### UNI TED STATES ENVIRONM ENTA L J>RO TECTIO N AGENCY

W ASHJ N GTON D. C., 20460

OFFICE OF CHEMICAL S A FETY
AND POLLUTION PREVENTI ON



### PC Code: 101 103

DP Barcode: 408388 April29, 2013

MEMORANDUM

Subject:



### To:

Through:

From: Registration Review: Preliminary Problem Formulation for Pymetrozine

Steven Snyderman, Chemical Review Manager

Patricia Parrott, Chief

Risk Management and Implementation Branch III

Pesticide Re-evaluat i on Division (7508P)

Dana Spatz, Branch**Chi-~~~~;:,.;;~~­** 

### Melissa Panger, Ph

. D., Semor

Environmental Risk Branch Ill

Environmental Fate and Effects Divi s i on (7507P)

ochelle Bohaty, Ph.D., Chemist

ames Hetrick, Ph.D., Senior Advisor

### ~w

atherine 

## R. Stebbins,**Biologist ~**  

### .,. Rosanna Louie-Juzwiak, RAPL

Environmental Risk Branch Ill

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, pymetrozine (attached). This document is

intended to provide an overview of what is currently known regarding the environmental fate and ecological effects associated with pymetrozine 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 ecologica l risk assessment in support of registration revi ew.



### 1

### 2 

# Introduction

Pymetrozine is a pyridine azomethine insecticide that is currently registered for use on ornamental plants, non-bearing frui t and nut trees in nurseries, Ch ristmas trees, and a variety of agricultural crops. This gr oup of insecticides exhibits a uniqu e mode of action characterized as neural inhibition of feeding behavi or in its target pests (insects in the order Homoptera-includes aphids, whiteflies, and leafhoppers). Details of pymetrozine’s ner vous system action are not fully understood, but it is thought to wo rk by affecting serotonin or th e chordotonal organs in the insect nervous system. 1,2 

### Pymetrozine works primarily by inge stion but also has some contact activity. Pymetrozine has residual activity in the plant and will control pests that move onto the plant after spraying. The chemical structure of py metrozine, as well as the chemical name and other identifiers are provided in Table 1

.

Table 1. Pymetrozine Chemical Identifiers

Parameter Identifier

Chemical Structure HN

N N N N

CH 3 O

Chemical Name (4,5-dihydro-6-methyl-4-[(3-pyridinylmethy lene) amino]-1,2,4-triazine-3(2H)-one) 1,2,4-triazin-3(2H)-one, 4,5-dihydro-6-methyl-4-[(3-pyridinylmethylene) amino]

SMILES O=C1NN=C(C)CN1N=Cc2cccnc2

CAS Number 123312-89-0 Company Code CGA 215944



## Use Characterization

There are two end use products for pymetrozine (Fulfill ® 

### and Endeavor ® 

### ) and both are formulated as water dispersible granules. Foli ar spray applications may be made using ground and aerial equipment (except for non-agricultural uses, and use on hops and tobacco). Additionally, chemigation applications are allo wed for use on potatoes except in the state of California (chemigation applications ar e prohibited for potatoes in CA).

The Fulfill ® 

### label (EPA Reg. No. 100-9112), which has the crop uses, lists the maximum application rates on a seasonal (per crop cycle) rather than annual basis so during the assessment, the number of crop cycles per year will need to be considered. Additionally, the SLN label for use on tomatoes grown for transplant (FL030004) does not provide an application rate (use

1 L. Kaufmann et. al. 2004. The serotonergic system is involved in feeding inhibition by pymetrozine. Comparative studies on a locust (Locusta migrat oria) and an aphid (Myzus persicae.) Comp. Biochem. Physiol. C-Toxicol.

Pharmacol. (138) pp 469–483

2 J. Ausborn et al. 2005. The insecticide pymetrozine selectively affects chordotonal mechanoreceptors J Exp Biol. (208) pp. 4451-4466.

### 3 instructions state to apply 1.5 oz of product per 100,000 plants) in terms of pounds active ingredient per acre (lb a.i./A).

Table 2 provides a summary of the use patterns and maximum use rates for the current uses of pymetrozine. In addition, this table includes the number of crop cycles that may be assumed to occur for each crop that does not specia lly state a yearly application rate.

Agricultural Use Sites Pymetrozine may be applied to various agricultu ral crops including: alfa lfa (under 5 Section 24c registrations), asparagus, cole crops, cotton, cucurbit vegetables, fruiting vegetables, hops, leafy vegetables, pecans, potatoes, root and tuber vegetables, and tobacco.

Pymetrozine is registered for two active Secti on 3 and nine SLN/Section 24c registrations. The SLN registrations are for alfalf a (ID, MT, OR, UT, WA); vegetables grown for seed (arugula, beet, broccoli raab, Brusse ls sprouts, cabbage, carrot, caulif lower, chinese cabbage/kale/mustard, collard greens, endive, kale, kohlrabi, lettuce, mustard, parsley, parsnip, radish (other than daikon), rape, rutabaga, spinach, spinach mustar d, Swiss chard, turnip (WA); root vegetables grown for seed (OR); tomatoes grown for transp lant (FL); and for enhanced management of whiteflies in tomatoes (to allow a gr eater number of applications-FL).

According to the available usage data, the crops w ith the highest use in terms of pounds of active ingredient (a.i.) applied ( 2003-2010 average) are potatoes (a n average of 4,000 pounds a.i. applied annually) followed by cantaloupes, lettuce, pecans, and tomatoes (~ 1,000 pounds a.i. applied annually) 3



### .

Non-Agricultural Use Sites Pymetrozine may be applied to ornamental s grown outdoors (landsca pe ornamentals/ground

covers and field or container grown) and also to ornamental s in greenhouses, lath/shadehouses, and interiorscapes. Other use sites include non- bearing fruit and nut tr ees in nurseries and

Christmas trees.

Limited usage data are available for non-ag ricultural uses. For 2002, 2004, and 2006, (the most recent years for which non-agricultural survey data are available), less than 500 lb. of pymetrozine was reported for nursery/greenhouse uses 4



### .

3 U.S. EPA. 2012. Screening Level Use Analysis-Pymetrozine. June 21, 2012. 4 U.S.EPA. 2013. BEAD Chemical Profile for Registration Review: Pymetrozine (PC Code 101103).4Table 2. Currently Registered Pymetrozine UsesUse SiteApplicationMethodMaximumSingleApplicationRate(lb a.i./A)MaximumNumber ofApplicationsper CropCycleMaximumApplicationRate perCrop Cycle(lb a.i./A)Numberof CropCyclesPer YearaMaximumNumber ofApplicationsper YearMaximumApplicationRate perYear(lb a.i./A) MRI (days) REI (hours) PHI (days)CommentsALFALFA(SLNS for ID,MT, OR, UT,WA)Aerial/Ground0.0859 2b0.1719 1 2c0.1719c7 12 NSPerennial crop with standsliving 3-5 years havingmultiple cuttings per year;however, alfalfa can be grownas part of a crop rotation thatmay results in more than 2pymetrozine applications peryear.ASPARAGUSAerial/Ground0.0859 6b0.5156 1 6c0.5156c30 12 NSOne crop per year, harvestedevery 1 to 3 days over a 3 to 4week period. Once established,asparagus field remain inproduction for 8-10 years.CHRISTMASTREESGroundspray/Containerizedplant0.3125 NS NS 1Outdoor:5dIndoor:10dOutdoor: 1.5Indoor:3.1257 12 NSFor CA, do not exceed 1.5 lba.i /A/year for indoor usesCOLE CROPSAerial/Ground0.0859 2b0.1719 3 6b0.5157 7 12 NSCOTTONAerial/Ground0.0859 2b0.1719 1 2c0.1719 7 12 NSAlfalfa can be grown as part ofa crop rotation that may resultsin more than 2 pymetrozineapplications per year.CUCURBITVEGETABLESAerial/Ground0.0859 2b0.1719 1 2c0.1719 7 12 NSCucurbits can be grown as partof a crop rotation that mayresults in more than 2pymetrozine applications peryear.FRUITINGVEGETABLESAerial/Ground0.0859 2b0.1719 1 2c0.1719 7 12 NSFruiting vegetables such aspeppers, tomatoes, etc. can begrown as part of a croprotation that may results inmore than 2 pymetrozineapplications per year.5FRUITS(Nonbearingfruit and nuttrees innurseries)Groundspray/Containerizedplant0.3125 NS NS 1Outdoor:5dIndoor:10dOutdoor: 1.5Indoor:3.1257 12 NSHOPS Ground 0.1875 3 0.5625 NS NS 14 12 NSLEAFYVEGETABLESAerial/Ground0.0859 2b0.1719 2 4c0.3438 7 12 NSUp to 2 crop cycles per yearin rotation with other crops ispossible in some locations;therefore, more than 4applications of pymetrozineare possible.ORNAMENTALSGroundspray/Containerizedplant0.3125 NS NS 1Outdoor:5dIndoor:10dOutdoor: 1.5Indoor:3.1257 12 NSPECANAerial/Ground0.125 2b0.25 1 2c0.25 7 12 NSPOTATO,WHITE/IRISHAerial/Ground/Chemigation0.1719 2b0.3438 1 2c0.3438 7 12 NSChemigation applications areprohibited in CA.Potatoes can be grown as partof a crop rotation that mayresults in more than 2pymetrozine applications peryear.ROOT ANDTUBERVEGETABLES(IncludesOregon SLN)Aerial/Ground0.1719 2b0.3438 1 2c0.3438 7 12 NSRoot and tuber vegetables canbe grown as part of a croprotation that may results inmore than 2 pymetrozineapplications per year.TOBACCO Ground 0.0859 2b0.1719 1 2c0.1719 7 12 NSTobacco can be grown as partof a crop rotation that mayresults in more than 2pymetrozine applications peryear.TOMATO -SLN (FL) forenhancedmanagement-4apps)Aerial/Ground0.043 4 0.1719 1 NS NS 14 12 NSTomato can be grown as partof a crop rotation that mayresults in more than 4pymetrozine applications peryear.6TOMATO -SLN (FL) fortomatoes grownfor transplantAerial/Ground1.5 ozproductper100,000plants2 0.013f1 2c0.013c7 12 NSLabel says two more apps of2.75 oz product/A (0.0859 lba.i./A-the rate on parent label)may be used in the field.Note: because the specific useis for tomatoes grown fortransplant, the applicationswill not be applied to the samefield so 4 applications arepermitted to the plant but only2 applications to the same plotof land. Tomato can be grownas part of a crop rotation ormulti-crops per year; therefore,more than 2 pymetrozineapplications per year may bepossible to one plot of land.VEGETABLESgrown for seedSLN label(WA)Aerial/Ground0.0859 2b0.1719 3 6c0.5157 7 12 NSa.The number of crop cycles per year was derived from the “Maximum Number of Crop Cyclesper Year in California for Methomyl UseSites” memo.5b.Not specified on the label; however, assumed the maximum application rate per crop cycle divided by the maximum single application rate.c.Not specified on the label; however, assumed the maximum number of applications per crop cycle multiplied by the number of cropcycles possible per year.d.Not specified on the label; however, assumed the maximum single application rate divided by the maximum yearly application rate.e.0.75 oz a.i.(50% by weight)/100,000plants*1.36 g/0.034 oz*1lb/453.6=6.6 x 10-7lb a.i./plant; 6.6 x 10-7lb a.i./plant *10,890 plants/acre6= 6.6 x10-3lb a.i./Af.Calculated based on 2 applications per crop cycleNot specified (NS) on the label5 U.S. Environmental Protection Agency, M. Kaul,Maximum Number of Crop Cycles Per Year in California for Methomyl Use Sites,February 28, 2007.6 U.S. Environmental Protection Agency, Becker, J., Ratnayake, S.Acres Planted per Day and Seeding Rates of Crops Grown in the United States,March 24, 2011.

### 7 

## Conclusions from Previous Risk Assessments

Ecological Risk Assessments

EPA has conducted multiple ecological risk assessments for pymetrozine and these assessments will serve as a basis for this problem formulation document, as well as for the risk assessment to be conducted as part of the registration review . Pymetrozine was first assessed as a new active ingredient in 1999. Two new use assessments were conducted in 2000 and 2001, one for use on cotton, pecans, leafy vegetables , and brassica (08/00), and anot her for hops and cotton (05/01). In 2004, a new use assessment was conducted for use on asparagus (05/04) and this assessment included both the parent, pymetrozine, and the environmental degradate CGA-359009. The most recent assessment was conducted in 2006 (07/06) to assess a rate increase for potatoes and other tuberous root and corm vegetables. The 2004 aspa ragus assessment was the only one to include the parent and degradate (CGA359009) in the estimated exposures.

All of the previous assessments up until 2006 stat ed that there were no risks of concern to aquatic or terrestrial organisms from the pr oposed pymetrozine uses. However, the latest assessment conducted in 2006 (to assess a rate increase for potatoes/tuberous and corm vegetables) reported a risk to mammals on a chronic exposure basi s (RQs ranged from 0.02-2.41) and also noted that due to a differenc e in the foliar dissi pation half- life that was used in some of the previous assessmen ts (35 days in 2006 vs. 5.5 days in earlier assessments), there would have also been LOC exceedances in the previous assessments, had the 35-day half-life value been used. Table 3 provides a summary of the major ecological conclusions presented in the previous risk assessments.

Drinking Water Exposure Assessments

A drinking water assessment (DWA) for pymetro zine was conducted at the time of the new

chemical assessment 7 

### , and updated with each subsequent new use. Exposure estimates from these assessments are highlighted in Table 4 and Table 5 . A DWA will be conducted to support future pymetrozine human health dietary risk assessments. The DWA will incorporate model estimates of pymetrozine, as well as any tran sformation products identif ied as residues of concern in surface water and/or groundwater. Con centrations of pymetrozine residues in drinking water will be estimated using EFED aquatic models ( e.g. , PRZM-EXAMS, SCI-GROW and PRZM-GW). The major degradate, CGA359009 is curre ntly considered a re sidue of concern in drinking water 8 

### ; however, if any additional environmental transformation products of pymetrozine are identified as a potential toxicologi cal concern with similar toxicity as the parent, all residues will be considered using a total to xic residue (TTR) approach for the drinking water

assessment.

