### 2 Key Uncertainties and Data Gaps

Major findings include the follo wing data needs and the uncertain ties described below:

 Anaerobic aquatic metabolism (835.4400): An anaerobic aquatic metabolism study is not available. A guidelin e compliant study is

needed because the data is of core input to EFED’s exposur e models in risk assessment.

 Adsorption/Desorption (835.1230): Most of the previously submitted studies we re unacceptable due the use of sterilized soils. Data is available for a study on fluazifop-p-acid but the study is deemed supplemental due to insufficient mass balance, use of only foreign soils, and absence of soils with less than 1% organic matter. A new study is needed for fluazifop-p-butyl and its degradates.

 Avian Reproduction (850.2300): Avian Reproduction studies were submitted a nd reviewed in 1982. These studies used technical fluazifop-butyl, which is now can celled. There were a number of problems

with these studies which included deaths in the controls and maximum concentrations (50 ppm in both studies) were less than expected maximum field residue exposure levels (in the current case 1.125 lbs a.i./A x 240 ppm = 270 ppm). The SOP recommends testing at concentrations equal to exp ected field residue levels. Testing should be done with fluazifop-p acid, since f luazifop-P-butyl is rapidly degraded in soil to fluazifop-p acid, which is much more stable in soil and water environments than the parent.



###  Honeybee toxicity (non-guideline): In keeping with the Agency’s proposed new paradigm for determining potential adverse effects to insect pollinators from conven tional pesticides (USEPA 2012), additional studies are being requested in addition to the acute contact study already submitted. Even though contact to fluazifop-p-butyl is sligh tly toxic to honeybees, an adult acute oral toxicity study (following OECD 213) and a la rval toxicity study (following OECD 237) are necessary to evaluate the potential for fl uazifop-p-butyl and/or acid to adversely affect bees and other pollinat ors through other routes of e xposure. In addition, adult and larval chronic studies are being requested. Several of the treated crop areas may be considered attractive to honey bees and this is a systemic chemical that is transported throughout the plant. Thus, residues may be available to pollinators via pollen and/or

nectar.

 Terrestrial Plant Toxicity (850.4100 and 850.4150): Fluazifop-p-butyl is a post-emergent sy stemic aryloxyphenoxypropionic herbicide to control perennial and annual gras s weeds. In general, it has little effect on broad-leaved plants (dicots) (Ware and Whitacre 2004). Fl uazifop-p-butyl is registered to control monocot plant species and ther e are reported incidents in EFED’s Ecological Incident Information System (EIIS) database where cr op damage was reported on corn, which is a monocot species. There are no gui deline toxicity data to assess risks to terrestrial plants. Tier I seedling emergence and vegetative vigor studies are needed. Testing should be done with fluazifop-p-butyl which degrades rapidly in soil into fluazifop-p acid, both toxic components of herbicidal activity. Two studies (vegetative vigor and seedling emergence) have been recently submitted and ar e in review. If these studies are found to be scientifically sound, then new studies will not be needed.

### 3  Aquatic Plant Toxicity (850.4400, 850.4500 & 850.4550): Aquatic plant testing is required for any herbicide that has ou tdoor non-residential terrestrial uses that may move off-site by runo ff, by drift, or that is applied directly to water. Two aquatic plant studies have been submitted and one was deemed invalid. The second study used metabolite X and is currently in review. Tier II testing should be done using fluazifop-p acid.

 Estuarine/Marine Fish (850.1350 and 850.1400): No data have been submitted regarding chr onic toxicity to estuar ine/marine fish or invertebrates. Fluazifop is hi ghly acutely toxic to freshwater fish and invertebrates. In addition, use on golf courses can occur near estuarine areas. Since fluazifop-p-butyl breaks down very quickly, testing should be don e using the acid for chronic studies.

All degradation and analytical method studies should state the enanti omeric purity of the chemical used in testing and the enantiomer ratios in the residue characterizations.

### 4 

# Table	of	Contents

1. Introduction .................................................................................................................. ........... 5

2. Use Characterization .......................................................................................................... ..... 5

3. Conclusions from Previous Risk Assessments ..................................................................... 10

3.1. Ecological Risk Assessments ......................................................................................... 10

3.2. Drinking Water Exposure Assessments ......................................................................... 10

3.3. Clean Water Act Programs ............................................................................................. 10

3.3.1. Aquatic Life Criteria and Aquatic Life Benchmarks .................................................. 10

3.3.2. Impaired Water Bodies ............................................................................................... 11

4. Environmental Fate and Transport........................................................................................ 11 4.1. Chemical Identity and Mode of Action .......................................................................... 11 4.2. Enantiomer Considerations for Fluazifop-p-butyl ......................................................... 12 4.3. Physico-chemical Properties of Fl uazifop-p-butyl and Related Compounds ................ 13 4.4. Environmental Fate and Transport...............................................................16

4.5. Transformation Products ............................................................................................... .. 19 5. Receptors .............................................................................................................. ................. 29

5.1. Effects to Aquatic Organisms ........................................................................................ 30

5.2. Effects to Terrestrial Organisms .................................................................................... 31

5.3. Ecological Incidents ....................................................................................................... 32

6. Exposure Pathways of Concern ............................................................................................ 33

7. Analysis Plan ................................................................................................................. ....... 34

7.1. Stressors of Concern....................................................................................................... 34

7.2. Measures of Exposure .................................................................................................... 34

7.3. Measures of Effect ......................................................................................................... 34

8. Endangered Species Assessments ......................................................................................... 35

9. Endocrine Disruptor Screening Program .............................................................................. 35

10. Preliminary Identificati on of Data Gaps ............................................................................... 37

10.1. Environmental Fate ........................................................................................................ 37

10.2. Ecological Effects ........................................................................................................... 44

11. References .................................................................................................................... ...... 47 APPENDIX A: Eco and Fate Bibliography for Fluazifop ............................................................ 51

APPENDIX B: ECOLOGICAL TOXICITY DATA ................................................................... 65 APPENDIX C: Example of SIP INPUT and OUTPUT ............................................................... 75 APPENDIX D: STIR inputs and outputs ...................................................................................... 77

### Page 5 of 78 

# 1. Introduction

EFED evaluated the most recent ecological risk assessments for fl uazifop-p-butyl in association with the updated toxicity, exposur e, and usage information to determine if sufficient data are available and if further updates are needed to support registration review. Recent risk

assessments include new use assessments in 2008 (peanuts and dry b eans) and 2010 (bananas, plantains, citrus, grapes and sugarbeets). In addition, EFED considered the latest Agency science policies and risk assessment methodologies. The structure of flua zifop-p-butyl, as well as the chemical names and other identifiers, can be found in the environmental fate section.

Butyl ( R )-2-{4-[5-(trifluoromethyl)- 2-pyridyloxy]phenoxy}propionate (common name fluazifopp-butyl) is an aryloxphenoxypropionic (formerl y oxyphenoxy acid esters) class herbicide (Wood 2007; Ware and Whitacre 2007). The mode of action is via inhibiti on of CoA carboxylase, resulting in decreased lipid synthesis, especial ly at sites of active gr owth resulting in the disruption of cell walls (Tu et al. 2001). It is selectiv e, post-emergent, and systemic and is used to control perennial and annual grass weeds (Wo od 2007). In general, it has little effect on broad-leaved plants (dicots) (Ware and Whitacr e 2004). It is rapidly absorbed through leaf surfaces and hydrolyzes in the plant to fluazif op-acid, and then it is transported in phloem and accumulates in the meristems (Tu et al . 2001). It may be applied as a ground spray, aerial spray, and in irrigation systems. Fluazifop-P-butyl is rapidly (less than one day) degraded in soil to fluazifop acid, which is much more stable in soil and water environments than the parent. Fluazifopand its acid degradate exist as stereoisomers. In this assessment, fluazifop-p-butyl and fluazifop-pacid refer to the enriched (R) isomer, which is the more herbicidally active form. Fluazifop butyl and fluazifop acid (without the “p” designation) refe r to the racemic mixture (50% R,S). Current products contain the R-enriched isomer, fluazifop-p-butyl.



# 2. Use Characterization

Uses of fluazifop-p-butyl include terrestrial agricultural food uses, nonfood uses such as fallow land and noncrop areas, and reside ntial/commercial uses such as turf, ornamentals, and in landscapes.

### Page 6 of 78 

### Table 1. Maximum application rates for current uses of Fluazifop-p-butyl

Site Single

App Rate (lb ai / A) Max #Apps/CC Max Dose/CC
(lb ai / A/CC) Max #Apps/Year Max Dose/Year

(lb ai / A/Yr) MRI (days) Reg Numbers

Soybeans 0.375 1 0.375 1 0.47 14 100

‐ 1059

Cotton 0.375 2 0.750 2 0.750 14 100

‐ 1059

Roadside Rights

‐ of

‐

way 0.375 1 0.375 1 0.375 14 100

‐ 1059

Apricots, Cherries,

Nectarines, Peaches,
Plums, Prunes 0.375 3 1.125 3 1.125 14 100

‐ 1070

Asparagus 0.375 2 0.750 2 0.750 14 100

‐ 1070

Asparagus 0.188 2 0.375 2 0.375 21 100

‐ 1070

Bananas and Plantains 0.375 3 1.125 3 1.125 30 100

‐ 1070

Carrots (including seed

carrots), dry Bulb

Onions, Garlic 0.375 2 0.750 2 0.750 14 100

‐ 1070

Citrus Fruits 0.375 3 1.125 3 1.125 21 100

‐ 1070

Coffee 0.375 2 0.750 2 0.750 14 100

‐ 1070

Cotton 0.375 2 0.750 2 0.750 14

Dry Beans (except
cowpeas) 0.375 2 0.750 2 0.750 14 100

‐ 1070

Grapes 0.375 3 1.125 3 1.125 14 100

‐ 1070

Macadamia Nuts 0.375 2 0.750 2 0.750 14 100

‐ 1070

Peanuts 0.375 2 0.750 2 0.750 14 100

‐ 1070

Pecans 0.375 3 1.125 3 1.125 14 100

‐ 1070

Rhubarb 0.375 2 0.563 2 0.563 14 100

‐ 1070

Soybeans 0.375 2 0.47 2 0.47 14 100

‐ 1070

Sugar beets 0.375 2 0.750 2 0.750 14 100

‐ 1070

Sweet potatoes, Yams 0.375 2 0.750 2 0.750 14 100

‐ 1070

Tabasco Peppers 0.375 2 0.750 2 0.750 14 100

‐ 1070

Non

‐ bearing groves, Orchards, Vineyards,

Tree Farms* 0.375 3 1.125 3 1.125 14 100

‐ 1070

Non

‐ food use ‐ Agricultural Fallow

Land and Non

‐ crop

areas 0.375 3 1.125 3 1.125 14 100

‐ 1070

Landscaped areas, roadsides, field grown ornamentals,
greenhouses,

nurseries, flower beds,

and all other non

‐ turf

areas 0.375 2 0.75 2 0.75 14 100

‐ 1084

### Page 7 of 78 Site Single

App Rate (lb ai / A) Max #Apps/CC Max Dose/CC
(lb ai / A/CC) Max #Apps/Year Max Dose/Year

(lb ai / A/Yr) MRI (days) Reg Numbers

Zoysia, Tall Fescue 0.094 not specified not

addressed

on label not specified not specified 28 100

‐ 1084

Alfalfa Grown for

Seed 0.125

‐ 0.188 2 0.313 2 0.313 14 OR

‐ 040006 (100

‐ 1070)

Alfalfa Grown for

Seed and Clover

Grown for Seed 0.19 2 0.313 2 0.313 14 NV

‐ 040006 (100

‐ 1070)

Alfalfa Grown for

Seed
0.125

‐ 0.188 2 0.313 2 0.313 14 MT

‐ 030010 (100

‐ 1070)

WA

‐ 040007 (100

‐ 1070)

WY

‐ 03

‐ 0006 (100

‐ 1070)

Alfalfa Grown for

Seed and Clover

Grown for Seed ID

‐ 950006 (100

‐ 1070)

Fine Fescue Grasses

(chewings, hard,

and creeping red
varieties) grown for

Seed 0.25 4 1 4 1 before
regrowth

exceeds

10 in. ID

‐ 040003 (100

‐ 1070)

Fine Fescues grown
for Seed 0.25 4 1.00 4 1.00 before
regrowth

exceeds

10 in. OR

‐ 950013 (100

‐ 1070)

Fine Fescue Grasses

(chewings, hard,

and creeping red
varieties) grown for

Seed 0.25 4 1.00 4 1.00 before
regrowth

exceeds

10 in. WA

‐ 040024 (100

‐ 1070)

Guayule (non

‐ food
use) 0.375 3 1.125 3 1.125 28 AZ

‐ 070006 (100

‐ 1070)

Cabbage, Chinese

cabbage, Kale,
Spinach, Swiss
Chard, Table Beet

Grown for Seed 0.25 2 0.50 2 0.50 None

Listed WA

‐ 040006 (100

‐ 1070)

Wildlands 0.375 3 1.125 3 1.125 14 CA

‐ 110010 (100

‐ 1070)

Prairie and Riparian

Conservation and

Restoration Areas 0.375 3 1.125 3 1.125 14 OR

‐ 120016 (100

‐ 1070)

Daffodils 0.25 1 0.25 1 0.25 NA WA

‐ 130007 (100

‐ 1084)

### Page 8 of 78 Restriction Codes

1 ‐ Do not graze animals in treated areas

2 ‐ All states except California and Arizona

3 ‐ California only

4 ‐ Includes Calamondin, Citrus citron, Citrus hybrids, Grapefruit, Kumquat, Lemon, Lime, Mandarin (Tangerine), Orange (all),
Pummelo, and Satsuma

5 ‐ Hawaii only

6 ‐ Do not apply to cotton after boll set

7 ‐ Do not graze or harvest for forage or hay

8 ‐ Do not apply to cowpeas

9 ‐ Do not graze animals in treated areas or feed cover crop of treated macadamia groves to livestock

10 ‐ Do not feed green immature growing plants to livestock or harvest for livestock feed

11 ‐ Maryland and New Jersey only

12 ‐ Do not exceed 1.2 lbs. (76 fl oz.) per acre over a two year period

13 ‐ Do not apply more than 24 fl. oz. per acre pre bloom (up to V5). Do not apply more than 6 fl oz. per acre from bloom
through post bloom (R1 or later).

14 ‐ Louisiana only

15 ‐ Apply to actively growing grasses before they exceed the specified growth stages.

Spray to obtain thorough coverage, but not to runoff. Repeat treatments may be necessary.
Apply when first grass species in a mixed grasss weed population reaches the specified growth stage for treatment

Do not apply to grasses which are stressed due to moisture, temperature, low soil fertility, mechanical or chemical injury.

Do not apply to grasses which have tillered, formed seed heads, or exceeded listed growth stages.

When treating nonbearing trees and vines, avoid contact of spray with foliage by using directed sprays.

Do not apply to trees, vines, or other listed crops that will be harvested for food/feed within one year after application

Do not apply to asparagus from which the spears will be harvested within 1 year of treatment.

Do not graze or harvest Florigraze rhizoma peanuts for 1 year after treatment.

Do not plant rotational grass crops such as corn, sorghum and cereals within 60 days after the last application.

Do not apply a total of more than 72 fluid ounces per acre per season.

16 ‐ Spray to obtain thorough coverage of grass foliage, but not to runoff. Repeat treatments may be necessary.

Apply when first grass species in a mixed grasss weed population reaches the specified growth stage for treatment

Do not apply to grasses which are stressed due to moisture, temperature, low soil fertility, mechanical or chemical injury.

Do not apply to grasses which have tillered, formed seed heads, or exceeded listed growth stages.

Do not apply a total of more than 72 fluid ounces per acre per season.

17 ‐ Do not graze animals in treated areas or feed treated plants.

18 ‐ No portion of this seed crop may be used for food or feed for 1 year after the last application.

19 ‐ No portion of the treated field, including seed, seed screenings, hay, forage, or stubble, may be used for human or animal

feed.

20 ‐ No portion of the alfalfa seed plant, including but not limited to green chop, hay, pellets, meal, whole
seed, cracked seed, roots, bulbs, leaves and seed screenings may be used or distributed for food or feed

purposes.

21 ‐ Do not plant rotational grass crops such as corn, sorghum and cereals within 60 days after last application.

22 ‐ Treated fields may not be grazed or harvested for forage until after harvesting grass seed crop.

23 ‐ Do not graze livestock in treated fields within 1 year (365 days) of application.

24 ‐ Do not allow livestock to graze treated fields. Do not use treated crops for livestock feed. Crop residues are not to be fed

to livestock or baled for such use

25 ‐ No portion of the cabbage, chinese cabbage, kale, spinach, swiss chard, and table beet seed plant may be used or
distributed for food or feed purposes.

### Page 9 of 78 

### Figure 1. Agricultural Usage of fluazi fop-p-butyl in 2011 (USGS, 2014)

. ( From the Pesticide National Synthesis Project available at: http://water.usgs.gov/nawqa/pnsp/us age/maps/show_map.php?year=2011&map= FLUAZIFOP&hilo=L&disp=Fluazifop)

### Page 10 of 78 

# 3. Conclusions from Previous Risk Assessments

3.1. Ecological Risk Assessments

The Agency has previously conducted ecological ri sk assessments on fluazifop that serve as a basis for this problem formulation. The primar y risks described in previous assessments have

been risks to terrestrial plants and aquatic monocots, which is expected given that fluazifop is an

herbicide. Risks of concern have also been identified to mammals and saltwater invertebrates from chronic exposure.



## 3.2 Drinking Water Exposure Assessments

In 2010, a drinking water exposure assessment fo r fluazifop-p-butyl wa s conducted to support

the human health risk assessment for the Section 3 new use registration on bananas, plantains, citrus, grapes, and sugar beet s pre-bloom and post-bloom (Str ader 2009). It was conducted on fluazifop-p-butyl residues of concern which is the parent compound and its acid. For aerial applications the highest surface water EECs reporte d for peak, 1-in-10 peak, 1-in-10 year annual mean, and the 30 year mean as estimated by PR ZM/EXAMS for all crop use scenarios were 33.4 ppb, 6.6 ppb, and 4.4 ppb, respectively. For ground a pplications the highest EECs for 1-in-10 peak, 1-in-10 year annual mean, and th e 30 year mean were 32.1 ppb, 5.8 ppb, and 3.1 ppb, respectively. SCI-GROW estimated the concentrat ion of fluazifop-acid in shallow ground water sources to be 1.56 ppb 1 

### . An updated drinking water assessment will be conducted for registration review, if needed.



## 3.3 Clean Water Act Programs

3.1.1. Aquatic Life Criteria and Aquatic Life Benchmarks

The Clean Water Act requires the Agency to publish water quality criteria that accurately reflect the latest scientific knowledge on the kind and ex tent of all identifiabl e effects on health and welfare that might be expected from the presen ce of pollutants in any body of water, including ground water. While these recommended cr iteria do not, in themselves, impose any requirements, states and authorized tribes can us e them to develop water quality standards. An Aquatic Life Ambient Water Qu ality Criteria documen t has not been published for fluazifop-pbutyl (see url: http://www.epa.gov/wate rscience/criteria/ ).

The Office of Pesticide Programs (OPP) publishes a quatic life benchmarks for freshwater species based on toxicity values for the most sensitive species from the most recent risk assessments. However, aquatic life benchmarks have not been published for fluazifop-p- butyl or its acid (see

url: http://www.epa.gov/oppefed1/ecorisk_ders/aquatic_life_benchmark.htm#benchmarks ).

1 Memorandum from Wm. J. Shaughnessy, EFED ERBII to Joanne Miller, Registration Division, subj: Drinking Water Assessment for the Section 3 Registration of Fluazifop-p-butyl for New Use on Bananas, Plantains, Citrus, Grapes and Sugar Beets.

### Page 11 of 78 

## 3.1.2. Impaired Water Bodies

Fluazifop-p-butyl is not identified as a cause of impairment for any water bodies listed as impaired under section 303(d) of the Clean Water Act, based on information provided at http://iaspub.epa.gov/tmdl_waters10/attains_ nation_cy.cause_detail_303d?p_cause_group_id=88

5

.

No Total Maximum Daily Load (TMDL) criteria have been developed for fluazifop-p-butyl, based on information provided at http://iaspub.epa.gov/tmdl_waters10/attains_ nation.tmdl_pollutant_de tail?p_pollutant_group_id =885&p_pollutant_group_name=PESTICIDES . More information on impaired water bodies and

TMDLs can be found at http://www.epa.gov/owow/tmdl/ . The Agency invites submission of water quality data for this pesticide. To the exte nt possible, data should conform to the quality standards in Appendix A of the OPP Standard Operating Procedur e: Inclusion of Impaired Water Body and Other Water Quality Data in OPP’s Regist ration Review Risk Assessment and Management Process (see: http://www.epa.gov/oppsrrd1/regist ration_review/water_quality_sop.htm ), in order to ensure they can be used quantitatively or qual itatively in pesticide risk assessments.



# 4. Environmental Fate and Transport

4.1. Chemical Identity and Mode of Action

Fluazifop-p-butyl, [butyl ( R )-2-{4-[5-(trifluoromethyl)-2-pyr idyloxy]phenoxy}propionate, (CAS No. 79241-46-6; PC code 122809)] is a R-isomer ch iral molecule from the racemic mixture (50:50 R & S form) of fluazifop-but yl. It is relatively non-pers istent and non-mobile in the

environment as it rapidly (T 1/2 

### = 0 - <2 d) degrades in aerobic soil (both laboratory soil and field dissipation studies) to fluazifop-acids ( 

### may be present in the R or S form or as a mixture of the enantiomers)

. 

### Fluazifop-p-butyl is not likely to volatize (1.7 x 10 -6 

### torr) at environmental temperatures, degrades sl owly via soil photolysis ( T 1/2 

### = 195 d), 

### and is slightly soluble (1.0 mg/L) with higher affinity for organi cs than for water. The acids are much more persistent in soil and water environments than the parent. Thus, studies on the fluazifop-acids were used to fulfill some of the data requirements of the parent compound. Both enantiomers are currently reviewed together

because there is no evidence so far that indicate 

### that the environmental fate would be different for the different enantiomers. Other major degrad ates of fluazifop-p-butyl are 2-hydroxy-5- trifluoromethylpyridine (degradate X), 4-(5-Tri fluoromethylpyridin-2-yloxy) phenol (degradate IV), SYN546933, and R201189. There are currently no data for fluazif op-p-butyl regarding anaerobic aquatic metabolism and no acceptable batch equilibrium study. However, leaching and field dissipation studies showed that fluazifop-acids, which are pr esent in the anionic form at most environmental pHs, are expected to be high ly mobile and have the potential to leach into groundwater.

