### UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON D.C., 20460

OFFICE OF CHEMICAL SAFETY

AND POLLUTION PREVENTION



### PC Code: 000586

DP Barcode: 402259

November 12, 2012



### MEMORANDUM

Subject:



### To:

Through:

From: Registration Review: Preliminary Problem Formulation for Bifenazate

Garland Waleko, Chemical Review Manager

Kevin Costello, Chief

Risk Management and Implementation Branch II

Pesticide Re-evaluation Division (7508P)

Dana Spatz, Branch

# Chie~.**oc:::::~~ ~**  Rosanna Louie-Juzwiak

, RAPL

## ~ ..,.__,.,.,_........_ Environmental Risk Branch III

Environmental Fate and Effects Division (7507P)

Katherine Stebbins,

# Biologis**~o~~P** ,-;... 

# M I\

# lt~\**1~** James Hetrick, Ph.D., Senior

## cl';**ist ~..-1-r.fn** **,A:t_.** 11 ( 

# 11/1 Z..,


### Environmental Risk Branch III

Environmental Fate and Effects Division (7507P)

The Environmental Fate and Effects Division (EFED) has completed the problem formulation in

support of the Registration Review of the insecticide, bifenazate (PC Code 000586) (attached).

This document is intended to provide an overview of what is currently known regarding the

environmental fate and ecological effects associated with bifenazate and its transformation products. Uncertainties regarding attributes of the parent compound and its transformation

. products are also outlined. It 

### describes the preliminary ecological risk hypothesis and the

processes that will be used during the completion of ecological risk assessment in support of registration review

.

Page 1 of32

### Page 2 of 32 

### 1. Introduction

Bifenazate is a selective miticide/insecticide in the carbazate class , which controls the motile stage of mites either by direct contact or through contact with foliar residues. The mode of action

of b ifenazate is to block or close the GABA (gamma aminobu ty ric acid)

- activated chloride channels of susceptible pests, resulting in over excitation of the peripheral nervous system. The

structure of bifenazate can be found in Appendix E and the chemical names and other identifiers

can be found in the chemical i dentity table (Table 3)

. Bifenazate is currently registered for use on a variety of agricultural and non- agricultural use sites.

Agricultural Use Sites

Bi fenazate may be applied to the following bearing or non-bearing crops: avocados, caneberries, cotton, cucurbits, dry beans (except soybean) subgroup, fruiting vegetables, small vine climbing subgroup (except kiwi), hops, legume vegetables (succulent- peas and beans including shelled soybean), mint, okra, pome fruits, tuberous and corm vegetables, low growing berries, stone fruit, tree nuts, and tropical fruit. Additionally, bifenazate may be applied to the following nonbearing crops (not to bear fruit within 1 year of application): berries (blueberry, highbush, elderberry, an d huckleberry), citrus, currants, dates, figs, and persimmons.

Non

- Agricultural Use Sites Bifenazate may be applied to o rnamentals (including bedding plants, flowering plants, foliage plants, bulb crops, perennials, trees and shrubs) in greenhouses/shadehouses, nurseries,

C hristmas tree/conifer plantations, residential areas

, as well as commercial/industrial/institutional areas including golf courses, parks, athletic fields, rights-of- way and other easeme nts.

Bifenazate is registered for 10 active Section 3 registrations, 6 SLN/Section 24c (ID, NV, OR, UT, WA, WY ) and one section 18 for Nevada (timothy hay). Formulation types include wettable powd er, soluble concentrate, flowable concentrate, and water d ispersible granules. Applications may be made via aerial, ground (compressed air, hydraulic ground boom, air blast sprayers, and hand-held/hose end sprayers), and chemigation equipment.

For agricultural crops, the maximum single application rates range from 0.38-0.75 pound of active ingredient per acre (lb a.i./A), with 1-2 applications allowed, depending on the crop. The highest annual rates are for legume vegetables (subgroup 6A and B), dried shelled beans (except soybeans), and root and tuber vegetabl es , for which applications of 0.75 lb a.i./A may be applied twice per crop cycle . T he upcoming assessment will factor in the number of crop cycles per year for the individual crops. The use rates for non- agricultural applications to ornamentals range

from one application at 0.38 applied twice per year to one application of 0.5 lb a.i./A per year. One label for home and garden uses (EPA Reg. No. 400-517), lists only the concentration of the spray (1⁄2 tsp of product per gallon) with directions to apply as a f ull coverage spray to the foliage and as often as every 30 days. Assuming a finishing spray volume of 400 gallons/A (which is

what is recommended for use on ornamentals on the Floramite labels 400-508 and 400-509), the

rate for the uses on 400-517 is antic ipated to be equivalent to 0.5 lb a.i./A to be applied every 30 days (6 lb a.i./A per year). The BEAD LUIS reports (U.S.EPA, 2012) list the use patterns and

maxim um use rates for the current uses of bifenazate. Usage Information ( from BEAD Chemical Profile for Registration Review: Bifenazate, 2012)

### Page 3 of 32 

### Agricultural Use As reported in private market research surveys, overall bifenazate use in agriculture has steadily

increased from 2002 to 2010. On average, approximately 110,000 pounds of b ifenazate is applied annually to 230 ,000 acres at an average rate of 0.50 lbs a.i./acre. The crops with the highest use (in terms of total pounds a.i. applied) are strawberries, raisi n grapes, alm onds, potatoes, wine grapes, and table grapes.

Non

- Agricul tural Use According to USDA NASS surveys of pesticide use in nursery and floriculture (2000, 2003, 2006, and 2009 ), bifenazate usage averaged 3,450 pounds applied annually at an overall application rate of 0.151 lb a.i./acre. These estimates of usage do no t include homeowner uses.

2. Conclusions from Previous Risk Assessments

2.1. Ecological Risk Assessments

EPA has conducted multiple ecological risk assessments in recent years for bifenazate and the degradate D -1989 and these assessments will serve as a basis for this problem formulation document, as well as for the risk assessment to be conducted in registration review. In 2007 (09/07), a new use assessment was conducted for use on tropical fruits, caneberries, and edible podded legume vegetables and succulent shelled soybeans. In 2009 (02/09), t here were two assessments conducted. One assessment was to add new uses (grasses, dry beans, field and sweet corn) and also assess a rate increase for the edible podded legumes and succulent soybeans. The second 2009 (10/09) assessment was to assess increases in rate and the number of allowable annual applications. An assessment was conducted in 2010 (04/10) for uses on avocado, tropical fruit, low growing berries, and small tree climbing fruit. The latest assessment was completed in December 2011 for the proposed new uses on Herb 19A (except chive and chervil), f ruiting vegetables (Group 8-10)

, p ome f ruit (Group 11-10 ), and Timothy Grass f orage and h ay

.

Based on the most recent assessments conducted in 2009 and 2010, the re are risk

concerns for birds (and as surrogate, terrestrial-phase amphibians and reptiles) on an acute and chronic exposure basis (acute RQ =0.48; chronic RQ = 16) and also for endangered estuarine/marine invertebrates on an acute exposure basis (acute RQ =0.16).

L evels of concern were not exceeded for mammals (see note in section 4.2), fish, freshwater invertebrates, and terrestrial/aquatic plants. Table 1 provides a summary of

t he major ecological conclusions presented in the previous risk assessments.

Table 1 . Summary of Risk Concerns Identified for Bifenazate in Previous Assessments

Exposure

Basis Birds Mammals Terrestrial

Plants Terrestrial

Inverts

. (honey bee

hazard) Fish Aquatic

Inverts Aquatic

Plants Groundwater

Contamination Persistence Degradates

of Concern

Acute √

-- -- √

-- √

--

-- -- D- 1989

Chronic √

-- -- -- *

-- --

* Uncertain due to data gaps

### Page 4 of 32 

### 2.2. Drinking Water Exposure Assessments

There have been numerous drinking water assessments to s upport bifenazate uses. Table 2 provides a summary of the surface water modeling for drinking water assessments for bifenazate. Because the Health Effects Division (HED) deemed the bifen azate degradation product 1,1'- biphenyl, 4-methoxy (D1989) as a degradate of concern, it has been considered in the drinking water exposure modeling using a total toxic residue approach (D276801 

### , T. Bloem, 16- Aug

2001). Based on the use for succulent peas and beans, t he highest EDWC for bifenazate and its degradation product D1989 is not expected to exceed 37.3 μg/L for the daily peak concentration and 11.2 μg/L for the annual average concentration. A new drinking water assessment may be required if a new dietary analysis is necessary after review of additional toxicity data . In order to refine the drinking water assessment for bifenazate, additional data on aerobic soil metabolism and aerobic aquatic metabolism would be expected to address uncertainties in the exposure

assessment.

Table 2: Summary of Previous Drinking Water Assessments for Bifenazate and Degradation Product

D1989.

