### 1 

## UNITED STATES ENVIRONMENTAL PROTECTION AGENCY WASHINGTON, D.C. 20460

OFFICE OF CHEMCICAL SAFETY AND
POLLUTION PREVENTION



## Environmental Fate and Ecological Risk Assessment

Problem Formulation In Support of Registration Review of Prometryn

Prometryn : N,N'

- diisopropyl

- 6

- methylsulfanyl

- [1,3,5]triazine

- 2,4

- diamine (PC code: 080805, CAS No. 7287

- 19

- 6 )

Completed By: Mohammed Ruhman, PhD, Senior Agronomist Nicholas Mastrota, Wildlife Biologist
Environmental Risk Branch 5
Environmental Fate and Effects Division



## March 1 9 , 2013

N

N N S CH 3



## N N CH

H CH 3 

## CH 3



## CH

H H 3 

## C CH 3

### 2 

## Table of Contents

1. Introduction

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

................................ ................................ ................................ ............... 6
3. Conclusions from Previous Risk Assessments

................................ ................................ ..... 12
3.1. Ecological Risk Assessments

................................ ................................ ............. 12
3.2. Drinking Water Exposure Assessments

................................ ............................. 13
3.3. Clean Wat er Act Programs

................................ ................................ ................. 14
4. Environmental Fate and Transport

................................ ................................ ........................ 15
4.1. Transformation Profile/Products

................................ ................................ ........ 23
5.1. Effects of Prometryn to Aquatic Organisms

................................ ...................... 24
5.2. Effects of Prometryn to Terrestrial Organisms

................................ .................. 26
5.3. Expected Toxicity of Transformation Products

................................ ................. 28
5.4. Ecological Incidents

................................ ................................ ........................... 29

6. Exp osure Pathways of Concern

................................ ................................ ............................ 31

7. Analysis Plan

................................ ................................ ................................ ........................ 32
7.1 Stressor of Concern

................................ ................................ ............................ 32
7.2. Measures of Exposure

................................ ................................ ........................ 33
7.3. M easures of Effect

................................ ................................ ............................. 34
7.4. Endangered Species Assessments

................................ ................................ ...... 34
7.5. Endocrine Disruptor Screening Program

................................ ........................... 34
8. Preliminary Identification of Data Gaps

................................ ................................ ............... 36
8.2. Environmental Fate

................................ ................................ ............................ 36
8.3. Ecological Effects

................................ ................................ .............................. 37
9. References

................................ ................................ ................................ ............................. 42
10. APPENDICIES

................................ ................................ ................................ .................. 53 10.1 Appendix A: Prometryn Use and Usage Information

................................ ....... 54
10.1.1 Use Information

................................ ................................ ........................... 54 10.1.2. Usage Information

................................ ................................ ....................... 60 10.2 Appendix B: Prometryn Fate and Transport Properties

................................ ..... 63 10.3 Appendix C: Output from the SIP and STIR Models

................................ ........ 68 10.4 Appendix D: EIIS Incident Report

................................ ................................ ..... 71

### 3 

## List of Tables

Table 1 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weed (refer to abbreviations below): Caparol® 4L (Maximum rates)

............... 7
Table 2 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weeds (refer to abbreviations below): Suprend TM 

### Herbicide (Maximum rates) 8
Table 3 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weeds: C otton

- Pro ® 

### and Prometryne 4 L (Makhteshim Agan/Loveland Products/Winfield Solutions)

................................ ................................ .............................. 8 Table 4 Use sites and application information for prom etryn on crops other than cotton

.. 9 Table 5 Summary of Risk Concerns Identified for Prometryn in Previous
Assessments

................................ ................................ ................................ ..................... 13 Table 6 Physical/chemical parameters and fate properties in abiotic systems for
prometryn.

................................ ................................ ................................ ......................... 16
Table 7 Fate and transport properties of prometryn in biotic systems

............................ 16
Table 8 Extraction Procedures and Results

................................ ................................ ...... 19 Table 9. Summary of the Most Sensitive Endpoints from Aquatic Toxicity Studies for Prometryn

................................ ................................ ................................ .......................... 24 Table 10. Toxicity of P rometryn to Aquatic Plants

................................ ......................... 25 Table 11. Summary of the Most Sensitive Endpoints from Terrestrial Toxicity Studies for Prometryn

................................ ................................ ................................ .................... 27 Table 12. ECOSAR Predictions for Acute Toxicity of Prometryn and Hydroxypropazine to Aquatic Organisms.

................................ ................................ ................................ ...... 29 Table 13 Status of Environmental Fate Data Requirements for Prometryn

..................... 36 Table 14. Status of Data Requirements for Assessing the Ecological Effects of Prometryn to Aquatic Organisms

................................ ................................ ...................... 37 Table 15. Status of Data Requirements for Assessing the Ecological Effects of Prometryn to Terrestrial Organisms

................................ ................................ .................. 39

### 4 

## List of Figures

Figure 1 Prometryn degradation and formation of un

- extractable residues in viable soil/aquatic systems (data points from one aerobic soil and two aerobic aquatic systems (pond and river).

................................ ................................ ................................ ................ 21 Figure 2 Suggested degradation pathways for prometryn in varied laboratory and field
systems

................................ ................................ ................................ .............................. 23

### 5 

# 1. Introduction

Prometryn belongs to the triazine family of herbicides which includes atrazine, simazine, propazine, prometon, and ametryn among many others. The majority of the triazine
herbicides are based on s

- triazine structure containing two substituted amino groups (N

CH 3 

### - CH 3 

### ) with the 3 rd 

### carbon atom possessing one of the following groups: chloro (Cl) such as atrazine, methoxy (OCH 3 

### ) such as prometon, or thiomethyl (SCH 3 

### ) such as

p rometryn. Triazines belong to the group of herbicides which are applied to foliage (may be applied to soil as well) and are part of the category that apoplastically translocate s in the plant (systemic, capable of only upward movement) 1



### .

According to th e WSSA ( Weed Science Society of America) and HRAC (Herbicide Resistance Action Committee), the triazine family of herbicides is classified under the C1 (5) group (photo system II inhibitors) 2



### . The C1 (5) group of herbicides inhibit s photosynthesis by binding to the Q B

- binding niche on the D1 protein of the photosystem II complex in chloroplast thylakoid membranes. Herbicide binding at this protein location blocks electron transport from Q A to Q B and stops CO 2 

### fixation and production of ATP
and NADPH 2 which are all needed for plant growth. However, plant death occurs by other processes related to chains of reactions causing loss of chlorophyll and carotenoids and in leaky membranes which allow cells and cell organelles to dry and disin tegrate rapidly. In fish, the mode of action of prometryn toxicity is through neurological effects (Popova, 1976).

This document serves as a preliminary problem formulation for the upcoming ecological risk assessment for the Registration Review of promet ryn. It summarizes information currently available to the EPA on the environmental fate and ecological effects of prometryn. It also characterizes the registered uses of prometryn in the United States, and outlines the analysis plan for assessing ecolog ical risk posed by this herbicide in the
environment.

1 

### http://www.extension.purdue.edu/extmedia/ws/ws

- 23

- w.html

2 

### WSSA ( Weed Science Society of America) Classification of Herbicide Mechanism of Action (revised June 10, 2011): http://wssa.net/Weeds/Resistance/WSSA

- Mechanism

- of

Action.pdf And HRAC (Herbicide Resistance Action Committee) Classification of Herbicide
Mechanism of Action: http://wssa.net/Weeds/Resistance/HerbicideMOAClassification.pdf

### 6 

# 2. Use Characterization

Labeled Use

Prometryn is an herbicide used for control of broadleaf weeds and grasses on cotton and a variety of vegetable and herb crops. C rops include cotton, carrot, celeri ac, celery, dill, leafy petiole, okra, parsley, pigeon peas, and rhubarb . Prometryn can be applied either before (pre

- emergence) or after weeds emerge (post

- emergence). Timing of application may be pre

- plant (i.e., before planting the crop), pre

- emergenc e of weeds, post

emergence of weeds, or post

- transplanting (after transplanting for celery and fennel). In cotton, the chemical can be applied post

- emergence of weeds (directed to soil not the cotton plant), via c hemical h oe, and l ay

- b y for winter weed control. Prometryn may be applied by ground equipment to all crops, and by aircraft to cotton and pigeon pea. Prometryn may also be applied via an irrigation system (chemigation) to certain crops. Prometryn is the active ingredient in herbicide products formulated as a liquid concentrate or emulsifiable concentrate (EC). Major registered products containing
prometryn are:

• Caparol ® 

### 4L Herbicide (44.4% a.i, Registration No. 100

- 620, Syngenta)

• Suprend TM 

### Herbicide (79.3% a.i, Registration No. 100

- 1163, Syngenta). Suprend TM



### Herbicide al so contains 0.70% trifloxysulfuron

- sodium as a second active ingredient.

• Cotton

- Pro ® 

### (45.41% a.i, Registration No. 66222

- 116, Makhteshim Agan)

• Prometryne 4 L(44.0% a.i, Registration No. 66222

- 15, Makhteshim Agan)

• Prometryne 4 L(44.4% a.i, Registration No. 34704

- 692, Loveland Products); and

• Prometryne 4 L(44.4% a.i, Registration No. 9779

- 297, Winfield Solutions)

Furthermore , there are fifteen 24 C Special local need (SLN) labels for:

• Caparol 4L for control of w inter and early spring weeds in cotton in the States of AL, GA, MO, MS, SC, TN, and VA; for weed control in transplanted celery in CA; for herbicide application in/on dill and parsley in F L; and for control of weeds in the following seed crops: carrot, parsley, parsnip, and dill in WA;

• Prometryn 4L for weed control in on dill in WA ; and

• Prometryne 4L (Loveland) for control of weeds in fennel in CA and Vegetable Pro
for control of w eeds in d ill in WA and in celery in AZ. Additionally, EPA is currently reviewing a petition for a new food use on snap bean and
dill.

Use rates for a single application range from 0.5 to 3.2 lb a.i

. /A, and generally 1 to 3 applications are permitted during a growi ng season. Use information for application to the cotton crop contains many restrictions that are related to one or more of the following:

(1) Timing of application (i.e., pre

- plant, pre

- emergence, winter and early spring weed control, winter/fall weed control, pre

- and post

- emergence winter

### 7 application for bedded land to be planted cotton, post

- emergence directed,

c hemical h oe, and lay

- b y applications); (2) Soil characteristics (i.e., texture, presence of caliche layers, and presence of calcium carbonates); (3) Cotton plant height; (4) Weed size; (5) Use site location; and (6) Type of applications that might be permitted within a year.

Detailed use information for the appl ication parameters to all crops is presented in Appendix A (Page 54 ) 

### ; however, a summary for cotton use pattern is included in Tables 1
to 3 ; and a summary for lab eled use on all other crops is included in
Table 4

.

Table 1 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weed (refer to abbreviations below): Caparol ® 4 L (Maximum rates)

Type of Application Application Parameters: MSR and MYR (lb a.i/A); MNA; MAI (days); and Others

MSR MNA MYR MAI Notes & Restrictions
(A) Pre

- plant 4” incorporated 2.40 1 2.40 N/A No use or lower use rates depend on
location and soil texture

(B) Pre

- emergence (At or shortly after crop planting) 2.80 1 2.80 N/A No use or lower use rates depend on
location and soil texture. For NM , Apply either this application or the Pre

- plant 4” incorporated, Not both

(C) Pre

- emergence reduced rate application (At or shortly after crop planting) which is to be followed by application of other post emergence herbicides usually within a period of 30 or more days 1.00 1 1.00 N/A No use or lower use rates depend on
location and soil texture

(D) Winter and early spring weed control: * After bedding (from November 1 until 14 days before planting cotton); OR * After bedding (from January 1 until 30 days before planting cotton) 1.00 1 1.00 N/A Use only in AL, AR, LA, Mo, MS and TN : One of the applications, not both, and application may be made before or after weeds emerge preferably <2” high 0.75 1 0.75 N/A

(E) Winter/Fall weed control: * Winter application for bedded land to be planted cotton in the following spring OR * Fall application for bedded land to be planted cotton in the following spring 0.80 1 0.80 N/A Use only in TX Gulf Coast and Backlands
of TX: One of the applications, not both, and application may be made before weeds

emerge.

(F) Pre

- Or post

- emergence Winter application for bedded land to be planted cotton 1.6 1 1.60 N/A Use only in CA: pre

- emergence r ainfall or sprinkler irrigation is necessary. For post

emergence, Apply to weeds less than 2” tall. No use or lower rates depend on soil texture

(G) Post

- emergence directed: * Minimum cotton plant Height = 3

- 6” and maximum weed Height= <1”; * Minimum cotton plant Height = >6” and maximum weed 0.5 1 0.5 N/A Use only in AR, LA, MO, MS, TN and TX

0.7 1 0.7 N/A Use in all other cotton regions

### 8 Table 2 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weed s (refer to abbreviations below): Suprend TM 

### Herbicide (Maximum rates)

Table 3 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weeds: C otton

- Pro ® 

### and Prometryn e 4 L (Makhteshim Agan/Loveland Products/Winfield Solutions) Height= <2” (H) Chemical Hoe (emerged weeds only): * Minimum cotton plant Height = 3

- 6”

* Minimum cotton plant Height = 3

- 6” and maximum weed Height= <1” 0.5 3 1.5 NS * In cotton 3

- 6 inches tall, be extremely careful to avoid spray contact with cotton leaves by applying Caparol 4L with a precision applicator equipped with fenders or shields, * In cotton <10” tall, apply only if cotton is
bedded or flat

- planted. 0.7 3 2.1 NS

(I) Lay

- By (Cotton at least 12” high) 1.6 2 3.2 NS No use or lower use rates depend on location, soil texture, and/or weed size

Abbreviations: N/A= Not applicable; NS: Not specified, the registrant is requested to supply the information and include it in the label;
MSR= Maximum Single Rate; MNA= Maximum number of applications; MYR= Maximum yearly rate (seasonal) ; MAI= Minimum application intervals

Type of Application Application Parameters: MSR and MYR (lb a.i/A); MNA; MAI (days); and Others

MSR MNA MYR MAI Notes & Restrictions

Post

- emergence directed application on picker and pima cotton varieties only; When cotton > 6” tall and Weeds are actively growing with size <6” (Application rate varies with weed type/size to be controlled) 1.19 1 + Or
4+ 2.14
Or
5.15 (See Text) 14 Use only in: AL, AR, AZ, CA, FL, GA, KS, KY, LA, MS, NM (certain counties), NC, SC, TN, VA , the boot heel area of MO , and portions of OK and TX (east of State Highway 83 and east of 1

- 35) including/excluding the high plains region
of West TX and OK

. Do not use in: Rio Grande Valley of TX, the Coachella Valley of AZ and CA , and sand and loamy sa nd soils in AZ and CA

. Do not apply aerially

Abbreviations: N/A= Not applicable; NS: Not specified, the registrant is requested to supply the information and include it in the label;
MSR= Maximum Single Rate; MNA= Maximum number of applications; MYR= Maximum yearly rate; ; MAI= Minimum application intervals; Numbers in RED/Bold = Calculated values from information provided in the label; noting that 1 + or 4+ means that one more application, with lower application rate, may be used; for example: The to tal for 4applications= 4 x 1.19= 4.76 lb a.i/A and because 5.15 lbs a.i/A is permitted a 5 th application may be used at a rate= 5.15

- 4.76= 0.39 lbs ai/A.

Type of Application (Pesticide Formulation Name) Application Parameters: MSR and MYR (lb a.i/A); MNA; MAI (days); and Others

MSR MNA MYR MAI Notes & Restrictions
(A) Pre

- plant (before planting cotton) (Cotton Pro & Prometryn 4L) 2.8 1 2.8 N/A No use or lower use rates depend on
location and soil texture. Can be aerially applied

### 9 Table 4 Use sites and application information for prometryn on crops other than cotton (Maximum rates /Ground spray for all crops except Pigeon Peas “ground/aerial;
C hemigation for applications on celeriac, celery/leafy petiole crop group s ) (B) Pre

- plant 4” incorporated (Cotton Pro; Prometryn 4 L; Prometryne 4 L/Loveland & Winfield ) 2.4 1 2.4 N/A No use or lower use rates depend on
location and soil texture. For NM , Apply either this application or the Pre

- plant 4” incorporated, Not both. Can be aerially applied

(C) Pre

- emergence (at planting or shortly after planting) (Cotton Pro & Prometryn 4 L; Prometryne 4 L/Loveland
& Winfield ) 2.4 1 2.4 N/A Lower use rates depend on location and soil

texture. Can be aerially applied. Sand or loamy sand, shallow soils with caliche sub

soils or in areas with caliche outcroppings

(D) Post

- emergence Directed: Chemical Hoe ( C otton

- Pro; Prometryn 4L; Prometryne 4 L/Loveland & Winfield ) 0.65 3 2.0 NS Lower use rates depend on location and soil

texture. Cannot be aerially applied.

(E) Post

- emergence Directed: Lay

- By (emerged/germinating weeds) ( C otton

- Pro & Prometryn 4L; Prometryne 4 L/Loveland & Winfield ) 1.6 1 1.6 N/A No use or lower use rates depend on
location and soil texture. Cannot be aerially applied (F) Winter Weed Control ( C otton

- Pro) 2.0 1 2.0 N/A Lower use rates depend on location and soil

texture.
(G) Winter Weed Control (Prometryn 4L; Prometryne 4
L/Loveland & Winfield ) 2.0 1 2.0 N/A Lower use rates depend on location and soil

texture.

Abbreviations: N/A= Not applicable; NS: Not specified, the registrant is requested to supply the information and include it in the label;
MSR= Maximum Single Rate; MNA= Maximum number of applications; MYR= Maximum yearly rate; ; MAI= Minimum application
intervals

Crop: Type of Application Application Parameters: MSR and MYR (lb a.i/A); MNA; MAI (days); and Others

MSR MNA MYR MAI Product(s), Notes & Restrictions

Carrot: Pre

- emergence of crop Plus Post

emergence of crop through the 6 leaf stage 2.0
Plus
1.0 1

2 4.0 N/ N Caparol 4L, and Prometryn 4L ;

Celeriac / Transplant ed: A fter the crop has 6

- 8
leaves O R Post

- emergence up to 6

- 8 leaf stage 2.0 1 2 .0 N/A Caparol 4L

, Prometryn 4L

,

Celery / Seedbeds : Application (1) 0.8 1 0.8 N/A Caparol 4L, Prometryn 4L

, Cotton

- Pro, and Prometryne 4L (Agri

- solutions /Love land ); FL only; Lower rates for coarse textured soils Celery/ Direct seeded crop: Pre crop emergence/ shortly after planting O R Post crop emergence @
2

- 5 true leaves crop stage and weeds<2” tall 1.6 1 1.60 N/A Caparol 4L, P rometryn 4L, Cotton

- Pro, and

Prom etryne 4L (Agri

- solutions/Love land) ; CA only; Lower rates for coarse textured soils

Celery/ Transplanted crop: Pre

- transplant: Up to 21 days prior to transplant (1) ; O R Split Pre & post

transplant: Pre

- transplant as above plus post

transplant during the 2

- 6 week period after transplanting and weeds <2” ta ll O R Post

transplant during the 2

- 6 week period after transplanting and weeds <2” tall 3.2
O R
1.6 1

2 3.2 N/A
Or
N/N Prometryne 4L (Loveland ) ; Maximum rate is for HI; lower use rates depend on location (Lower rates for CA, FL, MI, and WI) soil texture (lower rates for coarse textured/low
OM soils

### 10 Celery/Transplanted crop: Post

- transplant during
the 2

- 6 week period after transplanting and weeds
<2” tall 3.2 1 3.2 N/A Maximum rate is for HI; lower use rates depend on location (Lower rates for CA, TX, FL, MI, OH and WI) and soil texture (lower
rates for coarse textured/low OM soils

Celery Group/Chinese celery and Florence fennel : Seedbeds: Application 0.8 1 0.8 N/A Caparol 4L and Prometryn 4L

Celery Group/Chinese celery and Florence fennel: Pre crop emergenc e/ at or shortly after planting
O R Post crop emergence @ 2

- 5 true leaves crop stage and weeds<2” tall 1.6 1 1.6 N/A Caparol 4L and Prometryn 4L; CA only;
Lower rates for coarse textured soils and is not to be used on sand or loamy sand soils

Celery Group/Chinese celery and Florence fennel:

Post

- transplant during the 2

- 6 week period after transplanting O R this application may be applied once or split into two) 2.0
O R
1.0 1

2 2.0 N/A

NS Caparol 4L and Prometryn 4L; Maximum rate is for (AZ, CA, TX, MI, OH and WI); lower use rates depend on location (Lower rates for FL) and soil texture (sandy or muck soils)

Cilantro : Post

- planting /Pre

- emergence of crop 1.6 1 1.6 N/A Prometryn 4L and Caparol 4L and Prometryn
4L Lower rate of 1.0 for coarse textured soil was only specified in Caparol 4L label

Dill: Pre

- O R post

- emergence before weeds 2” tall 1.6 1 1.60 N/A Prometryne 4L (Loveland); Use on sand or loamy sand soils may cause crop injury

Leafy Petiole 1 : Seedbed After the crop has 2

- 5 true
leaves and 7 days after seedbed cover is removed 0.8 1 0.8 N/A Prometryn 4L; FL only

Leafy Petiole 1 : Direct seeded crop pre O R post emergence after the crop has 2

- 5 true leaves 1.6 1 1.60 N/A Prometryn 4L; CA and AZ only; Lower rate
for coarse textured soils and no use on sand and loamy sand soils

Okra : Pre

- emergence O R Pre

- emergence & post emergence directed 1.5
O R
0.75 1

2 1.5 N/A Caparol 4L and Prometryn 4L; Pre

emergence= after planting before crop

emergence; Post directed= when okra plants

are at 7

- 9 leaf & weeds 2” tall

Parsley: Pre

- emergence, after planting / before crop

emerges 2.0 1 2.0 N/A Caparol 4L, Prometryn 4L and Prometryne 4L (Loveland); CA only; Lower rate of 1.0 for coarse textured soils; no used on sandy & loamy sand soils

Parsley: After planting 0.5 3 1.5 Refer to
last
column Caparol 4L; Only on Fine textured/high OM
soils as follows: 1 st application 14 days after planting; 2 nd application 30

- day prior to harvest; 3 rd application to re

- growth “after cutting” up to 30 days prior to the second cutting

Pigeon Peas (Puerto Rico Only): Pre

- emergence of weeds/crop 3.0 1 3.0 N/A Caparol 4L, Prometryn 4L; Apply at planting or immediately after planting before crop/weeds emerge; Lower rate of 2.0 for loam soils; no used on sandy & loamy sand
soils

### 11 Registrants are requested to check the detailed/summary information provided in Appendix A (Page 54 ) and in Table 1 to 3 , above

, for accuracy. EFED noted those
lab els for C otton

- Pro ® 

### ; Prometryn 4 L (Makhteshim Agan); Prometryne 4 L (Loveland Products), and Prometryne 4 L (Winfield Solutions) contained sufficient application details, including non

- use sites. However, the labels lack the following important
parameters that are requested to be included in future labels. The requested parameters

are:

(1) The maximum yearly rate for each application type, i.e., the nine application types
stated in the 1 st 

### column of Table 1

, above

, use site such as “ TX” and/or soil (e.g., sandy loam soil)/cotton plant height (e.g., cotton 3

- 6”) /weed size (e.g., Weeds <2”) ;

(2) Which types of applications m ay be combined within the year; a nd

(3) Missing information (marked by NS or ?) which are necessary for exposure modeling
and for inclusion in future labels.