Table 3. Chemical identification for the active ingredient fluazifop-p-butyl

Common Name: Fluazifop-p-butyl Pesticide Class: aryloxphenoxypropionic herbicide

EPA PC Code: 122809 IUPAC Name: butyl ( R )-2-{4-[5-(trifluoromethyl)-2-pyridyloxy]phenoxy}propionate

### Page 12 of 78 CAS Name: butyl (2 R )-2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenoxy]propanoate

CAS No: 79241-46-6 Synonyms: fluazifop-P butyl ester; fluazifop-r-butyl; Fusilade 2000; Fusilade DX; Fusilade S; Fusilade super; PP 005; Propanoic acid, 2-(4-((5-(tri fluoromethyl)-2-pyridinyl)oxy)phenoxy)-, butyl ester, (R)- SMILES Code: n1cc(C( F)(F)F)ccc1Oc2ccc(OC (C)C(=O)OCCCC)cc2

Structure:



## 4.2. Enantiomer Considerations for Fluazifop-p-butyl

A few different compounds are associated with the common name, fluazi fop-butyl. Fluazifopbutyl is the racemic mixture ( e.g., consists of equal amounts of the R and S enantiomers) of butyl-2-{4-[5-(trifluoromethyl)-2 -pyridyloxy]phenoxy}propionate. Fluazifop-p-butyl (PC Code 122809) is the R enantiomer and is more herb icidally active than the S enantiomer (Tu et al. 2001). Both degrade via microbi al mediated hydrolysis in mo ist soil and sediments to the fluazifop-acid which can also exist in the R or S form (MRID 162455; 87493, 92067033, 87492, 92067032, 46190602, 46190605).

U.S.EPA 2 

### formerly indicated that the data requireme nts for the two active ingredients should be considered separately. This approach is suppor ted by reports that different enantiomers of the

same chemical can have diffe rent biological activities, e.g ., toxicities (Xu et al. 2008). 3 

### In the same memo (1991), the environmental fate review indicated that data fo r fluazifop-butyl would be acceptable to fulfill the environmental fate re quirements of fluazifop-p-butyl, unless evidence

indicated that the envi ronmental fate would be different for the different enantiomers.

Enantiomers have been studied for fluazifop-but yl and related compounds in three British soils and in a mixed microbial population where convers ion of the S acid to the R acid was reported (Bewick 1986). The R:S enantiomer ratio of flu azifop-acid in two soils was approximately 82:18 at two days after applicati on of fluazifop-butyl, and ranged from 93:7 to 95:5 from 3 to 12 weeks after application; however , in a third loamy sand soil, th e R:S ratio was 64:36 at 3 weeks after application of fluazifop-butyl a nd was 92:8 at 12 weeks (MRID 87493, 92067032, 162455). When the S-enantiomer of fluazifop-butyl was applied to a sandy loam soil (British classification), it was hydrolyzed to fluazifop-acid which gradua lly changed to 98% present in the R form over 7 days (MRID 162455). Negre et al. (1993) reported that the S-enantiomer of

2 Transmittal of EFED list B Review of Fluazifop-butyl and fluazifop-p-butyl (Case # 2285; Chemical #, 122805, 122809; Memo from A. Rispin dated March 4, 1991).

3 The differing toxicity of the enantiomers is also illustrate d by the differences in the effectiveness of the different

enantiomers as herbicides. N

C F

F

F O

O C CH 3

C O

O C H 2 C H 2 C H 2 CH 3 H

### Page 13 of 78 

### fluazifop-acid was degraded at a much faster rate than the R-enantiomer by a mixed microbial culture, and indicated that the change in the ratios was not a result of the conversion of the S

form to the R form but a result of different ra tes of degradation. This was supported by showing

that two different rates of de gradation existed. Enantioselective degradation and enantiomer interconversions were also reported for chiral phenoxyalkanoic acid herbic ides with selective

conversion to or enrichment of the R enantio mer (Muller and Buser 1997). Stereoselective

metabolism and enantiomer interconversions ofte n depend on the microbial species present and more information is needed to predict the behavi or of the enantiomers in the natural environment (Muller and Buser 1997; Polarco et al. 1999; Qin et al. 2006). For exampl e, preferential degradation of the S isomer of dichlorprop and mecoprop was observed in soil and different stereoselectivity may occur in different media (Wang et al. 2005; Qin et al. 2006). Finally, some compounds have been shown to unde rgo enantiomerization in polar solvents, alcohols, and water and it is possible that fl uazifop-p-butyl and fluazi fop-p-acid may racemize, e.g ., form equal amounts of the R and S enantiomers, in water (Qin and Gan 2007; Lee 1989).

These studies suggest that information on the R enantiomer should be adequate as fluazifop-pacid is expected to be applied to soils and the S fo rm is either degraded fa ster or converted to the R form in soil. Given that there is no clear trend for how enantiomer-selectivity occurs in the environment, the exposure may be viewed as th e exposure to total resi dues of fluazifop-acid, with assumptions that fluazifop-ac id may be present in the R or S form or as a mixture of the enantiomers and this assumption will be conser vative for the purposes of risk assessment. Hence, the racemic mixture and R forms are reviewed together here as the environmental fate of

both forms is relevant to the environmental fate assessment.



## 4.3. Physico-chemical Properties of Fluazifop-p-butyl and Related Compounds

Physical and chemical propertie s can be used to identify a priori the potential behavior of a chemical in the environment. Table 4 provides a summary of the physico-chemical properties of fluazifop-p-butyl and related compounds.

Fluazifop-p-butyl, with vapor pr essure in the range of 2.25 x 10 -7 

### to 1.7 x 10 -6 

### torr, is not likely to volatize substantially at environmental temperatures (MRID 47272601, Corbin et al . 2006). It is slightly soluble (MRID 47272601) with a higher affinity for or ganics than for water (MRID 47272601; US EPA 2004) and has the potentia l to accumulate in organisms.

Fluazifop-acid and fluazifop-p-aci d are weak acids. At typica l environmental pHs, fluazifopacid is mainly in anionic form (assuming a pKa of 3.12, 88% is ionized at pH 4, 98% ionized at pH 5, and greater than 99% ionized at pH 5.5 and hi gher). It is highly sol uble in water and it is expected to have a higher affi nity for organics and lower solubility in its neutral form, e.g ., at lower pH.

### Page 14 of 78 

### Finally, the estimated vapor pre ssure of fluazifop-acid indicate s it is borderline between semivolatile and non-volatile. 4 

### While volatility is expected to be low for both fluazifop-acid and fluazifop-butyl, volatilization under some conditi ons cannot be ruled out because fluazifop-butyl

has been detected in air in an agricultural area (White et al. 2006) and the va por pressure of fluazifop-acid is estimated. Fl uazifop-p-butyl was detected at low concentrations (0.02-0.07 ng/m 3 

### ) in air at two potato farm sites in Prince Edward Island, Canada (White et al. 2006). The authors noted that these were among the first reported detections of fluazifop-p butyl in air. The Agency is not aware of any other studies that have found either fluazifop but yl or acid in the air.

Table 4. Summary of Physico-Chemical Properti es of Fluazifop-p-buty l and related Compounds 1

.

Property Fluazifop-p-butyl Flua zifop-butyl Fluazifop-p-acid
Empirical Formula C 19 H 20 F 3 NO 4 C 19 H 20 F 3 NO 4 C 15 H 12 F 3 NO 4 Molecular weight (g/mole) 383.37 2 383.37 327.26

Boiling Point ( o C) Thermal decomposition begins at 100 o C (PAI) 5

164.5 2 Slight decomposition starts at 370 o C (TGAI) 5 165 at 0.02 mmHg 4

Density (g/mL) 1.22 at 20 o C (PAI) 5, 11

1.21 at 20  C (TGAI) 5, 11
1.20 g.cm -3 (TGAI) 11, 12 1.21 3
1.20 g.cm -3 (TGAI) 11, 12

Dissociation Constant, pKa No pKa between pH 1 and 12.0 5 3.1 (PAI) 12 3.1 (PAI) 12 3.12 7

2.7 8

Vapor Pressure (torr) 9.0 x 10 -7 at 20 o C 5

1.7 x 10 -6 at 25 o C 5

2.25 x 10 -7 at 20 o C 12 4.13 x 10 -7 at 20 o C 4

4.5 x 10 -7 at 20 o C 12

Henry’s Law Constant (atm-m 3 /mole) 4.86 x 10 -7 at 20 o C (estimated) 5 1.8 x 10 -7 at 20 o C 4

2.11 x 10 -7 at 25 o C 3 0.037 (estimated) 7

Water Solubility (mg/L) 0.93 5 1.0 (PAI) 12, 13 1.0 at pH 6.5 4

2 7 1.0 (PAI) 12, 13 780 10

Log octanol-to-water partition coefficient (log K

ow ) >5.3 at 25 o C 5

4.5 at 20  C 2,12 4.5 at 20  C 3,12 3.18 7

1 Data that were not submitted in an MRID product chemis try study are not primary sour ces and in general, these data are not used in modeling. However, physico-ch emical properties are someti mes used when no primary data are available or better information is available from other sources. Primary data are shown in bold.

2 Data from TRED Case No. 2285 completed on August 11, 2004.

3 Data from EU Regulatory / Evaluation Data / EU Annex III PIC DGD: http://sitem.herts.ac.uk/aeru/pp db/en/Reports/324.htm (accesse d September 03, 2014).

4 Pesticide Manual (Combined File), 9 th & 10 th Ed., British Crop Protection Council, 1991 and the Royal Society of Chemistry, 1994, as reported in the United States Agricultural Research Service (ARS) handbook at: http://www.ars.usda.gov/Serv ices/docs.htm?docid=14199 (accessed August 28, 2014).

5 Data from MRID 47272601 and are provisional values pending complete review of the study.

6 Agrochemicals Handbook, 2 nd Edition, RSC, Nottingham, UK. 1987 as reported in the U.S. Agricultural Research Service (ARS) handbook at: http://www.ars.usda.gov/Services/docs.htm?docid=14199 (accessed August 28, 2014).

4 Fluazifop-acid is considered non-volatile based on criteria described in Corbin et al. 2006; however, pesticides with vapor pressures of 0.83 and 0.024 mPa, near the estimated vapor pressure of fluazifop-acid, have been found in remote environments, indicating that they underwent atmospheric transport and are semi-volatile (Daly et al . 2007;

Gouin et al. 2004).

### Page 15 of 78 7 Data from National Library of Medicine, ChemIDplus at http://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp (accessed August 28, 2014). Value is re ported for racemic fluazifop-acid.

8 An environmental fate summary (From Will Garner 03/24/ 1982) reported that the pKa of fluazifop-acid was

2.7.

9 Reported by registrant in metabolism study, see MRID 46190602.

10 Based on criteria in FAO 2000. (pH not reported)

11 PAI = Pure Active Ingredient; TGAI = Te chnical Grade of th e Active Ingredient.

12 Data from MRID 92067999 (2004). The data has been reviewed by USEPA Health Effects Division. 13 Solubility at both pH 5.0 (buffered water) and pH 6.5 (pure water).

### Page 16 of 78 

## 4.4. Environmental Fate and Transport

Abiotic Degradation

Abiotic degradation rates for flu azifop-butyl and fluazifop-p-butyl are similar. Hydrolysis rates for fluazifop-butyl and fluazifop- p-butyl decreased with pH, where half-life of fluazifop-p-butyl at pH 9 is 0.4 days, 78 days at pH 7 and showed no degradation at pH 5 (MRID 41598001). Conversely, fluazifop-acid and flu azifop-p-acid showed no signs of degradation by hydrolysis in water (Negre et al. 1988; MRID 46190601). Fluazifop-butyl and fluazifop-p-butyl were essentially stable to photolysis in so il (MRID 93788, 93789, 41598002). No acceptable study is available for the photolysis of both fluazifop- butyl and fluazifop-p-but yl in water, but a supplemental study showed fluazifop-p-acid with a half-life of 16.3 days (MRID 49188701). Overall, these results indicate that degradation from physical proce sses will play a minor role in fluazifop-butyl and fluazifop-acid degradati on because microbial degradation rates were substantially faster than the chemical degradation rates.

Biotic Degradation

Fluazifop-butyl and Fluazifop-p-butyl Aerobic and anaerobic degradation of fluazif op-butyl and fluazifop- p-butyl can be rapid, especially in moist soils and aer obic aquatic systems. Both compounds were shown to degrade rapidly in soil studies within 2 hours to less than 2 days (MRID 87493, 92067033, 162455, 46190605; Smith 1987). Degradation of fluazif op-butyl may be slow er from aerobic and anaerobic processes in some soils under drier conditions, probably because of decreased microbial activity (Negre et al . 1988; Smith 1987). The primary degradation pathway is via microbially mediated hydrolysis (Figure 2). Over all, these results indicate that in most use scenarios, soils, and aerobic condi tions, fluazifop-butyl and fluazif op-p-butyl will rapidly (within 2 hours) hydrolyze to the correspond ing fluazifop-acid (MRID 87493, 46190605, 162455); However, when the soil is dry or has little microbial activity, it will degrade more slowly.

Fluazifop-acid and Fluazifop-p-acid The primary mechanism of degradation for fluazi fop-p-acid and fluazifop- acid is also aerobic degradation, primarily through mi crobially-mediated hydrolysis of the ester linkage between the fluazifop and the butyric acid. Further degrada tion break the ether linka ges between the rings and the propanoic acid moiety. Anaerobic degrad ation occurs at a slower rate than aerobic

metabolism. Half-lives of flu azifop-p-acid and fluazif op-acid in aerobic soils ranged from 2 - 12 days (MRID 46190602, 87493, 92067032; Kah et al. 2007). 5 

### In an aerobic water-sediment metabolism study, half-lives of fluazifop-p- acid ranged from 13.7 – 108 days (MRID 46190605). On the other hand, the half-lives of the racemic mi xture of fluazifop-acid in an anaerobic flooded soil study ranged from 49 – 186 days (MRID 87493, 92067033). All aerobic and anaerobic soil and aquatic metabolism studies are summarized in Table 6, 7, and 8.

5 These half-lives include half-lives calculated using th e total residues of the flu azifop-butyl + fluazifop-acid because not enough data was available to estimate degrada tion of the parent and these were the supplemental values established for use in risk assessment (DER addendum 10/26/2003).

### Page 17 of 78 Figure 2. Degradation Pathway of Fluazifop-p-Butyl The names of compounds are available on Table 5 and can be identified by the number in parentheses. Transient degradates include quinol (VI) and benzoquinone (VII)



### Field Studies

Terrestrial field dissipation studi es indicate that degradation of fluazifop-butyl and fluazifop-pbutyl in soil are highly variable and may be pH dependent and substantially influenced by soil type. Fluazifop-p-butyl may rapi dly degrade or remain in soil up to 13 days and fluazifop-acid has the potential to persist in soil for days to weeks.

Dissipation of fluazifop- butyl was examined in four supplem ental terrestrial field dissipation studies including five di fferent locations or soils. With the exception of one study, fluazifop-pbutyl and fluazifop-butyl half-liv es ranged from rapid degradation at time 0 to 1.5 days (MRIDs 41598003, 41900605, 87495, 49193104). However, one field study conducted on a plot of sandy loam soil planted with cotton in California show ed fluazifop-butyl with a half-life of 13 days (MRID 41598004), which is considerably longer than the laboratory studie s or the other field dissipation studies would suggest . Although there is no evidence that climate, enantiomerselectivity, or soil pH played a role in this study, drier condi tions and precipitation amount may have contributed to the longer half-life of flu azifop-butyl in the Calif ornia study. The studies (I)

Further degradation
to CO 2 

### (X)

(VII) (VI) (IV) (III) (II) N C O OC H CH 3

C F

F O

O C H 2 C H 2 C H 2 C H F

N C O OC H CH 3

C F

F O

OH F

NH F 3 C O

N F 3 C O OH OH O H C

CH

3 C

OH O

O O O H HO

### Page 18 of 78 

### MRIDs 41900605 and 49193104 documented a combined rainfall and irrigation of 33 inches and 98.2 inches, respectively for the duration of the studies. Conversely, MRID 41598004 only showed a combined rainfall and irrigation of onl y 15.9 inches, which was substantially less than

the amount the other two studies re ceived. Thus, the result from this study may be regarded as a low-end field dissipation half -life for fluazifop-butyl.

Further, two of the above studies are considered supplemental due to the fact that the soil was rototilled after application (MRIDs 41598003 a nd 41900605). These studies are considered as having a great deal of uncertainty because rototi lling confounds the routes of dissipation and the results cannot be used to understand leaching; however, the estimates reported may be considered as a lower bound of potential field di ssipation for fluazifop- butyl and fluazifop-acid and provide information on what is expected in fields that are ro totilled after application. The

results from these studies are su mmarized in Table 6 and 7.

Degradates

The most significant degradates of fluazifop-p- butyl and fluazifop-butyl are fluazifop-acid and fluazifop-p-acid. Fluazifop-aci d, enantiomer unspecified, reached maximums of 70.2 to 90.3% of total radioactivity recovered in aerobic so il and anaerobic flooded soil metabolism studies with maximums occurring between 2 and 315 days. Fluazifop-p-acid reached maximums of 8.5 to 97.8% of applied equivalents or total radioactivity recovere d in metabolism studies with maximums occurring between 2 and 30 days. Othe r major degradates that were measured at greater than ten percent of a pplied equivalents or total radi oactivity recove red includes 2- hydroxy-5-trifluoromethylpyridine (degradate X) , 4-(5-Trifluoromethylpyr idin-2-yloxy) phenol (degradate IV), SYN546933, and R201189. The ma ximum concentrations of these compounds

are summarized in Table 5.

Half-lives of both fluazifop-acid and degradate X are greater than half-lives for fluazifop-butyl. The dissipation half-lives reported for fluazifop- acid in an acceptable field study ranged from 1.5 to 2.08 days in a bare plot after 3 applications, 2.3 to 2.73 days after 2 applications in a soybean cropped plot and 2.35 to 23.3 days in the soybean leaf disks after 2 applications. Meanwhile, degradate X was reported to have the calculated half-life of 339 days at the bare plot and 224 days at the soybean cropped plot (MRID 49193104). Half-lives of fluazifop-acid from other submitted field studies classified as supplemental ranged from 5 to 83 days. These studies may still be considered as a lower-end of poten tial field dissipation for fluazifop-acid.Page 19 of 784.5 Transformation ProductsSix degradates were measured at greater than ten percent of applied equivalents or total radioactivity recovered including, fluazifop-acid,fluazifop-p-acid, 2-hydroxy-5-trifluoromethylpyridine (degradate X), 4-(5-Trifluoromethylpyridin-2-yloxy)phenol (degradate IV),SYN546933, and R201189.Table 5lists the degradates of fluazifop-p-butyl, including their maximum and final concentrations, carbondioxide, residues that are well sorbed to soil, andan unidentified compound similar to diclofop-methyl.Table 5. Fluazifop-p-butyl and Its Environmental Transformation Products.ACode Name/SynonymChemical NameChemical StructureStudyGuidelineMRIDSystemMaximum%AR (day)Final %AR(studylength)PARENTFluazifop-p-butylIUPAC:butyl (R)-2-{4-[5-(trifluoromethyl)-2-pyridyloxy]phenoxy}propionateCAS No.:79241-46-6Formula:C19H20F3NO4MW:383.36 g/molSMILES:n1cc(C(F)(F)F)ccc1Oc2ccc(OC(C)C(=O)OCCCC)cc2MAJOR (>10%) TRANSFORMATION PRODUCTSFluazifop-p-acidIUPAC:(R)-2-(4-((5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propanoic acidFormula:C15H12F3NO4MW:327.26 g/molSMILES:O=C(O)[C@H](Oc2ccc(Oc1ncc(cc1)C(F)(F)F)cc2)C835.2120 41598001pH 724.1%(30 d)22.1%(30 d)pH 979%(2.9 d)78.6%(3 d)835.4100 87493 clay loam83.4%(2 d)0.6% (45 d)835.2410 41598002 irradiated 9.1% (30 d)9.1% (30 d)835.4200 87493 clay loam70.8%(315 d)70.8%(315 d)835.4300 46190605water96.7%(1 d) ND (100 d)total system97.8%(2 d)22.3%(100 d)835.6100 49193104Bare plot120.7%(0 d) ND (478 d)Cropped plot115.7%(0 d) ND (478 d)NCFFFOO CCH3COO CH2CH2CH2CH3HPage 20 of 78Code Name/SynonymChemical NameChemical StructureStudyGuidelineMRIDSystemMaximum%AR (day)Final %AR(studylength)Degradate X /Compound X /R154719 /CGA 142110IUPAC:5-(Trifluoromethyl)pyridin-2-olCAS:5-(trifluoromethyl)-2(1H)-pyridinoneCAS No.:33252-63-0Formula:C6H4F3NOMW:163 g/molSMILES:c1cc(ncc1C(F)(F)F)O835.2410 41598002 irradiated 2.0% (20 d)1.8% (30 d)835.4100 87493 sandy loam25.1%(84 d) 9.8% (315 d)835.4300 46190605water33.3%(59 d)26.9%(100 d)total system37.4%(59 d)29.6%(100 d)835.6100 49193104bare plot20.6%(7 d)3.6% (478 d)cropped plot25.8%(13 d)ND (478 d)Degradate IV /CGA181847 /R150397IUPAC:4-(5-Trifluoromethylpyridin-2-yloxy)phenolCAS No:69045-85-8Formula:C12H8F3NO2MW:255.20 g/molSMILES:nlcc(C(F)(F)F)ccc1Oc2ccc(O)cc2835.2240 49188701 irradiated31.6%(21 d)21.2%(35 d)835.4300 46190605sediment 9.9% (59 d) 4.9% (100 d)total system 9.9% (59 d) 4.9% (100 d)Degradate IIIIUPAC:2-(4-Hydroxyphenoxy)propionic acidFormula:C9H12O4CAS No.:67648-61-7MW:182.17 g/molNA NA NA NA NAR201189Formula:C14H10F3NO3SMILES:C1=C(C=NC(=C1)OC2=CC=C(C=C2)OC(C)=O)C(F)(F)F835.2240 49188701 irradiated12.9%(8 d) 4.7% (35 d)SYN546933Formula:C6H4F3NOSMILES:C1(=CC2C1C(N2[H])=O)C(F)(F)F835.2240 49188701 irradiated16.1%(28 d)14.1%(30 d)UnidentifiedcompoundsNANA835.2240 49188701 irradiated11.6% (35 d)11.6% (35 d)835.4100 46190602Sandy clayloam23.4% (30 d)21.4% (59 d)835.4300 46190605 Total system 8.0% (100 d) 8.0% (100 d)OH OHCCH3COHONF3C O OHNHF3C OPage 21 of 78Code Name/SynonymChemical NameChemical StructureStudyGuidelineMRIDSystemMaximum%AR (day)Final %AR(studylength)Carbon dioxideIUPAC:Carbon dioxideFormula:CO2MW:44 g/molSMILES:C(=O)=O835.4100 49010602 Loam17.0%(14 d)17.0%(14 d)835.4300 46190605 Total system32.0%(100 d)32.0%(100 d)UnextractedresiduesNA NA835.4100 49010602 Loam82.4%(4 d)76.24 %(14 d)835.4100 87493 clay loam55.4%(84 d)49.4%(315 d)835.4200 87493 sandy loam14.4%(315 d)14.4%(315 d)835.4300 46190605 Total system39.6%(100 d)39.6%(100 d)AAR means “applied radioactivity”. MW means “molecular weight”. LOD means “limit of detection”. NA means “not applicable”.