Crop Residues Model Application

Rate Peak Annual Average Date Comment (lb

a

. i

. /A/year) μg/L

Cotton Parent FIRST

0.75 3.69 0.025 9/17/01 PCA=0.20 Hops 16.40 0.114 PCA=0.86 Hops D1989 FIRST 17.8 4.96 11/23/01

PCA=0.87 Cotton 4.08 1.14

Potatoes Parent

+D1989 FIRST 19.1 5.71 10/9/03

PCA=0.86 Strawberries 1.0 22.8 6.38 Hops 0.75 17.8 4.96
Pea, Tuberous, Corm Vegetables Referred to previous assessment on 10/9/03 Grasses, Dry

Parent

+D1989 FIRST 0.75 19.1 5.7 9/30/08 PCA=.87
Beans, Edible podded legumes,

succulent

- shelled peas, beans, soybeans, FIRST

1.50 37.3 11.2 PCA=.87

Field/sweet corn FIRST 0.75 10.1 3.0 PCA=.87

Cane berries

Parent

+D1989

PRZM/EXAMS 1.50 8.1 1.8 8/3/09

PCA=.87 Tropical Fruit 16.7 2.0

Potatoes 10.9 2.5

Tree Fruit 8.4 0.8

Avocado

Parent

+D1989 0.90 8.6 2.7 1/28/10 Tropical Fruit 16.7 2.0 Low Growing Berry 21.3 4.1

Small vine climbing fruit 0.45 10.3 3.0 Herb Subgroup

19A Fruiting Vegetable Group

8

- 10 Parent

+D1989 PRZM/EXAMS

0.5 

### 9. 9 1. 8 10/17/11 PCA=. 87

### Page 5 of 32 Crop Residues Model Application

Rate Peak Annual Average Date Comment

Pome Fruit Group 10

- 11 

### 9.3 2.4
Timothy Grass 0.747 

### 9. 9 1. 8



### 2.3. Clean Water Act Programs

B ifenazate 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 . In addition, no Total Maximum Daily Loads (TMDL) have been developed for bifenazate based on information provided at http://iaspub.epa.gov/tmdl_waters10/attains_nation.tmdl_pollutant_detail?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 extent possible, data should conform to the quality standards in Appendix A of the OPP Standard Operating Procedure: Inclusion of Impaired Water Body and Other Water Quality Data in OPP’s Registration Review Risk Assessment and Management Process (see: http://www.epa.gov/oppfead1/cb/ppdc/2006/november06/session1-sop.pdf), in order to ensure they can be used quantitatively or qualitatively in pesticide risk assessments.

Surface Water

Th ere are no water monitoring data for bifenazate or D1989 in the USGS National Water

- Quality Assessment Program ( NAWQA), USEPA/USGS Pilot Reservoir Monitoring Program, USDA Pesticide Data Program (PDP), and California Department of Pesticide Regulation (CDPR)

.

3. Environmental Fate and Transport

Chemical identification and physical chemical properties of (2

- (4 -methoxy-[1,1’-biphenyl]-3- yl )

- methylethyl ester (bifenazate) and its degradation product 1,1'- biphenyl, 4

- methoxy (D1989) are provided in Table 3

.

### Page 6 of 32 Table 3 . Chemical Identification Information for Bifenazate and Its Degradation Product D1989

Physical and Chemical Properties

Properties Bifenazate D1989

Chemical name (2

- (4

- methoxy

- [1,1’

- biphenyl]

- 3

- yl)

- methylethyl ester 1,1'

- biphenyl, 4

- methoxy

Chemical Abstract Service number 149877

- 41

- 8 613

- 37

- 6 1
Empirical Formula C 17 H 20 N 2 0 3 C 13 H 12 0 Molecular weight 300.36 184 Aqueous Solubility 3.76 mg/L (20oC) 27.7mg/L 2 (25oC) pK

a 12.94 data not available

Vapor Pressure (25 ° C) <1 x 10 - 7 mmHg 3.76 x 10 - 4 mmHg 3 (25oC)

Octanol

- water partition coefficient (log K

ow ) 3.4 3.8



### Base d on available environmental fate data, the parent compound, bifenazate is expected to be slightly mobile, but not persistent in the environme nt (Table 4 ). It is expected to rapidly dissipate in aquatic environments as the result of both hydrolysis (t 1/2 

### = 7.7 hours at pH 7) and direct aqueous photolysis (t 1/2 

### = 16 hours). Photodegradation of bifenazate in soil is not expected because there was rapid degradation of bifenazate in the dark control of photodegradation in soil study. Major hydrolysis degradation products (>10% of applied radioactivity) of bifenazate include d iazenecarboxylic acid, 2

- [4 -methoxy(1,1’-biphenyl)-3- yl],

1- methylethyl ester (D3598 ), [1,1’-Biphenyl]-3,4-diol (D9472), and 4-methoxybiphenyl (D1989). A major photodegradation product in water is 4 -Methoxy-[1,1’-biphenyl]-3-ol (D9963).

Table 4

. Select Physical, Chemical and Environmental Properties of Bifenazate and the Major Degradate of Exposure Concern, D1989.

Environmental Fate Properties
Environmental Fate Properties Bifenazate D1989

Hydrolysis half

- lives (pH 5, pH 7 , pH 9) t 1⁄2 = 2.68 days, 7.7 hours , 0.45

hours data not available

Aqueous Photolysis half

- life t 1⁄2 = 16.2 hours data not available Soil Photolysis half

- life Stable 1 data not available

Aerobic Soil Metabolism half

- life t 1⁄2 = 7.3 hours t 1⁄2 = 24 .4 days 3
Anaerobic Aquatic Metabolism half

- life t 1⁄2 = 78 days data not available Mobility Immobile 2 K

oc = 3011

– 6189 4

Terrestrial Field Dissipation half

- life t 1⁄2 = 5 days No residues detected after 60 days, or below 30 cm soil depth,

under field conditions 4

1- Rapid degradation of bifenazate was observed in the dark control , which indicates photodegradation on soil is not a probable route of dissipation

. 2- Immobile mobility classification based on soil column leaching study (MRID 44464955).

3- Aerobic soil metabolism degradation half

- life for D1989 (MRID 45144002)

4- Batch equilibrium coefficients for D1989 (MRID 44464956)

1 PMRA Regulatory Note REG 2006

- 01 

### http://www.pmra -arla.gc.ca/english/pdf/reg/reg2006-01-e.pdf

2 EPI Suite 2000 (v3.12) WSKOW v.141

3 EPI Suite 2000 (v3.12) MPBPWIN v1.41 (modified grain method)

4 PMRA Regulatory Note REG 2006

- 01 

### http://www.pmra -arla.gc.ca/english/pdf/reg/reg2006-01-e.pdf

### Page 7 of 32 

### Bifenazate is rapidly degraded in aerobic soil (t 1/2 

### = 7.2 hours) into the major degradate 4- methoxybiphenyl (D1989). The other major degradation product in aerobic soil is D3595. In anaerobic environments, bifenazate is degraded with a half-life of 77.9 days. Major degradation products in anaerobic environments include (1,1’-Biphenyl)-4-ol (A1530) and desmethyl D3598. Structures of degradation products are shown in Appendix E

.

Based on soil column leaching data and HPLC soil column Koc estimation , b ifenazate i s slightly

mobile in most soils

, as is th e major degradate D1989 (K

oc 

### =3011-6189). The low vapor pressure and Henry’s Law constant limits the potential of bifenazate to volatilize from soil and water. Given that bifenazate is rapidly hydrolyzed, photodegraded, and microbially- degraded, it has lo w potential for bioaccumulation.

Terrestrial field dissipation studies in Washington and North Carolina confirm laboratory stud y results that bifenazate degrades rapidly (t 1/2 

### =5 days) and is immobile in bare-ground soil. Major degradation products, D1989 or D3598, were detected at a maximum concentration of 0.03 mg/kg. No bifenazate residue detections were found in soil depths > 6 inches.

3.1. Transformation Products

An analysis of the degradation product profiles among laboratory studies indic ates a common degradation profile for bifenazate; it degrades to form D3598, which is a precursor to D1989, D9472, D9963, and A1530 ( Table 5 )

. Additionally, a large fraction of 14 

### C residue was detected (51.5-73.8%) in bound soil/sediment fractions. D ata indicate that the biphenyl moiety of bifenazate is prone to incorporation into soil/sediment organic matter.

