at 0

- 2 hours (top depth), and decreased to 135 ppb by 12

- 14 hours (top depth), 121 ppb by 1 day (top depth), 46. 6 ppb by 3 days (mid depth), 24.6 ppb by 5 days (bottom depth), 15.6 ppb by 7 days (bottom depth), and was last detected above the LOQ at 2.21 ppb (mean of two replicate detections) at 28 days posttreatment (bottom depth). T he transformation product 482

- HA was detected in the pond water at a maximum mean concentration of 320 ppb at 0

- 2 hours (top depth), and decreased to 277 ppb by 12

- 14 hours (top depth), 239 ppb by 1 day (top depth), 96.2 ppb by 3 days (mid depth), 46.9 ppb by 5 days (bottom depth), 32.9 ppb by 7 days (mid depth), 12.4 ppb at 14 days (bottom depth), and was last detected above the LOQ at 3.31 ppb at 28 days posttreatment (bottom depth). 482

- HA had a reviewer

- calculated linear, first

- order half

- life value of 4.9 days (r 2 

### = 0.9358), and a no nlinear (one

- compartment/two

- parameter) half

- live value of 2.6 days (r 2 

### = 0.9835) in pond water, calculated based on the reviewer

- calculated means across all sampling depths (0

- 28 day data). The transformation product APF was detected in the pond water at a maximum mean concentration of 15.8 ppb at 0

- 2 hours (top depth), and decreased to 11.4 ppb by 12

- 14 hours (top depth), 10.8 ppb by 1 day (top depth), 4.18 ppb (mean of two replicate detections) by 3 days (bottom depth), 3.44 ppb by 5 days (bottom depth), 1.99 ppb by 7 days (bottom depth), and was last detected above the LOQ at 1.21 ppb (mean of two replicate detections) at 28 days posttreatment (bottom depth). APF had a reviewer

- calculated linear, first

- order half

- life value of 10.5 days (r 2 

### = 0.6330), an d a nonlinear (one

- compartment/two

- parameter) half

- live value of 2.7 days (r 2 

### = 0.9738) in pond water, calculated based on the reviewer

- calculated means across all sampling depths (0

- 28 day data). Flumioxazin was detected in the pond sediment (0

- 10 cm dep th) at concentrations above the LOQ at two sampling intervals only, at a mean concentration of 25.4 ppb (mean of two replicate detections) at 12

- 14 hours and 17.7 ppb at 1 day posttreatment. The transformation product 482

- HA was detected in the pond sedim ent at a maximum mean concentration of 29.4 ppb (mean of two replicate detections) at 12

- 14 hours, and decreased to 23.5 ppb by 1 day, 12.0

- 13.9 ppb (single replicate detections) by 3

- 5 days, and was last detected above the LOQ at 16.2 ppb (mean of two rep licate detections) at 7 days posttreatment. 482

- HA had a reviewer

- calculated linear,

### Page | 24

first

- order half

- life value of 3.3 days (r 2 

### = 0.0798), and a nonlinear (one

- compartment/two

parameter) half

- live value of 2.5 days (r 2 

### = 0.6342) in pond sediment, based on all replicate concentration data which occur on intervals with replicate values above the LOQ (0.5

- 7 days; replicate values below the LOQ were assumed at 1⁄2 LOQ). The transformation product APF was not detected in the pond sediment above the LOQ at any sam pling intervals.

8. Bioconcentration (BCF) The Agency granted the registrant‟s waiver request because: 1) the observed octanol/water partition coefficient is smaller than 1,000 (log Kow = 2.55); and 2) degradation is quick in water with a half

- life of abou t one day at pH 7 and about 20 minutes at pH of 9. Based on the low octanol water partition coefficient (K ow 

### =355), Flumioxazin is not expected to accumulate in fish. According to a fish residue study (MRID 47550604) reviewed by RD, BCFs between the ed ible tissue in Bluegill and Catfish and the static water treated with 800 ppb flumioxazin during the seven samplings in the exposure period of 28 days ranged from 0.09

- 4.1 for flumioxazin, 0.2

- 1.3 for APF, and 0.04

- 2.6 for 482

- HA.

9. Method Validation The me thod validation for the determination of flumioxazin and its transformation products APF and 482

- HA in pond water and pond sediment was performed by EPL Bio

- Analytical Services (MRID 47550603) . Flumioxazin and its transformation products were applied sepa rately to pond water (10 mL) at 1 and 10 ppb, and to sediment (20 g) at 10 ppb (LOQ level) and 100 ppb (10x the LOQ level). Residues of flumioxazin in water were determined with the addition of pH 5 buffer. In pond water, average method recoveries (n = 5) at the LOQ level of 1 ppb for flumioxazin, APF, and 482

- HA were 89.6 ± 4.7%, 106 ± 11.5%, and 103 ± 3.86%, respectively; at the 10x LOQ level of 10 ppb, average method recoveries (n = 5) were 77.7 ± 5.22%, 98.5 ± 10.1%, and 100 ± 2.98%, respectively. Overall average method recoveries (n = 10) for flumioxazin, APF, and 482

- HA were 83.7 ± 7.82% (range 69.5

- 91.7%), 102 ± 11.0% (range 86.5

- 118%), and 102 ± 3.60% (range 95.9

- 107%), respectively. All relative standard deviations were <20% (range 2.97

- 10.8%)

. In pond sediment, average method recoveries (n = 5) at the LOQ level of 10 ppb for flumioxazin, APF, and 482

- HA were 84.1 ± 8.38%, 93.9 ± 9.10%, and 89.3 ± 10.0%, respectively; at the 10x LOQ level of 100 ppb, average method recoveries (n = 5) were 109 ± 7.33%, 106 ± 5.41%, and 120 ± 3.79%, respectively. Overall average method recoveries (n = 10) for flumioxazin, APF, and 482

- HA were 96.7 ± 15.1% (range 72.1

- 117%), 100 ± 9.52% (range 81.4

- 113%), and 105 ± 17.8% (range 81.2

- 126%), respectively. All rela tive standard deviations were <20% (range 3.16

- 17.0%).

### Page | 25 10. Degradate Profile and Metabolism Pathways

Twelve major degradates were detected in various laboratory abiotic and biotic fate studies

. These major degradates are 482

- A, APF, THPA, Δ

- TPA, adipic acid, 482

- PHO, 482

- PHO

- ISO, 482

- PHO

- DC, SAT

- 482

- HA

- 2, DAPF, SAT

- 482

- HA, HPA, and combined residues of THPA+ Δ

- TPA. Some of these major degradates decreased to relatively low levels at the end o f the studies. Since flumioxazin is relatively unstable to hydrolysis, especially in alkaline media (half

lives = 4.2, 1, and 0.01 days, respectively, at pH 5, 7, and 9), it is considered as the major route of dissipation in the environment. As a result , its three major degradates (APF, THPA, and 482

- HA) and the subsequent degradates detected in other fate studies will be assessed in Registration Review. Two metabolism pathways in the aquatic environment were proposed. Under the anaerobic aquatic met abolism environment, Flumioxazin degraded rapidly via hydrolysis of the phthalimide group to form 482

- HA which further degraded to THPA and APF. A second degradation pathway proceeded via reduction of the cyclohexene double bond in 482

- HA to form SAT

- 482

- HA. The author also stated that it was possible, but unlikely that reduction preceded hydrolysis. THPA degraded to HPA by reduction of the double bond in THPA or hydrolyzed (Michael type reaction) to 1

- OH

- HPA. The side chain alkyne in APF was reduced to DAPF. Degradation continued to form multiple polar fragments, sediment

- bound residues, methane and CO 2 

### ( Figure 2 ). Under the aerobic aquatic metabolism environment, the primary pathway involved hydrolytic cleavage and separation of the phthalimido and b enzoxazin moieties at the amine bridge to yield APF and THPA. Other products identified included Δ

- TPA, SAT

- 482

- HA

- 2, IMOXA, 482

- HA, 482

- CA, and SAT

- 482. Mineralization to CO 2 

### occurred with both moieties, but was most significant with the phthalimido mo iety. Formation of bound sediment residues was significant for both moieties. 

## IV. Receptors Acute and chronic toxicity data from studies submitted by pesticide registrants along with the available open literature are used to evaluate the potential dir ect and indirect effects of flumioxazin on aquatic and terrestrial receptors. This includes toxicity data on the technical grade active ingredient, degradates, and when available, formulated products ( e.g . “Six

- Pack” studies). The open literature studies are identified using EPA‟s ECOTOX database (USEPA 2007a), which employs a literature search engine for locating chemical toxicity data for aquatic life, terrestrial plants, and wildlife. ECOTOX is a source for locating single chemical toxicity data and p otential chemical mixture toxicity data for aquatic life, terrestrial plants, and wildlife. ECOTOX was created and is maintained by the USEPA, Office of Research and Development, and the National Health and Environmental Effects Research Laboratory's Mid

- Continent Ecology Division. The evaluation of both sources of data can also provide insight into the direct and indirect effects of flumioxazin 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.

### Page | 26

Figure 2 . Proposed degradation pathway of flumioxazin in an aquatic anaerobic metabolism system (MRID 45914602). 

### Consistent with the proces s described in the Overview Document (USEPA, 2004), the Agency has routinely relied on a surrogate species approach. Toxicological data generated from surrogate test species, which are intended to be representative of broad taxonomic groups, have

### Page | 27

been use d to extrapolate the potential effects on a variety of species (receptors) included under these taxonomic groups. For example, guideline data for freshwater fish have typically served as surrogates for aquatic

- phase amphibians and submitted studies for bi rds have served as surrogates for terrestrial

- phase amphibians and reptiles. For the purposes of Registration Review, the Agency will consider the best available data in an effort to provide additional refined endpoints for specified taxonomic groups for which guideline data on surrogate species are typically not available and large numbers of listed species occur. These taxa include aquatic

phase and terrestrial

- phase amphibians, freshwater mollusks, and reptiles. Based on an updated ECOTOX search, whic h will be conducted as part of the Registration Review preliminary risk assessment, EPA will consider both more and less sensitive endpoints for amphibians, freshwater mollusks, and reptiles, as compared to the registrant

- submitted data for surrogate speci es (i.e., freshwater fish are surrogates for aquatic

- phase amphibians, freshwater invertebrates are surrogates for freshwater mollusks, and birds are surrogates for terrestrial

- phase amphibians and reptiles) In situations where no additional open literatu re data are available to refine endpoints for amphibians, freshwater mollusks, and reptiles, the Agency will rely on registrant

- submitted data and open literature for surrogate test species, as specified above. The ECOTOX database was searched and a preli minary report prepared in March 2010. A number of studies were identified related to both wildlife and plants. A bibliography of the accepted and rejected papers can be found in Appendix 1

. Table 6 provides a summary of the aquatic taxonomic groups a nd the surrogate species tested to characterize the potential acute and chronic ecological effects of flumioxazin. Table 7 provides a summary of the terrestrial groups and surrogate species. In addition, the tables provide a preliminary overview of the p otential toxicity of flumioxazin as well as the study classifications.
Table 6 . Most s ensitive t est s pecies e valuated for a ssessing p otential e cological e ffects of f lumioxazin and the a ssociated a cute t oxicity c lassification. Expo sure Scenario Species Scientific Name Exposure Duration Toxicity

