OFFICE OF
CHEMICAL SAFETY AND
POLLUTION PREVENTION UNITED STATES ENVIRONMENTAL PROTECTION AGENCY WASHINGTON D.C., 20460



### December 12 , 2011

PC Code: 044312

DP Bar Code: D 394848

MEMORANDUM

SUBJECT: Tier I Human Health Drinking Water Assessment of Dinotefuran and its

Transformation Products of Concern ( MNG, DN, UF and DN

- 2

- OH + DN

- 3

- OH ) in Support of Proposed IR

- 4 New Uses (Onion, Bulb and Green; Berry and Small Fruit; Tuberous and Corm Vegetables ; Peach; and Watercress)

TO: Sidney Jackson, Risk Manager Reviewer Barbara Madden, Team Leader Risk Integration, Minor Use and Emergency Response Branch Registration Division (7505P)

and Barry O’Keefe , Biologist Paula Deschamp, Branch Chief Registration Action Branch III Health Effects Division (7509P)

FROM : Ronald Parker

, Ph.D., Senior Environmental Engineer

Environmental Risk Branch III Environmental Fate and Effects Division (7507P)

THROUGH: Dana Spatz, Chief

Environmental Risk Branch III

Environmental F ate and Effects Division (7507P)

Executive Summary

This memo summarizes the Environmental Fat e and Effects Division’s (EFED) Tier I human health drinking water assessment of dinotefuran and its transformation products of concern ( MNG, DN, UF and DN

- 2

- OH + DN

- 3

- OH ) in s upport of the f ollowing p roposed n ew IR

- 4 u ses: Onion, Bulb and Green (Subgroups 3

- 07A and 3

- 07B) ; Berry and Small Fruit (Subgroups 13

- 07F and 13

- 07H); Tuberous and Corm Vegetables (Subgroup 1C); Peach; a nd Watercress

.

Resulting EDWCs for parent dinotefuran for the two terrestrial crop groups with the highest annual application amount are 33.4 μg/L for surface water acute risk, 5.5 μg/L for surface water

chronic risk and 1.07 μg/L for groundwater. ( Background information on the FIRST and

SCIGROW model s and output file s for crop groups 1C and 13

- 07F are included in Appendix 1 at

the end of this assessment )

.

### Below see also the qualitative assessment performed for watercress which is typically cultivated in shallow, flowing water. The Agency does not currently have a methodology for exposure assessment for crops cultivated in flowing water. The EFED tier 1 rice model has therefore been

used as the basis of the exposure assessment and the results have been characterize d to reflect

differences between the conditions represented in th e rice model and the actual methods of

watercress cultivation. The three main differences are (1) simulation of application efficiency (fraction of amount applied which is intercepted by the crop), (2) simulation of degradation of the pesticide in water after application and (3) simulation of flow through and downstream from

the area of cultivation. Consideration of these three differences from the rice model plus

extensive runoff dilution fro m areas of the watershed which are not used for watercress cultivation would be expected to produce concentration values substantially less than those of other labeled crops.

All values are less than the previous EDWC values calculated by EFED for pome an d stone

fruit s (D389034) (Table 1). Therefore

, the pome and stone f ruit EDWCs are still recommended for assessing dinotefuran residues in drinking water. The drinking water assessment was conducted for total dinotefuran residues including parent

, MNG, DN, UF

, DN

- 2

- OH

, DN

- 3

- OH as recommended by the OPP Health Effects Division. T otal EDWC s for dinotefuran residues in surface source drinking water are not expected to exceed 91.31 μg/L for the 1 in 10 year daily peak concentration and 25.16 for the 1 in 10 year annual average concentration. In ground water, the EDWC for dinotefuran residues is not expected to exceed 3.5 μg/L

. No surface and ground water monitoring data are available for dinotefuran.

Table 1

. E stimated D rinking W ater C oncentrations for Dinotefuran Total Residues ( Parent + Degradates ) f or Use on Tuberous and Corm Vegetables (Crop Subgroup 1C), Berry and Small Fruits (Crop Subgroup 13

- 07F), and on Pome and Stone Fruits

Crop (Scenario) Percent
Cropped

Area
(PCA) Acute (peak)

Surface Water

Concentration

( 

### μg/L ) Annual Average

Surface Water

Concentration

( 

### μg/L ) Ground Water

Concentration

( 

### μg/L )

Tuberous and Corm Vegetables

C rop S ubgroup (1C) ; Berry and

Small Fruit C rop S ubgroup ( 13

- 07F)



### . ( 1 aerial appl @ 0.338 lbs

ai/A) Parent Only 100% 1 33.4 5.5 1.07



### Degradates

MNG 100% 1 

### 2.67 1.12 0.33

DN 100% 1 

### 5.38 2.28 0.07

UF 100% 1 

### 2.82 1.42 0.12

DN

- 2

- OH 2 100% 1 

### 8.23 4.09 0.37
Parent + All Degradates

Tuberous and Corm Vegetables crop subgroup (1C) ; Berry and

Small Fruit crop subgroup ( 13

- 07F)



### . (Assuming All Peaks Occur Simultaneously) 100% 1 

### 52.51 14.42 1.97

### Document 044312 D389034 Dinotefuran Section 18 Drinking Water , May 26, 2011

Parent + All Degradates
(Pome & Stone Fruits) ( 2 aerial
appl @ 0.304 lbs ai/A) (Assuming
All Peaks Occur Simultaneously) 100% 1 91.31 25.16 3.5

1 http://www.epa.gov/oppefed1/models/water/pca_adjustment_dwa.html

2 DN

- 2

- OH represents DN

- 2

- OH+DN

- 3

- OH. These two were reported as one metabolite in MRID 45640105

.