Table 5: Maximum Concentration of Bifenazate Degradation Products in Environmental

Fate Studies

Environmental Fate Study MRID Study Conditions Degradation

Product Maximum Percentage Formed (%) Hydrolysis 44464952 pH=4 D3598 22@14 days

D1989 9.7@14 days

D9472 83.6@ 30 days pH=7 D3598 63@ 1 day

D1989 7.2@339 hours

D9472 43.4@2 days

D9963 5.2@768 hours pH=9 D3598 23.5@1.8 hour

D1989 9.9@20.6 hours

D9472 64.1@2.8 hours

D9963 6.6@18.6 hours Photolysis in Water 44464953 Dark Control; pH=5 D3598 55.9@78 hours

D9472 45.5@150 hours

D1989 11.6@150 hours
Irradiated; pH=5 D3598 74.4@27.9 hours

D9472 15.9@149.8 hours

D1989 13.8@53.8 hours

D9963 31.7@150.5 hours Photolysis on Soil 44522601 Dark Control;SL;pH

- 6.7 D3598 77.5@2 hours

### Page 8 of 32 D1989 22.1@3 days Irradiated; SL;pH

- 6.7 D3598 84.3@2 hours

D1989 11.2@3 days

Aerobic Soil

Metabolism 44464954 SL; pH=6.9;1.9%OM D3598 92@0.5 hours

D1989 26.8@3days Anaerobic Aquatic

Metabolism 44522602 Loam sediment (pH=6.6;

6.9% OM) with natural water (pH=7) A1530 24.@294 days Desmethyl 3598 14.7@231 days

D3598 3.7@ 0 days

Terrestrial Field Dissipation 44464958 Washington State; Sand soil; bareground; application rate (0.6 lb

a

. i

. /A) D1989 or D3598 1 0.02 mg/kg @ 4 days posttreatment

in 0

- 6 inch soil

44464957 North Dakota; SL soil; bareground; application rate (0.61 lb a .i. /A) D1989 or D3598 1 0.03 mg/kg (10% of applied) @ 7 days posttreatment

in 0

- 6 inch soil

1 Common moiety extraction for D3598 and D1989

.



### Experimental environmental fate data have been submitted for D1989. D1989 degraded in loamy sandy soil with a half -life of 24.4 days (MRID 45144002). It is slightly mobile (Koc=3011-6189) in mineral soils (MRID 44464956). However, D1989 may exhibit sufficient persistence and hydrophobicity (log Kow=3.8) to allow bioaccumulation. Although the vapor pressure and Henry’s Constant of D1989 indicate volatilization as a potential route of dissipation, volatilizat ion of D1989 was not observed in laboratory studies.

Environmental fate properties for other degradation products were predicted using EPISuite ( Table 6 ). This model simulation indicates that degradation products are not expected to be readily biodegra dable. However, D3598 degraded with a single first order half-life of 9.242 hours in aerobic soil (MRID 44464954). T he mobility of the degradation products ranges from moderately mobile to slightly mobile . Additionally, the degradation products except D9472 have

K
ow 

### values exceeding the OPP/EFED trigger for potential bioaccumulation.

Table 6: Environmental Fate Properties of Bifenazate Degradation Products as Determined by

EPIsuite

Property Degradation Product

D3598 D1989 D9963 D9472 A1530 Molecular Weight (g/mol) 298.34 184.24 200.24 186.21 170.21 Vapor Pressure ( mm Hg ) 6.08E

- 7 3.76E

- 4 7.35E

- 6 7.89E

- 7 1.73E

- 5 Henry ’ s Constant (atm

- m3/mol) 1 6.001E

- 8 3.29E

- 6 1.977E

- 8 2.422E

- 10 8.977E

- 9 Solubility ( mg /L) 3 .9 77 27.7 94.94 798.2 431.6 Log Kow 4.10 3.84 3.10 2.80 3.20

Koc (L/kg) 7485 1274 728.7 642 727.7 Ready Biodegrada tion No No No No No

1- Henry Constant

- Calculate d using v apor p ressure/ w ater s olubility



### 4. Receptors

Tables 7 and 8 provide a summary of the aquatic and terrestrial taxonomic groups, respectively,

and the most sensitive surrogate species tested to characterize the potential acute and chronic

### Page 9 of 32 

### ecological effects of bifenazate . In addition, the tables provide a prelimina ry overview of the potential acute toxicity of bifenazate by providing the a cute toxicity classifications. T oxicity data for degradates have recently been submitted but have not been fully reviewed. A preliminary summary of the degradate data is provided in Appendix F

.

4.1. Effects to Aquatic Organisms

Based on the available data, bifenazate is classified as “highly toxic” to freshwater and estuarine/marine fish and invertebrates on an acute exposure basis. Despite the high toxicity, the exposure was low enough in previous assessments that there were no LOC exceedances for fish

or freshwater invertebrates on an acute exposure basis. For estuarine/ marine invertebrates, there

were LOC exceedance s on an acute exposure basis (acute RQs range from 0.01 -to 0.16). Data

are not available to asses s the risk from chronic exposure to fre shwater fish and also to

estuarine/marine fish and invertebrates

.

For vascular aquatic plants, there we re no effects reported at any of the test concentrations in the duckweed ( Lemna gibba) study ( EC 50 

### = >3.82 mg/L) and for non- vascular plants, an EC 50 

### = 0.89 mg/L (NOAEC = 0.252 mg/L) was reported for green algae (Selenastrum capricornutum) based on a reduction in cell density.

Table 7 . Summary of the Most Sensitive Endpoints from Aquatic Toxicity Studies for Bifenazate

Taxonomic Group Study Type Surrogate Species Toxicity Values (all units in terms of measured a.i.) MRID and

Classification Acute Toxicity

Classification

Freshwater

fish Acute Bluegill sunfish LC 50 = 0.58 mg/L 44464931 (Acceptable) Highly toxic (Lepomis macrochirus) NOAEC = 0.30 mg/L Endpoint: survival

and sublethal effects

Chronic No Data

Freshwater

Invertebrates Acute Water flea EC 50 = 0.50 mg/L

44464933 Highly toxic

(Daphnia magna) NOAEC = ND Endpoint:

Immobilization (Acceptable)

Chronic Water flea NOAEC = 0.15 mg/L

45052216

(Daphnia magna) LOAEC = 0.27 mg/L Endpoint: reproductive and growth effects (Supplemental 1 )

Estuarine/

Marine Fish Acute Sheepshead

minnow LC 50 = 0.416 mg/L

45052214 Highly toxic (Cyprinodon variegatus) NOAEC = 0.136 mg/L Endpoint: Survival (Acceptable)

### Page 10 of 32 Chronic No data

Estuarine/

Marine

Invertebrates Acute Saltwater mysid LC 50 = 0.058 mg/L

45052213 Very highly

toxic (Americamysis bahia) NOAEC = 0.04 mg/L Endpoint: Survival (Supplemental 2 )

Chronic No data

Aquatic

Plants Non

vascular Green algae EC 50 = 0.89 mg/L

45052219

(Se lenastrum capricornutum) NOAEC = 0.252 mg/L Endpoint:

Reduction in cell density (Acceptable)

Vascular Duckweed EC 50 = >3.82 mg/L

45052218

(Lemna gibba) NOAEC = 3.82 mg/L

No effect on frond

number (Acceptable)

1 Classified as “Supplemental” because the water samples were not centrifuged or filtered prior to analysis even though a precipitate was observed in the mixing chamber of the highest concentration.

2 Classified as “Supplemental” because the water samples were not centrifuged or filtered prior to analysis even though a precipitate was observed in the mixing chambers and the mean measured concentrations at test termination were not maintained

at >70% of the nominal concentrations.



### 4.2. Eff ects to Terrestrial Organisms

Parent b ifenazate is classified as “practically non -toxic” to mammals and “slightly toxic” to birds on an acute exposure basis. On a subacute basis, bifenazate was classified as “moderately toxic”

to the mallard with a LC 50 

### of 656 mg/kg-diet. For chronic exposure to mammals, there was a reduction in body weight and cumulative weight gain for the males and females in the F1 generation in a two -generation reproductive study with the laboratory rat ( NOAEC = 20 mg/kg

diet). It should be noted that this endpoint f or mammals is different from what was used in previous assessments (>200 mg/kg- diet)

, because the >200 mg/kg-diet endpoint was based only on effects to reproduction and did not consider the reduction in body weight. Bec ause body weight change is an apical endpoint considered by EFED, the NOAEC value of 20 mg a.i./kg-bw

will be the value used in the upcoming risk assessment. For birds, c hronic effects were reported based on a reduction of eggs laid and set (LOAEC = 65 mg/ kg

- diet/NOAEC =20 mg/kg

- diet). In the previous assessments, there were LOC exceedances for birds on both an a cute (RQs from <0.01- 0.48) and chronic (RQs from 0.6 -16) exposure basis. For the upcoming assessment, it is anticipated that there will be also be LOC exceedances for mammals (based on the revised endpoint) on a chronic exposure basis.

Acute contact honeybee studies indicate that bifenazate is moderately toxic to honey bees (LD 50 

### 7.8 μg/bee). For terrestrial insects, EFED currently uses the honeybee data as a surrogate For

t errestrial plant s, the available t oxicity studies with monocots and dicots indicate that bifenazate had no adverse effects on seedling emergence and vegetative vigor at the hig hest test

co ncentration (2 lb a.i. /A ).