Reference Value (ppm) Endpoints

Affected Reference

(Classification) Freshwater Fish Acute Rainbow Trout Oncorhynchus

mykiss 96 hours LC50: 2.3 Mortality 426849

- 48 (Acceptable) Chronic Rain bow

Trout Oncorhynchus

mykiss NOAEC: 0.0077, LOAEC: 0.016 Growth (length

and wt.) 442950

- 12

(Acceptable) Freshwater Invertebrate Acute Waterflea Daphnia pulex 96 hours LC50: 5.5 Mortality 426849

- 50 (Supplemental) Chronic Waterflea Daphnia magna 21 da ys NOAEC: 0.028, LOAEC: 0.057 Reproduction,

survival, growth 442950

- 11

(Acceptable)

Estuarine Fish Acute Sheepshead Minnow Cyprinodon

variegatus 96 hours LC50: >4.7 Mortality 442950

- 10 (Acceptable) Chronic Data Gap Estuarine Invertebrates Acute Mysid Shrimp Mysidopsis

bahia 96 hours LC50: 0.23 Mortality 442950

- 09 (Acceptable) Chronic Mysid Mysidopsis 21 days NOAEC: Reproduction, 442950

- 13

### Page | 28 Shrimp bahia 0.015, LOAEC: 0.027 survival, growth (Acceptable)
Aquatic Plants Non Vascular Freshwater

Green Algae Pseudokirchneriell

a subcapitata EC50: 0.00102, NOAEC: 0.00079 442950

- 31 (Acceptable)

Freshwater Diatom Navicula

pelliculosa EC 50: 0.0014, NOAEC: 0.000041 442950

- 32 (Acceptable)

Marine Diatom Skeletonema

costatum EC50: 0.0192, NOAEC: 0.0019 442 950

- 33 (Acceptable)

Freshwater Blue

- green Algae Anabaena

flosaquae EC50: 0.00083, NOAEC: 0.000022 442950

- 34 (Acceptable)

Vascular Duckweed Lemna gibba 14 days EC50: 0.00049, NOAEC: 0.00022 442950

- 35 (Acceptable)

Table 7 . Fl u mioxazin t oxicity r eference v alues for t errestrial o rganisms. Exposure Scenario Species Scientific Name Exposure

Duration Toxicity

Reference Value Effects Reference (Classification) Mammals Acute Laboratory Rat Rattus

norvegicus Acute Oral >5000 Mortali ty 426849

- 11 426849

- 12 Chronic Laboratory

Rat Rattus

norvegicus 2

- generation

reproduction NOAEL: 100

LOAEL: 200 Number of

liveborn pups, decreased pup weights, reproductive organ abnormalities 426849

- 34

426849

- 35 426849

- 36

Birds Acute (Dose based) Bobwh ite Quail Colinus

virginianus >2250 Mortality 426849

- 45 (Acceptable) Acute (Dietary based) Bobwhite Quail Colinus

virginianus >5620 Mortality 426849

- 47 (Acceptable) Chronic Mallard

Duck Anas

platyrhynchos 21 weeks

Reproduction NOAEC: 250,

LOAEC: 500 Re ductions in

viable embryos and live 3wk embryos 442950

- 05

(Acceptable)

Nontarget Insect Acute Contact Toxicity Honey Bee Apis mellifera 48 hours >105 μg/bee Mortality 426849

- 51 (Acceptable) Plants Seedling Emergence Ryegrass

(Monocot) Lolium

perenne 2 1 days EC25: 0.0037 lb ai/A, NOAEL: 0.003 lb ai/A Dry weight 442950

- 29 (Acceptable)

### Page | 29 Lettuce (Dicot) Lactuca

sativa 21 days EC25: 0.0008 lb ai/A, NOAEL: 0.0004 lb ai/A Dry weight 442950

- 29 (Acceptable)
Vegetative Vigor Oat (Monocot) Avena sativa 21 days EC25: 0.0071 lb ai/A, NOAEL: 0.006 lb ai/A Dry weight 442950

- 30 (Acceptable)

Cucumber (Dicot) Cucumis

sativus 21 days EC25: 0.00008 lb ai/A, NOAEL: 0.00005 lb ai/A Phytotoxicity 442950

- 30 (Acceptable)


## A. Effects to Aquatic Animals
1. Freshwater Fish In acute toxicity studies conducted on coldwater and warmwater species, the 96

- hour LC 50 

### values for the technical grade material ranged from 2.3 to > 21 ppm, suggesting that Flumioxazin will be moderately to slightly toxic to freshwater fish on an acute basi s. An early life

- stage toxicity test conducted on rainbow trout show s that f lumioxazin significantly affected larval growth (length and weight) at concentrations with a LOAEC of 16.0 ppb and a no

- effect level of 7.7 ppb. 2. Freshwater Invertebrates Acute toxicity studies conducted on freshwater aquatic invertebrates suggest that the active ingredient of f

lumioxazin is moderately toxic on an acute basis. The 48

- hour LC 50 

### or EC 50 

### value was 5.5 mg/L. The chronic data indicate that f lumioxazin significantly r educed reproduction at concentrations equal to a LOAEC of 57 ppb and a NOAEC of 28 ppb and survival and growth (length and weight) at concentrations equal to 107 ppb (LOAEC) and 57 ppb (NOAEC)

.

3. Estuarine/Marine Fish Testing on sheepshead minnow resulted in an 96

- hour LC 50 

### of >4.7 mg/L, which is considered to be moderately toxic on an acute basis. No data were submitted to assess chronic risk to estuarine/marine fish.

4. Estuarine/Marine Invertebrates Acute toxicity testing on estuarine/marine invertebrate species with the technical product resulted in a 96

- hour LC 50 

### /EC 50 

### values ranging from 2.4 to 0.23 ppm which fall into the moderate to highly toxic acute classes for estuarine/marine invertebrates. The chronic data indicate that f

lumioxazin significantly reduced reproduction and growth (length and weight) at concentrations equal to 27 ppb (LOAEC) and 15 ppb (NOAEC) and survival at concentrations equal to 55 ppb (LOAEC) and 27 ppb (NOAEC)

.

### Page | 30



## B. Effects to Terrestrial Animals
1. Mammalian Species In toxicit y studies conducted on laboratory rats for the Agency's Health Effects Division (HED), f lumioxazin was practically non

- toxic to small mammals on an acute oral basis (LD 50 

### of 5000 mg/kg). Results from a chronic reproduction study indicate reproductive toxic ity at a LOAEL of 200 ppm (NOAEL of 100 ppm) with decreased number of live

- born pups and decreased pup weights being the endpoints affected. Increases in the incidence of reproductive organ abnormalities (predominately atrophied or hypoplastic testes and /or epididymides) were also noted that may imply an endocrine modulated pathway. Absolute organ weight for the testes, epididymides and prostate were significantly reduced at 300 ppm for F1 males.

2. Avian Species In an acute oral toxicity stud y conducted on bobwhite quail, the LD 50 

### for the technical product is > 2250 mg/kg. The results suggest that Flumioxazin is practically non

- toxic to birds on an acute oral basis. Subacute dietary toxicity studies conducted on mallard duck and bobwhite quail suggest th at Flumioxazin is also practically non

- toxic, with LC 50s 

### of > 5620 ppm for the technical grade active ingredient. An avian reproduction study on bobwhite quail indicated that there were no significant treatment related effects. The No Observable Adverse Effect Concentration (NOAEC) and the Low est Observable Adverse Effect Concentration (LOAEC) was determined to be 500 and >500 ppm, respectively. Also, an avian reproduction study using mallard ducks indicated that significant reductions in the number of v iable embryos and live 3

- week embryos were evident at the highest concentration (500 ppm). The No Observable Adverse Effect Concentration (NOAEC) and the Low Observable Adverse Effect Concentration (LOAEC) was determined to be 250 and 500 ppm, respectivel y.

3. Non

- target Insects Flumioxazin is practically non

- toxic to bees on an acute contact basis (LD 50 

### > 105 μ g/bee).


## C . Effects to Plants Flumioxazin is a light

- dependent peroxidizing herbicide (LDPH) which acts by blocking heme and chlorophyll biosynt hesis resulting in an endogenous accumulation of photo

- toxic porphyrins. This class of herbicides are known to have a photo

- toxic mode of action in plants. Standard toxicity testing may not include light with the same wavelength or intensity as natural su nlight. LDPHs may be more toxic when exposed to natural sunlight, such as exposure conditions in the field. The following is a summary of the submitted plant toxicity data currently available: MRID 44295029. Tier II seedling emergence non

- tar get phyto

- toxicity study using f lumioxazin. This study was scientifically sound and satisfies the guidelines for a seedling emergence study with terrestrial plants. The most sensitive monocot and most sensitive parameter was ryegrass and dry weight, respectively. The EC 50 

### and NOAEL for the study was 0.0037 lb ai/A and 0.003

### Page | 31

lb ai/A, respectively. The most sensitive dicot and most sensitive parameter was lettuce and also dry weight, respectively. The EC 25 

### and NOAEL for the study was 0.0008 lb ai/A and 0.0004 lb a i/A, respectively. MRID 442950 30. Tier II vegetative vigor non

- target phyto

- toxicity study using f lumioxazin. This study was scientifically sound and satisfies the guidelines for a vegetative vigor study with terrestrial plants. The most sensitive monoc ot and most sensitive parameter was oat and dry weight, respectively. The EC 50 

### and NOAEL for the study was 0.0071 lb ai/A and 0.006 lb ai/A, respectively. The most sensitive dicot and most sensitive parameter was cucumber and phyto

toxicity, respectively. The EC 25 

### and NOAEL for the study was 0.00008 lb ai/A and 0.00005 lb ai/A, respectively. MRID 442950 31. Toxicity to the freshwater green alga ( Selenastrum capricornutum ). This study was scientifically sound and satisfies the guidelines for an algal aqua tic plant toxicity study. (EC 50 

### = 1.02 ppb ai; NOAEC= 0.79 ppb ai; 95% CI of 0.82

- 1.26 ppb ai). MRID 442950 32. Toxicity to the freshwater diatom ( Navicula pelliculosa )

. This study was scientifically sound and satisfies the guidelines for a freshwater diat om toxicity study. (EC 50 

### = 1.4 ppb ai; NOAEC= 0.041 ppb ai; 95% CI of 1.3

- 1.6 ppb ai). MRID 442950 33. Toxicity to the marine diatom ( Skeletonema costatum )

. This study was scientifically sound and satisfies guideline requirements for a marine diatom toxici ty study. (EC 50 

### = 19.2 ppb ai; NOAEC= 1.9 ppb ai; 95% CI of 13.3

- 27.8 ppb ai). MRID 442950 34. 5

- day toxicity to the freshwater blue

- green alga ( Anabaena flosaquae ). This study was scientifically sound and satisfies the guideline requirements for an algal aquatic plant toxicity study. (EC 50 

### = 0.83 ppb ai; NOAEC= 0.022 ppb ai; 95% CI of 0.47

- 1.46 ppb ai). MRID 442950 35. Toxicity to the Duckweed ( Lemna gibba ). This study was scientifically sound and satisfies the guideline requirements for a tier II aquati c plant toxicity study. (EC 50 

### = 0.49 ppb ai; NOAEC= 0.22 ppb ai; 95% CI of 0.40

- 0.60 ppb ai).