### Page 22 of 78 

### Mobility

Fluazifop-p-butyl No acceptable studies on sorption of fluazifop-p- butyl and fluazifop-butyl have been submitted. However, in a supplemental terrestrial field dissi pation study, fluazifop-p- butyl was not detected (level of quantitation 1.0 ppb) under the depth of 3 inches at both sand bare plot and sand soybean cropped plot in Georgia during the 13 days sampling intervals with 3 applications (MRID 49193104).

Fluazifop-p-Acid

Measured K F 

### values for fluazifop-p-acid ranged from 0.27 to 13.4 L/kg and K OC 

### values of 25.93 – 310.8 across various soils, indicatin g that fluazifop-p-acid is m obile to moderately mobile (classification based on FAO 2000; MRID 46190603; Kah and Brown 2007).

Adsorption appeared to be relate d to pH, with increasing sorpti on at lower pH’s (pH of soils ranged from 5.3-6.8) most likely due to the associ ation state of the acid and the pH-dependent cation exchange capacity of most so ils. As fluazifop-p-acid and fl uazifop-acid will be present in the anionic form at most environmental pH valu es, they are expected to be highly mobile. Anions (negatively-charged ions) tend to be weakly sorbed to mo st soils (in effect, repelled by soil matrix surfaces which are ge nerally negatively charged). Ge nerally speaking, other factors being the same, mobility is expect ed to decrease with pH for aci dic/anionic compounds as more of the compound will be pres ent in its neutral form.

These results suggest that fluazifop-p-acid has the potential to leach into groundwater and this is consistent with observation of leaching in the field dissipation studies (MRIDs 49193104 and 41598004).

Degradate X All applied 14 

### C labeled degradate X was measured in wa ter in batch equilibrium studies with a sand, two sandy loam soils, and a clay soil (M RID 41900604). A terrestrial field dissipation study in Tift County Georgia sand bare plot det ected the presence of degradate X (1.4 ppb) at 12- 18 inch soil depth on day 450, although samples be low the depth of 18 inch was not analyzed (MRID 41598004). Additionally, a recent suppleme ntal adsorption and desorption study, was performed on two U.S. soils and two British soil s indicated that degradate X is highly mobile

with the K OC 

### range of 17-37 L/kg-OC (MRID 49193101). Thus , based on its measured half-lives of 108 to 339 days in terrestrial fi eld dissipation studies, its mobilit y, and its propensity to stay in water, degradate X has the potential to move into groundwater (MRID 41900605, 49193104).

### Page 23 of 78 

### Bioconcentration/Bioaccumulation

Bioconcentration was examined in bluegill sunfis h and channel catfish. Bioconcentration factors in bluegill sunfish are summarized in Table 6 and ranged from approximately 200 to 400. 14 

### Cconcentrations in tissue fell ra pidly after exposure was stopped with greater than 97 percent eliminated during depuration. Bioconcentratio n/bioaccumulation is not expected to be a significant route of exposure beca use depuration occurs rapidly a nd bioconcentration factors are

low.

In a study examining bioconcentration in channel catfish, radiolabeled ( 14 

### C-phenyl and 14 

### Cpyridyl) fluazifop-butyl was applie d at 0.5 kg a.i./ha to a loamy sa nd soil. After 14 days aerobic incubation, the soil was flooded and channel catfish ( Ictalurus punctatus ) were added to the system for an exposure period of up to 65 days . After 28 and 65 days exposure, fish were transferred to flowing, uncontaminated water for 14 and 21 days, respectively. Soil, water, and fish (muscle, viscera, and whole fish) were analyzed for 14 

### C-residues at regular intervals. In the whole fish, the maximum bioconcentrati on factor (BCF=concentration in fish tissue/concentration in water) measured was 2.1, equal to 0.07 mg fluazifop-acid equivalents/kg wet weight the maximum muscle and viscer a bioconcentration factors were 1.1 and 8.0, respectively. The concentration of 14 

### C-residues in the fish fell rapidly during depuration with

over 70% of the residues elim inated during depuration.

Table 6, Table 7, and Table 8 summarizes the environmental fa te properties and studies of fluazifop-p-butyl, fluazifop- butyl, fluazifop-p-acid, fluazi fop acid, and degradate X.

### Page 24 of 78

Table 6

. Summary of Environmental Fate St udies for Fluazifop-p-butyl and Fluazifop-butyl 1

MRI D Number

or Reference (Year) Study Type Media Half

- Life

Fluazifop

- p

- butyl Fluazifop

- butyl

41598001 (1989) Hydrolysis Buffered water pH 5: N o evidence of degradation pH 7: 78 days pH 9: 0.4 days --

41598002 (1989) Soil Photolysis Loam soil

, 25°C 195 days

-- 87493 (1981) 4
92067032 (1990) 4
92067033 (1990) 4 Aerobic soil Sandy loam, 18 Acres

, 20°C, pH 6.0 Calcareous clay loam, Gore Hill ; 20°C pH 7.4 Loamy sand, Frensham

, 20°C, pH 5.4 Fen peat, Rosedean

, 20°C, pH 6.7 -- 1.94 days 9

<2 days 2

<2 days 2

<2 days 2

162455 (1984) 4, 8 Aerobic soil Sandy loam

, British soil 2 hours; S

- form also 2 hours

--

46190605 (1999) 4 Aerobic aquatic

metabolism Water/sand sediment from England Water pH 7.75 Sand sediment pH 5.5

Water/sandy loam system from England

Water pH 7.6 Sandy loam sediment pH 8.1 <2 hours

<4 hours --

87493 (1981) 4
92067032 (1990) 4
92067033 (1990) 4 Anaerobic

flooded soil All British Soils

, 20  C

, pH 6.0

- 7.4 Sandy loam, 18 Acres Calcareous clay loam, Gore Hill -- < 2

– 2 days

41598003

41900605 (1989) 5 Terrestrial Field

Dissipation P lanted with cotton in Visalia, CA Sandy loam (pH 7.3) Loam soil (pH 7.2) -- 1.5 days

1.5 days

41598004 (1989) Terrestrial Field

Dissipation Sandy loam soil planted with cotton from
Porterville, CA ; (pH 7.4

- 8.1) -- 13 days

87495 (1981) 92067034 (1990) Terrestrial Field

Dissipation Sandy loam pH 5.6 of Goldsboro, NC

Silty clay loam pH 6.0 from Champaign, IL Fine sandy loam pH 8.4 of Visalia, CA Silty loam pH 5.7 from Vicksburg, MS -- Undetected at time 0

Undetected at time 0

Undetected at time 0

Undetected at time 0Page 25 of 78MRID Numberor Reference(Year)Study TypeMediaHalf-LifeFluazifop-p-butylFluazifop-butyl49193104 (2013) Terrestrial FieldDissipationTift County, GASand, pH 6.3, Bare plotSand, pH 7.2, Soybean cropped plot<2.0% at time 0<2.0% at time 0--9379692067035 (1990)7Fishbioconcentrationfactors (steadystate, totalresidues);depuration rateBluegill SunfishWhole FishMuscleVisceraWater-- 97% depuration in 3 days240-410 BCF25- 20 BCF1400-4800 BCF610-70%1Abbreviations: DER = data evaluation record; DT50 = dissipation time of 50% of the chemical2AnEFED Fate summary dated 2/17/1982 estimateda half-life less than 2 days because that was the earliest sampling point after application, the data evaluationrecord (DER) completed on 10/26/1992indicated the results supported a half-life of less than a day.3The values shown are the half-life ± the standard error.4Soils were classified using the British classification system.5The plots in these studies were rototilled for weed control after the application of fluazifop-butyl and, in some cases, residues could not be found or were foundin much reduced levels after rototilling. The values in these studies may be considered a lower bound for rates of dissipation.6The study showed minimal bioconcentration of total radioactivity which provides a conservative estimate of bioconcentration offluazifop-p-butyl and fluazifopp-acid.7As only some of the residues in the viscera were fluazifop-acid, actual bioconcentration factors will be lower.8In Review: Study results are provisionalas reviews are currently in progress.9Calculated half-life of parent + acid in both pyridyl and phenyl labels.Page 26 of 78Table 7. Summary of Environmental Fate Studies for Fluazifop-p-acid and Fluazifop-acid1MRID Number orReference (Year)Study TypeMedia Half-LifeFluazifop-p-acid Fluazifop-acid46190601 (1995) Hydrolysis Sterile buffered solution, 25°C pH 5: No evidence of degradationpH 7: No evidence of degradationpH 9: No evidence of degradation--49188701 (2013) Aqueous Photolysis Sterile water 25°C, pH 7 16.3 days --87493 (1981)392067032 (1990)3Aerobic soilSandy loam, 18 Acres, 20°C, pH 6.0Calcareous clay loam, Gore Hill 20°C,pH 7.4Loamy sand, Frensham, 20°C, pH 5.4Fen peat, Rosedean, 20°C, pH 6.7-- 2.03 days22.6 days22.47 days(parent + acid)25.48 days23.78 days(parent + acid210.7 days211.9 days(parent + acid)246190602 (1998) Aerobic soilSilt loam, pH 7.0, 20°CSandy clay loam, pH 5.8, 20°CSandy loam, pH 7.2, 20°CSandy loam, pH 5.3, 20°CSandy clay loam, pH 7.1, 20°CClay loam, pH 7.7, 20°CLinear:10.5d; Nonlinear DT50: 8.3dLinear: 9.8d; Nonlinear DT50: 8.2dLinear: 7.5d; Nonlinear DT50: 2.7dLinear:13.9d; Nonlinear DT50: 9.1dLinear: 9.6d; Nonlinear DT50: 3.3dLinear: 9.1d; Nonlinear DT50: 2.3d--46190605 (1999)3Aerobic watersedimentWater/sand sediment from EnglandWater pH 7.75Sand sediment pH 5.5Water/sandy loam system fromEnglandWater pH 7.6Sandy loam sediment pH 8.1Phenyl label; Linear = 108 d (7-100day data); Observed DT50 = 100 dPyridyl label; Linear = 13.7 dObserved DT50 = 30-59 dPhenyl label; Linear = 23.2 dObserved DT50 = 30-59 dPyridyl label; Linear = 43.9 dObserved DT50 = 30-59 d--87493 (1981)392067033 (1990)3Anaerobicflooded soilSandy loam, 18 Acres, 20C, pH 6.0-- 49 days247 days(parent + acid)2Page 27 of 78MRID Number orReference (Year)Study TypeMedia Half-LifeFluazifop-p-acid Fluazifop-acidCalcareous clay loam, Gore Hill,20C, pH 7.4186 days2152 days(parent + acid)246190603 (1998)3Leaching &Adsorption(ADS)Silt loam (Soil A)Sandy clay loam (Soil B)Sandy loam (Soil C)Sandy loam (Soil D)Sandy clay loam (Soil E)Clay loam/ loam (Soil F)Koc: 80.3 L/kgKoc: 63.3 L/kgKoc: 200.4 L/kgKoc: 111.8 L/kgKoc: 139.3 L/kgKoc: 310.8 L/kg--4159800341900605(1989)Terrestrial FieldDissipationPlanted with cotton in Visalia, CASandy loam (pH 7.3)Loam soil (pH 7.2)--18 days18 days41598004 (1989) Terrestrial FieldDissipationSandy loam soil planted with cottonfrom CA (pH 7.4-8.1)-- 42 daysNo leaching of residues below 6” depth87495 (1981)92067034 (1990)Terrestrial FieldDissipationSandy loam pH 5.6, Goldsboro, NCSilty clay loam pH 6.0,Champaign, ILFine sandy loam pH 8.4, Visalia, CASilty loam pH 5.7, Vicksburg, MS-- 7-14 days7-14 days7-14 days7-14 days49193104 (2013) Terrestrial FieldDissipationTift County, GASand, pH 6.3, Bare plotSand, pH 7.2, Soybean cropped plotSoybean leaf disk1.5 - 2.08 days2.3 - 2.73 days2.35 – 23.3 days (tR IORE)--9379692067035(1990)Fishbioconcentrationfactors (steadystate, totalresidues);depuration rateBluegill SunfishVisceraWater--43-45%15-48%1Abbreviations: DER = data evaluation record; DT50 = dissipation time of 50% of the chemical2The half-life was calculated using single first-order on the combination of both phenyl & pyridyl labels.3All British Soils. Soils were classifiedusing the British classification system.Page 28 of 78Table 8. Summary of Environmental Fate Studies for Degradate X1Abbreviations: DER = data evaluation record; DT50 = dissipation time of 50% of the chemical2The plots in these studies were rototilled for weed control after the application of fluazifop-butyl and, in some cases, residues could not be found or were foundin much reduced levels after rototilling. The values in these studies may be considered a lower bound for rates of dissipation.3The dissipation of the degradate 5-trifluoromethyl-pyrid-2-one (degradate X) does not agree with the data reported in the aerobic metabolism and mobilitylaboratory studies (A. Abramovitch; EFED Fate Summary 11/9/1992; DP Barcode D157692, D157723, D165770). However, the study maybe considered alower bound for rates of dissipation.4All British Soils. Soils were classifiedusing the British classification system.MRID Number orReference (Year)Study TypeMediaHalf-LifeDegradate X87493 (1981)4Aerobic soilSandy loam, 18 Acres, 20°C, pH 6.0Calcareous clay loam, Gore Hill 20°C, pH 7.457.5 days34.3 days49193101 (1998) Adsorption & Desorption ERTC Sandy loam, pH 6.0; Whitakers, North CarolinaHyde Farm Sandy clay loam, pH 7.5; Berkshire, UKKenny Hill Sandy loam, pH 8.5; Suffolk, UKNRTC Silty clay, pH 5.6; NRTC, IllinoisKoc: 33 L/kgKoc: 17 L/kgKoc: 17 ± 4.6 L/kgKoc: 37 L/kg41598003 (1989)241900605 (1990)Terrestrial FieldDissipationSandy loam, (pH 7.3)Loam soil, (pH 7.2)108 days108 days41900606 (1990)3Terrestrial FieldDissipationSandy loam soil, (pH 7.1); planted with cotton 241 days49193104 (2013) Terrestrial FieldDissipationGA Sand, pH 6.3, Bare plotGA Sand , pH 7.2, Soybean cropped plot339 days(1.4 ppb detected at 12-18” depth on day 450)204 days

### Page 29 of 78 

# 5. Receptors

Consistent with EFED’s standard methodology, th e risk assessment for fluazifop will rely on a surrogate species approach. Toxi cological data generated from su rrogate test species, which are intended to be representative of broad taxonomic groups, are used to ex trapolate to potential effects on a variety of species (receptors ) included under these taxonomic groupings.

The Agency evaluates the potential for adverse eff ects as a result of fluazifop usage. The most sensitive endpoint for each taxon is used for RQ calculations. Assessment endpoints include

direct toxic effects on the surviv al, reproduction, and growth of te rrestrial and aquatic life, as well as indirect effects, such as reduction in prey base and/or modification of habitat. The evaluated taxa include freshwater fish, freshwat er aquatic invertebrates, birds, small mammals, terrestrial invertebrates, alg ae, and terrestrial plants.

Acute (short-term) and chronic (long-term) toxi city information is characterized based on registrant-submitted studies. Other sources of information, including use of the acute probit dose response relationship to establish the probability of an individual effect and reviews of the Ecological Incident Information System (E IIS), are conducted to further refine the characterization of potential ecological effects associated with exposure to fluazifop.

Estuarine/marine invertebrates are the most sensitiv e aquatic species. Fluazifop-p-butyl is highly acutely toxic to th e Pacific oyster ( Crassostrea gigas ), with a 48-hr EC 50 

### value of 0.083 mg acid equivalents (ae)/L. Fluazifop-p-but yl is highly toxic to freshwat er fish, with a reported 96-hr LC50 value of 0.45 mg ae/L to the Bluegill Sunfish ( Lepomis macrochirus ). Fluazifop-p-butyl is moderately toxic to freshwater invertebrates a nd estuarine/marine fish with a reported 48-hr EC 50 

### value of 5.14 mg ae/L to the Water Flea ( Daphnia magna ), and a reported 96-hr LC50 of 6.87mg ae/L to the Sheepshead Minnow ( Cyprinodon variegatus ) respectively. In 2 studies submitted and currently under review, Degradate X was less toxic to Rainbow trout as well as Daphnia (96- hr LC50 value of 240 mg/L and 48-hr EC 50 

### value of 666 mg/L, respectively).

Chronic exposure studies identified a freshw ater invertebrate 21-d LOAEC value of 0.213 mg

ae/L for D. magna and a freshwater fish 30-d LOAEC value of 0.203 mg ae/L for the Fathead Minnow ( Pimephales promelas )

. No acceptable data were submitted for chronic toxicity to

estuarine/marine fish or invert ebrates. Therefore, an ACR 6 

### value was obtained from the freshwater animal studies and applied to the acut e toxicity data for estuarine/marine species to estimate chronic toxicity values for these spec ies. This approach yielded a NOAEC value of 3.10 mg ae/L for the estuarine/marine fish C. variegatus and a NOAEC value of 0.003 mg ae/L

for the estuarine/marine invertebrate C gigas

.

In birds, the acute oral LD 50 

### for Anas platyrhynchos is 3012 mg/kg-bw and the avian dietary

LC 50 

### value is 4141 mg/kg-bw, practically nontoxic a nd slightly toxic, respectively. The avian reproductive toxicity data using Colinus virginianus and A. platyrhynchos resulted in NOAELs of 50 ppm and LOAELs of >50 ppm for fluazifop- butyl in both studies (no effects in either study). In laboratory rats, fluazifop-p-butyl has a dos e based acute toxicity LD 50 

### value of 2451

6 Acute toxicity endpoint value ÷ Chronic toxicity endpoint value

### Page 30 of 78 

### mg/kg-bw (practically non-toxi c) and a 2-generation reproduc tion study using fluazifop-butyl resulted in a NOAEL value of 80 ppm with reducti ons in pup weights as well as reductions in pup viability at 250 ppm

. Fluazifop-p-butyl is slightly to xic to the honey bee with an acute

contact LD 50 

### of 63 μg/bee.

No toxicity data have been submitted regarding the t oxicity of fluazifop-p-butyl or acid to plants. Risks to monocot plants are presumed due to th e fact that fluazifop- p-butyl is a selective herbicide intended to control monocot plants. Ri sks to dicot aquatic plan ts may be minimal due

to the fact that it is used routinely on dicot plant crops and no incidents of damage to these species have been reported. However, guidelin e toxicity studies woul d allow EFED to make

more definitive risk conclusions regarding dicot and monocot plan ts. Risks to algae and lichens are presumed to be a concern in the absence of data. Two studies (veget ative vigor and seedling emergence) have been recently submitted and are in review. Preliminary results suggest effects only to monocots.

Table 9 and Table 10 provide a summary of the aquatic and terrestrial ta xonomic groups, respectively, and most sensitive surrogate species tested to characterize the potential acute and chronic ecological effects of fluazifop.