For Suprend TM 

### Herbicide, t he label states “ Do not exceed a total of 2.7 l bs. / A of Suprend per season from all applications ” (that is 2.14 lbs a.i “prometryn”/A) and continue to state
“Do not exceed 5.15 l bs. active ingredient of prometryn per acre per season resulting from all applications of Suprend TM 

### or Caparol 4L, or other prometryn containing products”. The registrant is requested to modify the statements above to clarify if the seasonal rate or the ye arly rate is 2.14 lbs a.i of prometryn/A/season “assume: year” or
5.15 l bs a.i of prometryn/A/season “assume: year”.

In addition, registrants are requested to check the information provided in
Table 4

, above, for accuracy and for providing requested missing information necessary for exposure modeling and for inclusion in future labels for these products. Rhubarb: Dormant established crop 2.0 1 2.0 N/A Caparol 4L; Lower rate of 1.6 for coarse
textured soils

Abbreviations: N/A= Not applicable; NS: Not specified, the registrant is requested to supply the information and include it in the label;
MSR= Maximum Single Rate; MNA= Maximum number of applications; MYR= Maximum yearly (seasonal) rate; MAI= Minimum application intervals; N/N= This informati on is not necessary as it can be estimated from the crop profile.

1 Leafy Petiole = Leafy Petiole= cardoon, celery, Chinese celery, celtuce, Florence fennel, rhubarb, and Swiss chard

### 12 Usage

The Biological and Economic Analysis Division (BEAD) completed a Screening Level Usage Analysis (SLUA) report for prometryn on September 10, 2012 ( Appendix A, Page 60 )

. According to this report, the greatest amount of use of prometryn is on cotton,
with an estimated 800,000 lb a.i. applied in the United States annually. On average, approximately 10% of the cotton crop is treated with prometryn each year. Prometryn is also used widely on celery, with approximately 40,000 lb a.i. applied annually. Approx imately 85% of the celery crop is treated with prometryn each year. The other most significant uses are on carrots (3,000 lb a.i./year) and fallow ground (3,000 lb a.i./year).



# 3. Conclusions from Previous Risk Assessments

3.1. Ecological Risk Assessments

The Ag ency has conducted multiple ecological risk assessments on prometryn that serve as a basis for this scoping document, including ecological risk assessments for a Re

registration Eligibility Decision (USEPA 1996) 3 

### , pesticide effects determination for the
Ca lifornia Red

- legged Frog (June, 2009) 4 

### , and a section 3 registration of new uses on crop subgroup 4B (August, 2009). 5 

### The primary risk issues that have been identified are for terrestrial and aquatic plants, which is consistent with its use as an herbicid e. However, risk quotients have also exceeded concern levels for terrestrial and aquatic animals as well. These assessments are briefly summarized below.

The most recent, comprehensive assessment conducted for prometryn was for the new use registration of crops in crop subgroup 4B (leafy petioles), which was completed in August of 2009. For these uses, risk was identified for both aquatic and terrestrial non

target plants. Risk was identified for chronic effects to fish for some uses. Risk of acute

to xicity to fish and aquatic invertebrates was determined to not exceed the EPA’s level of concern (LOC) for non

- endangered species (non

- listed species) , but exceed ed the LOC for possible adverse effects to federally threatened and endangered species (listed species). Risk was identified to terrestrial vertebrates (birds, mammals, reptiles, and terrestrial phases of amphibians) because of chronic toxicity. Risk for acute toxicity to terrestrial vertebrates was not great enough to exceed the LOC for non

- list ed species, but in some cases exceeded the LOC for possible adverse effects to listed species.

Similar conclusions were reached in the 1996 Re

- registration Eligibility Decision (RED) (USEPA 1996). The environmental fate assessment characterized prometryn as highly persistent in soil and water, and highly mobile in soil. It has low volatility and a low

3 http://www.regulations.gov/#!documentDetail ;D=EPA

- HQ

- OPP

- 2009

- 0081

- 0087 )
4 Risks of Prometryn Use to Federally Threatened California Red

- Legged Frog ( Rana aurora draytonii ). June 17, 2009 URL: http://www.epa .gov/espp/litstatus/effects/redleg

- frog/prometryn/analysis.pdf

5 Ecological Risk Assessment for Section 3 New Use Registration of Prometryn (crop subgroup 4B: leafy petioles: cardon, celery, Chinese celery, clettuce, fennel, rhubarb, Swiss chard, carrot, celeriac, cilantro, okra, and parsley. August, 2009 DP Barcodes: 357096/99, 357334/35.

### 13 propensity to bio

- accumulate. Risk of acute toxicity to fish and aquatic invertebrates was
determined to not exceed the LOC for non

- listed species, but ex ceed the LOC for possible adverse effects to listed species of saltwater fish and invertebrates. Uses of prometryn were predicted to pose risk to birds because of chronic reproductive effects. This assessment was based on an older avian reproduction stud y with the mallard ( MRID
410359 0 1) and did not consider information on chronic toxicity to the bobwhite provided by a newer avian reproduction study (MRID 44556801). For mammals, some acute RQs exceeded the LOC for possible adverse acute effects to listed species.

In these past assessments, chronic risk to birds w as based on avian reproduction studies which yielded indeterminate effects for the mallard (MRID 41035901, NOAEC = 500 mg a.i./kg

- diet, LOAEC > 500 mg a.i./kg

- diet) and for the northern bobwhit e (MRID 44556801, NOAEC = 600 mg a.i./kg

- diet, LOAEC > 600 mg a.i./kg

- diet). These studies did not find any treatment

- related adverse effect on avian reproduction at any of the test levels. Since these studies did not test above 500 mg a.i./kg

- diet for m allards or above 600 mg a.i./kg

- diet for bobwhite, the risk of chronic toxicity above these level s is not known. Additional chronic toxicity testing would be needed to predict if all uses of prometryn would or would not cause chronic risk to birds.

In the se past assessments, r isk was also determined for both aquatic and terrestrial plants. General conclusions from previous assessment s are summarized in Table 5



### .

Table 5 Summary of Risk Concerns Identified for Prometryn in Previous Assessments

Birds Mammals Terrestrial
Plants Terrestrial
Invertebrates Fish Aquatic

Inverts Aquatic
Plants

Uncertain 1 

### √ 2 

### √ LOCs not exceeded 

### √ 3 

### √ 3 

### √

1 Acute risk to birds is low, but chronic risk to birds is uncertain because avian reproduction studies did not test at high enough levels to assess chronic risk for all uses of prometryn.
2 Risk to mammals is based on sub

- lethal effects caused by chronic exposure. 3 Risk quotients did not exceed the LOC for risk to non

- listed species, but in some cases did exceed the LOC for potential to harm some listed species. √ = at least one LOC has been exceeded

.



## 3.2. Drinking Water Exposure Assessments

A drinking water exposure assessment for proposed new uses on carrots, okra, parsley, cilantro, celeriac, and leafy petioles was conducted for prometryn in 2009 (USEPA, 2009). This referenced assessment addressed concentrations of parent only, and no degr adates were included. No reference was made to a decision by the EPA committee on the residues of concern; it appears that the committee did not consider this issue. Exposure estimates of prometryn parent only from currently labeled uses that produce
maxim um exposure (carrots) were 377.4 μg/L (1

- in

- 10

- year peak) and 157.9 μg/L (1

- in

10

- year annual mean); no concentration was reported for the 30

- year mean for surface water, and 23.2 μg/L was reported for ground water. HED and EFED preliminarily
considered a meeting for ROCKS (Residue of Concern Knowledgebase Subcommittee),

### 14 however, it was resolved that the residues of concern for prometryn are parent +major degradate hydroxypropazine (GS

- 11526).



## 3.3. Clean Water Act Programs

Concerning prometryn and the Clean Water Act Programs, the following are stated:

• California has identified 10 miles of the Salt Slough (upstream from the confluence with the San Joaquin River) as being impaired from contamination with prometryn. 6 

### This is the only water body that has been listed by the state as impaired by prometryn under Section 303(d) of the Clean Water Act : http://ofmpub.epa.gov/tmdl_waters10/attains_state.cause_detail_303d?p_cause_group_id=8 85&p_state=CA&p_cycle=2010&p_report_type=



### • The Total Maximum Daily Load (TMDL) criteria have not been developed for
prometryn as n o listings were found 7 

### at URL: http://iaspub.epa.gov/pls/waters/f?p=ASKWATERS:V_WO_APPROVED_TMDLS: 14484056936224::::P4_OWNER:ATTAINS

• Aquatic benchmarks have been estab lished for prometryn. These benchmarks were
based on the 1996 RED document and are can be found at URL: http://www.epa.gov/oppefed1/ecorisk_ders/aquatic_life_benchmark.htm

.

Section 5 .1 of this document identified a more sensitive aquatic endpoint for aquatic invertebrates based on findings from a published study (Marchini, 1988). This study yielded an LC 50 

### for Daphnia magna of 9.70 mg a.i./L, thereby reducing the acute aqua tic benchmark to 4850 μg a.i./L. The other aquatic bench marks remain unchanged.

Finally, it is noted that no Office of Water Aquatic Life Criteria are established for this chemical. Any data submitted or otherwise located as part of the R egistration R ev iew process may be used to update aquatic life benchmarks if applicable.

6 http://ofmpub.epa.gov/waters10/attains_waterbody.control?p_list_id=CAR5412000019990126155034&p_r eport_type=T&p_cycle=2010

7 after Choosing: 303(d) Listing & TMDL Infor mation303(d) Listing & TMDL Information ; then:
Detailed information from Approved TMDL Documents under Pollutant Name (Prometryn name was not found)

### 15 

# 4. Environmental Fate and Transport

Prometryn [N,N'

- diisopropyl

- 6

- rnethyIsulfanyl

- [1,3,5]triazine

- 2,4

- diamine; PC code:
80805 and CAS No. 7287

- 19

- 6] is expected to be soluble, semi vo latile, and moderately hydrophobic. The chemical is stable to laboratory hydrolysis, aqueous and on soil photolysis. Prometryn may be considered relatively highly persistent in soil and aquatic systems under aerobic conditions. It can also be considered st able under anaerobic soil/aquatic conditions. The major degradate of prometryn is GS

- 11526 with minor degradates including GS

- 11354, GS

- 16141, and GS

- 1779. The chemical shows similar persistence in the field.

(1) Physical/Chemical Parameters and Fate Properti es in Abiotic Systems

Prometryn is characterized by a water solubility of 33 ppm with one order of magnitude higher solubility in organic liquids. The expected concentration in the top 6” of the soil is 2.0 ppm following maximum single application of up to 4 lbs a.i/A, therefore, applied chemical is expected to be soluble within the expected range of moisture present in cropped agricultural soils. This means that the applied chemical will be soluble and ready to move via leaching and run

- off.

The vapor p ressure of prometryn indicates that it is a semi

- volatile (VP= 1. 24 x10 - 6 

### ) and is expected to volatil ize from dry surfaces ; however volatility is expected to be much lower from water and wet soils (Henry’s Law Constant= 1.19 x10 - 8 

### atm m 3 

### mol - 1 

### ). The magnitude of transport via volatility depends on prometryn’s ability to mobilize into air and its eventual removal through wet and dry deposition of gases/particles and photochemical reactions in the atmosphere (t 1⁄2 in air= 0.3 days)

. Very recently (2008

- 2009) the US Geological Survey (USGS) has reported data on the presence of pesticides in rain and wet deposition in four USA agricultural watersheds. Among other pesticides, prometryn was detected in rain and wet deposition in California, Maryland, I ndiana, and Nebraska (Vogel et al., 2008). The o ctanol: water partition coefficient 

### for prometryn suggests that it is moderately hydrophobic; however, a fish bio

- concentration study found that prometryn bio

- concentrates very little in fish (whole fish BCF = 85x, MRID 41022701).

A summary of the p hysical and chemical properties of prometryn is presented in

Table 6

. Finally, prometryn is stable to abiotic processes : hydrolysis, photolysis on soil, and direct photolysis (

Table 6 ). No guideline studies were submitted for prometryn in order to evaluate the possible role of indirect photolysis; however, others reported that the chemical is affected

### 16 by this process in na tural waters (Connell et al. , 2004; Cessna, 2008; Kontantinous, 2001; and Garbini, 2007).

Table 6 Physical/chemical parameters and fate properties in abiotic systems for
prometryn.

Parameter Value Source MRID (Classification)



### Physical/chemical properties

Molecular mass (molecular formula) 241.4 g/mol (C 10 H 19 N 5 S) Registrant Data

Solubility (25 ° C) In Water: 33 mg/L; Acetone: 300 g/L; Ethanol 140 g/L; Toluene 200 g/L;

n

- Hexane 6.3 g/L and n

- Octanol 110 g/L 001483

- 34

Vapor pressure (25°C) 1.24 x 10

- 6 torr 443396

- 01

Henry’s Law Constant (25°C) 1.19 x10 - 8 atm m 3 mol - 1 Calculated from Vapor Pressure And Solubility

Octanol: water partition coefficient (Log K OW and K OW ) Log K OW = 3.46; K OW = 2,884 001483

- 34


### Fate properties in abiotic systems

Hydrolysis half

- life (22 ° C) Stable at pH 5, 7, and 9 405737

- 04 (Acceptable)

Aqueous photolysis half

- life (25 ° C) Stable 405737

- 05 (Acceptable)

Photolysis on soil 1 half

- life (25 ° C) Stable 405737

- 06 (Acceptable)

t 1⁄2 in air (days) 0.28 (relatively rapid atmospheric oxidation) EPI Suite 8

1 Sandy loam soil:70% sand, 27% silt, 3% clay, 0.94% organic matter, pH 5.2, and CEC 6.79 meq/100 g



### (2) Fate and Transport Properties in Laboratory and Field Biotic Systems

Detailed laboratory/field fate and transport properties of prometryn are presented in Appendix B, page 63 ; however, a summary for these properties are included in Table 7

.

Table 7 Fate and transport properties of prometryn in biotic systems

8 http://www.epa.gov/opptintr/exposure/pubs/episuitedl.htm Property System Characteristics Degradation Products (% of Applied) Value Reference (MRID)

Classification

Aerobic Soil Metabolism Loamy sand soil Major (MAJ): GS

- 11526 (max. 27% and
Non

- extractable residues (NER) (max. 31%)
both @ termination (360 days) Minor (MIN): GS

- 11354 declined; and CO 2 257 days 001483

- 38

Acceptable

### 17 (a) Fate Properties

Laboratory data suggest that the chemical is expected to slowly dissipate, in soil and aquatic systems in the environment, principally by biologically induced hydrolysis and oxidation. However, biotransformation does not include mineralization to CO 2 

### , at least under the conditions tested (fate data with other s

- triazine herbicides also support that the ring structure is recalcitrant to degradation under the vast majority of field conditions). Prometryn appears to degrade slowly in aerobic soil (t1⁄2= 257 days; tested in only one soil) and in aerobic aquatic systems (90 th 

### percentile t1⁄2= 367). No degradation is expected Anaerobic Soil Metabolism Sandy loam soil No degradation products formed Stable 411559

- 01 Acceptable

Aerobic Aquatic Metabolism (total system) River System:
Water/Sediment MAJ: GS

- 11526 (max. 18 % and NER (max.
26 %) both @ termination (268days)
MIN: GS

- 11354 declined; GS

- 16141 declined;
GS

- 17794 no decline; and CO 2 236 days 485416

- 03

Under Review 2

Aerobic Aquatic Metabolism (total system) Pond System:
Water/Sediment MAJ: GS

- 11526 (max. 18 % and NER (max.
35 %) both @ termination (268days)
MIN: GS

- 11354 declined; GS

- 16141 declined;
GS

- 17794 no decline; and CO 2 110 days 485416

- 03

Under Review 1

Terrestrial Field Dissipation 2 CA Sandy loam
Planted cotton Degradation in the Top 30 cm:
MAJ: GS

- 11526 (max. 15 to 31% declined to
no detection to 2%
MIN: GS

- 11354 (max. 1 to 4% declined to no detection to 1%; Degradates GS

- 16141 &
GS

- 1779 were tracked but not detected Leaching
* Parent : Show limited leaching to the 15

- 60 cm layer (low to high detection frequency at
max concentrations of 2

- 5%) and very limited leaching to the 60

- 120 cm layer (low detection frequency at max concentrations of 1

- 5%)
* GS

- 11526: Shows relatively more leaching to
the 15

- 60 cm layer than parent and very limited leaching to the 60

- 120 cm la yer; * GS

- 11354: Was not detected below 30 cm 103 415464

- 01/
422539

- 03 Acceptable

CA Sandy loam

Bare

- ground 71 415464

- 02/
422539

- 04 Acceptable

TX Silt loam
Planted cotton 86 415464

- 03/
422539

- 01 Acceptable

TX Silt loam

Bare

- ground 70 415464

- 04/
422539

- 02 Acceptable

Soil

- Water Partition Coefficients (K FOC ) L/Kg Agricultural sand Parent: 245 GS

- 11354: 174, and GS

- 11526: 186

418759

- 01/03

Acceptable Loamy sand Parent: 169 GS

- 11354: 86, and GS

- 11526: 85

Silt Loam Parent: 116 GS

- 11354: 72, and GS

- 11526: 84

Silty clay loam Parent: 448 GS

- 11354: 210, and GS

- 11526: 1,044

Laboratory Volatility @ 25 o C Sandy soil Minimal volatility (0.99% volatilized in 30 days) 418759

- 06 Acceptable

Fish bio

- concentration Bluegill sunfish BCFs: 85x (whole fish); 54x (fillet); and 110x (viscera); 73% depuration in 14 days 410227

- 01 Acceptable

1 Under Review : Formal review underway.

2 It is noted that field dissipation data was corrected for recoveries, and that recoveries were low in addition the sampling techniques may have cause detection of parent at lower depths and the analytical method for quantification of GS

- 11526 was unreliab le.

### 18 in anaerobic systems as it was stable in anaerobic soil system ( Table 7 ). Fate data also reveal a unique property for prometryn residues that is expected to affect the risk assessment. This property is the formation of significant amounts of un

- extractable
residues t hat were not identified (un

- extractable resides in the range of 26 to 35%). Based on the lines of evidence presented below, inclusion of un

- extractable residues in half

- life estimates will cause an estimation of longer aerobic soil/aquatic systems half

- liv es than these presented in Table 7

.