## D

. Degradate toxicity Few data are available to assess the potential toxicity of flu mioxazin degradates. In the absence of data, the degradates are presumed to be as toxic as the parent compound. The previous risk assessment for flu mioxazin ( D357187+ ) identified the major degradate s of concern to be 482

- HA, APF and THPA. However, there are no data on these degradates related to their toxicity. Therefore EF ED will conservatively assume that they are equally as toxic as t he parent compound. EFED will address the aquatic exposure to flumioxazin through a total residues approach that includes concentrations of the parent, 482

- HA, APF, and THPA. However, due t o limitations in current terrestrial models in addition to the mobility and relative lack of persistence of the degradates, parent flumioxazin will be assessed in the terrestrial risk assessment.

### Page | 32



## E . Ecological Incidents Incident reports submitted to EP A since approximately 1994 have been tracked by assignment of “incident numbers” in an Incident Data System (IDS), microfiched, and then entered into a second database, the Ecological Incident Information System (EIIS; USEPA 2007b). An effort has also bee n made to enter information to EIIS on incident reports received prior to establishment of current databases. Incident reports are not received in a consistent format (e.g., states and various labs usually have their own formats), may involve multiple inc idents involving multiple chemicals in one report, and may report only part of a given incident investigation (e.g., residues). While some progress has been made in recent years in getting incident reports submitted and entered, there has never been the l evel of resources assigned to incidents that there has been assigned to the tracking and review of laboratory toxicity studies, for example. A preliminary review of the EIIS and the Avian Monitoring Information System (AIMS), which is maintained by the Am erican Bird Conservancy, indicates there are no incidents for wildlife. There are 151 incident reports involving te rrestrial exposure to flumioxazin that have been reported and none that involve animals . All incidents i nvolve plant damage. Flumioxazin w as applied to agricultural crops ( peanut , soybeans, cotton, and an unspecified crop ) and non

agricultural crops (railroad right

- of

- way). I n most cases the treated cro p itself was affected. Only four incidents showed that flumioxazin may have damaged c rop s via drift to another crop, though each of these incidents involved a mixture of herbicides

. It is therefore difficult to attribute these drift events conclusively to the action of flumioxazin. The magnitude of damage s ranged from a small area (5 acre s ) to the entire treated crop of 380 acres

. In addition to the incidents recorded in EIIS, additional incidents have been reported to the Agency in aggregated incident reports. Pesticide registrants report certain types of incidents to the Agency as aggr egate counts of incidents occurring per product per quarter. Ecological incidents reported in aggregate reports include those categorized as “minor fish and wildlife” (W

- B), “minor plant” (P

- B), and “other nontarget” (ONT) incidents. “Other nontarget” in cidents include reports of adverse effects to insects and other terrestrial invertebrates. For flumioxazin, registrants have reported a total of 37 minor incidents, which includes 29 plant related incidents and 8 wildlife incidents. In the risk assessmen t, the incidents will be further evaluated to determine if the reported incidents represent current patterns of use for flumioxazin. Examples of additional considerations are mitigation ( e.g ., reduced application rates), product cancellations, and changes in use patterns that have occurred since the date of the reported incidents. An absence of reported incidents should not be construed as the absence of incidents. Incident reports for non

- target organisms typically provide information only on mortality events and plant damage incidents. Except for phytotoxic effects in terrestrial plants, sublethal effects, such as reduced growth or impaired reproduction, are rarely reported. EPA‟s changes in the registrant reporting requirements for incidents in 1998 m ay account for a reduced number of reported incidents. Registrants are now only required to submit detailed information on „major‟ fish, wildlife, and plant incidents. Minor fish, wildlife, and plant incidents, as well as all other nontarget incidents, a re generally reported aggregately and are not included in the EIIS. In

### Page | 33

addition, there have been changes in state monitoring efforts due to a lack of resources. However, the incident data that are available suggest that exposure pathways for flumioxazin are complete and that exposure levels are sufficient to result in field

- observable effects. 

## F. Ecosystems Potentially at Risk The ecosystems potentially at risk are often extensive in scope; therefore, it may not be possible to identify specific ecosyste ms during the development of a nation

- wide ecological risk assessment. However, in general terms, terrestrial ecosystems potentially at risk could include the treated field and immediately adjacent areas that may receive drift or runoff. Areas adjacent t o the treated field 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 d own stream from, the treated site and might include impounded bodies such as ponds, lakes and reservoirs, or flowing waterways such as streams or rivers including all adjacent off

- channel habitats that are permanently or intermittently connected to flowing waters. For uses in coastal areas, aquatic habitat also includes marine ecosystems, including estuaries, embayment‟s, and near shore environments. 

## V. Assessment Endpoints Assessment endpoints represent the actual environmental value that is to be prote cted, as defined by an ecological entity (species, community, or other entity) and its attribute or characteristics (EPA 1998). For flumioxazin , the ecological entities include the following: birds, reptiles, terrestrial

- phase amphibians, mammals, freshw ater fish, freshwater aquatic

- phase amphibians and invertebrates, estuarine/marine fish and invertebrates, terrestrial plants, insects, aquatic plants, and algae. The attributes for each of these entities include growth, reproduction, and survival. 

## VI. Conceptual Model For a pesticide to pose an ecological risk, it must reach ecological receptors in biologically significant concentrations. An exposure pathway is the means by which a pesticide moves in the environ ment from a source to an ecological receptor. For an ecological pathway to be complete, it must have a source, a release mechanism, an environmental transport medium, a point of exposure for ecological receptors, and a feasible route of exposure. The con ceptual model for flumioxazin provides a written description and visual representation of the predicted relationships between flumioxazin , potential routes of exposure, and the predicted effects for the assessment endpoint. A conceptual model consists of two major components: risk hypothesis and a conceptual diagram (USEPA 1998).

### Page | 34

As discussed previously, numerous ecological risk assessments have been conducted by EFED for flu mioxazin , including new use national level risk assessment s, EUPs, and S18 assess ments. Each of these assessments will be used to inform the risk hypothesis for this problem formulation for flumioxazin. 

## A. Risk Hypothesis A risk hypothesis describes the predicted relationship among the stress or, exposure, and assessment endpoint response along with the rationale for their selection. For flumioxazin , the following ecological risk hypothesis is being employed for this national

- level ecological risk assessment: Given the uses of flumioxazin and its environmental fate

properties, there is a likelihood of exposure to non

- target terrestrial and aquatic organisms. When used in accordance with the label, flumioxazin results in potential adverse effects upon the survival, growth, and reproduction of non - target terrestrial and aquatic organisms. 

## B. Conceptual Diagram The environmental fate properties of flumioxazin indicate that runoff, erosion of sediment

- bound residues, and spray drift represent potential transpo rt mechanisms of flumioxazin to aquatic and terrestrial organisms. These transport mechanisms ( e.g . sources) are depicted in the conceptual models below ( Figures 3 , 4 , and 5 ) and result in the movement of flumioxazin into aquatic (water and sediment) and terrestrial (soil and foliage) habitats. The movement away from the site of application in turn represents exposure pathways for a broad range of biological receptors of concern (nontarget animals) and the potential attribute changes, i.e. , effects such a s reduced survival, growth and reproduction, in the receptors due to flumioxazin exposure.

### Page | 35

Figure 3 . Conceptual model depicting stressors, exposure pathways, and potential effects to aquatic organisms from the use of flumiox azin . Dotted lines indicate exposure pathways that have a low likelihood of contributing to ecological risk.

### Page | 36

Figure 4 . Conceptual model depicting stressors, generic exposure pathways, and potential effects to terrestrial o rganisms (terrestrial plants, terrestrial invertebrates, and dietary routes of exposure for terrestrial vertebrates) from the use of flumioxazin.

### Page | 37

Figure 5 . Conceptual model depicting stressors, drinking water and inhalation exposure pathways, and potential effects to terrestrial animals from the use of flumioxazin. Dotted lines indicate exposure pathways that have a low likelihood of contributing to ecological risk. 

## VII. Analysis Plan
I n order to address the risk hypothesis, the potential for adverse effects on the environment is estimated. The use, environmental fate, and ecological effects of flumioxazin are characterized and integrated to assess the risks. This is accomplished using a risk quotient (ratio of exposure concentration to effects concentration) approach. 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 o f likelihood and/or magnitude of an adverse effect. However, as outlined in the Overview Document (USEPA 2004), the likelihood of effects to individual organisms from particular uses of flumioxazin is estimated using the probit dose

- response slope and eit her the level of concern (discussed below) or actual calculated risk quotient values. This analysis plan will be revisited and may be revised depending upon the information submitted by the public in response to the opening of the Registration Review dock et for flumioxazin

.

### Page | 38



## A. Stressors of Concern The stressor s of concern are as follows: Terrestrial Environment: parent flu mioxazin Aquatic Environment: p arent flu mioxazin and major degradates ( 482

- HA, APF, and THPA) Exposures in terrestrial habitats wil l consider flu mioxazin alone. However, because the major degradates of concern are found in the aquatic environment and the parent flu mioxazin and major degradates are relatively mobile, they will be assessed in conjunction with parent flu mioxazin for aqu atic habitats. Evaluation of environmental pesticide mixtures is beyond the scope of this assessment because of the myriad factors that cannot be quantified based on the available data. Those factors include identification of other possible co

- contaminan ts and their concentrations, differences in the pattern and duration of exposure among contaminants, and the differential effects of other physical/chemical characteristics of the receiving waters ( e.g. organic matter present in sediment and suspended wate r). Evaluation of factors that could influence additivity/synergism is beyond the scope of this assessment and the capabilities of the available data to allow for an evaluation. However, it is acknowledged that not considering mixtures could over

- or und er - estimate risks depending on the type of interaction and factors discussed above. The assessment will, however, analyze the toxicity of formulated products (including formulations involving more than one active ingredient) and will determine whether for mulated products are more toxic than the technical grade active ingredient. 

