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

OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION

PC Code: 109801 DP Barcode: D359480, 357471 Date: February 28,2012 

### Dee.t'ilun'. 

### ?44570 MEMORANDUM
Subject:



### To: Refined iprodione drinking water assessment for label amendments and proposed new uses on fruiting vegetables and cucurbits.
Lisa Jones, Reviewer Tamue Gibson, Reviewer Mary Waller, Risk Manager Fungicides Branch Registration Division (7505P)



### From: Donna Davis, RiskAssessor Michael Metzger, Branch Chief RiskAssessmentBranch 7 Health Effects Division (7509P)
Chuck Peck, Environmental Engineer Environmental RiskBranch IV Environmental Fate and Effects Division (7507P)

Reviewed

### b~:.a)"im Carleton, Ph.D., Senior Scientist 

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### 11'''Environmental Risk Branch N Environmental Fate and Effects Division (7507P) 

### Approved by:MariettaEcheverria, Branch Chief 

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### It. Environmental Risk Branch N Environmental Fate and Effects Division (7507P)



### EXECUTIVE SUMMARY

The Environmental Fate and Effects Division (EFED) conducted a drinking water assessment (DWA) for iprodione in response to label amendments and proposed new uses on fruiting vegetables and cucurbits. The estimated drinking water concentrations (EDWC) have 

# '1.1•••111 2086812

### been revised and replace previously reported values. The revisions and refinements in this assessment are to account for residues of concern that were not considered in the previous DWAs, and in response to comments on the previous DWA provided by the registrant (D385307+, April 5, 2011).

New uses proposed on the Enclosure label (Reg. No. 86153-3) include cucurbits applied at a single maximum applicationrate of2 lbs ai/A, with amaximum seasonal application rate of 3 lbs ai/A and a minimum retreatment interval of 12 days. For fruiting vegetables, the single maximum application rate is 3 lbs ailA, with a maximum seasonal application rate of3 lbs ailA. 

### If an application is made at less than the single maximum application rate, a minimum retreatment interval of 12 days is required. For peanuts, the single maximum application rate is 1.5 lbs ailA, with a maximum seasonal application rate of3 lbs ailA and a minimum retreatment interval of14 days. Previously, EFED calculated estimated drinking water concentrations (EDWCs) for iprodione and the iprodione degradate 3,5-dichloroaniline (3,5-DCA) (D385307+, April 5, 2011). Acute concentrations foriprodione from all ofthe modeled crops (excluding rice) were in the range of0.03 to 361 ug/L; chronic concentrations were in the range of0.0 to 3.5 ug/L; and
cancer concentrations were in the range of0.0 to 1.6 ug/L. Acute concentrations for 3,5-DCA from all ofthe modeled crops (excluding rice) were in the range of0.05 to 153 ug/L; chronic concentrations were in the range of0.03 to 56 ug/L; and cancer concentrations were in the range of0.01 to 36 ug/L. Groundwater concentrations for the highest annual use ofiprodione (24 lbs ai/A) were 25.4 and 1.1 ug/L foriprodione and 3,5-DCA, respectively. Since the previous assessment (April 2011), EFED received comments from the registrant, and had discussions with HED regarding residues ofconcern, which have changed the inputs and conclusions ofthe previous drinking water assessment. In particular, in response to comments received from the registrant, EFED has no longer included the unextracted residues in the estimation ofthe aerobic soil metabolism half-life for iprodione residues. EFED has also refined assumptions ofthe proportion ofmaximum iprodione residues relative to 3,5-DCA based
on information from metabolism studies. Specifically, EFED has assumed that 75% of the iprodione applied is converted to 3,5-DCA, with 25% ofthe applied iprodione available for runoff. Lastly, based on the findings ofthe Residues of Concern Knowledge Subcommittee (ROCKS), three new degradates, RP30228 {3-(l-methylethyl)-N-(3,5-dichlorophenyl)-2,4- dioxo-1-imidazolidine-carboxamide}, RP35606 {[(dichloro-3,5-phenyl)-1-isopropylcarbamoyl3]-2-acetic acid}, and RP32490 {3-(3,5-dichlorophenyl)-2,4-dioxo-1-imidazolidinecarboxamide}, were included as residues ofconcern related to the parent iprodione (D393960, October 5, 2011). As such, half-lives for the hydrolysis, aerobic soil, aerobic aquatic, and anaerobic aquatic metabolism studies were recalculated using a total toxic residue (TTR) approach for iprodione, RP30228, RP35606 and RP32490. Chemical and fate input parameters for 3,5-DCA did not otherwise change.
Tables 1 

### and 2 list the EDWCs for the proposed new uses and the highest existing uses for total toxic residues of iprodione and the degradate 3,5-DCA, respectively. Acute concentrations for total toxic residues ofiprodione from all ofthe modeled crops (excluding rice) are in the range of 0.01 to 92 ug/L; chronic concentrations are in the range of0.0 to 31 ug/L; 

### and

2

### cancerconcentrations are in the range of0.0 to 18 ug/L, Acute concentrations for 3,5-DCAfrom all of the modeled crops (excluding rice) are in the range of 0.04 to 115 ug/L; chronic concentrations are in the range of0.02 to 42 ug/L; and cancer concentrations are in the range of 0.01 to 27 ug/L. Groundwater concentrations for the highest annual use ofiprodione (24 lbs ai/A) are 0.29 and 0.81 ug/L for total toxic residues ofiprodione and 3,5-DCA, respectively. A complete listing ofEDWCs for all labeled uses can be found in 

### Tables 11 and 

### 15. The EDWCs for rice are unrefined Tier I estimates and are not appropriate for estimations ofchronic and
cancer risk without further refinement. Other than rice, the highest EDWCs represent modeled
use on turfat the maximum applicationrate of24 lbs 

### ail Azyear.



### Table 1. Selected estimated drinkingwater concentrations for total toxic residues of 

### dO rpro tone Drinking Use Seasonal I-in-IO I-in-IO 30-year watersource application year year average rate (Ibs ai/A) acute chronic (I!g/L) (/lglL) (/lgIL) Surface Water Fruiting vegetables (new use) 3 x I Ib ai/A 25 3.3 2.2 Surface Water Cucurbits (new use) 3 x I lbai/A 36 3.5 1.7 Surface Water Peanuts (label revision) 2 x 1.5 lb ai/A 23 5.5 2.5 Surface Water Turf 6 x 4 lb ai/A 92 31 18 Surface Water Rice lib ai/A 175 < 175 < 175 Groundwater Turf 241bai/A 0.29 0.29 0.29


### Table 2. 

### Selected estimated drinkingwater concentrations for the iprodione degradate 3,5- DCA Itinz f 

## r f" 

### di 

### resu tm2 rom appi

### ications 0 

### rpro ione Drinking Use Seasonal I-in-IO I-in-IO 30- year watersource application year year average rate (lbs ai/A) acute chronic (l!glL) (/l21L) (/l21L) Surface Water Fruiting vegetables (new use) 3 x I Ib ai/A 36 5.4 3.8 Surface Water Cucurbits (new use) 3 x I Ib ai/A 32 4.2 2.3 Surface Water Peanuts (label revision) 2 x 1.5 Ib ai/A 24 6.0 4.0 Surface Water Turf 6 x 41b ai/A II5 42 27 Surface Water Rice 1 Ib ai/A 21 I < 211 < 21 I Groundwater Turf 24 Ib ai/A 0.81 0.81 0.81



### EFED evaluated monitoring data from national studies not targeted to iprodione use areas in addition to targeted studies submitted by the registrant. The majority ofthe non-targeted monitoring samples (>98%) collected for iprodione and 3,5-DCA were belowlevels ofdetection. Maximum detected concentrations ofiprodione in surface and ground water monitoring were 45 and 5.75 ug/L, respectively 

### (Table 6). Concentrations of3,5-DCA in surface and ground water monitoring were less than (or equal to) 0.09 and 0.1 ug/L, respectively 

### (Table 6). However, variations in reporting and detection limits introduce uncertainty into these results. Additionally, as this monitoring was not targeted specifically at iprodione use areas or times of known iprodione use, the monitored concentrations are unlikely to reflect maximum iprodione concentrations that may occur in surface waters, such as when runoffevents occur shortly after application. Additionally, the three new residues ofconcern that are included in the modeling were not analyzed in any ofthe monitoring studies, so these concentrations may underestimate total iprodione residues ofconcern.

3

### Targeted surface water sampling (MRIDs 47579101 and 47881501) associated with turf applications ofiprodione conducted by Bayer Cropscience from 2006 to 2009 found maximum concentrations ofiprodione and 3,5-DCA that were less than or equal to 0.56 and 0.1 ug/L, respectively. However the iprodione application rates employed during this study were apparently four orders ofmagnitude less than the maximum allowable 24 lbs ai/A (which was used in the modeling). Additionally, the three new residues ofconcern were not included in this focused monitoring study.
PROBLEM FORMULATION


### This drinking water assessment is being conducted for iprodione total toxic residues (TTR) and its degradate, 3,5-DCA, in response to label amendments and proposed new uses on fruiting vegetables and cucurbits. The revisions and refinements in this assessment take into account to comments on the previous DWA provided by the registrant (D385307+, April 5, 2011) and residues ofconcernthat were not consideredin theprevious DWAs.


### Intheir comments, the registrant indicated that, as EPA had in the past considered 3,5- DCA the terminal degradate for iprodione and aerobic soil metabolism studies conducted using 3,5-DCA had indicated that it eventually became bound to the soil over time, unextractable residues should not be included in the estimation ofthe aerobic soil metabolism half-life for iprodione. 3,5-DCA has been detected in aerobic soil and aerobic and anaerobic aquatic metabolism studies. While the submitted degradation studies conducted on 3,5-DCA reported large amounts ofunextracted and uncharacterizedmaterial, EFED concluded, following a review of the extraction method, that under aerobic conditions 3,5-DCA either binds to soil or is transformed to other unextracted residues that are not available to off-site transport (D357470+, 12/30/2009; D386316+, 2/16/2011). Based on this information, EFED has agreed with the registrant's comment and has removed the unextractable residues from the iprodione TTR aerobic soilmetabolismhalf-life estimate.


### In the previous assessment, EFED conservatively assumed 100% ofthe iprodione was converted to 3,5-DCA. However, ifthis were the case, then EDWCs should only be developed for 3,5-DCA, as no iprodione would remain. 