### Models Used and Modeling Inputs

The estimated drinking water concentrations for all terrestrial crops in th is e xposure assessment
were estimated using the screening

- level FQPA Index Reservoir Screening Tool ( FIRST ) model

. The Tier 1 SCIGROW model was used to estimate concentrations in groundwater. Background information on the FIRST and SCIGROW models is included in Appendix 1 , Page 15 of this

report, at the end of this assessment.) For watercress, the only aquatic

- based crop, the Tier 1 rice

model was used. Watercress i s grown in shallow, flowing water and c annot be simulated with the

FIRST model. All model out put files and a description of the EFED Tier 1 rice model are also included in Appendix 1

.

Modeling inputs for parent dinotefuran are presented in Table 3

. Modeling inputs and the

calculation method used for the four degradates i s included in the dinotefuran drinking water

assessment for leafy brassic a greens ( See 044312 D357111 DWA Dinotefuran Leafy Brassica Greens, January 23, 2009 in Appendix 2 at the end of this report. ). Under this method, e ach degradate is formed at the same ratio to the parent concentration in the previous assessments

.

The peak parent to peak degradate concentration ratios used in these assessments are i ncluded in Table 2.

Table 2 . Dinotefuran peak parent to peak degradate concentration ratios



### Degradate concentration values are therefore calculated based on the magnitude of the parent compound. All peak concentrations are conservatively assumed to occur simultaneously. See also a complete summary of physicochemical properties and environmental fate a nd transport
data for parent dinotefuran and d egradates in Tables 8

- 1 3

.

Table 3

. Summary of FIRST , SCIGROW and EFED Tier 1 Rice Model Input Values for

Dinotefuran

Environmental Fate

Parameter Value Justification Source

Water Solubility 39,830 mg/L Measured value MRID 45640112 

### Parent/Acute Parent/Annual Ave Parent/GrWater

Dinotefuran Ratio Ratio Ratio

MNG 0.080 0.204 0.313

DN 0.161 0.415 0.069

UF 0.084 0.259 0.116

DN

- 2

- OH 1 

### 0.246 0.744 0.342

### Table 3

. Summary of FIRST , SCIGROW and EFED Tier 1 Rice Model Input Values for

Dinotefuran

Environmental Fate

Parameter Value Justification Source

Organic Carbon Partition Coefficient (K

oc ; mL/g) 30.1 (FIRST)

6 (SciGrow) FIRST: Represents the mean of the following values: 42, 45, 42, 6, 22

, 23.3, 31.4, 33.6, 25.3 mL/g for the parent compound.

SciGrow: represents the lowest value MRID 45640114

, 45640115

Partition Coefficient (K d ; mL/g) 0.656 (Tier1 Rice Model) Mean K d (from the following values: 1.01, 0.71, 1.22, 0.12, 0.22 L/kg) MRID 45640114

Aerobic Soil Metabolism Half

life (days) 68 (FIRST)

38 ( SciGrow ) FIRST: Represents the 90 th percentile

confidence bound on the mean half

life value of the following values: 87.7, 38, 17, 78, 89, 20, 15.9 days (four or more values)

SciGrow: Median value MRID 45640111,

45640112 / 46751101,

46711201

Aerobic Aquatic Metabolism

H alf

- life (days) 82.7 (FIRST) Represents the 90 th percentile

confidence boun d on the mean half

life. Two available values: 79.3 and 76.0 days; mean=77.65 days; standard dev.= 2.3335 days MRID 45640117

Aqueous Photolysis Half

- life (days) 1.8 (Rice) Single Available Value MRID 45 640105



### Characterization of Exposure Assessment for Watercress

The only aquatic crop in th is assessment is watercress which is grow n in clean, flowing water 2

- 3 inches deep ( see URL s : http://www.naturesherbal.com/Watercress.htm or http://edis.ifas.ufl.edu/mv151). The Agency does not currently have a methodology for exposure

assessment for crops cultivated in flowing water . The EFED tier 1 rice model has therefore been

used as the basis of the assessment and the results have been cha racterized to reflect differences

between the capabilities of th is model and the methods of cultivation of watercress. The t hree

main differences are (1) simulation of application efficiency (fraction of amount applied which is intercepted by the crop), (2 ) simulat ion of degradation of the pesticide after application and (3)

simulat ion of f low through the area of cultivation. A description of the EFED tier 1 rice model is included in Appendix 1.