### Page 11 of 32 Table 8 . Summary of the Most Sensitive Endpoints from Terrestrial Toxicity Studies for Bifenazate

Taxonomic Group Study Type Surrogate Species Toxicity Values (all

units in terms of

measured a.i.) MRID and

Classification Acute Toxicity

Classification

Mammals Acute Oral Laboratory rat LD 50 >5000 mg/kg

- bw 44464934

(Acceptable) Practically non

toxic

Chronic Laboratory rat NOAEL 20 mg/kg

- diet 45076503

LOAEL= 80 mg/kg

- diet Endpoint: Decreased body weight and cumulative body weight gains in

males and females (Acceptable)

Birds Acute Oral Bobwhite quail LD 50 = 1032 mg/kg bw 44464928

(Colinus virginianus) NOAEL= Not determined Endpoint: Mortality and

sublethal effects (Acceptable)

Slightly toxic

Subacute Dietary Mallard LC 50 = 656 mg/kg

- diet 44464929

(Anas platyrhynchos) Endpoint: Survival (Acceptable) Moderately

toxic

Mallard NOAEC = 20 mg/kg

- diet 44872901

Chronic (Anas platyrhynchos) LOAEC = 65 mg/kg

- diet Endpoint: Reduction in # eggs laid and set per

female (Acceptable)

Terrestrial

Insects Acute

Contact Honey Bee LD 50 = 7.8 μg/bee

NOAEC = 2.7 μg/bee Endpoint: Survival 44462315

(Apis mellifera) (Acceptable) Moderately

toxic

Terrestrial

Plants Seedling Emergence Monocot

- corn EC 25 = >2.0 lb a.i./A 45052217

NOAEC = 2.0 lb a.i./A (Acceptable)

Seedling Emergence Dicot

- soybean EC 25 = >2.0 lb a.i. /A 45052217

NOAEC = 2.0 lb a.i. /A (Acceptable)

Vegetative

Vigor Monocot

- wheat EC 25 = >2.0 lb a.i. /A 45076502

NOAEC = 2.0 lb a.i. /A (Acceptable)

Vegetative

Vigor Dicot

- cabbage EC 25 = >2.0 lb a.i. /A 45076502

NOAEC = 2.0 lb a.i. /A (Acceptable)

1 Birds represent surrogates for terrestrial

- phase amphibians and reptiles.

### Page 12 of 32 

### 4.3. Ecological Incidents

As of July 18, 2012, the Ecological Incident Information System (EIIS, version 2.1), which is maintained by the Agency’s Office of Pesticide Programs, returned one terrestrial plant incident

in California attributed to bifenazate use with “possible” certainty ( Table 9 ). Incident # I016036-

006 

### occurred in 2004 when a registered agricultural use product containing bifenazate was applied to almonds. Fifty -four acres of basil w ere reported to be damaged from possible spray

drift from the airblast treatment to almonds.

Table 9 . Ecological Incidents Associated with Bifenazate

Incident

Number Taxa

Involved Magnit u de Year Location Use Legality

of Use Certainty Category Residues Other

Chemicals

Involved

I016036

- 006 Terrestrial

Plant 54 Acres (Basil) 2004 CA Almonds Registered

Use Possible None reported None reported



### No ecological incidents were reported in the Avian Monitoring Information System (AIMS) database, which is maintained by the American Bird Conservancy, or in the IDS Aggr egate Incident Reports’ database maintained by EPA

.

5. Conceptual Model

The environmental fate data for bifenazate show rapid degrad ation in terrestrial and aquatic environments. This rapid degradation results in formation of toxic degradation products with the potential for environmental exposure. Degradation products of bifenazate are D-1989, D-3598, D-9963, D-9472 and A-1530. Previous risk assessments have focused on bifenazate and the degradation product D-1989; however, additional information from the registrant indicate s that

D-3598 has similar toxicity to bifenazate. Additionally, several ecotoxicology studies have been

submitted for degradates D -1989, D-3598, and D-9472. Based on a preliminary review of the studies, the data tentatively suggest (until a full review of the studies has been completed ) that D

1989, D-3598, and D-9472 are generally similar in toxicity to bifenazate. Data are not available for degradate A -1530, however, since this degradation product is only formed in anaerobic aquatic environments it will not be included as a stressor of concern. While data are also not

available for D

- 9963, g iven the similarities in structure of D -1989, D- 9963, D-9472, in the absence of data, it is assumed that D

- 9963 will also exhibit similar toxicity. B ased on the environmental fate data and use information, potential routes of exposure for bifenazate and its degradation products are as follows:

• Off

- site movement of bifenazate is expected to be predominately by spray drift;

• Rapid degradation of bifenazate is expected to limit runoff and leaching potential;

• D egradation products of bifenazate are expected to be more persistent than bifenazate;

• Off

- site movement of bifenazate degradation products may be by runoff or erosion;

• B ifenazate residues in soil are incorporat ed into soil organic matt er;

• QSAR analysis indicates all degradation products except D9472 have K

ow 

### values exceeding the bioaccumulation (log K

ow 

### =3) trigger; and

• Volatilization may be a route of dissipation for D1989.

### Page 13 of 32 

### 6. Analysis Plan

In order to address the risk hypothesis, the potential for adverse effects on the environment will be estimated. The use, environmental fate and ecological effects of bifenazate and its degradation products (D-3589, D-1989, D-9963, and D-9472) will be characterized and integrated to a ssess the overall risks. A total toxic residue approach will be used to assess the exposure to bifenazate ( FIFRA SAP , 2008). This assessment process will assume that ecotoxicity of the degradation products - D-3589, D-1989, D-9963, and D-9472 is equivalent to bifenazate.Risk quotients (RQ) will be derived for total toxic residues (bifenazate, D-3589, D-1989, D9963, and D-9472) by dividing estimated environmental concentrations (EEC) by the most sensitive endpoint from the relevant, availab le toxicity data for bifenazate

6.1. Stressors of Concern

The residues of concern in this assessment will include bifenazate and its degradation products D-3589, D1989, D-9963, and D-9472. HED has identified the bifenazate degradation product

D-1989 as a residue of concern and the registrant Chemtura has indicated that the degradation product D-3589 has insecticidal activity. Additionally, several aquatic ecotoxicology studies are now available for degradates D -1989, D-3598, and D-9472. Based on a pr eliminary screen of

the submitted studies , the data suggests that the degradates are generally similar in toxicity to

bifenazate for aquatic plants and animals. While f or fish and aquatic invertebrates, the EC/LC 50 

### values for D-3598 were generally an order of magnitude lower ( i.e. more toxic) than the respective values for bifenazate this is within the normal range of variability that may occur for

the same guideli ne test ( especially when different species were used

- as i s th e case with the fish

data ). In addition to the aquatic toxicity data, data for acute toxicity to the earthworm ( Eisenia fetida ) were submitted for Bifenazate, D-1989, and D-3598. Based on a preliminary review of

the data

, the degradates may be slightly more toxic to the earthworm than the p arent , however,

terrestrial invertebrates are not assessed quantitatively in EFED assessments. Degradate D -9963

is included as a residues of concern because it is a major degradate and is similar in structure to

D-1989 and D- 9472 (see Appendix E for the chemical structures). Therefore, based on the information available at this time, the degradates D-1989, D-3598, D-9472, and D-9963 are assumed to be equal ly as toxic as bifenazate and a total toxic residue approach will be used to

estimate the summed environmental concentration of bifenazate, D -1989, D-3589, D-9472, and D-9963 (FIFRA SAP, 2008 ). Appendix F provides a summary of the degradate toxicity data in comparison to bifenazate.

6.2. 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

. The models used to generate aquatic estimated environmental concentrations (EEC) are the Pesticide Root Zone Model (PRZM) coupled with the EXposure Analysis Model System (EXAMS). Model input values will be consistent with the most recent version of the Input

### Page 14 of 32 

### Parameter guidance (current version 2.1; USEPA 2009). The model used to produce terrestrial

EECs on food items is T- REX. Using the TREX model, we will assume that the conservative

half -life value of 35 days for foliar residue dissipation will capture th e parent and degradates

, unless data becomes available to suggest that the 35 -day half- life is inadequate. The model used to derive EECs relevant to terrestrial and wetland plants is TerrPlant. The AgDRIFT spray drift model (v2.01; May 2001) is used to assess exposures of organisms to b ifenazate deposited on terrestrial or aquatic habitats by spray drift. KABAM (K OW 

### (based) Aquatic BioAccumulation Model) v.1.0 will be used to estimate potential bioaccumulation of hydrophobic organic pesticides such as D-19 89 in freshwater aquatic food webs and subsequent risks to mammals and birds via consumption of contaminated aquatic prey. These models are parameterized using relevant reviewed registrant

- submitted environmental fate data. Because bifenazate and its degradation products D-1989, D-3589, D-9472, and D-9963 are assumed to have similar toxicity to terrestrial and aquatic organisms, a total toxic residues approach will be used in the exposure modeling ( FIFRA SAP , 2008). The predicted estimated environmental concentrations of total

toxic residues (bifenazate, D-1989, D-3589, D-9472, and D-9963 will be used to calculate risk quotients.