## B. Measures of Exposure In order to estimate risks of flumioxazin exposures in aquatic and terrestrial environments, all exposure modeling a nd resulting risk conclusions will be based on maximum application rates and will be estimated for each use of flumioxazin . Measures of exposure are based on aquatic and terrestrial models that predict estimated environmental concentrations (EECs) of flum ioxazin . The models used to predict aquatic EECs are the Pesticide Root Zone Model coupled with the Exposure Analysis Modeling System (PRZM/EXAMS). The model used to predict terrestrial EECs on food items is T

- REX. The model used to derive EECs relevant to terrestrial and wetland plants is TerrPlant. These models are parameterized using relevant reviewed environmental fate data from registrant submissions and the literature; model input values will be consistent with the most recent version of the input parameter guidance (Version 2; EFED 2002). PRZM and EXAMS are simulation models coupled with the linkage program shell, PE5, which incorporates the standard scenarios developed by EFED. The models generate daily exposures and calculated 1

- in

- 10 year EE Cs of flumioxazin that may occur in surface water bodies adjacent to application sites. PRZM simulates pesticide fate and transport as a result of leaching, direct spray drift, runoff and erosion from an agricultural field, and EXAMS estimates environment al fate and transport of pesticides in a surface water body for a 30

- year period. The standard

### Page | 39

scenarios used for ecological pesticide assessments assume application to a 10

- hectare agricultural field that drains into an adjacent 1

- hectare water body that is 2 meters deep (20,000 m 3 

### volume) with no outlet. The combined models ( i.e. , PRZM/EXAMS) are designed to estimate pesticide concentrations found in the water body (standard pond) at the edge of the treated field. As such, they provide high

- end values of the pesticide concentrations that might be found in ecologically sensitive environments following pesticide application. The location of the field is specific to the crop being simulated using site

- specific information on the soils, weather, cropping, and management factors associated with the scenario. The crop/location scenario is intended to represent a high

- end exposure site on which the crop is normally grown. Based on historical rainfall patterns, the receiving water body receives multiple runof f events during the years simulated. Weather and agricultural practices are simulated for 30 years so that the 10

- year exceedance probability at the site can be estimated. The simulation is generated using 30 years of meteorological data, encompassing th e years from 1961 to 1990. Additional information on these models can be found at: http://www.epa.gov/oppefed1/models/water/index.htm

. 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 amphi bians. The 1

- in

- 10

- year 21

- day mean is used for assessing chronic exposure to aquatic invertebrates. A total residues approach will be used to estimate EEC‟s of parent flumioxazin and the major degradates ( 482

- HA, APF, and THPA) to be found in the aquati c environment. For all terrestrial exposure, parent flumioxazin alone will be assessed due to limitations in current modeling approaches. 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 Kenega nomograph, as modified by Fletcher et al. (1994), which is based on a large set of field residue data. The upper limit values from the nomograph represent the 95 th 

### percentile of residue v alues 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 p esticides, and 17 chemical classes. 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, applica tion rate and minimum incorporation depth. Available monitoring data will be used to qualitatively characterize exposure and compare with modeling results. The Agency is aware of monitoring conducted by storm water management agencies and this route of exposure will be considered in the assessment to the extent that data on flumioxazin are available. Two spray drift models, AGDisp and AgDRIFT are used to assess exposures of terrestrial plants to flumioxazin deposited in terrestrial habitats by spray dr ift. AGDisp (Teske and Curbishley 2003) is used to simulate aerial and ground applications using the Gaussian far

- field extension. AgDrift is used to simulate spray blast applications to orchard crops.

### Page | 40



## C. Measures of Effect Ecological effects data are used as measures of direct and indirect effects to biological receptors. Data were obtained from registrant

- submitted studies or from literature studies identified by ECOTOX. The ECOTOX was searched in order to provide more ecological effects data to bri dge existing data gaps. An initial search revealed a number of open literature articles related to the toxicity of flumioxazin on plants as well as wildlife. These articles will be reviewed, in addition to any new information from the open literature bas ed on an updated „refresh‟ of the ECOTOX search to be completed prior to the preliminary risk assessment , in order to address any remaining uncertainties for the taxonomic groups. The data from accepted papers and those rejected papers containing mixtures data will also be considered as part of the risk assessment. In addition, registrants are encouraged to formally submit any other relevant open literature to the Agency that could potentially be used to satisfy data requirements where data gaps exist and /or inform our understanding of the ecological effects toxicity profile of the active ingredient, degradates, or formulations, which are the subject of Registration Review. Registrant submissions of open literature will be subject to the same standards as the relevant open literature studies obtained from ECOTOX. Information on the potential effects of flumioxazin on non - target animals is also collected from the Ecological Incident Information System (USEPA 2007 b ) , which contain s 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 have included behavioral changes ( e.g. , lethargy, changes in coloration and effects olfaction). 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 flumioxazin 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 screening

- level assessment are the LD 50 

### , LC 50 

### and EC 50 

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

### is the amount of a material, given all at once, that is estimated to cause the death of 50% of the test organisms. LC stands for “Lethal Concentration” and LC 50 

### is the concentration of a chemical that is estimated to kill 50% of the test organisms. EC stands for “Effective Concentration” and the EC 50 

### is the concentration of a c hemical 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 NOEC. 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 NOEC is the No

- Observed

- Effects

- Concentration. For non

- listed plants, only acute

### Page | 41

exposures are assessed ( i.e. , EC 25 

### for terrestrial plants and EC 50 

### for aquatic plants); for listed plants, either the NOAE C or EC 05 

### is used. In the absence of data for either acute or chronic effects, the conservative assumption will be to presume that flumioxazin is toxic. There are no studies available that assess the chronic toxicity to freshwater invertebrates from co ntaminated sediment. Given the low Koc, Kow, and Kd values as well as the low toxicity of flu mioxazin to benthic invertebrates , they are not likely to be at risk from flu mioxazin

. According to the CFR 40, part 158 guidelines, a chronic sediment toxicity s tudy to aquatic invertebrates is required if the estimated environmental concentration (EEC) is > 0.1 of the acute LC 50 

### as noted above, AND the half

- life of the pesticide in the sediment is > 10 days in either the aerobic soil or aquatic metabolism studies and if any of the following conditions exist: A. The soil partition coefficient (Kd) is ≥ 50 B. The log Kow is ≥ 3 C. The Koc is ≥ 1000 According to these conditions, the maximum peak EEC (0.4 ppm for flumioxazin parent when applied directly to the aquatic environment ) based on the previous aquatic use risk a ssessment (D357187+) is less than 0.55 ppm (i.e., 0.1 * LC 50 

### ). Even though flumioxazin has a log Kow of 2.5, the Koc ranging from 112 to 1,190, and a Kd ranging from 0.5 to 19.3, f lumioxazin and its three major degradate s, given the assumption of equivale nt toxicity to the parent compound, do not meet the conditions defined above and chronic sediment toxicity will not be assessed. 

## D. Integration of Exposure and Effects Risk characterization is the integration of exposure and ecological effects character ization to determine the potential ecological risk from the use of flumioxazin 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 flumioxazin risks, the risk quotient (RQ) method ( Appendix 2 ) is used to compare exposure and measured toxicity values. EECs are divided by acute and chronic t oxicity values. The resulting RQs are then compared to the Agency‟s levels of concern (LOCs) (USEPA 2004). These criteria are used to indicate when flumioxazin‟s uses, as directed on the label, have the potential to cause adverse direct or indirect effec ts to non

- target organisms. As noted previously, where data are lacking on the toxicity of flumioxazin, risk will be presumed. 1. Deterministic and Probabilistic Assessment Methods The quantitative assessment of risk will primarily de pend on the deterministic point

- estimate based approach described in the risk assessment. An effort will be made to further qualitatively describe risk using probabilistic tools that the Agency has developed. These tools have been

### Page | 42

reviewed by FIFRA Scien tific Advisory Panels and have been deemed as appropriate means of refining assessments where deterministic approaches have identified risks. 

## E. Endangered Species Assessments Consistent with the Agency‟s responsibility under the Endangered Species Act (ESA), the Agency will evaluate risks to Federally

- listed threatened and/or endangered species from registered uses of flumioxazin . This assessment will be conducted in accordance with the Overview Document (USEPA 2004), provisions of the ESA, and the Ser vices‟ Endangered Species Consultation Handbook (USFWS/NMFS 1998)

. The assessment of effects associated with registrations of flumioxazin is based on an action area. The action area is considered to be the area directly or indirectly affected by the fe deral action, as indicated by the exceedance of Agency Levels of Concern (LOCs) used to evaluate direct or indirect effects. The Agency‟s approach to defining the action area under the provisions of the Overview Document (USEPA 2004) considers the results of the risk assessment process to establish boundaries for that action area with the understanding that exposures below the Agency‟s defined LOCs constitute a no

- effect threshold. For the purposes of this assessment, attention will be focused on the foot print of the action ( i.e. , the area where flumioxazin application occurs), plus all areas where offsite transport ( i.e. , spray drift, runoff, etc.) may result in potential exposure that exceeds the Agency‟s LOCs. Specific measures of ecological effect tha t define the action area for listed species include any direct and indirect effects and/or potential modification of its critical habitat, including reduction in survival, growth, and reproduction as well as the full suite of sublethal effects available in the effects literature. Therefore, the action area extends to a point where environmental exposures are below any measured lethal or sublethal effect threshold for any biological entity at the whole organism, organ, tissue, and cellular level of organiza tion. In situations where it is not possible to determine the threshold for an observed effect, the action area is not spatially limited and is assumed to be the entire United States. 

## F. Endocrine Disrupt or Screening Program As required under FFDCA section 408(p), EPA has developed the Endocrine Disruptor Screening Program (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 “natur ally 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 pot ential of a chemical substance to interact with the estrogen, androgen, and 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 t o 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 testing is designed to identify any adverse endocrine related effects caused by the substance, and establish a quanti tative relationship between the dose and the E, A, or T effect.

### Page | 43

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. Thi s list of chemicals was selected based on the potential for human exposure through pathways such as food and water, residential activity, and certain post

- application agricultural scenarios. This list should not be construed as a list of known or likely e ndocrine disruptors. Flumioxazin is not among the group of 58 pesticide active ingredients on the initial list to be screened under the EDSP. For further information on the status of the EDSP, the policies and procedures, the list of 67 chemicals, the te st guidelines and the Tier 1 screening battery, please visit our website: http://www.epa.gov/endo/

. 

## G. Drinking Water Assessment A drinking water assessment will be conducted to support future human health dietary risk assessments of flumioxazin. The drinking water assessment will incorporate model estimates of flumioxazin and its major degradates in surface water and ground water. Concentrations of flumioxazin residues in surface waters will be estimated using PR ZM/EXAMS (see description above). An Estimated Drinking Water Concentration (EDWC) of flumioxazin residues in ground water will be estimated using EFED‟s Tier I aquatic model SCI

- GROW (Screening Concentration in Ground Water). SCI

- GROW is a regression mo del used as a screening tool to estimate pesticide concentrations found in ground water used as drinking water. The output of SCI

- GROW represents the concentrations that might be expected in shallow unconfined aquifers under sandy soils, which is represen tative of the ground water most vulnerable to pesticide contamination likely to serve as a drinking water source. The drinking water assessment will also include available surface and ground water monitoring data with considerat ion of changes in use patte rns that may have occurred. 

## H. Screening Imbibition Program
The S creening I mbibition P rogram (SIP v.1.0, Released June 15, 2010) was used to calculate an upper bound estimate of exposure using flumioxazin‟s solubility (1.8 ppm), the most sensitive acut e and chronic avian toxicity endpoints (>2250 ppm and 250 ppm, respectively) and the most sensitive acute and chronic mammalian toxicity endpoints (5000 ppm and 100 ppm, respectively). Drinking water exposure alone was not determined to be a potential p athway of concern for avian and mammalian species on an acute or chronic basis. See Appendix 3 for a screenshot of the input and output from SIP. Although drinking water exposure alone does not appear to be of concern, this does not take into account tha t when aggregated with other exposure pathways (dietary food sources, dermal, inhalation) drinking water may contribute to a total exposure that has a potential for effects on

### Page | 44

non - target animals and should be explored further. Because there is a high degr ee of conservatism in the SIP 1.0 exposure estimate, there is limited expectation that use scenarios not triggering a SIP 1.0 concern would contribute significantly to aggregate risks from water plus diet when a refined water exposure model is incorporated in the actual quantitative risk assessment. Detailed information about SIP v.1.0, as well as the tool, can be found on the EPA‟s website at http://www.epa.gov/pesticides/sc ience/models_pg.htm#terrestrial

. 