7 U.S. Environmental Protection Agency, Nguyen, T. L., Carey, S. EFED New Chemical Environmental Risk Assessment for Pymetrozine , DP250387, April 21, 1999. 8 U.S. Environmental Protection Ag ency, Drew, W. T., Hurley, P. Pymetrozine on Asparagus. Health Effects Division (HED) Metabolism Assessment Re view Committee (MARC) Decision Document . DP 292533, October 23,

20048Table 3. Summary of Risk Concerns Identifiedfor Pymetrozine in Previous AssessmentsExposureBasisBirdsMammalsTerrestrialPlantsTerrestrialInverts.(honey beehazard)FishAquaticInvertsAquaticPlantsGroundwaterContaminationPersistenceTransformationProducts ofConcernAcute ----* -- -- -- ---- --Chronic --* -- -- -- --* Uncertain due to data gapsTable 4. Summary of Prior Drinking Water Assessments for Pymetrozine in Surface WaterAssessment/DateCropScenarioModel UsedPymetrozinePymetrozine and CGA 359009 (TTR Approach)1-in-10 YearPeakConcentrationμg/L (ppb)1-in-10 YearAnnualAverageConcentrationμg/L (ppb)30 YearAverageYearlyConcentrationμg/L (ppb)1-in-10 YearPeakConcentrationμg/L (ppb)1-in-10 YearAnnualAverageConcentrationμg/L (ppb)30 YearAverageYearlyConcentrationμg/L (ppb)EmergencyExemptionDP244341andDP2443423/98WI PotatoaGENEEC 2.05 1.12bEmergencyExemptionDP2576557/99CALettucePRZM/EXAMS 2.13 1.1c0.422EmergencyExemptionDP2669027/00GAPecansGENEEC 4.0 2.3bRevisedAssessmentDP2751236/01HopsFIRST13.6 2.7dCotton 1.2 0.24d9RefinedAssessmentD27512311/01CottonPRZMEXAMS0.73 0.2dCucurbit 3.1 0.7dTomato 3.7 0.8dCabbage 4.4 0.9dPecan 5.2 1.6dHops 2.7 1.1dNew UseAssessmentDP28393710/04AsparagusePRZM-EXAMS9.0 4.2 2.5 16.3 10.1 6.0New UseAssessmentDP3216757/06PotatoesPRZM-EXAMS7.1 1.8 1.4a.0.086 lb a.i./A; 2 applications; 7 day application intervalb.56-day average concentrationc.60-day average concentrationd.Annual averagee.The maximum single application rate (Maximumsingle application rate 0.172 lb a.i./A;Maximum application rate per season 0.516lb a.i./A)assessed is higher than the maximum single application rate currently registered for asparagus (Maximum single application rate0.0859 lb a.i./A;Maximum application rate per season 0.516 lb a.i./A).

### 10 Table 5. Summary of Prior Drinking Water A ssessments for Pymetrozine in Groundwater

Assessment Crop Model

Used 

### Pymetrozine Pymetrozine and CGA 359009 (TTR Approach)

Peak
Concentration

μ g/L (ppb) Yearly Mean
Concentration

μ g/L (ppb) Peak
Concentration

μ g/L (ppb) Yearly Mean
Concentration

μ g/L (ppb) Emergency Exemption
DP244341 and

D244342

3/98 WI Potato SCIGROW 0.019 0.019

Emergency Exemption

DP257655
7/99 CA

Lettuce SCIGROW 0.015 0.015

Emergency Exemption

DP266902

7/00 GA

Pecans SCIGROW 0.015 0.015

New Use

Assessment
DP283937

10/04 Asparagus e SCIGROW 0.016 0.016 0.038 0.038



### Clean Water Act Programs

Pymetrozine is not identified as a cause of im pairment for any water bodies listed as impaired under section 303(d) of the Clean Water Act. No Total Maximum Daily Load (TMDL) criteria have been developed for pymetrozine. Aquatic Life Ambient Water Quality Criteria documents or Aquatic life benchmarks have not been published for pymetrozine.



# Environmental Fate and Transport

Parent Pymetrozine

Physical and Chemical Properties

The physicochemical properties of pymetrozine are shown in Table 6 . Based on these properties alone, pymetrozine is not expected to be volatile or to bioaccumulate. It is highly soluble in

water.

### 11 Table 6. Selected Physical/Chemical Parameters of Pymetrozine

Parameter Value Source/Classification

Molecular Mass (molecular formula) 217.23 g/mol (C 10 H 11 N 5 O 6 ) EPISuite v4.0

Vapor Pressure 5.0 x 10 -6 Pa; 3.0 x 10 -8 mmHg (25 °C) MRIDs 44024901
44024904 Acceptable

Henry’s Law Constant <3.0 x 10 -6 Pa m 3 /mol

Aqueous Solubility 290 mg/L (25 °C; pH 6.5) MRIDs 44024901
44024904 Acceptable

pK

a pk a1 = 4.06 (basic) pk a2 <1 (basic) MRIDs 44024901
44024904 Acceptable

Log octanol-to-water partition coefficient (log K OW ) -0.18 (pH ?) MRIDs 44024901
44024904 Acceptable

MRIDs 44024901 and 44024904 provide pymetrozine solubility data for a number of common solvents.



### Environmental Fate Properties

Environmental fate properties of pymetrozine are summarized in Table 7 . These half-life values presented in the table have been updated from previous assessments to reflect the NAFTA degradation kinetics guidance 9 

### for characterization purposes and will be used to calculate model input values. Updated model input values wi ll be calculated based on current model input guidance for each respective exposure model at the time the assessment is completed. The kinetic analyses are presented in APPENDIX A

.

Table 7. Environmental Fate Parameters of Pymetrozine

Parameter Value Source Classification; Comments

Abiotic Transformation Mechanisms

Hydrolysis half-life

at 25  C 12.1 days pH 5 MRID 44024962 (triazine ring labeled) supplemental

28.4 days pH 5 >> 30 days pH 7 >> 30 days pH 9 MRID 44024963 Supplemental (triazine ring-labeled)

.

9 Guidance for Evaluating and Calculating Degradation Kinetics in Environmental Media , Health Canada, U.S.
Environmental Protection Agency, December 2012.

### 12 Parameter Value Source Classification; Comments

14.4 days pH 5 >> 30 days pH 7 >> 30 days pH 9 MRID 44024964 Supplemental (pyridine ring-labeled) Draft DER;

MRID 44024963

Soil photolysis half-life

at 24  C 13.6 d (DFOP t slow; equivalent time at 40 °N; dark control adjusted value) MRID 44411324 Supplemental (pyridine ring-labeled)

26.8 d (DFOP t slow; equivalent time at 40 °N; dark control adjusted value) MRID 44411325 Supplemental (triazine ring-labeled) A large amount of unextracted residues (>75%) was observed in the irradiated samples compared to the dark control (<20%) at study termination.

20.2 d MRID 44411324 and MRID 44411325 (average of the two labels)

Aqueous photolysis

half-life at 25  C 3.0 d (equivalent time at 40 °N) MRID 44411321 Supplemental (pyridine ring-labeled)

2.0 days (equivalent time at 40 °N) MRID 44471702 Supplemental (triazine ring-labeled) A major degradate (23.4% AR) was not
identified.

2.7 days (equivalent time at 40 °N) MRID 44411321 and MRID 44471702 (combined labels; studies were conducted under the same conditions)

2.0 days (reasonably re presentative of 40 °N ) b MRID 44411322 Supplemental (triazine ring-labeled) A major degradate (28.9% AR) was not

identified.

Biotic Transformation Mechanisms c

Aerobic soil

metabolism half-life at

25 °C DFOP DT50= 159 d; DT90= 838 d;
DFOP Slow t 1/2 = 292 (low dose, sandy loam)

DFOP DT50= 191 d; DT90= 824 d;

DFOP Slow t 1/2 = 381 (high dose, sandy loam) MRID 44024965 Supplemental (pyridine ring-labeled) Only was soil (at a high and low dose)

was used to assess the transformation of pymetrozine. Application rates used in this study is much higher than the maximum single application rate.

96 days (low dose), 116 days (high dose) MRID 44024966 Supplemental (triazine ring-labeled) Only was soil (at a high and low dose)
was used to assess the transformation of pymetrozine. Application rates used in this study is much higher than the maximum single application rate.

Anaerobic Soil

Metabolism Half-life No data

### 13 Parameter Value Source Classification; Comments

Aerobic Aquatic

Metabolism Half-life No data

Anaerobic Aquatic

Metabolism Half-life

half-life at 25 °C SFO t 1/2 = 73.7 d; DT90= 245 d (low does; total system)

SFO t 1/2 = 83.2 d; DT90= 276 d (high does; total system) MRID 44024967 Supplemental (pyridine ring-labeled)
Formation/decline of several transformation products was not

established.

DFOP DT50= 78.5 d; DT90= 310 d;
DFOP Slow t 1/2 = 99.9 (low dose, total system)

IORE DT50= 91.1 d; DT90= 363 d;

tR IORE = 109 d (high dose, total system) MRID 44024968 Supplemental (triazine ring-labeled)

Formation/decline of several transformation products was not

established.

Mobility Range of Freundlich soil-water partition coefficients (K F ); exponent (1/n) values;

andorganic carbonnormalized coefficients (K FOC ) 1/n <<1 1789, 7875, 15708, 4420, 2306 MRID 44024969 (acceptable)

Field Dissipation

Terrestrial Field Dissipation Half-life Bareground Plot (748 g ai/A)

GA- (50WP)- t 1/2 = 137 days ; DT50<3 days

CGA-18077 (niacin) was detected 0-18 inch depth

Parent, CGA-23199, CGA-359009, CGA-23199 were not

detected below 0- 6inch depth

Cotton Plot (748 g ai/A)

GA- (50WP)- t 1/2 = 122 days ; DT50 -7 and 21 days

CGA-18077 (niacin) was detected 0-18 inch depth

CGA-23199 was detected 0-12 inch depth

Parent, and CGA-359009 were not detected below 0-

6inch depth MRID 44647901, 44411334, 44471703, 44647904, 44411338, 44647903 (supplemental)

Analytical methods were inadequate for detecting CGA-249257, storage stability for the CGA-180777, CGA-249257, and CGA-359009 were inadequate,

Bareground Plot (748 g ai/A)

NY- (50WP)- t 1/2 = 22 days ; DT50~3 days

Parent was not detected below 0-6 inch depth

CGA-249257 was detected 0-12 inch depth

CGA-180777 was detected 0-18 inch depth

CGA 294849 was detected 0-12 inch depth CGA -23199 was detected 0- 6 inch depth MRID 44411334 (supplemental)

44647902 & 44647901 Analytical methods were inadequate for detecting CGA-249257, storage stability for the CGA-180777, CGA-249257, and CGA-359009 were inadequate,

### 14 Parameter Value Source Classification; Comments Bareground Plot (748 g ai/A)

CA- (50WP)- t 1/2 = 120 days

No residues were not det ected below 0- 6inch depth

Tomato Plot (748 g ai/A)

GA- (50WP)- t 1/2 = 76 days

No residues were not det ected below 0- 6inch depth MRID 44411338, 44647903 (supplemental) Analytical methods were inadequate for detecting CGA-249257, storage stability
for the CGA-294849 and GS-23199 were inadequate

Bioaccumulation

Fish BCF edible, non-edible, and
whole fish tissues No data Pymetrozine is not expected to bioaccumulate based on the calculated log

K

ow (-0.18).

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

b. This value is based on a 12 hour per day exposure at an average daily intensity of approximately 410

W/m 2 . No conversion factor was used to adjust to an environmentally relevant half-life. Based on the National Center for Atmospheric Research (NCAR) /National Center for Environmental Prediction (NCEP) data for June 21 (years 1948-2011) the averag e surface radiation at 40 °N ranges between 98-422

W/m 2 . Therefore, it is reasonable that 410 W/m 2 represents a sunny day at 40 °N.

c. Representative half-life values were calculated using the draft NAFTA degradation kinetics document: Guidance for Evaluating and Calculating Degradation Kinetics in Environmental Media (draft document June 29, 2011); Single First Order (SFO), Nth-Order Rate Model or Indeterminate Order Rate Equation Model (IORE), and Double First-Order in Parallel (DFOP) Applied Radioactivity (AR)
BCF: bioconcentration factor



### The major route of dissipation are expected to be controlled by acid cata lyzed abiotic hydrolysis, photodegradation in water and on soil, microbial me diated degradation in soil, and transport in

runoff or on eroded sediment/soil. The low Henr y's Law Constant value coupled with relatively high soil:water partitioning coefficient indicates that pymetrozine volatilization from soil is insignificant. The low octanol:water partition co efficient suggests that pymetrozine does not

bioaccumulate.