For problem formulation, screens were conducted for the potential exposure from drinking water and inhalation. For drinking water, the Screening Imbibition Program (SIP v. 1.0, Released June 15, 2010) was used to calculate an upper bound estimate of exposu re. Exposure from drinking water alone was not determined to be a potential pathway of concern for avian or mammalian species on an acute basis and on a chronic exposure basis drinking water alon e was not a concern for mammals; however, it is a potential concern for birds ( Appendix A ). This modeling does not take into account that drinking water may contribute to a total exposure that has the potential for

effects on non- target animals when aggregated with other exposure pathways (dietary food sources, dermal, inhalation). Because there is a high degree of conservatism in the SIP 1.0 exposure estimate, there is limited expectation that use scenarios no t triggering a SIP 1.0 concern would contribute significantly to aggregate risks from water plus diet when a refined water exposure model is incorporated in the actual quantitative risk assessment. Detailed information about SIP v. 1.0, as well as the tool, can be found on the EPA’s website at http://www.epa.gov/pesticides/science/models_pg.htm#terrestrial

.

The S creening T ool for I nhalation R isk (STIR v.1.0, November 19, 2010 ) was used to calculate an upper bound estimate of exposure from inhalation. Based on the results of the STIR model, inhalation exposure alone was not determined to be a potential pathway of concern for avian or mammalian species on an acute basis ( Append ix B ). Inhalation exposure via spray drift and/or

the 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

effects to non- target animals. However, the Agency does consider the relative importance of other routes of exposure in situations where data indicate that pesticide exposures through other routes may be potentially significant contributors to wildlife risk (USEPA, 2004). The risk characterization section will discusses the impact of the consideration of other routes of exposure that have been identified as potentially important, and the degree of certainty associated with screening -level risk assessment conclusions. Detailed information about STIR v.1.0, as well as the tool, can be found on the EPA’s website at:

### Page 15 of 32 

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

.

6.3. Measures of Effect

Toxicity data presented in Section 4 of this problem formulation will be used to calculate risk quotients. Any additional information submitted by the 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 ECOTOXicology database ( ECOTOX) (USEPA, 2007 c ), which employs a literature search engine for locating chemical toxicity data for aquatic life, terrestrial plants,

and wildlife.

6.4. Endangered Species Assessments

Consistent with the Agency’s responsibility under the Endangered Species Act (ESA), the Agency will evaluate risks to federally listed threatened and/or endangered species (“listed species”) from registered uses of pesticides in registration review . These assessments wi ll be conducted in accordance with standard EPA procedures and good scientific judgment. The process for evaluating potential risks to listed species is further described at http:/ /www.epa.gov/oppfead1/endanger/litstatus/riskasses.htm

.

6.5. Endocrine Disruptor Screening Program

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

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

.

7. Preliminary Identification of Data Gaps

7.1. Environmental Fate

The environmental fate database for bifenazate is complete to provide an understanding of dominant environmental dissipation pathways and to allow quantification of estimated environmental concentrations in aquatic environments. There are, however, several environmental fate studies, including (835.4300) Aerobic Aquatic Metabolism, (835.1230)

Ads orption-Desorption, (850.1730) Fish Bioaccumulation, and Analytical Methods in Water (835.6100) that remain as uncertainties

. The registrant has submitted studies on estimation of Koc for bifenazate and D3598 (MRID 489295140, 48929514), aerobic aquatic metabolism, anaerobic soil metabolism (MRID 48929516), photodegradation in water (MRID 48929512), activated sludge respiration inhibition test (MRID 48929521), ready biodegradability by the modified sturm test (MRID 48929511), gas phase oxidation and half-life in troposphere (MRID 48929517), quantum yield calculation (MRID 48929518), and aquatic exposure modeling (MRID 48929519). These data, except for the activated sludge respiration inhibition test (MRID

### Page 16 of 32 

### 48929521), ready biodegradability by the modified sturm test (MRID 48929511), gas phase oxidation and half-life in troposphere (MRID 48929517), will be reviewed for the risk

ass essment. Because D1989 is a residue of concern in both the human health and ecological risk

assessments , submission of an aerobic aquatic metabolism study for D1989 is expected to reduce uncertainty of the persistence of D1989 in water. Also, an analytical method for bifenazate and its degradation products (D1989 and D3589) are needed. Additionally, the aerobic soil metabolism study (MRID 44464954) was conducted using one soil , whereas c urrent guidance

recommends four soils. Submission of studies evalua ting the aerobic aquatic metabolism of

D1989 and aerobic soil metabolism of bifenazate would be expected to reduce uncertainty in assessing exposure to bifenazate and its degradates.

Bifenazate degrades to form the degradation products D-3598, D-1989, D-9472, and D- 9963.

T hese degradation products are expected to exhibit ecotoxicity similar to bifenazate. Additionally, D1989 has been identified as a residue of concern in the human health risk

assessment. Because e xposure concentrations of bifenazate residues (bifenazate, D1989, and D3598, D-9472, and D-9963) will be estimated using a total toxic residues approach, cumulative

half

- lives of total toxic residues in soil and water, as well as batch equilibrium coefficients of individual residues, are needed for exposure modeling. A erobic soil metabolism data for D -3598

are not needed because the cumulative half

- life of TTR can be estimated from existing aerobic soil metabolism data for bifenazate (MRID 44464954 ). Because the re are no adsorptiondesorption ( 835.1230) data for D -3598, the Koc for D- 3598 will be estimated using EPIsuitemodeling. Aerobic soil metabolism and adsorption-desorption data have been submitted for D1989.

Table 10, 11, and 12 id entify environmental fate studies by MRID that offer data for each data requirement, as well as study classifications and whether or not further data are needed in order to support risk assessment.

Table 10. S tatus of Environmental Fate Data for Bifenazate

OCSPP

Guideline Data Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to

conduct risk

assessment? Comments

835.2120 Hydrolysis 44464952 Supplemental No

835.2240 Aqueous photolysis 44464953 Acceptable No

45052308 In Review

835.2410 Soil photolysis 44522601 Acceptable No

835.4100 Aerobic soil

metabolism 44464954 Acceptable

No The available study only tested one soil.

Current guidance recommends testing

four soils. Additional soil metabolism tests will reduce uncertainty and help to refine the ecological exposure and drinking water exposure assessments.

835.4200 Anaerobic soil

metabolism (None) No Anaerobic aquatic metabolism data are

available f or bifenazate

. Submission of

anaerobic soil metabolism data are not expected to alter the environmental fate profile for bifenazate.

### Page 17 of 32 OCSPP

Guideline Data Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to

conduct risk

assessment? Comments

835.4300 Aerobic aquatic

metabolism (None) No Although conservative assumptions can be made without data, aerobic aquatic

metabolism data for bifenazate and D

1989 may help to refine exposure

concentrations of bifenazate residues in aquatic environments and surface source drinking water.

835.4400 An aerobic aquatic

metabolism 44522602 Supplement al No

44 8 59702 In Review

835.1230

835.1240 Soil Column Leaching 44464955 Acceptable No Although quantitative estimates of soil:water partitioning are not possible from soil column leaching studies, the rapid degradation of bifenazate is expected to limit environmental

exposure.

835.1410 Volatility

– laboratory (None) No Volatility study for bifenazate is not needed because of a low vapor pressure

835.6100 Terrestrial field dissipation 45052306 In Review No

44464957 Not Acceptable

44464958 Acceptable

Analytical

method

in soil 45052309 In Review

45052307 In Review

Analytical

method in water (None) NA Y es

850.1730 Fish

bioconcentration (None) NA Yes



### Table 11. Status of Environmental Fate Data for the Degradate D1989

OCSPP

Guideline Data Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to

conduct risk

assessment? Comments

835.4100 Aerobic soil

metabolism 45144002 In Review No Degradation product is expected to exhibit equal ecotoxicity as parent. Also,

it is identified as a residue of concern in

the human health risk assessment. 835.1230 Adsorption/ desorption 44464956 Acceptable No

### Page 18 of 32 Table 12. Status of Environmental Fate Data for the Degradate D3598

OCSPP

Guideline Data Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to

conduct risk

assessment? Comments

835.4100 Aerobic soil

metabolism (None) No An aerobic soil metabolism half

- life for

D3598 was determined from the aerobic soil metabolism study for bifenazate (MRID 44464954 ).

835.1230 Adsorption/ desorption (None) No EPIsuite estimates of Koc will be

considered in the exposure assessment.