Field data show that prometryn is relatively persistent in both planted and bare soil. Dissipation half

- lives fo r the top soil, at the four sites, ranged from 86

- 103 days in cotton planted fields and 70

- 71 days in the same, but bare, fields ( Table 7 ). Relatively lower field dissipation half

- lives compared to laboratory aerobic soil degradation half

- lives is probably a reflection of leaching in addition to degradation. Field degradation resulted in the same degradation products observed in the laboratory which inc luded the major degradate GS

- 11526 (hydroxypropazine, max. 15 to 31% declined to no detection to 2%)
and GS

- 11354 (de

- ethylametryn, max. 1 to 4%) ; both degradates declined by the end of the 540 days into no detection to 1%

- 2%. Degradates GS

- 16141 and GS

- 17 79 were
tracked but not detected in the field.

(b) Transport Properties

Laboratory data on prometryn suggest moderate mobility (K
oc 

### range from 116 to 448 L/Kg). Additionally, the two tested degradates of prometryn (GS

- 11354 and GS

- 11526) are expected to be mobile to moderately mobile (K
oc 

### range from 72 to 1,044 L/Kg) ( Table 7 ). In laboratory column leaching studies, prometryn shows low mobility than that suggested by the adsorption/desorption data stated above. Low mobility of prometryn was suggested by Field data which showed lim ited leaching of prometryn to the 15

- 60 cm soil layer and very limited leaching to the 60

- 120 cm layer. In contrast, field data for the major degradate of GS

- 11526 s hows relatively more leaching to the 15

- 60 cm layer than parent, but very limited leaching to the 60

- 120 cm layer. GS

- 11354 degradate was not detected below the top 30 cm of the soil.

It appears that different conclusions may be drawn from Adsorption/desorption data (moderate mobility) ver sus column leaching/field data (low mobility). This may have resulted from aging of the residues in leaching studies but could be explained for field studies. It may be help if reasoning or data is submitted to explain the discrepancies between lab and field transport data. Meanwhile, EFED will base its conclus ions on adsorption/desorption data which indicate that prometryn and degradates are expected to be transported into surface and ground waters. Leaching to ground water is expected to occur in vulnerable aquifers, such as those with coarse

- textured soils l ow in organic

matter.

Furthermore, a laboratory volatility study showed volatility was minimal (0.99% prometryn volatilized by 30 days) suggesting that volatility is not a significant route of dissipation for prometryn. Finally, data obtained on fish bio

- concentration indicate low
bio

- concentration potential for prometryn ( Table 7 )

### 19 Field data show limited leaching of prometryn to the 15

- 60 cm soil layer and very limited leaching to the 60

- 120 cm layer. In contrast, prometryn degradate GS

- 11526 s hows relatively more leaching to the 15

- 60 cm layer than parent, but very limited leaching to
the 60

- 120 cm layer. GS

- 11354 degradate was not detected below the top 30 cm of the
soil.

(3) 

### Un

- extractable Residues

The m aximum amount of un

- extractable bound resides in an aerobic soil system was 31% of the applied radioactivity

, and it was in the range of 26 to 35% of the applied radioactivity in two aerobic a quatic systems. These residues increased gradually and reached maximums at termination of the experiments with no apparent decline. In this problem formulation, un

- extractable residues were considered as part of residues of interest along with two prometry n degradates. Based on the analyses stated hereunder, it
was decided that un

- extractable residues should be considered as part of the stressor. The analysis of this problem included examination of the data to answer the following question:

Was there an ad equate attempt for extracting the residues

, and what was the relationship between the degradation profile of the chemical and the formation of un

- extracted
residues?

Solvent (methanol or acetone)/water followed by a Soxhlet/solvent were the main
extractio n steps used for extracting prometryn and residues from soil and sediments.
Table 8 contains a summary of these extraction steps as reported in submitt ed studies.

Table 8 Extraction Procedures and Results

Study MRID 1 st

Extraction 2 nd

Extraction Yield 1 Notes Un

- extractable Residues Max. (% of Applied) Time for Max.
Occurrence

Viable Aerobic Soil System

001483

- 38 Methanol/ Water (8/2) Methanol Soxhlet (all samples) N/D 1 st and 2 nd

Extracts were
combined and
the total was analyzed 30.8% 2

Experimental
Termination Viable Anaerobic Soil System 3.7% 3

Sterile Aerobic Soil System 3.4% 4

Viable Aerobic Aquatic pond System

485416

- 03 Acetone (one time)

+ Acetone/ Water (8/2; two times) Acetonitrile/ Water (4/1)
Soxhlet (Samples containing
>10% Un

extractable residues) 4% Yield of the 2 nd

extraction was quantified but

was not combined with
the 1 st extraction
nor it was analyzed 35.0%

Viable Aerobic Aquatic River System 4% 26.0%

### 20 Data show that un

- extractable residues in viable aerobic soil and aquatic systems were significantly high (26

- 35%) and that the Soxhlet step extracted only an additional 4% of the applied radioactivity (i.e.

, it is not a very effective extractant). Although the yield of this step was quantified, the chemical constituents were not analyzed. Furthermore, the
level of un

- extractable residues, in viable anaerobic soil and sterile aerobic soil systems

were v ery low compared to viable aerobic soil and aquatic systems (3.4

- 3.7% compared
to 26

- 35%). Based on these data, it can be stated that the formation of un

- extractable residues appears to be associated with prometryn degradation (i.e., degradation products

m ay constitute major part of the un

- extractable residues). Because prometryn is stable in anaerobic soil systems and that it is expected to be stable in sterile systems, formation of

un

- extractable residues in these systems is low because of lack of degrada tion. The association between prometryn degradation and formation of relatively high levels of un

extractable residues can also be seen in Figure 1

.

0.0 10.0 20.0 30.0 40.0 50.0 60.0 70.0 80.0 90.0 100.0

0 60 120 180 240 300 360% Of Applied Parent



## Time (Days) Parent

Un

- extractable Residues

Total Degradation Products 1 Yield from 2 nd Extraction (% of Total Extracted ) : For example the 4% yield entered for the river sediment is calculated as
follows: the 1 st extraction yielded on the average 48% with the 2 nd extraction the average yield increased by 2% to 50%, therefore the yield in % of total extracted= 2/50= 4%; N/D = Not determined

2 Total time of incubation was 360 days with steady increase of the un

- extractable residues (from 0.3 to 30.8%)

3 Total time of incubation was 30 days with no appreciable change in the un

- extractable residues (from 3.3 to 3.7%)

4 Total time of incubation was 60 days with no appreciable chan ge in the un

- extractable residues (from 1.7 to 3.4%)

### 21 Figure 1 Prometryn degradation and formation of un

- extractable residues in viable soil/aquatic systems (data points from one aerobic soil and two aerobic aquatic systems (pond and river).

Finally, an attempt was executed to try to further extract the residues. Selected samples were further refluxed (following the 1 st 

### and 2 nd 

### extraction) in neutral/acidic conditions. This step yielded, on the average, an additional 3% of the radioactivity from the river system (85% of it from neut ral reflux + 15% from acidic reflux) and 5% from the pond system (81% of it from neutral reflux + 19% from acidic reflux).

Data presented above indicate that there was an attempt to extract the residues; however, the attempt was not able to reduce un

- extr acted residues to an acceptable level. Furthermore, the constituents of the additional extract were not characterized. Data also
show a close association between parent degradation and the formation of the un

extractable residues, indicating the possibilit y that degradation products might be part of this residue. Due to the fact that disappearance of the parent might also be due to the incomplete extraction (in addition to degradation), the possibility that parent might be part of these un

- identified un

- ext racted residues may not be discounted.

(1) The formation of un

- extractable residues in various experimental conditions including, aerobic soil/aquatic systems and sterile/aerobic and anaerobic soil systems:
Data show that the level of un

- extracted residues wa s in the range of 26 to 35% of the applied radioactivity in one aerobic soil and two aerobic aquatic systems. This is compared to 3.4 to 3.7% in a sterile aerobic soil system and a viable anaerobic soil system. Due to the fact that no degradation occurs in viable anaerobic soil system and in sterile aerobic soil system, formation of un

- extracted residues can be related closely to prometryn degradation.

(2) A literature review of triazines and their degradation products (Donati and Funari, 1993) reported the following:

a. De

- isopropyl prometryn (a degradation product of prometryn) ha s been identified in soils as the main components of bound residues (i.e., un

- extracted residues);
b. Hydroxypropazine (a degradation product of prometryn) has been identified
as of bou nd residues (i.e., un

- extracted residues) associated with the fulvic acid extraction;

c. Following one year of incubation of a soil treated with prometryn, it was observed that the total bound residues (i.e., un

- extracted residues) consisted of
54% parent or De

- isopropyl prometryn, 8% Hydroxypropazine, 18% un

identified compounds and 20% decomposed to CO 2 

### as a result of the extraction procedure.

Conclusions on the nature of the un

- extracted residues are difficult to ascertain as it is necessary to examine ext raction procedures used in the above mentioned experiments and its possible effects on integrity of the extracted compounds.

### 22 However, these reports suggest that the presence of parent and degradates de

isopropyl prometryn and/or hydroxypropazine as part of the un

- extracted residues may not be discounted.

### 23 N

N N OH

N N CH

H CH 3 CH 3

CH

H H 3 C CH 3 

## 4.1. **Transformation Profile/Products**

The only major transformation product of prometryn, identified in submitted environmental fate studies, is Hydroxypropazine (GS

- 11526) . Minor transformation products whi ch were observed in amounts less than 10% of the applied parent include: Prometryn Sulfoxide (GS

- 16141)

, Des

- ethyl hydroxyatrazine (GS

- 17794) , and De

isopropyl prometryn (GS

- 11354 )

. Based on these data, the degradation profile of prometryn is summarized in Figure 2

.

Figure 2 Suggested degradation pathways for prometryn in varied laboratory and field
systems

N

N N S CH 3

N N CH

H CH 3 CH 3

CH

H H 3 C CH 3



### Prometryn Parent ( GS

- 34161)

N

N N S CH 3

N N CH

H CH 3 CH 3

CH

H H 3 C CH 3 O 

### Oxidation De

- alkylation



### Prometryn Sulfoxide 

### ( GS

- 16141 

### ) De

- isopropyl prometryn (GS

- 11354)

Hydroxypropazine (GS

- 

### 11526 ) Slow Degradation Aerobic Soil (t1⁄2 257 days) Aerobic Aquatic (t1⁄2= 110

- 236 days) Terrestrial Field Dissipation (DT 50 ”Dissipation half

- lives” 70

- 103 d)

N

N N S CH 3

N CH

H CH 3 CH 3

N

H H



### Des

- ethyl

- hydroxy atrazine (GS

- 

### 17794 )

### 24 It is noted that Appendix B, page 63 contains a table summary of the transformation products of prometryn and their maximum amounts formed.



# 5. Receptors

This section summarizes available eco

- toxicity data for prometryn. The toxic ity endpoints provided in these sections are the ones that the EPA intends to use quantitative ly in the Registration Review ecological risk assessment of prometryn; unless more sensitive endpoints become available prior to the time the assessment is conduc ted. It provides acute and chronic toxicity endpoints for the most sensitive test species of various taxonomic groups. When more than one toxicity value was available for the same species, the lower toxicity endpoint was selected.



## 5.1. Effects of Prometryn to Aquatic Organisms

Table 9 provides the selected toxicity endpoints for the most sensitive test species of various taxonomic groups of aquatic organisms. The acute toxicity data classifies prometryn as moderately toxic to fish and aquatic crustaceans, slightly toxic to bivalve
moll usks, and highly toxic to aquatic plants. With chronic exposure, toxicity studies show that prometryn begins to adversely affect the growth of juvenile fish at concentrations between 0.62 and 1.2 mg a.i./L, and the growth of young aquatic invertebrates at concentrations between 1.0 and 2.0 mg a.i./L. The select ed endpoints are from required ecotoxicity studies submitted by the registrant, except for acute toxicity to freshwater and saltwater invertebrates, for which lower toxicity endpoints were identified from studies published in the open literature.

Table 9 . Summary of the Most Sensitive Endpoints from Aquatic Toxicity Studies for Prometryn

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

ingredient) Acute Toxicity
Classification Source (MRID)

Freshwater fish 1 Acute Rainbow Trout ( Oncorhynchus mykiss ) 96

- hr LC 50 = 2.91 mg/L Moderately
Toxic 00070686 (Acceptable)

Chronic (Early
Life

Stage) Fathead Minnow ( Pimephales promelas ) NOAEC = 0.62 mg/L
LOAEC = 1.2 mg/L (Reduced length) N/A 43801702 (Acceptable)

Freshwater
invertebrates Acute Water Flea ( Daphnia magna ) 48

- hr EC 50 = 9.70 mg/L Moderately
Toxic Marchini et al., 1988 (Eco Ref. 13154)

Chronic Water Flea ( Daphnia magna ) NOAEC = 1.0 mg/L
LOAEC = 2.0 mg/L (Reduced length) N/A 40573720 (Acceptable)

### 25 Taxonomic Group Study Type Surrogate Species Toxicity Value (all units in
terms of active

ingredient) Acute Toxicity
Classification Source (MRID)

Estuarine/marine
fish Acute Sheepshead
Minnow ( Cyprinodon variegatus ) 96

- hr LC 50 = 5.14 mg/L Moderately
Toxic 40573717 (Acceptable)

Estuarine/marine

crustacean Acute Mysid ( Americamysis
bahia ) 96

- hr EC 50 = 2.32 mg/L Moderately
Toxic 40573718 (Acceptable)

Estuarine/marine
bivalve Acute Quahog Clam ( Mercenaria

mercenaria ) 48

- hr EC 50 = 21 mg/L Endpoint: shell growth Slightly toxic 40573719 (Acceptable)

Aquatic plants
and algae Vascular Duckweed ( Lemna gibba ) NOAEC = 3.99 μg/L
EC 50 = 11.9 μg/L Highly toxic 42520901 (Acceptable)

Non

vascular Freshwater diatom ( Navicula pelliculosa ) NOAEC = 0.288 μg/L
EC 50 = 1.04 μg/L Highly toxic 42620201 (Acceptable)

1 Freshwater fish may be surrogates for aquatic

- phase amphibians.



### The greatest concern for aquatic organisms is toxicity to aquatic plants. Large quantities of data are available on the toxicity of prometryn to various aquatic plants. These data
are summarized in Table 10 . None of the studies reported in the open literature provided
a lower 50% inhibition concentration ( IC 50 

### ) value than the ones provided by registrant

submitted study for vascular aquatic plants (11.9 μg a.i./L for Lemna gibba ) or for non

vascular aquatic plants (1.04 μg a.i./L Navicula pelliculosa ), and therefore will not be used for the RQ calculations. However, these data may be used to generate a s pecies sensitivity distribution for aquatic plants and to calculate the hazardous dose for 5% of aquatic plant species ( HD 05 

### ) (Aldenberg and Slob, 1993) to better characterize the risk of prometryn to aquatic plants.

Table 10

. Toxicity of Prometryn to Aquatic Plants

Taxonomic

Group Surrogate Species IC 50 (μg a.i./L) NOAEC 1

(μg a.i./L) LOAEC 1

(μg a.i./L) Endpoint Source 2
(MRID or Eco Ref #)

Duckweed Lemna gibba 11.9 3.99 8.42 14

- day frond

count 42520901

Lemna aequinoctiales 41.0 N/D N/D 8

- day population growth Eco Ref
78497

Lemna minor 53.8 N/D N/D 6

- day population growth rate Eco Ref
81431

Lemna perpusilla 13 N/D N/D 7

- day population growth Eco Ref 8628

Spirodela polyrhiza 85 N/D N/D 7

- day population growth Eco Ref 8628

Green Algae Selenastrum capricornutum 11.6 8.1 16 7

- day population growth 42520903

### 26 Taxonomic

Group Surrogate Species IC 50 (μg a.i./L) NOAEC 1

(μg a.i./L) LOAEC 1

(μg a.i./L) Endpoint Source 2
(MRID or Eco Ref #)

Scenedesmus quadricauda 9.7 N/D N/D 4

- day population growth Eco Ref
71458

Scenedesmus

acutus 45.9 N/D N/D 1

- day population
abundance Eco Ref
78497

Scenedesmus

acutus 1.27 N/D N/D 4

- day population growth rate Eco Ref
78497

Pseudokirchne
riella subcapitata 21 N/D N/D 4

- day population growth Eco Ref
15077

Chlorella fusca 12.4 0.812 N/D 1

- day population growth rate Eco Ref
62304

Chlorella pyrenoidosa 9.24 N/D N/D 4

- day population growth rate Eco Ref
61983 (Qualitative)

Chlorella pyrenoidosa 241 N/D N/D 1

- day doubling
time Eco Ref.
7485

Chlorella vulgaris 41.3 N/D N/D 4

- day population growth rate Eco Ref
65938 (Qualitative)

Dunaliella
tertiolecta 53 N/D N/D 4

- day population growth Eco Ref
15077

Chlorococcum

sp. 724 N/D N/D 1

- day doubling
time Eco Ref 7485

Cryptomonads Cryptomonas

sp. 17.7 15.2 30.3 6

- day population growth rate Eco Ref
105114

Diatoms Navicula pelliculosa 1.04 0.288 0.562 5

- day population growth 42620201 (Acceptable)

Skeletonema

costatum 7.82 2.22 4.54 5

- day population growth 42620202 (Acceptable)

Bluegreen algae Anabaena flos

aquae 40.1 20.2 35.2 5

- day population growth 42520902 (Acceptable)

Anabaena flos

aquae 724 N/D N/D 2

- day Chlorophyll A

content Eco Ref.
7485

Lyngbya sp. 314 N/D N/D 1

- day doubling
time Eco Ref.
7485

1 N/D denotes that the value was not determined.

2 Use of these open literature papers will depend on the results of the Agency’s review for acceptability. Papers classified a s Quantitative or Qualitative may be used for defining the species sensitivity
distribution. Results of reviews that have alread y been completed are noted.



## 5.2. Effects of Prometryn to Terrestrial Organisms

Table 11 provides the selected toxicity endpoints for the most sensitive test species of various taxonomic groups of terrestrial organisms. Prometryn shows little toxicity to

### 27 terrestrial wildlife. The acute toxicity data classifies prometryn as practically non

- toxic to birds and mammals. With chronic exposure, a dietary concentration of 750 mg ai/kg was found to cause reduced body weight gain in adult rats and their F1 pups. The NOAEC for
mammals was e stablished at 10 mg a.i./kg. In birds, chronic exposure to dietary concentrations of prometryn up to 500 mg a.i./kg caused no observable adverse effects in the mallard, and chronic exposure to dietary concentrations to 600 mg a.i./kg caused no
observable adverse effects in the northern bobwhite. An acute contact LD 50 

### study with the honey bee categorized prometryn as practically non

- toxic to bees.

As expected for an herbicide, prometryn i s highly toxic to terrestrial plants, with exposures less than 0.1 l b a

. i

. /A adversely affecting plant growth. The lowest toxicity endpoints were obtained in a vegetative vigor study, and the most sensitive species in this study was cucumber, for which the EC 25 

### and NOAEC were 0.006 and 0.019 lb a.i./A, respectively. These endpoints will be used in the quantitative risk assessment for terrestrial plants.

Table 11 . Summary of the Most Sensitive Endpoints from Terrestrial Toxicity Studies for Prometryn

Taxonomic

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

measured active ingredient) Acute Toxicity
Classification Source (MRID)

Birds 1 Acute Mallard ( Anas platyrhynchos ) 14

- d LD 50 > 4640 mg/kg

- bw No mortality at any dosage level, but
reduction in feed consumption and body weight gain at the 4640 mg/kg Practically

non

- toxic 00082966

Sub

- acute dietary Northern
bobwhite ( Colinus virginianus ) 8

- d LC 50 > 5000 mg/kg

- diet
One out of 10 died at
the 5000 mg/kg

- diet concentration on day 6; reductions in body weight gain and food consumption at ≥ 2500 mg/kg

- diet

. Practically

non

- toxic 40457502

Chronic Mallard ( Anas platyrhynchos ) NOAEC = 500 ppm LOAEC > 500 ppm
One non

- treatment related death at 250

ppm; no significant
sublethal effects at any test level. N/A 45280301

Mammals Acute Oral Laboratory rat ( Rattus norvegicus ) LD 50 = 1802 mg/kg

bw (males) Practically

non

- toxic 00060314

Acute
Dermal Laboratory rat ( Rattus norvegicus ) LD 50 > 3170 mg/kg

bw Toxicity Category III 00060647

### 28 Taxonomic

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

measured active ingredient) Acute Toxicity
Classification Source (MRID)

Acute
Inhalation Laboratory rat ( Rattus norvegicus ) LC 50 = 4.96 mg/L Toxicity Category III 40776601

Chronic Laboratory rat ( Rattus norvegicus ) NOAEC = 10 mg/kg

diet (0.65 mg/kg

- bw)
LOAEC = 750 mg/kg

- diet (50.7 mg/kg

- bw) Decreased parental and pup weights N/A 41445101

Insects Acute

contact Honey bee ( Apis mellifera

L. ) LD 50 > 96.7 μg/bee 10.4% mortality at 96.7 μg/bee Practically

non

- toxic 00036935

Terrestrial plants Seedling Emergence Dicot

– cabbage NO A EC = 0.038 lb/A
EC 25 = 0.014 lb/A Reduced plant height and shoot dry weight N/A 41035904

Monocot

– oat NOAEC = 0.075 lb/A
EC 25 = 0.07 lb/A Reduced shoot dry weight N/A 41035904

Terrestrial plants Vegetative Vigor Dicot

– cucumber NOAEC = 0.019 lb/A
EC 25 = 0.006 lb/A Reduced plant height N/A 41035903

Monocot

– onion NOAEC = 0.10 lb/A
EC 25 = 0.161 lb/A Reduced shoot dry weight N/A 41035903

1 Birds represent surrogates for terrestrial

- phase amphibians and reptiles.