## 5.1. Effects to Aquatic Organisms

Table 9. Summary of the Most Sensitive Endp oints from Aquatic Toxicity Studies for fluazifop-p-butyl or fluazifop-butyl

Taxonomic

Group Study Type Surrogate Species Toxicity

Value (mg ai/L) Acute Toxicity

Classification Source

Freshwater fish AcuteFluazifopbutyl Bluegill sunfish (Lepomis macrochirus) 96 hr LC 50 = 0.45 ppm Highly toxic 00087485,

1981

Acute Deg X Rainbow Trout (Oncorhynchus mykiss) 96 hr LC 50 = 240 ppm Practically

non-toxic 49224402,

1994 (IN REVIEW)

ChronicFluazifopbutyl Fathead minnow (Pimephales promelas) NOAEC= 0.203 ppm N/A 00093808,

1981

Freshwater

invertebrates AcuteFluazifopbutyl Water Flea ( Daphnia magna ) 48 hr EC 50 = 5.14 ppm Moderately

toxic 00087489,

1980

Acute Deg X Water Flea ( Daphnia magna ) 48 hr EC 50 = 666 ppm Practically

non-toxic 49224401,

1982 (IN REVIEW)

ChronicFluazifopbutyl Water Flea ( Daphnia magna ) LOAEC= 0.213 ppm N/A 00093807,

1981

### Page 31 of 78 Taxonomic

Group Study Type Surrogate Species Toxicity

Value (mg ai/L) Acute Toxicity

Classification Source

Estuarine/marine

fish AcuteFluazifopbutyl 46.8% Sheepshead Minnow ( Cyprinodon variegatus ) 96 hr LC 50 = 6.8 ppm Moderately

toxic 00152173,

1985

Chronic Sheepshead Minnow ( Cyprinodon variegatus ) No data N/A NA

Estuarine/marine

invertebrates AcuteFluazifop-pbutyl Mysid Shrimp ( Americamysis

bahia )

Eastern Oyster ( Crassostrea virginica ) 96 hr LC 50 = 0.435 ppm

96 hr EC 50 = 0.40 ppm Highly toxic

Highly toxic 42543201,

1991

41900601,

1991

Chronic Mysid Shrimp No data N/A N/A

Aquatic plants and algae Vascular Deg X 72 hr static Green Algae (Selenastrum capricornutum ) EC50 = 340

ppm (biomass)

NOAEL= 100 ppm

LOAEL = 200 ppm IN REVIEW 49224403,

1994

Vascular Green Algae ( Pseudokirchneriella subcapitata ) No inhibition

>50% N/A 41900603,

1985



## 5.2. Effects to Terrestrial Organisms

Table 10. Summary of the Most Sensitive Endp oints from Terrestrial Toxicity Studies for fluazifop-p-butyl

Taxonomic

Group Study Type Surrogate Species Toxicity Value (all units in terms

of measured active ingredient) Acute Toxicity

Classification Source

Birds Acute Mallard duck (Anas platyrhynchos) Acute Oral LD 50 > 3012 mg ai/kg-bw Practically

non-toxic 40829201,

1985

Sub-acute dietary Mallard duck (Anas platyrhynchos) Acute Dietary LC 50 4141.5 ppm Slightly toxic 00087481,

1987

Chronic Northern

Bobwhite (Colinus virginianus) NOAEL = 50 ppm LOAEL >50 ppm Fluazifop-butyl (no effects) N/A 00093802,

1981

### Page 32 of 78 Taxonomic

Group Study Type Surrogate Species Toxicity Value (all units in terms

of measured active ingredient) Acute Toxicity

Classification Source

Mallard duck (Anas platyrhynchos) NOAEL = 50 ppm LOAEL >50 ppm Fluazifop-butyl (no effects) N/A 00093801,

1981

Mammals Acute Oral Laboratory rat ( Rattus norvegicus ) LD 50 = 2451 mg/kgbw Practically

non-toxic 00162440,

1984

Acute

Inhalation Laboratory rat ( Rattus norvegicus ) LC 50 >2.3 mg/L N/A 46082901,

1979

Chronic Laboratory rat ( Rattus norvegicus ) NOAEL = 80 ppm LOAEL 250 ppm

with reductions in pup viablity and weights N/A 92067050,

1981

Insects Acute

contact Honey bee ( Apis mellifera

L. ) 48 hr LD50 = 63 ug/bee Slightly toxic 00162453,

1984

Terrestrialplants nontarget Seedling Emergence No data N/A N/A N/A

No data N/A N/A N/A

Vegetative Vigor No data N/A N/A N/A

No data N/A N/A N/A



## 5.3. Ecological Incidents

The ecological incident information system (EIIS ) is an OPP database that houses ecological incidents that have been repor ted to the Agency. When ava ilable, EIIS includes date and location of an incident, type and magnitude of effects observed in various species, use(s) of pesticides known or suspected of contributing to the inci dent, and results of any chemical residue analysis or other analyses conducted during in cident investigation. EIIS incidents are categorized according to the certai nty that the incident resulted from pesticide exposure. The Avian Monitoring System (AIMS) is a database administered by the Amer ican Bird Conservancy that contains publicly available data on reported avian incidents involving pesticides. Many of

the incidents listed in this data base are also in the EIIS.

Reported incidents from the EIIS database included damage to non- target terrestria l plants, sheep mortality and mortality to fish.

### Page 33 of 78 

### Table 11. EIIS Pesticide Summary Report for Fluazifop (122805)

Incident# Date County,

State Certainty Legal. Appl.

Method Species Response Rt. Exposure Magnitude

PLANTS

Peanuts I011838-

012 6/4/2001 Mitchel, GA 2 UN NR Peanuts Plant damage Treated directly 70 acres

Cotton I000031-

001 6/9/1992 LA 1 MA NR Cotton Plant damage Treated directly Unknown

Certainty code: 0=Unrelated, 1=Unlikely, 2=Possible, 3 =Pr obably, 4=Highly Probable Legality Code: RU=Registered Use, M=Mi suse, MA=Misuse (Accidental), MI=Mis use (Intentional), UN=Unknown, NR=Not Reported



### Table 12. EIIS Pesticide Summary Repo rt for Fluazifop-P-butyl (122809)

Incident# Date County,

State Certainty Legal. Appl.

Method Species Response Rt. Exposure Magnitude

AQUATIC

Soybean I007601-

001 7/23/1998 White, IL 2 RU Spray Catfish, crappie, bass,

sunfish Mortality Rain/Pond

Runoff 200

PLANTS

Soybean I007755-

022 6/15/1998 Clay, IN 2 UN NR Terrestrial

Plant Plant damage Treated directly 20 acres

Corn I012499-

024 5/24/2001 Cedar, IA 2 RU Broadcast Terrestrial

Plant Plant damage Treated directly 75 acres

Corn I012499-

031 5/22/2001 Carroll, IA 2 RU Broadcast Terrestrial

Plant Plant damage Treated directly 195 acres

Corn I012499-

038 5/30/2001 Ida, IA 2 RU NR Terrestrial

Plant Plant damage Treated directly 90 acres

Ornamen

tal I023931-

065 2012 Washten, MI 4 UN NR Terrestrial

Plant Plant damage Treated directly >45%

Ornamen

tal I024071-

265 2012 Oakland, MI 2 UN Spray Terrestrial

Plant Plant damage NR >45% of

Flowers

Residenti

al I024179-

100 2012 Spokane,WA 2 UN Spray Terrestrial

Plant Plant damage Treated directly >45% of plants

Residenti

al I024179-

170 2012 Yakima, WA 1 UN NR Terrestrial

Plant Plant damage NR 1 Ajuga Plant

Residenti

al I024272-

138 2012 Licking, OH 2 UN NR Terrestrial

Plant Plant damage NR >45% Evergreen

Residenti

al I024272-

187 2012 Roane, TN 2 UN NR Terrestrial

Plant Plant damage NR >45% Roses

Residenti

al I024272-

216 2012 New Haven,

CT 2 UN NR Terrestrial

Plant Plant damage NR >45% of

Plants
ANIMALS

Field I026002-

001 2013 IA 2 UN NR Terrestrial

Animal Mortality Drift 3 Sheep

Certainty code: 0=Unrelated, 1=Unlikely, 2=Possible, 3 =Pr obably, 4=Highly Probable Legality Code: RU=Registered Use, M=Mi suse, MA=Misuse (Accidental), MI=Mis use (Intentional), UN=Unknown, NR=Not Reported



# 6. Exposure Pathways of Concern

The conceptual model will consider the parent compound and its acid for the drinking water exposure assessment and ecological risk assessment.

The environmental fate properties and use patterns of fluazifop-p-butyl indi cate that direct spray, spray drift, leaching for areas with shallow gr ound water tables, and runoff represent potential transport mechanisms of fluazifop-p-butyl resi dues to aquatic and terrestrial organisms.

### Page 34 of 78 

### Drinking water and inhalation e xposure pathways were screen ed using the SIP (Screening Imbibition Program) and STIR (Screening Tool for Inhalation Risk) screening methods and were found not to be exposure pathways of concern (no LOC exceedances are expected). Appendix C

and D contain details on the SIP a nd STIR analyses. SIP and STIR are described in detail at: http://www.epa.gov/oppefed1/ models/terrestrial/index.htm

.



# 7. Analysis Plan

7.1. Stressors of Concern

Ecological Risk Assessment

A few different compounds are associated with the common name, fluazi fop-butyl. Fluazifopbutyl (PC Code 122805) is the racemic mixture ( e.g., consists of equal amounts of the R and S enantiomers) of butyl-2-{4-[5-(trifluoromet hyl)-2-pyridyloxy]phenoxy}propi onate, but has been cancelled. Fluazifop-p-butyl (PC Code 122809) is the R enantiomer and is more herbicidally active than the S enantiomer (Tu et al. 2001). Both primarily degrad e, via microbial mediated hydrolysis, in moist soil and sedi ments to fluazifop-acid which can also exist in the R or S form (MRID 162455; 87493, 92067033, 87492, 92067032, 46190602, 46190605).

Drinking Water Exposure Assessment

The drinking water exposure assessment conducted to support human hea lth risk assessment of fluazifop-p-butyl will incorpor ate model estimates of fluazif op-p-butyl residues of concern, which are the parent compound and its acid (USEPA, 2000), in surface and ground waters. Exposure estimates reported for potential acute, ch ronic, and cancer assess ment are the 1-in-10- year peak, 1-in-10-year annual m ean, and 30-year mean in a vulnerable reservoir with a drinking water intake. The fluazifop-p-butyl residues of concern may be reevaluated pending receipt and review of additional environmental fate and toxicity data.



## 7.2. Measures of Exposure

EFED will use standard available models to evaluate potential exposures to aquatic and terrestrial organisms as described at http://www.epa.gov/pesticides/science/models_db.htm . For surface water, the measure of exposure for acute risk s is the 1-in-10-year peak concentration at a site more vulnerable than 90% of sites where a pe sticide use site occurs. For chronic risks, the measures of exposure are 1-in-1 0-year 21-day and 60-day means. For terrestrial risks the measure of exposure is the peak exposure on (and at the e dge of) the field.



## 7.3. Measures of Effect

Toxicity data presented in Section 4 of this pr oblem formulation will be used to calculate risk quotients. Any additional information submitted by th e registrant or found in the open literature prior to conduct of the risk assessment will also be considered. The open literature studies are identified using EPA’s ECOTOXicol ogy database (ECOTOX) (USEPA, 2007 c ), which employs a literature search engine for lo cating chemical toxicity data for aquatic life, terrestrial plants,

### Page 35 of 78 

### and wildlife. The evaluation of both sources of da ta can also provide insi ght into the direct and indirect effects of pesticides on biotic communities from loss of species that are sensitive to the chemicals and from changes in structure and functional characteristics of the affected

communities.



# 8. Endangered Species Assessments

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 evaluating potential risks to listed species is further described at http://www.epa.gov/oppfead1/enda nger/litstatus/riskasses.htm

.



# 9. Endocrine Disruptor Screening Program

As required by FIFRA and FFDCA, EPA reviews num erous studies to asse ss potential adverse outcomes from exposure to chemicals. Collectiv ely, these studies includ e acute, subchronic and chronic toxicity, including asse ssments of carcinogenicity, ne urotoxicity, developmental, reproductive, and general or systemic toxicity. These studies include e ndpoints which may be susceptible to endocrine influe nce, including effects on endocri ne target organ histopathology, organ weights, estrus cyclicity, sexual maturatio n, fertility, pregnancy rates, reproductive loss, and sex ratios in offspring. For ecological hazard assessments, EPA evaluates acute tests and chronic studies that assess gr owth, developmental and reprod uctive effects in different taxonomic groups. As part of its most recent regi stration decision, EPA reviewed these data and selected the most sensitive endpoi nts for relevant risk assessment scenarios from the existing hazard database. However, as required by FFDCA s ection 408(p), fluazifop-p-butyl is subject to the endocrine screening part of the Endocri ne Disruptor Screeni ng Program (EDSP).

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

determinations. Tier 1 consists of a battery of 11 screening assays to identify the potential of a chemical substance to interact with the estrog en, androgen, or thyroid (E, A, or T) hormonal systems. Chemicals that go th rough Tier 1 screening and are found to have the potential to interact with E, A, or T hormonal systems will proceed to the next stag e of the EDSP where EPA will determine which, if any, of th e Tier 2 tests are necessary base d on the available data. Tier 2 testing is designed to identify a ny adverse endocrine-related eff ects caused by the substance, and establish a dose-response relationship between the dose and the E, A, or T effect.

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

### Page 36 of 78 

### of chemicals identified for EDSP sc reening was published on June 14, 2013 7 

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

. Neither of these lists

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

Fluazifop and Fluazifop-p-butyl ar e on List 1 for which EPA has re ceived all the required Tier 1 assay data. The Agency is currently reviewing all assay data received for the appropriate List 1 chemicals and planning to make the conclusions of those reviews availa ble in early 2015. For further information on the status of the EDSP, the policies and procedures, th e lists of chemicals, future lists, the test guidelines and the Tier 1 screening battery, please visit our website. 8

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

chemicals.

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

### Page 37 of 78 

# 10. Preliminary Identification of Data Gaps

10.1. Environmental Fate

Table 13 and 1 4 identify environmental fate studies by their Master Record Identification (MRID) number that offer data for each guideline requirement, as well as study classifications and whether or not further data are needed in order to support risk assessment.

Table 1 3

. Summary of fate data requirements for fluazifop

- p

- butyl and fluazifop

- p

- acid

.

Guideline

Number Study

Description 40 CFR 

### § 158

Requirements:

Terrestrial

Outdoor Use MRID

Number (chemical) 1 Classification Are more data

needed for this risk

assessment? Justification/Comments

Degradation Studies

– Laboratory

835.2120 Hydrolysis Required 41598001 (ester)

46190601 (acid) Acceptable

Acceptable No

835.2240 Photodegradation

in water Required 42543202 (ester)

49188701 (acid) Unacceptable

Supplemental No Not a major degradation pathway versus microbial degradation; ester is predicted not to readily photolize, similar to the acid

.

835.2410 Photodegradati on

on soil Required 41598002 (ester) Acceptable No T he ester study should sufficien tl y represent
the acid form

. 835.2370 Photodegradati on

in air Conditionally

required No data Not applicable No No d ue to low vapor pressure

Metabolism Studies

– Laboratory

835.4100 Aerobic soil Required 162455 ( ester )

49010602 ( degradate IV )

46190602 (acid) Not classified

In Review*

Supplemental No Although half

- life data is not available for

ester , stud ies has shown that ester rapidly degraded to acid form within 2 days . The data on acid would sufficiently describe the

fate of ester. Half

- li fe data on combined ester residue plus acid is available for the

racemic mixture.Page 38 of 78Table 13. Summary of fate data requirementsfor fluazifop-p-butyl and fluazifop-p-acid.GuidelineNumberStudyDescription40 CFR§ 158Requirements:TerrestrialOutdoor UseMRIDNumber(chemical)1ClassificationAre more dataneeded for this riskassessment?Justification/CommentsMRID46190602: Supplemental due toincomplete material balance andtransformation products not addressed835.4200 Anaerobic soil Required No data Not applicable No Flooded soil study data is available forracemic mixture(87493,92067032,92067033)835.4300 Aerobic aquatic Required 46190605 (ester+ acid)Acceptable No835.4400 Anaerobic aquatic Required No data Not applicable Yes An anaerobic aquatic metabolism study isrequired under 40 CFR Part 158. OCSPPguidance recommends that these tests beperformed with two sediments.Mobility Studies835.1230835.1240Leaching andadsorption/desorptionRequired 46190603 (acid)SupplementalYes for ester and acid For MRID 46190603, insufficient massbalance and no soil with <1% organicmatter. All soils were foreign soils. Onlyone soil values in the study can be used forrisk assessment.A new adsorption-desorption study isrequested with a minimum of five domesticsoils with one containing <1% organicmatter.46190604 (ester) Unacceptabledue to heatsterilized soils41900604 (acid)49010601( Degradate IV)Not classified49193101(Degradate X)Supplemental835.1410 Volatility –laboratoryConditionallyRequiredNo data Not applicable No Nodue to low vapor pressure835.8100 Volatility – Field ConditionallyrequiredNo data Not applicable No Nodue to low vapor pressureDissipation Studies - FieldPage 39 of 78Table 13. Summary of fate data requirementsfor fluazifop-p-butyl and fluazifop-p-acid.GuidelineNumberStudyDescription40 CFR§ 158Requirements:TerrestrialOutdoor UseMRIDNumber(chemical)1ClassificationAre more dataneeded for this riskassessment?Justification/Comments835.6100 Terrestrial Required 49193104 (ester+ acid +degradate X)Supplemental No Although study only use only one site, butstudy was conducted with a conservativeapproach. Additional site studies are notrequested because they are not expected tosubstantially change the values in riskassessment.This study is deemed supplemental due touncertainties in soil storage stability.(MRID 49193102).835.6200 Aquatic(sediment)ConditionallyrequiredNo data Not applicable No835.6300 Forestry Not required No data Not applicable No Forestry uses were not requested835.6400 Combination andtank mixesConditionallyrequiredNo data Not applicable NoGround Water Monitoring835.7100 Ground watermonitoringConditionallyrequiredNo data Not applicable NoOtherAnalyticalchemistrymethods capableof identifying andquantifying eachseparateenantiomer inwater49193108UnacceptableYesMethods to detect fluazifop-butyl,fluazifop-acid and othermajor degradates inwater are needed to support watermonitoring studies3,4Analyticalchemistrymethods capableof identifying andquantifying each49193107 Supplemental Yes Methods to detect fluazifop-butyl,fluazifop-acid and othermajor degradates insoil are needed to support monitoringstudies3Page 40 of 78Table 13. Summary of fate data requirementsfor fluazifop-p-butyl and fluazifop-p-acid.GuidelineNumberStudyDescription40 CFR§ 158Requirements:TerrestrialOutdoor UseMRIDNumber(chemical)1ClassificationAre more dataneeded for this riskassessment?Justification/Commentsseparateenantiomer in soilValidation ofAnalyticalMethod andIndependentlaboratoryvalidation ofparent andsignificantmetabolites forsoil and waterRequired forvalidation offield studies,e.g., water andsoil49193105Unacceptable Yes49193106Supplemental YesStorage stabilityof residues infrozen soilsamplesRequired 4919310249193103AcceptableAcceptableNoBioconcentrationin fishConditionallyRequiredNo data Not applicable No Data is available for racemic mixtureSpray droplet sizespectrum (201-1)Required. No data Not applicable NoData are available. May be satisfiedthrough membership in the Spray Drift TaskForce.Syngenta Crop Protection, Inc. is a memberof the Spray Drift Task Force5*In Review: Study results are provisional as reviews are currently in progress.1Ester refers to the parent compound, fluazifop-p-butyl,and acid refers to the acid degradate, fluazifop-p-acid.2EFED Interim Policy for Stereoisomeric Pesticides(available athttp://www.epa.gov/oppefed1/ecorisk_ders/stereoisomer_policy.htm) states, “...an aerobic soilmetabolism study (GLN 162-1/835.3300) is required as part of the minimal data setfor enantiomeric enriched mixtures.”3EFED Interim Policy for Stereoisomeric Pesticides(available athttp://www.epa.gov/oppefed1/ecorisk_ders/stereoisomer_policy.htm) states,“...Analyticalchemistry methods capable of identifying and quantifying each separate enantiomer and chiral transformation products in soil, water, and fish tissue are needed.”4A high-performance liquid chromatography (HPLC) method was submitted to detect fluazifop-acid in water in connection with a ground water monitoring studybut it has not been independently evaluated and did not examine the enantiomers present (MRID 40439402).5List of Spray Drift Task Force Members available athttp://www.agdrift.com/Text%20pages/members.htm(accessed March 28, 2008).Page 41 of 78Table 14. Summary of fate data requirementsfor fluazifop-butyl and fluazifop-acid.GuidelineNumberStudyDescription40 CFR§ 158Requirements:TerrestrialOutdoor UseMRIDNumber(chemical)1ClassificationAre more data neededfor this riskassessment?Justification/CommentsDegradation Studies – Laboratory835.2120 Hydrolysis Required 87529 Not classified No Data is available for fluazifop-p-butyl835.2240 Photodegradationin waterRequired 93788 Not classified No Data is available for fluazifop-p-butyl835.2410 Photodegradationon soilRequired 93789 Not classified No Data is available for fluazifop-p-butyl835.2370 Photodegradationin airConditionallyrequiredNot applicable No No due to low vapor pressureMetabolism Studies – Laboratory835.4100 Aerobic soil Required 87493,92067032,9206703387492SupplementalNot classifiedNo Soils used in the study were Englishsoils.835.4200 Anaerobic soil Required 87493,92067033Supplemental No Soils used in the study were Englishsoils.835.4300 Aerobic aquatic Required No data No dataNo Data is available for fluazifop-p-butyl835.4400 Anaerobic aquatic Required 87493,92067032Unacceptable NoMobility Studies835.1230835.1240Leaching andadsorption/desorptionRequired 9379441900604Not classifiedUnacceptabledue to heatsterilized soilsNoFluazifop-butyl is no longer registeredfor use.835.1410 Volatility –laboratoryConditionallyRequiredNo data Not applicable No835.8100 Volatility – Field ConditionallyrequiredNo data Not applicable NoDissipation Studies - Field835.6100 Terrestrial Required 41598003SupplementalNo Does not completely fulfill guidelinerequirements becauseof rototilling of soilPage 42 of 78Table 14. Summary of fate data requirementsfor fluazifop-butyl and fluazifop-acid.GuidelineNumberStudyDescription40 CFR§ 158Requirements:TerrestrialOutdoor UseMRIDNumber(chemical)1ClassificationAre more data neededfor this riskassessment?Justification/Comments4159800487495 &920670344190060541900606SupplementalSupplementalSupplementalUnacceptableSupplemental due to major degradateswere not monitored and the freezerstorage stability study was not adequateSupplemental due to inadequate samplingintervals, application rate not confirmed,and analytical methods were not providedDoes not completely fulfill guidelinerequirements becauseof rototilling of soilData not corresponding to aerobicmetabolism study on degradate amounts835.6200 Aquatic(sediment)ConditionallyrequiredNo data Not applicable No835.6300 Forestry Not required No data Not applicable No835.6400 Combination andtank mixesConditionallyrequiredNo data Not applicable NoGround Water Monitoring835.7100 Ground watermonitoringConditionallyrequired40439401 Unacceptable No. Fluazifop-butyl isno longer registered foruse.Unacceptable , due to non-targetedmonitoringOtherValidation ofAnalyticalMethod andIndependentlaboratoryvalidation ofparent andsignificantmetabolitesRequired forvalidation offield studies,e.g., water andsoil40439402 This method hasnot beenvalidatedNo Fluazifop-butyl is no longer registeredfor use.Page 43 of 78Table 14. Summary of fate data requirementsfor fluazifop-butyl and fluazifop-acid.GuidelineNumberStudyDescription40 CFR§ 158Requirements:TerrestrialOutdoor UseMRIDNumber(chemical)1ClassificationAre more data neededfor this riskassessment?Justification/CommentsStorage stabilityof residues infrozen soilsamplesRequired 4159800440439401Not classifiedNot classifiedNoA storage stability study for fluazifopbutyl for 1.25 months was completed inconnection with a terrestrial fielddissipation studyStorage stability study supporting groundwater monitoring study835.1730Bioconcentrationin fishConditionallyRequired93796 &9206703593795Supplementaldue to 45% ofdegradate inviscera notcharacterized.Not classifiedNo The study showed minimalbioconcentration of total radioactivitywhich provides a conservative estimateof bioconcentration of fluazifop-p-butyland fluazifop-p-acid.Spray droplet sizespectrum (201-1)Required. Dataare available.No data Not applicable No, Syngenta CropProtection, Inc. is amember of the SprayDrift Task Force5May be satisfied through membership inthe Spray Drift Task ForceList of Spray Drift Task Force Members available athttp://www.agdrift.com/Text%20pages/members.htm(accessed March 28, 2008)

### Page 44 of 78 

## 10.2. Ecological Effects

Table 15 and Table 16 identify ecological effects studies by MRID that offer data for each guideline requirement, as well as study classifications and whether or not further data are needed in order to support risk assessment. Rationale for the additional data requested is presented

below the tables.