### In the current refinement, EFED has used the findings from the aerobic soil metabolism study (MRID 43091002) which indicated up to 75% of unextractable residues were formed in the study. Based on 3,5-DCA's ability to bind to soil, EFED assumed that the 75% ofunextractable residue from the aerobic soil metabolism study is 3,5-DCA. As such, the EDWCs generated in this assessment assume that 75% ofthe applied iprodione is converted to 3,5-DCA and the remaining 25% ofapplied remains as iprodione TTR on the field, available for transport in runoff. Actual conversion percentages lie between the extremes of 0 and 100% conversion of iprodione to 3,5-DCA. EFED believes that the assumption of 75% conversion is a realistic refinement based on the limited aerobic soil metabolism data.
On September 14, 2011, the Health Effects Division (HED) Residues of Concern Knowledge Subcomittee (ROCKS) reconvened on iprodione to reconsider metabolites and degradates that were being included in the risk assessment and tolerance expressionfor iprodione

4

### in plant and livestock commodities, but not in the drinking water assessment. Based on that results ofthat meeting, the following degradates were found to be oftoxicological concern: 3,5- DCA (RP32596), RP30228, RP35606, and RP 32490. 3,5-DCA is considered to have a genotoxic mode of tumor induction based on its similarity to its structural analog parachloroaniline, which is carcinogenic in animal carcinogenicity studies (USEPA, 1998). HED's ROCKS identified the remaining degradates as residues of concern (1) due to their presence as major degradates in the hydrolysis, aerobic aquatic, and anaerobic aquatic metabolism studies and (2) their structural similarities to the parent, indicating similartoxicity to the parent. HED's ROCKS concluded that "By including these precursor degradates in the risk assessment with parent iprodione and conducting a separate assessment for 3,5-DCA, the overall approach should be sufficiently conservative and protective ofthe assessed risks including those for cancer" (D393960, October5,2011).

This drinking water assessment uses modeling to provide estimates ofsurface water and groundwater concentrations for iprodione total toxic residues (TTR) and 3,5-DCA in source water for drinking water (pre-treatment) resulting from iprodione labeled uses. Routes of transport to source water are primarily from runoff, leaching, and spray drift. The coupled models PRZM and EXAMS were used to assess exposure in surface water due to runoffand drift from the proposed and existing iprodione uses. Exposure concentrations in groundwater due to leaching were assessed with the screening model SCI-GROW. Exposure concentrations resulting from applications to rice were assessed with the unrefined TierI RiceModel.

In addition to modeling estimates, this drinking water assessment considers monitoring data from available sources. This includes data from non-targeted data, including the US Geological Survey's National Ambient Water Quality Assessment (NAWQA) database, the California Department ofPesticide Regulation's surface water database, and the Suffolk County, New York groundwater monitoring program, and data from a 3-year monitoring study to ascertain the levels ofiprodione and 3,5-DCA in raw and finished drinking waterin areas ofhigh turfuse (MRIDs 47579101 and 47881501).



### ANALYSIS

Use 

### Characterization Iprodione [3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide] is a contact and/or locally systemic fungicide. Application methods include aircraft aerial applications, groundsprays, chemigation, and dipping. It 

### is registered for use on a variety of fruits, vegetables, turfand ornamentals. The registrant is proposing to add new uses on fruiting vegetables andcucurbits, as well as modifications to the uses on peanuts. The current formulations are for outdooruse only.

EFED reviewed all relevant labels for the pertinent information on uses. EFED conducted model simulations for most ofthe labeled uses (in some cases multiple scenarios for a given use) in order to derive EDWCs. Some ofthe uses could not be directly simulatedbut were addressed using surrogate scenarios (e.g., California almond used for pistachio and Florida cabbage for Florida Chinese Mustard). The simulations that were performed were sufficiently broad to provide arealistic assessment ofthe varied uses ofiprodione.

5

### EnvironmentalFate andTransport Characterization Iprodione is moderately mobile (FAO soil mobility classification) in soil systems with a 

### Koc around 500 ml/g. It 

### is not volatile and, as such, is not subject to long-range aerial transport. Iprodione is most persistent in acidic environments, with half-lives around 130 days at pH 5 in aquatic systems; however, in neutral aquatic systems, the half-life is only 4.7 days (pH 7), and in alkaline systems, iprodione quickly degrades (27 minutes at pH 9). In aquatic systems, iprodione degradation occurs primarily via hydrolysis. In an aquatic photolysis study, iprodione degraded slowly with a half-life of67 days in a pH 5 buffered solution, with no major degradates**(~10%** 

### ofthe applied) observed.

Submitted iprodione soil degradation studies show high levels of unextracted and unidentifiedresidues. This leads to uncertainty in characterizationofthe chemical's degradation. In an aerobic soil degradation study (MRID 43091002), 75-87% ofthe residues at day 276 were unextracted and uncharacterized. Unextractable residues exceeded 10% ofapplied between days 14 and 30 ofthe study. Thus the extent to which these residues constitute parent iprodione or degradates ofconcern remains unknown. However, based on 3,5-DCA's affinity to bind to soil or be transformedto other unextracted residues that are not available to off-site transport, and the that 3,5-DCA is considered the terminal degradate in iprodione metabolism studies, EFED assumed that the unextracted and uncharacterizedresidues in the iprodione soil studies were 3,5- DCA and used this information to estimate an upper bound conversion rate of75% ofiprodione to 3,5-DCA. In terrestrial and aquatic field dissipation studies, iprodione dissipated with DT50s of3 to 7 days, at pH values (6.2-8) which suggest that hydrolysis may have been a contributing factor. Howeverbecause ofthe extraction concerns raised in the soil studies, the extent to which these DT50 values represent decay rather than temporary sequestering ofiprodione (or degradates ofconcern) is not known. A summary ofmajor degradates observed in laboratory and field studies, their structures, and proposed degradation pathways is provided in Appendix 1. Appendix 1 

### also lists the degradates by study type, and the maximum percent ofapplied at which each ofthe degradates was detected. HED has identified degradates 3,5-DCA (RP32596), RP30228, RP35606, and RP32490 as residues ofconcern (D393960, October 5, 2011). Based on recommendations from the ROCKS, iprodione, RP30228, RP35606, and RP32490 are therefore evaluated by EFED as total toxic residue (TTR), separate from the evaluation of 3,5-DCA. Thus this assessment considers the exposure to both iprodione TTR and 3,5-DCA. When the three degradates are included, the half-lives of the TTR increase dramatically beyond that of the parent. The hydrolysis half-lives are 772 days at pH 5, 266 days at pH 7, and 56 days at pH 9. The aerobic aquatic half-life becomes 60.7 days, and the anaerobic half-life becomes 92 days. The aerobic soil metabolism half-life ofTTR remains almost the same as that ofthe parent chemical, at 19.2 days. However this result is based on a single aerobic soil metabolism study, and the half-life does not take into account the high levels ofunextracted residues, which are assumed to consist entirely of3,5-DCA.

Table 

### 3 summarizes the general fate properties of iprodione parent and total toxic residues (TTR) based on submitted studies, and Table 4 

### presents the properties of 3,5-DCA. Summaries ofthe available information arepresented in the following sections.

6

### Table3. Summary ofgeneral fate properties ofiprodione and total toxic residues of
concern Property Value SourcelMRID Comments Molecularformula C13HI3ChN30 3 Formulareported for iprodione Molecular weight (g/mole) 330.2 Value reported for iprodione Vapor pressure (Torr, 20°C) 2.7xlO-7 Iprodione Value reported for iprodione RED Henry's Law Constant 9.0xlO·9 calculated =(vp/760)/(MW/sol); vp in (atm m3/mol) Torr; sol in mg/L; MW in g/mol Octanol/WaterCoefficient 3.1 47778802 Value reported for iprodione (Log Kow nOC) Solubility in water (mg/L, 20°e) 13 47778802 pH Parent TTR Study conducted for 30 days Hydrolysis half- life (days) 5 131 772 41885401 (pH 5), 125 hours (pH 7), and 7 4.7 266 121 minutes (pH 9). 9 0.02 56 Aqueous photolysis half- life 64 (parent and TTR) 41861901 (days) Parent TTR High amounts of unextracted Aerobic soil half-life (days) 43091002 1 material (75-87%). These 16 19.2 residues are assumed to be 3,5- DCA. Aerobic aquatic half-life (days) Parent TTR 419276011 pH = 8.5 9 60.7 42503801 Anaerobic aquatic half-life (days) Parent TTR 41755801 11 92 223(sandy loam) Values reported for iprodione Organic carbon partitioning 432 (loamy sand) 43349202 coefficient (Koc) (mUgoc) 507 (loam) 543 (clay)
Terrestrial field dissipation DT50 Parent TTR CA - silt loam CA 7 28 41877401 (days) NC <3 <3 NC - loamy sand
Water Values reported for iprodione

3.7 days (TX) Aquatic field dissipation DT50 2.9 days (MS) 43718301 Sediment

3.4 months (TX) 4.1 months (MS) 1. A second aerobic soil metabolism study (MRID 44590501) was conducted III 1993. Howeverthe study was classified as supplemental because nonextractable

# e 4C]residues and volatiles were not measured, so a material balance could not be determined.
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## , - Property Value SourcelMRID Comments Molecular wt 162 Product chemistry data Solubility (mg/L) 784 EPI Suite Vapor pressure 8.5xlO-3 EPI Suite (Torr, 25°e) Henry's Law Constant 10-b EPI Suite (atm m3/mol) Aerobic soil half-life 50.2 (sandy loam) 43091002 High levels of unextracted

7Property Value SourcefMRID Comments (days) 7.9 (silt loam) 45239201 residues (see text). Half- 

### ! 17.6 (sandy loam) lives do not include 

## I 49 (silt loam) 48219201 (8.3 mg/kg applied) unextractedresidues 107 (sand) based on extensive 40 (silt loam) 48219201 (1.47 mg/kg applied) extractiontechniques. 59 (sand) Organic carbon 380 (silt foam) 45114101 partitioning coefficient 593 (sandy loam) (Koc) (mL/goc) 626 (loamy sand) 788 (pond sediment, sand) 932 (clay)



### Terrestrial Field Dissipation 

### Two terrestrial field dissipation studies are available (both described in MRID 41877401). Neither study monitored for the degradate 3,5-DCA, but did monitor for the degradates RP30228 and RP32490. The two studies were conducted in California and North Carolina and are summarizedbelow. In the San Juan Bautista, CA study, iprodione was applied 8 times to carrots at 1 lb ailA/application. Iprodione dissipated with an observed DT50 

### of7 days in the 0-15 cm soil layer ofa silt loam soil (pH 7.9-8.0). The degradates RP30228 and RP32490 were detected at 0-15 and 15-30 cm soil depths. Iprodione and its degradates were not detected below the 30 em depth. RP30228 was a maximum average of0.47 ppm at 28 days after treatment, declining only to 0.15 ppm at 538 days. RP32490 was observed at relatively low concentrations (SO.09 ppm) in the field. The observed DTso

### for iprodione and its degradates was 28 days in the top 15 em. In the NC study, iprodione was applied 8 times to carrots at 1 lb ailA/application. The observed DTso

### was <3 days at 0-15 em (loamy sand soil, pH 6.2 - 6.8). RP30228 and RP32490 were detected only at the 0-15 em depth. No residues were detected below 15 ern. 