Initial Simulation Using Tier 1 Rice Model

The Tier 1 rice model assumes dinotefuran application to watercress growing in a static rice paddy. The only process simulate d by the model is partitioning of the applied chemical between

the 10

- centimeter deep water column and the 1

- centimeter deep sediment layer of the paddy. The partitioning is based on the pesticide’s K d



### . Resulting initial concentration in the rice paddy for parent dinotefuran for a single application of 0.36 pounds a.i.

, assuming an application efficiency of 0.0 (i.e. none of the pesticide remains on the watercress plants ) is 355.4 μg/L

. Under the conservative assumption that the peak concentrations of the parent and all degradates occur

### simultaneously, degradate concentrations for the three degradates formed by aqueous photolysis ( DN plus UF plus DN

- 2

- OH ) would add a total of 49.2 % of the parent concentration. This would yield an overall total of 530.3 μg/L

. Degradation in the paddy is not calculated by the model so the pesticide is assumed to remain at this concentration in the water indefinitely. (Th ese concentrations values by themselves do not represent EDWC values because watercress will not grow under the static water conditions represented in the rice model).

Impact of Simulating Application Efficiency

Under actual conditions of watercress cultivation, the major part of the applied pesticide will remain on

the leaves of the watercress . This fraction is referred to as the application efficiency. The application efficiency goal of 1.0 is never achieved. Th e fraction on the leaves will also degrade and a portion o f it may be wash ed off of the leaves by rainfall into the stream water below. Table 4 presents the impact of application efficiency on the initial concentration in the rice paddy water.

Table 4 . I mpact of Application Efficiency Application Efficiency (fraction) Initial Conc. in the Rice Paddy Water ( μg/L )

0 530.0

0.1 477.0

0.2 424.0

0.3 371.0

0.4 318.0

0.5 265.0

0.6 212.0

0.7 159.0

0.8 106.0

0.9 53.0

1.0 0.0



### Impact of Simulating Pesticide D egradation

Under field conditions, t his concentration will be rapidly reduced through degradation by aerobic aquatic metabolism (half

- life 82.7 days) and aquatic photolysis in the clear, shallow water (half

life: 1.8 days). Combined half

- life i s 1.76 days. Table 5 reflects 30 days of degradation at the

combined degradation rate. This assumes an application efficiency of zero (0.0) and no flow.

Table 4 . Reduction of Initial Dinotefuran Concentration s Parent + Aqueous Photolysis Degradates in Static Rice Paddy W ater Due to Aqueous Photolysis

Day s After Concentration Day s After Concentration Day s After Concentration Application ( μg/L ) Application ( μg/L ) Application ( μg/L )

0 530.300 11 6.968 22 0.092

1 357.669 12 4.699 23 0.062

2 241.236 13 3.170 24 0.042

3 162.706 14 2.138 25 0.028

4 109.739 15 1.442 26 0.019

5 74.016 16 0.972 27 0.013

### 6 49.921 17 0.656 28 0.009

7 33.670 18 0.442 29 0.006

8 22.709 19 0.298 30 0.004

9 15.317 20 0.201 31 0.003

10 10.331 21 0.136 32 0.002

Impact of Simulating Flow through the Cultivated Area

Under actual conditions of watercress cultivation

, the amount of pesticide which reaches the stream water

w ill be re moved continuously downstream from the site at which i t is applied by advection in the flowing

water. The rate of removal depends on the rate of flow through the site. River velocity varies from day to day based on the volume of flow and changing cross

- sectional area. Typical ranges of velocity vary from zero (at the time of tidal flow direc tion change) to 7 miles per hour (URL: http://hypertextbook.com/facts/2006/NervanaGaballa.shtml . The Mississippi River ranges from 1.2 to 3 miles per hour depending on the amount flow a nd the reach in which it is measured. The pesticide in the flowing water will also spread from the center of mass during the flow. Table 6 presents the distance downstream of the center of mass of the applied dinotefuran.

Table 6 . Down s tream Movement fro m Site of Application of Dinotefuran in Flowing Water i n One Day

Flow Rate

(ft/sec) Flow Rate (mi/ hour ) Downstream

Distance (mi) Flow Rate (ft/sec) Flow Rate (mi/ hour ) Downstream Distance (mi)

0.1 0.1 3.5 1.6 2.3 56.3

0.2 0.3 7.0 1.7 2.5 59.8

0.3 0.4 10.6 1.8 2.6 63.4

0.4 0.6 14.1 1.9 2.8 66.9

0.5 0.7 17.6 2.0 2.9 70.4

0.6 0.9 21.1 2.1 3.1 73.9

0.7 1.0 24.6 2.2 3.2 77.4

0.8 1.2 28.2 2.3 3.4 81.0

0.9 1.3 31.7 2.4 3.5 84.5

1.0 1.5 35.2 2.5 3.7 88.0

1.1 1.6 38.7 2.6 3.8 91.5

1.2 1.8 42.2 2.7 4.0 95.0

1.3 1.9 45.8 2.8 4.1 98.6

1.4 2.1 49.3 2.9 4.3 102.1

1.5 2.2 52.8 3.0 4.4 105.6



### The combination of application efficiency, pesticide degradation and stream flow in Tables 4

, 5

and 6 plus runoff dilution from the areas in the watershed which are not treated are expected to

reduce the concentrations to a level substantially below that of the terrestrial crops modeled : i.e.

soil half

- life of 68 days and water half

- life of 82.7 days). Degradation for f ive ( 5 ) days by itself

will reduce the concentration to a level below the current drinking water exposure level (91.31 μg/L ) given at the beginning of this report.