## I. Screening Tool for Inhalation Risk
The S creening T ool for I nhalation R isk (STIR v.1.0, November 19, 2010) was used to calculate an upper bound estimate of exposure using flumioxazin‟s vapor pressure and molecular wei ght for vapor phase exposure as well as the maximum application rate and method of application for spray drift. STIR incorporates results from several toxicity studies including acute oral and inhalation rat toxicity endpoints obtained from the “six

- pack” of core studies, which are a series of six guideline studies that are submitted to the Registration Division of the Office of Pesticide Programs for technical and formulated products of a pesticide (LD 50 

### of 5000 mg/kg and LC 50 

### of 3.93 mg/L) as well as the most sensitive acute oral avian toxicity endpoint (bobwhite quail with LD 50 

### of 2250 mg/kg). Based on the results of the STIR model, inhalation exposure alone was not determined to be a potential pathway of concern for either avian or mammalian species on an acute basis. Inhalation exposure via spray drift and vapor

- phase of the pesticide alone does not appear to be of concern. The analysis of the inhalation route of in STIR does not consider that aggregation with other exposure pathways such as dietar y, dermal, or drinking water may contribute to a total exposure that has a potential for effects to non

- target animals. However, the Agency does consider the relative importance of other routes of exposure in situations where data indicate that pesticide exposures through other routes may be potentially significant contributors to wildlife risk (USEPA, 2004). The risk characterization section of the risk assessment will discuss the impact of consideration of other routes of exposure that have been identifi ed as potentially important and the degree of certainty associated with screening

- level risk assessment conclusions. Detailed information about STIR v.1.0, as well as the tool, can be found on the EPA‟s website at: http://www.epa.gov/pesticides/science/models_pg.htm#terrestrial . For a sample of the output generated by STIR v.1.0, please see Appendix 4

. 

## J. Preliminary Identification of Data Gaps
1. Fate For fate and transport, Table 8 lists the status of the fate and transport data requirements for flumioxazin. The adequacy of the submitted data was evaluated relative to Agency guidelines. Re gistrants are required to submit both ECMs and associated ILVs in soil and water in order to support terrestrial field dissipation and ground water monitoring studies according to the Code of Federal Regulations (CFR) for a particular use pattern (40 CFR P art 158).

### Page | 45

Table 8 . Available environmental fate data for flumioxazin and remaining data gaps. Guideline # Data

Requirement MRID #’s Study Classification Is Data

Requirement Satisfied? 835.2120 Hydrolysis 42697501 42684905 Acceptable Acceptable Yes

835.2240 Photodegradation in Water 44295036

44295037 45914601 Supplemental Supplemental Supplemental Yes

835.2410 Photodegradation on Soil 44295038

44295039 Supplemental Supplemental Yes 835.4100 Aerobic Soil

Metabolism 42684906

42884009 44295040 Acceptable Acceptable Supplemental 835.4200 Anaerobic Soil

Metabolism 44295041 Supplemental Yes 835.4300 Aerobic Aquatic

Metabolism 47761801 Supplemental Yes 835.4400 Anaerobic Aquatic

Metabolism 45914602 Acceptable Yes

8 35.1240 Leaching 42684907 (parent) 42684908 (parent) 42684909 (parent) 42884010 (parent) Acceptable Acceptable Acceptable Acceptable Yes

835.1230 Adsorption/

Desorption 45309202 (THPA)

45309201 (APF) Acceptable Supplemental Yes

### Page | 46 835.6100 Terrestrial Field

Dissipation (ECM/ILV) 44295045 (completed in

1996) 44295044 (completed in 1996) 44295047 (completed in 1997) 44295046 (completed in 1996) 44295043 (completed in 1996) (the above studies included soil ECMs RM

- 30D and RM

- 30D

- 1) 44295042 (ILV for ECM RM

- 30D) 45375502 (completed in 2001, including soil ECM RM

- 30D

- 2) 48131402 (Ontario, Canada. Completed in 2007, including soil ECM RM

30S

- 1

- 1) 48131403 (Nova Scotia, Canada. Completed in 2007, including soil ECM RM

- 30S

- 1) 48131404 (WA. Completed in 2 007, including soil ECM RM

- 30S

- 1) (No ILVs for soil ECMs RM

- 30D

- 2 , RM

- 30S

- 1, and ECM RM

- 30S

- 1

- 1 were submitted) Supplemental Supplemental Supplemental Supplemental Supplemental

In review Supplemental

In review

In review

In review No 1

835.6200 Aquatic Field

Dissipation (ECM/ILV) 47550605 (conducted in IA

and FL, included water/sediment ECM GPL

MTH

- 064) 47550603 (ILV for water and sediment ECM GPL

MTH

- 064) Supplemental

Supplemental Yes

850.1730 Accumulation in Fish/ Bioconcentrat ion Waived 47550604 2 Waived

- Yes

1 The registrant must submit: (1) the ILV for the soil method (RM

- 30S

- 1) used in 48131403 and 48131404 for the analysis of flumioxazin; (2) the ILV for the modified soil method (RM

- 30S

- 1

- 1) used in MRID 48131402 for the an alyses of flumioxazin, THPA, and HPA ; and (3) two TFD studies conducted in Illinois and California that the Agency identified them as data gaps in the 2005 ecological risk assessment (according to Bob Hamilton with Valent on 2/14/11, the registrant does ha ve these two studies and they had submitted these two studies to Canada)

. 2 MRID 47550604 (2008) is a study related to the magnitude of residues of flumioxazin in fish. It was reviewed by W. Cutchin in ARIA/RD/OPP).

### Page | 47 2. Effects

For the ecological asse ssment, Table 9 lists the status of ecological data requirements for flu mioxazin . The following is a summary of identified data gaps and associated uncertainties: 850.1010 Freshwater Invertebrate Acute LC 50 

### : A study was submitted that examined the toxi c effects of flumioxazin on freshwater invertebrates. However, the study showed high levels of precipitate in the solutions. These precipitates likely confounded the effects of the chemical itself. A new study is needed to address the uncertainty relate d to an accurate assessment of the toxicity of flumioxazin to freshwater free

- swimming invertebrates. 850.1400 Freshwater Fish Early Life - Stage: An additional study needs to address the potential uV light

- enhanced toxicity for freshwater fish based on th e LDPH nature of flumioxazin . A study related to this enhanced toxicity is expected to be submitted by the technical registrant by June 30 of 2011. 850.1400 Estuarine/Marine Fish Early Life - Stage: Effects were identified to freshwater fish in the early life

- stage test, with a LOAEC of 16 ppb. Considering that the previous risk assessment (D357187) for aquatic uses identified the 60 day average EEC to be 25 ppb, there is uncertainty as to whether estuarine/marine fish would be as sensitive to this concen tration as freshwater species. In addition, the CFR 40 part 158 guidelines state that this test on estuarine/marine fish is conditionally required if “the estimated environmental concentration (EEC ) in water is ≥ 0.01 of the acute EC 50 

### or LC 50 

### or if any of the following conditions exist...”. The 60 day average flumioxazin parent concentrat ion is 25 ppb, which is less tha n 0.01 of the acute LC 50 

### of > 4.7 ppm ( 0.01 * 4.7 ppm = 47ppb) . However, the 60 day average concentration for the degradate APF is 110 ppb as stated in the previous risk assessment. No data has been submitted regarding the toxicity of any of the degradates. Without this data, the degradates are assumed to be as toxic as the parent c ompound, and therefore the above condition is met. An early life

- stage study that addresses the toxicity of flumioxazin to estuarine/marine fish is needed for the risk assessment. Considering that flumioxazin is an LDPH and may have enhanced toxicity und er elevated light conditions, the results of the freshwater fish early life

- stage test that addresses light

- enhanced toxicity may be applied to the results of this study as appropriate. 850.1500 Fish Full Life - Cycle: According to the CFR 40 part 158 guid elines, this study is conditionally required when “the end

- use product is intended to be applied directly to water, or is expected to be transported to water from the intended use site, and when any of the following conditions apply:

 If the estimated envir onmental concentration (EEC) is ≥ 0.1 of the no

observed

- effect level in the fish early

- life stage or invertebrate life cycle test;
 If studies of other organisms indicate that the reproductive physiology of fish may be affected.” Flumioxazin has aquatic us es that indicate the chemical will be applied directly to freshwater systems, which meets the first part of the criteria. The peak EEC for parent flumioxazin based on the previous aquatic risk assessment (D357187) is 400 ppb. The NOAEC in the fish early life

- stage is 7.7 ppb and in the invertebrate life

- cycle is 28 ppb. Therefore, 0.1 of the peak EEC (0.1*400 ppb = 40 ppb) is greater than both of these no effect levels, and therefore the second condition is also met. Furthermore, reproductive effects we re observed

### Page | 48

in the freshwater invertebrate life

- cycle test. A study on the fish full life

- cycle is needed to address this remaining uncertainty of chronic risk to fish. 850.2100 Avian Oral LD 50 

### : CFR 40 part 158 guideline s require data on one passerine species and either a waterfowl or upland game bird species. Data has only been submitted for the Bobwhite quail. There is uncertainty as to the sensitivity of passerine species compared to other bird species. However, no mortality in any treatment group was reported in both the acute oral and dietary toxicity studies for avian species. Avian species do not appear to be sensitive to flumioxazin on an acute basis.

Table 9 . Ecological effects dat a requirements for f lumioxazin and remaining data gaps.