### The concentrations ofRP30228 were lower than those observed in CA, ranging from 0.01 to 0.08 ppm until 492 days. The observed DTso 

### for iprodione and its degradates was also <3 days. Aquatic Field Dissipation 

### In aquatic field dissipation studies (MRID 43718301), iprodione was applied twice to flooded rice paddies at 0.5 lblacre at 15-day intervals at two sites (TX and MS). Iprodione was applied to the rice foliage at both sites (55% canopy coverage at TX, 85% at MS). The two sites were flooded for 1 month. Flood water dissipation half-lives for iprodione were 3.7 days in TX and 2.9 days in MS; soil half-lives were 4.1 and 3.4 months in MS and TX, respectively. Maximum concentrations observed in paddy water in both studies were around 500 ug/L, 

### Storage sample recoveries for 3,5-DCA were only 18%; thus, this study is not suitable for characterizing the formation or persistence of3,5-DCA. The major degradates observed at both sites were RP30228 and RP37176. Water and soil dissipation half-lives for the TTR were not significantly different from those ofthe parent only.

8

### Volatilization/Long-Range Transport 

### Iprodione is not volatile, as indicated by the calculated Henry's Law constant of2.7 x 10-
9 

### atmm3/mol, 

### so long-range transport is not expected to occur. The Agency has not received any direct measurements ofvolatility for 3,5-DCA, RP30228, RP35606, or RP32490. In the absence of such data, the Agency used EPISuite to estimate Henry's Law constants for these chemicals. For 3,5-DCA, the estimated Henry's Law constant is much higher than that ofparent iprodione (around 10- 6 

### atm-mvrnol), while for the other degradates estimated Henry's Law constants are much lower than for the parent (less than 10-12 atrn-rrr'zmol), 

### Although 3,5-DCA is expected to be more volatile than the parent or the other degradates based on estimated data, it was not detected in the volatile traps in the submitted laboratory studies.
Fate Properties ofDegradates 3,5-DCA 

### Results ofbatch sorption tests (MRID 45114101) on five soils are summarized in Table 

### 4. Isotherms of3,5-DCA for these five soils are nonlinear, with Freundlich exponents around 0.7. This means that sorption affinity decreases as concentrations increase, and that 3,5-DCA will become less mobile as concentrations decrease. Based on the FAO soil mobility classification scheme used by EFED, this chemical is classified as moderately mobile, with an average Kocof664 mIl

### goc. An aerobic soil metabolism study of 3,5-DCA on two different soils showed little evidence that 3,5-DCA appreciably degraded over a 9-month period at 25°C (MRID 45239201). Apparent dissipation was caused by a high level ofunextracted residues. Unextracted residues accounted for 66% and 81% ofthe applied in the two systems. The only residues that were distinguishable from the applied 3,5-DCA amounted to only 4 to 5% ofthe applied 14C.

In order to address the issue ofunextracted residues, Bayer Cropscience conducted a second study that was submitted in 2010 which used more aggressive analytical methods to extract 3,5-DCA from the soil (MRID 48219201). Based on nonlinear regression analysis, estimated half-lives ranged from 40 to 107 days in silt loam and sand soils. Unextractable residues were still high, and averaged 54.4-67.8% ofthe applied at 119 days posttreatment; however, based on an EPA review of the analytical method, in which Bayer Cropscience employed sufficiently exhaustive methods to extract 3,5-DCA, it was determined that the 3,5- DCA residues were bound to the soil and assumed unavailable for off-site transport.
RP30228, RP35606, and RP32490 

### The degradates RP30228, RP35606, and RP32490 have been newly identified as residues of concern and as such registrant-submitted fate data are not available. Using the structural analysis tools in EPISuite, physical-chemical properties and fate parameters were estimated for the three degradates (Table 

### 5). The degradates appear to be similar in solubility and octanollwater 

### partition coefficients as parent iprodione, but more mobile, based on their estimated Kocvalues.

9

### EPIS it d 

### t f D 

### dO MOl 

### P F able 

### 50 Estimated ate roperties 

### or ajor II

### rro ione egra 

### a es rom me

Property RP30228 RP32490 RP35606 Molecularformula C13H13ClzN303 CloH7C12N303 C13HlsC12N304 Molecularweight (g/mole) 330.2 288 348 Vaporpressure (Torr, 25°C) 1.12x1O. 11 6.4x1O'11 3.7x1O'lL Henry's Law Constant 3.5x1O'13 3.0x1O'14 2.2xlO·13 (atm m3/mol) OctanoliWaterCoefficient 3.24 1.48 3.41 (Log Kow) Solubility in water (mg/L, 25°C) 13.9 792 7.8 Organic carbon partitioning coefficient (Koc)(mL/goc)1 53 - 424 16 - 47 21

- 90

.. 

### T

1. Values representrange Koc estimates denvedusmg the Molecular Connectivity Index (MCI) method and the log Kowmethod, both available inEPISuite.



### Monitoring A detailed discussion ofthe monitoring results for iprodione and 3,5-DCA is provided in the previous drinking water assessment (D385307+, April 5, 2011). A summary ofthe results is provided in Table 6. While the concentrations, for the most part, are lower than 1 ug/L for iprodione and 3,5-DCA, there is uncertainty in these numbers because the detection limits were as high as 5 giL 

### for iprodione and 10 giL 

### for 3,5-DCA. No monitoring data specifically for RP30228, RP35606, or RP32490 were available.
d35 DCA 

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## , 

## - Concentration Frequency Limit of Location Range Detection Date Source (lt2!L) ofDetects (lt2/L) Iprodione, SurfaceWater National 0.01-45.3 120/4,715 0.01-1.9 2000-2010 NAWQA CA



### -- 0/11 NA 2004/2005 CDPR Rahway, NJ 0.051 - 0.564 34/498 0.05 2006 -2009 MRID 47881501 Bradenton, FL



## -- 0/165 0.05 2006 -2009 MRID 47881501 Aurora, IL



### -- 0/169 0.05 2006 -2009 MRID 47881501 Iprodione, Groundwater National 0.016 1/3029 0.01-1.4 2000-2010 NAWQA Suffolk County 5.75 1 1 12,379* 0.2 - 5 1998 - 2010 Suffolk County 3,5-DCA, SurfaceWater National 0.002 - 0.09 77 14,139 0.003 - 0.05 2000 -2010 NAWQA Rahway, NJ 0.027 1/498 0.05 2006

- 2009 MRID 47881501 Bradenton, FL



### -- 0/165 0.05 2006 - 2009 MRID 47881501 Aurora, IL



## -- 0/169 0.05 2006 - 2009 MRID 47881501 3,5-DCA, Groundwater National 0.001 - 0.1 27/2,772 0.003-0.013 2000-2010 NAWQA Suffolk County



## -- 0/1583* 0.3 - 10 1998 - 2010 Suffolk County NA - not available * 56 of the iprodione samples and 11 ofthe 3,5-DCA samples had reporting limits greater than 1 ug/L. Suffolk County indicatedthat the single detection was actually from an irrigation well which does not serve as a drinking water source and should not have been captured in the database ofgroundwater drinking water sources.



### 10

### Drinking WaterExposureModeling 

### EDWCs were generated using EFED's standard suite ofmodels. The Pesticide Root Zone Model (PRZM, v3.12.2, May 2005) and Exposure Analysis Modeling System (EXAMS, v2.98.4.6, April 2005) are simulation models coupled with the input shell PE5.pl (v.5, Nov. 15, 2006) to generate EDWCs ofiprodione TTR and 3,5-DCA residues that may occur in surface water used as drinking water. The PRZM model simulates runofffrom and transformation of pesticide within a standard watershed consisting of a 172.8 ha field of treated crops. The EXAMS model simulates associated aquatic concentrations (from runoff, erosion, and spray drift ofpesticide) within an adjacent standard drinking water "index" reservoir of5.26 ha surface area, and average depth 2.74 m. A more detailed description ofthe index reservoir and its watershed can be found in Jones et al., 1998. The coupled PRZM and EXAMS models and users manuals may be downloaded from the U.S. Environmental Protection Agency (EPA) Water Models web-page (http://www.epa.gov/oppefedl/models/water/). 