### Application Amounts and Timing

Labels indicate the timing of applications and use of the higher specified rates are triggered by severe pest pressure. For m ealybug control, in the B erry and S mall F ruit crop group only, the label calls for application between budbreak and peaberry size of the fruit.

Table 7

. Proposed Application Rates for Dinotefuran in this New Use Drinking Water Assessment : IR

- 4 PR Numbers: 08645, 09832, 09550, 09548, 09514, 08596, 10727, 10728 ; Labels Dinotefuran 20SG,

Dinotefuran 70 SG and Sparkle 70 SG
Crop Maximum application rate per application (lb a.i./A) Maximum

seasonal application rate (lb a.i./A) Foliar (F)

Soil (S) Ground (G)

and/ or Aerial (A) allowed

for foliar applications

Timing (T) Berry and Small Fruit (Subgroup 13

- 07F)

Small Fruit Vine Climbing, except Fuzzy

Kiwifruit Amur River Grape Gooseberry Grape Kiwifruit, hardy Maypop Schisandra berry Cultivars, Varieties and/or hybrids of these Foliar: (0.045 to 0.135 lb ai/A) @ 14 days

interval

Or

Soil: (0.225 to 0.338 1b ai/A) @ 14 days

inter val Foliar: (0.270 lb ai/A)

Soil: ( 0.338 lb ai/A) F,S G,A

(T) For mealybug control, apply

between

budbreak and peaberry size.

Berry and Small Fruit (Subgroup 13

- 07H) Low Growing Berry Subgroup, except Strawberry Bearberry Bilberry Blueberry Lowbush Cloudberry Cranberry Lingonberry

Muntries Partridgeberry Cultivars, varieties and/or hybrids of these Foliar: (0.090 to 0.180 lb ai/A) @ 14 days

interval Foliar (0.360 lb a.i./A) F G,A

(T) For mealybug control, apply

between

budbreak and peaberry size.

Tuberous and Corm Vegetables (Subgroup 1C)

Arracacha

ArrowRoot Artichoke, Chinese Artichoke, Jerusalem Canna, edible Cassava, bitter and sweet Chayote (root)

Chufa Dasheen (taro) Ginger

Leren

Potato

Sweet Potato

Tanier

Turmeric

Yam bean
Yam, true Foliar:

0.045 to 0.068 lb ai/A @ 14 days

interval

Or

Soil:

0.293 to 0.338 lb

ai/A @ 14 days interval Foliar

0.203 lb ai/A

Or

Soil

0.338 lb ai/A F, S

Do not

combine foliar app.

with soil applications,

or vice versa. G, A

Onion, Bulb and Green (Subgroups 3

- 07A and 3

- 07B) Bulb onion, Includes: Foliar:

0.090 to 0.180 lb ai/A @ 7 days Foliar

0.270 lb ai/A F, S

Do not

combine G, ATable 7

. Proposed Application Rates for Dinotefuran in this New Use Drinking Water Assessment : IR

- 4 PR Numbers: 08645, 09832, 09550, 09548, 09514, 08596, 10727, 10728 ; Labels Dinotefuran 20SG,

Dinotefuran 70 SG and Sparkle 70 SG
Crop Maximum application rate per application (lb a.i./A) Maximum

seasonal application rate (lb a.i./A) Foliar (F)

Soil (S) Ground (G)

and/ or Aerial (A) allowed

for foliar applications

Timing (T) Daylily, bulb Fritillaria, bulb Garlic, bulb Garlic, Great

- headed, bulb Garlic, serpent, bulb Lily, bulb Onion, bulb Onion, Chinese, bulb Onion, pearl Onion, potato, bulb Shallot, bulb Cultivars, varieties and/or hybrids of these Green onion, includes: Chive, fresh leaves Chive, Chinese, fresh leaves Elegans hosta

Fritillaria leaves

Kurrat Leady's leek

Leek Leek, wild Onion, Beltsville bunching Onion, fresh Onion, green Onion, macrostem Onion, tree, tops

Oni on, Welsh, tops Shallot, fresh leaves Cultivars, varieties and/or hybrids of these interval

Or

Soil:

0.225 to 0.270 lb

ai/A @ 7 days interval Or

Soil

0.270 lb ai/A foliar app.

with soil applications,

or vice versa.