Table 15. Submitted Aquatic Ecological Effects Data for fluazifop-p-butyl or fluazifopbutyl

OCSPP

Guideline Data Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to

conduct risk

assessment? Current Addition al Data Need

850.1010 Freshwater

invertebrate acute toxicity 00087489 Acceptable No

850.1025

850.1035

850.1045

850.1055 Saltwater

invertebrate acute toxicity 42543201 Acceptable No

41900601 Supplemental

850.1075 Freshwater fish acute toxicity 00087485 Acceptable No

00131458 Supplemental

850.1075 Saltwater fish acute toxicity 00152173 Acceptable No

850.1300 Freshwater

invertebrate life cycle 00093807 Acceptable No

850.1350 Saltwater

invertebrates life cycle No data N/A Yes See explanation below

850.1500 Freshwater fish life cycle N/A N/A No

850.1400 Freshwater fish early-life stage 00093808 Supplemental No

850.1400 Saltwater fish early-life stage No data N/A Yes See explanation below

850.4400 Aquatic plant growth: vascular plants N/A N/A No

850.4500 Aquatic Plant

Growth: algae 41900603

49224403 Invalid

In Review Yes

850.4550 Cyanobacteria(Anabaena flosaquae) N/A N/A No

### Page 45 of 78 

### Table 16. Submitted Terrestrial Ecological Effects Data for fluazifop-p-butyl

OCSPP

Guideline Data Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed for

risk

assessment? Current Additional Data Need

850.2100 Avian oral toxicity 40829201 Acceptable No

850.2200 Avian dietary toxicity 00087481 Acceptable No

40851401 Acceptable

850.2300 Avian reproduction 00093801

00093802 Supplemental Supplemental Yes See explanation below

850.3020 Honey bee

acute contact toxicity 00162453 Acceptable No

850.3030 Honey bee

residue on foliage N/A N/A No

850.3040 Field testing for pollinators N/A N/A No

850.4100 Terrestrial plant toxicity: seedling

emergence 49453801 In Review Yes See explanation below

850.4150 Terrestrial plant toxicity: vegetative vigor 49453802 In Review Yes See explanation below

Nonguideline Honeybee

larval oral N/A N/A Yes See explanation below

Nonguideline Honeybee

acute adult

oral N/A N/A Yes See explanation below

Nonguideline Honeybee

larval chronic N/A N/A Yes See explanation below

Nonguideline Honeybee

adult chronic N/A N/A Yes See explanation below



### At the present time, data are sufficient to support an ecological risk assessment except for

chronic estuarine/marine fish and invertebrate studies, terrestrial and aquatic plant toxicity studies, avian reproduction studies and acute/chronic adult oral and larval oral/chronic studies with the honeybee. Without these data, assumptions will be made which may be overly

conservative.

### Page 46 of 78 

### Avian Reproduction (850.2300) Avian Reproduction studies were submitted and revi ewed in 1982. These studies used technical fluazifop-butyl, which is now cancelled. There were a number of problems with these studies

which included deaths in the controls and ma ximum concentrations ( 50 ppm in both studies) were less than expected maximu m field residue exposure levels (in the current case 1.125 lbs ai/A x 240 ppm = 270 ppm). The SOP recommends te sting at concentrations equal to expected field residue levels. Testing should be done with Fluazifop-p acid, since Fluazifop-P-butyl is rapidly (less than one day) degraded in soil to fluazifop-p acid, which is much more stable in soil and water environments than the parent.



### Honeybee Toxicity (non-guideline) In keeping with the Agency’s proposed new para digm for determining potential adverse effects to insect pollinators from conve ntional pesticides (USEPA 2012) , additional studies are being requested in addition to the acute contact study already submitted. Even though contact to fluazifop-p-butyl is slightly toxic to honeybees, an adult acute oral toxicity study (following OECD 213) and a larval toxicity study (following OECD 237) ar e necessary to evaluate the potential for fluazifop-p-butyl an d/or acid to adversel y affect bees and other pollinators through other routes of exposure. In addition, adult and larval chronic studi es are being requested. Several of the treated crop areas may be cons idered attractive to hone y bees and this is a systemic chemical that is transported throughout th e plant. Thus, residues may be available to pollinators via pollen and/or nectar.

Terrestrial Plant Toxicity (850.4100 and 850.4150) Fluazifop-p-butyl is a post-emergent system ic aryloxyphenoxypropionic herbicide to control perennial and annual grass weeds. In general, it has little effect on broad-leaved plants (dicots) (Ware and Whitacre 2004). Fluazifop-p-butyl is re gistered to control mo nocot plant species and there are reported incidents in EFED’s Ecological Incident Info rmation System (EIIS) database where crop damage was reported on corn, which is a monocot species. There are no data to assess risks to terrestrial plants. Tier I seed ling emergence and vegetative vigor studies are needed. Testing should be done with Fluazifop-p- butyl which degrades ra pidly in soil (under 2 hrs) into fluazifop-p acid, both toxic components of herbicidal activity. Two studies (vegetative vigor and seedling emergence) have been rece ntly submitted and are in review. Preliminary results suggest effects to monocots only.

Estuarine/Marine Fish and Invertebrates (850.1350 and 850.1400) No data have been submitted regard ing chronic toxicity to estuarine/ marine fish or invertebrates. Fluazifop is highly acutely toxic to freshwater fi sh and invertebrates. In addition, use on golf

courses can occur near estuarine areas. Tes ting should be done usi ng fluazifop-p acid.

Aquatic Plant Toxicity (850.4400, 850.4500 & 850.4550) Aquatic plant testing is required for any herbicide that has outdoor non-residential terrestrial uses that may move off-site by runoff, by drift, or that is applied direct ly to water. Two aquatic plant

studies have been submitted and one was deemed invalid. The second study used metabolite X and is currently in review. Tier II testi ng should be done usin g fluazifop-p acid.

### Page 47 of 78 

# 11. References

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and Effects Division to the Re gistration Division. May. 25, 2010.

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Bees. Submitted to the FIFRA Scientific Advisory Panel for Review and Comment September 11-14, 2012. Office of Chemical Sa fety and Pollution Prevention Office of Pesticide Programs Environmental Fate and Effects Division, Environmental Protection Agency, Washington DC; Environmental Asse ssment Directorate, Pest Management Regulatory Agency, Health Canada, Ottawa, CN; California Department of Pesticide Regulation. www.regulations.gov/#!documentD etail;D=EPA-HQ-OPP-2012-0543-0004

United States Geological Survey (USGS). 2014. National Water-Quality Assessment (NAWQA) Program, Pesticide National Synthesis Pr oject, Pesticide Us e Maps – Diclofop. http://water.usgs.gov/nawqa/pnsp/usage/ maps/show_map.php?year=2011&map=FLUAZ IFOP&hilo=L&disp=Fluazifop (accessed Aug. 13, 2014)

### Page 51 of 78 

# APPENDIX A: Eco and Fate Bibliography for Fluazifop

122809 Fluzifop p butyl Eco Effects Bibliography

71-1 Avian Singl e Dose Oral Toxicity

MRID Citation Reference

40829201 Roberts, N. (1985) The Acute Oral Toxicity of Fluazifop-p-butyl to the Mallard Duck: Project ID: CTL/P/1375. Unpublished study prepared by Huntingdon Research Center. 35 p.

92068004 Edwards, P. (1990) ICI Americ as Inc. Phase 3 Summary of MRID 40829201. The Acute Toxicity (LD50) of Fluazifop-p-butyl (PP005) to the Mallard Duck: Report No. CTL/C/1375; Study No. ICI36BT/841263. Prepared by Huntingdon Research Centre. 10 p.



## 71-2 Avia n Dietary Toxicity

MRID Citation Reference

40859401 Roberts, N. (1985) The Subacute Dietary Toxicity of Fluazifop-p-butyl to the Bobwhite Quail: Laboratory Project ID CTL/P/1410. Unpublished study prepared by Huntingdon Research Center. 35 p.

41199201 Roberts, N.; Fairley, C.; Ander son, A.; et al. (1987) CTL/C/1379-- The Subacute Dietary Toxicity of Fluaz ifop-P-Buty (sic) to the Mallard Duck: HRC Report No. ISN 37BT/841262. Unpublished study prepared by Huntingdon Research Centre. 36 p.

92068005 Edwards, P. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40859401. The Subacute Dietary Toxicity (LC50) of Fluazifop-p-butyl (PP005) to the Bobwhite Quail: Report No. CTL/C/1410; Study No. ISN/35BT/ 841280. Prepared by Hunt ingdon Research Centre. 11 p.

87481 Ross, D.B.; Roberts, N.L.; Phillips, C.N.K.; et al. (1980) The Subacute Dietary Toxicity (LCI50^) of PP 009 to the Mallard Duck: ISK/ICI WL 284/79835. (Unpublished study received Dec 4, 1981 under 10182-EX-27; prepared by Huntingdon Research Centre, England, submitted by ICI Americas, Inc ., Wilmington, Del.; CDL: 246386-C) PP009= fluzifop butyl



## 71-4 Avian Reproduction

93801 Roberts, N.L.; Phillips, C.N.K.; Woodhouse, R.N.; et al. (1981) The Effect of Dietary Inclusion of Fluazifop Butyl on Reproduction in the Mallard Duck: ISK/ICI 286/8144; CTL/C/1071. Final rept. (Unpublished study received Jan 18, 1982 under 10182-66; prepared by Huntingdon

### Page 52 of 78 Research Centre, England, subm itted by ICI Americas, Inc., Wilmington, Del.; CDL:070630-B)

93802 Roberts, N.L.; Phillips, C.N.K.; Almond, R.H.; et al. (1981) Fluazifop Butyl: The Effect of Dietary Inclusion on Reproduction in the Bobwhite Quail: ISK/ICI 287/81209; CTL/C/1092. Final rept. (Unpublished study received Jan 18, 1982 under 10182 -66; prepared by Huntingdon Research Centre, England, subm itted by ICI Americas, Inc., Wilmington, Del.; CDL:070630-C)



## 81-1 Acute oral toxicity in rats

MRID Citation Reference

143669 Southwood, J. (1984) Fluazifop-P- Butyl: 125g/1 EC Formulation: Acute Oral Toxicity and Acute Dermal Toxicity Studies: Report No.: CTL/P/1008. Unpublished study prepared by Imperial Chemical Industries Plc. 67 p.

161774 Pritchard, V. (1986) Fluazifop-p-butyl: Acute Oral and Dermal Toxicity of an EC Formulation to the Rat: Report No. CT L/P/1428. Unpublished study prepared by Imperial Chemical Industries Ltd. 45 p.

162440 Southwood, J. (1984) R Isomer of Fl uazifop-butyl (PP005): Acute Oral and Acute Dermal Toxicity Studies: Report No. CTL/ P/755: CTL Study Nos. AR3092, CB1504. Unpublished study prepared by Industrial Chemical Industries PLC, Central Toxicology Laboratory. 67 p.

40439201 Barber, J. (1987) Fluazifop-P-Butyl/Fome safen: Acute Oral Toxicity to the Rat of a 0.75/1.0 lb/US gal Formulation: Rept. No . CTL/P/ 1971. Unpublished study prepared by Imperial Chemical Industries, Ltd. 27 p.

41917902 Keenan, K. (1991) Acute Oral Toxicity Te st of Fluazifop-P-butyl/Fenoxaprop-P-ethyl 2- 0.56 EC: Lab Project Number: T-14076. Un- published study prepared by ICI Americas, Inc. 33 p.

42518002 Glaza, S. (1991) Acute Oral Toxicity Study of CC-16799 in Rats: Final Report: Lab Project Number: HWI 10907490: 91-53. Unpublished study prepared by Hazleton Wisconsin, Inc. 27 p.

42700801 Keenan, K. (1993) Fluazifop-P-Butyl 4E C: Acute Oral Toxicity Test: Lab Project Number: RR 93-017B: T-15910. Unpublished study prepared by Zeneca Ag Products, Western Research Center. 38 p.

42729402 Keenan, K. (1993) Fluazifop-P-Butyl 2E C: Acute Oral Toxicity Test: Lab Project Number: T-15914: RR 93-014B. Unpublished study prepared by Zeneca Ag Products. 30 p.

42841901 Duerden, L. (1993) Fluazifop-P-butyl: Ac ute Oral Toxicity to the Rat of A 240g/l ME Formulation: Lab Project Number: CTL/P/3942: AR5495. Unpublished study prepared by Zeneca Central Toxicology Lab. 37 p.

43662803 Kuhn, J. (1995) Acute Oral Toxicity St udy in Rats: Chemsico Grass & Weed Killer M: Final Report: Lab Project Number: 1859-95. Unpublished study prepared by Stillmeadow, Inc. 24 p.

43708503 Wnorowski, G. (1995) Acute Oral Toxici ty Limit Test (Rat): Chemsico Grass & Weed Killer Z: Lab Project Number: 3547: P320: E 50214-1H. Unpublished study prepared by Product Safety Labs. 15 p.

### Page 53 of 78 44036702 Robinson, P. (1996) Twister: Fomesafe n/Fenoxaprop/Fluazifop-p-Butyl: Acute (Oral) Toxicity Study in Rats of a 130.78/19. 22/68.42 g/L ME Formulation: Lab Project Number: AR6174: CTL/P/4931. Unpublished study prepared by Zeneca Central Toxicology Lab. 73 p.

45892203 Moore, G. (2003) Acute Oral Toxicity Up and Down Procedure in Rats: Chemsico Herbicide Concentrate DFC (Alternate II): Lab Project Number: 13124: P320. Unpublished study prepared by Product Safety Labs. 15 p. {OPPTS 870.1100}

45918903 Merkel, D. (2002) Acute Oral Toxicity St udy in Rats--Limit Test: Chemsico Herbicide RTU DFC: Lab Project Number: 12138: P320. Unpublished study prepared by Product Safety Labs. 15 p. {OPPTS 870.1100}

92068008 McCall, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00162440. R-Isomer of Fluazifop-butyl (PP005): Acute Oral Toxi city to the Rat: CTL Report No. CTL/P/755; CTL Study No. AR3092. Prepared by ICI Central Toxicology Laboratory. 7 p.



## 72-1 Acute Toxicity to Freshwater Fish

MRID Citation Reference

40829202 In Review Hill, R. (1985) PP005: Dete rmination of the Acute Toxicity of a 25% w/w Formulation to Rainbow Trout (Salmo gairdneri): Project ID: BL/B/2525. Unpublished study prep ared by Imperial Chemical Industries PLC. 21 p.

40829203 In Review Hill, R. (1985) PP005: Dete rmination of Acute Toxicity of a 25% w/w Formulation to Bluegill Sunfish (Le pomis macrochirus): Project ID: BL/B/2526. Unpublished study prep ared by Imperial Chemical Industries PLC. 21 p.

40829204 In Review Hill, R. (1985) PP005: De termination of Acute Toxicity of a 125 g/l Formulation to Rainbow Trout (Salmo gairdneri): Project ID: BL/B2553. Unpublished study prepared by Imperial Chemical Industries PLC. 21

p.

40829205

49224402 In Review

In Review Hill, R. (1985) PP005: Determinatio n of Acute Toxicity of a 125 g/l Formulation to Bluegill Sunfish (Le pomis macrochirus): Project ID: BL/B-2554. Unpublished study pr epare by Imperial Chemical Industries PLC. 20 p.

Sankey, S.; Caunter, J.; Morris, D. (1994) R154719-Acute Toxicity to
Rainbow Trout (Oncorhynchus mykiss): Final Report. Project
Number: BL5216/B. Unpublished study prepared by Imperial
Chemical Industries, Ltd./Zeneca. 20p.

131458 Hill, R.; Maddock, B.; Com ber, M. (1983) Fluazifop-butyl: Determination of the Acute Toxicity to Rainbow Trout (Salmo gairdneri): Brixham Study No. J371/ B; Brixham Report No. BL/B/2244. (Unpublished study received Oct 6, 1983 under 10182-67; prepared by Imperial Chemical Industries PLC, Eng., submitted by ICI Americas, Inc., Wilmington, DE; CDL:251454-C)

92068006 Treacy, C. (1990) ICI Americ as Inc. Phase 3 Summary of MRID 00131458. Fluazifop-P-butyl (P005): Determination of the Acute

### Page 54 of 78 Toxicity of the Active Ingredient 93 .7% w/w to Rainbow Trout (Salmo gairdneri): Report No. BL/B/2244; Study No. J 371/B. Prepared by ICI Brixham Laboratory. 11 p.

87483 Hill, R.W.; Maddock, B.G.; Harland, B.J. (1981) Determination of the Acute Toxicity of PP009 to Rainbow Trout (Salmo gairdneri):
BL/B/2036. Includes undated method entitled: Determination of PP 009 in water samples from fish bioassay studies. (Unpublished study received Dec 4, 1981 under 10182-EX-27; pre- pared by Imperial Chemical Industries, Ltd., England, submitted by ICI Americas, Inc., Wilmington, Del.; CDL:246386-E) PP009= fluizifop butyl



## 72-2 Acute Toxicity to Freshwater Invertebrates

MRID Citation Reference

162451 Hamer, M.; Hill, I. (1983) PP005: Toxicity of the Technical Material and Formulations JF8906 and JF8908 to First Instar Daphnia magna: Report Series: RJ 0312B. Unpublished study prepared by ICI Plant Protection Div., Jealotts Hill Research Station. 15 p.

Three different test materials

162452 Hamer, M.; Hill, I. (1983) Fluazifop: Toxicity of Different R:S

Enantiomer Ratios to First Instar Daphnia magna: Report Series: RJ 0315B. Unpublished study prepared by ICI Plant Protection Div., Jealotts Hill Research Station. 17 p.

40829206

49224401 In Review

In Review Farrelly, E.; Homer, M.; Hill, I. ( 1984) PP005: Toxicity of Formulations GFU 239A and GFU 324A to First Instar Daphnia magna: Project ID: RJ0376B. Unpublished study prepared by ICI Plant Protection Div. 16

p.

Hill, I.;Arnold, J.; Hamer, M. (1982) Fluazifop-P-Butyl 5-Trifluormethyl2-pyridone-Toxicity to First Instar Daphnia manga:Final Report. Project number RJ0252B. Unpublished study prepared by Imperial Chemical Industries. 12p.

92068007 Hamer, M. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00162451. Toxicity of the Technical Material and FormulationsIF8-906 and JF8909 to First Instar Daphnia magna: Report No. RJ0312; Study No. PP005/CN/01. Prepared by ICI Agrochemicals. 16 p.

92068042 Hamer, M. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00162452. Toxicity of Different R:S En antiomer Ratios to First Instar Daphna [sic] magna: Report No. RJ0315B; Study No. PP004/CN/01. Prepared by ICI Agrochemicals. 17 p.



## 72-3 Acute Toxicity to Estuarine/Marine Organisms

MRID Citation Reference

41900601 Dionne, E. (1991) (Fluazifop-p-But yl)-Acute Toxicity to Eastern Oyster (Crassostrea virginica) Under Fl ow-Through Conditions: Lab Project

### Page 55 of 78 Number: 91-4-3746: 1828.1190.6107.504. Unpublished study prepared by Springborn Labor atories, Inc. 57 p.

42543201 Willams, T.; Tapp, J.; Sankey, S. et al. (1991) Fluazifop-P-Butyl: Acute Toxicity to Mysid Shrimp (Mysidopsis bahia): Lab Project Number: BL4295/B. Unpublished study prepared by ICI Group Environmental Lab. 18 p.



## 72-4 Fish Early Life Stage/ Aquatic Invertebrate Life Cycle Study

MRID Citation Reference

41900602 Tapp, J.; Maddock, B.; Caunter, J.; et al. (1991) (Fluazifop-p-But- yl)- Chronic Toxicity to Fathead Minnow (Pimephales promelas) Embryos and Larvae: Lab Project Number: BL/4008/B: T820/A (FT95/ 90). Unpublished study prepared by ICI PLC Group Environmental Laboratory. 57 p.

93807 Edwards, P.J.; Brown, S.M.; Hamer, M.J.; et al. (1981) Fluazifop- butyl: 21 Day Daphnia magna Life-cycle Study: Report Series RJ 0209B. Final rept. (Unpublished study received Jan 18, 1982 under 10182-66; submitted by ICI Americas, Inc ., Wilmington, Del.; CDL:070630-H)



## 122-1 Seed Germination/Seedli ne Emergence and Vegetable Vigor

MRID Citation Reference

41555201 Rea, D.; Mannion, S.; Martin, E.; et al. (1989) PP005: Effects on the Plants in the Weed Science and Plant Growth Regulator Screens of the Biological Group: Lab Project Number: RJ 0501B. Unpublished study prepared by ICI Agrochem icals, Jealott's Hill. 23 p.