### Percent Cropped Area (PCA) adjustment factors that account for the maximum area within a watershed that may be planted with the modeled crop are applied to concentrations predicted by 

### PRZM/EXAMS. Screening Concentration in Ground Water (SCI-GROW v2.3, Jul. 29, 2003) is a regression model used as a screening tool to estimate pesticide concentrations found in ground water used as drinking water. SCI-GROW was developed by fitting a linear model to ground water concentrations with the Relative Index ofLeaching Potential (RILP) as the independent variable. Ground water concentrations were taken from 90-day average high concentrations from Prospective Ground Water studies. The RILP is a function ofaerobic soil metabolism and the soil-water partition coefficient. The output ofSCI-GROW represents the concentrations of iprodione TTR and 3,5-DCA residue that might be expected in shallow unconfined aquifers under sandy soils, which is representative ofthe ground water most vulnerable to pesticide contamination and likely to serve as a drinking water source. The SCI-GROW model and user's manual may also be downloaded from the EPA Water Models web-page (USEPA, 2006). The EFED Tier 1 Rice Model (v1.0, May 8, 2007b) was used to estimate aquatic exposures for direct water use with conservative, maximum values that represent high exposure sites for rice use. Each ofthese sites represents a water body holding a 10 em water depth. When a pesticide is applied to a water body, the model assumes that it will instantaneously partition between a water phase and a sediment phase based on the partition coefficient ofthe chemical. The formula ofthe Tier I Rice Model vl.O is as follows:

11

# c - mat'

w
- 

### 0.00105 

## +0.00013K d


### and, ifappropriate:

where: Cw = 

### water concentration [ug/L] 

### m.,' = 

### mass appliedperunit area [kg/ha] K, = 

### water-sedimentpartitioning coefficient [Llkg] Koc = 

### organic carbonpartitioning coefficient [Llkg]
Drinking water concentrations were determined for iprodione TTR and degradate 3,5- DCA. Calculation ofiprodione TTR concentrations is described in the first section below, and calculation of3,5-DCA concentrations are described in a subsequent section. Drinking WaterEstimates for ParentIprodione


### MethodsforDeterminingParent(Iprodione) Concentrations Iprodione TTR EDWCs were determinedfor the iprodione uses listed in Table 7. For the rice use, surface water concentrations were determined using the Tier I Rice Model. For groundwater concentrations, SCIGROW 2.3 was used. Input parameters for PRZMlEXAMS iprodione TTR are given in Tables 7 and 8. Input parameters for the Tier I Rice Model are given in Table 9. Input parameters for SCIGROW are given in Table 10. Parameter selections were determined according to EFED guidance (USEPA, 2009) unless otherwise specified. As applications to turf are permitted under the current labels, no percent cropped area adjustment factors were applied to the results, per current EFED guidance (USEPA, 2010). Although EPISuite estimates for the iprodione degradates indicate they are more mobile than the parent, the Koc 

### for iprodione was used in the TTR modeling as it is based on study data and not model predictions.

In the previous assessment (D385307+, April 5, 2011), EFED conservatively assumed 100% ofthe iprodione was converted to 3,5-DCA. In the current refinement, EFED has used the findings from the aerobic soil metabolism study (MRID 43091002) to estimate that 75% of applied iprodione is converted to 3,5-DCA, and the remaining 25% of applied remains as iprodione TTR on the field, available for transport in runoff. Actual conversion percentages must lie between the extremes of 0 and 100% conversion of iprodione to 3,5-DCA. EFED believes that the assumption of75% conversion is a realistic refinement based on the limited aerobic soil metabolism data. After modeling iprodione using the application rates shown in Table 7, the results were postprocessedby applying a scaling factor of0.25.

For the 

### PRZM/EXAMS simulations, application dates that are given in Table 7 are the ones that were chosen with consideration for the label recommendations for application timing

12

### and pre-harvest interval, along with the crop dates associated with each PRZM scenario file. The application dates used in these simulations were selected from the approximate middle ofthe possible window ofapplications; however, the selection ofthe date is not a precise process, and there may be some variability about the date selection. Application dates for currently labeled uses are the same as those used inEFED's previous drinking water assessment (USEPA, 2007a).

d 

## r f 

### TTR d' t 

### £ d 

### T hi 7 U



### a e , 

### se-speci IC

### scenarios an usage mpu 

### s or 

### ipro tone sur ace water mo 

### e 109 Iprodione
Use Application EFED Scenario Application Number of Date ofApplication method Rate applications (interval) [lb, a.i.lA I] almond/pistachio ground CA Almond 0.52 4 Feb7, 14,28, Mar7 spray almond/pistachio aerial spray CA Almond 0.52 4 Feb7, 14,28, Mar7 bean aerial spray MI Beans 1.53 2 Jun 1,6 bean aerial spray OR Beans 1.53 2 May 5,10
berries ground OR Berries 1 4 May 20, Jun 3, 17, spray lull broccoli ground CA Cole crop 1.5 2 Jan 15, 18 4 spray
carrot aerial spray FL Carrot 1 4 Sep 25, Oct 6, 27, Nov 27

carrot aerial spray FL Carrot I 4 Nov 20,27, Dec 3,10 Oct 9, 16,23,30, carrot aerial spray FL Carrot 0.5 10 Nov 6, 13,20,27, Dec 4,11 chinese mustard ground FL cabbage 0.5 4 Nov 20,30, Dec 10, spray 20 cotton in furrow CA Cotton 0.27 1 MayS
cotton in furrow MS Cotton 0.27 1 May 1
cotton in furrow NC Cotton 0.27 1 Jun 1
cucurbits' ground FL cucumber 29 2 Oct 6, 23 incorporate
cucurbits" ground FL cucumber 1 3 Oct 6, 23, Nov 4 incorporate cucurbits" ground CAmelon 29 2 May 6, 23 incorporate
cucurbits ground CA melon 1 3 May 6, 23, Jun 4 incorporate fruiting ground CA tomato 3 1 Feb 19 vegetables" incorporate

fruiting ground CA tomato 29 2 Feb 19, Mar 8 vegetables" incorporate

fruiting ground CA tomato 1 3 Feb 19,Mar8,20 vezetables" incorporate

fruiting ground FL peppers 3 1 Augn vegetables" incorporate

fruiting ground FL peppers 29 2 Augn, Sep 8 vegetables" incorporate

fruiting ground FL peppers 1 3 Aug 22, Sep 8, 20 vegetables" incorporate



### 13Iprodione
Use Application EFED Scenario Application Number of Date ofApplication method Rate applications (interval) rib. a.i.lA1J fruiting ground FL tomato 3 1 Jan 22 vegetables" incorporate

fruiting ground FL tomato 29 2 Jan 22, Feb 8 vegetables" incorporate

fruiting ground FLtomato 1 3 Jan 22, Feb 8, 20 vegetables" incorporate

fruiting ground PA tomato 3 1 Apr 6 vegetables" incorporate

fruiting ground PA tomato 29 2 Apr 6, 23 vegetables" incorporate

fruiting ground PA tomato 1 3 Apr 6, 23, May 5 vegetables" incorporate garlic in furrow CA garlic 2 1 Sep 17 g!apes ground NY Grapes 1 4 Jun 20, 30, JulIO, spray 20
grapes ground CA Grapes 1 4 May 1,11,21,31 spray aerial lettuce /ground CA lettuce 1 3 Feb 20, Mar 2, 12 spray lettuce ground CA lettuce 1 3 Feb 20, Mar 2, 12 spray onion aerial spray GAonion 0.75 5 Mar 1, 11, 21, 31, Apr 10 onion aerial spray CA onion 0.75 5 Jan 10,20,30, Feb 9,19 Mar 1, 8,15,22,29, onion aerial spray GA onion 0.5 10 Apr 5, 12, 19,26, May 3 Feb 18,25, Mar 4, onion aerial spray CA onion 0.5 10 11, 18,25, Apr 1, 8, 15,22 ornamentals ground CA 1.25 4 Jull, 8,15,22 spray Impervious/residential peanut in furrow NC peanut 1.5 2 May 2, Jun 1 peanut ground NC peanut 1.5 2 May 7, Jun 1 spray peanut ground NC peanut 1.5 2 May 17, Jun 1 spray peanut ground NC peanut 1.5 2 Jun 1,15 spray potato aerial spray Me Potatoes 1 4 Jull, 8, 15,22

rice Not Tier 1 Rice Model 0.5 2 Not applicable applicable stone fruits aerial GA Peaches 1 28 Mar 1,8,15,22 stone fruits aerial MI Cherries 1 28 Apr 25 Mayl,8,15 strawberry aerial spray FL Strawberry 0.5 10 May 1,8,15,22, Jun 11,18, 25,Jul 2,22,29 strawberry aerial spray FL Strawberry 1.0 1 10 May 1



### 14Iprodione
Use Application EFED Scenario Application Number of Date ofApplication method Rate applications (interval) fib. a.i.lAIl turf(golfcourses, ground Jull, 15,29, Aug sod farms, PA turf 4 6 ornamental turf) spray 12,26, Sep 9 turf(golfcourses, ground Jull, 15,29, Aug sod farms, FL Turf 4 6 ornamental turf) spray 12,26, Sep 9 turf(golfcourses, ground sod farms, PA turf 1.25 4 Jull, 8,15,22 ornamental turf) spray turf(golfcourses, ground sod farms, FL Turf 1.25 4 Jull, 8,15,22 ornamentalturf) spray 1. Application rates were multiplied by 1.12 to convert to kg aifha for use m modelmg. 2. Previous assessmentused 1.0 lbs ai./A. Current labels reflect 0.5 lbs ai/A. 3. Previous assessment used l Ib ai/A. Current label (Reg. no. 264-689,2/27/2009) reflects 1.5 lbs ai/A. 4. First application at 2-4 leafstage, assumed to occur 2 weeks after emergence. No retreatment interval specified; assumed 3 days. 5. First application incorporatedto a depth of3 inches. Subsequent applications occur via drip irrigation at surface. Max annual application = 3 lbs aifyr. 6. First application incorporatedto a depth of3 inches. Subsequent applications occur via drip irrigation at surface. Max annual application = 3 lbs ai/yr. 7. First application can be aerial, but subsequent applications are restrictedto ground applications by label. 8. Previous assessment used 4 applications/yr. Current labels reflect 2 applications/yr. 9. First application at 2 lbs aifA, second application at 1 Ib ai/A. 10. Previous assessment used 4 applications/yr. Current labels reflect 1 application/yr.


