### 1 OFFICE OF CHEMICAL SAFETY

AND POLLUTION PREVENTION 

### UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON

, D.C. 20460

Date: November 3, 2014

PC Code: 111601

DP Barcode: 419419

MEMORANDUM

SUBJECT: Registration Review Problem Formulation for Oxyfluorfen

FROM: Robin Sternberg, Ph.D., Wildlife Biologist

He Zhong, Ph.D., Biologist

Environmental Risk Branch 1

Environmental Fate and Effects Division (7507P)

THROUGH: Sujatha Sankula, Ph.D., Branch Chief

Meghan Radtke, Ph.D., Acting RAPL

Environmental Risk Branch 1

Environmental Fate a nd Effects Division (7507P)

TO: Benjamin Askin, Risk Review Manager

Tom Moriarty, Team Leader

Neil Anderson, Branch Chief

Risk Management and Implementation Branch 1

Pesticide Re-Evalua tion Division (7508P)

Attached is the Registration Review problem formulation for the herbicide oxyfluorfen.

### 2 

# REGISTRATION REVIEW

PROBLEM FORMULATION

______________________________________________________________________________



# Oxyfluorfen

CAS Number

US EPA PC CODE 111601

Prepared by:

Robin Sternberg, Ph.D., Wildlife Biologist

He Zhong, Ph.D., Biologist

Edom Seifu, Intern

Environmental Risk Branch 1

Reviewed by:

Edward Odenkirchen, Ph.D., Senior Science Advisor

Faruque Khan, Ph.D., Senior Fate Scientist

Environmental Risk Branch 1 U.S. Environmental Protection Agency

Office of Pesticide Programs

Environmental Fate and Effects Division

Environmental Risk Branch I

1200 Pennsylvania Ave., NW

Mail Code 7507P

Washington, DC 20460

### 3 

## 1 Executive Summary

The Environmental Fate and Effects Division (E FED) has completed the preliminary problem

formulation (attached) for the ecological risk, environmental fate, endangered species, and

drinking water assessments to be conducted as pa rt of the Registration Review of oxyfluorfen, a

light-dependent peroxidizing herbicide (LDPH) . The problem formulation describes the

methods to be used during the completion of dr inking water and ecological risk assessments in

support of Registration Review a nd provides an overview of the environmental fate, ecological

effects, and potential risks associated with the use of oxyfluorfen as well as uncertainties unique

to risk assessment of oxyfluorfen. This document also identifies additional studies that would be

beneficial to conducting an ecolo gical risk assessment. Majo r findings include the following

data needs and the uncerta inties described below:

All studies should be conducted with parent oxyfluorfen.

 OCSPP 835.2240: Aqueous photolysis (TGAI)

 OCSPP 835.4300: Aerobic aquatic metabolism (TGAI)

 OCSPP 835.4400: Anaerobic aquatic metabolism (TGAI)

 OCSPP 850.6100: ECM/ILV for soil and water

 OCSPP 850.2100: Avian acute oral toxi city test, passerine species

 OCSPP 850.1075: Fish acute toxicity test, es tuarine/marine fish or fathead minnow

 OCSPP 850.1350: Fish early life stage toxic ity test, estuarin e/marine species

 Special study (OECD 213) : Acute oral toxicity to adult honey bees

 Special study: Chronic oral toxicity to adult honey bees

 Special study: Chronic and acute toxicity to larval honey bees

 Special study: Pollinator feed ing/semi-field/pollen and nectar residue studies – The need

for these studies is contingent upon the results of lower tier bee studies.

 OCSPP 850.3040: Field testing for pollinators – Th e need for field testing is contingent

upon the results of lower tier bee studies.

Justifications for these data needs as well as as sumptions that will be made in the absence of

these data are provided in Section 11

.

 The potential for phototoxic effects is a se rious concern for oxyfluorfen. With the

exception of a fish early life st age toxicity test, a ll of the toxicity tests were conducted

under standard laboratory lighting conditions which may result in an underestimation of

the toxicity of oxyfluorfen to some taxa unde r natural sunlight conditions. No further UV

enhanced ecotoxicity studies are being request ed, but the uncertainti es associated with

data generated under standard laboratory light ing conditions will be characterized in the

risk assessment.

 The stressors of ecological concern for aqua tic organisms are oxyfluorfen and any major

degradates identified in the requested aquatic fate studies. As a conservative estimate,

the unknown percentage(s) of the major degradate(s) will be tr eated as parent unless the

amount(s) of maximum formation are identified as a result of the data call-in. Degradate

MW-332, which formed at >10% in the a quatic photolysis study (MRID 42129101), is

### 4 estimated to be 3-4 times less toxic than the parent. Additional information for the

maximum formation of MW-332 is needed to de termine if it will be included or excluded

in the Registration Review eco logical risk assessment.

 Most labels do not specify a minimum appli cation interval. In addition, the maximum

yearly application rate is not identified for many of the labe ls. In the absence of this

information, conservative assumptions will be made.



## 2 Introduction

Oxyfluorfen is a light-dependent peroxidizing he rbicide (LDPH) in the diphenyl ether chemical

class. It is used for pre- and post-emergence control of mono cotyledonous and broad leaf weeds

in agricultural crops (includi ng fallow fields prior to plantin g), ornamental nurseries, and

residential areas. LDPHs target a specific en zyme, protoporphyrinogen oxidase, in the heme and

chlorophyll biosynthetic pathway. Inhibiting protoporphyringen oxida se in plants leads to an

accumulation of phototoxic heme and chlorophyll precursors that, in the presence of light,

produce activated oxygen species which rapi dly disrupt cell membrane integrity.

EFED evaluated the most recent ecological risk assessments for oxyfluorfen in association with

updated toxicity, exposure, and usage information to determine if sufficient data are available

and if further updates are needed to support Registration Review. Recent ecological risk

assessments for oxyfluorfen include the 2002 EFED chapter for the Reregistration Eligibility

Decision (RED) document (original, DP 250187, August 31, 2001; revised, DP 279498,

December 11, 2001; revised, DP 282182, May 2, 2002) and a 2008 litigation assessment for the

California red-legged frog ( Rana aurora draytonni ) (USEPA, 2008) 1 

### . In addition, EFED

considered the latest Agency science polic ies and risk assessment methodologies.



## 3 Use Characterization

Oxyfluorfen is a pre- and post-emergent diphenyl ether herbicid e used to control

monocotyledonous and broad leaf weeds. Register ed use sites of oxyfluorfen are provided in

Table 3-1 . Oxyfluorfen is formulated as an emulsi fiable concentrate, flowable concentrate,

granule, ready-to-use liquid, and soluble concentrate/liquid. Treatment equipment includes

aircraft, low pressure ground sprayer, sprinkle r irrigation, spreader, a nd ready-to-use spray

container. EFED will use application scenarios that result in maximum exposure scenarios for a

given use for the risk assessment (see Appendix A ). The Label Data Report produced by

BEAD, located in the docket, identifies legitimate gaps in label information by EPA Reg. No.

Specifically, many labels identify a seasonal maxi mum application rate or maximum application

rate per crop cycle. They do not identify a ma ximum yearly rate (lbs a.i./year), which is

necessary for ecological risk asse ssment. Most labels do not sp ecify an application interval

either. The absence of a maximum single applic ation rate, an application interval, a maximum

rate (lbs a.i./year), and/or application method on labels may result in conservative assumptions.

1 http://epa.gov/espp/litstatus/effects/redleg-frog/index.html

### 5 Table 3-1. Registered Uses of Oxyfluorfen by Use Group

Terrestrial Food Terrestrial Non-Food Terrestrial Food + Feed

Apricot

Artichoke Agricultural fallow/idleland/

conservation reserve Agricultural fallow/idleland/

conservation reserve

Avocado Agricultural uncultivated areas Almond

Blackberry Christmas tree plan tations Corn (unspecified)

Broccoli Citrus Corn, field

Cabbage Cocoa Cotton (unspecified)

Cauliflower Coffee Garbanzos (including chick peas)

Cocoa Conifers (plantations/nurseries) Grapes

Coffee Deciduous trees Mi nt/peppermint/spearmint

Date Eucalyptus Peppermint

Feijoa (pineapple guava) Grapes Pome fruits

Fig Grasses grown for seed Soybeans (unspecified)

Garlic Guava Stone fruits

Guava Jojoba Tree nuts

Horseradish Lesquerella

Kiwi fruit Nonagricultural uncultivated areas/soils Forestry

Nectarine Nursery stock Cottonwood (forest/shelterbelt)

Olive Onion Forest trees (softwoods, conifers)

Onion Ornamental and/or shade trees Shelterbelt plantings

Papaya Ornamental woody shrubs and vines

Peach

Persimmon Ornamentals (unspecified)

Pineapple Terrestrial Non-Food + Outdoor

Residential

Pistachio Rose Rose

Plum Sweet peas (ornamental)

Pomegranate Tree nuts

Prune

Raspberry (black, red)

Sage, clary

Taro

Walnut (English/black)



## 4 Conclusions from Previous Risk Assessments

4.1 Ecological Risk Assessments

EFED has conducted ecological risk assessments on oxyfluorfen that serve as a basis for this

problem formulation, including the 2002 EFED ch apter for the RED document (original, DP

250187, August 31, 2001; revised, DP 279498, December 11, 2001; revised, DP 282182, May 2,

2002) and a 2008 litigation assessment fo r the California red-legged frog ( Rana aurora

draytonii ) (USEPA, 2008) 2 

### . EFED’s RED chapter stated that oxyfluorfen presents the greatest

risks to:

 terrestrial plants thr ough spray drift of li quid formulations and

 aquatic organisms through spray drift of liqui d formulations and r unoff of dissolved and

soil-entrained oxyfluorfen.

Risk concerns were also identified for bird s and mammals from chronic exposures. The RED

also indicated that oxyfluorfen may be more toxic in the presence of intense light (i.e., UV),

which may result in enhanced toxicological eff ects that were not observed in tests conducted

2 http://epa.gov/espp/litstatus/effects/redleg-frog/index.html

### 6 under laboratory lighting. Ecological effects studies called in as a result of the RED are provided

in Table 4-1

.

Table 4-1. Status of Studies Reque sted as a Result of the RED

Data Requirement Study

submitted? MRID Classification

OPPTS 850.1400: Estuarine/marine fish

early-life stage Yes 46794501 Invalid

(due to low hatching success in

the controls and high variability

in measured test concentrations)

OPPTS 850.1735: Whole sediment acute

toxicity invertebrates, fresh water Yes 46585102 Supplemental

(due to lower than recommended

light intensity)

OPPTS 850.1740: Whole sediment acute

toxicity invertebrates, estuarine/marine Yes 46585103 Supplemental

(due to uncertain exposure

concentrations and not using

continuous lighting per guideline)

OPPTS 850.1300: Daphnid chronic

toxicity Yes a 42142305

45550201

92136106 Acceptable

OPPTS 850.2300: Avian reproduction

studies, quail Yes 46070102 Acceptable

OPPTS 850.2300: Avian reproduction

studies, duck Yes 46070101 Acceptable

OPPTS 850.4225: Seed

germination/seedling emergence (TEP) Yes 45861101 Acceptable

OPPTS 850.4250: Vegetative vigo r (TEP) Yes 45861102 Acceptable

OPPTS 850.4400: Aquatic plant growth Yes 45861103

( Lemna gibba ) Supplemental

(due to uncertain exposure

concentrations)

45861104

( Anabaena

flos-aquae ) Supplemental

(due to uncertain exposure

concentrations)

45861105

( Navicula

pelliculosa ) Supplemental

(due to uncertain exposure

concentrations)

45861106

( Skeletonema

costatum ) Supplemental

(due to uncertain exposure

concentrations)

Non-guideline: Fish phototoxicity study Yes 46585104 Acceptable

a raw data for existing study submitted



### The RED included several risk mitigations to reduce environmental risk concerns for

oxyfluorfen:

 Lowering the maximum rate to 1.5 lbs ai/broadcast acre/s eason for food crops and 2

lbs ai/acre/season for conifer seedlings.

 For liquid or granular formulations applie d to field-grown ornamentals, lowering the

seasonal maximum rate to 4.5 lbs ai/A (1.5 lbs ai/A/application). For granulars

applied to containerized ornamentals, lowe ring the rate to a seasonal maximum of 6

lbs ai/A (2 lbs ai/A/application).

### 7  The addition of a 25 foot, no-spray, ve getative buffer zones around surface water

bodies such as rivers, lakes, streams, and ponds.

 Requiring the use of a coarse , very coarse, or extrem ely coarse spray [ASAE 572

definitions for standard nozzles, or a vol ume median diameter (VMD) of 385 microns

or larger for spinning atomizer nozzles].

For the litigation assessment, the Agency ma de a Likely to Adversely Affect (LAA)

determination for the CRLF from the use of oxyf luorfen. Additionally, the Agency determined

that there is the potential for modification of CRL F designated critical habitat from the use of

oxyfluorfen.

4.2 Drinking Water Exposure Assessments

A drinking water exposure assessment was con ducted for oxyfluorfen in 2001 (USEPA 2001, DP

277546) to support the RED (USEPA DP 279498). Exposure estimates of oxyfluorfen from

currently labeled uses that produced maximum exposure via drinking water from surface water

were:

 23.4  g /L for the 1 in 10 year annua l peak concentration (acute);

 7.1  g /L for the 1 in 10 year annual mean concentration (chronic); and

 5.7  g /L for the 36 year annual mean concentration.

These concentrations were de rived from modeling oxyf luorfen use on Oregon apples with an

application rate of 2 lb a.i./A.

The 

### SCI-GROW model concentration estimat e of oxyfluorfen in drinking water from shallow

groundwater sources was 0.08  g /L.

4.3 Clean Water Act Programs

Oxyfluorfen was identified as a cause of impa irment for two water bodies (Gilsizer Slough and

Live Oak Slough in California) listed as impair ed under section 303(d) of the Clean Water Act

http://iaspub.epa.gov/tmdl_waters10/attains_im paired_waters.control?p_cause_name=OXYFLU

ORFEN . No Total Maximum Daily Load (TMDL) crit eria have been developed for oxyfluorfen.

Aquatic benchmarks have been established fo r chemical oxyfluorfen and are available at

http://www.epa.gov/oppefed1/ecoris k_ders/aquatic_life_benchmark.htm . Any data submitted or

otherwise located as part of the Registration Re view process will be used to update aquatic life

benchmarks, if applicable.