## Transformation Products

Fifteen degradates were observed in the pymetrozi ne laboratory studies: nine were identified and six were unknowns. The major transformation produc ts, as well as a few minor degradates are

listed in Table 8 with the maximum amounts of each chemi cal formed in the various studies.15Table 8. Pymetrozine Environmental Transformation ProductsCode Name/SynonymChemical Name/SMILESChemical StructureStudy Type/ConditionsRef.MRIDMaximumPercentAppliedRadioActivityPercentAppliedRadioActivity atStudyTerminationMAJORCGA 2155254-amino-6-methyl4,5-dihydro-2H-(1,2,4)-triazin-3-oneC1(NN=C(CN1N)C)=OHNNNCH3ONH2HydrolysispH 5 at 25 °C44024963(triazineringlabeled)47.8 (32 DAT) 47.8 (32 DAT)AquaticPhotolysispH 7 at 25 °C44471702(triazineringlabeled)46.2 (3 DAT) 46.2 (3 DAT)44411322(triazineringlabeled)66.0(14 DAT) 51.0 (30 DAT)Aerobic SoilMetabolismsandy loam44024966(triazineringlabeled)7.0 (92 DAT) 1.0 (357 DAT)AnaerobicAquaticMetabolism44024968(triazineringlabeled)7.2 (58 DAT) 7.2 (58 DAT)CGA 300407CAS Number: 500-22-13-pyrideinecarboxaldehydeC1=CC(=CN=C1)C=ONOHydrolysispH 5 at 25 °C44024964(pyridineringlabeled)63.0 (30 DAT) 63.0 (30 DAT)Soil PhotolysisSilt loampH 7.32.3% OC44411324(pyridineringlabeled)6.13 (34 DAT)Irradiated8.96 (15 DAT)Dark Control6.13 (34 DAT)Irradiated7.04 (34 DAT)Dark Control16Code Name/SynonymChemical Name/SMILESChemical StructureStudy Type/ConditionsRef.MRIDMaximumPercentAppliedRadioActivityPercentAppliedRadioActivity atStudyTerminationAquaticPhotolysispH 7 at 25 °C44411321(pyridineringlabeled)93.1(33 DAT)Irradiated6.6 (30 DAT)Dark Control93.1 (33 DAT)Irradiated6.6 (30 DAT)Dark ControlCGA 35900094,5-dihydro-5-hydroxy-6-methyl-4-[(3-pyridinylmethylene)amino-1,2,4-triazine-3-(2H)-oneC1(NN=C(C(N1N=CC2=CN=CC=C2)O)C)=OHNNNNNCH3OOHSoil PhotolysisSilt loampH 7.32.3% OC44411324(pyridineringlabeled)28.9 (3 DAT)Irradiated47.48 (15DAT)Dark Control9.34 (34 DAT)Irradiated46.73 (34 DAT)Dark Control44411325(triazineringlabeled)34.22(3 DAT)Irradiated57.17 (15DAT)Dark Control7.93 (32 DAT)Irradiated5.94 (34 DAT)Dark ControlAnaerobicAquaticMetabolism44024968(triazineringlabeled)1.6 (7 DAT)total system0.1 (176 DAT)total systemCGA 180777CAS Number: 59-67-6Niacinnicotinic acidPyridine-3-carboxylicacidC1=CC(=CN=C1)C(O)=ONOOHAquaticPhotolysispH 7 at 25 °C44411321(pyridineringlabeled)5.3 (33 DAT) 5.3 (33 DAT)Aerobic SoilMetabolismsandy loam44024965(pyridineringlabeled)16.7 (58 DAT) 0.2 (357DAT)AnaerobicAquaticMetabolism44024967(pyridineringlabeled)85.0(357 DAT)total system85.0 (357 DAT)total system17Code Name/SynonymChemical Name/SMILESChemical StructureStudy Type/ConditionsRef.MRIDMaximumPercentAppliedRadioActivityPercentAppliedRadioActivity atStudyTerminationGS 231996-Methyl-2H-[1,2,4]triazine-3,5-dioneC1(NC(C(=NN1)C)=O)=OHNNNHCH3OOAnaerobicAquaticMetabolism44024968(triazineringlabeled)15.8 (357 DAT)total system15.8 (357 DAT)total systemAerobic SoilMetabolismsandy loam44024966(triazineringlabeled)0.9(30 DAT) 14.8(357 DAT)CGA 2492576-Methyl-4,5-dihydro-2H-[1,2,4]triazin-3-oneC1(NCC(=NN1)C)=OHNNNHCH3OAerobic SoilMetabolismsandy loam44024966(triazineringlabeled)0.2 (30 DAT) 0.7 (357 DAT)AnaerobicAquaticMetabolism44024968(triazineringlabeled)14.1 (357 DAT)total system14.1 (357 DAT)total systemMINORCGA 2948494-amino-6-methyl1,2,4-triazine3,5(2H,4H)-dioneHNNNCH3OONH2Soil PhotolysisSilt loampH 7.32.3% OC44411325(triazineringlabeled)5.35 (16 DAT)Irradiated5.94(32 DAT)Dark Control3.81 (DAT)Irradiated5.94 (32 DAT)Dark ControlAerobic SoilMetabolismsandy loam44024966(triazineringlabeled)2.5 (30 DAT)12.0 (357 DAT)AnaerobicAquaticMetabolism44024968(triazineringlabeled)2.3 (273 DAT) 1.4 (357 DAT)18Code Name/SynonymChemical Name/SMILESChemical StructureStudy Type/ConditionsRef.MRIDMaximumPercentAppliedRadioActivityPercentAppliedRadioActivity atStudyTerminationCGA 3192516-Oxo-1,6-dihydropyridine-3-carboxylicacidNHOOHOAerobic SoilMetabolismsandy loam44024965(pyridineringlabeled)0.2 (58 and 182DAT)0.1 (357 DAT)CGA 3131246-Hydroxymethyl-4-[(pyridin-3-ylmethylene)-amino]-4,5-dihydro-2H-[1,2,4]triazin-3-oneHNNNNNH2COOHAnaerobicAquaticMetabolism44024968(triazineringlabeled)0.5 (357 DAT) 0.5 (357 DAT)Unknown VIAerobic SoilMetabolismsandy loam44024965(pyridineringlabeled)6.1 (7 DAT) 2.8 (357 DAT)2UAerobic SoilMetabolismsandy loam44024966(triazineringlabeled)0.8 (30 DAT)5.0 (357 DAT)Boldfont indicates the highest percentage observed for a given transformation product.MW: molecular weightAR: Applied radioactivityn.d. not detected <LOD

### 19 Mobility data have been provided for some of the identified pymetrozine transformation products. Select physical chemical properties of the major pymetrozine transformation products are provided in Table 9 . Among the reported pymetrozine tr ansformation products reported, CGA359009, GS23199, CW49257 and CGA180777 were de tected in the field studies and showed some mobility.

Table 9. Selected Physical/Chemical Para meters of Pymetrozine Environmental
Transformation Products a



### Parameter Major Transformation Product

CGA

215525 CGA
300407 CGA
359009 CGA
180777 GS 23199 CGA 249257

Molecular Weight (g/mol) 128.13 107.11 233.23 123.11 127.1 113.12

Molecular Formula C 4 H 8 N 4 O C 6 H 5 NO C 10 H 11 N 5 O

2 C 6 H 5 NO 2 C 4 H 5 N 3 O 2 C 4 H 7 N 3 O

Vapor Pressure (mm Hg) 2.1 x 10 -5 0.568 3.1 x 10 -11 9.4 x 10 -5 3.2 x 10 -8 2.2 x 10 -4

Henry’s Constant (atm-m 3 /mol) 3.2 x 10 -12 1.8 x 10 -8 2.6 x 10 -16 1.4 x 10 -10 2.5 x 10 -9 1.1 x 10 -8

Solubility (mg/L) 79780 62860 101900 48150 4777 2931

Log Kow -1.45 0.29 -0.65 0.36 -0.12 0.29

Range of Freundlich soil-water partition coefficients (K F ); exponent (1/n) values; and organic carbon-normalized coefficients (K FOC ) ND

MRID

44411331 ND

MRID

44411328 K f -1.4-3.3

1/n- 0.74-.86

K FOC - 320

MRID

44411326 K f -<0.04-0.3

1/n- 0.89-
0.99

K FOC -19

MRID

44411327 K f -<1.0

1/n- 0.8-0.94

K FOC - 168

MRID
44411329 K f -0.07-.2

1/n- 0.53-0.83

MRID

44411330
Soil Column Leaching

a. Estimated using EPISuite v. 4
b. ND- No data due to instability during equilibration



# Receptors

Table 10 and Table 11 provide a summary of the aquati c and terrestrial taxonomic groups, respectively, and the most sensitive surrogate sp ecies tested to characterize the potential acute and chronic ecological effects of pymetrozine. In addition, the tables provide a preliminary overview of the potential acute toxicity of pymetrozine by pr oviding the acute toxicity

classifications.

### 20 Table 10. Summary of the Most Sensitive Endp oints from Aquatic Toxicity Studies for Pymetrozine

Taxonomic

Group Study Type Surrogate Species

and
Test Material Toxicity Value (all units in terms
of measured active ingredient) MRID and
Classification Acute Toxicity
Classification

Freshwater fish a Acute Rainbow Trout ( Oncorhynchus mykiss )

TGAI LC 50 > 128 mg a.i./L

No mortality or

sublethal effects reported. 44024913 Acceptable Practically

non-toxic

Chronic (Early

Life Stage) Rainbow Trout ( Oncorhynchus mykiss )

TGAI NOAEC 11.7 mg
a.i./L LOAEC > 11.7 mg
a.i./L

No mortality or

sublethal effects reported. 44024918 Supplemental b --

Estuarine/Marine

fish Acute Sheepshead Minnow ( Cyprinodon variegatus )

TGAI LC 50 > 117 mg a.i./L

No mortality or

sublethal effects reported. 44024916 Acceptable Practically

non-toxic

Chronic No Data

Freshwater

invertebrates Acute Water Flea ( Daphnia magna )

TGAI EC 50 = 87 mg a.i./L NOAEC= <19.2 mg
a.i./L Sublethal signs of toxicity (less active than controls) were reported at all test
concentrations. 44024914 Acceptable Slightly toxic

Chronic Water Flea ( Daphnia magna )

TGAI NOAEC = 0.025 mg a.i./L LOAEC = 0.052 mg
a.i./L

Most sensitive endpoint: Reproduction and growth 44024919 Acceptable --

### 21 Estuarine/Marine

invertebrates Acute Eastern Oyster ( Crassostrea virginicia )

TGAI LC 50 = 3.05 mg
a.i./L NOAEC = 0.768 mg
a.i./L

No sublethal effects

were observed 44024917 Acceptable Moderately

toxic

Chronic No Data

Aquatic plants and algae Nonvascular Green algae ( Pseudokirchneriella subcapitata )

TGAI EC 50= 17 mg a.i./L NOAEC = 6.28 mg
a.i./L based on a

reduction in cell density 44024959 Acceptable --

Vascular Duckweed ( Lemna gibba )

TGAI EC 50 >109 mg a.i./L NOAEC = 49 mg
a.i./L based on a

reduction in frond

number 44024960 Supplemental c --

a. Freshwater fish represent surrogat es for aquatic-phase amphibians.

b. Classified as supplemental because the solvent concen tration used exceeded the guideline recommendations and the highest tested concentration (only up to 13 mg a.i./L) was not high enough to produce adverse effects. However, this study is considered accep table for quantitative use because 13 mg a.i./L is much higher than the expected environmental concentrations.

c. Classified as supplemental because the test material wa s unstable in solution as th e treatment solutions did not

contain detectable amounts at test termination. The EC 50 is based on the initial measured concentration rather than the mean. As a result, the toxicity may be underestimated, however, given that the EECs from previous assessments were well below the NOAEC (the RQ would be 0.001), these supplemental data are acceptable for

use in risk assessment.

### 22 Table 11. Summary of the Most Sensitive Endp oints from Terrestrial Toxicity Studies for Pymetrozine

Taxonomic

Group Study Type Surrogate Species

and
Test Material Toxicity Value (all units in terms of

measured active ingredient) MRID and
Classification Acute Toxicity
Classification

Birds a Acute Bobwhite quail ( Colinus virginianus )

TGAI LD 50 >2000 mg/kg-bw No mortality reported.

Sublethal effects (subdued behavior,

unsteadiness and prostrate posture) were
noted in all three

treatment levels-effects subside by the beginning of day 3. The resultingNOAEC is <500 mg/kgbw based on sublethal

effects. 44024908 Acceptable Practically

non-toxic

Sub-acute dietary Mallard ( Anas platyrhynchos )

TGAI LC 50 >5010 mg/kg diet No mortality reported. NOAEC=311 mg a.i./kg

diet based on reduced body weight gain at the 650, 1300, 2600, and 5200 mg/kg diet dose
levels. 440224910 Acceptable Practically

non-toxic

Chronic Bobwhite quail ( Colinus virginianus )

TGAI NOAEC = 100 mg a.i./kg LOAEC = 300 mg a.i./kg based on number of 14-day old survivors of eggs set 44024911 Acceptable --

Mammals Acute Oral Laboratory rat ( Rattus norvegicus ) LD 50 = 5955 mg a.i./kgbw 44024926 Acceptable Practically

non-toxic

Acute
Inhalation Laboratory rat ( Rattus norvegicus ) LC 50 = 1.8 mg a.i./L 44024930 Acceptable --

Chronic Laboratory rat ( Rattus norvegicus ) NOAEC = 200 mg a.i./kg diet (NOAEL= 13.9 mg/kg-bw/day)

LOAEC = 2000 mg a.i./kg based on reduced body weight in offspring.

No effects on reproduction. 44024950 Acceptable --

### 23 Taxonomic

Group Study Type Surrogate Species

and
Test Material Toxicity Value (all units in terms of

measured active ingredient) MRID and
Classification Acute Toxicity
Classification

Insects Acute

contact Honey bee ( Apis mellifera L. )

TGAI LD 50 >200 μg a.i./bee NOAEL= 200 μg
a.i./bee
No sublethal effects.

44024961 Acceptable Practically

non-toxic

Acute Oral Honey bee ( Apis mellifera L. )

TGAI LD 50 >117 μg a.i./bee

NOAEC= Not
determined. Signs of toxicity noted at all exposure levels

included uncoordinated movements, and lying on

sides and backs. These signs were noted within 1 hour of dosing but were absent by 24 hours. Practically

non-toxic

a. Birds represent surrogates for terrestrial-phase amphibians and reptiles.



## Ecological Effects Characterization

On an acute exposure basis, pymetrozine is cla ssified as “practically non-toxic” to freshwater and estuarine/marine fish, “sligh tly toxic” to freshwater invertebrates, and “moderately toxic” to

estuarine/marine invertebrates. On a chronic exposure basis, based on a supplemental study for freshwater fish (rainbow trout- Oncorhynchus mykiss ), there were no eff ects reported up through the highest test concentration, resulting in a NOAEC of 11.7 mg a.i./L. For freshwater invertebrates, a study with the water flea ( Daphnia magna ), resulted in a NOAEC of 0.025 mg a.i./L based on reduced reproducti on and growth (compared to the control). Chronic toxicity

data are not available for estuarin e/marine fish or inve rtebrates. For vascular aquatic plants, the

EC 50 

### for duckweed ( Lemna gibba) is >109 mg a.i./L with a NOAE C of 49 mg a.i./L (there was
41% inhibition in frond number at the highest dose of 109 mg a. i./L). For non-vascular plants,

the EC 50 

### is 17 mg a.i./L for green algae ( Pseudokirchneriella subcapitata ) with a NOAEC of 6.28 mg a.i./L based on reduced cell density. In previous assessments, there were no LOC exceedances/risk concerns for aquatic animals a nd plants from acute or chronic exposure to pymetrozine.