### TTR 

### dO T bl 8 PRZM / EXAMS
°



### a e ° 

### InputparaEneters orrpro ione
PARAMETER(units) VALUE SOURCE COMMENT Application Rate (kg see Table 7 Label See Table 7 a.i./ha)
Number ofApplications see Table 7 Label
Interval between see Table 7 Label Applications
Molecular weight 330.2 g/mol Iprodione RED, 1998

- Henry's Law Constant 2.7 x 1O-9atm-m3/mol Iprodione RED, 1998 calculated value Vapor Pressure 2.7 x 10- 7 Torr Iprodione RED, 1998

- Solubility in Water @ 13 mg/L Iprodione RED, 1998 - 20°C, pH 8 Soil Partition Coefficient 426 ml/goc MRID: 43349202 Mean of4 soils for iprodione Koc CAM (Chemical 2 Application Method)



### 15PARAMETER (units) VALUE SOURCE COMMENT Depth ofIncorporation 4cm Iprodione label. A default of4 em was used, unless label specified differently Application efficiency Ground spray: 0.99 Input Guidance. Aerial spray: 0.95 Spray drift fraction Ground spray: 0.064 Input Guidance. Aerial spray: 0.16 Application date various Labels See Table 6 (day/month) Hydrolysis Half-life (days) 772 (pH 5) MRID: 41885401 266 (pH 7) 56 (pH 9)
Anaerobic Aquatic 276 MRID: 43091002; 3 x anaerobic aquatic Metabolism Half-life 44590501 metabolismhalf-life (days)
Aerobic Soil Metabolism 57.5 MRIDs: 43091002 3 x aerobic soil metabolism Half-life (days) half-life Aqueous Photolysis Half- 64 MRID: 41861901 life (days) @ pH 7
Aerobic Aquatic 182 MRID: 41927601; 3 x aerobic aquatic metabolism MetabolismHalf-life 42503801 half-life (days)



### TTR 

### d" t 

### dl" T bl 9 Ri



### a e 

### ce mo e input

### parame ers orrpro tone Input Parameter Value Source Comment Annual ApplicationRate 1.0 Ib a.i./A Label Two applications (@ 0.5 Ib ai/A) allowed on label at 14-day intervals by aerial spray Soil Organic Carbon 426 mL/goc MRID: 43349202 Mean of4 soils for iprodione Partitioning Coefficient (Koc)



### TTR 

### d" I t 

### t T bl 10 SCI GROW ( 23) "



### a e " 

# - v " mpu 

### parame er va ues or I)JrO 

### ione Input Parameter Value Source Comment Maximum Yearly Application 24 Label. 6 x 4 lbs ailA for turf Rate (lb a.i./A) 3 3 x 1 lbs ailA for fruiting vegetables, cucurbits Organic Carbon Partition 469 ml/goc MRID: Median Koc for iprodione Coefficient(Koc) 43349202 Aerobic Soil Metabolism Half- 19.2 days MRID: Half-life estimated from single study life 43091002



### Results: Surface Water Concentrations of 

### Iprodione TTR 

### Output from the surface water modeling of iprodione total toxic residues using PRZM/EXAMS and accounting for the 75% instantaneous conversion ofapplied iprodione to 3,5-DCA is given in Table 11. 

### The highestconcentrations (excluding rice use) are from theturf

16use (PA turfscenario), and this is due to a large extent to the high label application rate for turf (24 lb 

### ail A/yr). The Pennsylvania turfuse results in EDWCs of92 ug/l, for acute, 31 IlgIL for chronic, and 

### 18 ug/L for cancer. These values represent the one-in-ten-yearpeak concentration, the one-in-ten-year annual mean concentration, and the 30-year mean concentration, respectively. Acute concentrations from all ofthe modeled crops (excluding rice) fall in the range of0.0063 to 92 ug/L; chronic concentrations are in the range of0.0025 to 31 ug/L; and
cancer concentrations are in the range of0.00075 to 18 ug/L. Modeling scenarios that result in particularly high peak surface water concentrations include Pennsylvania turf, Florida turf, Florida carrots, Florida cucumbers, California cole crops, Floridapeppers, Georgia onions, North Carolinapeanuts, and Florida strawberries.

Foriprodione use on rice, the Tier I Rice Model gives a concentration (acute and chronic) of

### 175 ug/L, which is the highest surface water concentration associated with any use (see 

### Table 11). The Tier 

### I Rice Model estimates concentrations from an assumed equilibration ofthe pesticide with hypothetical quantities ofwater and sediment, and without any degradation ofthe pesticide. This model is intended to serve only as a screen, and ifconcerns are raised by the output ofthis model, further refinements should be considered. Maximum concentrations of iprodione measured in two aquatic field dissipation studies conducted on rice in MS and TX
were approximately 500 ug/L, where measurements were taken within the paddy. Concentrations in downstream receiving water would be expected to be lower than 500 ug/L, due to dilution.


### Table 11. Iprodione TTR TierII EDWCs for surfacewater, assuming 75% conversion to 3,5-DCA Application I-in-IO I-in-IO 30- year Use Application EFED Scenario Rate Number of year year average method [lb. a.i.lA] applications acute chronic (1Lg!L) (Jlg/L) (Jl2!L) almond! ground spray CAAlmond 0.5 4 5.5 1.7 0.93 pistachio almond/ aerial spray CAAlmond 0.5 4 7.3 2.3 1.5 pistachio

bean aerial spray MI Beans 1.5 2 16 5.5 4 bean aerial spray OR Beans 1.5 2 13 3 2 berries ground spray OR Berries I o 4 4.5 1.95 1.45 broccoli ground spray CA Cole crop 1.5 2 29 9.25 5.75

carrot aerial spray FL Carrot 1 4 40 6 4
carrot aerial spray FL Carrot 0.5 10 46 7.5 4.25 chinese ground spray FL cabbage 0.5 4 12 2.13 1.28 mustard cotton in furrow CA Cotton 0.27 1 0.0063 0.0025 0.00075
cotton in furrow MS Cotton 0.27 I 0.48 0.078 0.035
cotton in furrow NC Cotton 0.27 I 0.35 0.073 0.Q38
cucurbits ground FL cucumber 2 2 22 2.8 1.6 incorporate cucurbits ground FL cucumber 1 3 36 3.5 1.7 incorporate

17Application I-in-lO I-in-IO 30- year Use Application EFED Scenario Rate Number of year year average method [lb. a.i.lA] applications acute chronic (f.1glL) (/.lglL) (/.lglL) cucurbits ground CAmelon 2 2 0.8 0.21 0.073 incorporate cucurbits ground CAmelon 1 3 0.73 0.1875 0.0675 incorporate fruiting ground CA tomato 3 1 3.8 1.4 0.5 vegetables incorporate

fruiting ground CA tomato 2 2 5.3 1.9 0.6 vegetables incorporate

fruiting ground CA tomato 1 3 3.8 1.4 0.63 vegetables incorporate

fruiting ground FL peppers 3 1 13 1.6 0.73 vegetables incorporate

fruiting ground FL peppers 2 2 17 2.1 1.4 vegetables incorporate

fruiting ground FL peppers 1 3 25 3.3 2.2 vegetables incorporate

fruiting ground FL tomato 3 1 6 0.85 0.43 vegetables incorporate

fruiting ground FL tomato 2 2 11 1.6 0.78 vegetables incorporate

fruiting ground FL tomato 1 3 15 2.2 1.2 vegetables incorporate

fruiting ground PA tomato 3 1 3.0 0.80 0.45 vegetables incorporate

fruiting ground PA tomato 2 2 4.8 1.3 0.78 vegetables incorporate

fruiting ground PA tomato 1 3 8.8 2.3 1.3 vegetables incorporate

garlic in furrow CA garlic 2 I 0.45 0.13 0.05 grapes ground spray NY Grapes 1 4 18 7.8 5.3 grapes ground spray CA Grapes 1 4 3.5 1.8 1.5 aerial lettuce /ground CA lettuce 1 3 21 7.3 4.0 spray lettuce ground spray CA lettuce 1 3 20 7.0 3.8 onion aerial spray GA onion 0.75 5 18 4.0 2.5 onion aerial spray CAonion 0.75 5 11 4.5 3.3 onion aerial spray GAonion 0.5 10 26 5.5 3.8

omon aerial spray CA onion 0.5 10 8.8 4.0 3.5 ornamental ground spray CA Impervious/ 1.25 4 0.75 0.30 0.23 residential peanut in furrow NC peanut 1.5 2 2.2 0.65 0.4 peanut, ground spray NC peanut 1 3 13 3.5 2.4 cracking peanut,

post- ground spray NC peanut 1 3 18 4.3 2.4 emergence



### 18Application l-in-IO l-in-IO 30- year Use Application EFED Scenario Rate Number of year year average method [lb. a.i./A] applications acute chronic (Ilg/L) (U1!/L) (u1!/L) peanut, ground spray NC peanut 1 3 19 5.0 2.5 pegging peanut, ground spray NC peanut 1.5 2 14 3.3 2.4 cracking peanut,

post- ground spray NC peanut 1.5 2 15 3.5 2.3 emergence

peanut, ground spray NC peanut 1.5 2 23 5.5 2.5 pegging potato aerial spray Me Potatoes 1 4 19 7.5 5.3

rice Not Tier I Rice 0.5 2 175 < 175 applicable Model < 175
stone fruits aerial GA Peaches 1 2 5.5 1.6 1.3 stone fruits aerial MI Cherries 1 2 6.5 2.5 2.0 strawberry aerial spray FL Strawberry 0.5 10 44 11 8.5 strawberry aerial spray FL Strawberry 1.0 1 18 2.5 1.6 turf ground spray PA turf 4 6 92 31 18 turf ground spray FL Turf 4 6 52 18 12 turf ground spray PA turf 1.25 4 14 6.0 3.5 turf ground spray FL Turf 1.25 4 7.3 2.4 1.9



### Results: Groundwater Concentrations of Iprodione TTR SCI-GROW was used to estimate groundwater concentrations resulting from the use of iprodione. SCI-GROW is based on the median Koc 

### (469 mLigoc) 

### and aerobic soil metabolism half-life (19.2 days) ofthe pesticide, the application rate, and the concentration data from 13 

### small-scale groundwater monitoring studies. For the highest application rate (turf, 6 x 4 lb ai/acre), the groundwater concentration oftotal toxic residues is 1.17 )J.g/L. For the proposed new uses on fruiting vegetables and cucurbits and the label amendment for peanuts (3 x 1 lb ai/acre), the groundwater concentration of TTR is 0.15 ug/L. 

### If it is assumed that 75% of applied iprodione becomes 3,5-DCA, the groundwater concentrations ofTTR for turfand new
uses become 0.29 ug/l, 

### and 0.04 

### ,..,gIL, respectively.

DrinkingWaterEstimates for the Degradate 3,5-DCA


### MethodsforDetermining3,5-DCA Concentrations Based on fate data that the registrant has submitted that characterize iprodione degradation in water and soil, 3,5-DCA is formed in each metabolic study. Therefore, it is reasonable to assume that 3,5-DCA can be simulated with the same scenarios as iprodione and with the same molar application rate as iprodione. The same scenarios that were run for iprodione (Table 7) were also run for 3,5-DCA. Application rates for these scenarios are the same as for the equivalent iprodione applications, except that they were adjusted by the molecular weight ratio (162/330), and by an assumed 75% conversion ofiprodione to 3,5-DCA.

19

### Chemical input parameters for 3,5-DCA are summarized in Table 12 for surface water, Table 13 for rice, and Table 14 for groundwater.