## 5 Environmental Fate and Transport

The major route of oxyfluorfen dissipation is aqueous photolysis. The compound, when

dissolved in water, is readily degraded by sunlight (half-lives = 4-5 days, MRIDs 42142307 and

42142308) and by artificial light with 330-800 nm wavelength (hal f-lives = 6-8 days, MRID

42129101). Oxyfluorfen moderately degraded by sunlight when on soil surfaces (half-life = 28

days, a minor route of dissipation), and is stable to hydrolysis (> 97% parent after 30 days at pH

4, 7, and 10). Its soil microbial degradation was slow with aerobic soil metabolism half-lives

ranging from 69 to 596 days [t 1/2 

### = 77 days in a sandy loam soil, t 1/2 

### = 68 days in a loamy

### 8 sand/sandy loam soil, and t 1/2 

### = 69 days in a clay loam soil from France (MRID 46373103); t 1/2 

### ≈

290 days in a clay loam soil and t 1/2 

### = 575 days in a sandy loam soil (MRID 42142309)].

Anaerobic soil metabolism half-lives ranged be tween 554 and 603 days. The aerobic soil halflives demonstrated a broad range, which could be attributed to decrea sed microbial population

observed in one study (MRID 42142309). Open liter ature data suggest that the rate of

oxyfluorfen dissipation in soil depe nds on both temperature and soil moisture content; half-lives

ranged from 72 to 160 days (Yen et al ., 2003). In the water column, oxyfluorfen dissipated with

half-lives of 4 and 5 days, in sediment with half-lives of 30 to 51 days (MRID 46373104). Once

the soil-bound oxyfluorfen reaches deep or turbid surf ace water, it will persist since it is stable to

hydrolysis and light penetra tion would be limited.

Adsorption/desorption studies suggest oxyfluorfen is slightly mobile, in sandy soils, sandy loam,

and clay loam (K

oc 

### = 2,891 L/kg, 8,076 L/kg, and 5,585 L/kg, respectively), and hardly mobile in

silty clay loam soils (K

oc 

### = 32,381 L/kg) (MRID 42142311). Howeve r, in coarse texture sandy

soils of low organic matter c ontent, oxyfluorfen has the pote ntial to leach into shallow

groundwater less than thr ee meters deep (Yen et al . 2003).

Oxyfluorfen dissipated from bare ground loamy sand and clay loam soil plots in California with

half-lives of 53 and 58 days, respectively. The half-lives for degradates RH-4672, RH-0671, and

RH-2382 varied from 37 to 61 days. These half- lives were estimated based on the formation and

decline curves from the field dissipation study (MRID 43840101). The dissipation half-lives for

oxyfluorfen ranged from 30 to 103 days in Canadian muck soil (Frank et al . 1991). In another

study conducted in Australian vineyards during a cool and damp season, the half-life was 119

days (Ying and Williams 2000).

Volatilization loss of oxyfluorfen from soil and water systems is expected to be insignificant

based on oxyfluorfen low vapor pressure (3.54 x 10 -7 

### torr at 25 o 

### C) and Henry's Law Constant

(8.21 x 10 -7 

### atm·m 3 

### /mol). Considering this low volatility along with high sensitivity to photolytic

degradation, oxyfluorfen is not expected to have long-range atmospheric tr ansport in appreciable

quantities.

Oxyfluorfen is expected to bioconcentrate in fish, which is in concurrence with its high K

ow 

### value of 29,400 (log K

ow 

### = 4.46). The bioconcentration fact ors observed in a bluegill sunfish

study were 450 and 605X in muscle, 3265 and 4360X in viscera, and 1075 and 2200X in whole

fish (MRID 00096883). Elimination of accumulated residues by day fourteen of depuration was

82% in viscera and 91% in whole fish.

In summary, oxyfluorfen is expe cted to reach surface water via transport during runoff events

and via spray drift during app lication events. The chemical is unlikely to leach into

groundwater, although limited vertical movement th rough soils may be possible in sandy soils of

low organic matter. Tables 5-1 list the environmental fate prope rties of oxyfluorfen, along with

the major and minor degradates detected in the submitted environmental fate and transport

studies.

### 9 Table 5-1. Physical, Chemical and Enviro nmental Fate Propert ies of Oxyfluorfen

Property Value Source & Study

Classification

PC Code 111601

Common name Oxyfluorfen MRID 44828902

Acceptable

Product chemistry

CAS Registry No. 42874-03-3 MRID 44828902

Chemical name (CAS) 2-Chloro-1-(3-ethoxy-4-nitrophenoxy)-4-

(trifluoromethyl)benzene MRID 44828902

IUPAC name 2-chloro-alpha, alpha, alpha-trifluoro- p -tolyl 3-

ethoxy-4-nitrophenyl ether MRID 47303701

Acceptable

Product chemistry

Synonyms RH-32915

RH-2915 (alternate)

RH-915 (alternate) MRID 44828902

SMILES CCOC1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(

F)F)Cl)[N+](=O)[O-] EPI Suite, v4.1

Structure Toxnet

Molecular formula C 15 H 11 ClF 3 NO 4 MRID 44828902

Physical and Chemical Properties

Molecular weight (g/mole) 361.7 MRID 44828902

Color Brown MRID 44828902

Physical state (24 oC) Crystalline solid MRID 44828902

Vapor pressure (25 oC) 3.54 x 10 -7 torr @ 25oC

9.78 x 10 -7 torr @ 32oC

2.80 x 10 -6 torr @ 44oC MRID 44828902

Henry’s Law constant

(Exper Database) 8.2 x 10 -7 atm x m 3 /mol EPI Suite, v4.1

pH (1% aqueous dispersion of

GOAL® HIGH PURITY) 9.35 @ 20oC MRID 44828902

### 10 Property Value Source & Study

Classification

Relative density 1.53 g/cm 3 @ 20 o C MRID 44828902

Solubility in water (25oC) 0.116 mg/L MRID 44828902

Partition coefficient 2.94 x 10 4 or

log K

ow = 4.47 MRID 44828902

Bioconcentration in Fish (bluegill

sunfish) Muscle: 450 & 605X

Viscera (non-edible tissues): 32265 & 4360X

Whole fish: 1075 & 2200X

By day 14 of depuration, elimination of residues

was 82% in viscera and 91% in whole tissue. MRID 00096883

Supplemental

Environmental Fate Properties

Hydrolysis half-life

pH = 4

pH = 7

pH = 10 Stable

Minor Degradate

1.2-1.7% RH-34670 MRID 00134454

Acceptable

Photodegradation in Water (t 1⁄2 ) 3.7 to 5.4 days (nature light, 3.4 – 4.4 W/cm 2 )

6.27 and 7.56 days (330 – 800 nm @ 150 W/m 2 )

Identified degradates with unknown amount

(MRID 42129101)

RH -34800, RH-34670, RH-45469, RH-34860,

MW 180, MW 327 and MW 332

(MRID 42142307&08)

RH-4800, 3-chloro-4-hydroxy benzoic acid, RH4670, RH-5298, and RH-5451

Unidentified degradates (MRID 42142307&08)

15.3-16.8% nonpolar residues at day 8

37.2-41.3% polar residues at day 15-20 MRID 42142307

MRID 42142308

MRID 42129101

Supplemental

Photodegradation on Soil (t 1⁄2 ) 28 days

Minor Degradates:

6.5% methyl ester of 3-Cl,4-OH benzoic acid,

6.5% 3-Cl,4-OH benzoic acid

18.5% composed of 4 unidentified degradates

7.5% unidentified in acidified methanol extracts

8.1% CO 2 collected in NaOH trap MRID 41999901

Acceptable

Aerobic Soil Metabolism (t 1⁄2 ) 556-596 days (sandy loam soil)

291-294 days (clay loam soil)

Minor degradate, 2.9% RH-34800

Nonextractable residue, up to 43%

European soils:

77 days-sandy loam, MRID 42142309

Acceptable

MRID 46373103

Supplemental

### 11 Property Value Source & Study

Classification

68 days-loamy sand/sandy loam,

69 days-clay loam

Eight unidentified minor degradate: 5.5% M1, and

≤ 2.1% for M3, M4, M5, M6, M7, M8, and M9)

Nonextractable residue, 37.3-45.4% at 120 days

Anaerobic Soil Metabolism (t 1⁄2 ) 554 and 603 days

Degradates: None MRID 42142310

Supplemental

Aerobic Aquatic Metabolism t 1⁄2 in

Total System (t 1⁄2 in water/sediment

system) River water/sandy loam sediment

Water: 4.7 days

Sediment 50.6 days

Total system 39.6 days

Pond water/silt loam sediment

Water 3.9 days

Sediment 31.5 days

Total system 29.6 days

Eight unidentified minor degradates with 9.6%

M5 and the rest M1 to M9 ≤ 4.9%

Nonextractable residue, 42.6-43.3% at 100 days MRID 46373104

Supplemental

Anaerobic aquatic metabolis m half-life No data

Leaching & Adsorption (ADS)

K

oc (L/kg) Sand: 2891

Sandy loam: 8076

Clay loam: 5585

Silty clay loam: 32381 MRID 42142311

Supplemental

Terrestrial Field Dissipation (t 1⁄2 )

(CA bare ground loamy sand and clay

loam soil plots) Parent: 53 and 58 days

Degradates (RH-4672, RH-0671 and RH-2382):

37 to 62 days.

RH-4672 was max of 0.379 ppm, RH-0671 was

0.044 ppm, and RH-2382 was 0.095 ppm

immediately post treatment MRID 43840101

Supplemental

Drift Field Evaluation

(using lettuce as bioassay) Visible symptoms: 800 m downwind

Quantifiable symptoms up to 100 MRID 43840101

Supplemental



### 5.1 Transformation Products

Several degradates have been reported for oxyfl uorfen but only a few have been identified and

quantified. The major degradate found in the en vironmental fate studies was MW-332 [2-chloro1-(3-ethoxy-4-hydroxyphenol)-4 -(trifluoromethyl) benzene], whic h was identified in the aqueous

photolysis study (MRID 42129101) to be > 10 % of th e applied radioactivit y. Other degradates

identified in the aqueous photolysis study but not quantified incl ude RH-34670, RH-34860, RH34800, RH-45469, MW-327, and MW-180. In the hydrolysis study (MRID 134454), RH-34670

### 12 [(2-chloro-1-(3-hydroxy -4-nitrophenoxy)-4-(trifluoromethyl ) benzene] was identified at a

maximum concentration of 1.2-1.7% of the applie d radioactivity. In the soil photodegradation

study, isolated volatile material was composed of two degradates, RH-34800 and RH-36329, the

methyl ester of 3-Cl,4-OH benz oic acid. RH-34800 was the only degradate identified in the

aerobic soil metabolism study (MRID 42142309) at a maximum concentration of 2.9 % of the

applied radioactivity. Another aerobic soil study showed that oxyfluorfen mineralized to CO 2 

### ( ≤

21% of the applied) with the formation of multiple unidentifie d minor transformation products,

each ≤ 2.1%, but one at 5.8%, and of ≤ 45% bound residues (MRID 46373103). Oxyfluorfen

applied to water dissipated by mineralization to ≤ 9.4% CO 2 

### and unidentified minor

transformation products, each ≤ 4.9%, but one at 9.6% of the a pplied, and by incorporation into

the organic matter of the sediment (extractable residues ≤ 71% at 7 days; nonextractable residues

≤ 59% of the applied at 100 days; MRID 46373104). There were no degradates isolated and

identified in the anaerobic soil metabolism, aer obic aquatic metabolism, and leaching studies.

Presently no fate and ecotoxicol ogical data are available for oxyf luorfen degradates. Chemical

structure examples of selected oxyfl uorfen degradates are provided in Figure 5-1

.

2-chloro-1-(3-hydroxy-4-nitrophenoxy)-4-( trifluoromethyl) benzene (RH-34670)

Acyl-670 (RH-45469)

2-chloro-1-(3-ethoxy-4-hydroxy-phenoxy)-4-( trifluoromethyl) benzene (MW-332)

Figure 5-1. Degradate Structures O Cl

CF 3 NO 2 OH

O Cl

CF 3 NHCOCH 3 OCH 2 CH 3

O Cl

CF 3 OH OCH 2 CH 3

### 13 

## 6 Receptors

Summaries of the most sensitiv e endpoints used to characterize the toxicity of oxyfluorfen to

aquatic and aquatic organisms are provided in Table 6-1 . Summaries of all submitted

oxyfluorfen toxicity data can be found in Appendix B . No toxicity data are available for any of

the degradates of oxyfluorfen.

For oxyfluorfen, no data are av ailable for the following:

 chronic toxicity to estuarine/marine fish;

 acute oral toxicity to a passerine species; and

 acute and chronic oral toxicity to adult and larval honey bees.

Oxyfluorfen is classified as: up to highly toxic to fish on an acute basis; up to very highly toxic

to aquatic invertebrates; practica lly non-toxic to birds on an acute oral basis (based solely on data

for bobwhite quail); practically non-toxic to birds on a sub-acute dietary basis; practically nontoxic to mammals on an acute or al basis; and practically non-t oxic to adult honey bees on an

acute contact basis.

More recently submitted toxicity studies were conducted using a technical grade of oxyfluorfen

with purity ranging from 95 to 99% whereas ol der studies were conducted using a technical

grade of oxyfluorfen with purity ranging from 71 to 85%. The newer technical material has a

similar profile of impurities when compared to the older material, but in reduced concentrations

(USEPA, 2002). In the 2002 RED (USEPA, 2002), the human health effects assessment noted

reduced toxicity in older studi es with a 98% product and used newer studies with the 98%

product to identify t oxicological endpoints when studies with newer and older technical material

were available. Based on this, it is possible th at the newer, higher purity technical material will

have a reduced toxic effect on species evaluated in the ecologi cal risk assessment; however, no

data have been submitted to the Agency to c onfirm the extrapolation. Within the suite of

ecological effects studies, limited comparisons can be made due to lack of data for both the

newer, higher purity and older, lo wer purity technical material. When available, toxicity data for

the newer, higher purity technical will be used in the assessment as su ch data would better

represent the material currently used in the environment.

As previously noted in the CRLF litigation a ssessment (USEPA, 2008) and EFED RED chapter

(original, DP 250187, August 31, 2001; revise d, DP 279498, December 11, 2001; revised, DP

282182, May 2, 2002), the potential for phototoxic eff ects is a serious con cern for oxyfluorfen.

LDPHs are a class of weed cont rol chemicals that act in plants by inhibiting the enzyme

protoporphyrinogen oxidase (protox), which is the last common enzyme in the heme and

chlorophyll biosynthetic pathways. Protox exists in both plants and animals and the enzyme

from both sources has been shown to be highly sensitive to many LDPHs. Several studies have

documented enhanced toxicity of LD PHs to fish in the presence of uV light compared to toxicity

observed under standard laborator y lighting. Given that aquatic organisms are likely to be

exposed simultaneously to LDPH and uV light in natural se ttings, concerns have been raised that

guideline chronic exposure laborato ry tests may underestimate the toxicity of LDPH in the field.

With the exception of a fish early life stage toxicity test (MRID 46585104), all of the toxicity

tests were conducted under standard laborator y lighting conditions which may result in an

### 14 underestimation of the toxicity of oxyfluorfen to some taxa under natural sunlight conditions.

The NOAEC of 1.3 μg/L for the fish early life stage study conducted under enhanced UV

lighting simulating summer light intensity for the Florida or California latitudes (MRID

46585104) is over an order of magnitude lower than the NOAEC of 38 μg/L for a fish early life

stage study conducted with standard laboratory lighting (MRIDs 00099270, 00030249, and

92136057). In the study with enhanced UV lighting, the larval fish appeared to hatch

prematurely compared to the control and then di e. Based on the mode of action, it is possible

that disruption of the egg cell memb rane caused the premature hatch.