Peach and Nectarine

Peach

Nectarine Foliar:

0.090 to 0.180 lb

ai/ A @ 7 days

interval

Or

Soil:

0.225 to 0. 270 lb

ai/ A

@ 7 days interval Foliar : 0.270 lb ai/ A

Or

Soil : 0.270 lb ai/ A

O verall per

season : 0.360 lb ai/ A F, S G, A

Watercress Foliar: (0.090 to 0.180 l b Foliar:

0.360 l b ai/A) F G



### 3.3. Environmental Fate and Transport

Fate properties

Dinotefuran has a molecular weight of 202.2 g/mole, a very high water solubility (39,830 mg/L), and a low octanol/water partition coefficient (K

ow 

### = 0.283; log K

ow 

### =

- 0.549), suggesting a potential for low bioaccumulation. The low vapor pressure (1.275 x 10 - 8 

### mm Hg) and a low

### Henry ’s Law Constant (8.63 x 10 - 14 

### a tm • M 3 

### /mol) suggest th at this compound is not expected to volatilize substantially from water or soils in the environment. The p hysico

- chemical properties

of dinotefuran are listed in Table 8

.

Table 8

. Physicochemical Properties for Dinotefuran

Parameter 

### Value Reference/ Comments

Selected Physical Chemical Parameters

Chemical Classification Nitroguanidine

Pesticide Classification Systemic Insecticide Molecular Weight 202.2 g/mol MRID # 45640101 Water Solubility (20 o C) 39,830 mg/L for parent MRID# 45640112

Vapor pressure (30 o C) <1.275x10

- 8 mm Hg (equivalent to <1.7 x 10

- 6 Pa) MRID# 45640105

MRID# 45639702 Henry's Law Constant 8.63 x 10
- 14 Atm m 3 /mol Calculated
Octanol/Water Partition, K

ow 0.283 @25 o C MRID # 45639702 log K OW - 0.549 MRID # 45639702 Dissociation constant (pKa) 12.6 @20 o C (estimated) MRID # 45639702 Melting point 107.5 o C MRID # 45639702 pH 5.6 @25 o C MRID # 45654201 Density 1.40 g/cm 3 @20 o C MRID # 45639702 Solvent solubility (mg/L at 20°C) g/100 mL Solvent MRID # 45639702

Hexane 9 x 10
- 7

Heptane 1.05 x 10

- 6

Xylene 0.0072

Toluene 0.0149

Dichloromethane 6.45

Acetone 6.13

Methanol 6.00

Ethanol 2.01 Ethyl Acetate 0.52 UV/visible absorption spectrum Media Absorbance

Maximum

268 nm €

max : Molar

Absorbance

Coefficient MRID # 45639702

Acidic 1.0469 12,600

1.0180 12,300

Neutral 1.3017 12,500

1.2668 12,300

Basic 0.8869 10,700

0.9662 11,700



### Environmental fate properties for dinotefuran are shown in Table 9 . Potential route s of dissipation for dinotefuran are aqueous photolysis

, leaching, and runoff. It is stable to abiotic hydrolysis , but rapidly photodegrades in water half

- life 1.8 days. M ajor photodegradation products (>10% applied radioactivity) include 1

- methyl

- 2

- nitro

- 3

- (tetrahydro

- 3

- furylmethyl) guanidine (UF), 1

- methylguanidinium chloride (MG hydrogen chloride) , DN

- 2

- OH + DN

- 3

- OH, 3

- (Methylamino)

- 9

- oxa

- 2

- aza

- 4

- azoniabicyclone

- 3

- ene h ydrogen succinate (BCDN succinate). DN is a minor photodegradation product (<10% applied radioactivity). D inotefuran is moderately persistent in soil under both under aerobic (half

- life = 16

- 100 days) and anaerobic (half

- life = 62 days) conditions. D ino tefuran degrades to form 1

- methyl

- 2

- nitroguanidine ( MNG ), which subsequently degrades to form nitroguanidine (NG). I t is very highly mobile (K

oc 

### = 6

- 45) in soil. Because dinotefuran has low sorption coefficients in soil , it ha s a high potential to leach and runoff from the application site. T he fate of dinotefuran in aquatic

environments will depend on the type of water body . Aqueous photolysis should be important in clear and shallow bodies of water; however, in deep ponds lakes or reservoirs

, aquatic

m etabolism is expected to dominate the dissipation processes. Dinotefuran was moderately persistent under actual use conditions in CA, NY, and GA field studies. The major degradation

### product was identified as MNG. Although there was no detection of dinotef uran in deep soil samples, MNG was detected in 15 to 30 cm soil layers in the GA field dissipation study.