As supported by registrant-submitted information, the fundamental assumption employed in this modeling is that a maximum of 75% ofiprodione degrades to 3,5-DCA. Transformation to 3,5-DCA is assumed to be rapid, based on the registrant studies. In the submitted studies, the maximum formation of 3,5-DCA occurred approximately 30 days after the application of iprodione. Additionally, uncharacterized, unextractable residues in aerobic soil studies formed at levels greater than 10% between Day 14 and 30. As 3,5-DCA has been determined to form unextractable residues (MRID 48219201) in aerobic soils, EFED has assumed that the unextractable residues in the iprodione studies would most likely be 3,5-DCA. The assumed rapid formation of3,5-DCA from iprodione promotes high acute concentrations because of the immediate availability of75% ofapplied parent as 3,5-DCA. This is conservative in that slower formation would result in lower peak concentrations, though not necessarily lower long-term average concentrations. The application dates for 3,5-DCA were adjusted from those of iprodione TTR by 14 days to account for delay in formation. Results, using application rates adjusted for molecularweight, were postprocessedto account for the 75% conversion.

35 DCA tt 

### T bl 12 PRZM/EXAMS'

a e 

# . mpu parame ers or 

## , 

## - PARAMETER (units) VALUE SOURCE COMMENT Application Rate (kg a.i./ha) various (rate for Label See Table 7, above! iprodione adjusted by

molecularweight ratio)

Number ofApplications various Label
Interval between various Label Applications
Molecularweight 160 g/mol Iprodione RED, 1998



### - Henry's Law Constant 10'6atm-mvrnol EPI Suite



### - VaporPressure (torr) 2.7 x 10'9 EPI Suite



### - Solubility in Water @ 20°C, 784 mg/L EPI Suite 

### - pH=8
Soil Organic Carbon 664 ml/g MRID: 43349202 Mean value Partition Coefficient (Koc)
CAM (Chemical Application 2 Input Guidance. Method) Depth ofIncorporation 4cm Iprodione label. A default of4 em was used, unless label specified differently Application efficiency Ground spray: 0.99 Input Guidance. Aerial spray: 0.95 Spray drift fraction Ground spray: 0.064 Input Guidance.



### 203,5,DCA application rate

- iprodione application rate adjusted bymolecularweight ratio (162/330 - 0.49) PARAMETER(units) VALUE SOURCE COMMENT Aerial spray: 0.16 Application date various Labels See Table 6 Hydrolysis Half-life Assumed Stable No data 3,5-DCA assumed stable Aqueous Photolysis Half-life Assumed Stable No data 3,5-DCA assumed stable @pH7
AerobicAquatic Metabolism 129 No data 2 x aerobic soil metabolism Half-life value
Anaerobic Aquatic Assumed Stable No data 3,5-DCA assumed stable Metabolism Half-life
Aerobic Soil Metabolism 64.5 MRIDs: 43091002, 95% DCL around mean value Half-life 45239201,48219201 from seven values

I


### 35 DCA tt 

### T bl 13 

### T" I Ri 

### M d I .

a e 

## . rer 

### ce 0 

### e mpu 

### parame ers or 

# . - Input Parameter Value Source Comment 3,5-DCA applicationrate = Annual Application Rate 0.49Ib./A Label iprodione application rate adjusted bymolecularweightratio (162/330

= 0.49) Soil Organic Carbon 662 mIlg MRID: 43349202 Mean of4 soils Partitioning Coefficient (Koc )


### 35 DCA I 

### tt T bl 14 SCI GROW ( 23)·

a 

### e 

# . - v. mpu 

### parame er va ues or 

## , 

# - Input Parameter Value Source Comment 3,5-DCA application rate = Maximum Application Rate (lb Turf: 1.96 Label iprodione application rate a.i./A) adjusted by molecular weight ratio (162/330 =0.49) These represent highest and Number ofApplications per Year Turf: 6 Label lowest annual applications (see Table 6, above) Organic Carbon Partition 626 mIlg MRID: 45114101 Median Koc Coefficient (Koc) Aerobic SoilMetabolism Half-life 49 days MRIDs 45239201, Median aerobic soil metabolism 48219201,43091002 half-life



### Results: 

### Surface Water Concentration of Degradate3,5-DCA Results for surface water concentrations of 3,5-DCA are given in 

### Table 15 for 

### PRZM/EXAMS surface water simulations. As with the TTR, the highest concentrations (excluding rice) resulted from the Pennsylvaniaturfscenario, with an acute concentration of115 

### ug/L, a chronic concentration of 42 

### ug/L, and a cancer concentration of 27 .uglL. 

### For groundwater, the EDWC was 0.81 ug/L for the turfapplication and 0.1 for the proposed new uses (fruiting vegetables and cucurbits) and label amendments to peanuts.

21

### . hi h35DCA I 

### f f 

### f 

### 5 S Table 1 . ummary 0 

### sur ace water simu a Ions resu mgm IgJ 

## , - concentrations l-in- l-in-l0 30- Application Application Number of 10 year year Use method EFED Scenario Rate applications year chronic average [lb. a.i./A] acute (JiglL) (ug/L) (Jig/L) almond! ground spray CAAlmond 0.19 4 5.1 1.7 1.2 pistachio almond! aerial spray CA Almond 0.19 4 7.8 2.6 2.1 pistachio

bean aerial spray MI Beans 0.56 2 21 8.5 6.0 bean aerial spray OR Beans 0.56 2 13 4.1 2.9 berries ground spray OR Berries 0.37 4 7.9 3.6 2.7 broccoli ground spray CA Cole crop 0.56 2 27 10 5.7

carrot aerial spray FL Carrot 0.37 4 46 8.9 5.0 carrot aerial spray FL Carrot 0.38 10 41 9.2 5.5 chinese ground spray FL cabbage 0.19 4 12 3.2 2.0 mustard cotton in furrow CA Cotton 0.10 1 0.038 0.023 0.0075 cotton in furrow MS Cotton 0.10 1 0.58 0.098 0.045 cotton in furrow NC Cotton 0.10 1 0.31 0.083 0.060
cucurbits ground FL cucumber 0.74 2 0.25 0.16 0.060 incorporate cucurbits ground FL cucumber 0.37 3 0.22 0.14 0.060 incorporate cucurbits ground CAmelon 0.74 2 32 4.2 2.3 incorporate cucurbits ground CAmelon 0.37 3 28 4.6 3.0 incorporate fruiting ground CA tomato 1.10 1 1.9 0.65 0.34 vegetables incorporate

fruiting ground CA tomato 0.74 2 3.3 1.3 0.68 vegetables incorporate

fruiting ground CA tomato 0.37 3 5.4 1.8 0.83 vegetables incorporate

fruiting ground FL peppers 1.10 1 14 1.7 1.1 vegetables incorporate

fruiting ground FL peppers 0.74 2 28 4.1 2.6 vegetables incorporate

fruiting ground FL peppers 0.37 3 36 5.4 3.8 vegetables incorporate

fruiting ground FL tomato 1.10 1 9.0 1.4 0.65 vegetables incorporate

fruiting ground FL tomato 0.74 2 18 3.2 1.7 vegetables incorporate

fruiting ground FL tomato 0.37 3 28 4.9 2.7 vegetables incorporate

fruiting ground PA tomato 1.10 1 4.6 1.2 0.71 vegetables incorporate

fruiting ground PA tomato 0.74 2 8.0 2.9 1.8 vegetables incorporate



### 22l-in- l-in-l0 30- Application Application Number of 10 year year Use method EFED Scenario Rate applications year chronic average [lb. a.i.IA] acute (l1g lL) (l1g lL) (ulZlL) fruiting ground PA tomato 0.37 3 13 5.0 3.0 vegetables incorporate

garlic in furrow CA garlic 0.74 1 0.72 0.18 0.083 grapes ground spray NY Grapes 0.37 4 35 16 9.1 grapes ground spray CA Grapes 0.37 4 5.4 2.9 2.3
lettuce aerial/ground CA lettuce 0.37 3 20 7.6 5.1 spray lettuce ground spray CA lettuce 0.37 3 20 6.8 3.8 onion aerial spray GA onion 0.28 5 33 6.3 4.1 onion aerial spray CA onion 0.28 5 13 5.2 4.3 onion aerial spray GA onion 0.19 10 43 10 6.2

omon aerial spray CA onion 0.19 10 13 6.0 5.4
ornamentals ground spray CA Impervious/ 0.46 4 1.2 0.43 0.34 residential peanut in furrow NC peanut 0.56 2 3.5 0.85 0.44 peanut, ground spray NCpeanut 0.38 3 25 6.7 3.9 cracking peanut, ground spray NC peanut 0.38 3 25 6.7 3.8 postemergence peanut, ground spray NC peanut 0.38 3 21 5.6 4.0 pegging peanut, ground spray NC peanut 0.56 2 25 6.6 3.8 cracking peanut, ground spray NC peanut 0.56 2 30 7.4 3.8 postemergence peanut, ground spray NC peanut 0.56 2 24 6.0 4.0 pegging potato aerial spray Me Potatoes 0.37 4 25 11 8.2

rice Not applicable TierI Rice 0.19 2 211 <211 <211 Model stone fruits aerial GA Peaches 0.37 2 9.8 2.6 2.0 stone fruits aerial MI Cherries 0.37 2 9.8 4.2 3.3 strawberry aerial spray FL Strawberry 0.19 10 63 16 13 strawberry aerial spray FL Strawberry 0.37 1 20 3.9 2.4 turf ground spray PA turf 1.47 6 115 42 27 turf ground spray FL Turf 1.47 6 80 25 17 turf ground spray PAturf 0.46 4 22 9.2 5.6 turf ground spray FL Turf 0.46 4 12 4.3 3.0



### Drinking WaterTreatmentEffects No specific information on the effects of drinking water treatment are available for iprodione or its degradates 3,5-DCA, RP30228, RP35606, or RP32490. The EDWCs in this assessment are representative ofconcentrations in drinking water source water (pre-treatment)

23

### and are derived from daily instantaneous peak concentrations. For surface water, the conceptual model assumes that a pesticide reaches surface water via spray drift and surface runoff. In the water body the pesticide is assumed to be instantaneously completely-mixed. Iprodione TTR is relatively stable to hydrolysis, and may therefore not degrade by hydrolysis during the time that elapses from drinking water intake through distribution to the first tap. Because ofits somewhat low Koc 

### values, treatment methods such as sedimentation and flocculation are not expected to be effective at removing iprodione or its degradates. Iprodione also does not degrade due to photolysis. Ifultraviolet light were used as a means ofdisinfection, degradation ofiprodione would not be expected.
Uncertainties and Data Gaps 

### Prominentuncertainties include the characterization and quantification ofthe degradation of iprodione and 3,5-DCA. Uncertainties also are associated with the formation of 3,5-DCA. Degradation quantification was confounded by large amounts ofunextracted material that were reported in the degradation studies conducted with soil for both iprodione and 3,5-DCA. The large amount of unextracted and uncharacterized material hinders accurate estimation of degradation rates, but does tend to suggest that iprodione might degrade very slowly in soil. However, aerobic soil metabolism studies on 3,5-DCA have demonstrated that it binds to soil as unextractable residue (MRID 48219201). Acceptable aerobic soil metabolism data are only available for iprodione on one soil. Current data requirements specify a total offour soils. If additional soils were assessed with an analytical method that could minimize unextractable residues, this source ofuncertainty could be reduced.