The extent to which UV light e nhances the toxicity of oxyfluorfe n to other taxa or other life

stages is unknown and could be obs erved in other taxa such as a quatic invertebrates, birds, and

mammals (Birchfield and Casida, 1997). Anemia and other hematologic consequences have

been observed in developmental studies w ith mammals (USEPA, 2002). In wild mammal

populations, hematologic effects have the potential to magnify since the lack of natural sunlight

in the laboratory reduces the li kelihood of activating the photot oxic effects of oxyfluorfen.

It should be noted that the classification of an acute st udy with sheepshead minnow (MRID

41698801) has been downgraded from “acceptable” to “supplemental” due to considerable

uncertainty regarding the exposure concentratio ns. There was a large discrepancy between

nominal (13, 22, 36, 60, and 100 mg/L) and mean-measured (0.07, 0.06, 0.13, 0.11, and 0.17

mg/L, respectively) concentrations because the range of nominal concentrations greatly exceeds

the solubility of oxyfluorfen (0.116 mg/L). Most of the chemical precipita ted out of solution and

accumulated on the surface of water in the test ve ssels. The samples for quantification were not

centrifuged and/or filtered before being analyzed. In addition, th e concentrations of the nominal

60 and 100 mg/L treatment levels were not stable throughout the test; measured test

concentrations for these trea tment levels declined from 0.16 and 0.28 mg/L at 0 hours to 0.06

and 0.06 mg/L at 96 hours, respect ively. Although there was no mo rtality in the study and the

test organisms appeared normal, surfacing was observed at nominal concentrations ≥ 36 mg/L.

This observation was attributed to low dissolv ed oxygen. The study author proposed that the

drop in dissolved oxygen could have been due to the accumulation of precipitated chemical on

the surface of the water.15Table 6-1. Summary of Most Sensitive Endpoints from Toxicity Studies with OxyfluorfenStudy TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationAvian acute oral:single dose, 21-dayobservation (insteadof usual 14-dayobservation)Oxyfluorfentechnical(70.2)Bobwhite quail(Colinus virginianus)LD50> 2150 mg/kg-bw (nom)NOAEL < 1470 mg a.i./kg-bw (nom)(1 mortality at 2150 mg /kg-bw; sublethal effects: weakness,anorexia, piloerection, and abnormal cage droppings at 1470 and2150 mg/kg-bw, recovery by day 7; food consumption severelydepressed at 1470 and 2150 mg/kg-bw during first 2 and 7 daysrespectively; weight loss at 1470 and 2150 mg/kg-bw during first3 days)Practically non-toxicMRIDs 92136102,42255901, and42142301AcceptableAvian acute oral NA Passerine species No data NAAvian sub-acutedietary: 5-dayexposure; 3-daypost-exposureobservationOxyfluorfentechnical(70.2)Mallard duck(Anas platyrhynchos)LC50> 5000 mg a.i./kg-diet (nom)NOAEC = 312 mg a.i./kg-diet (nom)LOAEC = 625 mg a.i./kg-diet (nom)(10% [1/10] mortality at 5000 mg/kg-diet; sublethal effects:anorexia at 5000 mg/kg-diet on days 2-3; concentrationdependent reduction in food consumption at≥625 mg/kg-dietduring exposure period; reduction in food consumption at allreatment levels on days 6-8; NOAEC based on reduction in foodconsumption)Practically non-toxicMRIDs 92136104and 42142303AcceptableOxyfluorfentechnical(70.2)Bobwhite quail(Colinus virginianus)LC50> 5000 mg a.i./kg-diet (nom)NOAEC = 625 mg a.i./kg-diet (nom)LOAEC = 1250 mg a.i./kg-diet (nom)(no mortality; sublethal effects: reduction in body weight gainsat 1250 and 2500 mg/kg-diet during days 0-5; body wieght loo at5000 mg/kg-diet by day 5; food avoidance during days 3-5 andreduction in food consumption durings days 0-5 at 2500 and5000 mg/kg-diet; NOAEC based on reduction in body weightgain)Practically non-toxicMRIDs 92136103and 42142302AcceptableAvian reproduction:20 weeks(chronic)Oxyfluorfentechnical, purified(99.3)Bobwhite quail(Colinus virginianus)NOAEC = 124 mg a.i./kg-diet (mm)LOAEC = 256 mg a.i./kg-diet (mm)MRID 46070102Acceptable16Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassification(based on most sensitive parameter of survivor weight; ratio ofhatchling survival to number of hatchlings, viable embryos, liveembryos, number of hatchlings, ratio of eggs set to eggs laid, andratio of number of hatchlings to eggs laid, ratio of hatchlingsurvival to eggs set also affected)Oxyfluorfentechnical, purified(99.3)Mallard duck(Anas platyrhynchos)NOAEC = 506 mg a.i./kg-diet (mm)LOAEC = 751 mg a.i./kg-diet (mm)(based on eggs laid, eggs set, viable embryos, the ratio of viableembryos to eggs set, live embryos, number of hatchlings, theratios of normal hatchlings to eggs laid and to eggs set, andhatchling survival)MRIDs 46070101AcceptableMammalian acuteoral, limit: singledose; 14-dayobservationOxyfluorfen(96)Rat(Rattus norvegicus)LD50> 5,000 mg a.i./kg-bw(no effects)Practically non-toxicMRID 44712010AcceptableOxyfluorfentechnical 95(97.1)Rat(Rattus norvegicus)LD50> 5,000 mg a.i./kg-bw(no effects)Practically non-toxicMRID 44828903AcceptableMammalian acuteinhalationOxyfluorfen(96)Rat(Rattus norvegicus)LC50> 3.71 mg/L MRID 44712012Mammalian 2-generationreproduction(chronic)Oxyfluorfen Rat(Rattus norvegicus)ParentalNOAEC = 400 mg a.i./kg-dietLOAEC = 1600 mg a.i./kg-diet(based on parental effects including mortality, decreased bodyweight, liver and kidney histopathology)ReproductiveNOAEC = 400 mg a.i./kg-dietLOAEC = 1600 mg a.i./kg-diet(based on decreased body weight and decreased live pups/litter)MRID 42014901AcceptableAcute contact withadult honey bees:single dose, 96-hourobservationOxyfluorfentechnical(71.4)Adult honey bee(Apis mellifera)LD50> 100 μg a.i./bee (nom)NOAEL: Not specified(4-5% mortality across control and 3 treatment concentrations)Practically non-toxicMRID 42368101AcceptableAcute oral withhoney bee adultsNA Adult honey bee No data NA17Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationAcute oral withhoney bee larvaeNA Larval honey bee No data NAChronic oral withhoney bee adultsNA Adult honey bee No data NAChronic oral withhoney bee larvaeNA Larval honey bee No data NATerrestrial plantseedling emergence:minimum of 14 daysafter 50% of thecontrol plants hademergedGoal 2XL(23.1)Most sensitivemonocot: RyegrassEC25= 0.0063 lb a.i./A (nom)EC05= 0.00065 lb a.i./A (nom)NOAEC = 0.030 lb a.i./A (nom)Note: Since the NOAEC > EC25, the EC05will be used forassessing risk to listed species.(based on dry weight)MRID 45861101AcceptableMost sensitive dicot:LettuceEC25= 0.0072 lb a.i./A (nom)EC05= 0.0024 lb a.i./A (nom)NOAEC = 0.0080 lb a.i./A (nom)Note: Since the NOAEC > EC25, the EC05will be used forassessing risk to listed species.(based on dry weight)Terrestrial plantvegetative vigor:22-23 daysGoal 2XL(23.1)Most sensitivemonocot: OatEC25= 0.27 lb a.i./A (nom)EC05= 0.08 lb a.i./A (nom)NOAEC = 0.22 lb a.i./A (nom)(based on dry weight)MRID 45861102AcceptableMost sensitive dicot:LettuceEC25= 0.0078 lb a.i./A (nom)EC05= 0.00032 lb a.i./A (nom)NOAEC = 0.000035 lb a.i./A (nom)(based on dry weight)Freshwater fishacute: 96 hours,flow-through,standard laboratorylightingOxyfluorfen(94)Bluegill sunfish(Lepomismacrochirus)LC50(95% C.I.) = 200 (130-310) μg/L (nom)NOAEC: Not specified(no mortality at lowest test concentration, 56 μg/L; sublethaleffects: darkening, lethargy, and loss of equilibrium)Highly toxicMRIDs 00081856and 00038574AcceptableFreshwater fishacute: 96 hours,staticOxyfluorfentechnical(71.4)Rainbow trout(Oncorhynchusmykiss)LC50(95% C.I.) = 253 (186-355) μg a.i./L (mm)Probit slope (95% C.I.) = 2.4 (1.6-3.1)NOAEC = 37 μg a.i./L (mm)LOAEC = 83 μg a.i./L (mm)MRID 42129802Acceptable18Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassification(NOAEC based on mortalityand sublethal effects at≥83 μg/L;no mortality or sublethal effects at 37 μg/L; sublethal effects:lethargy in surviving fish at 398 and 1090 μg/L)Highly toxicFreshwater fish earlylife stage: 30 days,flow through,standard laboratorylightingOxyfluorfentechnical(71)Fathead minnow(Pimephales promelas)NOAEC = 38 μg/L (mm)LOAEC = 74 μg/L (mm)Note: This study was conducted under standard laboratorylighting.(based on reduction in fry survival, total length, and weigh)MRIDs 00099270,00030249, and92136057AcceptableFreshwater fish earlylife stage: 33 days,flow through,enhanced UVlighting (chronic)Oxyfluorfentechnical(99.3)Fathead minnow(Pimephales promelas)NOAEC = 1.3 μg a.i./L (TWA)LOAEC = 2.4 μg a.i./L (TWA)Note: This study was conducted under UV lighting simulatingsummer light intensity for theFlorida or California latitudes.(based on most sensitive endpoint of post-hatch survival;hatching success, post-hatch physical/behavioral abnormalities,and growth [length, wet weight, and dry weight] also affected)MRID 46585104AcceptableEstuarine/marinefish acute: 96 hours,staticOxyfluorfentechnical(71.4)Sheepshead Minnow(Cyprinodonvariegatus)LC50> 116 μg a.i./L (mm)NOAEC = 60 μg a.i./L (mm)(no mortality; sublethal effect of surfacingaat≥130 μg a.i./L)Practically non-toxic up to the limit of solubilityMRID 41698801SupplementalEstuarine/marinefish early life stage(chronic)Oxyfluorfen Estuarine/marinespeciesNo dataNote: A chronic toxicity endpoint for estuarine/marine fishcannot be estimated using an acute-to-chronic ratio (ACR) forfreshwater fish because the available freshwater fish chronictoxicity endpoints were generated for fathead minnow, a speciesfor which we do not have an acute toxicity endpoint.NAFreshwaterinvertebrate: 48hours, staticOxyfluorfen(82.2)Water flea(Daphnia magna)LC50(95% C.I.) = 1.5 (0.75-2.9) mg/L (nom)Moderately toxicMRID 00134449AcceptableFreshwaterinvertebrate acute:48 hours, flowthroughGoal 2XL (P)(23.2)Water flea(Daphnia magna)EC50(95% C.I.) = 80 (60-150) μg a.i./L (mm)NOAEC = 20 μg a.i./L (mm)(NOAEC based on mortalityand sublethal effects)Very highly toxicMRID 45217301Supplemental(due to highvariability in %recovery of testsubstance)19Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationFreshwaterinvertebrate lifecycle: 21 days, flowthrough (chronic)Oxyfluorfentechnical(71.8)Water flea(Daphnia magna)NOAEC = 13 μg a.i./L (mm)LOAEC = 28 μg a.i./L (mm)(NOAEC based reductions in adult survival, growth [length],and reproductive output)MRIDs 45550201,92136106, and42142305AcceptableEstuarine/marineinvertebrate: 96hours, staticOxyfluorfentechnical(74)Grass shrimp(Palaemonetes pugio)LC50(95% C.I.) = 32 (18-56) μg/L (nom)NOAEC = 18 μg/L (nom)Very highly toxicMRIDs 00134451and 30970117Supplemental(due to guidelinedeviations)Estuarine/marinemollusc: 96 hours,flow through, shelldepositionOxyfluorfentechnical(71.4)Eastern oyster(Crassostreavirginica)EC50(95% C.I.) = 69.3 (62.2-98.5) μg a.i./L (mm)bNOAEC = 37.5 μg a.i./L (mm)cVery highly toxicMRID 42378901AcceptableEstuarine/marineinvertebrate lifecycle: 30 days, flowthrough (chronic)Oxyfluorfentechnical(99.3)Mysid shrimp(Mysidopsis bahia)NOAEC = 8.1 μg a.i./L (TWA)LOAEC = 16 μg a.i./L (TWA)(NOAEC based on most sensitive endpoint of reproduction;survival, and growth [length and dry weight] also affected))MRID 46597701Supplemental(due to guidelinedeviations)Benthic freshwaterinvertebrate: 10days, flow through,spiked sedimentOxyfluorfentechnical(99.3)Midge(Chironomus tentans)Based on pore water concentrations (mm)LC50> 498.5 μg a.i./LNOAEC = 484.5 μg a.i./LBased on sediment concentrations (dry weight, mm)LC50> 97.6 mg a.i./kg-dwNOAEC = 55.7 mg a.i./kg-dwBased on sediment concentrations (organic carbon [OC], mm)LC50> 4880 mg a.i./kg-OCNOAEC = 2750 mg a.i./kg-OC(NOAEC based on mortality)MRID 46585102Supplemental(due to lower thanrecommended lightintensity)Benthicestuarine/marineinvertebrate: 10days, static, spikedsedimentOxyfluorfentechnical(99.3)Amphipod(Leptocheirusplumulosus)Based on pore water concentrations (mm)LC50(95% C.I.) = 130 (81-200) μg a.i./LProbit slope = 2.73±0.833NOAEC = 27.9 μg a.i./LBased on sediment concentrations (mm)LC50(95% C.I.) = 37 (26-53) mg a.i./kg-dwProbit slope = 2.54±0.44NOAEC = 16.0 mg a.i./kg-dwMRID 46585103Supplemental(due to uncertainexposureconcentrations andnot usingcontinuous lightingper guideline)20Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationBased on overlying water concentrations (mm)LC50(95% C.I.) = 42 (22-82) μg a.i./LProbit slope = 1.79±0.44NOAEC = 12.6 μg a.i./L(NOAEC based on mortality)Aquatic vascularplant: 14 days, staticrenewalOxyfluorfentechnical (99.1)Duckweed(Lemna gibba)EC50(95% C.I.) = 0.33 (0.20-0.38-27) μg a.i./L (m)NOAEC/EC05: Could not be determined(based on most sensitive endpoint of frond number)MRID 45861103Supplemental(due to uncertainexposureconcentrations)Aquatic nonvascular plant:96 hours, staticGoal 2XL (P)(23.2)Green alga(Selenastrumcapricornutum)EC50(95% C.I.) = 0.29 (0.27-30) μg a.i./L (mm)NOAEC = 0.10 μg a.i./L (mm)LOAEC = 0.26 μg a.i./L (mm)(NOAEC based on reduction in cell density)MRID 45271302AcceptableAquatic nonvascular plant:96-240 hours, static,sedimentOxyfluorfentechnical(99.1)Green alga(Pseudokirchneriellasubcapitata)96-hr EC50> 2.9 μg a.i./L (im)96-hr NOAEC = 1.4 μg a.i./L (im)96-hr LOAEC = 2.9 μg a.i./L (im)240-hr EC50> 2.9 μg a.i./L (im)240-hr NOAEC = 2.9 μg a.i./L (im)240-hr LOAEC > 2.9 μg a.i./L (im)(NOAEC based on reductions in cell density, growth rate, andbiomass)MRID 45581601Supplemental(due to guidelinedeviationsincluding use ofsediment)Aquatic nonvascular plant:120 hours, staticOxyfluorfentechnical(99.1)Cyanobacterium(Anabaena flos-aquae)EC50> 100 μg a.i./L (mm)NOAEC = 20.1 μg a.i./L (mm)LOAEC = 47.2 μg a.i./L (mm)(NOAEC based on most sensitive endpoint of biomass [areaunder the growth curve; cell density and growth rates alsoaffected)MRID 45861104Supplemental(due to uncertainexposureconcentrations)Aquatic nonvascular plant:120 hours, staticOxyfluorfentechnical(99.1)Freshwater diatom(Navicula pelliculosa)EC50= 29 μg a.i./L (mm)NOAEC = 19.2 μg a.i./L (mm)LOAEC = 49.7 μg a.i./L (mm)(based on most sensitive endpoint of cell density for EC50;growth rate and biomass alsoaffected with same NOAEC andLOAEC)MRID 45861105Supplemental(due to uncertainexposureconcentrations)21Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationAquatic nonvascular plant:96 hours, staticOxyfluorfentechnical(99.1)Marine diatom(Skeletonemacostatum)EC50= 1.10 μg a.i./L (mm)NOAEC = 0.65 μg a.i./L (mm)LOAEC = 1.20 μg a.i./L (mm)(based on most sensitive endpoint of biomass [area under thecurve]; cell density and growth rate also affected)MRID 45861106Supplemental(due to uncertainexposureconcentrations)Abbreviations: C.I. = confidence interval; ELS = early life stage;im = initial measured; mm = mean measured; nom = nominal; NA= not applicable; NS = notspecified; TEP = typicalend-use product; TWA = time-weighted averageaThis observation was attributed to low dissolved oxygen. The study author proposed that the drop in dissolved oxygen could have been due to the accumulationof precipitated chemical on the surface of the water.b based on pooled control datacbased on comparison to solvent control; NOAEC may be lower when using a comparison to the negative control