Based on the available data, pymetrozine is classi fied as “practically non -toxic” to birds on an acute and subacute exposure basis; however, ther e is uncertainty with this classification because acceptable data are only available for one species in the acute oral study and in the dietary study, there was reduced body weight gain at the 650, 1300, 2600, and 5200 mg/kg diet dose levels. On a chronic exposure basis, the NOAEC for the bobwhite quail is 100 mg a.i./kg diet, based on a reduction in the number of 14-day survivors of eggs set. For mammals, pymetrozine is classified as “practically non-toxic” on an acute exposure ba sis. On a chronic exposure basis, the NOAEC

for the rat ( Rattus norvegicus ) is 200 mg a.i./kg diet ( NOAEL= 13.9 mg/kg-bw/day) based on reduced body weight in offspring. Based on the available data for the honey bee ( Apis mellifera

L. ), pymetrozine is classified as “practically non-toxic” with LD 50 

### values of >117 and >200 μg a.i./bee, for acute oral and contact, respectively, however, there is uncertainty with the available

### 24 data (see discussion in Data Gaps). Toxicity data are not available for terrestrial plants. Based on available data in previous assessments, risk s were only identified for mammals on a chronic exposure basis.

Based on the available acute or al study (MRID 44024961), there were several signs of toxicity (including uncoordinated movements and bees ly ing on their sides and backs) noted at all exposure levels suggesting that the mode of action may exte nd beyond inhibition of feeding

behavior. A more recent acute oral/contact st udy (MRID 45579702) is available and while it has not been fully reviewed at this time, a preliminar y review of the data shows that when bees were exposed (oral) and observed for a longer duration (6 hours and 96 hours, respectively), that while mortality was low (a similar observation to the earl ier study), bees at the th ree highest treatments (1.01, 8.77, and 62.71 μg a.i./bee) exhibited sublethal effects ( e.g., bees showing symptoms of paralysis/restricted movement of legs) at 24 hour s after treatment in 90% of the bees, and by the end of the study the bees were only partially r ecovered with 57.5%, 30%, and 10% healthy in the 1.0, 8.77, and 62.7 μg a.i./bee treatments, respectivel y. In this same study, a significant reduction in feeding was also observed at the 0.12, 1.01, 8.77, and 62.71 μg a.i./bee treatment levels when compared to the control (MRID 45579702). Fina lly, there are two fiel d studies (141-2, honey bee residue on foliage; MRIDs 44024961 and 45579702) th at have not been fully reviewed but both studies reported an increase in honey bee mortality and reduced foraging activity when compared to the control or pre-exposure period. While it is noted that MRIDs 45579702, 44024961, and 45579702 require further review (which will be completed prior to the risk assessment) the information in these studies along with the data in the acceptable study provide a weight of evidence that exposure to pymetrozine might adversely affect bees. Because sublethal
effects were observed in 90% of the bees at the three highes t treatments at 24 hours after treatment, and those effects pe rsisted (up to 90% in the high est treatment group) throughout the study (96 hours), the 96-hour observa tion duration may not fully captu re the extent of the effects ( e.g. , cessation of feeding, decreasing recovery, or mortality). Th erefore, additional data are needed to fully understand the le vel of risk that pymetrozine can pose to the honey bee.



## Ecological Incidents

As of January 29, 2013, no incidents were reporte d in the Ecological Incident Information System (EIIS, version 2.1- maintained by the EPA), the Avian Monitoring Information System (AIMS- maintained by the American Bird Cons ervancy), or in the ID S Aggregate Incident Reports’ Database (maintained by the EPA).



# Conceptual Model

The environmental fate properties of pymetrozine indicate that direct spray, spray drift, and runoff (either via dissolved phase or particle transpor t of sorbed pymetrozine) represent potential transport mechanisms. These pathways may resu lt in a wide range of potential aquatic and terrestrial exposure scenarios to both pymetrozin e as well as its envir onmental transformation products.

### 25 

# Analysis Plan

Stressors of Concern

Drinking Water Exposure Assessment

The major degradate, CGA359009 is currently c onsidered a residue of concern in drinking

water 8 

### ; however, if any additional environmenta l transformation products of pymetrozine identified as a potential toxicological concern with similar toxicity as the parent will be considered using a total toxi c residue (TTR) approach.

Ecological Risk Assessment

In order to address the risk hypot hesis, the potential for adverse effects on the environment will be estimated. The use, environmental fate, a nd ecological effects of pymetrozine and its degradation products will be charact erized and integrated to assess the overall risks. There are a total of six major degradation products (CGA-359009, CGA 215525, GS 23199, CGA 249257, CGA 300407, and CGA 180777 ). Toxicity data are not available for these degradation products. Additionally, a query of the European Pesticide Properties Database (PPDB) 10 

### did not show any studies submitted for the degradation products. In order to gain an understanding of the potential toxicity of the degradates, a structure activity anal ysis using ECOSAR (V1.1) was conducted. Based on the ECOSAR output, five of th e six degradates [(CGA-359009, CGA 215525, GS 23199 and CGA 249257 predicted with the “hydrazine training set”); CGA 300407-predicted with the “aldehydes” training set] are estimated to exhibit approximately equal toxicity to pymetrozine (See APPENDIX F for the ECOSAR input and output ). The last degradate, CGA 180777, is estimated to be less toxic and is also only formed under anaer obic aquatic conditions, therefore , this degradate will not be considered as a residue of concern.

A total toxic residue approach wi ll be used to assess the exposure to pymetrozine (FIFRA SAP, 2008), thus, this assessment will assume that the toxicity of the de gradation products (CGA359009, CGA 215525, GS 23199, CGA 249257, and C GA 300407) are equivalent to pymetrozine. Risk quotients (RQs) will be derive d for total toxic residues (pymetrozine and the degradates listed above) by dividi ng estimated environmental concen trations (EECs) by the most sensitive endpoint from the relevant, avai lable toxicity data for pymetrozine.



## 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 (P RZM) coupled with the EXposure Analysis Model System

10 PPDB. Pesticide Properties Database . Universityof Hertfordshire. http://sitem.herts.ac.uk/aeru/footprint/index2.htm

### 26 (EXAMS). Model input values will be consistent with the most recent version of the Input Parameter guidance (current version 2.1; USEP A 2009). The model used to produce terrestrial EECs on food items is T-REX. Using the TREX mode l, we will assume that the default half-life value of 35 days for foliar residue dissipation will capture the parent and degradates, unless data becomes available to suggest that the 35-day half-life is inadequate. Given that pymetrozine is systemic, there will be additional uncertainty asso ciated with the TREX estimates of the EECs.

The model used to derive EECs relevant to te rrestrial and wetland plants is TerrPlant. The AgDRIFT spray drift model (v2.01; May 2001) is used to assess exposures of organisms to bifenazate deposited on terrestrial or aquatic habitats by spray drift. These models are parameterized using relevant reviewed registrant-submitted environmental fate data. Because pymetrozine and its degradation product (CGA-359009) 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 esti mated environmental conc entrations of total toxic residues (pymetrozine and CGA-359009) will be used to calculate risk quotients.

For problem formulation, screens were conducte d for the potential exposure from drinking water and inhalation. For drinking water, the Screenin g Imbibition Program (SIP v. 1.0, Released June 15, 2010) 11 

### was used to calculate an upper bound estimate of exposure. Exposure from drinking water alone was determined to be a potentia l pathway of concern for avian and mammalian species on a chronic exposure basis. On an acute exposure basis, drinking water alone was not a concern for mammals and while there is a poten tial concern for birds identified there is also uncertainty because the toxi city value was non-definitive (i.e. the LD 50 

### >2000 mg/kg-bw) and the value of 2000 mg/kg-bw was used in the model as an upperbound estimate ( APPENDIX B ). Additionally, this modeling does not take into account that dri nking water may contribute to a total exposure that has the potenti al for effects on non-target animal s when aggregated with other exposure pathways (dietary food sources, dermal, i nhalation). Because there is a high degree of conservatism in the SIP 1.0 exposure estimate, there is limited expectation that use scenarios not triggering a SIP 1.0 concern would contribute significantly to a ggregate risks from water plus diet when a refined water exposure model is in corporated in the actual quantitative risk

assessment.

The S creening T ool for I nhalation R isk (STIR v.1.0, November 19, 2010) 12 

### was used to calculate an upper bound estimate of exposure from inhalati on. 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 ( APPENDIX C ). Inhalation exposure via spray drift and/or the vapor-phase of the pest icide 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 cont ribute to a total exposur e that has a potential for effects to non-target animals. However, the Agency does consider the relative importance of other routes of exposure in situ ations where data indicate that pesticide exposures through other routes may be potentially signi ficant contributors to wildlife risk (USEPA, 2004). The risk

11 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

. 12 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

.

### 27 characterization section will discus ses the impact of the considera tion of other routes of exposure

that have been identified as potentially important, and the degree of certainty associated with screening-level risk a ssessment conclusions.



## 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 ECOTOXicology database (ECOTOX) (USEPA, 2007 c ), which employs a literature search engine for lo cating chemical toxicity data for aquatic life, terrestrial plants,

and wildlife.

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 enda ngered species (“listed species”) from registered uses of pesticides in registration review. These assessments will be conducted in accordance with standard EPA pr ocedures and good scientific judgment. The process for evaluating potential risks to listed species is further described at http://www.epa.gov/oppfead1/enda nger/litstatus/riskasses.htm

.

Endocrine Disruptor Screening Program

Pymetrozine is not included in the first group of 67 chemicals issued an order to conduct Tier 1 EDSP testing. For additional info rmation on the EDSP program, visit http://www.epa.gov/endo/

.

### 28 

# Preliminary Identification of Data Gaps

Environmental Fate

Table 12 identifies the environmental fate studies submitted by the registrant, as well as study

classifications and whether or not additional data are needed in order to support the registration review exposure assessments. Rationale for the additional data requested is also presented.

Table 12. Status of Environmental Fate Data for Pymetrozine

OCSPP
Guideline Data Requirement Submitted
Studies (MRID) Study
Classifications Are data

needed to
conduct risk
assessment? Comments

835.2120 Hydrolysis 44024962
44024963
44024964 Supplemental Supplemental Supplemental Yes Results are not consistent between hydrolysis studies (MRIDs 44024964 and 44024963) for pH 5, with half-lives ranging from 12 to 28 days. Because hydrolysis appears to an important route of dissipation in acidic environments, additional abiotic hydrolysis data for pH 5 are needed.

835.2240 Aqueous Photolysis 44411321

44471702

44411322 Supplemental Supplemental Supplemental No a A major degradate (up to 28.9% AR)
was not identified.

Identification of this transformation product is needed to rule out the potential that it is a residue of toxicological concern. In absence of the data, this residue may be considered as part of a TTR approach in modeling to

account for this un certainty.

835.2410 Soil Photolysis 44411324

44411325 Supplemental Supplemental No a A large amount of unextracted residues (>75%) was observed in the irradiated samples compared to the dark control (<20%) at study termination.

835.4100 Aerobic Soil

Metabolism 44024965
44024966 Supplemental Supplemental No a Current guidelines recommend aerobic

soil metabolism data be submitted for a

total of five different soils. In absence of

this data the calculated aerobic soil

metabolism half-life value will be multiplied by 3 to generate model input values. This adjustment factor is applied

to account for the uncer tainty associated
with the variation in transformation in different soil systems.

835.4200 Anaerobic Soil

Metabolism No data No a Results from the anaerobic aquatic metabolism study will be used.

### 29 835.4300 Aerobic Aquatic

Metabolism No data Yes a These data have not been submitted to

the EPA.

In absence of this data the calculated aerobic soil metabolism half-life input values will be multiplied by 2 (6 times

the aerobic soil metabolism half-life values) to generate model input value for aerobic aquatic metabolism. This adjustment factor is applied to account for the uncertainty associated with the
different between aerobic soil and aerobic aquatic metabolism.

835.4400 Anaerobic Aquatic

Metabolism 44024967
44024968 Supplemental Supplemental No Current guidelin es recommend anaerobic aquatic metabolism data be
submitted for a total of two different sediment:water systems.

835.1230

835.1240 Adsorption/ desorption and leaching 44024969 Acceptable No

835.1410 Volatility – laboratory No data No a Pymetrozine is not expected to volatilize based on the reported vapor pressure and Henry’s Law Constant.

850.6100

Terrestrial field dissipation 44411334
44647901 Supplemental

Yes Storage stability for the CGA-180777, CGA-249257, and CGA-359009 were inadequate. Because CGA-359009 is one of the identified residues of concern, submission of storage stability studies

are needed. 44647903

44411338 Supplemental

44471703 Supplemental

Analytical

method

in soil 44647902 Supplemental No Analytical methods were inadequate for detecting CGA-249257 44411333

44411337 Supplemental

44411339

44411332 Supplemental

Analytical

method in water Not applicable No direct application to aquatic

environments

850.1730 Fish

bioconcentration No data no a Pymetrozine is not expected to

bioaccumulate based on the calculated log K

ow (-0.18).

a. Additional data would reduce uncertainty. See comments.

### 30 

## Ecological Effects Data Gaps

Acceptable acute avian oral toxicity data fo r pymetrozine are available for the bobwhite quail. The acute oral study conducted with th e mallard duck is classified as supplemental

and is not suitable for use in risk assessment due to regurgitation that occurred in the three highest test concentrations. Additionally, 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 data be submitted for eith er a mallard duck or bobwhite quail, and for a passerine species. Therefore, an avian oral t oxicity test conducted with a passerine (OCSPP Guideline 850.2100) is needed. EFED recomme nds that a passerine study protocol be submitted for review by the Agency pr ior to initiation of this study.

Terrestrial plant toxicity studi es are needed to understand th e effects of pymetrozine to nontarget plants. Given that pymetrozine is syst emic in plants and that toxic effects were observed in the aquatic plants that were tested, EFED recommends that the Seedling Emergence and Seedling Growth and Vegetative Vigor toxicity tests (OCSPP Guidelines 850.4100 and 850.4150) toxicity tests are conducted.