### 7. 2. Ecological Effects

Data are not available to assess chronic risk to freshwater or estuarine/marine fish, or to

estuarine/marine invertebrates. According to the acute toxicity data for fish, bifenazate is classified as “highly toxic” to fish . Additionally, the chronic risk identified for other

v ertebrate taxa (birds and mammals) also suggests that there is a poten tial for adverse effects to fish on a chronic exposure basis. Therefore, there is a need for chronic toxicity data for fish to provide a definitive endpoint for risk assessment. The recommended toxicity test is

the Chronic Freshwater Fish Toxicity (850.1400) test . Chronic data for estuarine/marine fish

are not required at this time because the freshwater fish data can serve as a surrogate given

that the acute toxicity data were similar for the freshwater and estuarine/marine fish. For invertebrates, an acute

- to -chronic ratio (ACR ) was used in previous assessments to estimate the chronic toxicity to estuarine/marine invertebrates . When using this value as a proxy,

chronic risk to estuarine/marine invertebrates was below the LOC. Therefore, chronic toxicity data are not required for estuarine/marine invertebrates at this time.

Acceptable acute avian oral toxicity data were submitted for exposures of bobwhite quail and

mallard duck to bifenazate, respectively; however, data are not available for passerines, which are required under the 40 CFR Part 158 (Oct. 26, 2007) data requirements for conventional pesticides (72 FR 60934; USEPA 2007 a ). The Part 158 data requirements specify that acute avian oral toxicity dat a be submitted for either a mallard duck or bobwhite quail, and for a passerine species. The exceedance of the acute and chronic LOCs based on

the other non- passerine toxicity tests substantiates the need for these data. Therefore, an avian oral toxicity t est conducted with a passerine ( OCSPP Guideline 850.2100) is needed

. EFED recommends that a passerine study protocol be submitted for review by the Agency prior to initiation of this study. Table 13 provides a summary of the status of effects data for

Bife nazate.

Degradate ecotoxicity data have been submitted for degradates D

- 1989, D -3598, and D-9472. These studies have not been fully reviewed at this time but provide a tentative weight of evidence to assume equal toxicity of the degradates and the parent bifenazate. Additional degradate toxicity information is not needed at this time. A summary of the available degradate data is provided in Appendix F

.

### Page 19 of 32 Table 13

. Status of Ecological Effects Data for Bifenazate

Ecological Toxicity Data Requirements for Bifenazate

Guideline # Data Requirem e nt Submitted

Studies

MRID # Study

Classification s Are data

needed for

risk

assessment? Comments

850.2100 Avian acute oral LD 50 (bobwhite quail) 44464928 Acceptable Yes Acute oral toxicity

data for a passerine species will be used to refine the screening

level assessment

, by determining whether

there are differences in avian species sensitivity to

bifenazate.

850

- 2200 Avian subacute dietary LC 50 (bobwhite quail) (mallard duck) 44464929

44464930 Acceptable Acceptable No

No

850

- 2300 Avian reproduction (bobwhite quail) (mallard duck) (mallard duck) 45052212

44872901

45144003 Supplemental Acceptable Supplemental No

No

No

850

- 1075 Freshwater fish acute LC 50 (bluegill sunfish ) (rainbow trout) 44464931

44464932 Acceptable Acceptable No

No

850

- 1300 Freshwater invertebrate acute

EC 50 (daphnia) 44464933 Acceptable No

850

- 1075 Estuarine/marine fish acute

LC 50 (sheepshead minnow) 45052214 Acceptable No

850

- 1025;1035 Estuarine/marine invertebrate

acute EC 50 (eastern oyster) (mysid) 45052215

45052213 Acceptable Supplemental No

No

850

- 1400 Freshwater fish early life stage (fathead minnow) No Study Yes Chronic toxicity data

will be used to

determine the potential for

b ifenazate to a ffect

freshwater fish and

will also serve as a surrogate for

estuarine/marine fish.

850

- 1300 Freshwater invertebrate life cycle (daphnia) 45052216 Supplemental No

850

- 1400 Estuarine/marine fish life cycle (sheepshead minnow) No Study No A study is not being requested at this time

because the chronic freshwater fish study

recommended above

can serve as a surrogate.

### Page 20 of 32 850

- 1350 Estuarine/marine invertebrate life cycle (mysid) No Study No A study is not being requested at this time because a surrogate is available using the

acute and chronic

freshwater

invertebrate data and

the acute est./marine

invertebrate data to

estimate chronic toxicity.

850

- 1500 Freshwater fish full life cycle No Study Not applicable No A study is not being requested at this time

because neither of the following trigger

criteria were met : 1)

estimated EECs from previous assessments

for freshwater

invertebrates were

below the criteria of

0.1 of the NOAEC ( Note: a chronic fish early life stage study

is not available ). 2)

studies of other organisms do not clearly indicate that the reproductive physiology of fish may be affected.

850

- 1950 Aquatic Field Study No Study Not applicable No

81 -1 Acute mammalian oral LD 50 (rat) 44464934 Acceptable No

83 -3 Mammalian Developmental (rat) No Study No

83 -4 Mammalian Reproduction (rat) 45076503 Acceptable No

850

- 4100 Seedling Emergence

– Tier I 45052217 Acceptable No

850

- 4150 Vegetative Vigor

- Tier I 45076502 Acceptable No

850

- 4400 Aquatic plant algae (green algae) (blue

- green algae) 45052219

45052220 Acceptable Acceptable No

No

850

- 5400 Aquatic plant acute EC 50 (duckweed) 45052218 Acceptable No

850

- 3020 Acute honey bee contact LD 50 44462315 Acceptable No

Non

guideline Acute honey bee oral LD 50 No Study No

850

- 3030 Honey Bee Residue on Foliage 45052305 Acceptable No

850

- 3040 Honey Bee Field Testing for

Pollinator No Study No

### Page 21 of 32 8. References



### FIFRA Science Advisory Panel. 2008. Selected Issues Associated with the Risk Assessment Process for Pesticides with Persistent, Bioaccumulative, and Toxic Characteristics. http://www.epa.gov/scipoly/sap/meetings/2008/102808_mtg.htm

USEPA. 2004. Overview of the Ecological Risk Assessment Pro cess in the Office of Pesticide Programs. U.S. Environmental Protection Agency, Office of Prevention, Pesticides and Toxic Substances, Office of Pesticide Programs, Washington DC. January 23, 2004.

USEPA. 2007 c . ECOTOXicology Database. Office of Research and Development National Health and Environmental Effects Research Laboratory’s (NHEERL’s) Mid -Continent Ecology Division (MED). http://cfpub.epa.gov/ecotox/

.

USEPA, 2 011. BEAD Chemical Profile for Registration Review: Bifenazate (000586). U.S. Environmental Protection Agency, Office of Prevention, Pesticides and Toxic Substances, Office of Pesticide Programs, Washington DC. July 27, 2012.

USEPA, 2012. EFED Table 1 Re port. Bifenazate (000586). U.S. Environmental Protection Agency, Office of Prevention, Pesticides and Toxic Substances, Office of Pesticide Programs, Washington DC. May 8, 2012.

### Page 22 of 32 

## Appendices

– 

### Appendix A. Results of SIP

– 

### Appendix B. Results of STIR

– 

### Appendix C. Ecological Effects Bibliography

– 

### Appendix D. Environmental Fate Bibliography

– 

### Appendix E. Chemical Structures

Appendix A . Results of SIP

Table 1. Inputs

Parameter Value

Chemical name Bifenazate

Solubility (in water at 25 o C; mg/L) 3.76

Mammalian LD 50 (mg/kg

- bw) 5000

Mammalian test species laboratory rat

Body weight (g) of "other" mammalian species

Mammalian NOAEL (mg/kg

- bw) 1.6

Mammalian test species laboratory rat

Body weight (g) of "other" mammalian species

Avian LD 50 (mg/kg

- bw) 1032

Avian test species northern bobwhite quail

Body weight (g) of "other" avian species

Mineau scaling factor 1.15

Mallard NOAEC (mg/kg

- diet) 20

Bobwhite quail NOAEC (mg/kg

- diet)

NOAEC (mg/kg

- diet) for other bird species

Body weight (g) of other avian species

NOAEC (mg/kg

- diet) for 2nd other bird species

Body weight (g) of 2nd other avian species

Table 2. Mammalian Results

Parameter Acute Chronic

Upper bound exposure (mg/kg

- bw) 0.6467 0.6467

Adjusted toxicity value (mg/kg

- bw) 3845.8028 1.2307

Ratio of exposure to toxicity 0.0002 0.5255

Conclusion* Drinking water exposure alone is NOT a potential

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

mammals

### Page 23 of 32 Table 3. Avian Results

Parameter Acute Chronic

Upper bound exposure (mg/kg

- bw) 3.0456 3.0456

Adjusted toxicity value (mg/kg

- bw) 743.4833 0.9923

Ratio of exposure to acute toxicity 0.0041 3.0694

Conclusion* Drinking water exposure alone is NOT a potential
concern for birds Exposure through drinking water alone is 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 24 of 32 