### 22 6.1 Ecological Incidents

A preliminary review on June, 23, 2014, of the Ec ological Incident Information System (EIIS,

version 2.1), which is maintained by the Agency ’s Office of Pesticide Programs, and the Avian

Monitoring Information System (AIMS), whic h is maintained by the American Bird

Conservancy, indicates a total of 25 reported ecological incidents associated with the use of

oxyfluorfen (see Appendix C ). These incidents involved terres trial, plant and aquatic taxonomic

groups. This total excludes incidents classified as ‘unlikely’ or ‘unr elated’ and only includes

those incidents with certainty ca tegories of ‘possible’, ‘probabl e’, and ‘highly probable’ (for

EIIS) and ‘possible’, ‘probable’, ‘likely’, ‘highly likely’ and ‘cer tain’ (for AIMS). Incidents

classified as ‘unlikely’ the result of or ‘unrel ated’ to oxyfluorfen will not be included in this

Problem Formulation or the ecological risk a ssessment conducted for Registration Review.

All of the oxyfluorfen incidents, excluding those classified as ‘unlik ely’ or ‘unrelated’, occurred

between 1996 and 2002. One of the oxyfluorfen in cidents involved aquatic animals, 7 involved

terrestrial animals, and 17 involved plants. The certainty categories rega rding the likelihood that

the use of oxyfluorfen caused the 25 incidents ranged from ‘possible’ (15 inci dents) to ‘probable’

(10 incidents). Eight of the inci dents were considered registered uses at the time of the incident,

12 involved misuses, and the legality of use wa s undetermined in 5 incidents. Eighteen of the

incidents involved additional chemicals besi des oxyfluorfen. Oxyfl uorfen residues were

reported in one of the incident reports involving aquatic organisms. The reported incidents for

oxyfluorfen involved 21 uses that are currently registered, and 4 in which the use site was not

specified. The reported incidents associated with the 21 currently registered uses had certainty

categories of ‘possibl e’ and ‘probable’.

In the risk assessment, the incidents will be fu rther evaluated to determine if the reported

incidents represent current patterns of us e for oxyfluorfen. 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.

In addition to the incidents reco rded in EIIS and AIMS, additiona l incidents have been reported

to the Agency in aggregated incident reports. Pesticide registrants re port certain types of

incidents to the Agency as a ggregate counts of incidents occu rring per product per quarter.

Ecological incidents reported in aggregate reports include those cat egorized as ‘minor fish and

wildlife’, ‘minor plant’, and ‘oth er non-target’ incide nts. ‘Other non-target’ incidents include

reports of adverse effects to insects and othe r terrestrial invertebra tes. For oxyfluorfen,

registrants have reported no minor fish and wildlife incidents, 42 minor plant incidents, and no

other non-target incidents. Unless additional in formation on these aggregated incidents become

available, they will be assumed to be representative of registered uses of oxyfluorfen in the risk

assessment.



## 7 Exposure Pathways of Concern

The environmental fate properties and use patter ns of oxyfluorfen indica te that direct spray,

spray drift, and runoff represen t potential transport mechanisms of oxyfluorfen to aquatic and

terrestrial organisms. Drinking water and inhala tion exposure pathways were screened using the

### 23 SIP (Screening Imbibition Program) and STIR (S creening Tool for Inhalation Risk) screening

methods and were found to be exposure pathwa ys of low concern (no LOC exceedances are

expected; see Appendix D ). SIP and STIR are described in detail at:

http://www.epa.gov/oppefed1/ models/terrestrial/index.htm . Oxyfluorfen is expected to

bioaccumulate in aquatic organisms, thus, the exposure pathway is complete for organisms that

feed on fish and other aquatic animals.



## 8 Analysis Plan

8.1 Stressors of Concern

8.1.1 Ecological Risk Assessment

The stressors of ecological concern for aqua tic organisms are oxyfluorfen and any major

degradates identified in the requested aquatic fa te studies. As a conservative estimate, the

unknown percentage(s) of the major degradate(s) will be treated as pare nt unless the amount(s)

of maximum formation are identif ied as a result of the data ca ll-in. Degradate MW-332, which

formed at >10% in the aquatic photolysis st udy (MRID 42129101), is estimated to be 3-4 times

less toxic than the parent ( Appendix E ). Additional information for the maximum formation of

MW-332 is needed to determine if it will be included or exclud ed in the Registration Review

ecological risk assessment.

The stressor of ecological concern for terrestrial organisms is oxyfluorfen.

8.1.2 Drinking Water Exposure Assessment

An EFED drinking water assessment was conducted fo r Oregon apples to establish tolerances of

oxyfluorfen for human health risk assessment (USEPA 2001; DP277546). Recommended

Estimated Drinking Water Concentrations (EDWCs ) were modeled for parent oxyfluorfen only.

The oxyfluorfen residues of c oncern may be reevaluated pend ing receipt and review of

additional environmental fate and toxicity data for oxyfluorfen and its potential degradates. The

drinking water assessment will be performed based on EFED’s current guidance using

appropriate surface and groundwater models. Descri ptions of all executable versions of current

models for drinking water exposure can be obtained from URL link:

http://www.epa.gov/oppefed1/models/water/

.

8.2 Measures of Exposure

EFED will use standard available models to evaluate potential exposures to aquatic and

terrestrial organisms, including bi oconcentration, as described at

http://www.epa.gov/pesticides/science/models_db.htm

.

8.2.1 Available Monitoring Data

The Agency is aware of monitoring conducted by federal and state agencies such as U.S.

Geological Survey (USGS) National Water Qu ality Assessment (NAWQA) Data Warehouse and

### 24 California Environmental Data Exchange Networ k (CEDEN). This rout e of exposure will be

considered in the assessment to the exte nt that data on oxyfl uorfen are available.

8.3 Measures of Effect

Toxicity data presented in Section 6 of this problem formulation w ill be used to calculate risk

quotients. The toxicity of oxyfluorfen is known to increase in the presence of UV light and will

be characterized in the risk assessment. According to the Agency’s website

http://www.epa.gov/sunwise/doc/uvradiation.html , factors to consider regarding the amount of

UV light are time of day, time of year, strato spheric ozone and weather (cloud cover). In

addition, for aquatic organisms, water depth and turbidity may al so affect UV penetration. An

LDPH adjustment factor (29x) will be applied to chronic fish endpoints, as support by submitted

data. Consistent with other LDPH chemical assessments, risks to other taxa will be

characterized.

Any additional information submitted by the registra nt or found in the open literature prior to

conducting the risk assessment will also be consider ed. The open literature studies are identified

using EPA’s ECOTOXicology database (ECOTOX) 3 

### , which employs a literature search engine

for locating chemical toxicity data for aquatic life , terrestrial plants, and wildlife. The evaluation

of both sources of data can also provide insight into the direct a nd indirect effects of pesticides

on biotic communities from loss of species that ar e sensitive to the chemicals and from changes

in structure and functional characteristics of the affected communities.

Consistent with the Agency’s responsibility under the Endangered Species Act (ESA), the

Agency will evaluate risks to federally listed th reatened and/or endangere d (listed) species from

registered uses of pesticides in Registration Re view. The process for eval uating potential risks to

listed species is further described at

http://www.epa.gov/oppfead1/enda nger/litstatus/riskasses.htm

.



## 9 Endocrine Disruptors Screening Program

Oxyfluorfen was not included in the first group of 67 chemicals issued an order to conduct Tier 1

EDSP testing. For additional info rmation the EDSP program, visit http://www.epa.gov/endo/

.



## 10 Preliminary Identification of Data Gaps

10.1 Environmental Fate

Table 11-1 identifies environmental fate studies by MRID that offer data for each guideline

requirement, as well as study clas sifications and whether or not further data are needed to

support the risk assessment.

3 http://cfpub.epa.gov/ecotox/

### 25 Table 10-1. Environmental Fate Data for Oxyfluorfen

OCSPP

Guideline Data

Requirement Submitte

d Studies

(MRID) Study

Classification Data

needed to

conduct

risk

assessment Justification

835.2120 Hydrolysis 0013 4454 Acceptable No --

835.2240 Aqueous

photolysis

(TGAI) 42142307

42142308

42129101 Supplemental Yes An aqueous photolysis study is

required under the 40 CFR Part 158.

Since this is a major degradation

pathway, a clarification is needed for

the % formation of degradates.

In absence of the complete degradate

data, a conservative approach will be

used by assuming the parent for those

degradates.

835.2410 Soil photolysis 4 1999901 Acceptable No --

835.4100 Aerobic soil

metabolism 42142309

46373103 Acceptable

Supplemental No --

835.4200 Anaerobic soil

metabolism 42142310 Supplemental No --

835.4300 Aerobic aquatic

metabolism

(TGAI) 46373104 Supplemental Yes An aerobic aquatic metabolism study

is required under the 40 CFR Part

158. The excessive nonextractable

residues (45.5 – 59.3%) needed to be

clarified

Unless registrant can characterize the

nonextractable residues, a

conservative approach will be used to

revisit the DT 50 by including

nonextractable residue.

835.4400 Anaerobic

aquatic

metabolism

(TGAI) No Data --- Yes Anaerobic soil metabolism data are

available

Data are required under 40 CFR Part

158. OCSPP guidance recommends

that these tests be performed with two

sediments. The assumption of

compound stability will be made in

the absence of acceptable data.

835.1230

835.1240 Adsorption/

desorption and

leaching 42142311 Supplemental No --

835.1410 Volatility –

laboratory No Data --- No Oxyfluorfen is not expected to be

volatile under normal use conditions

based on low vapor pressure and

Henry’s Law Constant

835.6100 Terrestrial field

dissipation 43840101 Supplemental No ---

### 26 OCSPP

Guideline Data

Requirement Submitte

d Studies

(MRID) Study

Classification Data

needed to

conduct

risk

assessment Justification

850-6100 ECM/ILV in soil

and water No data --- Yes Environmental chemistry method

(ECM) and independent laboratory

validation (ILV) are required under

the 40 CFR Part 158.

165-4

(850.1730) Fish

bioconcentration 00096883 Supplemental No ---



### Ecological Effects

Table 11-3 identifies ecological effects studies (by MRID) that offer data for each guideline

requirement, as well as study clas sifications and whether or not further data are needed to

support the risk assessment.

10.1.1 Justification for 10-day A dult Chronic Toxicity Study

Bees can be exposed to pesticides through multiple pathways including contact with sprays and

dusts and through ingestion of residues in food/water ( e.g ., pollen/nectar and water used to

maintain colony temperature). Worker bees fo raging on flowers for pollen and nectar can be

repeatedly exposed to residues in pollen and nectar through direct contamination of these

matrices by foliar sprays. Residues can in turn be brought back to bee colonies where in-hive

bees including young adult and developing brood ( i.e ., eggs, larvae and pupae) may be exposed.

EPA guidance (USEPA 2014) on assessing the risk of pes ticides to bees identifies a suite of

laboratory-based studies intended to serve as the foundation for sc reening chemicals for potential

acute and chronic exposure effects to individual adult and larval bees. The 10-day toxicity study

with young adult bees provides no-observed advers e effect level (NOAEL) and lowest-observed

adverse effect level (LOAEL) for assessing chronic effects. Data obtained from this study will be

used in estimating chronic risk to individual adult bees . This is a non-guid eline study; an OECD

protocol is expected to be available in Oct ober 2014. A protocol should be submitted to the

Agency for review before commencing the study and should include provisions for measuring

the concentration of oxyfluorfen in the actual diet of the honeybee.