The available data for the honey bee ( Apis mellifera L. ) is considered acceptable; however, the study duration for the acute oral test was only for 48 hours. While 48 hours is considered an acceptable period of time according to the guid eline, in the case of pymetrozine there is uncertainty when considering that the mode of action can take several days before mortality occurs (as seen with the target pests). A dditionally, based on the available acute oral study (MRID 44024961), there were several signs of t oxicity (including uncoordinated movements and bees lying on their sides and backs) noted at all exposure levels s uggesting that the mode of action may extend beyond inhibi tion of feeding behavior. A pr eliminary review of a more recent acute oral/contact study (MRID 45579702) show s that when bees were exposed (oral) and observed for a longer duration (6 hours and 96 hours, respectively), that while mortality was low (a similar observation to the earlier study), bees at th e three highest treatments (1.01, 8.77, and 62.71 μg a.i./bee) exhibited sublethal effects ( e.g., bees showing symptoms of paralysis/restricted movement of legs) at 24 hours after treatment in 90% of the bees, and by the end of the study the bees were only partially recovered with 57.5%, 30%, and 10% healthy in the 1.0, 8.77, and 62.7 μg a.i./bee treat ments, respectively. In this same study, a significant reduction in feeding was also observed at the 0.12, 1.01, 8.77, and 62.71 μg a.i./bee treatment levels when compared to the control (MRID 45579702) . Finally, there are two field studies (141-2-Honey bee residue on foliage; MRIDs 44024961 and 45579702) that reported an increase in honey bee mortality and reduced foraging activity when compared to the control or pre-exposure period. Wh ile it is noted that MRIDs 45579702, 44024961, and 45579702 require further review (which will be co mpleted prior to the risk assessment) the information in these studies along with the data in the acceptable study provide a weight of evidence that exposure to pymetrozine might adve rsely affect bees. Because sublethal effects
were observed in 90% of the bees at the three highest treatments at 24 hours after treatment, and those effects persisted (up to 90% in the highest treatment group) throughout the study (96 hours), the 96-hour observation duration may not fully capture the ex tent of the effects ( e.g. , cessation of feeding, decreasi ng recovery, or mortality). Therefore, EFED recommends

### 31 the submission of an OECD semi-field toxic ity study (see data rationale below) to fully understand the level of risk that pymetrozine can pose to the honey bee. An acute oral and contact toxicity study (OCSPP Guideline 850.3020) with a longer exposure period ( e.g., ≥ 6 hours) and also an observation period that is long enough to determine the fate (recovery or mortality) of the bees exhibiting sublethal effects is recommended to reduce the current uncertainty with the available data.

OECD Guideline 75: Honey bee (Apis me llifera L.) Brood Test under Semi-field
Conditions : realistic exposures and effects on va rious measures of brood development and bee health. This study also provides m easures of residue in pollen and nectar. Bee bread can be spiked and exposure to test ma terial assured. Available studies provide a weight of evidence that indicates exposure to pymetrozine might adversely affect bees.

Because sublethal effects were observed in 90% of the bees at the three highest treatments at 24 hours after treatment, and those effects persiste d (up to 90% in the highest treatment group) throughout the study (96 hours), the 96-hour observation duration may not fully capture the extent of the effects ( e.g. , cessation of feeding, decreasing recovery, or mort ality). EFED recommends that the observation period of exposed honey bees be extended to 14-days to capture the full potential of effects due to exposure to pymetrozine residues. EFED r ecommends that a proposed protocol be submitted prior to ini tiation of the study.

Table 13 provides a summary of the status of effects data for Pymetrozine.

Table 13. Status of Environmental Ecologica l Toxicity Fate Data for Pymetrozine

Guideline

Number Data Requirement Submitted
Studies

MRID

Number Study
Classifications Are data
needed for
risk
assessment? Comments

850.2100 Avian acute oral LD 50 (bobwhite quail) (mallard duck) 44024908
44024907 Acceptable Supplemental Yes Currently there is a data gap because acceptable data are only available for one species. The supplemental study with the mallard is not acceptable for quantitative use in risk assessments. Therefore,

data are needed on a passerine species to get a better understanding of species sensitivity to pymetrozine.

850-2200 Avian subacute dietary LC 50

(mallard duck) (bobwhite quail) 44024910
44024909 Acceptable Supplemental No

### 32 850-2300 Avian reproduction (bobwhite quail) (mallard duck) (mallard duck) 44024911

44411304

46276601 Acceptable Supplemental Supplemental No

850-1075 Freshwater fish acute LC 50 (rainbow trout) (bluegill sunfish ) 44024913
44024912 Acceptable Acceptable No

850-1300 Freshwater invertebrate acute

EC 50 (daphnia) 44024914 Acceptable No

850-1075 Estuarine/marine fish acute LC 50 (sheepshead minnow) 44024916 Acceptable No

850- 1025;1035 Estuarine/marine invertebrate

acute EC 50 (eastern oyster) (mysid) 44024917
44024915 Acceptable Supplemental No

850-1400 Freshwater fish early life stage (rainbow trout) 44024918 Supplemental No Classified as supplemental
because the solvent

concentration used exceeded the guideline

recommendations and the highest tested concentration (only up to 13 mg a.i./L) was not high enough to produce adverse effects. However, this study is considered acceptable for quantitative use because 13 mg a.i./L is much higher than the expected

environmental

concentrations.

850-1300 Freshwater invertebrate life cycle (daphnia) 44024919 Acceptable No

850-1400 Estuarine/marine fish life cycle (sheepshead minnow) No study -- No Due to the general low toxicity to fish, the value of this data to the ecological

risk assessment is low. The
chronic freshwater data will serve as a surrogate given the similarity in the acute toxicity values.

### 33 850-1350 Estuarine/marine invertebrate life cycle (mysid) No study -- No Due to the general low toxicity to aquatic invertebrates , the value of this data to the ecological

risk assessment is low. The

chronic freshwater data will serve as a surrogate given the similarity in the acute toxicity values of the freshwater daphnid and the saltwater mysid.

850-1500 Freshwater fish full life cycle No study -- No Due to the general low toxicity to fish on a chronic exposure basis, the value of this data to the ecological
risk assessment is low.

850-1950 Aquatic Field Study No study -- No

81-1 Acute mammalian oral LD 50 (rat) 44024926 Acceptable No

81-3 Mammalian Inhalation (rat) 44024930 Acceptable No

83-4 Mammalian Reproduction (rat) 44024950 Acceptable No

850-4100 Seedling Emergence and Seedling Growth No study -- Yes A study is needed to

understand the effects of pymetrozine to non-target plants. Given that pymetrozine is systemic in plants and that toxic effects
were observed in the aquatic plants that were tested, toxicity data are necessary for ecological

risk assessment.

850-4150 Vegetative Vigor No study -- Yes A study is needed to

understand the effects of pymetrozine to non-target plants. Given that pymetrozine is systemic in plants and that toxic effects

were observed in the aquatic plants that were tested, toxicity data are necessary for ecological
risk assessment.

850-4500

850.4550 Aquatic plant algae (green algae) 44024959 Acceptable No Only one species was tested rather than four, however, given that the EECs from previous assessments were

well below the NOAEC (the RQ would be <0.01),
the value of additional data

is low.

### 34 850-4400 Aquatic plant acute EC 50 (duckweed) 44024960 Supplemental No This study was classified as supplemental because the

test material was unstable
in solution and the EC50 is

based on the initial

measured concentration

rather than the mean

measured concentration. As a result, the toxicity may be underestimated, however, given that the EECs from previous assessments were

well below the NOAEC (the RQ would be 0.001),

additional data are not

needed at this time.

850-3020/

Nonguideline Acute honey bee contact LD 50 Acute honey bee oral LD 50/ 44024961
45579702 Acceptable

In review No

Nonguideline OECD Guideline 75: Honey bee
Brood Test Under Semi-field

Conditions (Semi-field Toxicity Study) No study -- Yes Additional data are needed to fully understand the level

of risk pymetrozine poses

to the honey bee (see

discussion and rationale

above). A proposed protocol should be

submitted for review and approval.

850-3030 Honey Bee Residue on Foliage 45579701
45579703 In review No

850-3040 Honey Bee Field Testing for

Pollinator No study -- No



### Appendices

– 

### APPENDIX A. Environmental Fate Kinetic Analyses

– 

### Appendix B. Results of SIP

– 

### Appendix C. Results of STIR

– 

### Appendix D. Ecological Effects Bibliography

– 

### Appendix E. Environmental Fate Bibliography

– 

### Appendix F. ECOSAR Results

### 35 APPENDIX A Environmental Fate Kinetic Analyses

Hydrolysis

### 36

### 37 Aquatic Photolysis

### 38 Soil Photolysis

### 39

### 40 APPENDIX B
Results of SIP

Parameter Value

Chemical name Pymetrozine

Solubility (in water at 25 o C; mg/L) 290

Mammalian LD 50 (mg/kg-bw) 5955
Mammalian test species laboratory rat
Body weight (g) of "other" mammalian species

Mammalian NOAEL (mg/kg-bw) 13.9
Mammalian test species laboratory rat
Body weight (g) of "other" mammalian species

Avian LD 50 (mg/kg-bw) 2000
Avian test species northern bobwhite quail
Body weight (g) of "other" avian species
Mineau scaling factor 1.15

Mallard NOAEC (mg/kg-diet) 0
Bobwhite quail NOAEC (mg/kg-diet) 100
NOAEC (mg/kg-diet) for other bird species 0
Body weight (g) of other avian species
NOAEC (mg/kg-diet) for 2nd other bird species 0
Body weight (g) of 2nd other avian species

Table 2. Mammalian Results

Parameter Acute Chronic
Upper bound exposure (mg/kg-bw) 49.8800 49.8800
Adjusted toxicity value (mg/kg-bw) 4580.3512 10.6913
Ratio of exposure to toxicity 0.0109 4.6655

Conclusion* Drinking water exposure alone is NOT a potential

concern for mammals Exposure through drinking water alone is a potential

concern for mammals

Table 3. Avian Results

Parameter Acute Chronic
Upper bound exposure (mg/kg-bw) 234.9000 234.9000
Adjusted toxicity value (mg/kg-bw) 1440.8590 10.6298
Ratio of exposure to acute toxicity 0.1630 22.0982

Conclusion* Exposure through drinking water alone is 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 dr inking water may contribute to a total exposure that has potential for effects to non-target animals.

### 41 APPENDIX C
Results of STIR

Input

Application and Chemical Information

Enter Chemical Name Pymetrozine

Enter Chemical Use Ornamental/Xmas
Is the Application a Spray? (enter y or n) y If Spray What Type (enter ground or air) ground
Enter Chemical Molecular Weight (g/mole) 217.2
Enter Chemical Vapor Pressure (mmHg) 3.00E-08
Enter Application Rate (lb a.i./acre) 0.3125

Toxicity Properties

Bird

Enter Lowest Bird Oral LD 50 (mg/kg bw) 2000
Enter Mineau Scaling Factor 1.15
Enter Tested Bird Weight (kg) 0.178

Mammal

Enter Lowest Rat Oral LD 50 (mg/kg bw) 5955

Enter Lowest Rat Inhalation LC 50 (mg/L) 1.8
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 ) 3.51E-04
Maximum 1-hour Vapor Inhalation Dose (mg/kg) 4.41E-05

Adjusted Inhalation LD 50 3.37E+00

Ratio of Vapor Dose to Adjusted Inhalation LD 50 1.31E-05 Exposure not Likely Significant
Maximum Post-treatment Spray Inhalation Dose (mg/kg) 3.30E-02

Ratio of Droplet Inhalation Do se to Adjusted Inhalation LD 50 9.80E-03 Exposure not Likely Significant

Results Mammalian (0.015 kg )

Maximum Vapor Concentration in Air at Saturation (mg/m 3 ) 3.51E-04
Maximum 1-hour Vapor Inhalation Dose (mg/kg) 5.54E-05

Adjusted Inhalation LD 50 1.07E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 5.17E-07 Exposure not Likely Significant
Maximum Post-treatment Spray Inhalation Dose (mg/kg) 4.15E-02

Ratio of Droplet Inhalation Do se to Adjusted Inhalation LD 50 3.87E-04 Exposure not Likely Significant

Input

### 42 Application and Chemical Information

Enter Chemical Name Pymetrozine

Enter Chemical Use Potatoes
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) 217.2
Enter Chemical Vapor Pressure (mmHg) 3.00E-08
Enter Application Rate (lb a.i./acre) 0.1719

Toxicity Properties

Bird

Enter Lowest Bird Oral LD 50 (mg/kg bw) 2000
Enter Mineau Scaling Factor 1.15
Enter Tested Bird Weight (kg) 0.178

Mammal

Enter Lowest Rat Oral LD 50 (mg/kg bw) 5955

Enter Lowest Rat Inhalation LC 50 (mg/L) 1.8
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 ) 3.51E-04
Maximum 1-hour Vapor Inhalation Dose (mg/kg) 4.41E-05

Adjusted Inhalation LD 50 3.37E+00

Ratio of Vapor Dose to Adjusted Inhalation LD 50 1.31E-05 Exposure not Likely Significant Maximum Post-treatment Spray Inhalation Dose (mg/kg) 1.65E-02 Ratio of Droplet Inhalation Do se to Adjusted Inhalation
LD 50 4.90E-03 Exposure not Likely Significant

Results Mammalian (0.015 kg ) Maximum Vapor Concentration in Air at Saturation (mg/m 3 ) 3.51E-04
Maximum 1-hour Vapor Inhalation Dose (mg/kg) 5.54E-05

Adjusted Inhalation LD 50 1.07E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 5.17E-07 Exposure not Likely Significant Maximum Post-treatment Spray Inhalation Dose (mg/kg) 2.08E-02 Ratio of Droplet Inhalation Do se to Adjusted Inhalation
LD 50 1.94E-04 Exposure not Likely Significant

### 43 APPENDIX D Ecological Effects Bibliography

Avian Single Dose Oral Toxicity

44024907 Hakin, B. (1993) CGA-215944: Acute Oral T oxicity (LD50) to Mallard Duck: Lab Project Number: CBG 560/921044: 478-92. Unpublished study prepared by Huntingdon Research Centre, Ltd. 46 p.

44024908 Hakin, B. (1993) CGA-215944: Acute Oral T oxicity (LD50) to Bobwhite Quail: Lab Project Number: CBG 559/921043: 477-92. Unpublished study prepared by Huntingdon Research Centre, Ltd. 42 p.

Avian Dietary Toxicity

44024909 Hakin, B. (1992) CGA-215944: Sub-Acute Di etary Toxicity (LC50) to Bobwhite Quail: Lab Project Number: CBG 557/920414: 475-92. Unpublished study prepared by Huntingdon Research Centre, Ltd. 36 p.