## 5.3. Expected Toxicity of Transformation Products

Environmental fate studies have shown that degradation and metabolism of prometryn results in one major transformation product, hydroxypropazine (GS

- 11526), and three significant minor transformation products: des

- ethyl

- hydroxy

- atr azine (GS

- 17794), prometryn sulfoxide (GS

- 16141), and deethylametryn (GS

- 11354). Hydroxypropazine
and des

- ethyl

- hydroxy

- atrazine are formed with the substitution of the methylthio group of prometryn with a hydroxy group. Methylthio

- triazines, like prometr yn, are generally believed to lose much of their phytotoxicity when they are hydrolyzed into a hydroxy

- s

triazine, such as hydroxypropazine (Maier

- Bode, 1971). While phytotoxicity data are not
available for these prometryn transformation products, data for a very similar transformation product of atrazine, hydroxyatrazine, show that it has much less phytotoxicity than its parent compound, atrazine ( Stratton

, 1984 ; Kaufman and Joan
Blake

, 1970)

. Therefore, neither hydroxypropazine nor des

- ethyl

- hydroxy

- atrazine will be included as stressors to nontarget plants. For organisms other than terrestrial plants

### 29 (terrestrial animals, fish, aquatic invertebrates, and aquatic plants), hydroxypropazine will be considered an ecological stressor because it is a major degredation product (forms over 10% of the total residues) and because data are currently insufficient to conclude
that it is significantly less toxic to these to these taxa than the parent. T oxicity predictions generated by ECOSAR ( Table 12 ) as well as toxicity data of comparable atrazine transformation products suggest that hydroxypropazine may be less toxic than prometryn to aquatic animals and plants. Therefore, three basic toxicity studies are being requested to measure the acute toxicity of hydroxypropazine to a freshwater crustacean ( Daphnia

magna ), a vascular aquatic plant ( Lemna sp. ), and a freshwater algae ( Pseudokirchneriella subcapit ata ). The decision to consider this product a stressor to aquatic organisms will be re

- evaluated after these data are submitted and reviewed.

Table 12 . ECOSAR Predictions for Acute Toxicity of Prometryn and Hydroxypropazine to Aquatic Organisms. Organisms Class Toxicity Endpoint ECOSAR

- Predicted Toxicity (mg/L) Prometryn Hydroxypropazine

Fish 96

- hr LC 50 3.97 39.2 Daphnid 48

- hr LC 50 5.61 26.4 Green Algae 96

- hr EC 50 0. 0 34 0.106



### None of the three minor transformations products will be considered ecological stressors in the ecological risk assessment. P rometryn sulfoxide and deethylametryn will not included as stressors because they never form more than 10% of the total residues an d because they are transient products that further hydrolyzed into hydroxy

- s

- triazine s ( Figure 2 ). D es

- ethyl

- hydroxy

- atrazine will not be included as a stressor because it is a minor degradation product (<10% of total residues) and because there is some evidence that substitution of the methylthio group of prometryn with a hydroxy group would make the compound less t oxic to nont arget organisms than the prometryn

.

In summary, hydroxypropazine will be considered an ecological stressor for terrestrial animals, aquatic animals, and aquatic plants, unless new toxicity data demonstrates that it is significantly less toxic than the par ent compound (by at least a factor of 10) . Therefore, barring changes in the conclusion based on new data, predicted residues of this transformation product will be added to predicted residues of the parent compound when estimating the exposure to terrestr ial animals and all aquatic organisms. For terrestrial plants, exposure will be base on predicted residues of prometryn alone. Residues of the three minor transformation products will not be included in the exposure estimates for any nontarget animal or pl ant.



## 5.4. Ecological Incidents

The ecological incident information system (EIIS) is an OPP database that houses ecological incidents that have been reported to the Agency. When available, EIIS includes date and location of an incident, type and magnitude of effects observed in
various species, use(s) of pesticides known or suspected of contributing to the incident, and results of any chemical residue analysis or other analyses conducted during incident

### 30 investigation. EIIS incidents are categorized according to the certainty that the in cident resulted from pesticide exposure. The Avian Monitoring System (AIMS) is a database administered by the American Bird Conservancy that contains publicly available data on reported avian incidents involving pesticides. Many of the incidents listed i n this
database are also in the EIIS.

EIIS contains six incidents of crop damage that w ere linked to exposure to prometryn ( Appendix D ). Five of these incidents involved damage to cotton after direct application of this herbicide to that crop. One inci dent (I019130

- 056) was attributed to carryover of soil residues of prometryn, which allegedly resulted in damage to a rotational corn crop. The residues were of Suprend Herbicide (EPA Reg. No. 100

- 1163) which was

pre sumably applied to a cotton crop in the previous season. None of the plant damage incidents were attributed to spray drift or runoff of prometryn.

Three fish kill incidents in EIIS are associated with exposure to prometryn, but in each of these incidents the certainty level assigned for promet ryn was “unlikely” (I004021

- 004,
I004021

- 005, and I004668

- 011). All three were related to a series of fish kills that occurred in Richland County, Louisiana in 1996. Prometryn was one of 6 herbicides and one insecticide that were identified in water sampl es taken after the incident. These incidents were believed to have been caused by runoff of the insecticide profenofos, which was present at higher concentrations than prometryn and which is much more toxic to fish than prometryn. Prometryn was present at only small concentrations (0.15

- 0.59 μg/L). Since these concentrations are far below the lowest acute fish LC 50 

### (2910 μg/L), it probably was not a significant contributing factor to the fish mortality.

The AIMS was queried on 9 October 2012. At that tim e, no avian incident was listed which was attributed to prometryn.

Aggregated incident reports submitted by the registrant between 1998 and 2005 have included 5 minor plant incidents attributed to prometryn. These incidents were associated
with use of e ither Caparol 4L® (2 incidents) or Suprend® (3 incidents). Unless additional information on these aggregated incidents becomes available, they will be assumed to be representative of registered uses of prometryn in the risk assessment.

### 31 

# 6. Exposure Pathway s of Concern

Prometryn is highly persistent and highly mobile, but has low volatility and low propensity to bio

- accumulate. Considering these environmental fate characteristics, the following routes are expected to be primary for exposure to non

- target o rganisms:

• Consumption of contaminated food (sprayed food or treated seeds)

• Consumption of contaminated water

• Root uptake (plants)

• Spray drift exposure to organisms and aquatic habitats

• Runoff exposure to soil and aquatic habitats

• Leaching to ground water (for groundwater organisms and plants irrigated by ground water)

Because prometryn has been found to not bio

- accumulate much in fish (whole fish BCF = 85x, MRID 41022701), food

- chain routes of exposure, such as the consumption of fish by piscivorous wildlife, are not expected to be a major route of exposure. Available data indicates low volatility of prometryn suggesting long

- distance atmospheric deposition is not expected to be a significant route of exposure. However, the US Geological Survey (USGS) has reported the presence of pesticides in rain and wet deposition in four USA agricultural watersheds (Maryland, Indiana, Nebraska and California) at a 0.05 μg/L laboratory reporting limit (Vogel et al., 2008) 9 

### during the 2003

- 2004 sampling period. In California, prometryn was detected in rain in the San Joaquin

- Tulare

- M erced River 10


### basin, where a wide variety of crops are grown. Wet depositions were related to storm events during the rainy season (December

- March). Of 13 detections, a maximum concentration of 0.031 μg/L was detected in rain on December 11, 2003 and a maxi mum wet deposition of 0.735 μg/m 2 

### on December 16, 2003. Because data on detection of prometryn in rain and wet deposition is limited, spray drift estimates are used as high

- end estimates for potential atmospheric transport contributions.

Preliminary scree ns of the potential for drinking water and inhalation to be significant exposure pathways were assessed using the SIP (Screening Imbibition Program) and STIR (Screening Tool for Inhalation Risk) screening methods, respectively. Results of
the SIP model ind icated that exposure from drinking water alone is a potential concern for birds because of its potential to cause chronic effects, but is not a potential concern for mammals ( Appendix C, page 68 ). Results of the STIR model confirmed that inhalation is not likely to be a significant exposure pathway for wildlife. SIP and STIR
are described in detail at: http://www.epa.gov/oppefed1/models/terrestrial/index.htm

.

9 The cropland in West California (samples collected) is dominated by almonds and vineyards. In addition
to the California studi es, other studies were conducted in agricultural watersheds in Maryland, Indiana, and
Nebraska.

10 For description of the California’s Merced River Basin see Vogel et al. (2008) and pertinent references therein. The environmental setting of the Basin is d escribed in Gronberg & Kratzer (2007).

### 32 

# 7. Analysis Plan

7.1 Stressor of Concern

In addition to the p arent compound , residues of prometryn include un

- extractable residues plus the chemical degradates o f interest: Prometryn Sulfoxide ( GS

- 16141 )

, Hydroxypropazine ( GS

- 11526 )

, De

- isopropyl prometryn ( GS

- 11354 ) and Des

- ethyl

hydroxy atrazine ( GS

- 17794 ) . Following consideration of exposure and/or toxicity of all residues, it was decided that the stressor s of concern for risk assessment will be:

(1) Parent + un

- extracted residues for terrestrial plants;

(2) Parent + un

- extracted residues + GS

- 11526 for terrestrial animals;

(3) Parent + un

- extracted residues + GS

- 11526 for aquatic organisms ; unless new tox icity data (fr om requested studies) show that GS

- 11526 is less toxic than parent prometryn by at leas t one order of magnitude .

The m ajor transformation product of prometryn, h ydroxypropazine (GS

- 11526) , is expected to be much less toxic to terrestrial plants than the parent compound and thus will not be considered a stressor of concern for nontarget plants. Also, hydroxypropazine will be excluded as a stressor to aquatic animals and plants if requested toxicity test show
that it is less tox ic than prometryn by at least one order of magnitude (i.e., the EC 50 

### values are at least 10 times greater than those for prometryn).

The decision to include un

- extractable residues was based upon expected significant exposure from these un

- identified resi dues due to persistence and due to u nknown identity/toxicity

.

Hydroxypropazine (GS

- 11526) is a major degradate of prometryn, with observed
maximum concentrations in environmental fate studies of approximately 27% of the applied parent in laboratory studi es and 31% of the applied parent in field studies. This transformation causes the compound to lose its herbicidal activity, and thus it is expected to be much less toxic than prometryn to terrestrial plants. Toxicity of hydroxypropazine is
also expected t o be somewhat less than the parent for aquatic organisms as well, although the degree of the reduction in toxicity is uncertain at this time. Three acute toxicity tests with aquatic animals and plants are being requested to clarify the relative toxicity of prometryn and hydroxypropazine to these organism. For terrestrial animals, both prometryn and hydroxypropazine are expected to have low acute toxicity, and thus their
toxicities are considered to be similar.

A minor degradation product, desethylhydroxy

- atrazine (GS

- 17794), is another hydroxy

s

- triazine

, is not included as a ecological stressor because it is expected to have relatively low toxicity and is expected to form in the environment in only small amounts (less than 5% of the appli ed material. The other two minor degradation products

, prometryn sulfoxide and deethylametryn are both transient minor degradation products, with

### 33 observed concentrations in the environment of no more than 7% of the amount of parent applied . Therefore , thes e residues will not be considered ecological stressors

.



## 7.2. Measures of Exposure

EFED will use standard EPA models to evaluate exposure to aquatic and terrestrial organisms. Descriptions of these models are available a t:

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

Separate exposure assessments will be conducted for each of the labeled use sites. Similar crops that are in a crop group and have identical application restrictions, such as crops in the leafy petiole group, will be assessed as a group. Several scenarios will be used to assess exposure from use on cotton, representing the different use rates and use restrictions that the label impos es for different cotton

- growing regions. Separate analys e s will be conducted to assess exposure from ground, air blast, and aerial applications, as is appropriate for the use site.

Exposure will be modeled based on repeated applications of prometryn, wit h each application being made at the maximum application rate, and applications will be assumed to be made using the minimum inter

- application interval. These applications will be assumed to be made until the maximum per

- year application rate is reached. When necessary, the final application will be set to less than the maximum application rate to reach the maximum per

- year rate. When the maximum per

- year rate is not stated on the labels, then the stated maximum number of applications will be used. When neither the maximum per

- season application rate nor the maximum number of applications is stated, the maximum number of applications will be calculated based on the typical first application date, typical harvest date, minimum application interval, and

pr e

- harvest interval.

Predicted aquatic exposures will be estimated using the most current version of the Pesticide Root Zone Model (PRZM) and Exposure Analysis Modeling System (EXAMS), in conjunction with the most recent version of EFED’s input shell, PE ( current version 5.0). These models predict maximum and time

- averaged expected environmental concentrations (EECs) in a standard pond resulting from transport of prometryn residues by way of runoff and spray drift. Residues of prometryn in the soil
will b e assumed to degrade between applications. Since laboratory studies have shown that prometryn is stable to hydrolysis and photolysis, degradation will be driven by aerobic soil and aquatic metabolism. Soil binding will also be assumed based on
measured K f oc 

### values and assumed soil types, although these parameters indicate that soil binding of prometryn would be minimal.

Exposure to terrestrial animals will be estimated using the latest version of EFED’s Terrestrial Residue Exposure model (T

- REX, current v ersion 1.5). T

- REX predicts maximum expected environmental concentrations (EECs) of pesticide residues on wildlife food items. These maximum EECs are based on the maximum application rate,

### 34 maximum number of applications per season, and minimum inter

- appl ication intervals. Residues are assumed to dissipate on the food items between the multiple applications. Since prometryn is a highly stable compound, the default foliar dissipation half

- life of 35 days will be assumed.



## 7.3. Measures of Effect

Toxicity data presented in Section 3 of this problem formulation will be used to calculate risk quotients. Any additional information submitted by the registrant or found in the open literature prior to conduct of the risk assess ment will also be considered. The open literature studies are identified using EPA’s ECOTOXicology database (ECOTOX) (USEPA, 2013), which employs a literature search engine for locating chemical toxicity data for aquatic life, terrestrial plants, and wild life. The evaluation of both sources of data can also provide insight into the direct and indirect effects of pesticides on biotic communities from loss of species that are sensitive to the chemicals and from changes in
structure and functional characteri stics of the affected communities.



## 7.4. Endangered Species Assessments

Consistent with the Agency’s responsibility under the Endangered Species Act (ESA), the Agency will evaluate risks to federally listed threatened and/or endangered (listed) species from registered uses of pesticides in R egistration R eview. The process for evaluating potential risks to listed species is further described at http://www.epa.gov/oppfead1/endanger/litst atus/riskasses.htm

.



## 7.5. Endocrine Disruptor Screening Program

As required by FIFRA and FFDCA, EPA reviews numerous studies to assess potential adverse outcomes from exposure to chemicals. Collectively, these studies include acute, subchronic and chronic toxicity, including assessments of carcinogenicity, neurotoxici ty, developmental, reproductive, and general or systemic toxicity. These studies include endpoints which may be susceptible to endocrine influence, including effects on endocrine target organ histopathology, organ weights, estrus cyclicity, sexual maturati on, fertility, pregnancy rates, reproductive loss, and sex ratios in offspring. For ecological hazard assessments, EPA evaluates acute tests and chronic studies that assess growth, developmental and reproductive effects in different taxonomic groups. As part of its most recent registration decision , EPA reviewed these data and selected the most sensitive endpoints for relevant risk assessment scenarios from the existing hazard database. However, as required by FFDCA section 408(p), prometryn is subject t o the endocrine screening part of the Endocrine Disruptor Screening Program (EDSP).

EPA has developed the EDSP to determine whether certain substances (including pesticide active and other ingredients) may have an effect in humans or wildlife similar to an effect produced by a “naturally occurring estrogen, or other such endocrine effects as

### 35 the Administrator may designate.” The EDSP employs a two

- tiered approach to making the statutorily required determinations. Tier 1 consists of a battery of 11 screen ing assays to identify the potential of a chemical substance to interact with the estrogen, androgen, or thyroid (E, A, or T) hormonal systems. Chemicals that go through Tier 1 screening and are found to have the potential to interact with E, A, or T horm onal systems will proceed to the next stage of the EDSP where EPA will determine which, if any, of the Tier 2 tests are necessary based on the available data. Tier 2 testing is designed to identify any adverse endocrine

- related effects caused by the substa nce, and establish a
dose

- response relationship between the dose and the E, A, or T effect.

Under FFDCA section 408(p), the Agency must screen all pesticide chemicals. Between October 2009 and February 2010, EPA issued test orders/data call

- ins for the first group of 67 chemicals, which contains 58 pesticide active ingredients and 9 inert ingredients. Prometryn is not among the group of 58 pesticide active ingredients on the initial list to be screened under the EDSP. Accordingly, as part of R egistrati on R eview, EPA will
issue future EDSP orders/data call

- ins, requiring the submission of EDSP screening assays for prometryn. For further information on the status of the EDSP, the policies and procedures, the list of 67 chemicals, future lists, the test gu idelines and the Tier 1 screening battery, please visit our website: http://www.epa.gov/endo/

.

### 36 

# 8. Preliminary Identification of Data Gaps

**8.2. Environmental Fate** 

Table 13 identify environmental fate studies by MRID that offer data for each guideline requirement, as well as study classifications and whether or not further data are needed in order to support ris k assessment.

Table 13 Status of Environmental Fate Data Requirements for Prometryn

OCSPP
Guideline Data Requirement Submitted Studies (MRID) Study Classifications Are data needed
to conduct risk

assessment? Justification and Assumptions EPA will Make in Absence of Data

- Some Example texts are include

835.2120 Hydrolysis 405737

- 04 Acceptable No N/A

835.2240 Aqueous photolysis 405737

- 05 Acceptable No N/A

835.2410 Soil photolysis 405737

- 06 Acceptable No N/A

835.4100 Aerobic soil metabolism 001483

- 38 Acceptable Yes Half

- life used for modeling will be multiplied by 3 1

835.4200 Anaerobic soil metabolism 411559

- 01 Acceptable No N/A

835.4300 Aerobic aquatic metabolism 485416

- 03 Under review

835.44 00 A na erobic aquatic metabolism None Submitted Yes Chemical will be considered Stable

835.1230
835.1240 Adsorption/ desorption and leaching 418759

- 01 Acceptable

No N/A 418759

- 02 Acceptable

418759

- 03 Acceptable

835.1410 Volatility

– laboratory 418759

- 06 Acceptable No N/A

835.6100 Terrestrial field dissipation 415464

- 01 &
422539

- 03 Acceptable

No N/A 415464

- 02 &

422539

- 04 Acceptable

415464

- 03 &

422539

- 01 Acceptable

415464

- 04 &

422539

- 02 Acceptable Analytical method in soil None Submitted Yes Required

835.6200 Analytical method in water None Submitted Yes Required

850.1730 Fish bio

- concentration 410227

- 01 Acceptable No N/A

1 As per model input guidance 11



### Examination of the list of submitted studies ( Table 13 ) indicates the following data gaps:

(1) 

### Aerobic soil metabolism : only one aerobic soil study was submitted. EFED
request s two more studies on soils representing the major areas where prometryn will be used (main cotton areas of the country). Before conducting these studies,

11 

### Guidance for Selecting Input Parameters in Modeling the Environmental Fate and Transport of Pesticides . URL: http://www.e pa.gov/oppefed1/models/water/input_parameter_guidance.htm#Przm

### 37 further effort is to be executed to show that the extraction method to be used is the
most efficient method available. It is recommended that a literature search is performed for the best extraction method due to the fact that other researchers had reported extraction methods showing un

- extracted residues conta ining parent and degradates;

(2) 

### Anaerobic aquatic metabolism study: none was submitted and because the
chemical is stabl e under a naerobic soil conditions, it will be considered also stable under anaerobic aquatic conditions unless a study is submitted; and

(3) 

### Environmental Chemistry Methods (ECMs) for soil and water along with their independent laboratory validation (ILVs). It is recommended to device state of the art methods that employ existing multi

- pesticide analytical procedures; when possible.



## 8.3. **Ecological Effects**

Table 14 and Table 15 identify the status of study requirements for assessing the ecological effects of prometryn to aquatic organisms and terrestrial organisms, respectively. These tables identify ecological eff ects studies that offer data for each guideline requirement, as well as acceptability classifications of those studies, and whether additional data are needed in order to support risk assessment.