Table 9

. Environmental Fate Properties for Dinotefuran

Parameter Value Reference/ Comments

Hydrolysis Half

- life stable MRID# 45640102 (s ) MRID# 45640102 (a )

Photo degradation in W ater Half

- life 1.8 days MRID# 45640105 (s)

Photo degradation in Soil Half

- life Stable MRID# 45640109 (u)

Aerobic Soil M etabolism Half

- life 38 days , Loamy Sand Soil 17 days, Loam Soil 78 days, Loam soil 89 days, Loamy Sand soil 63 days, Loamy Sand soil 100 days, Loamy Sand soil 87.7 days , Loamy Sand s oil 15.9 days

, Silt Loam soil MRID# 45640111 (s)

M RID# 45640112 (s) MRID#’s 46751101(a) MRID#45640112(a)

MRID# 46711201 (s)

Anaerobic Soil M etabolism Half

- life 65 days MRID# 45891616 (s)

Aerobic Aquatic metabolism Half

- life 79.3 days

76 .0 days MRID # 45640117 (s)

Anaerobic Aquatic metabolism Half

- life Entire system: 65.0 days Water: 51.0 days Soil: 62.0 days MRID# 45891616 (s)

Batch Equilibrium Texture Kd Koc

L oam 1.01 42 Sandy Loam 0.71 45

C lay L oam 1.22 42

L oamy S and 0.12 6
Si lt L oam 0.22 22 MRID# 45640114 (a)

Terrestrial Field Dissipation CA (SL) t 1/2 = 65.2 days MNG (degradate) was detected in 0

- 15 cm soil at 31.5% @ 45 days after 2nd application.

GA (SL) t 1/2 = 19.4 days

MNG was detected in 0

- 15 cm soil at

5.3% max. mean concentration after 7 and 30 days after the 2 nd
application.

NY (SL) t 1/2 = 55.9 days

MNG was detected in 0

- 15 cm soil at 6.6% @ 45 and 120 days after the second application. Applied 2X @ 0.268 lb a.i/A @ 14

- day interval to bare soil. MRID# 45640118 (a)

Accumulation in Fish, max. BCF NA Waived (K OW = 0.28) * (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study (u)=unacceptable ; NA=Not Available; N/A=Not Applicable



### The degradation products of dinotefuran are shown in Table 10

. MNG, is the major degradation product in soil. DN, UF, MG hydrogen chloride, DN

- 2

- OH+DN

- 3

- OH, and BCDN succinate are major degradation products in aquatic environments. These degradation products are formed through metabolism ( i

. e

. , DN) or photodegradation ( i

. e. , DN, UF, MG hydrogen chloride, DN

- 2

- OH+DN

- 3

- OH, and BCDN).

### MNG contains the nitro guanidine structure and therefore is considered to possess similar toxicity as the parent. DN is also s tructurally similar to the parent and therefore is considered to

exhibit similar toxicity as the parent. Given the structures of the remaining degradates, they are expected to be less toxic than the parent ( MARC memo USEPA 2004, D293759 ).

Table 10 . Dinotefuran Degradates Identified in Environmental Fate Studies

Short

names Structure Study Name Results (calculated or observed half

life, degradates, and quantities, in % applied)

MNG Aerobic Soil Metabolism Maximum 23.96% at 42 days (preliminary study) Maximum 13.7% at 225 days (conducted on radiolabeled parent), study termination

Terrestrial Field Dissipation Maximum 31.5% at 45 days after 2 nd
application; study termination at 170 days after 2 nd application

DN Anaerobic Soil Metabolism Maximum 29.2% at 120 days in

Switzerland soil

Aerobic Aquatic Metabolism Maximum 23.1% at 180 days in river system and 32.6% at 103 days in pond

system

Photolysis in Water Maximum 7.5% at 11 days

UF Photolysis in Water Maximum 10.6% at 13.8 days (last test interval)

MG hydrogen

chloride Photolysis in Water Maximum 10.2% at 1.8 days, and 0.8% at 13.8 days (final sampling interval)

DN

- 2

- OH

+ DN

- 3

- OH 1 Photolysis in Water Maximum 28.2% at 13.8 days (study termination)

BCDN

Succinate Photolysis in Water Maximum 16.1% at 1.8 days and 4.5% at 13.8 days (study termination)



### Environmental fate properties for MGN are shown in Table 1 1 . Potential routes of dissipation include photodegradation , leaching, and runoff. M GN is stable to abiotic hydrolysis at pH 4, 7, and 9. It rapidly photodegrades (t 1/2 

### = 2.4 days) in water. MGN is moderately persistent (t 1/2 

### = 66.9 to 166 days) in soil and persistent (t 1/2 

### = 459 days) in aquatic environments. It has low soil:water portioning coefficients (K d 

### < 1; K

oc 

### <31), suggesting a potential for leaching and runoff. Field dissipation studies showed MGN residue detections in the 15

- 30 cm soil layer in a GA field study. These data suggest a leaching potential u nder actual use conditions.