As mentioned in the Environmental Fate section (p 

### 6), the primary means for iprodione degradation in aquatic systems appears to be via hydrolysis. In modeling EDWCs for the iprodione TTR, degradation via hydrolysis and aerobic aquatic metabolism were incorporated into the model runs. In both studies, the primary degrade ofiprodione at pH 9 was RP 30228. In the hydrolysis study (MRID 41885401), maximum formation ofRP30228 occurred in a very quickly (93% at 107 minutes), while in the aerobic aquatic metabolism study (MRID 41927601/42503801) 

### the maximum formation ofRP30228 occurred at a much slower rate (65% at 14 days). As the rates observed in the hydrolysis study were faster for both the parent and the TTR than the rates observed in the aerobic aquatic metabolism study, hydrolysis could be affecting the degradation rates observed in the aerobic aquatic metabolism study and using both degradation rates in the model could result in a "double counting" ofthe degradation, resulting in
anunderprediction ofthe EDWCs. There is uncertainty in EFED's assumption that 75% of the applied iprodione is converted to 3,5-DCA. EFED has based this assumption on the levels of unextracted and uncharacterized residues found in aerobic soil metabolism studies and that other studies indicate that 3,5-DCA is the terminal degradate of iprodione and that it binds unextractably to soil. However, because the unextractable residues from the irpdodione aerobic soil metabolism studies were not characterized as being 3,5-DCA, the 75% conversion rate could be an overestimate, resulting in overpredictedEDWCs from the models. There is uncertainty associated with general model representativeness, as well as with the selection ofinput parameters. In this regard, one ofthe potentially importantparameters that can

24

### impact concentration estimates is the selection of application dates. Although the pesticide application dates were selected to be most appropriate according to the model user's best judgment and with considerations for label restrictions and simulated cropping dates, uncertainty nevertheless results because the application window (the time span during a season that a pesticide may likely be applied) for a pesticide may be wide and actual application dates are unknown. Such uncertainty is a function oftemporal proximity ofpesticide applications to rain events.

The Tier II drinking water assessment relied on maximum use patterns. To the extent that actual use patterns are less than the labeled maximums, actual environmental exposures could be lower. Additionally, because iprodione can be used on turf, no adjustment was made to account for percent cropped area. To the extent that the location-specific PCAs are less than assumed in this assessment, actual environmental exposures couldbe lower.

While monitoring data for iprodione and 3,5-DCA indicated much lower levels ofthese analytes in surface water or groundwater, other thanthe focused monitoring for golfcourses and plant nurseries conducted by Bayer Cropscience between 2006 to 2009, monitoring was not targeted specifically at iprodione use areas or conducted during times ofknown iprodione use, and as such may not reflect potential peak iprodione concentrations that may occur in surface waters when runoffevents occur shortly after application. Adding to this uncertainty, reporting limits for some ofthe data have varied over the years. The Suffolk County Drinking Water Database did not report trace levels (e.g., levels above the method detection limit but below the reporting limit), which would have facilitated interpretation of their drinking water source monitoring results. Lastly, great uncertainty surrounds levels of the iprodione TTR 

### in the environment, as monitoring data for the other three residues ofconcern (RP30228, RP35606, or RP32490) are not available.

In the case ofthe targeted study conducted by Bayer (MRIDs 47579101 and 47881501), annual iprodione sales data and acreages for golfcourses and watersheds were provided. Based
on these data, annual use estimates, in pounds ai per acre, were developed for the golfcourses and the watersheds 

### (Table 16). Compared to the modeled runs for turf(maximum annual usage of24 lbs ailA), while the annual amount used on the golfcourses is lower, the data indicate that annual use rates close to the 24 lbs ailA maximum have actually been observed, particularly in the Rahway, 

### NJ watershed. The surface water modeling for turfassumes apercent cropped area adjustment factor of 1, which means the entire watershed is treated with iprodione. Taking the acreage ofthe Rahway watershed into account, area-averaged annual application rates in this watershed are as much as four orders ofmagnitude less than the 24 lbs ailA maximum used in modeling. Ifthe results from the 

### PRZM/EXAMS runs were scaled using the maximum average watershed annual use rate (0.065 lbs ai/A watershed), the EDWCs would all be below 1 ug/L. 

### For 3,5-DCA, the same scaling would result in EDWCs below 0.5 ug/L. These scaled values are
more comparable to the results provided in Bayer's surface water monitoring study, which reported concentrations ofiprodione and 3,5-DCAbelow 0.56 ug/L and 0.1 ug/L, respectively.



### Table 16. Iprodione sales data during monitorina study, 2004-2008 Lbs ai/Total Acres 

## I Bradenton, FL 

## I Rahway, NJ* 

## I (n=12) (n=18) 

### Annual iprodione use per acre ofgolfcourse

25 Aurora,lL (n=lll)Average ± Std Dev 

## I 0.73 ± 0.43 

## I 6.56 ± 7.22 

# I 1.50± 1.89 (Min-Max) (0.12 - 1.36) (0.53 - 21.5) (0.13 - 14.7) Annual iprodione use per acre ofwatershed Average ± Std Dev 

# I 0.002 

# I 0.065 

# I 0.002 (Min-Max) (0.001

- 0.004) (0.006 - 0.091) (0.001 - 0.002)

The estimates from the Tier I Rice Model are screening-level estimates and, as such, are expected to generate high-end EECs that are likely to exceed peak concentrations ofpesticides in waterbodies downstream ofrice paddies. Neither degradation ofthe pesticide nor mass transfer from the aqueous phase to the sediment is considered in the model's conceptualization. The absence ofdegradation adds conservatism to the model (i.e., estimated concentrations should be higher than those usually found in rice paddies). The absence ofmass transfer processes can either add or reduce conservatism depending on various conditions such as whether the pesticide is soil or water applied, and whether actual degradation occurs more rapidly in the sediment or the water compartment. Lastly, it should be noted that this assessment only examines the formation of3,5-DCA from the degradation of iprodione. 3,5-DCA is also formed during the degradation of the fungicide vinclozalin. While annual use rates (Appendix 2), estimated by the USGS NAWQA program, indicate the use ofvinclozalin in 2002 was roughly 11% that ofiprodione use (52,000 lbs versus 460,000 lbs), the data also indicate that both fungicides may be used in the same watersheds. As such, EDWCs for 3,5-DCA may be underestimated to a degree that is not known.


### CONCLUSIONS

Revised EDWCs for iprodione and 3,5-DCA are presented in 

### Tables 1 and 2. Acute concentrations for iprodione from all ofthe modeled crops (excluding rice) fell in the range of 0.01 to 92 ug/L; chronic concentrations were in the range of 0.0 to 31 ug/L; and cancer concentrations were in the range of0.0 to 18 ug/L. Acute concentrations for 3,5-DCA from all of the modeled crops (excluding rice) fell in the range of 0.04 to 115 ug/L; chronic concentrations were in the range of0.02 to 42 ug/L; and cancer concentrations were in the range of0.01 to 27 ug/L, Groundwater concentrations for the highest annual use ofiprodione (24 lbs ai/A) were 0.29 and 0.81 ug/L for iprodione and 3,5-DCA, respectively.


### REFERENCES

CaliforniaDepartment ofPesticide Regulation (CDPR) Surface Water Database. Searched 3/15/2011. http://cdpr.ca.gov/docs/emon/surfwtr/surfcont.htm
Jones, R. D., S. Abel, W. R. Effland, R. Matzner, R. Parker. 1998. An Index Reservoir for Use in Assessing Drinking WaterExposure. Proposed Methods for Basin-scale Estimation of Pesticide Concentrations in Flowing Water and Reservoirs for Tolerance Reassessment. Presentationto FIFRA Science Advisory Panel, June 29-30, 1998. Online at: http://v.ww.epa.gov/scipoly/sap/1998/index.htm

26USEPA. 1998. ReregistrationEligibility Decision Iprodione. USEPAJOffice ofPrevention, Pesticides, and Toxic Substances. EPA738-R-98-019. November 1998

USEPA. 2002. SCIGROW: Users Manual. Online at: http://\\'\\w.epa. gO\!oppefed1imodels/\vater!#sci2.row

USEPA 2006. Memorandum: Standardized Soil Mobility Classification Guidance. Environmental Fate and Effects Division. April 21, 2006.

USEPA 2007a. Iprodione drinking waterassessment, including proposed new use on pistachio (IR4) and label revisions affecting rates for strawberries, stone fruits, and grapes. D285550. March 6, 2007.

USEPA. 2007b. Tier I Rice Model Manual. Online at:

USEPA. 2009. Guidance for Selecting Input Parameters in Modelingthe Environmental Fate and Transport ofPesticides. U.S. Environmental ProtectionAgency, Office ofchemical Safety and PollutionPrevention, Office ofPesticide Programs, Environmental Fate and Effects Division, Oct. 22, 2009. Online at: http://wvvw.epa.gov/oppefedl/models/water/inputparameterguidance.htm

USEPA. 2010. Development and Use ofPercent CroppedAreaAdjustmentFactors in Drinking WaterExposure Assessments. U.S. Environmental Protection Agency, Office ofchemical Safety and PollutionPrevention, Office ofPesticide Programs, Environmental Fate and Effects Division, September9, 2010. Online at:**http~!\v\vw.epa.goYioppefedl/models\\ater!pca** adjustment dwa.html

USEPA. 2011. Memorandum: Iprodione drinking water assessment for label amendments and proposed newuses on fruiting vegetables and cucurbits. Environmental Fate and Effects Division. April 5, 2011. DP Barcode: D385307.

USEPA. 2011. Memorandum: Iprodione; Report ofthe Residues ofConcern Knowledgebase Subcommittee (ROCKS). Health Effects Division. October 5,2011. DP Barcode: D393960.