44024910 Hakin, B. (1992) CGA-215944: Sub-Acute Di etary Toxicity (LC50) to Mallard Duck: Lab Project Number: CBG 558/920382: 476-92. Unpublished study prepared by Huntingdon Research Centre, Ltd. 33 p.

Avian Reproduction

44024911 Taliaferro, L.; Brewer, L. (1996) The Repr oductive Toxicity Test of CGA-215944 Technical in Northern Bobwhite, Colinus virg inianus: Lab Project Number: 029502: 140-95. Unpublished study prepared by Ecotoxicology an d Biosystems Associates, Inc. 251 p.

44411304 Taliaferro, M.; Miller, V. (1997) The Repr oductive Toxicity Test of CGA-215944 in the Mallard Duck (Anas platyrhynchos): La b Project Number: 141-95: 029609: EBA-029609. Unpublished study prepared by EBA, Inc. 311 p.

45404301 Wall, S. (2001) Response to EFED Concerni ng Acceptability of Existing Chronic Mallard Reproduction Study (MRID 44411304): Pymetroz ine: Lab Project Number: 1170-00. Unpublished study prepared by Syngenta Crop Protection, Inc. 9 p.

46276601 Stafford, J. (2004) CGA-215944 Technical: Repr oductive Toxicity Test with the Mallard Duck (Anas platyhynchos): Final Report. Project Number: 191/01, 1781/4100. Unpublished study prepared by Springborn Smithers Laboratories. 136 p.

44024912 Boeri, R.; Kowalski, P.; Ward, T. (1994) CGA-215944: Acute Flow-Through Toxicity of CGA-215944 to the Bluegill, Lepomis macrochirus: Lab Project Number: 443-CG: 112-94. Unpublished study prepared by T R Wilbury Labs., Inc. 28 p.

44024913 Boeri, R.; Kowalski, P.; Ward, T. (1994) CGA-215944: Acute Flow-Through Toxicity of

### 44 CGA-215944 to the Rainbow Trout, Oncorhync hus mykiss: Lab Project Number: 444-CG: 111-94. Unpublished study prepared by T R Wilbury Labs., Inc. 27 p.

Acute Toxicity to Freshwater Invertebrates

44024914 Boeri, R.; Kowalski, P.; Ward, T. (1994) CGA-215944: Acute Flow-Through Toxicity of CGA-215944 to the Daphnia, Daphnia magna: Lab Project Number: 442- CG: 113-94. Unpublished study prepared by T R Wilbury Labs., Inc. 29 p.

Acute Toxicity to Estu arine/Marine Organisms

44024915 Boeri, R.; Kowalski, P.; Ward, T. (1994) CGA-215944: Acute Flow-Through Toxicity of CGA-215944 to the Mysid, My sidopsis bahia: Lab Project Number: 445- CG: 115-94. Unpublished study prepared by T R Wilbury Labs., Inc. 28 p.

44024916 Boeri, R.; Kowalski, P.; Ward, T. (1994) CGA-215944: Acute Flow-Through Toxicity of CGA-215944 to the Sheeps head Minnow, Cyprinodon variegatus: Lab Project Number: 446-CG: 114-94. Unpublis hed study prepared by T R Wilbury Labs., Inc. 27 p.

44024917 Boeri, R.; Kowalski, P.; Ward, T. (1994) CGA-215944: Acute Flow-Through Mollusk Shell Deposition Test with CGA-215944: Lab Project Number: 447-CG: 116-94. Unpublished study prepared by T R Wilbury Labs., Inc. 28 p.

45208708 Wall, S. (2000) Response to EFED C oncerning Acceptability of Existing Acute Mysid Shrimp Study: Lab Project Numb er: 1169-00. Unpublished study prepared by Novartis Crop Protection. 11 p.

Fish Early Life Stage/Aquatic In vertebrate Life Cycle Study

44024918 Boeri, R.; Kowalski, P.; Ward, T. (1995) CGA-215944: Early Life-Stage Toxicity of CGA-215944 to the Rainbow Trout, Oncor hynchus mykiss: Lab Project Number: 504-CG: 117-94. Unpublished study prepared by T R Wilbury Labs., Inc. 67 p.

44024919 Boeri, R.; Kowalski, P.; Ward, T. ( 1995) CGA-215944: Chronic Toxicity of CGA215944 to the Daphnia, Daphnia magna: Lab Project Number: 449-CG: 118-94. Unpublished study prepared by T R Wilbury Labs., Inc. 41 p.

### 45 Acute oral toxicity in rats

44024926 Glaza, S. (1991) CGA-215944 Technical: Acute Oral Toxici ty Study of CGA215944 Technical in Rats: (Revised) Fina l Report: Lab Project Number: HWI 10700623. Unpublished study prepared by Hazleton Wisconsin, Inc. 33 p.

44024927 Glaza, S. (1995) CGA-215944 Technical: Acute Oral Toxici ty Study of CGA215944 50WP-A in Rats: Final Repor t: Lab Project Number: CHW 50902683. Unpublished study prepared by Corning Hazleton Inc. 17 p.

44411306 Glaza, S. (1997) Acute Oral Toxicity Study of CGA-215944 50WG in Rats: Final Report: Lab Project Number : COVANCE 70402016: 70402016: 334-97. Unpublished study prepared by Covance Labs., Inc. 19 p.

44416303 Glaza, S. (1997) Acute Oral Toxi city Study of CGA- 215944/CGA-114597 50WPExp in Rats: Final Report: Lab Proj ect Number: COVANCE 70201590. Unpublished study prepared by Covance Labs, Inc. 20 p.

Acute inhalation toxicity in rats

44024930 Hartmann, P. (1991) CGA-215944 Technical: Ac ute Inhalation Toxicity in the Rat: Lab Project Number: 911186: (Z:\CF -DOC\TOX.0326B2JS). Unpublished study prepared by Ciba-Geigy Ltd. 34 p.

44024931 Bennick, J. (1996) CGA-215944 50WP-A: Acut e Inhalation Toxicity Study in Rats: Final Report: Lab Project Number: 2670-96. Unpublished study prepared by Stillmeadow, Inc. 21 p.

44411308 Bennick, J. (1997) Acute Inhalation T oxicity Study in Rats: CGA-215944 50WG: Final Report: Lab Project Number: 3471-97. Unpublished study prepared by Stillmeadow, Inc. 20 p.

44416305 Bennick, J. (1997) Acute Inhalation T oxicity Study in Rats (CGA-215944/CGA114597 50WP) Final Report: Lab Proj ect Number: 3327-97: SP-FF81-3.C3. Unpublished study prepared by Stillmeadow, Inc. 27 p.

2-generation repro.-rat

44024950 Fitzgerald, R. (1993) CGA-215944 Tec hnical: Two-Generation Reproduction Study in Rats: Final Report: Lab Proj ect Number: 901486: TOX-0228G3LM.1. Unpublished study prepared by Ciba-Geigy Ltd. 950 p. Relates to L0000332.

### 46 Aquatic plant growth

44024959 Boeri, R.; Kowalski, P.; Ward, T. (1995) CGA-215944: Toxicity of CGA-215944 to the Freshwater Alga, Selenastrum capri cornutum: Lab Project Number: 668-CG: 143-95. Unpublished study prepared by T R Wilbury Labs., Inc. 28 p.

44024960 Boeri, R.; Kowalski, P.; Ward, T. (1995) CGA-215944: Toxicity of CGA-215944 to the Duckweed, Lemna gibba G3: Lab Project Number: 669-CG: 142-95. Unpublished study prepared by T R Wilbury Labs., Inc. 28 p.

Honey bee acute contact

44024961 Decker, U. (1993) CGA-215944: Laboratory Testing for Oral and Contact Toxicity of CGA-215944 Tech to Honey Bees, Apis Melliferal L: Lab Project Number: RCC 331648: 480-92. Unpublished study prepared by RCC, Research & Consulting Co., Ltd. and BRL, Biological Resear ch Laboratories, Ltd. 24 p.

45579702 Kling, A. (2001) CGA-215944 Tech. (Pymetro zine Tech.): Acute Contact and Oral Toxicity on the Honey Bee, Apis mellifera L.: Final Report: Lab Project Number: 2012504: 2538-01: 20011366/02-BLEU. Unpublished study prepared by Arbeitsgemeinschaft, GAB Biotechnologie GmbH & IFU Umweltanalytik GmbH. 52

p.

Honey bee residue on foliage

45579701 Schur, A. (2001) Assessment of Side Effects of CGA-215944 50 WG (A-9364A) on the Honey Bee (Apis mellifera L.) in the Field Following Application to Phacelia tanacetifolia During Bee-Flight in Spai n: Final Report: Lab Project Number: 2002688: 2540-01: 20011175/S1BFEU. Unpublished study prepared by Arbeitsgemeinschaft, GAB Biotechnologie GmbH & IFU Umweltanalytik GmbH. 95

p.

45579703 Schur, A. (2001) Assessment of Side Eff ect of Pymetrozine Tech 50 WG (A-9364 A) on the Honey Bee (Apis mellifera L.) in Plum Orchard Following Application During Bee Flight: Final Report: Lab Proj ect Number: 2002692: 2545-01: 20011079/S1- BFEU. Unpublished study prepared by Arbeitsgemeinschaft, GAB Biotechnologie GmbH & IFU Umweltanalytik GmbH. 67 p.

### 47 APPENDIX E Environmental Fate Bibliography



## 161-1 Hydrolysis

MRID Citation Reference

44024962 McDonald, J. (1996) CGA-215944: Hydr olysis of (carbon-14)- (Triazine-6) CGA215944 Under Laboratory Conditions at pH 5: Supplemental Report: Lab Project Number: ABR-96020: 85-96. Unpublished study prepared by Ciba-Geigy Corp. 89 p.

44024963 Kirkpatrick, D. (1995) CGA-215944: The Hydrolysis of CGA-215944 Under Laboratory Conditions: Lab Project Number: CBG 570: CBG 570-1: HRC/CBG 570-1/930675. Unpublished study prepar ed by Huntingdon Life Sciences Ltd. 164 p.

44024964 Kirkpatrick, D. (1995) CGA-215944: (Pyridine-5-(car bon-14))- CGA-215944 Hydrolysis Under Laboratory Conditions: Lab Project Number: CBG 669: CBG 669/942733. Unpublished study prepared by Huntingdon Life Sciences Ltd. 127

p.



## 161-2 Photodegradation-water

MRID Citation Reference

44411321 Kirkpatrick, D. (1995) (Pyridine-5-(carbon 14)) CGA-2 15944 the Photolytic Degradation in Water: Lab Project Number: CBG 680: 489-94: CBG/942817. Unpublished study prepared by Huntingdon Life Sciences Ltd. 136 p.

44411322 Peters, J. (1997) Photodegradatio n of (carbon 14)-Triazine-6-CGA-215944 in pH Buffered Solution Under Artificial Light: Lab Project Number: ABR-97038: 262-97. Unpublished study prepared by Nova rtis Crop Protection, Inc. 127 p.

44411323 Parker, S. (1988) Development of a method to investigate the photodegradation of pesticides. Brighton Crop Protection Conference-Pest and Diseases p. 663-668.

44471702 Shaw, D. (1997) CGA-215944 (Triaz ine-6-(Carbon 14)) Rate of Photolytic Degradation in Water: Lab Project Number: CBG 811: 457-96: CBG 811/962086. Unpublished study prepared by Huntingdon Life Sciences Ltd. 118 p.

### 48 

## 161-3 Photodegradation-soil

MRID Citation Reference

44411323 Parker, S. (1988) Development of a method to investigate the photodegradation of pesticides. Bright on Crop Protection Conference-Pest and Diseases p. 663-668.

44411324 Schulze-Aurich, J. (1995) Photolys is (5-(carbon 14))--Pyridine-Labelled CGA215944 on Soil Surface Under Laboratory Conditions: Lab Project Number: 94SA02: 488-94: PR 94SA02. Unpublish ed study prepared by Ciba-Geigy Ltd. 195 p.

44411325 Schulze-Aurich, J. (1995) Photolysis (5-(carbon 14))--Triazine-Labelled CGA215944 on Soil Surface Under Laboratory Conditions: Lab Project Number: 93MU02: 606-93: PR 50/94. Unpublished study prepared by Ciba-Geigy Ltd. 176 p.

45208701 Sparrow, K. (2000) Photodegradati on of (carbon 14)-Pyridinyl-2-CGA-215944 on Soil Surface Under Artificial Light: Lab Project Number: 543-00. Unpublished study prepared by Novartis Crop Protection, Inc. 134 p.

45208702 Sparrow, K. (2000) Photodegradati on of (carbon 14)-Triazinyl-2-CGA-215944 on Soil Surface Under Artificial Light: Lab Project Number: 544-00. Unpublished study prepared by Novartis Crop Protection, Inc. 128 p.



## 162-1 Aerobic soil metabolism

MRID Citation Reference

44024965 Das, Y. (1996) CGA-215944: Metabo lism of (Pyridinyl-5- (carbon-14)) CGA215944 Under Aerobic Soil Conditions: Lab Project Number: 94011: 45-94. Unpublished study prepared by Innovative Scientific Services, Inc. 479 p.

44024966 Das, Y. (1996) CGA-215944: Metabo lism of (Triazinyl-6- (carbon-14)) CGA215944 Under Aerobic Soil Conditions: Lab Project Number: 94013: 47-94. Unpublished study prepared by Innovative Scientific Services, Inc. 487 p.

44024986 Phelps, W. (1996) CGA-215944: Ecochemistry of CGA-215944: Lab Project Number: ABR-96030. Unpublished study prepared by Ciba-Geigy Corp. 54

p.



## 162-3 Anaerobic aquatic metab.

MRID Citation Reference

44024967 Das, Y. (1996) CGA-215944: Metabo lism of (Pyridinyl-5- (carbon-14)) CGA215944 Under Anaerobic Aquatic Soil C onditions: Lab Project Number: 94012: 46-94. Unpublished study prep ared by Innovative Scientific Services, Inc. 513 p.

44024968 Das, Y. (1996) CGA-215944: Metabo lism of (Triazinyl-6- (carbon-14)) CGA-

### 49 215944 Under Anaerobic Aquatic Soil C onditions: Lab Project Number: 94014: 48-94. Unpublished study prep ared by Innovative Scientific Services, Inc. 606 p.