10.1.2 Justification for 21-day Larval Toxicity Study

Developing bee brood ( i.e ., larvae and pupae) can be exposed to pesticides through residues

brought back to the colony by worker bees fora ging in areas where th e pesticide has been

applied. While larvae are typically fed roya l or brood jelly during th eir early stages of

development, worker bee (females) and drone (males) larvae are also fed pollen/honey (bee

bread) directly by in-hive nurse bees. EPA guidance (USEPA 2014) on assessing the risk of

pesticides to bees identifies a suite of laboratory-based studies intended to serve as the

foundation for screening chemicals for potential acute and chronic effects to individual adult and

larval bees. The 21-day larval toxicity study under developmen t by OECD provides both acute

and chronic toxicity data on developing bee br ood and will yield a median lethal dose (LD 50 

### ) for

assessing acute toxicity during the early part of the study as well as a 21-day no-observed

adverse effect level (NOAEL) a nd lowest-observed adverse effect level (LOAEL) for assessing

### 27 chronic effects. Alternativel y, registrants may submit a separa te acute (single dose) larval

toxicity study following OECD Gu ideline 237 as well as the 21-day repeat dose chronic toxicity

study to address both acute and ch ronic larval endpoints. Effects on survival and development

(adult bee emergence) from repeat exposures to th e active ingredient will be used in estimating

chronic risk to individual brood. A protocol for the 21-day larv al toxicity test should be

submitted to the Agency for review before co mmencing the study and should include provisions

for measuring the concentrati on of oxyfluorfen in the actu al diet of the honeybee.

________________________________________________ Draft guidance for the 21-day larval toxicity study is available at:

http://www.oecd.org/env/ehs/testing/Draft_GD_h oneybees_rep_exp_for_2nd_CR_25_November_2013.pdf

OECD Guideline 237 is available at: http://www.oecdilibrary.org/docserver/download/9 713171e.pdf?expires=14 07449911&id=id&accname=guest&checksum=E67BED

EB01DB12D815E858CB45A989FB28Table 11-3. Ecological Effects Data for OxyfluorfenOCSPPGuidelineDataRequirementSubmitted Study(MRID)ClassificationAre dataneeded toconduct the riskassessment?Justification and Assumptions EPA Will Make in theAbsence of DataAvian Testing850.2100 Avian oraltoxicity92136102 (upland game) AcceptableYesAcute oral toxicity data for a passerine species are requiredunder the new 40 CFR Part 158. A study has not beensubmitted for this data requirement.A guideline-compliant passerine acute oral toxicity test isneeded. Acute oral toxicity data are only available for oneavian species (i.e., bobwhite quail). Passerine birds mayutilize metabolic pathways that are different from larger birdsand therefore be more sensitive to oxyfluorfen. Furthermore,passerines exhibit behavioral responses to pesticide dosingthat are potential indicators of reduced fitness in the field(e.g., regurgitation of contaminated diet) even when directbiochemically-mediated lethal toxicity is not apparent.In the absence of these data, passerine toxicity data forsurrogate pesticides – starting with data for closely relatedpesticides (e.g., diphenyl ethers) and proceeding to data forless related pesticides – may be used to characterize the acutetoxicity of oxyfluorfen to passerine species.No data (passerine species) NA850.2200 Avian dietarytoxicity92136104 (waterfowl) Acceptable No --92136103 (upland game) Acceptable850.2300 Avianreproduction46070102 (upland game) Acceptable No --46070101 (waterfowl) AcceptableInsect Pollinator Testing850.3020 Honey bee acutecontact toxicity42368101 Acceptable No --Specialstudy(OECD213)Acute oraltoxicity to adulthoney beesNo data NA YesGuidance for assessing pesticide risks to bees (USEPA, 2014)recommends requesting the following Tier I special studies:Acute oral toxicity to adult honey bees29OCSPPGuidelineDataRequirementSubmitted Study(MRID)ClassificationAre dataneeded toconduct the riskassessment?Justification and Assumptions EPA Will Make in theAbsence of DataSpecialstudyChronic oraltoxicity to adulthoney beesNo data NA YesAcute oral toxicity to larval honey beesChronic oral toxicity to adult honey beesChronic oral toxicity to larval honey beesIn the absence of these data, honey bee oral toxicity data forsurrogate pesticides – starting with data for closely relatedpesticides (e.g., diphenyl ethers) and proceeding to data forless related pesticides – may be used to characterize the oraltoxicity of oxyfluorfen to larval and adult honey bees.Tier II (feeding/semi-field/pollenand nectar residue) and TierIII (full field) studies may be needed, contingent upon theresults of lower tier studies.SpecialstudyAcute andchronic oraltoxicity to larvalhoney beesNo data NA YesSpecialstudyPollinatorfeeding/semifield/pollen andnectar residuestudiesNo data NA Need for datacontingent uponresults of Tier Ibee studies850.3040 Field testing forpollinatorsNo data NA Need for datacontingent uponresults of Tier Ibee studiesAquatic Organisms Testing850.1010 Freshwaterinvertebrateacute toxicity00134449 Acceptable No --45217301 Supplemental850.1025850.1035850.1045850.1055Saltwaterinvertebrateacute toxicity00134451 and 30971107(shrimp)Supplemental No Although the submitted study with grass shrimp wasclassified asSupplementaldue to guideline deviations, it isdeemed sufficient for quantitative use in the ecological riskassessment.42378901 (mollusc)Acceptable No --850.1075 Freshwater fishacute toxicity00081856 (warm water) AcceptableYesThe submitted acute test with sheepshead minnow (MRID41698801) was downgraded from “acceptable” to“supplemental” due to considerable uncertainty regarding theexposure concentrations. Measured test concentrations forthe nominal 60 and 100 mg/L treatment levels declined from0.16 and 0.28 mg/L at 0 hours to 0.06 and 0.06 mg/L at 96hours, respectively. The most sensitive LC50for freshwaterfish is 0.200 mg/L. This suggests that not maintaining stableconcentrations over the test period may have resulted in an42129801 (warm water) Acceptable00134448 (warm water) Acceptable42129802 (cold water) Acceptable00081856 (cold water) Acceptable850.1075 Saltwater fishacute toxicity41698801 Supplemental30OCSPPGuidelineDataRequirementSubmitted Study(MRID)ClassificationAre dataneeded toconduct the riskassessment?Justification and Assumptions EPA Will Make in theAbsence of Dataunderestimation of toxicity. Furthermore, there wereexceedances for freshwater fish in previous assessments.It should be noted that an acute toxicity endpoint forestuarine/marine fish cannotbe estimated using an acute-tochronic ratio (ACR) for freshwater fish (provided the chronicendpoint generated from the requested estuarine/marine fishearly life stage test [OCSPP 850.1400] is deemed sufficientfor quantitative use in the ecological risk assessment) becausethe available freshwater fish chronic toxicity endpoints weregenerated for fathead minnow, a species for which we do nothave an acute toxicity endpoint.Therefore, an acute test withfathead minnow or a repeatacute test with an estuarine/marine fish is recommended.In the absence of these data,estuarine/marine fish acutetoxicity data for surrogate pesticides – starting with data forclosely related pesticides (e.g., diphenyl ethers) andproceeding to data for less related pesticides – may be used tocharacterize the acute toxicity of oxyfluorfen toestuarine/marine fish.850.1300 Freshwaterinvertebratelife cycle45550201, 92136106, and42142305Acceptable No --850.1350 Saltwaterinvertebrateslife cycle46597701 Supplemental No Although the submitted study with mysid shrimp is classifiedasSupplementaldue to guideline deviations, it is sufficientfor quantitative use in the ecological risk assessment.850.1400 Freshwater fishearly life stage00099270, 00030249, and92136057 (standard lighting)Acceptable No --46585104 (UV lighting) Acceptable850.1400 Saltwater fishearly life stageNo data NA YesThis study was identified as a data gap in the RED, and asubsequent DCI for this study was issued. The studysubmitted in response to the DCI (MRID 46794501) wasclassified asInvaliddue to low hatching success in thecontrols and high variability in measured test concentrations.31OCSPPGuidelineDataRequirementSubmitted Study(MRID)ClassificationAre dataneeded toconduct the riskassessment?Justification and Assumptions EPA Will Make in theAbsence of DataA guideline-compliant early life stage test with anestuarine/marine species is needed.In the absence of these data,estuarine/marine fish chronictoxicity data for surrogate pesticides – starting with data forclosely related pesticides (e.g., diphenyl ethers) andproceeding to data for less related pesticides – may be used tocharacterize the chronic toxicity of oxyfluorfen toestuarine/marine fish.850.1735 Whole sediment:acute freshwaterinvertebrates46585102 Supplemental No Although the submitted study withC. tentansis classified asSupplementaldue to lower than recommended lightintensity, it is sufficient for quantitative use in the ecologicalrisk assessment.850.1470 Whole sediment:acute marineinvertebrates46585103 Supplemental No Although the submitted study withL. plumulosusis classifiedasSupplementaldue to uncertain exposure concentrationsand not using continuous lighting per the guideline, it issufficient for quantitative use in the ecological riskassessment.Nontarget area phytotoxicity testing850.4100 Seedlingemergence andseedling growth45861101 Acceptable No --850.4150 Vegetative vigor 45861102 Acceptable No --850.4400 Aquatic planttest usingLemnaspp.45861103 Supplemental No Although the submitted study withL. gibbais classified asSupplementaldue to uncertain exposure concentrations, it issufficient for quantitative use in the risk assessment.850.4500 Algal toxicity45271302 (greenalga) AcceptableNo Although the submitted studies with freshwater and marinediatoms,N. pelliculosaandS. costatum, respectively, areclassified asSupplementaldue to uncertain exposureconcentrations, they are sufficient for quantitative use in theecological risk assessment.45861105 (freshwater diatom) Supplemental45861106 (marine diatom) Supplemental850.4550 Cyanobacteriatoxicity45861104 Supplemental No Although the submitted studies withA. flos-aquaeisclassified asSupplementaldue to uncertain exposureconcentrations, it is sufficient for quantitative use in theecological risk assessment.Abbreviations: NA = not applicable

### 32 

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42142309 Korsch, B.; Doran, T. (1988) Aerobi c Soil Metabolism of Oxyfluor- fen:

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### 34 46373104 Mamouni, A. (2002) (Carbon-14)-Oxyfluor fen: Route and Rate Degradation

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00081856

00038574 Bentley, R.E. (1973) Acute Toxicity of RH-2915 to Bluegill (Lepomis

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### 35 (Unpublished study received Mar 8, 1978 under 707-142; prepared by Union

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42142302

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42142303

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42255901

92136102 Fletcher, D. (1987) 21-Day Acute Oral Toxicity Study with Goal Technical

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42368101 Atkins, E. (1992) Bee Adult Toxi city Dusting Test Evaluating the

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45271302 Sutherland, C.; Kendall, T.; Krueger, H. (2000) Goal 2XL (P) Herbicide: A

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45271303 Milligan, D. (2000) Goal 4F (AKA Goal 480 SC) Herbicide: Laboratory

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42378901 Graves, W. (1992) Goal Technical Herbicide: A 96-Hour Shell Deposition

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45550201 Forbis, A.; Fraxier, S. (2001) Goal Technical Herbicide (RH-2915): Acute

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45581601 Hoberg, J. (1999) Goal Technical Pu rified Herbicide --Toxicity to the

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45861101 Aufderheide, J. (2002) Effects of Oxyfluorfen on Seedling Emergence and

Growth of Selected Non-Target Terrestr ial Plants (Tiers 1 and II): Lab Project

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Inc. 124 p.

### 37 45861102 Aufderheide, J. (2002) Effects of Ox yfluorfen on the Vegetative Vigor of

Non-Target Terrestrial Plants (Tiers 1 & II): Lab Pr oject Number: 47454:

021307. Unpublished study prepared by A BC Laboratories, Inc. 111 p.

45861103 Roshon, R. (2002) Oxyfluorfen (Goal) : Growth Inhibiti on Test with the

Freshwater Aquatic Plant, Lemna gibba L.G3: Final Study: Lab Project

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45861104 Roshon, R. (2002) Oxyfluorfen (Goal) : Growth Inhibiti on Test with the

Freshwater Bluegreen Alga, Anabaena flos-aquae : Final Study Report: Lab

Project Number: S2310-01: 4686: 021019. Unpublished study prepared by

ESG International Inc. 125 p. {OPPTS 850.5400}

45861105 Roshon, R. (2002) Oxyfluorfen (Goal) : Growth Inhibiti on Test with the

Freshwater Diatom, Navicula pelliculosa : Final Study Report: Lab Project

Number: S2310-02: 4686: 021020. Unpub lished study prepared by ESG

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45861106 Roshon, R. (2002) Oxyfluorfen (Goal) : Growth Inhibiti on Test with the

Marine Diatom Skeletonema costatum : Final Study Report: Lab Project

Number: S2310-03: 4686: 021021. Unpub lished study prepared by ESG

International Inc. 105 p. {OPPTS 850.5400}

45906008 Sutherland, C.; Kendall, T.; Kruege r, H. (2000) MON 78095: A 96-Hour

Toxicity Test with the Freshwater Alga ( Selenastrum capricornutum ): Final

Report: Lab Project Number: 129A-1 79: 00RC-0045: 00P-045. Unpublished

study prepared by Wildlife Inte rnational, Ltd. 98 p. {OPPTS 850.5400}

45906003 Nienstedt, K. (1999) Goal 2XL (P): La boratory Acute Toxici ty Test with the

Parasitic Wasp, Aphidius rhopalosiphi (Hymenoptera: Aphididae): Final

Report: Lab Project Number: 98RC-0086: 98-086-1007: 1007.039.270.

Unpublished study prepared by Springborn Laboratories (Europe) Ag. 52 p.

45906004 Nienstedt, K. (1999) Goal 2XL (P): La boratory Acute Toxici ty Test with the

Ground Beetle Poecilus cupreus L. (Coleoptera: Cara bidae): Final Report:

Lab Project Number: 98-088- 1007: 98RC-0084: 1007.039.267. Unpublished

study prepared by Springborn Labor atories (Europe) Ag. 59 p.

45906005 Nienstedt, K. (1999) Goal 2XL (P): La boratory Toxicity Test with Spiders,

Pardosa sp. (Araneae: Lycosidae): Fina l Report: Lab Project Number: 98-

087-1007: 98RC-0083: 1007.039.272. Unpublished study prepared by

Springborn Laboratories (Europe) Ag. 58 p.

45906006 Nienstedt, K. (1999) Goal 2XL (P): La boratory Contact Toxicity Test with the

Predacious Mite, Typhlodromus pyri Scheuten (Acari: Phytoseiidae): Final

Report: Lab Project Number : 98-085-1007: 98RC-0085: 1007.039.268.

Unpublished study prepared by Springborn Laboratories (Europe) Ag. 63 p.

### 38 45906007 Nienstedt, K. (1999) Goal 2XL (P): A 14-Day Acute Toxicity Test with the

Earthworm ( Eisenia foetida ): Final Report: Lab Project Number: 98-089-

1007: 98RC-0087: 1007.039.630. Unpublished study prepared by Springborn

Laboratories (Europe) Ag. 75 p.

46070101 Frey, L.; Martin, K.; Beavers, J.; et . al. (2003) Oxyfluorfen: A Reproduction

Study with the Mallard: Final Report. Project Number: 379/128. Unpublished

study prepared by Wildlife International, Ltd. 188 p.

46070102 Frey, L.; Martin, K.; Beavers, J.; et . al. (2003) Oxyfluorfen: A Reproduction

Study with the Northern Bobwhite: Fi nal Report. Projec t Number: 379/127,

021017. Unpublished study prepared by W ildlife International, Ltd. 189 p.

46585102 Palmer, S.; Thomas, S.; Kendall, T.; et . al. (2005) Oxyfluorfen: A Survival

and Growth Sediment Toxicity Test with Chironomus tentans Using Spiked

Sediment. Project Number: 040438, 379A /112. Unpublished study prepared

by Wildlife International, Ltd. 89 p.