93811 Poole, N.J.; Collins, D.J.; Dalziel, J.; et al. (1981) Fluazifop- butyl, Fluazifop and 5-Trifluoromethyl-pyri d-2-one: Effects on the Arthropods, Nematodes, Micro-organisms and Plants Used in the Pesticide Screens: Report Series RJ 0214 B. Final rept. (Unpublished study received Jan 18, 1982 under 10182-66; sub- mitted by ICI Americas, Inc., Wilmington, Del.; CDL:070631-D)



## 122-2 Aquatic plant growth

MRID Citation Reference

41900603 Smyth, D.; Tapp, J.; Sankey, S.; et al. (1985) Fluazifopp-Butyl: Toxicity to the Green Alga Selenastrum capricornutum: Lab Project Number: BL4040/B: N280/B (FT11/85). Unpublished study prepared by ICI PLC Group Environmental Laboratory. 22 p.

### Page 56 of 78 49224403

In review Kent, S.; Sankey, S.; Smyth, D. (1994) Toxicity to the Green Alga Selenastrum capricornutum: Final Report. Project Number: BL5205/B. Unpublished study prepared by Imperial Chemical Industries, Ltd./Zeneca. 24p.



## 141-1 Honey bee acute contact

MRID Citation Reference

162453 Collins, I.; Gough, H .; Wilkinson, W. (1984) PP005: Acute Contact and Oral Toxicity to Honey Bees (Apis melifera): Report Series: RJ 0345B. Unpublished study prepared by ICI Plant Protection Div., Jealotts Hill Research Station. 19 p.

92068017 Lewis, G. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00162453. PP005: Acute Contact and Oral Toxicity to Honey Bees (Apis Mellifera): Report No. RJ0345B; Study No. PP005/CM/01. Prepared by ICI Agrochemicals. 13 p.


# Non Guideline Selections

147633 ICI Americas Inc. (1984) Toxi cology to Fish and Wildlife [with PP005 1E and 2E Herbicides]. Unpublished study. 6 p.



# Fate/Chemistry Bibliography

161-1 Hydrolysis

MRID Citation Reference

41598001 McCarron, E.; Heath, J. (1989) Fl uazifop-P-Butyl: Hydrolysis in Sterile Aqueous Solution: Lab Project Numb er: 89JH132. Unpublished study prepared by ICI Agrochemicals. 57 p.

46190601 Goodyear, A. (1995) (Carbon 14) -Fluazifop-P: Hydrolysis in Sterile Aqueous Solution: Final Report. Project Number: 38/187/1015, 38/187. Unpublished study prepared by Hazleton Uk. 78 p.



## 161-2 Photodegradation-water

MRID Citation Reference

### Page 57 of 78 42543202

49188701 In Review Jessup, K.; Embury, G.; Leahey, J. (1991) Fluazifop-P-Butyl: Photodegradation in Aqueous Solution at pH 5: Lab Project Number: RJ0992B. Unpublished study prepared by ICI Agrochemicals. 74 p.

Graham, R., T. Fletcher, and J. Gilbert. (2013) Fluazifop-P-Butyl. R156172 – Photodegradation of [14C ]Fluazifop-P, R156172, in Sterile Aqueous Solution. Final Report. Un published study performed by Smithers Vincient (ESG) Ltd, Harrogate, UK, and Convance Laboratories Ltd, Harrogate and Alnwick, UK; sponsored and submitted by Syngenta Crop Protection, LLC.



## 161-3 Photodegradation-soil

MRID Citation Reference

41598002 French, D.; Matharu, K. (1989) Fluazifop-P-Butyl: Photodegradation on a Soil Surface: Lab Project Number: 89JH269. Unpublished study prepared by ICI Agrochemicals. 99 p.



## 162 -1 Aerobic Soil Metabolism

87493
ACC 246387 Harvey, B.R., J. Vincent, R. Mistry and D.J. Arnold (1981) Fluazifopbutyl: Degradation in Soil. Unpublished Study Performed by ICI Agrochemicals, Bracknell, UK and Submitted by ICI Americas Inc., Wilmington, DE.

162455
ACC 252853 Bewick, D. (1983) Fluazifop-butyl: Fate of the Separate R and S-- Enantiomers in Soil: Report Series: RJ 0306B. Unpublished study prepared by ICI Plant Protection Div ., Jealotts Hill Research Station. 21 p.

87493

summary 92067032 Leahey, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00087493. Fluazifop-butyl: Degradation in Soil and a Comparison of the Microflora and Physicochemical Properties of Soils Used in UK Laboratory Studies with those of USA Soils: Report Nos. RJ0197B and RJ0429B; Study Nos. PP009AD02 and PP000CK10. Prepared by ICI Agrochemicals. 32 p.

162454
ACC 252853 Bewick, D. (1982) Fluazifop: St ereochemistry of Residues Derived from the Hydrolysis of Fluazifop-butyl in Soil: Report Series: RJ 0270B. Unpublished study prepared by ICI Plant Protection Div. 28 p.

46190602 Goodyear, A. (1998) (Carbon 14) -Fluazifop-P: Soil Degradation at 20 (Degrees) C: Final Report. Project Number: 38/200/D2142, 38/200. Unpublished study prepared by Co vance Laboratories, Ltd. 64 p.



## 162-2 Anaerobic Soil Metabolism

87493 Harvey, B.R.; Vincent, J.; Mistry , R.; et al. (1981) Fluazifop- butyl: Degradation in Soil: Report Series RJ 0197B. (Unpublished study received Dec 4, 1981 under 10182-EX-27; prepared by Imperial

### Page 58 of 78 Chemical Industries, Ltd., England, submitted by ICI Americas, Inc., Wilmington, Del.; CDL:246387-E)

92067033 Leahey, J.P. (1990b) Phase 3 Summary of MRID 87493. Fluazifopbutyl: Degradation in Soil and a Comparison of the Microflora and Physicochemical Properties of Soils used in UK Laboratory Studies with those of USA Soils. Report No. RJ0197B and RJ0429B. Anaerobic Soil Metabolism. Study No. PP009/AD0Z and PP000CK10. Unpublished Summary Prepared by ICI Agrochemicals, Bracknell, UK and Submitted by ICI America, Inc., Wilmington, DE.



## 162-4 Aerobic Aquatic Metabolism

46190605 Purser, D. (1988) (Carbon 14)-Fluazifop-p-Butyl: Degradation and Retention in Water Sediment System s: Fluazifop-P-Butyl: Final Report. Project Number: 38/232/D2142, 38/232. Unpublished study prepared by Covance Laboratories, Ltd. 130 p.



## 163-1 Leach/adsorp/desorption

MRID Citation Reference

41900604 Lane, M.; Vaughn, P. (1991) Fluazifop-p-Butyl: Adsorption and Desorption of Two Soil Metabolites, Fluazifop and R154719: Lab ProjectNumber: RJ0967B. Unpublished study prepared by ICI Agrochemicals. 50 p.

46190603 Goodyear, A. (1998) (Carbon 14)-Fluazifop-P: Adsorption/ Desorption in Soil: Final Report. Project Number: 38/197/D2142, 38/197. Unpublished study prepared by Co vance Laboratories, Ltd. 61 p.

46190604

49193101 In Review Ziegler, D. (1988) Adsorption of Fluazifop-Butyl to Loamy Sand, Loam, Silty Clay Loam, and Silt Loam: Fluazifop-p-Butyl: Final Report. Project Number: 1086. Unpublished study prepared by Analytical Development Corp., Inc. 66 p.

Lane, M.C.G. and D. Rowe. (1998) Fluazifop-P-Butyl - Adsorption and Desorption Properties of a Soil Metabolite Compound X (R154719) in Four Soils. Final Report. Unpublished study performed by ZENECA Agrochemicals, Jealott’s Hill Res earch Station, Berkshire, UK



## 164-1 Terrestrial field dissipation

MRID Citation Reference

41598003 Wiebe, L. (1989) Fusilade 2000: Field Dissipation Study for Terrestrial Uses: Visalia, California, 1989: Lab Project Number: FUSI -89-
SD-01: US02-89-211: 89-066B. U npublished study prepared by ICI Americas Inc. 129 p.

### Page 59 of 7841598004 Wiebe, L. (1989) Fusilade 2000: Field Dissipation Study for Terrestrial Uses Porterville, California , 1989: Lab Project Number: FUSI-89- SD-01: 94CA-89-212: RR 89-067B. Unpublished study pre- pared by ICI Americas Inc. 125 p.

41900605 Wiebe, L. (1990) Fusilade 2000: Field Dissipation Study for Terrestrial Uses Visalia, California, 1989-1990: Lab Project Number: RR 90- 337B. Unpublished study prepared by ICI Americas Inc. 188 p.

41900606 Wiebe, L. (1990) Fusilade 2000: Field Dissipation Study for Terrestrial Uses Porterville, California, 1989-1990: Lab Project Numb- er: RR 90-338B. Unpublished study prepared by ICI Americas Inc. 177 p.

87495 Ussary, J.P.; Koubek, K.G.; Theodo rakis, S.K.; et al. (1981) Fluazifopbutyl Dissipation in Soils: Report Series TMU0657/B. (Unpublished study received Dec 4, 1981 under 10182-EX-27; sub- mitted by ICI Americas, Inc., Wilmington, Del.; CDL:246387-G)

92076034

49193104 In Review Iwata, Y. (1990) Phase 3 Summary of MRID 87495. Fusilade Field Dissipation Study for Terrestrial Uses. Unpublished Summary Submitted by ICI Amreicas Inc., Richmond, CA.

Wiepke, T., Jacobson, B., Hagan, M., and Bertrand, N. (2013) Fluazifop-P-butyl – Dissipation of Fluazifop-P-Butyl EC (240) in SoilUnder Soybean Production Conditions and Agricultural Fallow/NonCrop Land Use Conditions in the Southeastern United States. Final Report. Unpublished study performed by Syngenta Crop Protection,
LLC.



## 165-4 Fish Bioaccumulation

No MRID Bull, J.M., E.A. Curl and I.R. H ill (1981) Fluzifopbutyl: Accumulation in Bluegill Sunfish in a Flow-Through System. Unpublished Study Performed by ICI Agrochemicals, Br acknell, UK and Submitted by ICI Americas, Inc. Wilmington, DE.

93976 ? OPPIN shows different Citation for this MRID

92067035 Hamer, M.J. (1990) Summary of MRID 00093976

. Fluazifopbutyl: Accumulation in Bluegill Sunfish in a Flow-Through System. Unpublished Summary Document Prepared by ICI Agrochemicals, Bracknell, UK and Submitted by IC I Americas Inc., Wilmington, DE.



## 166-1 Ground water-small prospective

MRID Citation Reference

46190605 Purser, D. (1988) (Carbon 14)-Fluazifop -p-Butyl: Degradation and Retention in Water Sediment Systems: Fluazifop-P-Butyl: Fi nal Report. Project Number: 38/232/D2142, 38/232. Unpublished study prepared by Covance Laboratories, Ltd. 130 p.



## 171-4B Residue Analytical Methods

### Page 60 of 78 MRID Citation Reference

40361102 French, D.; Leahey, J. (1987) Fluazi fop-P-butyl: Determination of Radioactive Residues in Grapes from a Vine Treated with 2 Basal Applications of [Carbon 14]- Fluazifop-P-butyl: Lab. Proj. ID RJ0569B. Unpublished study prepared by ICI Plant Protection Div., Jealott's H ill Research Station. 21 p.

40361103 Harradine, K. (1984) The Detection of Re sidues of Total Fluazifop (Fluazifop-Butyl, Fluazifop and Conjugate Esters): In Crops - A Nuclear Magnetic Resonance Spectroscopic Method: Resi due Analytical Method No. 83. Unpublished study prepared by ICI Plant Protection Div., J ealott's Hill Research Station. 15 p.

40704805 Watford, S.; Francis, P. (1987) Supplement ... Fluazifop-p- butyl: Fluazifop Residues in Plum and Prune Samples (1986): Laboratory Project ID: TMU3311/B. Unpublished study prepared by ICI Americas Inc. 6 p.

40831307 Hayward, G. (1987) The Determination of Residues of Total Fluazifop (Fluazifop-pButyl, Fluazifop and Conjugate Esters) in Oily Crops: Project ID: Analytical Method No. 122. Unpublished study prepared by ICI Plant Protection Div. 22 p.

41041501 Malhorta, R. (1989) Analysis of Fluazifo p-p-butyl and Fluazifop Residues by Analytical

Methods in FDA Pesticide Manual Vol.1: HAS A030.001. Unpublished study prepared by Huntington Analytical Services. 146 p.

92068020 Bussey, R. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40831303 and Related MRIDs 40831305, 40831304, 00152494, 00151494, 40361110, 40704805. FUSILADE Residue Analytical Method: Labo ratory No. RR-90-098B. Prepared by ICI Agricultural Experiment Station. 14 p.

92068021 Atreya, N. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00093843. The Determination of Residues of Fluazifop-P-butyl and Fluazifop Free and Lipophilic Conjugates in Milk and Bovine Tissues - A high Pressure liquid Chromatography and Gas Chromatography - Mass Spectrometry Method: Report No. Plant Protection Division Analytical Method (PPRAM) No . 61; Study No. PP009BA01. Prepared by ICI Agrochemicals. 16 p.

92068040 Atreya, N. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00093845. The Determination of Residues of Fluazifop-but yl (PP009): Fluazifop and Conjugate Esters of Fluazifop in Eggs and Chicken Tissue: Pl ant Protection Division Residue Analytical Method (PPRAM) No. 58. Prepared by ICI Agrochemicals. 17 p.

92068041 Atreya, N. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40831310. The Determination of Residues of 5-Trifluoromethyl-2- pyridone (Reference X) in Crops - A Nuclear Magnetic Resonance Spectrosc opic Method: Plant Protection Division Residue Analytical Method (PPRAM) No. 103. Prepared by ICI Agrochemicals. 12 p.

92068043

49193107

49193106 Bussey, R. (1990) ICI Americas Inc. Phase 3 Reformat of MRID 40831303 and Related MRIDs 40831304, 40831305, 40831307, 00152494, 00151494, 40361110, 40704805. FUSILADE Residue Analytical Method: Laboratory Study ID No. RR 90- 103B. Prepared by ICI Americas, Inc. 120 p.

Huang, S.-B. (2010) Fluazifop-P-Butyl: GRM044.03A - Analytical Method for the Determination of Fluazifop-P-Butyl (R15 4875; PP5), Fluazifop-P-Acid (R156172) and Compound X (R154719; CGA142110) in Soil Using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS): Anal ytical Method Amendment. Prepared by Syngenta Crop Protection, LLC.

Perez, R., J. L. Schmitt. (2013) Fluazifo p-P-Butyl: Fluazifop-P-Butyl - Independent Laboratory Validation of Analytical Meth od (GRM044.03A) for the Determination of Fluazifop-P-Butyl (R154875; PP5), Fl uazifop-P-Acid (R156172), Compound X

### Page 61 of 78 (R154719; CGA142110) in Soil Using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS): Final Report . Prepared by ADPEN Laboratories, Inc.



## 171-4C Magnitude of the Residue [by commodity]

MRID Citation Reference

151494 ICI Americas, Inc. (1985) Fusilade 2000 1E Herbicide (Containing Fluazifop-P-Butyl): Amendment of Tolerance Petition for Onions: Residue Chemistry: [Includes Response to EPA's Commnents and Comparative Study of Residues in Onions with Fluazifop-PButyl/ Fluzaifop-Butyl]. Unpublished compilation. 65 p.

162047 Morgan, J.; Crook, S. (1986) Fluazifop-p- butyl: Residues in Onions from Trials Carried out in the U.S.A. during 1984: Report Se ries M4266B. Unpublished study prepared by ICI Plant Protection Div. 29 p.

162447 ICI Americas, Inc. (1984) Residue Chem istry: Registration Applica- tion for Cotton and Soybeans: PP005 2E Herbicide (Contai ning Fluazifop-P-butyl). Unpublished compilation. 70 p.

40140401 Hayward, G. (1987) Fluazifop-P-Butyl: Storage Stability of Residues in Deep Frozen Onion Samples: [Interim Report]: Lab. Proj . ID M4429B. Unpublished study prepared by ICI Agricultural Experiment Station. 13 p.

40294002 Hayward, G. (1987) Fluazifop-p-butyl (R eference X): Storage Stability of Residues in Deep Frozen Onion Samples: Laboratory Project ID: M4544B. Unpublished study prepared by ICI Plant Protection Division. 14 p.

40361104 Trumbo, K.; Francis, P. (1986) Fluazifo p-butyl: Storage Stability of Residues in Deep Frozen Tomato Samples: Lab. Proj. ID TMU 3079. Unpublished study prepared by ICI Americas Inc. 12 p.

40361106 Watford, S.; Francis, P. (1986) Residue Levels of Fluazifop in Apples: Lab. Proj. ID TMU3119/B. Unpublished study prepared by ICI Americas Inc. 16 p.

40361107 Watford, S.; Francis, P. (1987) Fluazi fop-P-butyl: Fluazifop Residues in Apple Samples: Lab. Proj. ID TMU3291/B. Unpublished study prepared by ICI Americas Inc. 35 p.

40361108 Watford, S.; Francis, P. (1987) Fluazi fop-P-butyl: Residue Levels of Fluazifop in Cherries (PP005) 1986: Lab. Proj. ID TMU3 181/B. Unpublished study prepared by ICI Americas Inc. 43 p.

40361109 Watford, S.; Francis, P. (1987) Fluazi fop-P-butyl: Residue Levels of Fluazifop in Peaches (PP005) 1986: Lab. Proj. ID TMU3 168/B. Unpublished study prepared by ICI Americas Inc. 38 p.

40361110 Watford, S.; Francis, P. (1987) Fluazifo p-P-butyl: Fluazifop Residues in Plum and Prune Samples (1986): Lab. Proj. ID TMU33 11/B. Unpublished study prepared by ICI Americas Inc. 48 p.

40361111 Watford, S.; Francis, P. (1987) Fluazi fop-P-butyl: Fluazifop Residues in Pecans (1985): Lab. Proj. ID TMU3251/B. Unpublish ed study prepared by ICI Americas Inc. 16

p.

40361112 Watford, S.; Francis, P. (1987) Fluazifop- P-butyl: Fluazifop-P- butyl Residues in Grape Samples: Lab. Proj. ID TMU3330/B. Unpublished study prepared by ICI Americas Inc. 26 p.

### Page 62 of 78 40361113 Watford, S.; Francis, P. (1987) Fluazi fop-P-butyl: Residue Levels of Fluazifop on Grapes (1986): Lab. Proj. ID TMU3144/ B. Unpublished study prepared by ICI Americas Inc. 45 p.

40693102 French, D.; Brown, P.; Leahey, J. ( 1987) Fluazifop-P-Butyl: Quantification and Characterization of Radioactive Residues in Celery: Proj. ID RJ0590B. Unpublished study prepared by Imperial Chemi- cal Industr ies, Jealott's Hill Research Station. 75 p.

40693103 Trumbo, R.; Francis, P. (1986) Fluazifop- P-Butyl: Residues of Fluazifop on Celery: Proj. ID TMU3077/B. Unpublished study pr epared by ICI Americas Inc. 15 p.

40693104 Watford, S.; Francis, P. (1988) Fluazifop-P-Butyl: Fluazifop and Reference X Residues in Celery (1986): Proj. ID TMU3418/B. Un- published study prepared by ICI Americas Inc. 86 p.

40693105 Plyler, S.; Francis, P. (1986) Fluazifop-Bu tyl: Residues of Fluazifop on Lettuce: Proj. ID TMU3005/B. Unpublished study prepared by ICI Americas Inc. 19 p.

40693106 Watford, S.; Francis, P. (1988) Fluazifop-P-Butyl: Fluazifop and Reference X Residues in Lettuce (1986): Proj. ID TMU3418/B. Un published study prepared by ICI Americas Inc. 52 p.

40831301 Kaminski, B. (1988) Residue Chemistry Data Overview and Summary: (Fusilade 2000 4E Herbicide). Unpublished study prepar ed by ICI Americas Inc. 95 p.

40831302 Koubek, K. (1984) Fluazifop Residues in Peanuts: Supplement to Previously Submitted Data, EPA Accession No. 072889, Ref. 11D: Project ID: TMU 1196/B Revised. Unpublished study prepared by ICI Americas Inc. 88 p.

40831306 Francis, P.; Plyler, S. (1986) Fluazifop-p- Butyl: A Comparison of the Level of Residues Found in Peanuts from Trials Conducted in 1984: Project ID: TMU 1978. Unpublished study prepared by ICI Americas Inc. 19 p.

40831308 Hayward, G. (1988) Fluazifop-p-Butyl and Reference X, Residues in Peanuts from Trials in the USA During 1986: Project ID: M 4600B. Unpublished study prepared by ICI Plant Protection Div. 18 p.

40831309 Hayward, G. (1988) Fluazifop-p-Butyl (R eference X): Storage Stability of Residues in Deep Frozen Peanut Kernel Samples: Project ID: M4723B. Unpublished study prepared by ICI Plant Protection Div. 14 p.

41007602 Roper, E.; Francis, P. (1988) Fluazifo p-P-Butyl: Residues of Fluizafop (sic) in Sugarcane Following Spot Applications of Fusilade 2000: Proj. ID TMU 3310/B. Unpublished study prepared by ICI Americas Inc. 32 p.

41108001 Baron, J. (1989) Fluazifop: Magnitude of Residue on Asparagus--MI Study: IR-4 PR No. 3944. Unpublished study prepared by IR-4 Northcentral Analytical Laboratory, Michigan State Univ. 34 p.

41165101 Francis, P. (1989) Fluazifop Residues in Peanuts: Supplement to Previously Submitted Data, EPA MRID No. 40831302. Unpublished study prepared by ICI Americas Inc. 9 p.

41373702 Hayward, G. (1988) Fluazifop-p-buty l and Reference X: Storage Stability of Residues in Deep Frozen Onion Samples: Lab Project ID M4843B. Unpublished study prepared by ICI Agrochemicals. 12 p.