Table 14 . Status of Data Require ments for Assessing the Ecological Effects of Prometryn to Aquatic Organisms

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

needed to
conduct

risk
assessment? Justification and Assumptions
EPA will Make in Absence of

Data

- Some Example texts are
include d

850.1010 Freshwater
invertebrate acute toxicity 00070146 Acceptable No

--

850.1025
850.1055 Saltwater
invertebrate acute toxicity (bivalve) 40573719 Acceptable No

--

850.1035
850.1045 Saltwater
invertebrate acute toxicity (crustacean) 40573718 Acceptable No

--

850.1075 Freshwater
fish acute toxicity 00070686 Acceptable No

--

00070686 Supplemental

00040692 Acceptable 1

00020692 Acceptable 1

00121154 Acceptable 2

00121155 Acceptable 2

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

needed to
conduct

risk
assessment? Justification and Assumptions
EPA will Make in Absence of

Data

- Some Example texts are
include d

850.1075 Saltwater fish acute toxicity 40573717 Acceptable No

--

850.1300 Freshwater
invertebrate life cycle 40573720 Acceptable No

--

850.1350 Saltwater
invertebrates life cycle -- -- Yes A guideline compliant saltwater invertebrate life cycle test is needed. Prometryn is highly persistent in aquatic environments. Its high mobility
and use in coastal areas makes it likely to enter saltwater environments in significant concentrations. Also, in previous risk assessments, aquatic EECs have been greater than 0.01 the
acute EC 50 for the mysid.

850.1400 Freshwater
fish early

- life
stage 43801702 Acceptable No NOTE: MRID 43801702 was originally classified as Supplemental but was upgraded to Acceptable in 1997. 40573721 Invalid

850.1400 Saltwater fish early

- life
stage No

--

850.1500 Fish life cycle No

--

850.1735
850.1740 Whole
sediment

acute invertebrate No Due to the high persistence of prometryn, acute sediment toxicity testing is not required at this time

.
Non

guideline studies,
850.1760 850.1770, 850.1780, in prep. Whole
sediment
chronic
invertebrate Yes Guideline

- compliant studies are needed on the chronic toxicity of prometryn to sediment

- dwelling organisms. Chronic studies are requested because prometryn is highly persistent in aquatic environments, is expected to bind to sediment, and the expected

pea k pore water concentration is greater than 1/10 the acute EC50
for the Daphnia magna and the mysid.

850.4400 Aquatic plant toxicity test using Lemna

spp. 40520901 Acceptable No

--

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

needed to
conduct

risk
assessment? Justification and Assumptions
EPA will Make in Absence of

Data

- Some Example texts are
include d

850. 4 5 00 A lgal toxicity 42520903 Acceptable No

--

42620201 Acceptable

42620202 Acceptable

850.4550 Cyanobacteria ( Anabaena flos

- aquae ) Toxicity 42530902 Acceptable No

1 This study was conducted with Primaze 80W (40% prometryn and 38% atrazine). 2 This study was conducted with Caparol 80W (80% prometryn)

.



### Table 15 . Status of Data Requirements for Assessing the Ecological Effects of Prometryn to Terrestrial Organisms

OCSPP
Guideline Data Requirement Submitted
Studies (MRID) Study
Classifications Are data
needed for
risk
assessment? Current Additional Data
Need

850.2100 Avian oral toxicity 00082966 Acceptable No Because of the very low toxicity observed in the avian acute oral and avian dietary test, an acute oral test with a passerine species is not needed
at this time

.
850.2200 Avian dietary toxicity 40457502 Acceptable No

--

00070686 Acceptable

00070686 Supplemental 1

850.2300 Avian reproduction 41035901 Acceptable No

44556801 Acceptable

41035902 Invalid

Non

guideline Avian
inhalation No

850.3020 Honey bee

acute contact toxicity 00036935 Acceptable No

--

850.3030 Honey bee
residue on foliage No

--

850.3040 Field testing
for pollinators No

--

850.4100 S eedling

emergence 40457504 (Tier 1) Acceptable No

--

### 40 OCSPP
Guideline Data Requirement Submitted
Studies (MRID) Study
Classifications Are data
needed for
risk
assessment? Current Additional Data
Need

and seedling growth 41035903 (Tier 2) Acceptable No

850.4150 V egetative vigor 40457505 (Tier 1) Acceptable No

41035904 Acceptable No
1 MRID 00070686 included avian dietary tests with the mallard and the northern bobwhite. The test with
the mallard was A cceptable whereas the test with the northern bobwhite was S upplemental

.



### The available data on the ecological effects of prometryn to aquatic and terrestrial organisms are complete with the exception of data on the chronic toxicity to saltwater mysid. A study test ing the life

- cycle toxicity of prometryn to the mysid (Guideline No. 850.1350) is need ed to fill this data gap. The following criteria make this study required for prometryn:

• Prometryn has outdoor terrestrial use sites that occur in coastal areas and coul d result in exposure to estuarine and marine habitats.

• The high mobility and persistence of prometryn make significant movement of prometryn into estuarine and marine habitats likely.

• Prometryn is a persistent pesticide (stable to hydrolysis and aqueous ph otolysis at

22 ° C)

• In previous assessments, the EEC in water was found to be greater than 0.01 the
acute EC 50 

### of the mysid.

This study is needed to assess the risk of the use of prometryn to saltwater invertebrates living in estuarine and marine habitats, and likelihood that prometryn may affect listed species of invertebrates that occur in these habitats. Without data from this study, the EPA would need to estimate the chronic toxicity of prometryn to the mysid using the

acute

- to

- chronic ratio method. Th is would increase the uncertainty of the risk conclusions for these species.

Sediment Toxicity Testing

No data are available on the toxicity of prometryn to sediment

- dwelling invertebrates. The use pattern, chemical properties, estimated exposure, and toxicity profile of
prometryn indicate need for chronic (life cycle) sediment toxicity tests to fully evaluate potential risks to benthic invertebrates. Prometryn meets the following criteria for sediment toxicity testing, as defined in the Code of Federa l Regulations:

• The EEC in sediment is greater than one

- tenth of the acute EC 50 

### values.

PRZM/EXAMS runs were executed for three cotton scenarios (CA, MS and NC) with a total application rate of 5.5 lbs a.i/A assumed to be applied as follows: 2.0

### 41 lbs a.i/ A as winter application + 2.8 lbs a.i/A as pre

- plant incorporated to 10 cm + 0.7 lbs a.i/A as post

- emergence application. The results indicates that the peak pore water EECs range from as low as 19 ppb for CA to as high as 1,200 ppb for
NC . One tenth the a cute EC50 is 970 ppb when based on the daphn id acute EC 50 

### and 232 ppb when based on the mysid EC 50



### .

• The half

- life of the pesticide in sediment is >10 days.

The aerobic soil metabolism half

- life is 257 days (MRID 00148338) and the
aerobic metabolism half

- live s are 110 days ( pond system, MRID 48541603) and 236 days (river system, MRID 48541603)

• The log K
ow 

### is greater than 3.

The log K
ow 

### for prometryn is 3.46.

Life

- cycle sediment toxicity studies needed for risk ecological assessment include two freshwater species (the midge, Chironomus dilutus and the amphipod, Hyalella azteca ) and one saltwater species (the amphipod, Leptocheirus plumulosus ). Multiple species are being recommended in order to account for differential sensitivity and exposure potential of benthic invertebrates to prometryn. Specifically , the following chronic studies are requested:

1. Test Method 100.4: Hyalella azteca 42

- d Test for Measuring th e Effects of Sediment Associated Contaminants on Survival, Growth, and Reproduction in USEPA 2000 Methods for Measuring the Toxicity and Bioaccumulation of
Sediment

- associated Contaminants with Freshwater Invertebrates EPA 600/R

99/064 (proposed guideline number 850.1770)

2. Test Method 100.5: Life

- cycle Test for Measuring the Effects of Sediment

associated Contaminants on Chironomus dilutus or C. tentans in USEPA 2000 Methods for Measuring the Toxicity and Bioaccumulation of Sediment

- associated
Contaminants w ith Freshwater Invertebrates EPA 600/R

- 99/064 (proposed guideline number 850.1760)

3. Leptocheirus plumulosus in USEPA 2001 Method for Assessing the Chronic Toxicity of Marine and Estuarine Sediment

- associated Contaminants with the Amphipod Leptocheirus plumu losus EPA 600/R

- 01/020 (proposed guideline number 850.1780)

Toxicity testing with Transformation Products

As discussed in Section 5.3, indirect evidence indicates that the major transformation product, hydroxypropazine (GS

- 11526), is likely to be less t oxic than the parent compound, prometryn, but some basic acute aquatic toxicity testing is needed to confirm this. Acute hydroxypropazine toxicity tests are requested with one aquatic invertebrate

### 42 and two aquatic plants, one vascular and one nonvascular. Specifically, the following guideline test are requested for hydroxypropazine:

• 850.1010 Aquatic invertebrate acute toxicity, freshwater daphnids

• 850.4400 Aquatic plant toxicity test using Lemna sp.

• 850.5400 Algal toxicity using green algae Pseudokirchneriella subcapitata

Tier 2 tests are recommended for the aquatic plant testing of hydroxypropazine, although tier 1 test would be acceptable if they show inhibition of less than 50% at a concentration of 2.5 mg ai/L or greater. These data wou ld be used to determine if hydroxypropazine
should be considered an ecological stressor and included in estimates of total toxic
residues in the ec ological risk assessment. This transformation product will be included if any of these tests show that hydro xypropazine has toxicity equal to or greater t han prometryn. Otherwise, the transformation product will not be included, and the risk assessment will be based on exposure to the parent compound alone.



# 9. References

Literature References

Aldenberg, T. and W. Slobb. 1993. Confidence limits for hazardous concentrations based on logistically distributed NOEC toxicity data. Ecotoxicol. Environ. Saf. 25:48

- 63.

Cessna, A.J. 2008. Nonbiological Degradation of Triazine Herbicides: Photolysis and Hydrolysis. Chapter 23 in Triazine Herbicides , edited by Janis McFarland and Orvin C. Burside. Published by Elsevier Science and Technology Books, March 2008, New York.

Connell, LL., Harman

- Fetch and Hagy, L.D. 2004. Measured Concentrations of
Herbicid es and Model Predictions of Atrazine Fate in the Patuxent River Estuary. J. Env. Qual., Vol 33, pp 594

- 604

Donati, L. and E. Funari. 1993. Review of leaching characteristics of triazines and their degradation products. Ann. 1 st 

### Super. Sanità 29(2):225

- 24 1.

Garbini, J.R., Milori, D., Simoes, M.L., Wilson, T.L. and Martin, N. 2007 Influence if humic substances on the photolysis of aqueous pesticide residues. Chemosphere, ol 66, pp 1692

- 1698.

Kaufman, D.D. and J. Blake. 1970. Degradation of atrazine by soil fungi. Soil Biol.
Biochem. 2:73

- 80.

### 43 Kontantinous, I.K, Zardalkis, and Albanis, T.A. 2001. Photodegradation of selected
herbicides in various natural waters and soils under environmental co nditions

. J.Eviron. Qual, Vol. 30, pp 121

- 130.

Maier

- Bode, H. 1971. Herbizide und ihre Ruckstande . Verlag Engen Ulmer, Stuttgart.

Marchini, S., L. Passerini, D. Cesareo, and M.L. Tosato. 1988. Herbicidal Triazines: Acute Toxicity on Daphnia, Fish, and P lants and Analysis of its Relationships
with Structural Factors. Ecotoxicol. Environ. Saf. 16(2):148

- 157

Popova, G.V. 1976. Characteristics of the effect of the herbicide prometryn on fish.
Nauchn. Osn. Okhr. Prir. 4:118

- 125. (Eco Ref No. 7890)

Ralston

- Ho oper,K., J. Hardy, L. Hahn, H. Ochoa

- Acuna, L.S. Lee, R. Mollenhauer, and M.S. Sepulveda. 2009. Acute and chronic toxicity of atrazine and its metabolites deethylatrazine and deisopropylatrazine on aquatic organisms.

E cotoxicology18(7): 899

- 905. (Eco Ref No. 118745)

Stratton, G. W. 1984. Effects of the herbicide atrazine and its degradation products, alone and in combination, on phototrophic microorganisms. Bull. Environ.
Contam. Toxicol. 29:35

- 42. (MRID # 450874

- 01).

USEPA, 2009. Prometryn (CAS Reg. No. 7287

- 19

- 6) Tier I Drinking Water Assessment for the Proposed New Uses on Carrots, Okra, Parsley, Cilantro, Celeriac, and Leafy Petioles. DP Barcode 357096/99 Dated June 19, 2009. 10 p. USEPA, 2013 USEPA. 2013. ECOTOX User Guide: ECOTOXicology Database System. Version 4.0. Available: http:/www.epa.gov/ecotox/

Vogel, J.R., Majewski,, M.S. . and Capel, P.D. 2008. Pesticides in Rain in Four Agricultural Watersheds in the United States. J. Env. Qual., Vol 37, pp. 1105

- 1115.



## Submitted Fate Studies

001483

- 34

405737

- 04 Lawrence, L.J. 1987. Hydrolysis of 14 

### C prometryn in aqueous solutions at pH 5, 7, and 9. Laboratory Project No. 194. Report No. 1129. Unpublished Study performed by Pharmacology and Toxicology Research Laboratory, Lexington, KY, and submitte d by
Ciba

- Geigy Corporation, Greensboro, NC.

405737

- 05 Lawrence, L.J. 1987. Solution photolysis of 14 

### C prometryn under natural sunlight conditions. Laboratory Project No. 195. Report No. 1138. Study performed by

### 44 Pharmacology and Toxicology Research Labora tory, Lexington, KY, and submitted by
Ciba

- Geigy Corporation, Greensboro, NC.

405737

- 06 Lawrence, L.J. 1987. Soil surface photolysis of 14 

### C prometryn under natural sunlight. Laboratory Project No. 196. Report No. 4135. Unpublished study performed by
Pharm acology and Toxicology Research Laboratory, Lexington, KY, and submitted by
Ciba

- Geigy Corporation, Greensboro, NC.

001483

- 38 Ellgehausen, H. 1979. Degradation of prometryn (Gesagard) in aerobic, aerobic/anaerobic, and sterile /aerobic conditions. Project report 20/79. Biochemistry Department R&D, Plant Protection, Agricultural division, Ciba Geigy Ltd, Basle,
Switzerland.

41155901 Saxena, A.M. 1989. Aerobic/anaerobic soi1 metabolism of 14 

### C prometryn. Laboratory Study ID: HLA 6015

- 384. Unpublished study performed by Hazleton Laboratories America, Inc., Madison, WI, and Ciba Geigy Corporation, Greensboro, NC.

485416

- 03
Schulze

- Aurich. 2000. Degradation and Metabolism of [UYC]triazine G

- 34161 in two Aerobic Aquatic Systems under laboratory, including amendment 1. Study Number 98SA01. Unpublished study performed by Novartis Crop Protection
AG Environmental Safety/ Eco

- chemistry, 4 002 Basel, Switzerland and submitted by Syngenta Crop Protection, LLC, 410 Swing Road, P.O Box 18300, Gr eensboro, NC
27419

- 8300.

418759

- 01 Kestrson, A., 1991. Soil adsorption/desorption of [ 14 

### C] prometryn by the batch equilibrium method. Laboratory Project ID: project No. 526; Ciba

- Geigy Protocol No.
190

- 90. Unpublished study performed by Pharmacology and Toxicology Research Laboratory, Lexington, KY, and submitted by Ciba

- Geigy Corporation, Greensboro, NC.
418759

- 02 Kestrson, A., 1991. Soil adsorption/desorption of [ 14 

### C] GS

- 11354 by the batch equilibrium method. Laboratory Project ID: project No. 528; Ciba

- Geigy Protocol No.
188

- 90. Unpublished study performed by Pharmacology and Toxicology Research Laboratory, Lexington, KY, and submitted by Ciba

- Geigy Corporation, Greensboro, NC.
418759

- 03 Kestrson, A., 1991. Soil adsorption/desorption of [ 14 

### C] hydroxypro pazine by the batch equilibrium method. Laboratory Project ID: project No. 527; Ciba

- Geigy Protocol No.
189

- 90. Unpublished study performed by Pharmacology and Toxicology Research Laboratory, Lexington, KY, and submitted by Ciba

- Geigy Corporation, Greensbo ro, NC.

418759

- 06

### 45 Jackson S.B. 1991. Laboratory volatility of 14 

### C prometryn.. Laboratory Project ID: PTRL project No. 521. Study performed by Pharmacology and Toxicology Research Laboratory East, Richmond, KY, and submitted by Ciba

- Geigy Corporation, Gree nsboro, NC.

410227

- 01 Forbis, A.D. and T.D.J. Halls. 1988. Uptake, depuration and bioconcentration of 14 

### C

prometryn to bluegill sunfish (Lepomis macrochirus), and characterization of 14 

### C

prometryn residues in fish tissue and water. Laboratory Study No. 361341. Unpublished study performed by Analytical Bio

- Chemistry Laboratories, Inc., Columbia, MO, and submitted by Ciba

- Geigy Corporation, and submitted by Ciba

- Geigy

415464

- 01
A. Landis International, Inc. 1990. Caparol 4L terrestrial field dissipation study on
cotton in California. LA Protocol No. 1641

- 88

- 71

- 16

- 11B

- 15.Unpublished study performed by Landis International, Inc., Valdosta, GA and Minnesota Vally Testing Labs., New Ulm, MN; and submitted by Ciba

- Geigy Corporation, Greensboro, NC.

B. Anderson, S.C. 1990. Residue determination of prometryn, GS

- 11354, and
GS

- 11525 from California cropped field dissipation soil samples. MVTL Protocol No. 8808C. Unpublished study performed by Minnesota Valley Testing Labs. Inc., New Ulm, MN ; and submitted by Ciba

- Ge igy Corporation, Greensboro, NC.

422539

- 03 Fleming, P.L., and Wiepke, T. 1990. Supplemental to MRID 4154601. Caparol 4L Field Dissipation Study on Cotton in California. Laboratory Project ID: 8808C. Unpublished study performed by Minnesota Valley Testing Laboratories, Inc., New Ulm, MN, and submitted by Ciba

- Geigy Corporation, Greensboro, NC.

415464

- 02
A. Landis International, Inc. 1990. Caparol 4L terrestrial field dissipation on bareground in California. LA Protocol No. 1641

- 88

- 71

- 16

- hed study performed
b y Landis International, Inc., Minnesota Valley Testing Labs., Inc., New Ulm, MN; and Geigy Corporation, Greensboro, NC.

B. Anderson. S.C. 1990a. Residue determination of prometryn, GS

- 11354, and GS

11526 from California bare ground field dissipation soil sa mples. MVTL Protocol No. 8808D. Unpublished study by Minnesota Valley Testing Labs., Inc., New Ulm, MN; and submitted by Ciba

- Geigy Corporation, Greensboro, NC

422539

- 04 Fleming, P.L., and Wiepke, T. 1990. Supplemental to MRID 415464

- 02. Caparol 4L
Field Dissipation Study on Bare Ground in California. Laboratory Project ID: 8808D. Unpublished study performed by Minnesota Valley Testing Laboratories, Inc., New Ulm, MN, and submitted by Ciba

- Geigy Corporation, Greensboro, NC.

415464

- 03

### 46 A. Landis International, Inc. 1990c. Caparol 4L terrestrial field dissipation on cotton
in Texas. LA Protocol No. 1641

- 88

- 71

- 16

- 11B

- 13. Unpublished study performed by Landis International, Inc., Valdosta, GA, esota Valley Testing Labs., Inc., New Ulm, MN; and submitted by gy Corp oration, Greensboro, NC.

B. Anderson, S.C. 1990d. Residue determination of prometryn, GS

- 11354, and GS

11526 from Texas cropped field dissipation soil samples. MVTL Protocol No. 8808A.Unpublished study performed by Minnesota Valley Testing Labs, Inc., New Ulm, MN; and submitted by Ci ba

- Geigy Corporation, Greensboro, NC.

422539

- 01 Fleming, P.L., and Wiepke, T. 1990. Supplemental to MRID 41546

- 03. Caparol 4L Field Dissipation Study on Cotton in Texas. Laboratory Project ID: 8808A. Unpublished study performed by Minnesota Valley Testing Laboratories, Inc., New Ulm, MN, and submitted by Ciba

- Geigy Corporation, Greensboro, NC.

415464

- 04
A. Landis International, Inc. 1990b. Caparol 4L terrestrial field dissipation on bare

ground in Texas. LA Protocol No. 1641

- 88

- 71

- 16

- 21E

- 14. Unpublished stud y performed by Landis International. Inc., Valdosta, GA, and Minnesota Valley Testing Labs., Inc., New Ulm, MN; and submitted by Ciba

- Geigy Corporation, Greensboro, NC.