USGS National Water Quality Assessment Data Warehouse (NAWQA). Searched 3/7/2011. http://infotrek.er.usgs. gOYInawqa queries/swmaster/index.jsp


### MRIDs

MRID: 41755801 Spare, W. (1990) Anaerobic Aquatic Metabolism ofIprodione: Lab ProjectNumber: 1510. Unpublished study prepared by

### Agrisearch Inc. 114 p.

27

### MRID: 41861901 Adrian, P.; Robles, J. 

### (1991) Carbon 14-Iprodione: Aqueous Photolysis: Lab ProjectNumber: 90/22: AG/CBLD/AN/9115524. Unpub-lished studypreparedby Rhone-Poulenc SecteurAgro. 97 p.

MRID: 41877401 Norris, F. (1991) A Terrestrial Field Soil Dissipation Study with Iprodione: Lab ProjectNumber: 40644: EC/P-89-0013. Unpublished studypreparedby Rhone-Poulenc Ag Co.; A & 

### L Eastern Agricultu- ral Labs, Inc.; Morse Labs., Inc. 275 p.

MRID: 41885401 Das, Y. 

### (1990) Hydrolysis ofPhenyl(U)-carbon 14 Iprodione in Aqueous Solutions Buffered at pH 5, 7 and 9: Lab ProjectNumber: 89100. Unpublished studyprepared by Innovative Scientific Services, Inc. 96 p.

MRID: 41927601 Spare, W. (1991) Aerobic Aquatic Metabolism ofIprodione: Lab Pro-jectNumber: 1514. Unpublished studypreparedby Agrisearch Inc. 147 p.

MRID: 42503801 Spare, W. (1992) Aerobic Aquaticc Metabolism ofIprodione: Supplemental ReportMRID 419276011: Lab ProjectNumber: 1514. Unpublished studypreparedby Agrisearch Inc. 117 p.

MRID: 43091002 Waring, A. 

### (1993) (carbon 14) Iprodione: Aerobic Soil Metabolism: Final Report: Lab Project Number: 68/132: 68/132-1015. Unpublished studypreparedby HazletonEurope. 105 p.

MRID: 43349202 Burr, C.;

### Newby, S. (1994) Iprodione: Adsorption/Desorptionto and from Four Soils and an Aquatic Sediment: Lab ProjectNumber: P94/014. Unpublished studypreparedby RhonePoulenc Agriculture Ltd. 81 p.

MRID: 43718301 Chancey, E. 

### (1995) AnAquatic FieldDissipation Studywith Iprodione: Lab ProjectNumber: 44729: EC-92-187: FAD-IPR-RI-MS-92. Unpublished studyprepared by Rhone-Poulenc Ag Co.; Agvise, Inc.; and SouthTexas Ag Research Inc. 374 p.

MRID: 44590501 Waring, A. 

### (1993) (carbon 14) Iprodione: Soil Degradation: Final Report: Lab ProjectNumber: 68/139-1015. Unpublished studypreparedby HazletonUK. 73 p.

MRID: 45114101 Feung, C. (1999) Iprodione Metabolite: (carbon-14)-3,5-Dichloroaniline Soil Adsorption/Desorption Study: Lab ProjectNumber: 99R16744. Unpublished studypreparedby Rhone Poulenc Ag Company. 165 p.

28

### MRID: 45239201 Quarmy, D. (2000) Iprodione Metabolite: (carbon-14)-3,5-Dichloroaniline Aerobic Soil Metabolism: Lab ProjectNumber: 99R16743. Unpublished study prepared by Springborn Laboratories, Inc. 282 p.

MRID: 47778802 Miller, R. (2009) ProductProperties: Color, Physical State, Odor, Stability to Normal and Elevated Temperatures, Oxidation/Reduction: Chemical Incompatibility, pH, UV/Visible Absorption, Melting Point/Melting Range, Density, Partition Coefficient (n-Octanol/Water), Water Solubility, and VaporPressure (Iprodione Technical). ProjectNumber: CHB/EX/609/011/P/l. 

### Unpublished study preparedby PhibroWood, LLC. 37 p.

MRID: 47881501 Xu, T. (2009) Surface Water Monitoring for Residues ofIprodione in high Use Areas in the United States. Study Number: RAIDXOOl. Unpublished study preparedby Bayer Cropscience. 251 p.

MRID: 48219201 Woodard, D. (2010) [Pheyl-UL-14C]-3,5-dichloroaniline: Aerobic Soil Metabolism in Two US Soils. StudyNumber: MEIDY002. Unpublished studypreparedby Bayer Cropscience. 83 p.

29

### Appendix 1. Iprodione and Degradate Data

t I

### fat t 

### di 

### d" d 

### t f d 

### a 

### eo ipro 

### tone ezra a es orme In 

### environmen a e s U 

### res

Degradate Chemical Name Study in Which Found (Maximum % Reference Name ofApplied) MRID RP32596 1 3,5-dichloroaniline Aerobic Soil (9%, Day 30) 43091002 (or 3,5-DCA) Aerobic Soil (3.9%, Day 50) 44590501 Aerobic Aquatic (9.9%, Day 30) 42503801 Anaerobic Aquatic (3.6%, Day 275) 41755801 RP30228 3-(1-methy1ethyl)-N-(3,5- Hydrolysis (47%, pH 7, 125 hours) 41885401 dichloropheny1)-2,4-dioxo-1- Hydrolysis (93%, pH 9, 120 minutes) 44590501 imidazolidine-carboxamide Aerobic Soil (29%, Day 30) 42503801 Aerobic Aquatic (65%, Day 14) 41755801 Anaerobic Aquatic (67%, Day 14) 41877401 Terrestrial Field (0.47 ppm, Day 28) 43718301 Aquatic Field (0.13, I month after app) RP25040 3-(3,5-dichlorophenyl)-2,4- Aerobic Soil (9.5%, Day 30) 43091002 dioxoimidazolidine RP32490 3-(3,5-dichlorophenyl)-2,4- Aerobic Aquatic (15%, Day I) 42503801 dioxo-l-imidazolidine- Terrestrial Field (0.09 ppm, 8 months 41877401 carboxamide after app) RP37176 N-(3,5-dichlorophenyl)-2-(1- Aquatic Field (0.13 ppm, Day 13) 43718301methylethyl)-lureylenecarboxamide RP35606 [(dichloro-3,5-phenyl)-I- Hydrolysis (12%, pH 5, Day 30) 41885401 isopropylcarbamoyl-3]-2- acetic acid RP36221 1-(3,5-dichlorophenyl)-5- Aerobic Soil (13%, Day 100) 44590501 isopropyl biuret Unextractable Aerobic Soie (51%, Day 100) 44590501 residues Aerobic Soil (76%, Day 276) 43091002 Aerobic Aquatic (8%, Day 30) 42503801 Anaerobic Aquatic (29%,6 months) 41755801 

### T hI f i

1. The terrestnal field studies did not analyze for 3,5-DCA. Storage sample recovenes for 3,5-DCA in the aquatic field were only 18%; thus, it was not suitable for characterizing the formation or persistence of 3,5-DCA. 2. Unextractableresidues not measured, but total extractable residues were at 49% at Day 100.
d 

### t dd 

### d" Itt Ch

### enuca S 

### rue ure or 

### ipro ione an mawr 

### eara a es Chemical Structure Iprodione 

# r CH,

# 0=<'JNANH~

- CH. 

# "-d -,

Cl 3,5-Dichloroaniline CI\ RP32596 

# ?**>--~** 01



### 30Structure Chemical 

### :3-**l-methylethyl)-N-(3,5-dichloroph~nyl)-**

# co-~ (, l' idazolidine-carboxamide 2,4-dIOXO- -im 

# * RP30228

# ~CE(CE')' Q
H**3-(3,5-dichlor~p~enyl)-2,4-** 0 CI dioxoimidazolidine 

# J-Y-© RP25040

CI 3-(3,5-dichlorophenyl)-2,,4-dioxo-l- n

# od_L~ imidazolidine-carboxamide RP32490

C1 C3 N-(3**,5-dichlorophen~** 1)-2-(I-methylethyl)- 

# cp-**/~** l-ureylenecarboxamide

, NHCOCt\NHCOCH<, RP37176 CHI



### - Cl [(dichloro-3,5-phenyl)-1- , id CI Cli. OOOH

# ~NH ........LC-NH-cHICHJ' ' I arbamoyl-3]-2-acetIc aCI isopropy c II \I RP35606 

### o 0 C 5 ' opyl biuret 

# b---rm-A-naC: 1-(3,5-dichlorophenyl)- -isopr RP36221

Cl



### 31

### Proposed route ofdegradation, from aerobic soil metabolism study (MRID 43091002)



### structure tonrlrmed b)' tC/MS**ll.P2~040**



# ***.~** 0 e,**"'~** I'

,**~)**

...**::~~. -~**  ... .,)=**i""'''~'':'-o** '::1"-

..... ri"

CQ.H(;HIc:

....COOIot I C::l 

# ;'-'='"'QI**o~_I/** .•. el

llPJOZZB



### 32 ) c'

...... } '<:: ;,

...**'.~'**

# "
:"":1 RPl6112

I<PJ6 U9'

### Appendix 2. Usage Data from USGS NA WQA Program



### IPRODIONE

-fungicide 2002estimated annualagricultural use

Averageannualuse of activeingredient (pounds persquaremileofagricultural landincounty) 

## o noestimated use [] 0.001 to 0.003 III 0.004 to 0.009 

## o 0.01 to 0.042 

## o 0.043 to 0.345 • >=0.346 Total Percent Crops nnunds anplled**n~tlonal** use cotton 133254 27.04 almonds 116979 23.74 potatoes 57463 11.66 lettuce 54408 11.04 dry onions 24562 4.98 grapes 19097 3.87 peaches 19084 3.87 carrots 18930 3.84 cherries 9973 2.02 nectarines 7688 1.56



### VINCLOZOLIN

- fungicide 2002 estimatedannualagriculturaluse

Average annual use of active Ingredient (poundspersquare mile ofagricultural landincounty) 

## o no estimateduse 

## o 0.001 to 0.002 0.003 to 0.008 

## o 0.009 to 0.034 IJ 0.035 to 0.146

• >=0.147 Crops lettuce green beans Idwlfrun



### 33 Total Pounds Applied

30011 20611

1218 Percent National Use 58.00 39.84 2.35j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j j