41373703 Hayward, G. (1988) Fluazifop-p-butyl (R eference X): Storage Stability of Residues in Deep Frozen Apples, Lettuce and Soybean Samples: Laboratory Project ID M4842B. Unpublished study pre- pared by ICI Agrochemicals. 17 p.

41373704 Hayward, G. (1988) Fluazifop-p-buty l and Reference X: Storage Stability of Residues in Deep Frozen Peanut Kernel Samples: Lab Project ID: M4841B. Unpublished study prepared by ICI Agrochemicals. 14 p.

### Page 63 of 78 41373705 Francis, P. (1989) Fusilade 2000 (Fluazif op-p-butyl)--Magnitude of the Residue Study on Citrus: Lab Project Number: 005-86-05: RR 89-051B. Unpublished study prepared by ICI Americas, Inc. 135 p.

41373706 Francis, P. (1989) Fusilade 2000 (Fluaz ifop-p-butyl)--Magnitude of the Residue on Processed Orange Products: Lab Project ID: 005-86-07: RR 89-052B. Unpublished study prepared by ICI Americas, Inc. 55 p.

92068022 Atreya, N. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40294002 and Related MRIDs 40140401, 41373702, 41373703, 4083 1309. Fluazifop-P-butyl: Storage Stability of Residues in Deep Frozen Crop Samples: Report Nos. M4429B, M4843B, M4723B, M4841B and M4842B. Prepared by ICI Agri cultural Experiment Station. 9 p.

92068023 Baron, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40355101. Fluazifop: Magnitude of the Residue in or on Asparagus: Project No. 2201; Pesticide Petition 7E3565. Prepared by Interregional Research Project No. 4. 8 p.

92068024 Atreya, N. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00152494. FluazifopP-butyl: Residues in Carrots and Sugarbeet from Trials Carried out in the USA During 1983 and 1984: Report No. M44041B: Study No. PP005B026. Prepared by ICI Agrochemicals. 9 p.

92068025 Baron, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40725701. Fluazifop - Magnitude of the Residue on Coffee: Projec t No. 3432: Pesticide Petition 8E 3661. Prepared by University of HawaiI. 11 p.

92068026 Riggle, B. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00162447 and Related MRIDs 00093841, 00116676, 00131452, 0016 2447. FUSILADE Magnitude of the Residue in or on Cotton Seed: ID No. RR-90-075B. Prepared by ICI Americas, Inc. 10

p.

92068027 Baron, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40341601 and Related MRIDs 41148301. Fluazifop: Magnitude of t he Residue on Endive: Project No. 3462. Prepared by USDA-ARS Southeast Watershed Res. Lab. 10 p.

92068028 Riggle, B. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00151494 and Related MRIDs 00161922. FUSILADE Magnitude of the Residue in or on Bulb Onions: Project No. RR-90-052B. Prepared by ICI Americas Inc. 10 p.

92068029 Atreya, N. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40294003 and Related MRIDs 00162047. Residues in Onions from Trials Carried Out in the USA During 1984: Report Nos. M4266B and M4545B; Study Nos PP005B072 and PP005B121. Prepared by ICI Agricultural Experiment Station. 9 p.

92068030 Riggle, D. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40361111. FUSILADE Magnitude of the Residue in or on Pecans: Laboratory ID No. RR/90/057B. Prepared by ICI Americas, Inc. 8 p.

92068031 Baron, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00157191 and Related MRIDs 00157192, 00157193. Fluazifop - Magnitude of the Residue on Tabasco Pepper: IR-4; Project No. 2947 and Petiti on 6E 3384. Prepared by INTERREGIONAL RESEARCH PROJECT NO. 4. 8 p.

92068032 Baron, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40241901. Fluazifop: Magnitude of the Residue on Rhubarb: Project No. 2073. Prepared by N.Y. State AgrI. Experiment Station. 8 p.

92068033 Riggle, B. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00162447 and Related MRIDs 00093840, 00116676, 00131452, 0016 2447. FUSILADE Magnitude of the Residue in or on Soybeans: Laboratory St udy ID RR 90-051B. Prepared by ICI Americas, Inc. 11 p.

### Page 64 of 78 92068034 Riggle, B. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40704805 and Related MRIDs 40361110. FUSILADE Magnitude of t he Residue in or on Plums and Prunes: Laboratory ID No. RR 90-058B. Prepared by ICI Americas, Inc. 9 p.

92068035 Riggle, B. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00137763. FUSILADE Magnitude of the Residue on Carrots: Labor atory ID No. RR-90-030B. Prepared by ICI Americas, Inc. 11 p.

92068036 Baron, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 00144014 and Related MRIDs 00164500. Fluazifop: Magnitude of t he Residue on Sweet Potato: Study ID No.

2328 and Pesticide Petition 4E3100. Prepared by INTERRE GIONAL RESEARCH PROJECT NO. 4. 9 p.

92068037 Baron, J. (1990) ICI Americas Inc. Phase 3 Summary of MRID 41018001. Fluazifop: Magnitude of the Residue in or on Macadamia Nut: Study ID IR-4, Project No. 3431

and Pesticide Petition No. 9E3737. Pr epared by INTERREGIONAL RESEARCH PROJECT NO. 4. 11 p.

92068038 Riggle, B. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40361108 and Related MRIDs 40704803. FUSILADE Magnitude of the Residue in or on Cherries: Laboratory Study ID No. RR 90-060B. Prepared by ICI Americas, Inc. 8 p.

92068039

49193108

49193105 Riggle, B. (1990) ICI Americas Inc. Phase 3 Summary of MRID 40361109 and Related MRIDs 40704804. FUSILADE Magnitude of the Residue in or on Peaches: Laboratory ID No. RR-90-059B. Prepared by ICI Americas, Inc. 8 p.

Huang, S.-B. 2012. Fluazifop-P-Butyl: Fl uazifop-P-Butyl – Residue Method for the Determination of Fluazifop-P-Butyl (R 154875; PP5), Fluazifop-P-Acid (R156172), Compound IV (R150397; CGA181847) and Compound X (R154719; CGA142110) in Water: Analytical Method. Prepar ed by Syngenta Crop Protection, LLC.

Perez, R., J. L. Schmitt. 2013. Fluazifop-P -Butyl: Independent Laboratory Validation of Residue Method (GRM044.04A) for the Determ ination of Fluazifop-P-Butyl (R154875; PP5), Fluazifop-P-Acid (R156172), Compound IV (R150397; CGA181847) and Compound X (R154719; CGA142110) in Water: Final Report. Report prepared by ADPEN Laboratories, Inc.



## 171-4A2 Nature of the Residue in Plants

MRID Citation Reference

92068018 Leahey, J. (1990) ICI Americas Inc. P hase 3 Summary of MRID 40693102. FluazifopP-butyl: Quantitation and Characterization of Radioactive Residues in Celery: Report No. RJ0590B; Study No. PP005AC03. Prepa red by ICI Agrochemicals. 15 p.

92068019 Leahey, J. (1990) ICI Americas Inc. P hase 3 Summary of MRID 40361102. FluazifopP-butyl: Determination of Radioactive Residu es in Grapes From a Vine Treated with 2 Basal Applications of Carbon-14- Fluazi fop-P-butyl: Report No. RJ0569B; Study No. PP005AC02. Prepared by ICI Agrochemicals. 11 p.

### Page 65 of 78 

# APPENDIX B: ECOLOGICAL TOXICITY DATA



# Summary of Toxicity Data for Fluazifop-p-butyl

Plant Data

Green Alga, Static, Metabolite X 72 hr EC50 340 ppm Biomass NOAEC 100 ppm/LOAEC 200 ppm 49224403, 1994

IN REVIEW



### Terrestrial Invertebrate Data

Honeybee (Apis mellifera), Adult, O, / Fluazifop-butyl, Tech% ai 24 hr LD50 153.70686 ug/Bee ae (180 ug/Bee ai) slope = NA 00093809, 1979 /Acceptable

Honey bee (Apis mellifera), Adult, O, / Fluazifop-butyl formulation, 25EC% ai 24 hr LD50 166.515765 ug/Bee ae (195 ug/Bee ai) slope = NA 00093809, 1979 /Acceptable

Honey bee (Apis mellifera), Adult, C, / Fluazifop-butyl, Tech% ai 24 hr LD50 204.94248 ug/Bee ae (240 ug/Bee ai) slope = NA 00093809, 1979 /Acceptable

Honey bee (Apis mellifera), Adult, C, / Fluazifop-butyl formulation, 25 EC% ai 24 hr LD50 81.123065 ug/Bee ae (95 ug/Bee ai) slope = NA 00093809, 1979 /Acceptable

Honey bee (Apis mellifera), Adult, C, / Fluazifop-P-butyl, 13.8% ai 24 hr LD50 53.797401 ug/Bee ae (63 ug/Bee ai) slope = N.R. 00162453, 1984 /Acceptable



### Aquatic Invertebrate Data

Water flea (Daphnia magna), Degredate X

Water flea (Daphnia magna), <24 hr, static, / Fluazifop-buty l, 97.8% ai 48 hr EC50 666 ppm

48 hr EC50 240.1242724 ppm ae (281.2 ppm ai) slope = 5.21 49224401, 1982

IN REVIEW 00087490, 1981 /Acceptable Water flea (Daphnia magna), 12 hr, static, / Fluazifop-butyl (PP009), 94.8% ai 48 hr EC50 8.53927 ppm ae (10 ppm ai) slope = NA 00087488, 1979 /Acceptable

Water flea (Daphnia magna), 12 hr, static, / Fluazifop-butyl (PP009), 25 EC% ai 48 hr EC50 5.5505255 ppm ae (6.5 ppm ai) slope = NA 00087488, 1979 /Acceptable

Water flea (Daphnia magna), 12 hr, static, / Fluazifop-butyl (PP009), 24% ai 48 hr EC50 5.14064054 ppm ae (6.02 ppm ai) slope = NA 00087489, 1980 /Acceptable

Water flea (Daphnia magna), <24 Hr, static, / Fluazifop-p-butyl RS 1:1 racemic, N.R.% ai 48 Hr LC50 472.9901653 ppm ae (553.9 ppm ai) slope = N.R. 00162452, 1983 /Supplemental

Water flea (Daphnia magna), <24 Hr, static, / Fluazifop-p-butyl RS 7:1 enhanced enantiomer,

N.R.% ai 48 Hr LC50 465.9025712 ppm ae (545.6 ppm ai) slope = N.R. 00162452, 1983 /Supplemental

Water flea (Daphnia magna), <24 Hr, static, / Fluazifop-p-butyl RS 14:1 methanol prepartion,

N.R.% ai 48 Hr LC50 352.1594948 ppm ae (412.4 ppm ai) slope = N.R. 00162452, 1983 /Supplemental

Water flea (Daphnia magna), <24 hr, static, / Fluazifop-butyl, RS11% ai 48 hr EC50 472.9901653 ppm ae (553.9 ppm ai) slope = 10.96 00162452, 1983 /Supplemental

Water flea (Daphnia magna), <24 hr, static, / Fluazifop-butyl, RS71% ai 48 hr EC50 465.9025712 ppm ae (545.6 ppm ai) slope = N.R. 00162452, 1983 /Supplemental

Water flea (Daphnia magna), <24 hr, static, / Fluazifop-butyl, RS14% ai 48 hr EC50 352.1594948 ppm ae (412.4 ppm ai) slope = N.R. 00162452, 1983 /Supplemental

Fiddler crab (Uca pugilator), 1.5 G, flow-through, / Fluazifop-butyl (PP009), 25.4% ai 96 hr LC50 3.5011007 ppm ae (4.1 ppm ai) slope = NA 00093806, 1980 /Supplemental

Mysid (Americamysis bahia), 6-8 D, flow-through, / Fluazifop-butyl (PP009), 98.6% ai 96 hr LC50 184.448232 ppb ae (216 ppb ai) slope = 4.6 00093805, 1980 /Acceptable

### Page 66 of 78 Mysid (Americamysis bahia), N.R., flow-through, / Fluazifop-P-butyl, 92.2% ai 96 hr LC50 0.43550277 ppm ae (0.51 ppm ai) slope = N.R. 42543201, 1991 /Acceptable

Pink shrimp (Penaeus duorarum), 0.21 g, flowthrough, / Fluazifop-butyl (PP009), 25.4% ai 96 hr LC50 5.123562 ppm ae (6 ppm ai) slope = NA 00093804, 1980 /Acceptable

Pacific oyster (Crassostr ea gigas), EmbLrv, flowthrough, / Fluazifop-butyl (PP009), 98.6% ai 48 hr LC50 82.830919 ppb ae (97 ppb ai) slope = 5.5 00131460, 1982 /Acceptable

Eastern oyster (Crassostrea virginica), SPAT, flowthrough, / Fluazifop-P-butyl, 90% ai 96 hr EC50 0.40134569 ppm ae (0.47 ppm ai) slope = 1.45 41900601, 1991 /Supplemental

Mysid (Americamysis bahia), 48 hr, flow-through, / Fluazifop-butyl (PP009), 98.6% ai 28 D LC50 66.3501279 ppb ae (77.7 ppb ai) slope = 2.1 00093805, 1981 /Supplemental

Water flea (Daphnia magna), LifeCycle, flowthrough, / Fluazifop-butyl, 97.2% ai 21 D LOEC 213.48175 ppb ae (250 ppb ai) slope = NA 00093807, 1981 /Supplemental



### Fish Data

Bluegill sunfish (Lepomismacrochirus), 4.13 g, flowthrough, / Fluazifop-butyl, 98.6%

ai 96 hr LC50 0.45258131 ppm ae (0.53 ppm ai) slope = NA 00087485, 1981 /Acceptable

Bluegill sunfish (Lepomismacrochirus), 3.31 g, flowthrough, / Fluazifop-butyl, 25.8%

ai

Bluegill sunfish (Lepomis macrochirus), flow-through,

25% Formulation 96 hr LC50 2.27998509 ppm ae (2.67 ppm ai) slope = NA

96 hr LC50 1.6 ppm 00087486, 1981 /Acceptable

40829203, 1985

IN REVIEW

Bluegill sunfish (Lepomis macrochirus), flow-through, 125 g/l Formulation

Fathead minnow (Pimephales promelas), <24 hr, static, / Fluazifop-buty l, 90.2% ai 96 hr LC50 3.3 ppm

96 hr LC50 0.31595299 ppm ae (0.37 ppm ai) slope = 10.6 40829205, 1985

IN REVIEW

00093808, 1981 /Supplemental

Rainbow trout (Oncorhynchus mykiss), 2.2 g, flow-through, / Fluazifop-buty l, 25.8% ai

Rainbow trout (Oncorhynchus mykiss), Static, Metabolite X 96 hr LC50 4.1842423 ppm ae (4.9 ppm ai) slope = 8.9

96 hr LC50 240 ppm 00087484, 1981 /Acceptable

49224402, 1994

IN REVIEW

Rainbow trout (Oncorhynchus mykiss) flow-through, 25%

Formulation

Rainbow trout (Oncorhynchus mykiss) flow-through, 125g/l

Formulation

Rainbow trout (Oncorhynchusmykiss), 6.2 g, static, / Fluazifopbutyl, 98% ai 96 hr LC50 3.4 ppm

96 hr LC50 5.4 ppm

96 hr LC50 99.909459 ppm ae (117 ppm ai) slope = NA 40829202, 1985

IN REVIEW

40829204, 1985

IN REVIEW

00087483, 1981 /Acceptable

### Page 67 of 78 Rainbow trout (Oncorhynchus mykiss), NR, flow-through, / Fluazifop-buty l, 93.7% ai 96 hr LC50 1.20403707 ppm ae (1.41 ppm ai) slope = 15.2 00131458, 1983 /Supplemental

Sheepshead minnow (Cyprinodon variegatus), 0.57 g, flow-through, / Fluazifop-butyl (Fusilade 4E),

46.8EC% ai 96 hr LC50 6.86557308 ppm ae (8.04 ppm ai) slope = 10.1 00152173, 1985 /Acceptable

Sheepshead minnow (Cyprinodon variegatus), 0.37 g, flow-through, / Fluazifop-butyl (25EC formulation), 25.4% ai 96 hr LC50 9.393197 ppm ae (11 ppm ai) slope

= 13.2 ACC070630, 1981 /Acceptable

Fathead minnow (Pimephalespromelas), EarlyLife, flowthrough, / Fluazifop-butyl, 90.2%

ai 30 D LOEC 0.203234626 ppm ae (0.238 ppm ai) slope = NA 00093808, 1981 /Supplemental



### Avian Data

Mallard duck (Anas platyrhynchos), NR, oral, / Fluazifop-buty l, 93.4% ai 14 D LD50 4269.635 ppm ae (<5000 ppm ai) slope =

NA 00131457, 1982 /Acceptable

Mallard duck (Anas platyrhynchos), 15 D, dietary, / Fluazifop-butyl, 99.6% ai 8 D LC50 21348.175 ppm ae (<25000 ppm ai) slope =

NA 00087481, 1980 /Supplemental

Mallard duck (Anas platyrhynchos), 16 WKS, oral, / Fluazifop-P-butyl, 95.8% ai 14 D LD50 3012.654456 mg/kg ae (<3528 mg/kg ai) slope = N.R. 40829201, 1985 /Acceptable

Ring-necked pheasant (Phasianus colchicus), 13 D, dietary, / Fluazifop-butyl (Dieldrin), 99.6%

ai 8 D LD50 ppm ae (20767.77 ppm ai) slope =

NA 00087482, 1982 /Acceptable

Bobwhite quail (Colinus virginianus), 11 D, dietary, / Fluazifop-P-butyl, 89.09% ai 8 D LC50 4466.03821 ppm ae (<5230 ppm ai) slope =

N.A. 40851401, 1985 /Acceptable

Bobwhite quail (Colinus virginianus), 11 D, dietary, / Fluazifop-p-butyl, 95.8% ai 8 D LC50 4466.03821 ppm ae (<5230 ppm ai) slope =

N.A. 40859401, 1985 /Acceptable

Mallard duck (Anas platyrhynchos), 9 D, dietary, / Fluazifop-P-butyl, 95% ai 8 D LC50 4141.54595 ppm ae (<4850 ppm ai) slope =

N.R. 00087481, 1987 /Acceptable

Bobwhite quail (Colinus virginianus), reproductive study, / Fluazifop-butyl, 99.6% ai 31 Wk LOAEL 42.69635 ppm ae (<50 ppm ai) slope

= NA 00093802, 1981 /Supplemental

Mallard duck (Anas platyrhynchos), reproductive study, / Fluazifop-butyl, 99.6% ai 23 Wk LOAEL 42.69635 ppm ae (<50 ppm ai) slope

= NA 00093801, 1981 /Supplemental



### Mammalian Data

Acute Toxicity Data on FLUAZIFOP-BUTYL & FLUAZIFOP-P-BUTYL

.

Acute Studies with Fluazifop-butyl (PC 122805)

Guideline No./ Study Type MRID No. Results Toxicity Category

### Page 68 of 78 

### Acute Toxicity Data on FLUAZIFOP-BUTYL & FLUAZIFOP-P-BUTYL

.

870.1100 Acute oral toxicity/rats (PP009; 97.2%) 00162439 (1983) LD50 = 1940 mg/kg (males) ± 1193- 2758 mg/kg LD50 = 2653 mg/kg (females) ± 1764- 3625 mg/kg III

870.1200 Acute dermal toxicity/rabbits (PP009; 97.2%) 00162439 (1983) LD50 > 2mL/kg (males and females) or approximately 2000 mg/kg III

870.1300 Acute inhalation toxicity/rats (PP009; 97%) 79/ISK034/387 46082901,

same as 41563701

(1979) LC50 > 2.3 mg/L for 43% with a particle size <5 μm LC50 >4.37 mg/L for 83% with a particle size <10 μm III

870.2400 Acute eye

irritation/rabbit (PP009; 93.3%) 79/ILK9/068 00088855 (1979) Non-irritating IV

870.2500 Acute dermal

irritation/rabbit (PP009; 93.3%) 79ILK8/056 00088853 (1979) Mild erythema at 72 hours IV

870.2600 Skin sensitization/GP (PP009; 99 6%) 80/ILK026/349 00088854 (1980) Not a dermal sensitizer

Acute Studies with Fluazifop-P-butyl (PC 122809)

Guideline No./ Study Type MRID No. Results Toxicity Category

870.1100 Acute oral toxicity/rats (PP005; 93.7% & 86.3% ) 00162440 (1984) LD50 = 3680 mg/kg for males rats LD50 = 2451 mg/kg for female rats III

III

870.1200 Acute dermal toxicity/rabbits (PP005; 93.7% & 86.3%) 00162440 (1984) LD50 > 2000 mg/kg or >1.73 mL/kg III

870.1300 Acute inhalation a toxicity/rats (PP005; 24.6%) CTL/P/3331 41917904 (1991) LC50 > 1.7 mg/L III

870.2400 Acute eye

irritation/rabbit (PP005; 86.3%) CTL/P/856 00162441 (1983) Mild irritation, cleared within 3 days IV

870.2500 Acute dermal

irritation/rabbit (PP005; 86.3%) CTL/P/856 00162441 (1983) Slight irritation, cleared within 72

hours IV

870.2600 Skin sensitization/GP (PP005; 99.6%) 80/ILK026/349 00162441 (1983) Not a skin sensitizer

a This study was conducted with a mixture of 24.6% fluazifop-P- butyl and 7.0% fenoxyprop-P-ethyl, however, the concentration fluazifop-P-butyl in the inhalation chamber was determined to be 1.7 mg/L. PPOO9 was used to i ndicate the technical grade of fluazifop-butyl. PPOO5 was used to indicate the technical grade of fluazifop-P-butyl.

### Page 69 of 78 

### Subchronic, Chronic, Developmental, Repro ductive and Other Toxicity Profile on Fluazifop-butyl [FB] and Fluazifop-P-butyl [FPB].

Guideline No./

Study Type MRID No. (year)/

Classification /Doses Results

870.3100 90-Day oral toxicity (rat) with FB 00093820 (1980) Acceptable/guideline 0, 10, 100, 2000 ppm M: 0, 0.7, 7.1, 144.5 mg/kg/day F; 0, 0.8, 8.0, 161.9 mg/kg/day NOAEL=0.7 mg/kg/day LOAEL=7.1 mg/kg/day based on liver and kidney histopathology.