Guideline # Data Requirement Test Substance MRID # or Citation Study

Classification Are

additional data needed for ecological risk assessment?
850.2100 Avian Oral LD 50 TGAI 42684945 (Bobwhite q uail) Acceptable No
850.2200 Avian Dietary LC 50 TGAI TGAI 42684946

42684947 Acceptable No
850.2300 Avian Reproduction TGAI TGAI 44295005

44295006 Acceptable

Supplemental No
850.1075 Freshwater Fish LC 50 TGAI TGAI 42684948

42684949 44295007 Acceptable

Acceptable Supplemental No

850.1010 Freshwater Invertebrate

Acute LC 50 TGAI 42684950 Supplemental Yes

850.1075 Estuarine/Marine Fish LC 50 TGAI 44295010 Acceptable No

850.1025 Estuarine/Marine Mollusk EC 50 TGAI 44295008 Acceptable No 850.1035 850.1045 850.1055 850.1075 Estuarine/Marine Shrimp EC 50 TGAI 44295009 Acceptable No

850.1400 Freshwater Fish Early

Life

- Stage TGAI 44295012 Acceptable Yes

850.1400 Estuarine/Marine Fish

Early Life

- Stage No data submitted Yes

850.1300 Aquatic Invertebrate Life

C ycle (freshwater) TGAI 44295011 Acceptable No

### Page | 49

Guideline # Data Requirement Test Substance MRID # or Citation Study

Classification Are

additional data needed for ecological risk assessment?
850.1350 Aquatic Invertebrate Life

Cycle (marine) TGAI 44295013 Acceptable No

850.1500 Fish Full Life

- Cycle No data submitted Yes

850.4225 Seedling Emergence (Tier II) TEP 44295029 Acceptable No

850.425 0 Vegetative Vigor

(Tier II) TEP 44295030 Acceptable No

850.4400 850.5400 Aquatic Plant Growth

(Tier II) TGAI 44295031 44295032 44295033 44295034 44295035 Acceptable No

850.3020 Honey Bee Acute

Contact LD 50 TGAI 42684951 Acceptable No

870.1100 Acute Oral Toxicity to Rat TGAI 42684911 42684912 Acceptable No

870.3800 2

- Generation Mammalian

Reproduction TGAI 42684934 42684935 42684936 Acceptable No

Non

- guideline Predatory Mite TEP 47889334 In Review N/A
Non

- guideline Parasitic Wasp TEP 47889335 In Rev iew N/A


## VIII. References 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. CALDPR. 2010. California Department of Pesticide Regulation Usage Data. Accessed July 14, 2010. Fletcher, J.S., J.E. Nellessen, and T.G. Pfleeger. 1994. Literature review and evaluation of the EPA food

- chain (Kenaga) nom ogram, 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 E nvironment. In F. Coulston and F. Korte, eds., Environmental Quality and Safety: Chemistry, Toxicology, and Technology, Georg Thieme Publ., Stuttgart, West

### Page | 50 Germany, pp. 9

- 28. Matringe, M., J.M. Camadro, P Labbe, and R Scalla. 1989. Protoporphyrinogen ox idase as a molecular target for diphenyl ether herbicides. Biochem. J. 260: 231

- 235. Teske, M.E., and T.B. Curbishley. 2003. AGDISP Version 8.07 User Manual . Prepared For United States Department of Agriculture Forest Service. C.D.I. Technical Note No. 02

- 06. June 2003. USEPA. 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 USEPA. 2002. Guidance for Selecting Input Parameters in Modeling the Environmental Fate and Transport of Pesticides. U.S. Environmental Protection Agency, Office of Prevention, Pesticides a nd Toxic Substances, Office of Pesticide Programs, Environmental Fate and Effects Division. Feb. 28, 2002. Online at: http://www.epa.gov/oppefed1/models/water/input_guidance2_28_02.htm. USEPA . 2004

. Overview of the Ecological Risk Assessment Process i n 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. USEPA. 2007a. Ecotoxicology (ECOTOX) database. Version 4. Office of Research and Development (ORD) , and the National Health and Environmental Effects Research Laboratory's (NHEERL's) Mid

- Continent Ecology Division (MED)

. http://cfpub.epa.gov/ecotox/ecotox_home.cfm USEPA . 2007b. Ecological Incident Information System (EIIS). Environmental Fate and Effects Division. USEPA . 2010 Scree ning Level Estimates of Agricultural Uses on Flu mioxazin . Biological and Economic Assessment Division, Office of Pesticide Programs. Dated July 15, 2010. U.S. Fish and Wildlife Service (USFWS) and National Marine Fisheries Service (NMFS). 1998. Endang ered Species Consultation Handbook: Procedures for Conducting Consultation and Conference Activities Under Section 7 of the Endangered Species Act. Final Draft. March 1998. USGS. 2011. National water quality assessment program. Accessed January 15 th , 2011. http://water.usgs.gov/nawqa/

.


### SUBMITTED FATE STUDIES: 42684905 Katagi, T.; Takahashi, N.; Nambu, K.; et al. (1990) Hydrolysis of THP

- (carbon 14)

- S

- 53482 in Buffered Aqueous Solutions: Lab Project Number: HYD89005. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 68 p. 42697501 Katagi, T.; Takahashi, N.; Nambu, K.; et al. (1990) Hydrolysis of Ph

- (carbon 14)

- S

- 53482 in Buffered Aqueous Solutions: Lab Project Number: HYD89001. Unpublished study prep ared by Sumitomo Chemical Co., Ltd. Biochemistry and Toxicology Lab. 71 p. 44295036 Fathulla, R. (1995) Artificial Sunlight Photodegradation of (Phe

- (carbon 14)

- S

- 53482 in a Buffered Aqueous Solution: Lab Project Number: HLA 6311

- 112: 9600435. Unpublished study prepared by Hazleton Labs America, Inc. 112 p. 44295037 Fathulla, R. (1995) Artificial Sunlight Photodegradation of (THP

- (carbon 14))

- S

- 53482 in a Buffered Aqueous Solution: Lab Project Number: HLA 6311

- 110. Unpublished study prepared by Hazleton Lab s America, Inc. 90 p. 45914601 Rose, A.; Jalal, M. (2003) Photodegradation of (Carbon 14) Flumioxazin in Buffer: Lab Project Number:

### Page | 51 VP

- 25443. Unpublished study prepared by Valent Technical Center. 171 p. 44295038 Fathulla, R. (1993) Artificial Sunlight Ph otodegradation of (Phe

- (carbon 14))

- S

- 53482 on Soil: Lab Project Number: HWI 6311

- 106: 9300318. Unpublished study prepared by Hazleton Wisconsin, Inc. 149 p. 44295039 Fathulla, R. (1993) Artificial Sunlight Photodegradation of (THP

- (carbon 14))

- S

- 53482 on Soil: Lab Project Number: HWI 6311

- 158: 9500359: SBM

- 31

- 0035. Unpublished study prepared by Hazleton Wisconsin, Inc. 123 p. 42684906 Fathulla, R. (1991) Aerobic Soil Metabolism of (carbon 14)

- S

- 53482: Lab Project Number: HLA 6311

- 104. Unpublished study pre pared by Hazleton Laboratories America, Inc. 108 p. 42884009 Fathulla, R. (1993) Aerobic Soil metabolism of (THP

-- (carbon 14))

-- S

- 53482: Lab Project Number: 6311

- 156. Unpublished study prepared by Hazleton Wisconsin, Inc. 103 p. 44295040 Pensyl, J. (1996) Half

- Life of Flumioxazin in Four Soils Under Laboratory Conditions: Lab Project Number: VP

- 11579: 9600451: V

- 96

- 11579. Unpublished study prepared by Valent USA Corp. 137 p. 44295041 Archer, G.; Korsch, B. (1996) An Anaerobic Aquatic Soil Metabolism Study w ith (carbon 14)S

- 53482 (Flumioxazin): Lab Project Number: 5680

- 93

- 0099

- EF

- 001: 9700061: 5680

- 93

- 0099

- EF

- 000. Unpublished study prepared by Ricerca, Inc. 235 p. 45914602 Assaf, N. (2003) Anaerobic Aquatic Metabolism of (PH

- (Carbon 14)) Flumioxazin and (THP

- (Carbon 14)) Flumioxazin: Lab Project Number: VP

- 23940: V

- 01

- 23940. Unpublished study prepared by Valent Technical Center. 210 p. 47761801 Ridge, M. (1998) (Carbon 14)

- Flumioxazin: Degradation and Retention in Water

- Sediment Systems. Project Number: 1531/9 , 200700002. Unpublished study prepared by Covance Laboratories, Ltd. 136 p. 42684907 Fathulla, R. (1992) Column Leaching Characteristics of (Phe

- (carbon 14))

- V

- 53482 in Typical Agricultural Soils (Unaged Study): Lab Project Number: HLA 6320

- 102. Unpublis hed study prepared by Hazleton Laboratories America, Inc. 85 p. 42684908 Fathulla, R. (1992) Column Leaching Characteristics of (THP

- (carbon 14))

- V

- 53482 in Typical Agricultural Soils (Unaged Soils): Lab Project Number: HLA 6320

- 104. Unpublished study pre pared by Hazleton Laboratories America, Inc. 90 p. 42684909 Fathulla, R. (1992) Column Leaching Characteristics of ?Phe

- (carbon 14)|

- V

- 53482 in Typical Agricultural Soils (Aged Soils): Lab Project Number: HWI 6320

- 108. Unpublished study prepared by Hazleto n Laboratories America, Inc. 115 p. 42884010 Fathulla, R. (1993) Column Leaching Characteristics of (Phe

-- (carbon 14))

-- V

- 53482 in Soil (Part 2): Lab Project Number: 6320

- 110. Unpublished study prepared by Hazleton Wisconsin, Inc. 113 p. 45309201 Rose, K.; Shah, J.; Korsch, B. (1994) Adsorption and Desorption of (Phenyl

- (carbon

- 14))

- APF to Soil: Lab Project Number: 5855

- 93

- EF

- 001: 200000407. Unpublished study prepared by Ricerca, Inc. 157 p. 45309202 Shah, J. (1994) Adsorption and Desorption of Tetrahydroph thalic Acid (THPA) to Soil: Lab Project Number: 5854

- 93

- 0252

- EF

- 001: 200000406. Unpublished study prepared by Ricerca, Inc. 153 p. 44295043 Corbin, B. (1996) Soil Dissipation of Phenyl

- (carbon 14)

- Flumioxazin Under Field Conditions in North Carolina: Lab P roject Number: 10728: 767: 5661

- 93

- 0136

- EF

- 001. Unpublished study prepared by PTRL East, Inc. and Ricerca, Inc. 326 p. 44295044 Pensyl, J. (1996) Terrestrial Field Dissipation Study with V

- 53482 WP Herbicide on No

- Till Ground in Illinois: Lab Project Numbe r: VP

- 11278: 9600489: V

- 95

- 11278. Unpublished study prepared by Valent USA Corp. 267 p. 44295045 Pensyl, J. (1996) Field Dissipation Study with V

- 53482 WDG Herbicide in Mississippi: Lab Project Number: VP

- 1013: 9600493: 1641

- 91

- 1013. Unpublished study prep ared by Valent USA Corp. 327 p. 44295046 Pensyl, J. (1996) Field Dissipation Study with V

- 53482 WDG Herbicide in Iowa: Lab Project Number: VP

- 1011: 9600490: 1641

- 91

- 1011. Unpublished study prepared by Valent USA Corp. 464 p. 44295047 Lightle, S.; Coody, P. (1997) Soil Dissipation of (Phenyl

- (carbon 14))Flumioxazin Under Actual Field Conditions in Soybeans in Indiana: (Final Report): Lab Project Number: 964: 1926: 9700264. Unpublished study prepared by PTRL East, Inc.; PTRL West, Inc.; and A&L Great Lakes La bs, Inc. 257 p. 45375502 Schreier, T. (2001) Terrestrial Field Soil Dissipation of Fluminoxazin in Established Walnuts: Lab Project Number: 20335: 200100002: V

- 99

- 20335. Unpublished study prepared by Valent U.S.A. Corporation. 190 p. 48131402 Green, C. (20 07) Terrestrial Field Soil Dissipation of Flumioxazin (Chateau WDG) on Bare Ground in Ontario, Canada. Project Number: V/26286. Unpublished study prepared by Valent Dublin Laboratory. 365 p.