B. Anderson. S.C. 1990c. Residue determination of prometryn GS

- 11354, and GS

11526 from Texas bare ground field dissipation soil samples. MVTL , Protocol No. 8808B. Unpublished study performed by Minnesota Valley Testing Labs Inc., New Ulm, MN; and submitted by Ciba

- Geigy Corporation, Greensboro, NC

422539

- 02 Fleming, P.L., and Wiepke, T. 19 90. Supplemental to MRID 415464

- 04. Caparol 4L Field Dissipation Study on Bare Ground in Texas. Laboratory Project ID: 8808B. Unpublished study performed by Minnesota Valley Testing Laboratories, Inc., New Ulm, MN, and submitted by Ciba

- Geigy Corporation, Greensboro, NC.



## Submitted Ecological Effects Studies

71

- 1 Avian Single Dose Oral Toxicity

MRID DOC# Citation Reference

56908 Summary report Ciba

- Geigy Corporation (1967) Toxicology: (Evik(R)). (Reports by various sources; unpublished study including IBT nos. B4715, C4716 and P4709, received Apr 14, 1971 under 1G1142; CDL:
090929

- B)

70686 2028297
2028298 Beliles, R.P.; Scott, W.; Knott, W. (1965) Prometryne: Safety Evaluation on Fish and Wildlife (Bobwhite Quail, Mallard Ducks,

### 47 2028299
2028300
2028301 Rainbow Trout, Sunfish, Goldfish). (Unpublished study received Dec 29, 1977 under 100

- 542; prepared by Woodard Research Corp., sub mitted by Ciba

- Geigy Corp., Greensboro, N.C.;
CDL:232551

- B)

82966 2028303 Fink, R.; Beavers, J.B.; Brown, R. (1977) Final Report: Acute Oral
LD50

-- Mallard Duck: Project No. 108

- 131. (Unpublished study received Dec 29, 1977 under 100

- 542; prepared by Wil dlife Inter

national Ltd. and Washington College, submitted by Ciba

- Geigy Corp., Greensboro, N.C.; CDL:232551

- C)

40457501 DER not
located Fletcher, D. (1984) Acute Oral Toxicity Study with Prometryn Technical in Bobwhite Quail: Lab Study Number BLAL No. 84QD44. Unpublished study performed by Bio

- Life Associates. 21

p. 

## 71

- 2 Avian Dietary Toxicity

MRID DOC# Citation Reference

70686 2028298
2028301 Beliles, R.P.; Scott, W.; Knott, W. (1965) Prometryne: Safety Evaluation on Fish and Wildlife ( Bobwhite Quail, Mallard Ducks, Rainbow Trout, Sunfish, Goldfish). (Unpublished study received Dec 29, 1977 under 100

- 542; prepared by Woodard Research Corp., submitted by Ciba

- Geigy Corp., Greensboro, N.C.; CDL:232551

- B)

40457502 2028306 Fletcher, D. (19 84) 8

- Day Dietary LC50 Study with Prometryn Technical in Bobwhite Quail: Study Number BLAL No. 84QC43. Unpublished study performed by Bio

- Life Associates. 23 p.

40457503 DER not
located Fletcher, D. (1984) 8

- Day Dietary LC50 Study with Prometryn
Technica l in Mallard Ducks: Study Number BLAL No. 84DC44. Unpublished study performed by Bio

- Life Associates. 23 p.


## 71

- 4 Avian Reproduction

MRID DOC# Citation Reference

41035901 2028315 Fletcher, D.; Pedersen, C. (1989) Prometryn Technical: Toxicity and Reproduction Study in Mallard Ducks: Study No. 87 DR 21. Unpu

- blished study prepared by Bio

- Life Associates, Ltd. 55 p.

41035902 2028316 Fletcher, D. (1989) Prometryn Technical: Toxicity and Reproduction Study in Bobwhite Quail: Study No. 87 QR 23. Unpublished study prepared by Bio

- Life Associates, Ltd. 120 p.

43370401 Response
to the
Review Peters, G. (1994) Response to the Review of: Pr ometryn Technical: Toxicity and Reproduction Study in Bobwhite Quail: Lab Project Number: 87/QRP/23. Unpublished study prepared by Ciba Crop Protection. 61 p.

43370402 Response
to the
Review Peters, G. (1994) Response to the Review of: Prometryn Technical: Toxicity and Reproduction Study in Mallard Ducks: Lab Project Number: 87/DRP/21. Unpublished study prepared by Ciba Crop Protection. 67 p.

### 48 44556801 2028328 Gallagher, S.; Beavers, J.; Jaber, M. (1998) Prometryn Technical: A Repr oduction Study with the Northern Bobwhite (Colinus virginianus): Lab Project Number: 108

- 387: 14

- 97. Unpublished study prepared by Wildlife International, Ltd. 159 p.


## 72

- 1 Acute Toxicity to Freshwater Fish

MRID DOC# Citation Reference

70686 2028297
2028299
2028300 Beliles, R.P.; Scott, W.; Knott, W. (1965) Prometryne: Safety Evaluation on Fish and Wildlife (Bobwhite Quail, Mallard Ducks, Rainbow Trout, Sunfish

, Goldfish ). (Unpublished study received Dec 29, 1977 under 100

- 542; prepared by Woodard Research Corp., submitted by Ciba

- Geigy Corp., Greensboro, N.C.;
CDL:232551

- B)

121154 2028304 or
TN 256 in
Fed Lab Studies McCann, J. (1970) ?Caparol 80W

-- Rainbow Trout|: Test No. 256. (Unpublished study received Apr 11, 1970 under 100

- 471; pre

pared by U.S. Agricultural Research Service, Pesticides Regula

tion Div., Animal Biology Laboratory, submitted by U.S. Environ

mental Protection Agency, Beltsville, MD; CDL:129837

- A)

121155 2028305 or
TN 387 in
Fed Lab Studies McCann, J. (1971) (Caparol 80W

-- Bluegill): Test No. 387. (Unpub

- lished study received Aug 7, 1971 under 100

- 471; prepared by U.S. Agricultural Research Service, Pesticides Regulation Div., Animal Biology Labor atory, submitted by U.S.
Environmental Pro

- tection Agency, Beltsville, MD; CDL:129837

- B)


## 72

- 2 Acute Toxicity to Freshwater Invertebrates

MRID DOC# Citation Reference

70146 2028296 Vilkas, A.G. (1977) Acute Toxicity of Prometryn

-- FL

- 761355 to the Water Flea (~Daphnia magna~Straus): UCES Proj. # 11506

- 04

- 04. (Unpublished study received Dec 29, 1977 under 100

- 542; prepared by Union Carbide Corp., submitted by Ciba

- Geigy Corp., Greens

- boro, N.C.; CDL:232551

- D)


## 72

- 3 Acute Toxicity to Estuarine/Marine Organisms

MRID DOC# Citation Reference

27094 2028291 Lowe, J.I. (1964) Gulf Shellfish: Effects of Pesticides. (Unpub

lished study including letter dated Jul 28, 1964 from J.I. Lowe to H.E. Fairchild, received Jul 28, 1964 under unknown admin. no.; prepared by U.S. Fish and Wildlife Service, Bureau of Com

m ercial Fisheries, submitted by Ciba

- Geigy, Greensboro, N.C.;
CDL:131211

- A)

40228401 SEE GulBreeze Studies Spot, Oyster and Pink Shrimp

supplemental data

40573717 2028310 Surprenant, D. (1988) Acute Toxicity of Prometryn Technical to Sheepshead Minnow (Cyprinodon variegatus): Laboratory Study
No. 87

- 12

- 2588. Unpublished study prepared by Springborn Life

### 49 Sciences, Inc. 49 p.

40573718 2028311 Surprenant, D. (1988) Acute Toxicity of Prometryn Technical to Mysid Shrimp (Mysidopsis bahia): Laboratory Study No. 88

- 1

- 2601. Unpublished study prepared by Springborn Life Sciences, Inc. 52 p.

40573719 2028312 Surprenant, D. (1988) Acute Toxicity of Pr ometryn Technical to Embryos

- larvae of the Quahog Clam (Mercenaria mercenaria):
Lab

- oratory Study No. 88

- 1

- 2626. Unpublished study prepared by Springborn Life Sciences, Inc. 46 p.

70147 Wright, L., Jr.; Beliles, R.P. (1966) Prometryne: The Effect on
Sh ell Growth in Oysters. (Unpublished study received Dec 29,
1977 under 100

- 542; prepared by Woodard Research Corp., sub

mitted by Ciba

- Geigy Corp., Greensboro, N.C.; CDL:232551

- E)


## 72

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

MRI D DOC# Citation Reference

24738 2028290 McCann, J.A. (1970) ?Primaze 80W: Toxicity to Rainbow Trout|. (U.S. Agricultural Research Service, Pesticides Regulation Div., Animal Biology Laboratory, unpublished report.)

40692 2028295 McCann, J.A. (1970) Primaze 80 W: Bluegill (~?Lepomis macro?

- chirus?~): Test No. 229. (U.S. Agricultural Research Service, Pesticides Regulation Div., Animal Biology Laboratory, unpub

lished study; CDL:129814

- A)

40573720 2028313 Surprenant, D. (1988) T he Chronic Toxicity of Prometryn Technical to Daphnia magna under Flow

- through Conditions: Laboratory Study No. 88

- 1

- 2622. Unpublished study prepared by Springborn Life Sciences, Inc. 79 p.

40573721 2028314 Humaker, T. (1985) Flow

- through Fathead Minnow Early Life Stage Toxicity Test with Prometryn: Laboratory Study No. D187. Unpublished study prepared by Environmental Research & Technology, Inc. 160 p.

43370403 Response
to the
Review Peters, G. (1994) Response to the Review of : The Chronic Toxicity of Prometryn Technical to Daphnia Magna under Flow

Through Conditions. Unpublished study prepared by Ciba Crop Protection. 216 p.

43801702 2028324 Graves, W.; Mank, M.; Swigert, J. (1995) An Early Life

- Stage Toxicity Test with the Fathead Minnow (Pimephales promelas): Prometryn: Lab Project Number: 108A

- 162. Unpublished study prepared by Wildlife International, Ltd. 70 p.

44031101 See
43801702
above Graves, W.; Mank, M.; Swigert, J. (1996) An Early Life

- Stage Toxicity Test with the Fathead Minnow, Pimephales promelas: Prometryn : A Supplement : Lab Project Number: 108A

- 162. Unpublished study prepared by Wildlife International, Ltd. 11 p.


## 122

- 1 Seed Germination/Seedline Emergence and Vegetable Vigor

### 50 MRID DOC# Citation Reference

40457504 2028307 Cunez, V. (1987) Prometryn Nontarget Phytotoxicity Study: Seed Germination/Seedling Emergence Tier 1: Lab Study Number
LR87

- 24A2. Unpublished study performed by Pan Agricultural Labs. 65 p.

40457505 2028308 Cunez, V. (1987) Prometryn Nontarget Phytotoxicity Study: Vegetative Vigor Tier 1: Study Number LR87

- 24A1. Unpublished study performed by Pan Agricultural Labs. 51 p.


## 122

- 2 Aquatic plant growth

MRID DOC# Citation Reference

40457506 2028309 Hughes, J. (1987) The Toxicity of Prometryn Technical to Selenastrum capricornutum: Study Number 0267

- 38

- 1100

- 1. Unpublished study performed by Malcolm Pirnie, Inc. 71 p.


## 123

- 1 Seed germination/seedling emergence and vegitative vigor

MRID DOC# Citation Reference

41035903 2028317 Canez, V. (1988) Prometryn: Nontarget Phytotoxicity Test: Vegeta

- tive Vigor Tier II: Study No. LR 88

- 13A. Unpublished study pre

- pared by Pan

- Agricultural Labs, Inc. 177 p.

41035904 2028318 Canez, V. (1988) Prometryn: Nontarget Phytotoxicity Test: Seed Germination/Seedling Emergence Tier 2: Study No. LR 88

- 13B. Un

- published study prepared by Pan

- Agricultural Labs, Inc. 228 p.


## 123

- 2 Aquatic plant growth

MRID DOC# Citation Reference

42520901 2028319 Hughes, J.; Alexander, M. (1992) The Toxicity of Prometryn Technical to Laemna gibba G3: Lab Project Number: B267

- 577

- 4. Unpublished study prepared by Malcolm Pirnie, Inc. 36 p.

42520902 2028320 Hughes, J.; Alexander, M. (1992) The Toxicity of Prometryn Technical to
Anabaena flos

- aquae: Lab Project Number: B267

- 577

- 1. Unpublished study prepared by Malcolm Pirnie, Inc. 38 p.

42520903 2028309
2028321 Hughes, J. (1987) The Toxicity of Prometryn Technical to Slenastrum Capricornutum: Lab Project Number: 0267

- 38

- 1100

- 1. Unpublished study prepared by Malcolm Pirnie, Inc. 73 p.

42620201 2028322 Hughes, J.; Alexander, M. (1992) The Toxicity of Prometryn Te chnical to Navicula pelliculosa: Lab Project Number: B267

- 577

- 2. Unpublished study prepared by Malcolm Pirnie, Inc. 35 p.

### 51 

## NON Guideline Listings

21912 Open lit Coupland, R.T.; Skoglund, N.A. (1962) Response of native grasses to various herbicides, 1962. Pages 124

- 125,~In~Research Report for the National Weed Committee, Western Section: Volume 9. Edmon

- ton, Alberta: Natl. Weed Comm.; Pages 84

- 85,~In~19th Annual R esearch Report for the North Central Weed Control Conference; Dec 3

- 5, 1962, St. Paul, Minn. N.P. (Univ. of Saskatchewan, Dept. of Plant Ecology, Contribution # 340; also~In~unpublished submission received Sep 10, 1968 under 876

- 29; submitted by Velsicol C hemical Corp., Chicago, Ill.; CDL:005055

- A)

93171 Open lit Sobieszczanski, J. (1968) The influence of different herbicides upon the growth and development of cellulolytic microorganisms. Annales de L'Institut Pasteur 115(4):113

- 116. (Also~In~unpub

- lishe d submission received Mar 27, 1972 under 8F0643; submitted by Stauffer Chemical Co., Richmond, Calif.;
CDL:095055

- AK)



## Ecological Effects Studies Obtained from the ECOTOX Database

Avian Single Dose Oral Toxicity

Ecoref No. Citation Reference

13154 

### Marchini, S., L. Passerini, D. Cesareo, and M.L. Tosato. 1988. Herbicidal Triazines: Acute Toxicity on Daphnia, Fish, and Plants and Analysis of its Relationships with
Structural Factors. Ecotoxicol. Environ. Saf. 16(2):148

- 157

Aquatic plant growth

Eco ref No. Citation Reference

7485 Hawxby, K., Tubea, B., Ownby, J., and Basler, E. (77). Effects of Various Classes of Herbicides on Four Species of Algae. Pestic.Biochem.Physiol. 7: 203

- 209.

8628 Liu, L. C. and Cendeno

- Maldonado, A. (74). Effects of Fluometuron, Prometryne, Ametryne, and Diuron on Growth of Two Lemna Species. J.Agric.Univ.P.R. 63: 483

- 488.

15077 Gaggi, C., Sbrilli, G., El Naby, A. M. H., Bucci, M., Duccini, M., and Bacci, E. (95). Toxicity and Hazard Ranking of s

- Triazin e Herbicides Using Microtox, Two Green Algal Species and a Marine Crustacean.
Environ.Toxicol.Chem. 14: 1065

- 1069.

61983 Ma, J., Liang, W., Xu, L., Wang, S., Wei, Y., and Lu, J. (2001). Acute Toxicity of 33 Herbicides to the Green Alga Chlorella pyrenoidosa.
Bull.Environ.Contam.Toxicol. 66: 536

- 541.

62304 Faust, M., Altenburger, R., Backhaus, T., Blanck, H., Boedeker, W., Gramatica, P., Hamer, V., Scholze, M., Vighi, M., and Grimme, L. H. (2001). Predicting the Joint Algal Toxicity of Multi

- Component s

Triazine Mixtures at Low

- Effect Concentrations of Individual Toxicants.

### 52 Aquat.Toxicol. 56: 13

- 32.

65938 Ma, J., Xu, L., W ang, S., Zheng, R., Jin, S., Huang, S., and Huang, Y. (2002). Toxicity of 40 Herbicides to the Green Alga Chlorella vulgaris. Ecotoxicol.Environ.Saf. 51: 128

- 132

71458 Ma, J., Lin, F., Wang, S., and Xu, L. (2003). Toxicity of 21 Herbicides
to the Green A lga Scenedesmus quadricauda.
Bull.Environ.Contam.Toxicol. 71: 594

- 601.

78497 Grossmann, K., Berghaus, R., and Retzlaff, G. (1992). Heterotrophic Plant Cell Suspension Cultures for Monitoring Biological Activity in Agrochemical Research. Comparison wit h Screens Using Algae, Germinating Seeds and Whole Plants. Pestic.Sci. 35: 283

- 289.

81431 Drost, W., Backhaus, T., Vassilakaki, M., and Grimme, L. H. (2003). Mixture Toxicity of s

- Triazines to Lemna minor Under Conditions of Simultaneous and Sequential Exposure. Fresenius Environ.Bull. 12:
601

- 607.

105114 Liebig, M., Schmidt, G., Bontje, D., Kooi, B. W., Streck, G., Traunspurger, W., and Knacker, T. (2008). Direct and Indirect Effects of Pollutants on Algae and Algivorous Cilitaes in an Aquatic Indoor
Microcosm. Aquat.Toxicol. 88: 102

- 110.



## 72

- 2 Acu te Toxicity to Freshwater Invertebrates

Ecoref No. Citation Reference

118745 Ralston

- Hooper,K., J. Hardy, L. Hahn, H. Ochoa

- Acuna, L.S. Lee, R. Mollenhauer, and M.S. Sepulveda. ( 2009 ) . Acute and c hronic t oxicity of

a trazine and i ts m etabolites d eethylatrazine and d eisopropylatrazine on

a quatic o rganisms. Ecotoxicology18(7): 899

- 905.

### 53 

# 10. APPENDICIES

Appendix A: Prometryn Use and Usage Information Appendix B: Prometryn Fate and Transport Properties Appendix C: Output from the SIP and STIR Models Appendix D: EIIS Incident Report

### 54 

# 10.1 Appendix A: Prometryn Use and Usage Information

10.1.1 Use Information

Caparol 4L (Registration No. 100

- 620, Syngenta): Cotton; Carrot, Celeriac, Cilantro, (Celery, Chinese celery, Florence fennel), Okra, Parsley, Pigeon Peas (Puerto Rico Only),
Rhubarb Suprend Herbicide (Registration No. 100

- 1163, Syngenta): Cotton
Cotton

- Pro (Registration No. 66222

- 116, Makhteshim Agan): Cotton, Celery, Parsley, Prometryn 4 L(Registration No. 66222

- 15, Makhteshim Agan): carrot, Celeriac, cilantro, cotton, dill, leafy petiole (cardoon celery Chinese, celery celtuce, Florence, fennel, rhubarb, Swiss chard) okra, parsley, and pigeon peas Prometryne 4 L (Registration No. 34704

- 692, Loveland Products): Cotton, Celery, Dill (C A only) Prometryne 4 L (Registration No. 9779

- 297, Winfield Solutions): Cotton, Celery

Detailed use information for all registered crops is given below in cotton Tables A

- 1 to A

- 4

.