Table 1 1

. Physicochemical and Environmental Fate Properties for Dinotefuran Degradation Product

- MGN

Parameter 

### Value Reference/ Comments N H N H 2

N C H 3

N O 2

O N H

N H N H

C H 3

H 3 P O 4

O N H

O N H

C H 3

N H N H N H 2 C H 3

Cl H

O H N NH

HN OH COOH

COOH
2

N H N O

N H
C H 3 C O O H

C O O H

### Table 1 1

. Physicochemical and Environmental Fate Properties for Dinotefuran Degradation Product

- MGN

Parameter 

### Value Reference/ Comments

Selected Physical Chemical Parameters Water Solubility (20 o C) 11,480 mg/L MRID# 45640112
MRID# 45639702, 45639706, 45639707 (USEPA Pesticide Fact Sheet, 2004)

Hydrolysis Half

- life pH 4

- 9 (50 o C) stable MRID# 45640103 (s)

Photodegradation in Water Half

- life 2.4 days MRID# 45640107 (s)

Aerobic Soil metabolism Half

- life 66.9 days in Silt Loam soil 166 days in Sandy Loam soil 72.5 days in Clay Loam soil MRID# 46711202 (s)

Aerobic Aquatic metabolism t 1/2 459.3 days MRID # 45640117 (USEPA Pesticide Fact Sheet, 2004) Mobility in Soils Texture K d K OC L oam 0.75 31

S andy L oam 0.12 8

C lay L oam 0.70 24

L oamy S and 0.16 8

Si lt loam 0.16 16 MRID# 45640116 (s)

* (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study; (u) = unacceptable study; NA=Not Available; N/A=Not Applicable



### Environmental fate properties for DN

- phosphate 1 

### are shown in Table 1 2 . Potential routes of dissipation include photodegradation, microbial

- mediated metabolism, leaching, and runoff. N

phosphate is stable to abiotic hydrolysis at pH 4, 7, and 9). Photodegradation is slow (t 1/2 

### = 53.4 to stable days) in water at pH 5, 7, and 9. It is moderately persistent (t 1/2 

### = 114 days) in soil and aquatic environments. DN

- phosphate has low soil:water portioning coefficients (K d 

### < 3; Koc

58

- 413) in loam and sandy loam textured soils. Higher soil:water partitioning coefficients (K d 

### : 7

- 72; K

oc 

### : 270

- 2502) were found in clay textured soils. These data suggest the extent leaching or

runoff of DN

- phosphate is dependent on soil properties such as texture and organic carbon

content.

Table 1 2

. Physicochemical and Environmental Fate Properties for Dinotefuran Degradation Product DN

- Phosphate

Parameter 

### Value Reference/ Comments

Selected Physical Chemical Parameters

1 DN phosphate (1

- methyl

- 3

- (tetrahydro

- 3

- furylmethyl)guanidinium dihydrogen phosphate) was identified as a degradation product of dinotefuran in photodegradation in soil (MRID 45640109), photodegradation in water (MRID 45640106, 45640105) and anaerobic soil metabolism (MRID 45891616) studies. Although the phosphorus is not an elemental constituent of parent dinotefuran, DN phosphate was formed as a salt of orthophosphate and 1

- methyl

- 3

- (tetrahydro

- 3

- furylmethyl)guanidinium. Because the DN phosphate salt will dissociate in soil and aquatic environments to form (1

- methyl

- 3

- (tetrahydro

- 3

- furylmethyl)guanidinium) and phosphoric acid, it is not expected to alter the environmental fate or toxicity of the organic moiety of DN phosphate (1

- methyl

- 3

- (tetrahydro

- 3

- fury lmethyl)guanidinium).

### Table 1 2

. Physicochemical and Environmental Fate Properties for Dinotefuran Degradation Product DN

- Phosphate

Parameter 

### Value Reference/ Comments

Water Solubility (20 o C) 619,400 mg/L MRID# 45640112

MRID# 45639702, 45639706, 45639707 (USEPA Pesticide Fact Sheet, 2004)

Hydrolysis Half

- life

DN

- Phosphate pH 4

- 9 (50 o C) stable MRID# 45640104 (s)

Photodegradation in Water Half

- life pH 5 pH7 pH9 53.4 days Stable (533.2 days)

Stable MRID# 45640108 (s)

Aerobic Soil Metabolism Half

- life

DN 114 days MRID# 45640117 (USEPA Pesticide Fact Sheet, 2004) Aerobic Aquatic metabolism t 1/2 114 days MRID# 45640117 (USEPA Pesticide Fact Sheet, 2004) Mobility in Soils

DN

- Phosphate Texture K d K OC L oam 2.08 87

S andy L oam 2.07 58

C lay L oam 72.54 2502

S andy L oam 2.93 413

C lay 7.11 270 MRID# 45640113 (s)

* (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study; (u) = unacceptable study; NA=Not Available; N/A=Not Applicable



### Environmental fate properties for UF are shown in Table 1 3 . The potential route of dissipation

is microbial

- mediated metabolism. UF is stable to abiotic hydrolysis and photodegradation. It is moderately persistent in (t 1/2 

### = 60 days) in soil.

Table 1 3

. Physicochemical and Environmental Fate Properties for Dinotefuran Degradation Product UF

Parameter 

### Value Reference/ Comments

Selected Physical Chemical Parameters Water Solubility (20 o C) 4,171 mg/L for UF MRID# 45640112 MRID# 45639702, 45639706, 45639707 (USEPA Pesticide Fact Sheet, 2004)

Hydrolysis Half

- life

UF Stable MRID# 45640102 (USEPA Pesticide Fact Sheet, 2004) Photodegradation in Water Stable (~500 days) MRID# 45640105 (USEPA Pesticide Fact Sheet, 2004)

Aerobic Soil Metabolism Half

- life 60 days (at mean) MRID# 45640111 (USEPA Pesticide Fact Sheet, 2004) * (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study; (u) = unacceptable study; NA=Not Available; N/A=Not Applicable USEPA 2004. Dinotefuran. Report of the Metabolism Assessment Review Committee. Office of Prevention, Pesticides, and Toxic Substances. OPP/EFED. Washington, DC. January 20, 2004. TXR No. 0052304. DP Barcode

D293759.