### Appendix B . Results of STIR

Input

Application and Chemical Information

Enter Chemical Name Bifenazate

Enter Chemical Use Crop

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

If Spray What Type (enter ground or air) air

Enter Chemical Molecular Weight (g/mole) 300.36

Enter Chemical Vapor Pressure (mmHg) 1.00E

- 07

Enter Application Rate (lb a.i./acre) 0.75

Toxicity Properties

**Bird**

Enter Lowest Bird Oral LD 50 (mg/kg bw) 1032

Enter Mineau Scaling Factor 1.15

Enter Tested Bird Weight (kg) 0.178

**Mammal**

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

Enter Lowest Rat Inhalation LC 50 (mg/L) 4.4

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 ) 1.62E

- 03

Maximum 1

- hour Vapor Inhalation Dose (mg/kg) 2.03E

- 04

Adjusted Inhalation LD 50 5.06E+00

Ratio of Vapor Dose to Adjusted Inhalation LD 50 4.01E

- 05 Exposure not Likely Significant

Maximum Post

- treatment Spray Inhalation Dose (mg/kg) 7.20E

- 02

Ratio of Droplet Inhalation Dose to Adjusted Inhalation LD 50 1.42E

- 02 Exposure not Likely Significant

Results Mammalian (0.015 kg )

Maximum Vapor Concentration in Air at Saturation (mg/m 3 ) 1.62E

- 03

Maximum 1

- hour Vapor Inhalation Dose (mg/kg) 2.55E

- 04

Adjusted Inhalation LD 50 2.62E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 9.75E

- 07 Exposure not Likely Significant

Maximum Post

- treatment Spray Inhalation Dose (mg/kg) 9.06E

- 02

Ratio of Droplet Inhalation Dose to Adjusted Inhalation LD 50 3.46E

- 04 Exposure not Likely Significant

### Page 25 of 32 

### Appendix C . Ecological Effects Bibliography

Aquatic Animal s Fish Graves, W.C. and J.P. Swigert. 1997. D2341 Technical: A 96-Hour Flow-Through Acute Toxicity Test with the Bluegill ( Lepomis macrochirus ). Study performed by Wildlife International Ltd., 8598 Commerce Drive , Easton, Maryland 21601. Study report # 117A-101. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 444649-31

Graves, W.C. and J.P. Swigert. 1997. D2341 Technical: A 96-Hour Flow-Through Acute Toxicity Te st with the Rainbow trout ( Oncorhynchus mykiss ). Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, Maryland 21601. Study report # 117A-102. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 444649-32

Graves, W.C., and H.O. Kruger. 1999. D2341 Technical (bifenazate): A 96 hour flow-through acute toxicity test with the Sheepshead minnow ( Cyprinodon variegates) . Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, Maryland 21601. Study report # 117A-104. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT

06524.

MRID 450522-14

Invertebrates Drottar, K.R., and H. O. Krueger. 1999. D2341 Technical (bifenazate): A Flow- Through Life Cycl e Toxicity Test with the Cladoceran ( Daphnia magna ). Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, Maryland 21601. Study report # 117A-107. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 450522-16

Graves, W.C. and J.P. Swigert. 1997. D2341 Technical: A 48-Hour Flow-Through Acute Toxicity Test with the Cladoceran ( Daphnia magna ). Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, Maryland 21601. Study report # 117A-103A. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 444649-33

Graves, W.C., and H. O. Krueger. 1999. D2341 Technical (bifenazate): A 96-hour Shell Deposition Test with the Eastern Oyster ( Crassostrea virginica ). Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, Maryland 21601. Study report # 117A-106. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 450522-15

Graves, W.C., and H. O. Krueger. 1999. A 96 hour Flow- Through Acute Toxicity Test with the Saltwater Mysid ( Mysidopsis bahia . Study performed by Wildlife International Ltd., 8598

Commerce Drive , Easton, Maryland 21601. Study report # 117A-105. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 450522-13

### Page 26 of 32 

### Plants Drottar, K.R., and H. O. Krueger. 1999. D2341 Technical (bifenazate): A 7- day Toxicity Test with Duckweed ( Lemna gibba G3). Study performed by Wildlife Internatio nal Ltd., 8598

Commerce Drive , Easton, Maryland 21601. Study report # 117A-113. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 450522-18

Drottar, K.R., and H. O. Krueger. 1999. D2341 Technical (Bifenazate): a 96-hour Toxicity Test with the Freshwater Alga ( Selenastrum capricornutum ). Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, Maryland 21601. Study report # 117A-111. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 450522-19

Drottar, K.R., and H. O. Krueger. 1999. D2341 Technical (Bifenazate): A 96 -hour Toxicity

Test with the Freshwater Blue

- green Alga ( Anabaena flos-aquae ). Study performed by Wildlife International Ltd., 8598 Commerce Drive , Easton, Maryland 21601. Study report # 117A-109A. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 450522-20

Terrestrial Animal s Birds Pedersen, Carol A. 1996. Acute Avian Oral Toxicity (LD 50 

### ) Study with D2341 Technical in Bobwhite Quail. Study performed by Bio- life ® 

### Associates, Ltd., Neillsville, WI. Study ID 109- 025-03. Study sponsored by Uniroyal Chemical Company, Inc., Bethany, CT 06524-3402.

MRID 444649-28

Pedersen C.A. and B.R. Helsten. 1997. Acute Avian Dietary Toxicity (LC 50 

### ) Study with D2341 Technical in Bobwhite Quail. Study performed by Bio- life ® 

### Associates, Ltd., Neillsville, WI. Study ID 109-023-01. Study sponsored by Uniroyal Chemical Company, Inc., Bethany, CT

06524-3402. MRID 444649-29

Pedersen, C. A. and B.R. Helsten. 1997. Acute Avian Dietary Toxicity (LC 50 

### ) Study with D2341 Technical in Mallard Ducklings. Study performed by Bio- Life Associates, Ltd., Neillsville, WI. Study ID 109 -024-02. Study sponsored by Uniroyal Chemical Company, Inc., Bethany, CT 06524-3402. MRID 444649-30

Pedersen, Carol A. 1999. Avian Reproductive Toxicity Study with D2341 Technical in Bobwhite Quail. Study performed by Bio- life ® 

### Associates, Ltd., Neillsville, WI. Study ID 109- 031-07. Study sponsored by Uniroyal Chemical Company, Inc., Bethany, CT 06524-3402.

MRID 450522-12

Pedersen, Carol A. 1999. Avian Reproductive Toxicity Study with D2341 Technical in Mallard Duck. Study performed by Bio- life ® 

### Associates, Ltd., Neillsvill e, WI. Study ID 109-031-08. Study sponsored by Uniroyal Chemical Company, Inc., Bethany, CT 06524-3402. MRID

448729-01

### Page 27 of 32 

### Frey, L.T. et al., 2000. D2341 Technical.: A Reproduction Study with the Mallard. Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, MD 21601. Study ID 117-174. Study sponsored by Uniroyal Chemical Company, Inc., Bethany, CT 06524-3402.

MRID 451440-03.

Mammals Hoffman, G. 1996. Acute oral toxicity study with D2341 Technical in rats. Huntingdon Life

Scie nces, P.O. Box 2360, Mettlers Road, East Millstone, NJ 08875-2360. Study No. 95-1199, August 8, 1996. MRID 444649-34

Schardein, J.L. 1999. A Two-generation Reproductive Toxicity Study of D2341 in Rats. WIL Research Laboratories, Inc., Ashland, OH. Laboratory Study No.: WIL-155039. March 10,

1999. MRID 450765-03

Beneficial Insects Palmer, S.J. and J.B. Beavers. 1997. D2341 Technical: An Acute Contact Toxicity Study with the Honey Bee. Study performed by Wildlife International Ltd., 8598 Commerce Drive , Easton, MD 21601. Study ID 117-170. Study sponsored by Uniroyal Chemical Company, Inc., Bethany, CT 06524-3402. MRID 444623-15

Hummel, R.L. 1999. Final Report for the Evaluation of Toxicity of Residues of Bifenazate (UCC D2341 50 WP) on Alfal fa to Honey Bees (Apis mellifera)

. Study performed by Landis International, Inc., P.O. Box 5126, 3185 Madison Highway, Valdosta, GA 31603-5126. Laboratory report # 1l52lA002. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT 06524.

MRID 450523-05

Plants Porch, J.R. and H. Krueger. 1999. UCC -D2341- 50W: A Toxicity Test to Determine the Effects of the Test Substance on Seedling Emergence of Ten Species of Plants. Study performed by Wildlife International Ltd., 8598 Commerce Drive , Easton, Maryland 21601. Study report # 117-172. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Bethany, CT

06524.