870.3100 90-Day oral toxicity (rat) with FPB 46158402 (1985) Acceptable/guideline 0, 10, 100, 2000 ppm

—F: 0, 0.5, 5, 100 mg/kg/day NOAEL=0.5 mg/kg/day LOAEL=5 mg/kg/day based on decreased spleen weight and decreased hematological parameters in males. Dose related testicular weight decrement and cholesterol depression were

also seen.

870.3150 90-Day oral toxicity (dog) with FB 00093821 (1980) Acceptable/guideline

0, 5, 25, 125/250 mg/kg/day NOAEL = 25 mg/kg/day LOAEL = 125/250 mg/kg/day based on multiple pathologies in 3 dogs (2 males and 1 female) killed at 1 month dosed at 250 mg/kg/day. Also seen were body weight loss gut lesions, severe eye lesions and hepatotoxicity. In remaining surviving dogs dosed at 125 mg/kg/day , mild to equivocal

liver lesions were seen.

870.3150 90-Day oral toxicity (hamster) with FPB 46082902 (2001) Acceptable/guideline Males: 0, 19.5, 78.3 or 291.9 mg/kg/day Females: 0, 19.9, 79.0 or 319.6 mg/kg/day NOAEL = M/F: 78.3/79.0 mg/kg/day LOAEL = M/F: 291.9/319.6 mg/kg/day based on decreased body weight/body weight gain and food efficiency in males and evidence of liver toxicity; centrilobular eosinophilia/loss of glycogen in males and females.

870.3200 21/28-Day dermal toxicity (rabbit) with

FB 00093819 (1980) Acceptable/guideline

0, 100, 500, 2000 mg/kg/day NOAEL = 100 mg/kg/day LOAEL = 500 mg/kg/day based on death in 1 male and at 2000 mg/kg/day, death 4 males and 5 females, possibly due to kidney failure.

870.3250 90-Day dermal toxicity (species) Not required

870.3465 90-Day inhalation toxicity (species) Not required.

870.3700a

Prenatal developmental in (Sprague Dawley

rats) with FB 0008857, 92067047 (1981) Acceptable/guideline 0, 10, 50, 200 mg/kg/day Maternal NOAEL = 200 mg/kg/day

LOAEL = None based on matern al weight decrement due to gravid uterine weight decrement.

Developmental NOAEL=none LOAEL=10 mg/kg/day based on delayed ossification.

### Page 70 of 78 

### Subchronic, Chronic, Developmental, Repro ductive and Other Toxicity Profile on Fluazifop-butyl [FB] and Fluazifop-P-butyl [FPB].

Guideline No./

Study Type MRID No. (year)/

Classification /Doses Results

Malformations NOAEL = 50 mg/kg/day LOAEL = 200 mg/kg/day based on diaphragmatic hernia.

870.3700a Developmental toxicity (Sprague Dawley rat) with FB 00088858, 92067048, 92967020 (1981) Acceptable/guideline

0, 1.0, 5.0, 10, 200 mg/kg/day with FB Maternal NOAEL=200 mg/kg/day. LOAEL=None based on maternal weight decrement partially explained by gravid urine weight decrement. Developmental NOAEL=1 mg/kg/day. LOAEL=5 mg/kg/day based on fetal weight decrement and increased incidence of small fetuses and delayed

ossification. Malformations NOAEL= 10 mg/kg/day LOAEL=200 mg/kg/day based on increased incidence of diaphragmatic hernia.

870.3700a Developmental toxicity (Wistar rats)

with FPB 46158401 (1991) Acceptable/guideline

0, 0.5, 1.0, 20, 300 mg/kg/day Maternal NOAEL=20 mg/kg/day LOAEL=300 mg/kg/day based on body weight gain

decrement. Developmental NOAEL=1.0 mg/kg/day LOAEL=20 mg/kg/day based on delayed ossification in skull bones, cervical arches and centrum in fetuses and

litters and delayed ossification in the manus and pes.

870.3700a Developmental Toxicity (Wistar rats)

with FPB 46082903 (1989) Acceptable/guideline 0, 2, 5 or 100 mg/kg/day Maternal NOAEL=100 mg/kg/day LOAEL= None based no maternal toxicity.

Developmental NOAEL=2.0 mg/kg/day LOAEL=5.0 mg/kg/day based on based on dose related delayed ossification in skull bones [occipital and parietal] in

fetuses and litters.

870.3700a Developmental Toxicity (Wistar rats)

with FPB 46082013 (1990) Acceptable/guideline 0, 2.0, 5.0, 100

mg/kg/day Maternal NOAEL=100 mg/kg/day

LOAEL= None based on no toxic effects Developmental NOAEL=2.0 mg/kg/day LOAEL=5.0 mg/kg/day based on delayed ossification in skull bones, sternebrae bipartite, sternebrae and calcenum

unossifided in fetuses and litters.

The overall conclusions based on a weight of evidence on the five studies of developmental toxicity in the rat were a NOAEL/LOAEL = 2.0/5.0 mg/kg/day based on fetal weight decrement and delayed ossification.

870.3700b Developmental toxicity (NZW rabbit) with FB 00088856, 92067049, 92067021 (1981) Acceptable/guideline 0, 10, 30, 90 mg/kg/day Maternal NOAEL=30 mg/kg/day LOAEL=90 mg/kg/day based on abortions.

Developmental NOAEL=30 mg/kg/day LOAEL=90 mg/kg/day based on nominal increases in delayed ossification, total litter loss, abortions, small fetuses,

cloudy eyes all above mean or range of historical controls

870.3700b Developmental toxicity (NZW rabbits) with FPB 46082904 (1993) Acceptable/guideline 0, 2, 10, 50 mg/kg/day Maternal NOAEL=10 mg/kg/day LOAEL=50 mg/kg/day based death, abortions and body weight loss Developmental NOAEL=10 mg/kg/day LOAEL=50 mg/kg/day based on increased incidence of 13 th rib and delayed ossification in sternebrae 2.

### Page 71 of 78 

### Subchronic, Chronic, Developmental, Repro ductive and Other Toxicity Profile on Fluazifop-butyl [FB] and Fluazifop-P-butyl [FPB].

Guideline No./

Study Type MRID No. (year)/

Classification /Doses Results

870.3800 Reproduction and

fertility effects (rats) with FB 00088859, 92067050 (1981) Acceptable/guideline 0, 10, 80, 250 ppm M/F: 0/0, 0.74/0.88,

5.8/7.1, 21.7/17.5 mg/kg/day Parental/Systemic NOAEL = M/F 0.74/7.1 mg/kg/day LOAEL = M/F 5.8/ 21.7 mg/kg/day based on decreased spleen wt. in males & increased absolute & relative liver & kidney wts. & geriatric nephropathy in females. Offspring NOAEL = 7.1 mg/kg/day LOAEL = 21.7 mg/kg/day based on pup viability in f1 and f2 pups during lactational day 1, 4, 11, 18 & 25 and decreased f2 pup weight on lactational day 25. Reproductive NOAEL = M/F 0.74/0.88mg/kg/day LOAEL = M/F 5.8/7.1 mg/kg/day based on decreased abs. &

rel testes & epididymal weight and in females decreased pituitary & uterine weights. Sperm counts not available.

Conclusions on the 2-generation study on reproduction in the Sprague Dawley rat: The cause of the dose related testes wt decrease in the P0 and F1 generations has not been demonstrated, but no sperm counts, morphology, motility have been conducted to date. Extensive short te rm studies on testes weight, testes histopathology, and endocrine effects (MRID# 46082911, 46082916, 46082917,46082920 & 46082920, see table 4.1d) failed to find the reason for the testes weight decrement in the rat an d hamster. However, since the most sensitive tests for effects on sperm were not conducted (s perm count, motility and morphology as indicated in the 19 96 guidelines), it is concluded that testes weight decrement from possible decrements in sperm seen in the rat reproduction and the chronic study in hamsters have not been adequately eliminated. The histology on the testes does not support an effect, but histology is insufficiently se nsitive to detect an slight effect.

870.4100a Chronic toxicity (rats) 870.4300 satisfies the requirement

870.4100b Chronic toxicity

(dog) with FB 00131462, 00131463, 92067018 (1982) Acceptable/guideline 0, 5, 25, 125 mg/kg/day NOAEL = 5 mg/kg/day LOAEL = 25 mg/kg/day based on marginally increased incidence adrenal fatty vacuolation & increased incidence of thymic involution and at 125 mg/kg/day death of 4/6 males and 2/6 females, eye, gastrointestinal tract lesions, adrenal and bone marrow pathology & thymic involution.

870.4200 Carcinogenicity (hamster) with FPB 4534501, 46082905 (2001) Acceptable/guideline 0, 0, 200, 750, 3000 ppm M: 0, 0, 12.5, 47.4, 193.6 mg/kg/day F: 0, 0, 12.1, 45.5, 181.4 mg/kg/day NOAEL =M/F 12.5/12.1 mg/kg/day LOAEL = 47.5/45.5 mg/kg/day based on based on increased incidence of males with reduced sperm, testicular degeneration, eye cataract changes, liver inflamation and gall stones and in females, in creased incidence of ovarian stroma cell/sex chord hyperplasia.

No evidence of carcinogenicity

870.4300 Chronic/Carcinogeni city (rat) with FB 41563703 (1985) Acceptable/guideline 0, 2, 10, 80, 250 ppm M: 0, 0.10, 0.51, 4.15, 12.3 mg/kg/day F: 0, 0.13, 0.65, 5.2, 16.0 mg/kg/day NOAEL =M/F 0.51/5.2 mg/kg/day LOAEL =M/F 4.15/16.0 mg/kg/day based on increased mortality & nephropathy exacerbated by respiratory stress, and in females possible increased basal and/or follicular/luteal cysts. No evidence of carcinogenicity

### Page 72 of 78 

### Subchronic, Chronic, Developmental, Repro ductive and Other Toxicity Profile on Fluazifop-butyl [FB] and Fluazifop-P-butyl [FPB].

Guideline No./

Study Type MRID No. (year)/

Classification /Doses Results

870.6100a Acute neurotoxicity in hens

with FB 00093818 (1981) Acceptable/guideline 0, 3750, 7500 or 15000 or 15000 mg/kg Fluazifop-butyl exposed hens showed no evidence of delayed neurotoxicity.

870.6200a Acute neurotoxicity

screening battery Not required

870.6200b

Subchronic neurotoxicity screening battery Not required

870.6300 Developmental neurotoxicity Not required

870.7485

Metabolism and pharmacokinetics

(rats) with FB 00093822 through 00093828 (1981) Acceptable/guideline

1 mg/kg and 1000 mg/kg Fluazifop-butyl is rapidly hydrolyzed to fluazifop acid by blood enzymes and excreted as the acid and its conjugates in

the urine of males and females. Due to biliary excretion parent compound, fluazifop acid and its conjugates are

excreted in the feces of male s at much higher proportions than in feces of the female. Excretion was complete in 7 days, with the exception of small amounts in the fat in some

rats.

870.7600 Dermal penetration (human) MRID# 46082918 a human study/NG satisfies guideline

870.7600.

NG Comparative

metabolism with FB

and FPB in rats 00162445, 0012446 (1983) Acceptable/NG 1 mg/kg FB is hydrolyzed and the [S] enantiomer is converted to the [R] enantiomer. Whether fluazifop-butyl [RS] (50:50) or fluazifop-P-butyl [S] (90:10) is administered, within a hour the blood contained a mixture composed of fluazifop acid in

a ratio of [R] 95% and [S] 3%. The two products behaved similarly and reached the same equilibrium within experimental error.

NG Plasma level

time course with FB

and FPB in rats 46082910 (1998) Acceptable/NG

200 mg/kg The time course of plasma levels and elimination of the acid metabolite were similar for both fluazifop-butyl and fluazifop-P-butyl. Plasma levels of the acid from both isomers were much higher in males than in females. The data support previous studies.

NG Absorption and

excretion study in

hamsters with FPB 46082923 (2002) Acceptable/NG 0, 200, 750, 3000 ppm The study was conducted in two phases, Phase 1- single dose followed by 3 days of unlabeled test material and Phase

2 - 24 hour feeding of labeled test material followed by 3 day of unlabeled test material. Data were consistent with excretion data from other spec ies. The system appeared saturated, since the ratio of the 3000/200 ppm dose levels

### Page 73 of 78 

### Subchronic, Chronic, Developmental, Repro ductive and Other Toxicity Profile on Fluazifop-butyl [FB] and Fluazifop-P-butyl [FPB].

Guideline No./

Study Type MRID No. (year)/

Classification /Doses Results

was much lower than the ratio of respective plasma levels, especially for males.

NG Absorption,

excretion and tissue

retention in mice

with FB 46082925 (1992) Acceptable/NG 1 and 150 mg/kg Male mice excreted proportionally more in feces and less in urine than females. Although males excreted more than

females in the feces and females excreted more than males in the urine, the difference be tween males and female mice

was smaller than with male and female rats. The study showed individual variability in excretion, similar to that

found in the rats, dog and human, although analytical

deviation may have explained part of the variation.

NG Absorption and

excretion in dogs

with FB 0093829 (1981) Acceptable/NG 1 mg/kg One dog showed delayed absorption. Excretion rate similar to females rats. No evidence of biliary excretion.

NG Peroxasome proliferation in mice,

rats, hamsters and

humans with FPB 46082919 (1988) Acceptable/NG 0, 80, 250, 1000 or 2000

ppm In vivo and in vitro peroxasome proliferation was studied in the mouse, rat and hamster and in vitro human hepatocytes. Proliferation in hepatocytes from the greatest to the smallest

was: mice > rats > hamster >> human. No increase in cell replication was seen at any dose.

NG Androgen/estrogen activity with FPB &

acid; FB & acid

metabolite 46082916 (2001) Acceptable/NG No agonist or antagonist activity was detected for FPB or FB or their acid metabolites. Using recombinant yeast strains expressing human androgen r eceptor or estrogen receptor,the intrinsic androgenic, anti-androgenic, estrogenic, antiestrogenic activity of FPB, FB and their respective acid

metabolites have been assessed by absorbance in a

transcription assay. Positive antagonists were hydrotamoxifen and flutamide, which induced appropriate antagonic activity. Agonistic activity assessed by comparison to 17 β -estradiol and dihydrotestosterone; antagonic activity was assessed by inhibition of 17 β estradiol

and dihydrotestosterone activity . No agonist or antagonic

activity was found within 7 orders of magnitude (oom) greater than the conc. of estradiol transcription, 4 oom greater for inhibition of estradiol transcription and 6 oom for

agonistic activity of dihydrotestosterone and up to 156 μ M antagonist activity by a dose related decrease in dihydrotestosterone-medi ated androgenic activity.

NG Dermal absorption in humans

with FB 46082918, 46082927, 4153704 (1991) Acceptable/NG 2 mg & 200 mg/person Dermal absorption was 8.6% at 2 mg/person and 1.9% at 200 mg/person

NG Dermal

multidose in humans

with FB 46082908 (1989) Acceptable/NG 20 mg Six male humans were dermally dosed for 5 days at 20 mg/person and the pharmacokinetics followed The study

was consistent with other studies in humans, dogs and female rats. Estimated one-half-life was 12.6 to 17.3 hours,

which was much more uniform than seen in other studies.

There was no evidence of accumulation of the dose.

### Page 74 of 78 

### Subchronic, Chronic, Developmental, Repro ductive and Other Toxicity Profile on Fluazifop-butyl [FB] and Fluazifop-P-butyl [FPB].

Guideline No./

Study Type MRID No. (year)/

Classification /Doses Results

NG Oral absorption,

metabolism and

excretion in men

with FB 00131464 (1983) Acceptable/NG

0.07mg/kg Metabolism was similar to the female rat and dog. Absorption was delayed in one man and excretion in the urine was variable with no evidence of biliary excretion.

### Page 75 of 78 

# APPENDIX C: Example of SIP INPUT and OUTPUT

Drinking Water Exposure Drinking water for the purposes of terrestrial organism risk assessment is defined as that portion of an organism’s daily water intake that is no t met by dietary or metabol ic sources and must be consumed in liquid form. Typical drinking water sources for wildlife in pesticide use areas may include on-field puddles, irriga tion equipment (e.g., drip irrigati on in grape cultivation), dew deposited on treated plants, and o ff-field surface water exposures.

The Screening Imbibition Program (SIP v.1.0, Released June 15, 2010) was used to calculate an upper bound estimate of exposure using fluazif op’s solubility in water (1 mg/L at 25 o 

### C). Using TGAI data for the most sensitive acute (fluazifop-P-butyl LD 50 

### 3528 mg a.i./kg-bw for the Mallard duck, MRID 40829201) and chronic (flu azifop-butyl NOAEC <50 mg a.i./kg-diet, Mallard duck, MRID 00093801) avian toxicity endpoint s and the most sensitive acute fluazifopbutyl (LD 50 

### = 1940 mg a.i./kg-bw, male rat, MR ID 00162439) and chronic (fluazifop-butyl reproduction NOAEC = 80 mg a.i./kg-diet, MR ID 00088859) mammalian toxicity endpoints. Drinking water exposure alone was determined not to be a potential pa thway of concern for avian and mammalian species on an acute and chronic basis. Deta iled information about the SIP v.1.0, as well as the tool, can be found on the EPA’s website at http://www.epa.gov/pesticides/science/models_pg.htm#terrestrial

.

Table 1. Inputs

Parameter Value

Chemical name Fluazifop

Solubility (in water at 25 o C; mg/L) 1

Mammalian LD 50 (mg/kg-bw) 1940
Mammalian test species laboratory rat Body weight (g) of "other" mammalian species

Mammalian NOAEL (mg/kg-bw) 4
Mammalian test species laboratory rat Body weight (g) of "other" mammalian species

Avian LD 50 (mg/kg-bw) 3528
Avian test species Duck Mineau scaling factor 1.15

Mallard NOAEC (mg/kg-diet) <50 Bobwhite quail NOAEC (mg/kg-diet) <50

Table 2. Mammalian Results

Parameter Acute Chronic Upper bound exposure (mg/kg-bw) 0.1720 0.1720 Adjusted toxicity value (mg/kg-bw) 1492.1715 3.0766

### Page 76 of 78 Ratio of exposure to toxicity 0.0001 0.0559

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) 0.8100 0.81 Adjusted toxicity value (mg/kg-bw) 1831.80 2.4806 Ratio of exposure to acute toxicity 0.0004 0.3265

Conclusion* Drinking water exposure alone is NOT a potential concern for birds Drinking

water

exposure alone is

NOT a potential

concern for birds

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

### Page 77 of 78 

# APPENDIX D: STIR inputs and outputs

Inhalation Exposure The Screening Tool for Inhalation Risk (STI R v.1.0, November 19, 2010) was used to calculate an upper bound estimate of exposure using fluazi fop-butyl’s vapor pre ssure (0.055 mm Hg at

20 o 

### C) and molecular weight (383.37 g/mol) for vapor phase exposure as well as the maximum application rate (1.125 lbs a.i./A, which is th e maximum seasonal applic ation rate (to pecans, grapes, citrus) and method of appli cation (aerial spray) for spray drif t. STIR incorporates results from several toxicity studies in cluding acute oral and inhalati on rat toxicity endpoints obtained from the “six-pack” of core studies, which are a series of six guideline studies that are submitted to the Registration Division of the Office of Pesticide Programs on laboratory rats for technical and formulated products of a pesticide (rat acute oral (TGAI): LD 50 

### = 1940 mg a.i./kg-bw; rat inhalation (TGAI): LC 50 

### >2.3 mg/L (MRID 46082901). In addition, the most sensitive acute oral avian toxicity endpoint (Mallard duck, LD 50 

### = 4269 mg a.i./kg-bw (MRID 00131457) was used.

Based on the results of the STIR model, inhalation exposure alone was not determined to be a potential pathway of concern for avian or mammalia n species on an acute basi s as a result of spray applications of fluazifop-butyl.

Inhalation exposure via spra y drift and/or vapor-phase of the pesticide alone does not appear to be of concern. The analysis of the inhalation route in STIR does not consider that aggregation with other exposure pathways such as dietary, dermal , or drinking water may contribute to a total exposure that has a potential for e ffects to non-target animals. Ho wever, the Agency does consider the relative importance of other r outes of exposure in situations wh ere data indicate that pesticide exposures through other rout es may be potentially signi ficant contributors to wildlife risk (USEPA, 2004). Detailed information about STIR v.1.0, as well as the tool, can be found on the EPA’s

website at: http://www.epa.gov/pesticides/science/models_pg.htm#terrestrial

.



# Input

Application and Chem ical Information

Enter Chemical Name Fluazifop butyl

Enter Chemical Use pecans, grapes 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) 383.37 Enter Chemical Vapor Pressure (mmHg) 5.50E-02 Enter Application Rate (lb a.i./acre) 1.125

Toxicity Properties

Bird

Enter Lowest Bird Oral LD 50 (mg/kg bw) 4269 Enter Mineau Scaling Factor 1.15 Enter Tested Bird Weight (kg) 1.58

Mammal

Enter Lowest Rat Oral LD 50 (mg/kg bw) 1940

### Page 78 of 78 Enter Lowest Rat Inhalation LC 50 (mg/L) 2.3 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 ) 1.13E+03 Maximum 1-hour Vapor Inhalation Dose (mg/kg) 1.43E+02

Adjusted Inhalation LD 50 2.03E+01

Ratio of Vapor Dose to Adjusted Inhalation LD 50 7.01E+00 Maximum Post-treatment Spray Inhalation Dose (mg/kg) 1.08E-01 Ratio of Droplet Inhalation Dose to Adjusted Inhalation

LD 50 5.31E-03



### Results Mammalian (0.015 kg )
Maximum Vapor Concentration in Air at Saturation (mg/m 3 ) 1.13E+03 Maximum 1-hour Vapor Inhalation Dose (mg/kg) 1.79E+02

Adjusted Inhalation LD 50 1.37E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 1.31E+00 Maximum Post-treatment Spray Inhalation Dose (mg/kg) 1.36E-01 Ratio of Droplet Inhalation Dose to Adjusted Inhalation

LD 50 9.92E-04