Table A

- 1 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weeds: Caparol TM 

### 4L Herbicide (Registration No. 100

- 620, Syngenta)

Use Site Soil/Weeds/Crop Restrictions Application Parameters: MSR and MYR; MNA; MAI (days); Application Methods and
Others 1

MSR MNA MYR MAI Notes & Restrictions
A. Pre

- plant 4” Incorporated:

AZ, CA and NM only * Sand and loamy sand soils Do not Apply

* AZ and CA only on sandy loam soils 1.60 1 1.60 N/A Low rate= 1.20 lb a.i/A

* NM only on sandy loam and loam soils 1.60 1 1.60 N/A Only one rate

* AZ, CA and NM only on silt loam and clay soils 2.40 1 2.40 N/A Only one rate

(B) Pre

- emergence (At or shortly after crop planting):

(1) Mid

- South and
Southeast* * Sandy loam 2.00 1 2.00 N/A Low rate= 1.60 lb a.i/A

* Silt and clay loam 2.40 1 2.40 N/A

* AR only on Sharkey clay soils 2.80 1 2.80 N/A

(2) Mississippi
River Delta in MS * Sandy loam soils 2.40 1 2.40 N/A Low rate= 2.00 lb a.i/A

* Silt and clay loam soils 2.80 1 2.80 N/A

* Sharkey clay soils Do not use

(3) Blacklands** * Loam soils 1.20 1 1.20 N/A

* Clay soils 2.40 1 2.40 N/A

(4) Rio Grande Valley of TX * Loam soils 1.60 1 1.60 N/A

* Clay soils 2.40 1 2.40 N/A

(5) High/rolling
Plains and Edwards
Plateau*** * Sand and loamy sand soils Do not use

For NM , Apply either this application or the Pre

plant 4” incorporated:, above, Not both * Sandy loam soils 0.80 1 0.80 N/A

* Loam and sandy clay loam soils 1.20 1 1.20 N/A

Other clay soils 1.60 1 1.60 N/A

(6) AZ and CA Do not use

(7) All Regions Do not use on the following soils: sand or loamy sand , or on shallow soils with caliche below or at soil surface

### 55 C. Pre

- Emergence Reduced Rate Application

Regions 1 to 6,
above Sandy loam soils 0.75 1 0.75 N/A A Pre

- emergence reduced rate application (At or shortly after crop planting) which is to be followed by application of other post emergence herbicides usually within a period of 30 or more days Loam, silt, sandy clay loams & clay loam soils 1.00 1 1.00 N/A

Clay soils 1.00 1 1.00 N/A D. Winter and Early Spring Weed Control

AL, AR, LA, Mo,
MS and TN * After bedding (from November 1 until 14 days before planting cotton) 1.00 1 1.00 N/A Only one of the applications Not both and application may be made before or after weeds emerge preferably <2” high * After bedding (from January 1 until 30 days before planting cotton) 0.75 1 0.75 N/A E. Winter Weed Control

TX Gulf Coast and
Black lands of TX * Winter application for bedded land to be planted cotton in the following spring OR * Fall application for bedded land to be planted cotton in the following spring 0.80 1 0.80 N/A Only one of the applications Not both and application may be made before weeds emerge. Low rate= 0..60 lb
a.i/A

F. Pre

- Emergence Or Post

- Emergence Winter Application for Bedded Land to be Planted Cotton

California * Sandy loam soil 1.6 1 1.60 N/A Pre

- emergence Rainfall or sprinkler irrigation is

necessary Post

- Emergence Apply to weeds less than 2” tall. * Medium or fine soil 2.4 1 2.40 N/A

* Sand, loamy sand, salt affected or calcareous soils Do not use G. Post

- Emergence directed

(1) AR, LA, MO, MS, TN and TX Minimum cotton plant Height = 3

- 6” and maximum weed Height= <1” 0.5 1 0.5 N/A Precautions: * Prevent contact of the spray with cotton leaves; * Use precision application equipment so the spray is accurately directed to the base of the cotton plants and still thoroughly covers the soil and weeds beneath the cotton plants (Use leaf lifters or shi elds); * Apply only when all cotton plants have exceeded the minimum recommended height; * Apply to level, well prepared surfaces. * Do not apply to furrow

- planted cotton until furrows are leveled (plowed in); and
* Do not treat cotton under stress (2) All cotton regions Minimum cotton plant Height = >6” and maximum weed Height= <2” 0.7 1 0.7 N/A H. Chemical Hoe (Emerged weeds only)

All cotton regions Minimum cotton plant Height = 3

- 6” 0.5 3 1.5 NS Precautions:
* In cotton 3

- 6 inches tall, be extremely careful to avoid spray contact with cotton leaves by applying Caparol 4L with a precision applicator equipped with fenders or shields, * In cotton <10” tall, apply only if cotton is bedded or
flat

- planted. Minimum cotton plant Height = 3

- 6” and maximum weed Height= <1” 0.7 3 2.1 NS I. Lay

- by application (cotton at least 12” high)

(1) Mid

- South and
Southeast Sandy soil 1.2 2 2.4 NS

Loam soil 1.4 2 2.8 NS

Clay soil 1.6 2 3.2 NS

(2) Black lands of
OK and TX Loam soil 0.8 2 1.6 NS

Clay soil 1.6 2 3.2 NS

(3) High Plains of
NM and TX Sandy soil 0.8 2 1.6 NS

Loam and Clay soil 1.2 2 2.4 NS

(4) Southeast TX Loam soil 1.2 2 2.4 NS

Clay soil 1.6 2 3.2 NS

(5) AZ and CA Sandy Loam and Loam 1.6 2 3.2 NS

(6) All Regions Plant height: cotton >6” and Weeds <2”) 0.65 3 2.0 NS

(7) Rio Grande Valley of TX and Coachella Valley of CA Do not use

### 56 Table A

- 2 Use Patterns for Prometryn on cotton for selective control of annual broadleaf and grass weeds: C otton

- Pro ® 

### (Registration No. 66222

- 116, Makhteshim Agan); Prometryn 4 L(Registration No. 66222

- 15, Makhteshim Agan); Prometryne 4 L (Registration No. 34704

- 692, Loveland Products), and Prometryne 4 L (Registration No.

9779

- 297, Winfield Solutions) Abbreviations: N/A= Not applicable; NS: Not specified, the registrant is requested to supply the information and include it in the label;
MSR= Maximum Single Rate; MNA= Maximum number of applications; MYR= Maximum yearly rate; ; MAI= Minimum application intervals; * O ther than the Mississippi River Delta in MS ; ** Black lands of OK and TX, TX Gulf Coast, and TX Coastal Bend; *** of TX, Southeast TX and NM

and KS

Use Site Soil/Weed s/Crop Restrictions Application Parameters: MSR and MYR; MNA; MAI (days); Application Methods and
Others 1

MSR MNA MYR MAI Notes & Restrictions (A) Pre

- plant (before planting cotton) (Cotton Pro & Prometryn 4L)

(1) Mid

- South and Southeast, other than Mississippi river
delta in MS Sandy loam soil 2.0 1 2.0 N/A

Do not use on sand or loamy sand or shallow soils with
caliche sub

- soils or in areas with caliche outcroppings. Rainfall or irrigation is needed following application to
obtain weed control

In Ne w Mexico, apply either pre

- plant incorporated or

pre

- emergence (not both); Can be aerially applied Silt and Clay loam Soil 2.4 1 2.4 N/A

Sharkey clay Do not Use

(2) Mississippi River
Delta in MS Sandy Loam Soil 2.4 1 2.4 N/A

Silt and Clay loam Soil 2.8 1 2.8 N/A

Sharkey clay Do not Use (3) Black lands of TX, OK, TX Gulf
coast and YTX
Coastal Bend Loam soil 1.2 1 1.2 N/A

Clay soil 2.4 1 2.4 N/A

(4) Rio Grande Valley of Texas Loam soil 1.6 1 1.6 N/A

Clay soil 2.4 1 2.4 N/A

(5) High Plains, Rolling Plains and
Edwards Plateau of TX, Southwest TX
and New Mexico Sandy, Loamy sand Do not Use

Sandy loam soil 0.8 1 0.8 N/A

Loam, sandy clay loam soil 1.2 1 1.2 N/A

Other clay soils 1.6 1 1.6 N/A

(6) AZ and CA Do not use (B) Pre

- plant 4” incorporated (Cotton Pro; Prometryn 4L; Prometryne 4 L/Loveland & Winfield )

(1) AZ, CA and NM Silt loam and clay soil 2.4 1 2.4 N/A Broadcast or band treatment. If broadcast, treat the flat soil surface prior to listing. If banded, apply over partially finished or finished beds. Incorporate up to 4” deep immediately after application. In AZ and CA Sandy and loam soils , the Low rate= 1. 2. In New Mexico, apply either pre

- plant incorporated or pre

emergence (not both); Can be aerially applied; Can be aerially applied Sand and loamy sand soils Do not use

(2) AZ and CA Sandy loam soils 1.6 1 1.6 N/A

(3) NM Sandy loam and loam soils 1.6 1 1.6 N/A (C) Pre

- emergence (at planting or shortly after planting) (Cotton Pro & Prometryn 4L; Prometryne 4 L/Loveland & Winfield )

Regions 1 to 6, Above Rates and sites are the same as stated for Pre

- plant application, above ; except for Prometryne 4 L/Loveland formulation that can be used in Sharkey clay soils in AR Only Rainfall or irrigation is needed following pre

emergence application to obtain weed control. Do not apply a second pre

- emergence application. If aerially applied, avo id spray overlap, as crop injury may result; Can be aerially applied Sand or loamy sand, shallow soils with caliche sub

soils or in areas with caliche outcroppings Do not Use (D) Post

- emergence Directed: Chemical Hoe ( C otton

- Pro; Prometryn 4L; Prometryne 4 L/Loveland & Winfield )

AR, LA, MS, MO, TN and TX, and All regions In AR, LA, MS, Mo, TN and TX (Plant height:
cotton 3

- 6” and Weeds <1”) 0.5 3 1.5 NS No aerial application. Prevent contact of the spray with cotton leaves or injury may occur. Use precision application equipment so the spray is accurately directed to the base of the cotton plants and still

### 57 In All Regions (Plant height: cotton >6” and Weeds <2”) 0.65 3 2.0 NS thoroughly covers the soil and weeds beneath the cotton plants. Use leaf lifters or shields. Apply only when all plants have exceeded the minimum recommended height. Do not apply to furrow

- planted
cotton until furrows are leveled (plowed in). Do not treat cotton under stress from drought, cultivator
dam age or fertilizer application (E) Post

- emergence Directed: Lay

- By (emerged/germinating weeds) ( C otton

- Pro & Prometryn 4L; Prometryne 4 L/Loveland &
Winfield )

(1) Mid

- South and
Southeast Sandy soils 1.2 1 1.2 N/A

No aerial application; When cotton crop is at least 12” tall and weeds<2” tall Loam soils 1.4 1 1.4 N/A

Clay soils 1.6 1 1.6 N/A

(2) Black lands of TX
and OK Loam soils 0.8 1 0.8 N/A

Clay soils 1.6 1 1.6 N/A

(3) High Plains of TX
and NM Sandy soils 0.8 1 0.8 N/A

Loam and Clay soils 1.2 1 1.2 N/A

(4) Southwest TX Loam soil 1.2 1 1.2 N/A

Clay soil 1.6 1 1.6 N/A

(5) Rio Grande Valley of TX Do not Use (6) AZ and CA (Do
not use in the Coachella valley) Sand and Loamy sand soils Do not Use

Sandy loam and Loam soils 1.6 1 1.6 N/A (F) Winter Weed Control ( C otton

- Pro)
(1) AR, LA, MS, and

TX 0.8 1 0.8 N/A Apply in fall or winter to land that will be planted to cotton the following spring Apply before weed emerge or post emergence when weeds are <2” tall for most weeds or up to 4

- 6” tall for henbit (purple top). Allow 21 days between this application and pre

- emergence application (2) CA Sandy loam soils 1.6 1 1.6 N/A

Medium or Fine soils 2.0 1 2.0 N/A

Sandy and Loamy sand soils Do not Use

(G) Winter Weed Control (Prometryn 4L; Prometryne 4 L/Loveland & Winfield )

(1) AL, AR, LA, MO, MS, and TN Applied after bedding from Nov, 1 until 30 days before planting cotton 1.00 1 1.0 N/A Winter and early spring before or after weeds germinate preferably <2” tall. Applied after bedding from Nov, 1 until 30 days before planting cotton 0.75 1 0.75 N/A (2) TX Gulf coast and
Black lands of TX Apply in the fall or winter to land that will be planted cotton in the spring 0.8 1 0.8 N/A Fall or winter before weeds reaches 4

- 6” tall

(2) CA Sandy loam soils 1.6 1 1.6 N/A

Apply after bedding either pre

- emergence or Post

- emergence to weeds less than 2 inches tall Medium or fine texture soils 2.0 1 2.0 N/A

Sandy and Loamy sand soils Do not Use

Abbreviations: N/A= Not applicable; NS: Not specified, the registrant is requested to supply the information and include it in the label;
MSR= Maximum Single Rate; MNA= Maximum number of applications; MYR= Maximum yearly rate; ; MAI= Minimum application intervals;

### 58 Table A

- 3 Use Patterns for Prometryn on Other Crops ( Ground spray for all crops except Pigeon Peas “ground/aerial; Chemigation for applications on celeriac, celery/leafy petiole

crop group s)

Crop Product Application Type (Site) Soil/Weeds/Crop Restrictions Application Parameters: MSR and MYR; MNA; MAI (days); Application
Methods and Others 1

MS

R MNA MYR MAI Notes & Restrictions

Carrot Ca parol 4L
And Prometryn
4L Pre

- emergence of

crop; Plus Not specified 2.0 1 2.0 N/A Maximum 4 lb a.i./A/crop cycle Interval NS between the two post

emergence applications Post

- emergence of crop through the 6 leaf stage Not specified 1.0 2 2.0 NS

Celeriac Caparol 4L Transplants after the crop has 6

- 8
leaves Or Coarse textured/low OM soils 0.8 1 0.80 N/A

Maximum 2 lb a.i./A/crop cycle Fine textured/high OM soils 2.0 1 2.0 N/A Prometryn
4L Post

- emergence up to 6

- 8 leaf stage Not specified 2.0 1 2.0 N/A

Celery Prometryne
4L (Loveland ) To Seedbeds (FL) Coarse textured/low OM soils 0.6 1 0.60 N/A

Fine textured/high OM soils 0.8 1 0.80 N/A

To Direct seeded crop/ Pre crop emergence (CA) Or Coarse textured/low OM soils 1.2 1 1.2 N/A

Fine textured/high OM soils 1.6 1 1.60 N/A

To Direct seeded crop/ Post crop emergence (CA) Coarse textured/low OM soils 0.8 1 0.80 N/A

Fine textured/high OM soils 1.0 1 1.0 N/A

Sand or loamy sand soils Do not use

Pre

- transplant, Split Pre & post

Transplant, Or Post Transplant (CA) Coarse textured/low OM soils 1.6 1 1.6 N/A

Applications: (1) Pre

- transplant: Up to 21 days prior to transplant;
Or (2) Split Pre & post

- transplant: Pre

transplant as above plus post

transplant during the 2

- 6 week period after transplanting and weeds <2” tall
Or (3) Post

- transplant during the 2

- 6 week period after transplanting and
weeds <2” tall

Maximum pre & post applications
should not exceed the maximum
allowable rates stated in the column
to the left Fine textured/high OM soils 2.0 1 2.0 N/A

Pre

- transplant, Split Pre & post

Transplant, Or Post Transplant (FL) Coarse textured/low OM soils 0.8 1 0.80 N/A

Fine textured/high OM soils 1.6 1 1.6 N/A

Sandy or Muck soils 1.6 1 1.6 N/A

Pre

- transplant, Split Pre & post

Transplant, Or Post Transplant (HI) Coarse textured/low OM soils 2.4 1 2.4 N/A

Fine textured/high OM soils 3.2 1 3.2 N/A

Pre

- transplant, Split Pre & post

Transplant, Or Post Transplant (MI) Coarse textured/low OM soils 1.0 1 1.0 N/A

Fine textured/high OM soils 2.0 1 2.0 N/A

Muck 2.0 1 2.0 N/A

Pre

- transplant, Split Pre & post

Transplant, Or Post Transplant (WI) Coarse textured/low OM soils 1.6 1 1.6 N/A

Fine textured/high OM soils 2.0 1 2.0 N/A

Cotton

- Pro; Prometryne 4L (Agri

solutions) To Seedbeds (FL) Coarse textured/low OM soils 0.6 1 0.60 N/A

Apply 7 days after seed bed covers are
removed @ 2

- 5 true leaves celery
stage Fine textured/high OM soils 0.8 1 0.80 N/A Not specified in Prometryne 4LAgri

- solutions Label) 0.8 1 0.80 N/A

To Direct seeded Coarse textured/low OM soils 1.2 1 1.2 N/A Apply at or shortly after planting

### 59 crop/ Pre crop emergence (CA) Or Fine textured/high OM soils 1.6 1 1.60 N/A before crop emerges; Don’t apply if crop under water stress. Apply Pre Or Post crop emergence Not both

To Direct seeded crop/ Post crop emergence (CA) Coarse textured/low OM soils 0.8 1 0.80 N/A Apply @ 2

- 5 true leaves celery stage
and weeds<2” tall. Don’t apply if crop
under water stress. Weeds <2” tall Apply Pre Or Post crop emergence
Not both Fine textured/high OM soils 1.0 1 1.0 N/A
Sand or loamy sand soils Do not use

To Transplanted Crop (CA and TX) Coarse textured/low OM soils 1.6 1 1.6 N/A

Apply before weeds are 2” tall during
the 2

- 6 weeks after planting Fine textured/high OM soils 2.0 1 2.0 N/A

To Transplanted Crop (FL) Coarse textured/low OM soils 0.8 1 0.80 N/A

Fine textured/high OM soils 1.6 1 1.6 N/A

Sandy or Muck soils 1.6 1 1.6 N/A

To Transplanted Crop (HI) Coarse textured/low OM soils 2.4 1 2.4 N/A

Fine textured/high OM soils 3.2 1 3.2 N/A

To Transplanted Crop (MI and OH) Coarse textured/low OM soils 1.0 1 1.0 N/A

Fine textured/high OM soils 2.0 1 2.0 N/A

Muck 2.0 1 2.0 N/A

(8)To Transplanted Crop (WI) Coarse textured/low OM soils 1.6 1 1.6 N/A

Fine textured/high OM soils 2.0 1 2.0 N/A

Celery,
Chinese celery and
Florence
fennel Caparol 4L
And Prometryn
4L To Seedbeds (FL) All soils 0.8 1 0.80 N/A After crop has 2

- 5 true leaves and 7 days after covers are removed from
seedbeds

To Direct seeded crop/ Pre

- crop

emergence Or Coarse textured/low OM soils 1.2 1 1.2 N/A At planting or shortly after planting
Do not combine with post crop emergence application Fine textured/high OM soils 1.6 1 1.60 N/A

To Direct seeded crop/ Post crop

emergence Coarse textured/low OM soils 0.8 1 0.80 N/A After crop has 2

- 5 true leaves and
before weeds 2” tall Do not combine with pre

- crop emergence application Fine textured/high OM soils 1.0 1 1.0 N/A

Sand and loamy sand soils Do not use To Transplanted Crop (FL) Sandy or muck 1.6 1 1.60 N/A

Apply 2 to 6

- week period after transplanting Split application is permitted; however, Application intervals were not specified (?) To Transplanted Crop (AZ, CA and TX) Coarse textured/low OM soils 1.6 1 1.60 N/A

Fine textured/high OM soils 2.0 1 2.0 N/A To Transplanted Crop (MI and OH) Fine textured or muck 2.0 1 2.0 N/A To Transplanted Crop (WI) Fine textured 2.0 1 2.0 N/A

Cilantro Caparol 4L Post

- planting /Pre

emergence of crop Coarse textured/low OM soils 1.0 1 1.0 N/A

Maximum 1.6 lb a.i./A/crop cycle Fine textured/high OM soils 1.6 1 1.6 N/A Prometryn
4L Post

- planting /Pre

emergence of crop Not specified 1.6 1 1.6 N/A

Dill Prometryn
4L And Prometryne
4L (Loveland) Pre

- emergence Or Not specified 1.6 1 1.6 N/A

Pre

- emergence Or Post

- emergence Not both. Don’t apply if crop under water

stress Post

- emergence before weeds 2” tall Not specified. Use on sand or loamy sand soils may cause crop injury 1.6 1 1.6 N/A

Leafy

Petiole 1 Prometryn
4L Seed bed (FL) Not specified 0.8 1 0.80 N/A After the crop has 2

- 5 true leaves and 7 days after seedbed cover is removed Direct seeded crop (CA and AZ) Pre

emergence Or Coarse textured/low OM soils 1.2 1 1.2 N/A

Post

- emergence = after the crop has 2

- 5
true leaves Fine textured/high OM soils 1.6 1 1.60 N/A Direct seeded crop (CA and AZ) Post

emergence Coarse textured/low OM soils 0.8 1 0.80 N/A

Fine textured/high OM soils 1.0 1 1.0 N/A Direct seeded crop (CA and AZ) Sand and loamy sand soils Do not use

Okra Caparol 4L Pre

- emergence Or Not specified 1.5 1 1.50 N/A Pre

- emergence= after planting before

### 60 10.1.2. Usage Information

Screening Level Usage Analysis (SLUA) for Prometryn
Date: September 10, 2012

What is a Screening Level Usage Analysis (SLUA)?

• Available estimates of pesticide usage data for a particular active ingredient
that is used on agricultural crops in the United States.

• Pesticide usage data obtained from various sources. The data are then merged, averaged, and rounded so that the present ed information is not proprietary, business confidential, or trade secret.
What does it contain?

• Pesticide usage data for a single active ingredient only.

• Agricultural use sites (crops) that the pesticide is reported to be used on.

• Available pesticide us age information from U.S. states that produce 80% or more of a crop, in most cases, or less than 80%, in rare cases, depending on the scope of the survey and available resources.

• Annual percent of crop treated (average & maximum) for each agricultural

crop.

• Average annual pounds of the pesticide applied for each agricultural crop (i.e., for the states surveyed, not for the entire United States). What assumptions can I make about the reported data?