MRID 450522-17

Porch, J.R. and H. Krueger. 1999. UCC-D2341- 50W: A Toxicity Test to Determine the Effects

of the Test Substance on Vegetative Vigor of Ten Species of Plants. Study performed by Wildlife International Ltd., 8598 Commerce Drive, Easton, Maryland 21601. Study report # 117-173. Study sponsored by Uniroyal Chemical Company, Inc. 74 Amity Road, Betha ny, CT

06524.

MRID 450765-02

### Page 28 of 32 

### Appendix D. Environmental Fate Bibliography

Abiotic Hydrolysis ( 835.2120 ) Shah, J. F. 1997. A hydrolysis study of [ 14 

### C]D2341. Laboratory Project ID: 95-0006. Unpublished study performed by Ricerca, Inc., Painesville, OH; and submitted by Uniroyal Chemical Co., Inc., Middlebury, CT. MRID 444649-52.

Findak, D.; DiFrancesco, D; Shah, J. 1999. A hydrolysis study of D2341: Lab Project

Number:6337-95-0006- EF -001:95—0006. Unpublished study prepared by Ricerca. MRID

44796701.

Direct Photolysis in Water ( 835.2240) Shah, J. 1997. Aqueous Photolysis of [ 14 

### C]D2341 at pH 5. Laboratory Project ID: 95-0032. Unpublished study performed by Ricerca, Inc., Painesville, OH; and submitted by Uniroyal Chemical Co., Inc., Middlebury, CT. MRID 444649-53.

Shah, J. 1998. Photolysis of [ 14 

### C]D2341: Lab Project Number:6394-95-0217- EF -001:95-0217-

EF -001:95-0217:96092. Unpublished study prepared by Ricerca. MRID 45052308.

D irect Photolysis in Soil ( 835.2410) Shah, J. F. 1997. Photolysis of [ 14 

### C]D2341 on soil. Laboratory Project ID: 96-0001. Unpublished study performed by Ricera, Inc., Painesville, OH; and submitted by Uniroyal Chemical Co., Inc., Middlebury, CT.

MRID 445226-01

Aerobic Soil Metabolism ( 835.4100) Lee, D. Y., N. R. Lentz, B. M. McCall and D. N. Pellack. 1996. Aerobic soil metabolism of
[ 14 

### C]D2341. Uniroyal Project No: 95233. Unpublished study performed by Ricerca, Inc., Painesville, OH; and submitted by Uniroyal Chemical Co., Inc., Middlebury, CT.

MRID 444649-54.

Nag, J.K. and R.R, Regis. 2000. Aerobic soil metabolism of 14C-4-methoxybiphenyl. Study No. 99009. Unpublished study performed and submitted by Uniroyal Chemical Company, Registration Chemistry Section, Crop Protection R & D, Middlebury, CT. MRID 45144002.

An aerobic Aquatic Metabolism ( 835.4400)

Lent z, N. R. 1998. Anaerobic aquatic metabolism of [ 14 

### C]D2341. Laboratory Project ID: 95- 0115. Unpublished study performed by Ricerca, Inc., Painesville, OH; and submitted by Uniroyal Chemical Co., Inc., Middlebury, CT. MRID 445226-02.

Lentz, N. 1998. Anaerobic Aquatic Metabolism of 14 

### C]D2341: Lab Project Number: 95235:95-

0115:6492-95-0115- EF -001. Unpublished study prepared by Ricerca, Inc. MRID 44859702.

### Page 29 of 32 

### Leaching – Soil Adsorption/Desorption (835.1230/835.1240) Huhtanen, C. F. 1997. Soil adsorption and desorption of [ 14 

### C]D1989. Laboratory Project ID: 96-0056. Unpublished study performed by Ricerca, Inc., Painesville, OH; and submitted by Uniroyal Chemical Co., Middlebury, CT. MRID 444649 -56.

Hatzenbeler, C. J. 1997. Soil column leaching study of [ 14 

### C]D2341. Project ID No.: 96-0024. Unpublished study performed by Ricerca, Inc., Painesville, OH; and submitted by Uniroyal Chemical Co., Inc., Middlebury, CT. MRID 444649-55.

Terrestrial Fie ld Dissipation (835.6100) Jablonski, J. E. 1997. Terrestrial field dissipation of D2341 applied to bare ground in North Carolina. Laboratory Study No.: 96-0034. Laboratory Project ID: 6737. Unpublished study performed by American Agricultural Services , Inc., Cary, NC (in- life phase); and Ricerca, Inc., Painesville, OH (analytical phase); and submitted by Uniroyal Chemical Co., Inc., Middlebury,

CT. MRID 444649-57.

Jablonski, J. E. and R. G. Kenyon. 1997. Terrestrial field dissipation of D2341 applied to bare ground in Washington. Laboratory Study No.: 96-0035. Laboratory Project ID: 6739. Unpublished study performed by Qualls Agricultural Labs, Inc., Ephrata, W A (in

- life phase), and Ricerca, Inc., Painesville, OH (analytical phase); and submitted by Uniroyal Chemical Co., Inc., Middlebury, CT. MRID 444649-58.

Jablonski, J. 1998. Terrestrial field dissipation of D2341 applied to bareground in California: Lab

Pro ject No: 6738-96-0033- CR -001:96-003:6738. Unpublished study prepared by Ricerca, Inc.

MRID 45052306.

Jablonski, J. 1999. Stability of D2341 and D1989 and D3598 in soil during freezer storage: Lab Project No: 96-0036:6743-96-0036- CR -001:6743. Unpublished study prepared by Ricerca, Inc.

MRID 45052307.

Jablonski, J. 1999. Analytical method for analysis of D2341, D1989 and D3598 in soil: Lab Project No: 6616-96-0269- CR -001. Unpublished study prepared by Ricerca, Inc. MRID

45052308.

### Page 30 of 32 

### Appendix E

. Chemical Structures

### Page 31 of 32Appendix F. Submitted Ecological Toxicity Data for Bifenazate Degradates D1989, D-3598, and D9472 in Comparison to the Parent Ecological Toxicity Data for D

- 1989

Guideline

# Data Requirement Submitted

Studies

MRID # Study

Classification Ten tative Endpoint (Data not full y reviewed) Parent for Comparison

850-1300 Freshwater

invertebrate

acute EC 50 

### (Daphnia magna) 45141801 In Review EC 50 

### :0.25 mg

/L EC 50 

### : 0.50 mg

a.i./L

Non

guideline Acute 14

- day

Earthworm ( Eisenia fetida) 47622301 Supplemental LC50: 66.7 mg./kg dry soil (Data reviewed

but supplemental) MRID (48929520) is in

review.

Tentative endpoint: LC 50 

### >1250 mg a.i./kg dry soil

Ecological Toxicity Data for D

- 3598

Guideline

# Data Requirement Submitted

Studies

MRID # Study

Classification Te ntative Endpoint (Data not ful ly reviewed) Parent for Comparison

850-1075 Freshwater fish

acute LC 50 

### ( Oncorhynchus mykiss ) 48929504 In review 96 hr LC 50 

### : 0.044 mg /L 96 hr LC 50 

### : 0.78 mg a.i./L

850-1300 Freshwater

invertebrate

acute EC 50 

### (Daphnia magna) 48929503 In review 48 hr EC 50 

### : 0.051 mg/L 48 hour EC 50 

### of 0.50 mg a.i./L

850-4400 Aquatic plant ( Selenastrum capricornutum ) 48929502 In review 96 hr EC 50 

### : 0.78 mg/L (cell density)

NOAEC: 0.38 mg/L 96 hr EC 50 

### : 0.89 mg a.i./L

NOAEC: 0.25 mg a.i./L

Non

guideline Acute 14

- day

Earthworm ( Eisenia fetida) 48929501 In review LC 50 

### : 185.4 mg a.i./kg dry soil MRID (48929520) is in

review.

Tentative endpoint: LC 50 

### >1250 mg a.i./kg dry soil

### Page 32 of 32 Ecological Toxicity Data for D

- 9472

Guideline

# Data Requirement Submitted

Studies

MRID # Study

Classification Ten tative Endpoint (Data not

full y reviewed) Parent for Comparison

850

- 1300 Freshwater

invertebrate

acute EC 50 

### (Daphnia magna) 48929508 In review 48 hr. EC 50 

### : 0.78 mg/L EC 50 

### : 0.50 mg

a.i./L

850

- 4400 Aquatic plant ( Scenedesmus subspicatus ) 48929509 In review 76 hr EC 50 

### : 0.71 mg/L

NOAEC: 0.11 mg/L 96 hr EC 50 

### : 0.89 mg a.i./L ( Selenastrum capricornutum)

850

- 1075 Freshwater fish

acute LC 50 

### ( Lepomis

macrochirus ) 48929506 In review 96 hr EC 50 

### : 0.23 mg/L 96 hr EC 50 

### : 0.58 mg a.i./L