.

46585103 Palmer, S.; Thomas, S.; Kendall, T.; et. al. (2005) Oxyf luorfen: A 10-Day

Sediment Toxicity Test with Leptocheirus plumulosus Using Spiked

Sediment. Project Number: 379A/113 A, 040439. Unpublished study prepared

by Wildlife International, Ltd. 84 p.

46585104 Palmer, S.; Kendall, T.; Krueger, H. (2005) Oxyfluorfen: An Early Life-Stage

Toxicity Test with the Fathead Minnow ( Pimephales promelas ) Under

Ultraviolet Light Conditions. Project Number: 379A/114, 040442.

Unpublished study prepared by Wildlife International, Ltd. 127 p.

46597701 Blankinship, A.; Kendall, T.; Kruege r, H. (2005) Oxyfluorfen: A FlowThrough Life-Cycle Toxicity Test with the Saltwater Mysid ( Mysidopsis

bahia ). Project Number: 379A/110A, 040441. Unpublished study prepared by

Wildlife International, Ltd. 91 p.

### 39 

## Appendix A: Application Information by Use for Oxyfluorfen

Use Method of Application Maximum Application Rate (Minimum

Application Interval) 1

Terrestrial Food

Apricot Broadcast 6 2 apps at 0.2436 lb ai/A –yearly max not specified

Chemigation, direct spray 6 2 apps at 0.2539 lb ai/A –yearly max not specified

Artichoke Direct spray 1 2 app of 1.522 lb ai/A –yearly max not specified

Avocado Band treatment 1 2 app of 2.040 lb ai/A –yearly max not specified

Chemigation, direct spray 1 2,3 app of 1.530 lb ai/A

Blackberry Band treatment, broadcast 2 apps at 1.015 lb ai/A

Broccoli, Cabbage, Cauliflower Broadcast 1 2 app at 0.5099 lb ai/A –yearly max not specified

Direct spray 1 2 app at 0.5078 lb ai/A –yearly max not specified

Cocoa Broadcast 6 3 apps at 1.020 lb ai/A

Direct spray 3 3 apps at 2.040 lb ai/A

Coffee Broadcast, direct spray 3 3 apps at 2.040 lb ai/A

Date, Feijoa (pineapple guava),

Fig, Kiwi fruit, Olive,

Persimmon, Pistachio,

pomegranate, Walnut

(English/black) Band Treatment 1 2 app at 2.040 lb ai/A –yearly max not specified

Chemigation, direct spray 1 2,3 app at 1.530 lb ai/A

Garlic Broadcast 1 2 app at 0.5099 lb ai/A –yearly max not specified

Chemigation, direct spray 2 2 apps at 0.2550 lb ai/A –yearly max not specified

Guava Direct spray 2 2 apps at 2.040 lb ai/A –yearly max not specified

Horseradish Broadcast, direct spray 1 2 app at 0.5099 lb ai/A –yearly max not specified

Nectarine, Peach, Plum, Prune Broadcast, chemigation, direct

spray 6 2 apps at 0.2436 lb ai/A –yearly max not specified

Olive Broadcast 6 2 apps at 0.2436 lb ai/A –yearly max not specified

Onion Band treatment, broadcast 1 2 app at 0.5099 lb ai/A –yearly max not specified

Chemigation 2 2 apps at 0.2550 lb ai/A –yearly max not specified

Direct spray 2 2 apps at 0.1912 lb ai/A –yearly max not specified

Papaya Direct spray 3 3 apps at 1.020 lb ai/A

Raspberry (black, red) Band treatment, broadcast 1 2 app at 0.7610 lb ai/A –yearly max not specified

Sage, clary Broadcast 6 3 apps at 0.2550 lb ai/A

Taro Band treatment, direct spray 6 3 apps at 0.2550 lb ai/A

Broadcast 2 2 apps at 0.5099 lb ai/A –yearly max not specified

Terrestrial Non-Food

Agricultural fallow/idleland/

conservation reserve Broadcast 1 2 app at 0.5099 lbs ai/A –yearly max not specified

Agricultural uncultivated areas Broadcast NS apps at 2.040 lbs ai/A 4

Christmas tree plantations Broadcast 2 apps at 2 lbs ai/A (2 months)

Direct spray 2 3 apps at 2.031 lb ai/A

Citrus Direct spray 1 2 app at 1.530 lbs ai/A –yearly max not specified

Clover Broadcast 1 2 app at 0.0951 lbs ai/A –yearly max not specified

Cocoa Broadcast 6 3 apps at 1.020 lb ai/A

Direct spray 3 3 apps at 2.040 lb ai/A

Coffee Broadcast, direct spray 3 3 apps at 2.040 lb ai/A

Conifers (plantations/nurseries) Broadcast 2 apps at 2 lbs ai/A (2 months)

Chemigation NS apps at 1.001 lb ai/A 4

Deciduous trees Broadcast 1 2 app at 2.029 lb ai/A –yearly max not specified

Direct spray, spot soil treatment 1 3 app at 1.530 lb ai/A

Spray 3 3 apps at 1.570 lb ai/A

### 40 Use Method of Application Maximum Application Rate (Minimum

Application Interval) 1

Eucalyptus Broadcast, direct spray 3 3 apps at 1.530 lb ai/A

Grapes Broadcast, direct spray 1 2 app of 2.031 lb ai/A –yearly max not specified

Grasses grown for seed Broadcast 1 2 app of 0.3808 lb ai/A –yearly max not specified

Guava Direct spray 2 2 apps at 2.040 lb ai/A –yearly max not specified

Jojoba Direct spray 1 3 app at 1.530 lb ai/A

Lesquerella Broadcast NS apps at 0.5233 lb ai/A 4

Nonagricultural uncultivated

areas/soils Broadcast NS apps at 2.040 lb ai/A 4

Spray, sprinkle NS apps at 4.530 lb ai/A 4

Nursery stock Broadcast NS apps at 2.003 lb ai/A (60 days)

Soil broadcast treatment 3 2 apps at 2 lb ai/A –yearly max not specified

Onion Broadcast, chemigation 4 2 apps at 0.1275 lb ai/A –yearly max not specified

Ornamental and/or shade trees Spray, sprinkle NS apps at 4.530 lb ai/A 4

Ornamental woody shrubs and

vines Spray, sprinkle NS apps at 4.530 lb ai/A 4

Ornamentals (unspecified) Broadcast, soil broadcast

treatment 3 2 apps at 2.003 lb ai/A (60 days) –yearly max not

specified

Spray 2 apps at 1.921 lb ai/A (3 months)

Pineapple Band Treatment, broadcast,

direct spray NS apps at 2.040 lb ai/A

Rose Direct spray 2 2 apps at 1.016 lb ai/A –yearly max not specified

Sweet peas (ornamental) Broadcast NS apps at 0.2537 lb ai/A 4

Tree nuts Band Treatment 1 2 app at 2.040 lb ai/A –yearly max not specified

Chemigation, direct spray 1 2,3 app at 1.530 lb ai/A

Terrestrial Food + Feed

Agricultural fallow/idleland/

conservation reserve Band treatment, broadcast 1 2 app at 0.5099 lbs ai/A –yearly max not specified

Spray 1 2 app at 0.5073 lbs ai/A –yearly max not specified

Almond, Stone fruits Band Treatment 1 2 app at 2.040 lbs ai/A –yearly max not specified

Chemigation, direct spray 1 2 app at 1.530 lbs ai/A –yearly max not specified

Corn (unspecified) Broadcast 1 2 app at 0.5233 lbs ai/A –yearly max not specified

Direct spray 1 2 app at 0.7850 lbs ai/A –yearly max not specified

Corn, field Broadcast 1 2 app at 0.5078 lbs ai/A –yearly max not specified

Direct spray 1 2 app at 0.7649 lbs ai/A –yearly max not specified

Cotton (unspecified) Band treatment 2 2 apps at 0.5099 lbs ai/A –yearly max not

specified

Direct spray 2 2 apps at 0.5100 lbs ai/A –yearly max not

specified

Garbanzos (including chick peas) Broadcast 6 3 apps at 0.2539 lbs ai/A

Grapes, Pome fruits Band treatment 1 2 app at 2.040 lbs ai/A –yearly max not specified

Chemigation, direct spray 1 2,3 app at 1.530 lbs ai/A

Mint/peppermint/spearmint,

Peppermint Broadcast 1 app at 1.530 lbs ai/A

Soybeans (unspecified) Broadcast 2 apps at 0.5099 lbs ai/A

Conservation tillage 2 apps at 0.7649 lbs ai/A

Direct spray 1 2 - 3 3 apps at 0.5078 lbs ai/A

Tree nuts Band treatment 1 2 app at 2.031 lbs ai/A –yearly max not specified

Chemigation, direct spray 1 2 app at 1.523 lbs ai/A –yearly max not specified

### 41 Use Method of Application Maximum Application Rate (Minimum

Application Interval) 1

Forestry

Cottonwood (Forest/Shelterbelt) Direct spray 3 2 apps at 1.53 lbs ai/A –yearly max not specified

Forest Trees (Softwoods Conifers ) Direct spray 2 2 apps at 2.04 lbs ai/A –yearly max not specified