• Average pounds of active ingredient applied

- Values are calculated by merging pesticide usage data sources together; averaging across all And Prometryn
4L Pre

- emergence + Post

- directed Not specified 0.75 2 1.50 Refer to plant stage crop emergence Post directed= when okra plants are at

7

- 9 leaf & weeds 2” tall. Maximum 1.5/crop cycle. May not be combined

Parsley Caparol 4L; Prometryn
4L And Prometryne
4L (Loveland) Pre

- emergence: after planting but before crop emerges (CA) Coarse textured/low OM soils 1.0 1 1.0 N/A Do not apply when crop is under water

stress Fine textured/high OM soils 2.0 1 2.0 N/A

Sandy and loamy sand soils Do not use

Caparol 4L After planting (timing is stated for
the 1 st , 2 nd , and 3 rd applications in the next column (All States including CA) Fine textured/high OM soils

1 st 14 days after planting; 2 nd

30

- day prior to harvest; 3 rd to

re

- growth “after cutting” up to 30 days prior to the second cutting 0.5 3 1.5 Refer to
3 rd

Column Use lower rates (specified only for CA but not for other states?) in Coarse
textured/low OM soils

Pigeon
Peas (Puerto Rico Only) Caparol 4L
And Prometryn
4L Pre

- emergence of weeds/crop Loam soils 2.0 1 2.0 N/A

Apply at planting or immediately after planting before crop/weeds emerge Clay soils 3.0 1 3.0 N/A

Sand and loamy sand Do not use

Rhubarb Caparol 4L To dormant
established
rhubarb Coarse textured soils 1.6 1 1.60 N/A Apply before leaves have emerged
from the crown Fine textured soils 2.0 1 2.0 N/A

Abbreviations: N/A= Not applicable; NS: Not specified, the registrant is requested to supply the information and include it in the label;
MSR= Maximum Single Rate; MNA= Maximum number of applications; MYR= Maximum yearly (seasonal) rate; MAI= Minimum application intervals;

1 Leafy Petiole= ca rdoon, celery, Chinese celery, celtuce, Florence fennel, rhubarb, and Swiss chard

### 61 observations, then rounding. Note: If the estimated value is less than 500, then that value is labeled <500. Estimated values between 500 & <1,000,000
are rounded to 1 significant digit. Estimated values of 1,000,000 or greater are rounded to 2 significant digits.)

• Average percent of crop treated

- Values are calculated by merging data sources together; averaging by year, averaging across all years, & rounding to
the ne arest multiple of 5. Note: If the estimated value is less than 2.5, then the value is labeled <2.5. If the estimated value is less than 1, then the value
is labeled <1.

• Maximum percent of crop treated

- Value is the single maximum value reported across all data sources, across all years, & rounded up to the nearest multiple of 5. Note: If the estimated value is less than 2.5, then the value is
labeled <2.5.
What are the data sources used?

• USDA

- NASS (United States Department of Agriculture’s National Ag ricultural Statistics Service)

– pesticide usage data from 200 3 to 20 10

.

• Private pesticide market research

– pesticide usage data from 200 3 to 20 10

.

• California Department of Pesticide Regulation (DPR) Pesticide Use Reporting (PUR) data for 200 3 to 20 10.

Wh at are the limitations to the data?

• Additional registered uses may exist but are not included because the available surveys do not report usage (e.g., small acreage crops).

• Lack of reported usage data for the pesticide on a crop does not imply zero
usage.

• Usage data on a particular site may be noted in data sources, but not quantified . In these instances, the site would not be reported in the SLUA.

• Non

- agricultural use sites (e.g., turf, post

- harvest, mosquito control, etc.) are not reported in the SLUA. A separate request must be made to receive these
estimates.

• Some sites show some use, even though they are not on the label. This usage could be due to various factors, including, but not limited to Section 18 requests, existing stocks of the chemical, da ta collection errors, and experimental use permits (EUPs).

### 62 September 10, 2012

Screening Level Estimates of Agricultural Uses of Prometryn ( 080805 ) Sorted Alphabetically Reporting Years: 2003

- 2010

Percent Crop Ttd.

Crop Lbs. A.I. Avg. Max.

1 Carrots 3,000 <2.5 <2.5

2 Celery 40,000 85 100

3 Cotton 800,000 10 15

4 Fallow 3,000 <1 <2.5

All numbers are rounded.

<2.5 : indicates less than 2.5 percent of crop is treated.

<1 : indicates less than 1 percent of crop is treated.

SLUA data sources include:
USDA

- NASS (United States Department of Agriculture's National Agricultural Statistics Service)
Private Pesticide Market Research These results reflect amalgamated data developed by the Agency and are releasable to the public.

### 63 

# 10.2 Appendix B: Prometryn Fate and Transport Properties

Laboratory fate and transport properties of prometryn are summarized in following
Tables:

Fate properties of prometryn in biotic systems in the laboratory

Property Soil or Water/Sediment System* Degradation Products (% of Applied) Value Reference (MRID)

Classification

Aerobic Soil
Metabolism 1 Loamy Sand soil (Germany): 84% sand, 7% silt, 9% clay, 2.2% organic carbon, pH 6.5, CEC 11.3 meq/100 g Major (MAJ): GS

- 11526 (max. 27% @ termination (360 days); Minor (MIN): GS

- 11354 (max. 5% @ day 60 then declined to 1% @ termination (360 days); Mineralization (MRL): CO 2 (max. 0.5% @ termination);
Non

- extractable residues (NER): max. 31% @ termination 257 days 

### 001483

- 38

Acceptable

Aerobic Aquatic
Metabolism (total system) River System: Water: pH 8, OC 3 ppm.
Sediment: 25% sand, 57% Silt and 18% clay,
OC 3.7% and CEC= 21 MAJ: GS

- 11526 (max. 18% @ termination (268 days);

MIN:
GS

- 11354 (max. 3% @ 58 days then
declined to 1.3% @ termination
GS

- 16141 (max. 7% @ 58 days then
declined to 6% @ termination
GS

- 17794 (max. 4% @ termination
MRL: CO 2 (max. 0.5% @ termination);
NER: max. 26% @ termination 236 days 485416

- 03

Under Review 2

A erobic Aquatic
Metabolism (total system) Pond System: Water: pH 7.4, OC 5 ppm.
Sediment: 46% sand, 43% Silt and 12% clay,
OC 1.5% and CEC= 10 MAJ: GS

- 11526 (max. 18% @ termination (268 days);

MIN:
GS

- 11354 (max. 3% @ 91 days then
declined to 0.6% @ termination
GS

- 16141 (max. 6% @ 58 days then
declined to 2.8% @ termination
GS

- 17794 (max. 5% @ termination
MRL: CO 2 (max. 0.4% @ termination);
NER: max. 35% @ termination 110 days 485416

- 03

Under Review 2

Anaerobic soil
metabolism
half

- life (25 °C) Sandy loam soil (California): 60% sand, 35% silt, 5% clay, 0.7% organic carbon, pH 4.6, CEC 3.4 meq/100 g Samples were aerobically pre

- incubated for 30 days and levels of parent and un

extractable residues were determined before the anaerobic incubation step for 71 days:
Parent and un

- extractable residues were practically stable throughout the 71 days with No degradation products formed. Stable 411559

- 01 Acceptable

1 Incomplete material balance invalidated the anaerobic portion of the study;

2 Under Review : Formal review underway.

### 64 Transport properties of prometryn

Property Soil or Water/Sediment System* Degradation Products (% of Applied) Value Reference (MRID)

Classification

Soil

- water partition
coefficients (K FOC ) L/Kg Agricultural sand/Huntington Si L (88% sand, 11% silt, 1% clay, 3 meq/100g CEC, pH 7.9, and 0.6% Organic matter N/A Parent 245

418759

- 01/03 Acceptable GS

- 11354 174

GS

- 11526 186 Loamy sand/ Huntington Si L (84% sand, 13% silt, 3% clay, 7 meq/100g CEC, pH 7.7, and 1.7% Organic

matter N/A Parent 169

GS

- 11354 86

GS

- 11526 85

Silt Loam/ Amour Si L (17% sand, 66% silt, 17% clay, 16 meq/100g CEC, pH 6.5, and 3.0% Organic matter N/A Parent 116

GS

- 11354 72

GS

- 11526 84 Silty clay loam/Salvisa Si C L (15% sand, 51% silt, 34% clay, 30 meq/100g CEC, pH 6.9, and 1.2% Organic

matter N/A Parent 448

GS

- 11354 210

GS

- 11526 1,044

Laboratory Volatility at 25

o C Sandy soil (88% sand, 11% silt, 1% clay, 0.62% organic matter, pH 7.9, CEC= 3 meq/100 g) * Mean daily air concentration of 14 C prometryn ranged from 0.41 to 0.97 ug/m 3 ; * Volatility rates ranged from 9.2 x 10 - 5 to
1.1 x 10 - 4 ug/cm 2 /hr * Minimal volatility: an average of 0.99% (mean, N = 4) of the applied prometryn volatilized from the soil during the 30 day incubation period 418759

- 06 Acceptable

Fish bio

concentration and depuration Bluegill sunfish BCFs: 85x (whole fish) 54x (fillet) 110x (viscera) 73% depuration in whole fish after 14 days 410227

- 01 Acceptable

### 65 Terrestrial field studies for prometryn

Location Top Soil Characteristics Degradation Products (% of Applied)

and Leaching PDHL
(Days) 1 Reference (MRID)

Classification

Terrestrial
field dissipation

(CA planted cotton)

- Sandy loam soil: 70% sand, 18% silt, 12% clay, 0.9% OM, pH 7.4, CEC 8.4 meq/100 g

- Planted cotton: Application Rate (total= 7.8 lbs a.i/A): five weekly applications @ 0.7 to 3.1 a.i/A/Application

- Bare ground: Application Rate: one application of 6.5 lbs a.i/A Degradation Products

GS

- 11526 (max. 23% @ 7 days then declined to 2% @ termination (>1 year);
GS

- 11354 (max. 3% @ 7 days then
declined to 1% @ termination
Leaching

Parent: refer to summary below

GS

- 11526:

15

- 60 cm layer : Detected 6 to 13% of the
time @ a maxi. concentration of 4%

60

- 120 cm layer : Detected 13% of the time @ concentrations ranging from 1 to 5%

GS

- 11354: Was not detected below 15 cm 103 415464

- 01 supplemented with
422539

- 03 Acceptable

Terrestrial
field dissipation

(CA bare soil) Degradation Products

GS

- 11526 (max. 15% @ 2

- 3 months then declined to ND @ termination (>1 year);
GS

- 11354 (max. 1% throughout the study period then declined to ND @ termination
Leaching

Parent: refer to summary below

GS

- 11526:

15

- 60 cm layer : Detected 3 to 100% of the
time @ a maxi. Concentration of 5%

60

- 120 cm layer : Was not detected

GS

- 11354: Was not detected below 15 cm 71 415464

- 02 supplemented with
422539

- 04 Acceptable

### 66 Prometryn and its major/minor environmental transformation products

PARENT: Prometryn: N,N'

- diisopropyl

- 6

- rnethyIsulfanyl

- [1,3,5]triazine

- 2,4

- diamine

Smiles: C1(=NC(=NC(=N1)NC(C)C)SC)NC(C)C; CAS No.: 7287

- 19

- 6

MAJOR TRANSFORMATION PRODUCTS

Name (Code & Synonym)/ Formula/Molecular Weight (MW)
CAS No./Smiles Codes Study Type (MRID) Maximum %Applied Radioactivity “AR” (day) And % AR Following Maximum (day of Occurrence) Hydroxypropazine (GS

- 11526): 4,6

- bis

isopropylamino

- [1,3,5]triazine

- 2

- ol
Formula: C 9 H 17 N 5 O
MW: 211.26 g/mol; CAS No.: 7374

- 53

- 0
Smiles: C1(=NC(=NC(=N1)NC(C)C)O)NC(C)C Aerobic soil (001483

- 38) 27% @ 365 days with no decline Aerobic aquatic (485416

- 03) 16

- 18% @ 268 days with no decline

TFD (415464

- 01/04 Supplemented w/ 422539

- 01/04) 15

- 31% @ 14

- 90 days then declined to
No detection

- 1% @ 540

- 544 days

MINOR TRANSFORMATION PRODUCTS

Prometryn Sulfoxide ( GS

- 16141): 4,6

- bis

isopropylamino

- 2

- methanesulfinyl

- [1,3,5] triazine
Formula: C 10 H 19 N 5 SO
MW: 257.36 g/mol; CAS No.: 55702

- 48

- 2
Smiles: C1(=NC(=NC(=N1)NC(C)C)[S](C)=O)NC(C)C Aerobic soil (001483

- 38) Not Tracked Not Tracked

Aerobic aquatic (485416

- 03) 6

- 7% @ 58 days then declined to 3

- 6 % @ 268 days TFD (415464

- 01/04 Supplemented w/ 422539

- 01/04) Not detected Not detected Terrestrial
field dissipation

(TX planted

cotton)

- Silt loam soil: 18% sand, 64% silt, 18% clay, 2.1% OM, pH 7.7, CEC 13.4 meq/100 g

- Planted cotton: Application Rate (total= 6.0 lbs a.i/A): five weekly applications @ 0.5 to 3.1 a.i/A/Application

- Bare ground: Application Rate: one application of 7 lbs a.i/A Degradation Products

GS

- 11526 (max. 31% @ 14 days then declined to 1% @ termination (>1 year);
GS

- 11354 (max

. 4% @ 7 days then
declined to 1% @ termination
Leaching

Parent: refer to summary below

15

- 60 cm layer : Detected 10 to 17% of the
time @ a maxi. Concentration of 4%

60

- 120 cm layer : Was not detected

GS

- 11354: Was not detected below 15 cm 86 415464

- 03 supplemented with
422539

- 01 Acceptable

Terrestrial
field dissipation

(TX bare ground) Degradation Products

GS

- 11526 (max. 15% @ 2

- 3 months then declined to ND @ termination (>1 year);
GS

- 11354 (max. 1% throughout the study period then declined to ND @ termination
Leaching

Parent: refer to summary below

15

- 60 cm layer : Detected 10 to 12% of the
time @ a maxi. Concentration of 2%

60

- 120 cm layer : Was not detected

GS

- 11354: Was not detected below 15 cm

Parent Leaching(All studies s ummary):

15

- 60 cm layer : Detected 3 to 100% of the time @ concentrations ranging from 2 to 5%

60

- 120 cm layer : Detected 13% of the time @ concentrations ranging from 1 to 5% 70 415464

- 04 supplemented with
422539

- 02 Acceptable

1 PDHL= Parent Dissipation Half

- life: Half

- lives for the top 15 cm of the soil were calculated using linear regression; these half

lives will be recalculated using non

- linear models; ND= No detection

### 67 Des

- ethylhydroxy atrazine (GS

- 17794): 4 arnino

6

- isopropylarnino

- (1,3,5jtriazine

- 2

- ol)
Formula: C 6 H 11 N 5 O
MW: 169.19 g/mol; CAS No.: Not reported
Smiles: C1(=NC(=NC(=N1)NC(C)C)O)N Aerobic soil (001483

- 38) Not detected Not detected

Aerobic aquatic (485416

- 03) 4

- 5% @ 268 days with no decline TFD (415464

- 01/04 Supplemented w/ 422539

- 01/04) Not detected Not detected

De

- isopropyl prometryn (GS

- 11354), de

- alkyed prometryn Or De

- metylametryn): N

- lsopropyl

- 6

- methylsuIfanyl

- [1,3,5]triazine

- 2,4

- diamine)
Formula: C 7 H 13 N 5 S
MW: 199.28 g/mol; CAS No.: Not Reported
Smiles: C1(=NC(=NC(=N1)NC(C)C)N)SC Aerobic soil (001483

- 38) 1% @ 365 days with no decline

Aerobic aquatic (485416

- 03) 3% @ 58 0r 91 days then declined to 1% @ 268 days TFD (415464

- 01/04 Supplemented w/ 422539

- 01/04) 1

- 4% @ 7 days then declined to 0

- 1% at
540

- 544 days

### 68 

# 10.3 Appendix C: Output from the SIP and STIR Models

1. Output from the Screening Imbibition Program (SIP)

Table 1. Inputs

Parameter Value

Chemical name Trifloxystrobin
Solubility (in water at 25 o C; mg/L) 0.61

Mammalian LD 50 (mg/kg

- bw) 5000 Mammalian test species laboratory rat Body weight (g) of "other" mammalian species

Mammalian NOAEL (mg/kg

- bw) 50 Mammalian test species laboratory rat Body weight (g) of "other" mammalian species

Avian LD 50 (mg/kg

- bw) 5000 Avian test species northern bobwhite quail Body weight (g) of "other" avian species Mineau scaling factor 1.15

Mallard NOAEC (mg/kg

- diet) 5050 Bobwhite quail NOAEC (mg/kg

- diet) 5050 NOAEC (mg/kg

- diet) for other bird species Body weight (g) of other avian species NOAEC (mg/kg

- diet) for 2nd other bird species Body weight (g) of 2nd other avian species

Table 2. Mammalian Results

Parameter Acute Chronic Upper bound exposure (mg/kg

- bw) 0.1049 0.1049 Adjusted toxicity value (mg/kg

- bw) 3845.8028 38.4580 Ratio of exposure to toxicity 0.0000 0.0027

Conclusion* Drinking water exposure alone is NOT a potential

concern for mammals Drinking water exposure alone is NOT a potential

concern for mammals

### 69 Table 3. Avian Results

Parameter Acute Chronic Upper bound exposure (mg/kg

- bw) 0.4941 0.4941 Adjusted toxicity value (mg/kg

- bw) 3602.1476 250.5434 Ratio of exposure to acute toxicity 0.0001 0.0020

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



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

- target animals.

2. Output from the Screening Tool for Inhalation Risk (STIR)



# Input

Application and Chemical Information

Enter Chemical Name Prometryn

Enter Chemical Use All 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) 241.4 Enter Chemical Vapor Pressure (mmHg) 1.60E

- 06 Enter Application Rate (lb a.i./acre) 4

Toxicity Properties

**Bird**

Enter Lowest Bird Oral LD 50 (mg/kg bw) 4640 Enter Mineau Scaling Factor 1.15 Enter Tested Bird Weight (kg) 0.178

**Mammal**

Enter Lowest Rat Oral LD 50 (mg/kg bw) 1802

Enter Lowest Rat Inhalation LC 50 (mg/L) 4.96 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 ) 2.08E

- 02

Maximum 1

- hour Vapor Inhalation Dose (mg/kg) 2.61E

- 03

Adjusted Inhalation LD 50 7.12E+01

Ratio of Vapor Dose to Adjusted Inhalation LD 50 3.67E

- 05 Exposure not Likely

### 70 Significant

Maximum Post

- treatment Spray Inhalation Dose (mg/kg) 3.84E

- 01 Ratio of Droplet Inhalation Dose to Adjusted Inhalation
LD 50 5.40E

- 03 Exposure not Likely Significant



### Results Mammalian (0.015 kg ) Maximum Vapor Concentration in Air at Saturation (mg/m 3 ) 2.08E

- 02

Maximum 1

- hour Vapor Inhalation Dose (mg/kg) 3.28E

- 03

Adjusted Inhalation LD 50 2.95E+02

Ratio of Vapor Dose to Adjusted Inhalation LD 50 1.11E

- 05 Exposure not Likely Significant

Maximum Post

- treatment Spray Inhalation Dose (mg/kg) 4.83E

- 01 Ratio of Droplet Inhalation Dose to Adjusted Inhalation
LD 50 1.64E

- 03 Exposure not Likely Significant

### 71 

# 10.4 Appendix D: EIIS Incident Report

EIIS Pesticide Summary Report: General Information Prometryn (080805)

Incident # Date County State Certainty Legal.

Formul. Appl. Method Total Magnitude



### AQUATIC

Cotton

I004021

- 005 8/6/1996 Richland LA 1 UN

I004021

- 004 8/6/1996 RICHLAND LA 1 RU

I004668

- 011 8/7/1996 RICHLAND LA 1 RU



### PLANTS

Corn

I019130

- 056 7/31/2007 New Madrid MO 3 UN Broadcast



### COTTON

I007796

- 006 8/17/1998 HALE TX 2 UN N/R

I007796

- 005 8/25/1998 HALE TX 2 UN N/R

I009573

- 014 11/12/1999 CALDWELL TX 3 RU F Broadcast

I016903

- 008 7/21/2005 Uvalde TX 2 RU
EC Band 60 acres cotton

I016903

- 009 9/8/2005 Evans GA 2 RU
EC Band 26 acres cotton

Page 1 of 1

### 72 Incident # Species Scientific Name Magnitude Response Rt. Exposur



### AQUATIC

COTTON

I004021

- 004

carp Cyprinus carpio thousands mortality

shad Clupeidae 25 mortality

I004021

- 005

buffalo Catostomidae hundreds mortality

shad Clupeidae thousands mortality

I004668

- 011

buffalo Catostomidae hundreds mortality

gar Lepisosteus spp. hundreds mortality

shad Clupeidae hundreds mortality



### PLANTS

Corn

I019130

- 056

corn Zea mays 86 acres plant damag

COTTON

I007796

- 005

cotton Gossypium all 600 acres mortality

I007796

- 006

cotton Gossypium all 1424 acres mortality

I009573

- 014

cotton Gossypium 70% of 58 acres plant damag

I016903

- 008

cotton Gossypium 60 acres plant damag

I016903

- 009

cotton Gossypium 26 acres plant damag

Tuesday, October 09, 2012 Certainty Code: 0=Unrelated, 1=Unlikely, 2=Possible, 3=Probable, 4=Highly Probable. Legality Code: RU=Registered Use, M=Misuse, MA=Misuse (Accidental), MI=Misuse (Intentional), U=Unknown.

Page 2 of 2