### Page | 52

46163701 Pensyl, J. (2003) Rebuttal to the EPA Data Evaluation Re port for Soil Dissipation Studies Follow Up Report. Project Number: FLUM/DER/01. Unpublished study prepared by Valent U.S.A. Corporation. 23 p. 47550605 Flora, E.A., M.T. Boatwright and S. Selim (2008) Aquatic Dissipation of Flumioxazin in Iowa during 2007 , Valent Project Number VP

- 32001. Unpublished Study Performed by Eurofins

- Agrisearch Americas Inc., Noblesville, Indiana (test facility), University of Northern Iowa, Cedar Falls, Iowa (field phase), Research Options, Inc., Montezuma, Georgia (field phase) , Agvise Labs, Inc., Northwood, North Dakota (soil characterization) and Golden Pacific Laboratories, LLC, Fresno, California (analytical phase) and Sponsored and Submitted by Valent U.S.A. Corporation, Walnut Creek, California (pp.1,5, and 6), Laboratory Project ID:VP

- 32001. Experiment initiation August 8,2007 (test application, Site 1, p.13) and Completion November 20, 2007 (analytical phase, Appendix 3, p.115). Final Report Issued July 2, 2008. 42684910 Wustner, D. (1993) Bioaccumulation in Fish of V

- 534 82 (Waiver Request 165

- 4): Lab Project Number: W

- 482

- 2. Unpublished study prepared by Valent USA Corp. 9 p. 45375508 Hewitt, A. (2000) Atomization Droplet Size Spectra for Cotton/Soybean Herbicides: Lab Project Number: V00

- 002: 200100035. Unpublished study prepared by Stewart Agricultural Research Services, Inc. 96 p. 42884001 Gustafson, D. (1993) EEC's for Flumioxazin, Predicted in Pond Water Using the PRZM and EXAMS Computer Models: Lab Project Number: 93

- 482

- 02. Unpublished study prepared by Valent USA C orp. 16 p. 42985501 Gustafson, D. (1993) EEC's for Flumioxazin in Pond Water Using PRZM and EXAMS Computer Models: Amended Report No. 1 (MRID 42884001): Lab Project Number: 93

- 482

- 02A. Unpublished study prepared by Valent U.S.A. Corp. 16 p. 44295042 Krupla k, J. (1995) Independent Laboratory Validation of the Method for Quantitation of Flumioxazin in Soil: Lab Project Number: 1550

- 1: 9600111: RM

- 30D. Unpublished study prepared by Analytical Development Corp. 67 p. 45375512 Rose, A. (2001) Henry's Law Constan t for Flumioxazin: Lab Project Number: VP

- 23237: 200100079. Unpublished study prepared by Valent U.S.A. Corporation. 8 p. 47550601 Habig, C (2008) Estimated Drinking Water Concentrations for the Proposed Aquatic Uses of the Herbicide Flumioxazin. Project N umber: FLUMIOXAZIN/08/01. Unpublished study prepared by Exponent, Inc. 15 p. 48131403 Kowalsky, J. (2007) NAFTA Guidance Document for Conducting Terrestrial Field Dissipation Studies April 20, 2005. Project Number: V/29153, 200700278. Unpublished study pre pared by Valent Dublin Laboratory. 324 p. 48131404 Kowalsky, J. (2007) NAFTA Guidance Document for Conducting Terrestrial Field Dissipation Studies April 20, 2005. Project Number: 200700277, V/29031. Unpublished study prepared by Valent Dublin Laboratory. 290 p. 47550603 Claussen, F. (2008) Independent laboratory validation of method GPL

- MTH

- 064 for the determination of flumioxazin and its APF and 482,

- HA metabolites in pond water and pond sediment. Unpublished study performed by EPL Bio

- Analytical Services (EPL

- BAS), Niantic, Illinois; sponsored and submitted by Valent U.S.A. Corporation, Walnut Creek, California (p. 45). Laboratory Project No.: 1596410. Experiment initiated December 11,2007 and completed June 27,2008 (p. 10). Final report issued June 27,20 08. 47550604 Aufderheide, J. (2008) Magnitude of Residue of Flumioxazin in Fish. Project Number: 63381, VP/32363, 080281. Unpublished study prepared by ABC Laboratories, Inc. and Golden Pacific Laboratories, LLC (GPL). 220 p. (This study was reviewed by W . Cutchin in ARIA/RD/OPP) 

### SUBMITTED EFFECTS STUDIES: 42684945 Lloyd, D.; Jaber, M.; Hoxter, K. (1990) An Acute Oral Toxicity Study with the Bobwhite: V

- 53482: Final Report: Lab Project Number: 263

- 111. Unpublished study prepared by Wildlife International Ltd. 21 p. 42684946 Culotta, J.; Hoxter, K.; Smith, G.; et al. (1991) V

- 53482: A Dietary LC50 Study with the Mallard: Lab Project Number: 263

- 110. Unpublished study prepared by Wildlife International Ltd. 37 p. 42684947 Culotta, J.; Hoxter, K.; Smith, G.; et al. (1991) V

- 53482: A Dietary LC50 Study with the Northern Bobwhite: Lab Project Number: 263

- 109. Unpublished study prepared by Wildlife International Ltd. 37 p.

### Page | 53

44295005 Beavers, J.; Simpler, O.; Smith, G.; et al. (1994) V

- 53482: A One

- Generation Rep roduction Study with the Mallard (Anas platyrhynchos): (Final Report): Lab Project Number: 263

- 122: 9600102: 263

- 119. Unpublished study prepared by Wildlife International Ltd. 241 p. 44295006Beavers, J.; Simpler, O.; Smith, G.; et al. (1994) V

- 53482: A One

- generation Reproduction Study with the Bobwhite (Colinus virginianus): (Final Report): Lab Project Number: 263

- 121: 9600101: 263

- 118. Unpublished study prepared by Wildlife International Ltd. 240 p. 42684948 Takinoto, Y.; Hagino, S.; Saito, S. (1989) The Acute Toxicity of S

- 53482 to Rainbow Trout (Salmo gairdneri): Lab Project Number: FTX

- 89003. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 30 p. 42684949 Takimoto, Y.; Hagino, S.; Saito, S. (1989) The Acute Toxicity of S

- 53482 to Bluegill (Lep omis Macrochirus): Lab Project Number: FTX

- 89006. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 30 p. 44295007 Sword, M.; Thompson, K.; Veltri, J. (1992) Toxicity of S

- 53482 T.G. to Rainbow Trout (Oncorhynchus mykiss) After 21 Days of Exposure Under Flow

- Through Conditions: Final Report: Lab Project Number: 40319: 9300510. Unpublished study prepared by ABC Labs, Inc. 564 p. 42684950 Reed, D.; Swigert, J. (1992) A 48

- Hour Flow

- Through Acute Toxicity Test with the Cladoceran (Daphnia magna): V

- 534 82: Lab Project Number: 263A

- 104. Unpublished study prepared by Wildlife International Ltd. 48 p. 43066501 Radcliffe, M.; Solomon, B. (1992) A 48

- Hour Flow

- through Acute Toxicity Test with the Cladoceran (Daphnia magna) (of V

- 53482), Response to EPA Review : Lab Project Number: 93

- 482

- 06: 263A

- 104. Unpublished study prepared by Valent U.S.A. Corp. 48 p. 44295008 Dionne, E. (1994) V

- 53482 Technical

-- Acute Toxicity to Eastern Oyster (Crassostrea virginica) Under Flow

- Through Conditions: Lab Project Number: 127 09.0693.6128.504: VP

- 10712: 9400826. Unpublished study prepared by Springborn Labs, Inc. 81 p. {OPPTS 850.1025} 44295009 Machado, M. (1994) V

- 53482 Technical

-- Acute Toxicity to Mysid Shrimp (Mysidopsis bahia) Under Flow

- Through Conditions: Lab Project Numb er: VP

- 10710: 12709.0693.6126.515: 9400825. Unpublished study prepared by Springborn Labs, Inc. 77 p. {OPPTS 850.1035} 44295010 Machado, M. (1994) V

- 53482 Technical

-- Acute Toxicity to Sheepshead Minnow (Cyprinodon variegatus) Under Flow

- Through Conditions: Lab Project Number: 12709.0693.6127.505: VP

- 10713: 9400827. Unpublished study prepared by Springborn Labs, Inc. 75 p. {OPPTS 850.1075} 44295011 Drottar, K.; Swigert, J. (1994) (Carbon 14)

- S

- 53482: A Flow

- Through Life

- Cycle Toxicity Test with the Cladocera n (Daphnia magna): (Final Report): Lab Project Number: 166A

- 108: 9400163. Unpublished study prepared by Wildlife International Ltd. 57 p. {OPPTS 850.1300} 44295012 Hagino, S.; Miyamoto, M. (1996) Early Life

- Stage Toxicity Test of S

- 53482 with Rainbow Trout (Oncorhynchus mykiss): (Final Report): Lab Project Number: ELS950001: 9600537: 9600538. Unpublished study prepared by Sumitomo Chemical Co., Ltd. 858 p. {OPPTS 850.1400} 44295013 Sousa, J. (1996) V

- 53482 TGAI (Flumioxazin)

-- The Chronic Toxicity to Mysids (Mysidopsis bahia) Under Flow

- Through Conditions: Lab Project Number: 96

- 9

- 6686: 9600462. Unpublished study prepared by Springborn Labs, Inc. 101 p. {OPPTS 850.1350} 42922901 Radcliffe, M. (1993) Letter Sent to Joanne Miller dated Sep. 3, 1993 providing pr eliminary information from a rainbow trout early life

- stage preliminary study being conducted with flumioxazin. Prepared by Valent USA Corp. 5 p. 44295031 Hoberg, J. (1996) V

- 53482 (Flumioxazin

-- Toxicity to the Freshwater Green Alga (Selenastrum capricornu tum): Lab Project Number: 96

- 9

- 6690: 9600536: 061196/FIFRA/430/V

- 53482. Unpublished study prepared by Springborn Labs, Inc. 79 p. {OPPTS 850.4400} 44295032 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- Toxicity to the Freshwater Diatom (Navicula pelliculosa): L ab Project Number: 96

- 10

- 6717: 9600525: 061196/FIFRA/440/V

- 53482. Unpublished study prepared by Springborn Labs, Inc. 83 p. {OPPTS 850.4400) 44295033 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- Toxicity to the Marine Diatom (Skeletonema costatum): Lab Project Number: 96

- 10

- 6703: 9600534: 061196/FIFRA/450/V

- 53482. Unpublished study prepared by Springborn Labs, Inc. 79 p. {OPPTS 850.440} 44295034 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- 5

- Day Toxicity to the Freshwater Blue

- Green Alga (Anabaena flos

- aquae): Lab Project Number: 96

- 10

- 6704: 9600533: 061196/FIFRA/420/V

- 53482. Unpublished study prepared by Springborn Labs, Inc. 79 p. {OPPTS 850.4400}

### Page | 54

44295035 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- Toxicity to the Duckweed (Lemna gibba): Lab Project Number: 96