Chemigation 2 2 apps at 1.02 lbs ai/A –yearly max not specified

Shelterbelt Plantings Band treatment, broadcast, direct

spray 3 2 apps at 1.53 lbs ai/A –yearly max not specified

Terrestrial Non-Food + Outdoor Residential

Rose Direct spray 2 2 apps at 1.01 lbs ai/A –yearly max not specified

NS – not specified on the label

1 Minimum application interval was not specified unless otherwise noted.

2 Number of applications assumed, based on the crop cycle maximum application rate.

3 Number of applications assumed, based on the yearly maximum application rate.

4 Identified as a gap in label information by BEAD.42Appendix B: Summary of Endpoints from Oxyfluorfen Toxicity StudiesStudy TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationAvian acute oral:single dose, 21-dayobservation (insteadof usual 14-dayobservation)Oxyfluorfentechnical(70.2)Bobwhite quail(Colinus virginianus)LD50> 2150 mg/kg-bw (nom)NOAEL < 1470 mg a.i./kg-bw (nom)(1 mortality at 2150 mg /kg-bw; sublethal effects: weakness,anorexia, piloerection, and abnormal cage droppings at 1470 and2150 mg/kg-bw, recovery by day 7; food consumption severelydepressed at 1470 and 2150 mg/kg-bw during first 2 and 7 daysrespectively; weight loss at 1470 and 2150 mg/kg-bw during first3 days)Practically non-toxicMRIDs 92136102,42255901, and42142301AcceptableAvian acute oral NA Passerine species No data NAAvian sub-acutedietary: 5-dayexposure; 3-daypost-exposureobservationOxyfluorfentechnical(70.2)Mallard duck(Anas platyrhynchos)LC50> 5000 mg a.i./kg-diet (nom)NOAEC = 312 mg a.i./kg-diet (nom)LOAEC = 625 mg a.i./kg-diet (nom)(10% [1/10] mortality at 5000 mg/kg-diet; sublethal effects:anorexia at 5000 mg/kg-diet on days 2-3; concentrationdependent reduction in food consumption at≥625 mg/kg-dietduring exposure period; reduction in food consumption at allreatment levels on days 6-8; NOAEC based on reduction in foodconsumption)Practically non-toxicMRIDs 92136104and 42142303AcceptableOxyfluorfentechnical(70.2)Bobwhite quail(Colinus virginianus)LC50> 5000 mg a.i./kg-diet (nom)NOAEC = 625 mg a.i./kg-diet (nom)LOAEC = 1250 mg a.i./kg-diet (nom)(no mortality; sublethal effects: reduction in body weight gainsat 1250 and 2500 mg/kg-diet during days 0-5; body wieght loo at5000 mg/kg-diet by day 5; food avoidance during days 3-5 andreduction in food consumption durings days 0-5 at 2500 and5000 mg/kg-diet; NOAEC based on reduction in body weightgain)Practically non-toxicMRIDs 92136103and 42142302AcceptableAvian reproduction:21 weeks (chronic)Oxyfluorfen (72.5) Mallard duck(Anas platyrhynchos)NOAEC = 100 mg/kg-diet (nom)LOAEC > 100 mg/kg-diet (nom)MRID 415301205Supplemental43Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassification(only 1 testconcentration)Avian reproduction:22 weeks (chronic)Oxyfluorfen (72.5) Bobwhite quail(Colinus virginianus)NOAEC < 50 mg/kg-diet (nom)LOAEC = 50 mg/kg-diet (nom)(based on reduced body weights of 14-day chicks)MRIDs 00110735& 00117619Supplemental(no NOAECestablished)Avian reproduction:20 weeks(chronic)Oxyfluorfentechnical, purified(99.3)Bobwhite quail(Colinus virginianus)NOAEC = 124 mg a.i./kg-diet (mm)LOAEC = 256 mg a.i./kg-diet (mm)(based on most sensitive parameter of survivor weight; ratio ofhatchling survival to number of hatchlings, viable embryos, liveembryos, number of hatchlings, ratio of eggs set to eggs laid, andratio of number of hatchlings to eggs laid, ratio of hatchlingsurvival to eggs set also affected)MRID 46070102AcceptableAvian reproduction:20 weeks(chronic)Oxyfluorfentechnical, purified(99.3)Mallard duck(Anas platyrhynchos)NOAEC = 506 mg a.i./kg-diet (mm)LOAEC = 751 mg a.i./kg-diet (mm)(based on eggs laid, eggs set, viable embryos, the ratio of viableembryos to eggs set, live embryos, number of hatchlings, theratios of normal hatchlings to eggs laid and to eggs set, andhatchling survival)MRIDs 46070101AcceptableMammalian acuteoral, limit: singledose; 14-dayobservationOxyfluorfen(96)Rat(Rattus norvegicus)LD50> 5,000 mg a.i./kg-bw(no effects)Practically non-toxicMRID 44712010AcceptableMammalian acuteoral, limit: singledose; 14-dayobservationOxyfluorfentechnical 95(97.1)Rat(Rattus norvegicus)LD50> 5,000 mg a.i./kg-bw(no effects)Practically non-toxicMRID 44828903AcceptableMammalian acuteinhalationOxyfluorfen(96)Rat(Rattus norvegicus)LC50> 3.71 mg/L MRID 44712012Mammalian 2-generationreproduction(chronic)Oxyfluorfen Rat(Rattus norvegicus)ParentalNOAEC = 400 mg a.i./kg-dietLOAEC = 1600 mg a.i./kg-diet(based on parental effects including mortality, decreased bodyweight, liver and kidney histopathology)ReproductiveNOAEC = 400 mg a.i./kg-dietMRID 42014901Acceptable44Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationLOAEC = 1600 mg a.i./kg-diet(based on decreased body weight and decreased live pups/litter)Acute contact withadult honey bees:single dose, 96-hourobservationOxyfluorfentechnical(71.4)Adult honey bee(Apis mellifera)LD50> 100 μg a.i./bee (nom)NOAEL: Not specified(4-5% mortality across control and 3 treatment concentrations)Practically non-toxicMRID 42368101AcceptableAcute oral withhoney bee adultsNA Adult honey bee No data NAAcute oral withhoney bee larvaeNA Larval honey bee No data NAChronic oral withhoney bee adultsNA Adult honey bee No data NAChronic oral withhoney bee larvaeNA Larval honey bee No data NATerrestrialinvertebrateGoal 4F Herbicide(aka Goal 480 SC)(42.09)Predacious mite(Typhlodromus pyri)7-day mortality = 98% at 1.28 lba.i./A compared to controlmortality of 5%MRID 45271303Supplemental(not a guidelinestudy)Goal 2XL(22.26)Parasitic wasp(Aphidus rhopalosiphi)24-hour mortality = 100% at 1.29 lb a.i./A (5.80 lb Goal 2-XL/A) compared to no control mortalityMRID 45906003Supplemental(not a guidelinestudy)Goal 2XL(22.26)Ground beetle(Poecilus cupreusL.)No effects after 21 days at 1.29 lb a.i./A (5.80 lb Goal 2-XL/A) MRID 45906004Supplemental(not a guidelinestudy)Goal 2XL(22.26)Spider(Paradosasp.)24-hour mortality = 100% at 1.08 lb a.i./A (4.86 lb Goal 2-XL/A) compared to no control mortalityMRID 45906005Supplemental(not a guidelinestudy)Goal 2XL(22.26)Predacious mite(Typhlodromus pyri)7-day mortality = 100% at 1.29 lb a.i./A (5.80 lb Goal 2-XL/A)compared to control mortality of 2%MRID 45906006Supplemental(not a guidelinestudy)Goal 2XL (P)(22.26)Earthworm(Eisenia foetida)14-day LC50(95% C.I.) = 89 (79-100) mg a.i./kg-dry soil (400[356.6-447.6] mg Goal 2-XL/kg-dry soil) (nom)MRID 45906007Supplemental45Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationProbit slope (95% C.I.) = 7.20 (5.03-9.36)14-day NOAEC = 29 mg a.i./kg-dry soil (125 mg Goal 2-XL/kgdry soil) (nom)14-day LOAEC = 56 mg a.i./kg-dry soil (250 mg Goal 2-XL/kgdry soil) (nom)(NOAEC based on reductions in growth)(not a guidelinestudy)Terrestrial plantseedling emergence:14 daysOxyfluorfentechnical(71.5)Most sensitivemonocot: RyegrassEC25= 0.0058 lb a.i./ANOAEC = 0.0024 lb a.i./A(based on length)MRID 41644001Supplemental(percent recoverywas unacceptablyhigh for twotreatmentlevels)Most sensitive dicot:CabbageEC25= 0.0026 lb a.i./ANOAEC = 0.0024 lb a.i./A(based on length)Terrestrial plantvegetative vigor:14 daysOxyfluorfentechnical(71.5)Most sensitivemonocot: OnionEC25= 0.0062 lb a.i./ANOAEC = 0.0071 lb a.i./A(based on weight)MRID 41644001Supplemental(NOAEC and EC25for cabbage areunacceptable;percent recoverywas unacceptablylow for twotreatment levels;solvent control wascontaminated withthe test substance)Most sensitive dicot:TomatoEC25= 0.00043 lb a.i./ANOAEC = 0.00066 lb a.i./A(based on weight)Terrestrial plantseedling emergence:minimum of 14 daysafter 50% of thecontrol plants hademergedGoal 2XL(23.1)Most sensitivemonocot: RyegrassEC25= 0.0063 lb a.i./A (nom)EC05= 0.00065 lb a.i./A (nom)NOAEC = 0.030 lb a.i./A (nom)Note: Since the NOAEC > EC25, the EC05will be used forassessing risk to listed species.(based on dry weight)MRID 45861101AcceptableMost sensitive dicot:LettuceEC25= 0.0072 lb a.i./A (nom)EC05= 0.0024 lb a.i./A (nom)NOAEC = 0.0080 lb a.i./A (nom)Note: Since the NOAEC > EC25, the EC05will be used forassessing risk to listed species.(based on dry weight)46Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationTerrestrial plantvegetative vigor:22-23 daysGoal 2XL(23.1)Most sensitivemonocot: OatEC25= 0.27 lb a.i./A (nom)EC05= 0.08 lb a.i./A (nom)NOAEC = 0.22 lb a.i./A (nom)(based on dry weight)MRID 45861102AcceptableMost sensitive dicot:LettuceEC25= 0.0078 lb a.i./A (nom)EC05= 0.00032 lb a.i./A (nom)NOAEC = 0.000035 lb a.i./A (nom)(based on dry weight)Freshwater fishacute: 96 hours,flow-through,standard laboratorylightingOxyfluorfen(94)Bluegill sunfish(Lepomismacrochirus)LC50(95% C.I.) = 200 (130-310) μg/L (nom)NOAEC: Not specified(no mortality at lowest test concentration, 56 μg/L; sublethaleffects: darkening, lethargy, and loss of equilibrium)Highly toxicMRIDs 00081856and 00038574AcceptableFreshwater fishacute: enhanced UVlightingOxyfluorfen Bluegill sunfish(Lepomismacrochirus)Estimated LC50= LC50(bluegill sunfish)/Ratio(standard lighting: enhanced UV lighting)= 200 μg/L/29.2= 7 μg/LWhere:Ratio(standard lighting: enhanced UV lighting)= NOAEC(fathead minnow ELS, standard lighting)/NOAEC(fathead minnow ELS,enhanced UV lighting)= 38 μg/L/1.3 μg/L= 29.2NAFreshwater fishacute: 96 hours,staticOxyfluorfentechnical(71.4)Bluegill sunfish(Lepomis macrochirus)LC50(95% C.I.) = 210 (175-346) μg a.i./L (mm)NOAEC = 93 μg a.i./L (mm)LOAEC = 175 μg a.i./L (mm)(NOAEC based on mortalityand sublethal effects at≥175 μg/L;no mortality or sublethal effects at 29-93 μg/L; sublethal effects:hyperexcitability in surviving fish at 175 μg/L)Highly toxicMRID 42129801AcceptableFreshwater fishacute: 96 hours,staticOxyfluorfentechnical(71.4)Rainbow trout(Oncorhynchusmykiss)LC50(95% C.I.) = 253 (186-355) μg a.i./L (mm)Probit slope (95% C.I.) = 2.4 (1.6-3.1)NOAEC = 37 μg a.i./L (mm)LOAEC = 83 μg a.i./L (mm)MRID 42129802Acceptable47Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassification(NOAEC based on mortalityand sublethal effects at≥83 μg/L;no mortality or sublethal effects at 37 μg/L; sublethal effects:lethargy in surviving fish at 398 and 1090 μg/L)Highly toxicFreshwater fishacute: 96 hours,staticOxyfluorfen (74) Channel catfish(Ictalurus punctatus)LC50(95% C.I.) = 400 (360-450) μg/L (nom)NOAEC: Not specified(sublethal effects: erratic swimming behavior and mucousshedding at≥320 μg/L)Highly toxicMRID 00134448AcceptableFreshwater fishacute: 96 hours,flow-throughOxyfluorfen(94)Rainbow trout(Oncorhynchusmykiss)LC50(95% C.I.) = 410 (310-560) μg/LNOAEC: Not specified(no mortality at 2 lowest test concentration, 140 and 180 μg/L;sublethal effects: darkening, lethargy, and loss of equilibrium)Highly toxicMRID 00081856AcceptableFreshwater fish earlylife stage: 30 days,flow through,standard laboratorylightingOxyfluorfentechnical(71)Fathead minnow(Pimephales promelas)NOAEC = 38 μg/L (mm)LOAEC = 74 μg/L (mm)Note: This study was conducted under standard laboratorylighting.(based on reduction in fry survival, total length, and weigh)MRIDs 00099270,00030249, and92136057AcceptableFreshwater fish earlylife stage: 33 days,flow through,enhanced UVlighting (chronic)Oxyfluorfentechnical(99.3)Fathead minnow(Pimephales promelas)NOAEC = 1.3 μg a.i./L (TWA)LOAEC = 2.4 μg a.i./L (TWA)Note: This study was conducted under UV lighting simulatingsummer light intensity for theFlorida or California latitudes.(based on most sensitive endpoint of post-hatch survival;hatching success, post-hatch physical/behavioral abnormalities,and growth [length, wet weight, and dry weight] also affected)MRID 46585104AcceptableEstuarine/marinefish acute: 96 hours,staticOxyfluorfentechnical(71.4)Sheepshead Minnow(Cyprinodonvariegatus)LC50> 116 μg a.i./L (mm)NOAEC = 60 μg a.i./L (mm)(no mortality; sublethal effect of surfacingaat≥130 μg a.i./L)Practically non-toxic up to the limit of solubilityMRID 41698801SupplementalEstuarine/marinefish early life stage(chronic)Oxyfluorfen Estuarine/marinespeciesNo dataNote: A chronic toxicity endpoint for estuarine/marine fishcannot be estimated using an acute-to-chronic ratio (ACR) forNA48Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationfreshwater fish because the available freshwater fish chronictoxicity endpoints were generated for fathead minnow, a speciesfor which we do not have an acute toxicity endpoint.Freshwaterinvertebrate: 48hours, staticOxyfluorfen (82.2) Water flea(Daphnia magna)LC50(95% C.I.) = 1.5 (0.75-2.9) mg/L (nom)Moderately toxicMRID 00134449AcceptableFreshwaterinvertebrate acute:48 hours, flowthroughGoal 2XL (P)(23.2)Water flea(Daphnia magna)EC50(95% C.I.) = 80 (60-150) μg a.i./L (mm)NOAEC = 20 μg a.i./L (mm)(NOAEC based on mortalityand sublethal effects)Very highly toxicMRID 45217301Supplemental(due to highvariability in %recovery of testsubstance)Freshwater mollusc:96 hoursOxyfluorfenTechnical(74)Freshwater clam(Elliptio complanata)LC50(95% C.I.) = 9.57 (6.67-13.73) mg/L MRID 00134452Supplemental(due to notfulfilling aguidelinerequirement)Freshwaterinvertebrate lifecycle: 21 days, flowthrough (chronic)Oxyfluorfentechnical(71.8)Water flea(Daphnia magna)NOAEC = 13 μg a.i./L (mm)LOAEC = 28 μg a.i./L (mm)(NOAEC based reductions in adult survival, growth [length],and reproductive output)MRIDs 45550201,92136106, and42142305AcceptableEstuarine/marineinvertebrate: 96hours, staticOxyfluorfentechnical(74)Grass shrimp(Palaemonetes pugio)LC50(95% C.I.) = 32 (18-56) μg/L (nom)NOAEC = 18 μg/L (nom)Very highly toxicMRIDs 00134451and 30970117Supplemental(due to guidelinedeviations)Estuarine/marinemollusc: 96 hours,flow through, shelldepositionOxyfluorfentechnical(71.4)Eastern oyster(Crassostreavirginica)EC50(95% C.I.) = 69.3 (62.2-98.5) μg a.i./L (mm)bNOAEC = 37.5 μg a.i./L (mm)cVery highly toxicMRID 42378901AcceptableEstuarine/marineinvertebrate: 96hours, staticOxyfluorfentechnical(74)Fiddler crab(Uca pugilator)Mortality = 30 and 20% at 560 and 1000 mg/L (nom),respectivelyMRID 00134450SupplementalEstuarine/marineinvertebrate lifeOxyfluorfentechnical(99.3)Mysid shrimp(Mysidopsis bahia)NOAEC = 8.1 μg a.i./L (TWA)LOAEC = 16 μg a.i./L (TWA)MRID 46597701Supplemental49Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationcycle: 30 days, flowthrough (chronic)(NOAEC based on most sensitive endpoint of reproduction;survival, and growth [length and dry weight] also affected))(due to guidelinedeviations)Benthic freshwaterinvertebrate: 10days, flow through,spiked sedimentOxyfluorfentechnical(99.3)Midge(Chironomus tentans)Based on pore water concentrations (mm)LC50> 498.5 μg a.i./LNOAEC = 484.5 μg a.i./LBased on sediment concentrations (dry weight, mm)LC50> 97.6 mg a.i./kg-dwNOAEC = 55.7 mg a.i./kg-dwBased on sediment concentrations (organic carbon [OC], mm)LC50> 4880 mg a.i./kg-OCNOAEC = 2750 mg a.i./kg-OC(NOAEC based on mortality)MRID 46585102Supplemental(due to lower thanrecommended lightintensity)Benthicestuarine/marineinvertebrate: 10days, static, spikedsedimentOxyfluorfentechnical(99.3)Amphipod(Leptocheirusplumulosus)Based on pore water concentrations (mm)LC50(95% C.I.) = 130 (81-200) μg a.i./LProbit slope = 2.73±0.833NOAEC = 27.9 μg a.i./LBased on sediment concentrations (mm)LC50(95% C.I.) = 37 (26-53) mg a.i./kg-dwProbit slope = 2.54±0.44NOAEC = 16.0 mg a.i./kg-dwBased on overlying water concentrations (mm)LC50(95% C.I.) = 42 (22-82) μg a.i./LProbit slope = 1.79±0.44NOAEC = 12.6 μg a.i./L(NOAEC based on mortality)MRID 46585103Supplemental(due to uncertainexposureconcentrations andnot usingcontinuous lightingper guideline)Benthic invertebrate:96 hours, static,spiked sedimentGoal 1.6E(19.5)14C-Goal 1.6E(99)Midge(Chironomus tentans)EC50> 5.1 mg Goal 1.6E/kg-dry soilEC50> 0.029 mg Goal 1.6E /L overlying waterMRID 42048001Supplemental forlow organic mattersoil(due to not testinghigh enough)50Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationAquatic vascularplant: 14 days, staticrenewalOxyfluorfentechnical (99.1)Duckweed(Lemna gibba)EC50(95% C.I.) = 0.33 (0.20-0.38-27) μg a.i./L (m)NOAEC/EC05: Could not be determined(based on most sensitive endpoint of frond number)MRID 45861103Supplemental (dueto uncertainexposureconcentrations)Aquatic nonvascular plant:96 hours, staticGoal 2XL (P)(23.2)Green alga(Selenastrumcapricornutum)EC50(95% C.I.) = 0.29 (0.27-30) μg a.i./L (mm)NOAEC = 0.10 μg a.i./L (mm)LOAEC = 0.26 μg a.i./L (mm)(NOAEC based on reduction in cell density)MRID 45271302AcceptableAquatic nonvascular plant:96-240 hours, static,sedimentOxyfluorfentechnical (99.1)Green alga(Pseudokirchneriellasubcapitata)96-hr EC50> 2.9 μg a.i./L (im)96-hr NOAEC = 1.4 μg a.i./L (im)96-hr LOAEC = 2.9 μg a.i./L (im)240-hr EC50> 2.9 μg a.i./L (im)240-hr NOAEC = 2.9 μg a.i./L (im)240-hr LOAEC > 2.9 μg a.i./L (im)(NOAEC based on reductions in cell density, growth rate, andbiomass)MRID 45581601Supplemental(due to guidelinedeviationsincluding use ofsediment)Aquatic nonvascular plant:120 hours, staticOxyfluorfentechnical (99.1)Cyanobacterium(Anabaena flos-aquae)EC50> 100 μg a.i./L (mm)NOAEC = 20.1 μg a.i./L (mm)LOAEC = 47.2 μg a.i./L (mm)(NOAEC based on most sensitive endpoint of biomass [areaunder the growth curve; cell density and growth rates alsoaffected)MRID 45861104Supplemental(due to uncertainexposureconcentrations)Aquatic nonvascular plant:120 hours, staticOxyfluorfentechnical (99.1)Freshwater diatom(Navicula pelliculosa)EC50= 29 μg a.i./L (mm)NOAEC = 19.2 μg a.i./L (mm)LOAEC = 49.7 μg a.i./L (mm)(based on most sensitive endpoint of cell density for EC50;growth rate and biomass alsoaffected with same NOAEC andLOAEC)MRID 45861105Supplemental(due to uncertainexposureconcentrations)Aquatic nonvascular plant:96 hours, staticOxyfluorfentechnical (99.1)Marine diatom(Skeletonemacostatum)EC50= 1.10 μg a.i./L (mm)NOAEC = 0.65 μg a.i./L (mm)LOAEC = 1.20 μg a.i./L (mm)(based on most sensitive endpoint of biomass [area under thecurve]; cell density and growth rate also affected)MRID 45861106Supplemental(due to uncertainexposureconcentrations)51Study TypeTest Substance(% a.i.)SpeciesToxicity Endpoints andAcute Toxicity Classification (If Applicable)Source& StudyClassificationAquatic nonvascular plant:96 hours, staticTEP: MON 780952.50% oxyfluorfen+30.27% glyphosateacid-equivalentGreen alga(Selenastrumcapricornutum)EC50= 0.213 μg oxyfluorfen/L (mm)NOAEC = 0.039 μg oxyfluorfen/L (mm)LOAEC = 0.088 μg oxyfluorfen/L (mm)EC50= 8.5 μg MON 78095/L (mm)NOAEC = 1.5 μg MON 78095/L (mm)NOAEC = 3.5 μg MON 78095/L (mm)(based on most sensitive endpoint of biomass [area under thecurve]; cell density and growth rate also affected)MRID 45906008AcceptableAbbreviations: C.I. = confidence interval; ELS = early life stage;im = initial measured; mm = mean measured; nom = nominal; NA= not applicable; NS = notspecified; TEP = typicalend-use product; TWA = time-weighted averageaThis observation was attributed to low dissolved oxygen. The study author proposed that the drop in dissolved oxygen could have been due to the accumulationof precipitated chemical on the surface of the water.b based on pooled control datacbased on comparison to solvent control; NOAEC may be lower when using a comparison to the negative control152Appendix C: EcologicalIncidents Associated with OxyfluorfenaIncidentNumberTaxaInvolvedEffectsRoute ofExposureMagnitudeYearStateUseLegality ofUseCertaintyCategoryResiduesOtherChemicalsInvolvedI023931-055 Terrestrial PlantdamageTreateddirectly1 bush 2012 TX Ornamental Undetermined Possible NotreportedGlyphosateI023097-009 Terrestrial Mortality Treateddirectly60-75 trees 2011 CA Orchard(almond)Misuse(accidental)Possible NotreportedPenoxsulamOryzalinI023097-010 Terrestrial PlantdamageTreateddirectly60 acres 2011 CA Orchard(almond)Undetermined Possible NotreportedOryzalinGlyphosateI023097-010bTerrestrial PlantdamageTreateddirectly60 acres 2011 CA Orchard(almond)Misuse(accidental)Possible NotreportedOryzalinGlyphosateI023097-011 Terrestrial PlantdamageTreateddirectlyUnknown 2011 CA Orchard(almond)Undetermined Possible NotreportedGlyphosatePenoxsulamPendimethalinI024499-001 Terrestrial Mortality Notreported60-75 trees 2011 CA Orchard(almond)Misuse(accidental)Possible NotreportedPenoxsulamI023044-006 Terrestrial Plantdamage(wheat)Drift,spray30% of 40acre2010 CA Cotton Misuse Probable NotreportedGlyphosateI023574-001 Plants PlantdamageNotreported66 acres 2010 CA Strawberry Undetermined Possible NotreportedNoneI020180-019 Plants Plantdamage(wheat)Drift,spray40 acres 2008 CA Cotton Undetermined Possible NotreportedGlyphosateI016962-027 Plants PlantdamageTreateddirectly38 acres 2004 OR Ryegrass Misuse(accidental)Probable NotreportedMetribuzinFlufenacetI021276-015 Plants PlantdamageDrift Notreported2004 WA AgriculturalareaMisuse Possible NotreportedGlyphosateI012366-049 Plants PlantDamage(onion)Treateddirectly33 acres 2001 CA N/r Misuse(accidental)Probable NotreportedBromoxyniloctanoate,AtrazineI013563-006 Plants PlantdamageTreateddirectly110 acres 2001 CA Beans Registered use Possible NotreportedMetribuzinI010844-001 Aquatic Mortality Spill Chinooksalmon(1336)2000 OR Spill Misuse(accidental)Probable 1-2 ppb(waterrange)None53IncidentNumberTaxaInvolvedEffectsRoute ofExposureMagnitudeYearStateUseLegality ofUseCertaintyCategoryResiduesOtherChemicalsInvolvedSteelhead(850)I013563-005 Plants PlantdamageTreateddirectly332 acres 2000 CA Almonds Registered use Possible NotreportedGlyphosate,IsopropylamineI013563-009 Plants PlantdamageTreateddirectly20 acres 2000 CA Grape Registered use Probable NotreportedSulfur,FenarimolI016102-001 Plants Plantdamage(blueberry)Drift 20 acres 2000 MI Tree farm/plantationRegistered use Possible NotreportedProdiamineI013563-003 Plants PlantdamageTreateddirectlyUnknown 1999 CA Onion Misuse(accidental)Possible NotreportedBromoxyniloctanoateI013563-004 Plants PlantdamageTreateddirectly10 acres 1999 CA Grapes Registered use Probable NotreportedNoneI013563-001 Plants PlantdamageTreateddirectlyUnknown 1998 CA Onions Registered use Possible NotreportedNoneI013563-008 Plants PlantdamageTreateddirectlyUnknown 1998 CA Grapes Registered use Probable NotreportedNoneI013563-002 Plants PlantdamageTreateddirectly78 acres 1997 CA Bean Misuse(accidental)Probable NotreportedNoneI013563-007 Plants Plantdamage(lettuce)Treateddirectly50 acres 1997 CA Field Misuse(accidental)Probable NotreportedNoneI003377-003 Plants Plantdamage(plum,almond)Drift Thousands 1996 CA N/r Misuse(accidental)Probable NotreportedGlyphosate,IsopropylaminesaltI013636-029 Plants Plantdamage(peppermint)Treateddirectly181 acres 1996 OR N/r Registered use Possible NotreportedParaquatdichloridea‘Minor’ incidents aggregately reported by theregistrant(s) are not included in this table.bSame incident as that listed above record, but second involves an additional application of an oxyfluorfen product which led to an exceedance in labelrecommendation for total amount of oxyfluorfen to be used on a single crop.