44024986 Phelps, W. (1996) CGA-215944: Ecochemistry of CGA-215944: Lab Project Number: ABR-96030. Unpublished study prepared by Ciba-Geigy Corp. 54

p.



## 163-1 Leach/adsorp/desorption

MRID Citation Reference

44024969 Gohdes, M. (1996) CGA-215944: The Adsorption and Desorption of (carbon-14) CGA-215944 on Representative Agricultural Soils: Lab Project Number: CHW 6117-293: 501-95. Unpublished study prepared by Corning Hazleton Inc. 99 p.

44024970 Gohdes, M. (1996) CGA-215944: Column Leaching Characteristics of (carbon-14)-CGA-215944 in Four Soil Types: Lab Project Number: CHW 6117-297: 55-95. Unpublished study prepared by Corning Hazleton Inc. 146

p.

44024971 Gohdes, M. (1996) CGA-215944: Co lumn Leaching Characteristics of Aged (carbon-14)-Triazine-CGA-215944 in Four Soil Types: Lab Project Number: CHW 6117-299: 56-95. Unpublished stud y prepared by Corning Hazleton Inc. 355 p.

44024972 Gohdes, M. (1996) CGA-215944: Co lumn Leaching Characteristics of Aged (carbon-14)-Pyridine-CGA-215944 in F our Soil Types: Lab Project Number: CHW 6117-317: 57-95. Unpublished stud y prepared by Corning Hazleton Inc. 359 p.

44024986 Phelps, W. (1996) CGA-215944: Ecochemistry of CGA-215944: Lab Project Number: ABR-96030. Unpublished study prepared by Ciba-Geigy Corp. 54

p.

44411326 Gohdes, M. (1997) The Adsorption and Desorption of (carbon 14)-CGA359009 on Representative Agricultural Soils: Lab Project Number:
COVANCE 6117-349: 6117-349: 224-96. Unpublished study prepared by Covance Labs., Inc. 103 p.

44411327 Gohdes, M. (1997) The Adsorption and Desorption of (carbon 14)-CGA180777 on Representative Agricultural Soils: Lab Project Number:
COVANCE 6117-343: 6117-343: 227-96. Unpublished study prepared by Covance Labs., Inc. 110 p.

44411328 Gohdes, M. (1997) The Adsorption and Desorption of (carbon 14)-CGA300407 on Representative Agricultural Soils: Lab Project Number:
COVANCE 6117-345: 6117-345: 226-96. Unpublished study prepared by Covance Labs., Inc. 83 p.

44411329 Gohdes, M. (1997) The Adsorption and Desorption of (carbon 14)-GS23199 on Representative Agricultural Soils: Lab Project Number:
COVANCE 6117-365: 6117-365: 48-97. Unpublished study prepared by Covance Labs., Inc. 82 p.

### 5044411330 Gohdes, M. (1997) The Adsorption and Desorption of (carbon 14)-CGA249257 on Representative Agricultural Soils: Lab Project Number:
COVANCE 6117-347: 6117-347: 225-96. Unpublished study prepared by Covance Labs., Inc. 87 p.

44411331 Gohdes, M. (1997) The Adsorption and Desorption of (carbon 14)-CGA215525 on Representative Agricultural Soils: Lab Project Number:
COVANCE 6117-295: 223-96: NOVAR TIS 223-96. Unpublished study prepared by Covance Labs., Inc. 137 p.

45208703 Sparrow, K. (2000) Soil Adsorption and Desorption of (Triazinyl-6(carbon 14)-CGA-215525-OH by the Batch Equilibrium Method: Lab Project Number: 63-99. Unpublished study pr epared by Novartis Crop Protection, Inc. 79 p.



## 164-1 Terrestrial field dissipation

MRID Citation Reference

44024973 Sandmeier, P. (1993) Outdoor Confined Accumulation Study on Rotational Crops and Field Dissipation after Bareground Soil Application of (Triazine-6- (carbon-14)) CGA-215944: Lab Project Number: 20/93: MR 20/93. Unpublished study prepared by Ciba-Geigy Ltd. 61 p.

44411332 Kabler, A. (1997) Independent Labora tory Validation of Novartis Method AG660: Analytical Method for the Determin ation of CGA-180777, A Metabolite of CGA-215944, in Soil by High Performa nce Liquid Chromatography with UV and MS Detection Including Validation Data: Final Report: Lab Project Number: 305-97: ABR-97045: AG-660. Unpublished study prepared by Novartis Crop Protection, Inc. 131 p.

44411333 Vargo, J. (1995) Analytical Met hod for the Determination of CGA-215944 and its Metabolites CGA-249257 and 2U in Soil by High Performance Liquid Chromatography with Mass Spectrometric Detection Including Validation Data: Lab Project Number: AG-641: 334-95: 344001. Unpublished study prepared by Novartis Crop Protection, Inc. 77 p.

44411334 Speth, R. (1997) Terrestrial Fiel d Dissipation of CGA-215944 50WP on Bare Soil in New York: Final Report: Lab Project Number: 189-95: 42962: 344001. Unpublished study prepared by Ciba Crop Protection. 481 p.

44411335 Vargo, J. (1997) Analytical Met hod for the Determination of GS-23199 and CGA-294849, Metabolites of CGA-2159 44, in Soil by High Performance Liquid Chromatography with UV Detection Including Validation Data: Lab Project Number: AG-666: 376-96: 344001. Unpublished study prepared by Novartis Crop Protection, Inc. 84 p.

44411336 Kabler, A. (1997) Independent Labora tory Validation of Novartis Method AG660: Analytical Method for the Determination of CGA-180777, a Metabolite of CGA-215944, in Soil by High Performa nce Liquid Chromatography with UV and MS Detection Including Validation Data: Amendment to the Final Report: Lab Project Number: 305-97. Unpublished study prepared by Novartis Crop Protection, Inc. 5 p.

44411337 Gresham, M. (1997) Independent Laboratory Validation of Ciba Analytical

### 51 Method No. AG-641, Analytical Method for the Determination of CGA-215944 and its Metabolites CGA-249257 and 2U in Soil by High Performance Liquid Chromatography with Mass Spectrometric Detection: Final Report: Lab Project Number: 630-95: 42961: AG-641. Unpublished study prepared by ABC Labs., Inc. 166 p.

44411338 Jones, G.; Fieser, J.; Speth, R. (1997) Terrestrial Field Dissipation of CGA215944 50WP on Crop (Tomatoes) and Bare Soil in California: Final Report: Lab Project Number: 190-95: 42686: 95512. Unpublished study prepared by ABC Labs., Inc. 539 p.

44411339 Vargo, J. (1996) Analytical Met hod for the Determination of CGA-180777, a Metabolite of CGA-215944, in Soil by High Performance Liquid Chromatography with UV and MS Detection Including Validation Data: Lab Project Number: AG-660: 285-96: 344001. Unpublished study prepared by Novartis Crop Protection, Inc. 74 p.

44411340 Coody, P.; Lightle, S. (1997) Soil Dissipation of (carbon 14)CGA-215944 Under Actual Field Conditions in Georgia: Interim Report: Lab Project Number: 1052: 279-96. Unpublished study prepared by PTRL East, Inc. and Hickey's Agri-Services Lab. 269 p.

44411341 Lightle, S.; Coody, P. (1997) Soil Dissipation of (carbon 14)CGA-215944 Under Actual Field Conditions in California: Interim Report: Lab Project Number: 1053: 280-96: 1973. Unpublished study prepared by PTRL East, Inc. and ABC Labs., California. 285 p.

44471703 Leppert, B.; Manuli, P. (1997) Terrestrial Field Dissipation Study for CGA215944 in Georgia: Lab Project Number: 191-95: SARS-95-GA-85: 191-95 PART A. Unpublished study prepared by Stewart Agricultural Research Services, Inc., Hickey's Agri-Services Laboratory and Novartis Crop Protection, Inc. 635 p.

44647901 Fieser, J.; Speth, R. (1998) Terr estrial Field Dissipation of CGA-215944 50WP on Bare Soil in New York: Final Report Addendum No.1: Lab Project Number: 189-95: 42962: AG-660. Unpublished study prepared by ABC Laboratories, Inc. 168 p.

44647903 Fieser, J.; Speth, R. (1998) Terr estrial Field Dissipation of CGA-215944 50WP on Crop (Tomatoes) and Bare Soil in California: Final Report Addendum No. 1: Lab Project Number: 190-95: 42686: AG-666. Unpublished study prepared by ABC Laboratories, Inc. 181 p.

44647904 Wickremesinhe, E.; Manuli, P. (1998) Terrestrial Field Dissipation of CGA215944 in Georgia: Final Report Addendum: Lab Project Number: 191-95: 003-26: AG-666. Unpublished study prepared by Centre Analytical Laboratories, Inc. 217 p.

45208704 Lightle, S.; Coody, P.; Atkins, R. (1999) Soil Dissipation of (carbon 14)CGA215944 Under Actual Field Conditions in Georgia: Lab Project Number: 1052:279-96. Unpublished study prepared by PTRL East, Inc., Hickey's AgriServices Laboratory, and Agvise Laboratories, Inc. 571 p.

45208705 Lightle, S.; Coody, P.; Atkins, R. (2000) Soil Dissipation of (carbon 14)CGA215944 Under Actual Field Conditions in California: Final Report: Lab Project Number: 1053: 280-96. Unpublished study prepared by PTRL East, Inc., PTRL West, Inc. and Agvise Laboratories, Inc. 561 p.

45208706 Lightle, S.; Marsh, J.; Atkins, R. (2000) Frozen Storage Stability of (carbon

### 52 14)CGA-215944 in Soil from Georgia: Final Report: Lab Project Number: 1060:321-96. Unpublished study prepared by PTRL East, Inc. 113 p.

45208707 Marsh, J.; Atkins, R. (2000) Frozen Storage Stability of (carbon 14)CGA215944 in Soil from California: Final Report: Lab Project Number: 1061: 394- 96. Unpublished study prepared by PTRL East, Inc. 121 p.

45387801 Speth, R.; Gresham, M. (2000) Te rrestrial Field Dissipation of CGA-215944 50WP on Bare Soil in New York Addendum No. 2 to Final Report (MRID 44411334): Lab Project Number: 42962: 189-95. Unpublished study prepared by Novartis Crop Protecti on, Inc. & ABC Labs., Inc. 44 p.

45387802 Speth, R.; Gresham, M. (2000) Te rrestrial Field Dissipation of CGA-215944 50WP on Crop (Tomatoes) and Bare Soil in California Addendum No. 2 to Final Report (MRID 44411334): Lab Project Number: 190-95: 42686. Unpublished study prepared by Novartis Crop Protection, Inc. & ABC Labs., Inc. 44 p.

45387803 Manuli, P.; Wickremesinhe, E. (2000) Terrestrial Field Dissipation Study for CGA-215944 in Georgia Addendum No. 2 to Final Report (EPA MRID 44471703): Lab Project Number: 003-026: 191-95. Unpublished study prepared by Centre Analytical Labs., Inc. 27 p.



## 165-1 Confined rotational crop

MRID Citation Reference

44024973 Sandmeier, P. (1993) Outdoor Confined Accumulation Study on Rotational Crops and Field Dissipation after Bareground Soil Application of (Triazine-6- (carbon-14)) CGA-215944: Lab Project Number: 20/93: MR 20/93. Unpublished study prepared by Ciba-Geigy Ltd. 61 p.

44024974 Gross, D. (1995) Outdoor Confined Accumulation Study on Rotational Crops after Bareground Soil Application of (Pyridine-5-(carbo n-14)) CGA-215944: Lab Project Number: 19/94: PMR 19/94: 92DG44. Unpublished study prepared by Ciba-Geigy Ltd. 52 p.

44572209 Fleischmann, T. (1998) Study on Confined Rotational Crops after Soil Application of Triazine-14C-CGA- 215944 and Pyridine-14C-CGA-215944: Lab Project Number: ABR-97018: 457-95: BIOL-97009. Unpublished study prepared by Novartis Crop Protection, Inc. 276 p. {860.1850}



## 165-2 Field rotational crop

MRID Citation Reference

44716601 Joseph, T. (1998) CGA-215944--Field Accumulation in Rotational Crops: Final Report: Lab Project Number: 31-97: 07-IR-008-97: 02-IR-037-97. Unpublished study prepared by Novartis Residue Chemistry and A&L Great Lakes Laboratories, Inc. 193 p. {OPPTS 860.1900}.

### 53 

## 875.1000 Background for application exposure monitoring test guidelines

MRID Citation Reference

46470503 Peranginangin, N. (2005) Pyme trozine (CGA-215944): Standard Index
Reservoir Scenario of Potato for Pymetrozine: A PRZM/EXAMS Modeling Study for Surface Wate r Exposure Assessment. Project Number: T0A3264/01. Unpublished study prepared by Syngenta Crop Protection, Inc. 35 p.



## Non-Guideline Studies

46470502 Perine, J.; Peranginangin, N. (2005) Pymetrozine (CGA-215944): Preliminary Drinking Water Exposure Assessment for Pymetrozine on Potatoes. Project Number: T002878/05. Unpublished study prepared by Syngenta Crop Protection, Inc. 9 p.

44647902 Petit, J. B. 1998. Independent laboratory validation of analytical method AG-666: "Analytical method for the determination of GS-23 199 and CGA-294849, metabolites of CGA-215944, in soil by high performance liquid chromatography with UV detection including validation data." Novartis Laboratory Project ID: 324-97 and CAL Laboratory Project ID: 003-29. Unpublished study performed by Centre Analytical Laboratories In c. (CAL), State College, PA; and submitted by Novartis Crop Pr otection, Inc., Greensboro, NC.

44024986 Phelps, W. (1996) CGA-215944: Ecochemistry of CGA-215944: LabProject Number: ABR-96030. Unpublished study prepared by CibaGeigy Corp. 54 p.