- 10

- 67 22: 9600532: 061196/FIFRA/410/V

- 53482. Unpublished study prepared by Springborn Labs, Inc. 84 p. {OPPTS 850.4400} 44295029 Chetram, R. (1997) Tier II Seedling Emergence Nontarget Phytotoxicity Study Using Flumioxazin: (Final Report): Lab Project Number: 96 569: 9700256: VP

- 11430. Unpublished study prepared by ABC Labs California. 276 p. {OPPTS 850.4225} 44295030 Chetram, R. (1997) Tier II Vegetative Vigor Nontarget Phytotoxicity Study Using Flumioxazin: Lab Project Number: 96570: 94700257: VP

- 11559. Unpublis hed study prepared by ABC Labs California. 395 p. {OPPTS 850.4250} 44295031 Hoberg, J. (1996) V

- 53482 (Flumioxazin

-- Toxicity to the Freshwater Green Alga (Selenastrum capricornutum): Lab Project Number: 96

- 9

- 6690: 9600536: 061196/FIFRA/430/V

- 53482. Unpubli shed study prepared by Springborn Labs, Inc. 79 p. {OPPTS 850.4400} 44295032 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- Toxicity to the Freshwater Diatom (Navicula pelliculosa): Lab Project Number: 96

- 10

- 6717: 9600525: 061196/FIFRA/440/V

- 53482. Unpublished s tudy prepared by Springborn Labs, Inc. 83 p. {OPPTS 850.4400) 44295033 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- Toxicity to the Marine Diatom (Skeletonema costatum): Lab Project Number: 96

- 10

- 6703: 9600534: 061196/FIFRA/450/V

- 53482. Unpublished study prepa red by Springborn Labs, Inc. 79 p. {OPPTS 850.440} 44295034 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- 5

- Day Toxicity to the Freshwater Blue

- Green Alga (Anabaena flos

- aquae): Lab Project Number: 96

- 10

- 6704: 9600533: 061196/FIFRA/420/V

- 53482. Unpublished stud y prepared by Springborn Labs, Inc. 79 p. {OPPTS 850.4400} 44295035 Hoberg, J. (1996) V

- 53482 (Flumioxazin)

-- Toxicity to the Duckweed (Lemna gibba): Lab Project Number: 96

- 10

- 6722: 9600532: 061196/FIFRA/410/V

- 53482. Unpublished study prepared by Springborn Labs, Inc. 84 p. {OPPTS 850.4400} 42684951 Hoxter, K.; Thompson, M.; Jaber, M. (1990) An Acute Contact Toxicity Study with the Honey Bee: V

53482: Lab Project Number: 263

- 112. Unpublished study prepared by Wildlife International Ltd. 14 p. 44295014 Willia ms, W.; Pugsley, R.; Johnson, L. (1996) Probabilistic Modeling of Flumioxazin Exposure to Aquatic Nontarget Organisms Associated with Flumioxazin (V

- 53482) Use on Soybeans and Peanuts: (Final Report): Lab Project Number: WEI 825.06: 9700146. Unpublished st udy prepared by Waterborne Environmental Inc. 52 p. 47889334 Taylor, K. (2009) V

- 10233: Acute Toxicity to Typhlodromus pyri in the Laboratory: Final Report. Project Number: MCW0003. Unpublished study prepared by Huntingdon Life Sciences, Ltd. 38 p. 4788933 5 Taylor, K. (2009) V

- 10233: Acute Toxicity to Aphidius rhopalosiphi in the Laboratory: Final Report. Project Number: MCW0002. Unpublished study prepared by Huntingdon Life Sciences, Ltd. 39 p.

### Page | 55



## Appendix 1 . ECOTOX Accepted and Rejected Papers Accepted Pa pers: Daugrois, J. H., Hoy, J. W., and Griffin, J. L. (2005). Protoporphyrinogen Oxidase Inhibitor Herbicide Effects on Pythium Root Rot of Sugarcane, Pythium Species, and the Soil Microbial Community. Phytopathology 95: 220

- 226. EcoReference No.: 107864 Geoffroy, L., Frankart, C., and Eullaffroy, P. (2004). Comparison of Different Physiological Parameter Responses in Lemna minor and Scenedesmus obliquus Exposed to Herbicide Flumioxazin. Environ.Pollut. 131: 233

- 241. EcoReference No.: 119333 Kawamura, S ., Kato, T., Matsuo, M., Sasaki, M., Katsuda, Y., Hoberman, A. M., and Yasuda, M. (1995). Species Difference in Developmental Toxicity of an N

- Phenylimide Herbicide Between Rats and Rabbits and Sensitive Period of the Toxicity to Rat Embryos. Congenital A nom. 35: 123

- 132. EcoReference No.: 119367 Kawamura, S., Yoshioka, T., Kato, T., Matsuo, M., and Yasuda, M. (1996). Histological Changes in Rat Embryonic Blood Cells as a Possible Mechanism for Ventricular Septal Defects Produced by an N

- Phenylimide Herbic ide. Teratology 54: 237

- 244. EcoReference No.: 119661 Mudge, C. R. (2007). Characterization of Flumioxazin as an Aquatic Herbicide. M.S.Thesis, Univ.of Florida 121 p. (UMI# 3300773). EcoReference No.: 118705 Partridge, D. E., Sutton, T. B., and Jordan, D. L. (2006). Effect of Environmental Factors and Pesticides on Mycoparasitism of Sclerotinia minor by Coniothyrium minitans. Plant Dis. 90: 1407

- 1412. EcoReference No.: 119499 Richardson, R. J., Roten, R. L., West, A. M., True, S. L., and Gardner, A. P . (2008). Response of Selected Aquatic Invasive Weeds to Flumioxazin and Carfentrazone

- Ethyl. J.Aquat.Plant Manag. 46: 154

- 158. 

### Rejected Papers: Acceptable to EcoTox but not to OPP Johnson III, W. C., Prostko, E. P., and Mullinix, B. G. Jr. (2005). Impro ving the Management of Dicot Weeds in Peanut with Narrow Row Spacings and Residual Herbicides. Agron.J. 97: 85

- 88. EcoReference No.: 82184 Niekamp, J. W., Johnson, W. G., and Smeda, R. J. (1999). Broadleaf Weed Control with Sulfentrazone and Flumioxazin i n No

- Tillage Soybean (Glycine max). Weed Technol. 13: 233

- 238. EcoReference No.: 72819 Patzoldt, W. L., Tranel, P. J., and Hager, A. G. (2005). A Waterhemp (Amaranthus tuberculatus) Biotype with Multiple Resistance Across Three Herbicide Sites of Action. Weed Sci. 53: 30

- 36. EcoReference No.: 108756 Wilcut, J. W., Askew, S. D., Bailey, W. A., Spears, J. F., and Isleib, T. G. (2001). Virginia Market

- Type Peanut (Arachis hypogaea) Cultivar Tolerance and Yield Response to Flumioxazin Preemergence. Weed Tech nol. 15: 137

- 140. EcoReference No.: 66740 Excluded 2007

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- 61413. Chem Codes : Chemical of Concern: FMX Code : FOOD. 2008

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- ). Tackling tobacco in poorer countries. The New Scientist 199: 6. Chem Codes : Chemical of Concern: FMX Code : HUMAN HEALTH. 2002

- ). UK pledge for funding boost. Current Biology 12: R510. Chem Codes : Chemical of Concern: FMX Code : NO TOX DATA.

### Page | 56

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## Appendix 2 . The Risk Quotient Method and Levels of Concern The Risk Quotient Method is the means used by EFED to integrate the results of exposure and ecotoxicity data. For this method, Risk Quotients (RQs) are cal culated by dividing exposure estimates by the acute and chronic ecotoxicity values (i.e., RQ = EXPOSURE /TOXICITY). These RQs are then compared to OPP's levels of concern (LOCs). These LOCs are criteria used by OPP to indicate potential risk to non

- target organisms and the need to consider regulatory action. EFED has defined LOCs for acute risk, potential re stricted use classification, and for endangered species. The criteria indicate that a pesticide used as directed has the potential to cause adverse effects on non - target organisms. LOCs currently address the following risk presumption categories: (1) acu te

- there is a potential for acute risk; regulatory action may be warranted in addition to restricted use classification; (2) acute restricted use

- the potential for acute risk is high, but this may be mitigated through restricted use classification; (3) acute endangered species

- the potential for acute risk to endangered species is high, regulatory action may be warranted; and (4) chronic risk

- the potential for chronic risk is high, regulatory action may be warranted. Currently, EFED does not perform assessments for chronic risk to plants, acute or chronic risks to non

- target insects, or chronic risk from granular/bait formulations to mammalian or avian species. The ecotoxicity test values (i.e., measurement endpoints) used in the acute and ch ronic RQs are derived from required studies. Examples of ecotoxicity values derived from short

- term laboratory studies that assess acute effects are: (1) LC50 (fish and birds), (2) LD50 (birds and mammals), (3) EC50 (aquatic plants and aquatic invertebrate s), and (4) EC25 (terrestrial plants). Examples of toxicity test effect levels derived from the results of long

- term laboratory studies that assess chronic effects are: (1) the Lowest Observed Adverse Effect Concentration (LOAEC) (birds, fish, and aquatic invertebrates), and (2) the No Observed Adverse Effect Concentration (NOAEC) (birds, fish and aquatic invertebrates). The NOAEC is generally used as the ecotoxicity test value in assessing chronic effects. Risk presumptions, along with the corresponding RQ s and LOCs are summarized in Table B1.

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Table B1. Agency risk quotient (RQ) metrics and levels of concern (LOC) per risk class. Risk Class Risk Description RQ LOC Aquatic Animals (fish and invertebrates) Acute Potential for effects to non

- listed animals from acute

exposures Peak EEC/LC 50 1 0.5
Acute Restricted Use Potential for effects to animals from acute exposures

Risks may be mitigated through restricted use classification Peak EEC/LC 50 1 0.1

Acute Listed Species Listed species may be potenti ally affected by acute

exposures Peak EEC/LC 50 1 0.05
Chronic Potential for effects to non

- listed and listed animals

from chronic exposures 60

- day EEC/NOEC (fish) 1 21

- day EEC/NOEC (invertebrates) Terrestrial Animals (mammals and birds) Acute Potent ial for effects to non

- listed animals from acute

exposures EEC 2 /LC 50 (Dietary) 0.5 EEC/LD 50 (Dose)
Acute Restricted Use Potential for effects to animals from acute exposures

Risks may be mitigated through restricted use classification EEC 2 /LC 50 (Dieta ry) 0.2 EEC/LD 50 (Dose)
Acute Listed Species Listed species may be potentially affected by acute

exposures EEC 2 /LC 50 (Dietary) 0.1 EEC/LD 50 (Dose) Chronic Potential for effects to non

- listed and listed animals

from chronic exposures EEC 2 /NOAEC 1
Plants Non

- Listed Potential for effects to non

- target, non

- listed plants

from exposures EEC/ EC 25 1
Listed Plant Potential for effects to non

- target, listed plants from

exposures EEC/ NOEC 1 EEC/ EC 05
1 LC 50 or EC 50 . 2 Based on upper bound Kenag a values.

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## Appendix 3 . Results from the Screening Imbibition Program

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## Appendix 4 . Results from the Screening Tool for Inhalation Risk