### 54 

## Appendix D: SIP and STIR Outputs

SIP (v. 1.0)

Table 1. Inputs

Parameter Value

Chemical name oxyfluorfen

Solubility (in water at 25 o C; mg/L) 0.116

Mammalian LD 50 (mg/kg-bw) 5000

Mammalian test species laboratory rat

Body weight (g) of "other" mammalian species

Mammalian NOAEL (mg/kg-bw) 20

Mammalian test species laboratory rat

Body weight (g) of "other" mammalian species

Avian LD 50 (mg/kg-bw) 2150

Avian test species mallard duck

Body weight (g) of "other" avian species

Mineau scaling factor 1.15

Mallard NOAEC (mg/kg-diet) 124

Bobwhite quail NOAEC (mg/kg-diet) 124

NOAEC (mg/kg-diet) for other bird species

Body weight (g) of other avian species

NOAEC (mg/kg-diet) for 2nd other bird species

Body weight (g) of 2nd other avian species

Table 2. Mammalian Results

Parameter Acute Chronic

Upper bound exposure (mg/kg-bw) 0.0200 0.0200

Adjusted toxicity value (mg/kg-bw) 3845.8028 15.3832

Ratio of exposure to toxicity 0.0000 0.0013

Conclusion* Drinking water

exposure alone is

NOT a potential

concern for mammals Drinking water exposure

alone is NOT a potential

concern for mammals

Table 3. Avian Results

Parameter Acute Chronic

Upper bound exposure (mg/kg-bw) 0.0940 0.0940

Adjusted toxicity value (mg/kg-bw) 1116.3346 6.1520

Ratio of exposure to acute toxicity 0.0001 0.0153

Conclusion* Drinking water

exposure alone is

NOT a potential

concern for birds Drinking water exposure

alone is NOT a potential

concern for birds

### 55 *Conclusion is for drinking water exposure alone. This does not combine all routes of exposure.

Therefore, when aggregated with other routes ( i.e ., diet, inhalation, dermal), pesticide exposure through

drinking water may contribute to a total exposure that has potential for effects to non-target animals.



### STIR (v. 1.0)



# Welcome to the EFED

Screening Tool for Inhalation Risk

This tool is designed to provide the risk assessor with a rapid method for determining

the potential

significance of the inhalation exposure route to birds and mammals in a risk

assessment.



# Input

Application and Chem ical Information

Enter Chemical Name oxyfluorfen

Enter Chemical Use multiple

Is the Application a Spray? (enter y or n) y

If Spray What Type (enter ground or air) ground

Enter Chemical Molecu lar Weight (g/mole) 361.72

Enter Chemical Vapor Pressure (mmHg) 2.50E-07

Enter Application Rate (lb a.i./acre) 2

Toxicity Properties

Bird

Enter Lowest Bird Oral LD 50 (mg/kg bw) 2150

Enter Mineau Scaling Factor

Enter Tested Bird Weight (kg) 0.178

Mammal

Enter Lowest Rat Oral LD 50 (mg/kg bw) 5000

Enter Lowest Rat Inhalation LC 50 (mg/L) 3.71

Duration of Rat Inhalation Study (hrs) 4

Enter Rat Weight (kg) 0.35



# Output

Results Avian (0.020 kg )

Maximum Vapor Concentration in Air at Saturation

(mg/m 3 ) 4.87E-03

Maximum 1-hour Vapor Inhalation Dose (mg/kg) 6.12E-04

Adjusted Inhalation LD 50 1.10E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 5.57E-06 Exposure not Likely

Significant

Maximum Post-treatment Spray Inhalation Dose (mg/kg) 2.11E-01

### 56 Ratio of Droplet Inhalation Dose to Adjusted Inhalation

LD 50 1.92E-03 Exposure not Likely

Significant



### Results Mammalian (0.015 kg )

Maximum Vapor Concentration in Air at Saturation

(mg/m 3 ) 4.87E-03

Maximum 1-hour Vapor Inhalation Dose (mg/kg) 7.69E-04

Adjusted Inhalation LD 50 2.21E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 3.48E-06 Exposure not Likely

Significant

Maximum Post-treatment Spray Inhalation Dose (mg/kg) 2.66E-01

Ratio of Droplet Inhalation Dose to Adjusted Inhalation

LD 50 1.20E-03 Exposure not Likely

Significant



# Welcome to the EFED

Screening Tool for Inhalation Risk

This tool is designed to provide the risk assessor with a rapid method for determining

the potential

significance of the inhalation exposure route to birds and mammals in a risk

assessment.



# Input

Application and Chem ical Information

Enter Chemical Name oxyfluorfen

Enter Chemical Use multiple

Is the Application a Spray? (enter y or n) y

If Spray What Type (enter ground or air) air

Enter Chemical Molecu lar Weight (g/mole) 361.72

Enter Chemical Vapor Pressure (mmHg) 2.50E-07

Enter Application Rate (lb a.i./acre) 0.5

Toxicity Properties

Bird

Enter Lowest Bird Oral LD 50 (mg/kg bw) 2150

Enter Mineau Scaling Factor

Enter Tested Bird Weight (kg) 0.178

Mammal

Enter Lowest Rat Oral LD 50 (mg/kg bw) 5000

Enter Lowest Rat Inhalation LC 50 (mg/L) 3.71

Duration of Rat Inhalation Study (hrs) 4

Enter Rat Weight (kg) 0.35



# Output

### 57 Results Avian (0.020 kg )

Maximum Vapor Concentration in Air at Saturation

(mg/m 3 ) 4.87E-03

Maximum 1-hour Vapor Inhalation Dose (mg/kg) 6.12E-04

Adjusted Inhalation LD 50 1.10E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 5.57E-06 Exposure not Likely

Significant

Maximum Post-treatment Spray Inhalation Dose (mg/kg) 4.80E-02

Ratio of Droplet Inhalation Dose to Adjusted Inhalation

LD 50 4.37E-04 Exposure not Likely

Significant



### Results Mammalian (0.015 kg )

Maximum Vapor Concentration in Air at Saturation

(mg/m 3 ) 4.87E-03

Maximum 1-hour Vapor Inhalation Dose (mg/kg) 7.69E-04

Adjusted Inhalation LD 50 2.21E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 3.48E-06 Exposure not Likely

Significant

Maximum Post-treatment Spray Inhalation Dose (mg/kg) 6.04E-02

Ratio of Droplet Inhalation Dose to Adjusted Inhalation

LD 50 2.73E-04 Exposure not Likely

Significant

### 58 Appendix E: Results of ECOSAR Modeling

ECOSAR is a screening-level tool based on chemical struct ures developed by the USEPA’s

Office of Chemical Safety and Pollution Preven tion for rapid screening of chemicals for

ecotoxicity hazards. The modeling results show that MW-332, a degradate of oxyfluorfen, is

about 3-4 times less toxic than parent oxyfluor fen. With the exception of green algae, the

ECOSAR estimated toxicity values for oxyfluorfen are similar to observed toxicity values.

Taxon Endpoint (mg/L)

Oxyfluorfen

ECOSAR Class:

Neutral Organic SAR Oxyfluorfen

Observed MW-332

ECOSAR Class:

Neutral Organic SAR

Acute Chronic Acute Chronic Acute Chronic

Fish 0.392 0.054 0.200 0.038/0.0013* 1.132 0.148

Daphnid 0.299 0.066 0.080 0.013 0.821 0.158

Green algae 0.758 0.384 0.00029 - 1.685 0.761

Saltwater fish 0.503 0.387 >0.170 - - -

Saltwater mysid 0.043 0.0014 0.032 0.008 - -

* Standard laboratory lighting/UV lighting