### 54 APPENDIX F
ECOSAR Results

ECOSAR Version 1.10 Results Page Pymetrozine SMILES : O=C2N(N=Cc1cccnc1)CC(=NN2)C

MOL FOR: C10 H11 N5 O1

MOL WT : 217.23

Log Kow: 0.891 (EPISuite Kowwin v1.68 Estimate) Log Kow: (User Entered) Log Kow: -0.18 (PhysProp DB exp value - for comparison only) Melt Pt: (User Entered for Wat Sol estimate) Melt Pt: 217.00 (deg C, PhysPr op DB exp value for Wat Sol est) Wat Sol: 9.936E+004 (mg/L, EPIS uite WSKowwin v1.43 Estimate) Wat Sol: (User Entered) Wat Sol: 290 (mg/L, PhysProp DB exp value)

Values used to Generate ECOSAR Pr ofile------------------------

--------------

Log Kow: 0.891 (EPISuite Kowwin v1.68 Estimate) Wat Sol: 290 (mg/L, PhysProp DB exp value)

Available Measured Data from ECOSAR Training Set

No Data Available ECOSAR v1.1 Class-sp ecific Estimations

Hydrazines

Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

========================= == ================== ======== ======

========== Hydrazines : Fish 96-hr LC50 5.211 Hydrazines : Daphnid 48-hr LC50 30.837 Hydrazines : Green Alg ae 96-hr EC50 1.250 Hydrazines : Fish ChV 0.400 ! Hydrazines : Daphnid ChV 2.596 ! Hydrazines : Green Algae ChV 0.332

========================= == ================== ======== ====== Neutral Organic SAR : Fish 96-hr LC50 1766.678 * (Baseline Toxicity) : Daphnid 48-hr LC50 757.371 * : Green Algae 96-hr EC50 697.971 *

: Fish ChV 153.045 : Daphnid ChV 66.418 : Green Algae ChV 92.108

### 55 Degradate (CGA-359009) ECOSAR Version 1.10 Results Page SMILES : O=C1(N(N=C(C(N1N=Cc2cnccc2)O)C))

MOL FOR: C10 H11 N5 O2

MOL WT : 233.23 Log Kow: -0.647 (EPISuite Kowwin v1.68 Estimate) Log Kow: (User Entered) Log Kow: (PhysProp DB exp value - for comparison only) Melt Pt: (User Entered for Wat Sol estimate) Melt Pt: (deg C, PhysProp DB exp value for Wat Sol estimate) Wat Sol: 1.019E+005 (mg/L, EPIS uite WSKowwin v1.43 Estimate) Wat Sol: (User Entered) Wat Sol: (PhysProp DB exp value)

Values used to Generate ECOSAR Profile

--------------- ------------- ---------- Log Kow: -0.647 (EPISuite Kowwin v1.68 Estimate) Wat Sol: 1.019E+005 (mg/L, EPIS uite WSKowwin v1.43 Estimate)

Available Measured Data from ECOSAR Training Set

------------------------------------ ------------ No Data Available

--------------- ------------- ---------- ECOSAR v1.1 Class-sp ecific Estimations

Hydrazines

Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

========================= == ================== ======== ======

========== Hydrazines : Fish 96-hr LC50 19.921 Hydrazines : Daphnid 48-hr LC50 171.582 Hydrazines : Green Alg ae 96-hr EC50 4.107 Hydrazines : Fish ChV 2.414 ! Hydrazines : Daphnid ChV 19.439 ! Hydrazines : Green Algae ChV 0.893

========================= == ================== ======== ====== Neutral Organic SAR : Fish 96-hr LC50 45663.352 (Baseline Toxicity) : Daphnid 48-hr LC50 14620.531 : Green Algae 96-hr EC50 13355.061

: Fish ChV 3345.564 : Daphnid ChV 1003.074 : Green Algae ChV 836.764

### 56 ECOSAR Version 1.10 Results Page
CGA 215525 SMILES : O=C1(NN=C(CN1N)C)

CHEM :

CAS Num:
ChemID1:

MOL FOR: C4 H8 N4 O1

MOL WT : 128.13 Log Kow: -1.453 (EPISuite Kowwin v1.68 Estimate) Log Kow: (User Entered) Log Kow: (PhysProp DB exp value - for comparison only) Melt Pt: (User Entered for Wat Sol estimate) Melt Pt: (deg C, PhysProp DB exp value for Wat Sol estimate) Wat Sol: 7.978E+004 (mg/L, EPIS uite WSKowwin v1.43 Estimate) Wat Sol: (User Entered) Wat Sol: (PhysProp DB exp value)

-------------------- ------------------ Values used to Generate ECOSAR Profile

--------------- ------------- ---------- Log Kow: -1.453 (EPISuite Kowwin v1.68 Estimate) Wat Sol: 7.978E+004 (mg/L, EPIS uite WSKowwin v1.43 Estimate)

Available Measured Data from ECOSAR Training Set

No Data Available

--------------- ------------- ---------- ECOSAR v1.1 Class-sp ecific Estimations Hydrazines

Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

========================= == ================== ======== ======

========== Hydrazines : Fish 96-hr LC50 21.293 Hydrazines : Daphnid 48-hr LC50 223.29 Hydrazines : Green Alg ae 96-hr EC50 4.055 Hydrazines : Fish ChV 3.279 ! Hydrazines : Daphnid ChV 29.557 ! Hydrazines : Green Algae ChV 0.795

========================= == ================== ======== ====== Neutral Organic SAR : Fish 96-hr LC50 1.33e+005 * (Baseline Toxicity) : Daphnid 48-hr LC50 36520.914 : Green Algae 96-hr EC50 33205.391
: Fish ChV 8919.673 : Daphnid ChV 2203.103

### 57 : Green Algae ChV 1407.994 ECOSAR Version 1.10 Results PageCGA 300407 SMILES : c1cc(cnc1)C=O

CHEM :

CAS Num:
ChemID1:

MOL FOR: C6 H5 N1 O1

MOL WT : 107.11 Log Kow: 0.522 (EPISuite Kowwin v1.68 Estimate) Log Kow: (User Entered) Log Kow: 0.29 (PhysProp DB exp value - for comparison only) Melt Pt: (User Entered for Wat Sol estimate) Melt Pt: (deg C, PhysProp DB exp value for Wat Sol estimate) Wat Sol: 6.286E+004 (mg/L, EPIS uite WSKowwin v1.43 Estimate) Wat Sol: (User Entered) Wat Sol: (PhysProp DB exp value)

Values used to Generate ECOSAR Profile

--------------- ------------- ---------- Log Kow: 0.522 (EPISuite Kowwin v1.68 Estimate) Wat Sol: 6.286E+004 (mg/L, EPIS uite WSKowwin v1.43 Estimate)

Available Measured Data from ECOSAR Training Set

Measured CAS No Organism Durati on End Pt mg/L (ppm) Ecosar Class Reference

=========== ========== ========== ====== ==========

========================= == ========================= 000500-22-1 Fish 96-hr LC50 16.4 Aldehydes (Mono) DUL

--------------- ------------- ---------- ECOSAR v1.1 Class-sp ecific Estimations

--------------- ------------- ---------- Aldehydes (Mono)

Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

========================= == ================== ======== ======

========== Aldehydes (Mono) : Fish 96-hr LC50 36.381 Aldehydes (Mono) : Daphnid 48-hr LC50 122.696 Aldehydes (Mono) : Green Algae 96-hr EC50 133.972 Aldehydes (Mono) : Fish ChV 9.856 Aldehydes (Mono) : Daphnid ChV 13.540 ! Aldehydes (Mono) : Green Algae ChV 35.013 Aldehydes (Mono) : Fish (SW) 96-hr LC50 51.866 Aldehydes (Mono) : Fish (SW) ChV 4.927 !

Neutral Organic SAR : Fish 96-hr LC50 1871.123

### 58 (Baseline Toxicity) : Daphnid 48-hr LC50 747.808 : Green Algae 96-hr EC50 687.693
: Fish ChV 155.696 : Daphnid ChV 61.822 : Green Algae ChV 75.877

ECOSAR Version 1.10 Results Page
CGA 249257 C1(NCC(=NN1)C)=O

SMILES : O=C1(NCC(=NN1)C)

CHEM :

CAS Num:
ChemID1:

MOL FOR: C4 H7 N3 O1

MOL WT : 113.12 Log Kow: 0.292 (EPISuite Kowwin v1.68 Estimate) Log Kow: (User Entered) Log Kow: (PhysProp DB exp value - for comparison only) Melt Pt: (User Entered for Wat Sol estimate) Melt Pt: (deg C, PhysProp DB exp value for Wat Sol estimate) Wat Sol: 2931 (mg/L, EPISuite WSKowwin v1.43 Estimate) Wat Sol: (User Entered) Wat Sol: (PhysProp DB exp value)

Values used to Gene rate ECOSAR Profile

--------------- ------------- ---------- Log Kow: 0.292 (EPISuite Kowwin v1.68 Estimate) Wat Sol: 2931 (mg/L, EPISuite WSKowwin v1.43 Estimate) Available Measured Data from ECOSAR Training Set

No Data Available ECOSAR v1.1 Class-sp ecific Estimations

--------------- ------------- ---------- Hydrazines

Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

========================= == ================== ======== ======

========== Hydrazines : Fish 96-hr LC50 4.452 Hydrazines : Daphnid 48-hr LC50 30.499 Hydrazines : Green Algae 96-hr EC50 1.007 Hydrazines : Fish ChV 0.408 ! Hydrazines : Daphnid ChV 2.883 ! Hydrazines : Green Algae ChV 0.247

### 59 ========================= == ================== ======== ======

========== Neutral Organic SAR : Fish 96-hr LC50 3180.190 * (Baseline Toxicity) : Daphni d 48-hr LC50 1216.693 : Green Algae 96-hr EC50 1117.403

: Fish ChV 258.075 : Daphnid ChV 96.959 : Green Algae ChV 110.289

ECOSAR Version 1.10 Results Page
CGA-23199 SMILES : O=C1(NC(=O)(C(=NN1)C))

MOL FOR: C4 H5 N3 O2

MOL WT : 127.10 Log Kow: -0.116 (EPISuite Kowwin v1.68 Estimate) Log Kow: (User Entered) Log Kow: (PhysProp DB exp value - for comparison only) Melt Pt: (User Entered for Wat Sol estimate) Melt Pt: 211.00 (deg C, PhysPr op DB exp value for Wat Sol est) Wat Sol: 6279 (mg/L, EPISuite WSKowwin v1.43 Estimate) Wat Sol: (User Entered) Wat Sol: (PhysProp DB exp value)

Values used to Generate ECOSAR Profile Log Kow: -0.116 (EPISuite Kowwin v1.68 Estimate) Wat Sol: 6279 (mg/L, EPISuite WSKowwin v1.43 Estimate) Available Measured Data from ECOSAR Training Set

No Data Available ECOSAR v1.1 Class-sp ecific Estimations Hydrazines Carbonyl Ureas

Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

========================= == ================== ======== ======

========== Hydrazines : Fish 96-hr LC50 7.002 Hydrazines : Daphnid 48-hr LC50 52.978 Hydrazines : Green Algae 96-hr EC50 1.521 Hydrazines : Fish ChV 0.725 ! Hydrazines : Daphnid ChV 5.417 ! Hydrazines : Green Algae ChV 0.354

Carbonyl Ureas : Fish 96-hr LC50 235.604 Carbonyl Ureas : Daphnid 48-hr LC50 567.725

### 60 Carbonyl Ureas : Green Algae 96-hr EC50 0.010 Carbonyl Ureas : Fish ChV 1.699 Carbonyl Ureas : Daphnid ChV 7.066 Carbonyl Ureas : Green Algae ChV 0.003 Carbonyl Ureas : Fish (SW) 96-hr LC50 205.812 Carbonyl Ureas : Mysid (SW) 96-hr LC50 3657.087 Carbonyl Ureas : Fish (SW) ChV 4.694

========================= == ================== ======== ======

========== Neutral Organic SAR : Fish 96-hr LC50 8295.968 * (Baseline Toxicity) : Daphnid 48-hr LC50 2937.875 : Green Algae 96-hr EC50 2691.808

: Fish ChV 644.013 : Daphnid ChV 219.389 : Green Algae ChV 218.128

ECOSAR Version 1.10 Results Page
CGA 180777 SMILES : c1cc(cnc1)C(=O)(O)

CHEM :
CAS Num: ChemID1:

MOL FOR: C6 H5 N1 O2

MOL WT : 123.11 Log Kow: 0.686 (EPISuite Kowwin v1.68 Estimate) Log Kow: (User Entered) Log Kow: 0.36 (PhysProp DB exp value - for comparison only) Melt Pt: (User Entered for Wat Sol estimate) Melt Pt: 236.60 (deg C, PhysPr op DB exp value for Wat Sol est) Wat Sol: 1.006E+004 (mg/L, EPIS uite WSKowwin v1.43 Estimate) Wat Sol: (User Entered) Wat Sol: 1.8E+004 (mg/L, PhysProp DB exp value)

Values used to Gene rate ECOSAR Profile Log Kow: 0.686 (EPISuite Kowwin v1.68 Estimate) Wat Sol: 1.8E+004 (mg/L, PhysProp DB exp value)

Available Measured Data from ECOSAR Training Set

No Data Available

ECOSAR v1.1 Class-sp ecific Estimations

### 61 --------------- ------------- ---------- Neutral Organics-acid

Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

========================= == ================== ======== ======

==========

-- > Acid moeity found: Predicted values multiplied by 10

Neutral Organics-acid : Fish 96-hr LC50 15314.189 Neutral Organics-acid : Fish 14-day LC50 15006.738 Neutral Organics-acid : Daphnid 48-hr LC50 7713.472 Neutral Organics-acid : Green Al gae 96-hr EC50 5812.017 Neutral Organics-acid : Fish ChV 1297.290 Neutral Organics-acid : Daphni d ChV 535.852 Neutral Organics-acid : Green Algae ChV 694.339 Neutral Organics-acid : Fish (SW) 96-hr LC50 19128.344 * Neutral Organics-acid : Mysid 96-hr LC50 34624.660 * Neutral Organics-acid : Fish (SW) ChV 930.632 Neutral Organics-acid : Mysid (SW) ChV 4417.842 Neutral Organics-acid : Earthwor m 14-dayLC50 2929.361

Note: * = asterisk designates: Chemical may not be soluble enough to measure this predicted e ffect. If the effect level exceeds the water solubility by 10X, typically no effects at saturation (NES) are reported.

NOTE: ! = exclamation designates: Th e toxicity value was estimated through application of acut e-to-chronic ratios per methods outlined in the ECOSAR Methodology Do cument provided in the ECOSAR Help Menu.