### Figure 1. Dinotefuran and di n otefuran degradates (MTI

- 466)

### Appendix 1

.

Background information on FIRST and SCIGROW models and output files.

Background Information on FIRST model:

FIRST (FQPA Index Reservoir Screening Tool) is a screening model designed to estimate the pesticide concentrations found in surface water for use in drinking water assessments. It provides high

- end values on the concentrations that might be found in a small drinking water reservoir due to the use of pesticide. Like GENEEC, the model previously used for Tier I screening level, FIRST is a single

- event model (one run

- off event), but can account for spray drift from multiple applications. FIRS T takes into consideration the so called Index Drinking Water Reservoir by representing a larger field and pond than the standard GENEEC scenario. The FIRST scenario includes a 427 acres field immediately adjacent to a 13 acres reservoir, 9 feet deep, wit h continuous flow (two turnovers per year). The pond receives a spray drift event from each application plus one runoff event. The runoff event moves a maximum of 8% of the applied pesticide into the reservoir. This amount can be reduced due to degradat ion on field and the effect of binding to soil. Spray drift is equal to 6.4% of the applied concentration from the ground spray application and 16% for aerial applications.

FIRST also makes adjustments for the percent crop area. While FIRST assumes that the entire watershed would not be treated, the use of a PCA is still a screen because it represents the highest percentage of crop cover of any large watershed in the US, and it assumes that the entire crop is being treated. Various other conservative ass umptions of FIRST include the use of a small drinking water reservoir surrounded by a runoff

- prone watershed, the use of the maximum use rate, no buffer zone, and a single large rainfall.

FIRST Model

RUN No.1 FOR Dinotefuran ON Crops Group s 1C & 13

- 07 * INPUT VALUES *

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

RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

------------- ------------------------------------------------------- .338( .338) 1 1 30.1 39830.0 AERIAL(16.0) 100.0 .0

FIELD AND RESERVOIR HALFLIFE VALUES (DAYS)

--------------------------------------------------------------------
METABOL IC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

(FIELD) RAIN/RUNOFF (RESERVOIR) (RES.

- EFF) (RESER.) (RESER.)

-------------------------------------------------------------------- 68.00 2 N/A 1.80

- 223. 20 82.70 60.34

UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.1.0 JAN 1, 2007

-------------------------------------------------------------------- PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC)

CONCENTRATION CONCENTRATION

-------------------------------------------------------------------- 33.384 5.487RUN No. 2 FOR Dinotefuran ON Turf Grass * INPUT VALUES *

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

RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

------------------------------------- ------------------------------- .504( .504) 1 1 30.1 39830.0 AERIAL(16.0) 100.0 .0

FIELD AND RESERVOIR HALFLIFE VALUES (DAYS)

--------------------------------------------------------------------
METABOLIC DAYS UNTIL HYDROLYS IS PHOTOLYSIS METABOLIC COMBINED

(FIELD) RAIN/RUNOFF (RESERVOIR) (RES.

- EFF) (RESER.) (RESER.)

-------------------------------------------------------------------- 68.00 2 N/A 1.80

- 223.20 82.70 60.34

UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.1.0 JAN 1, 2007

-------------------------------------------------------------------- PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC)

CONCENTRATION CONCENTRATION

-------------------------------------------------------------------- 49.780 8.181



### Background Information on SCIGROW model:

SCIGROW (Screening Concentration in Ground Water) provides a groundwater scre ening exposure value to be used in determining the potential risk to human health from drinking water contaminated with the pesticide. Since the SCIGROW concentrations are likely to be approached in only a very small percentage of drinking water sources, i.e., highly vulnerable aquifers, it is not appropriate to use SCIGROW for national or regional exposure estimates.

SCIGROW estimates likely groundwater concentrations if the pesticide is used at the maximum allowable rate in areas where groundwater is ex ceptionally vulnerable to contamination. In most cases, a large majority of the use area will have groundwater that is less vulnerable to

contamination than the areas used to derive the SCIGROW estimate.

Values below 0.006 ppb (6 ng/L) obtained by SCIGRO W2.3 are beyond the scope of the regression data and have not been verified. If concerns are raised by exposures of less than 0.006 ppb, a higher

- tier ground water exposure assessment should be considered, regardless of how low a screening concentration i s returned by SCIGROW.

SCIGROW

VERSION 2.3

ENVIRONMENTAL FATE AND EFFECTS DIVISION

OFFICE OF PESTICIDE PROGRAMS

U.S. ENVIRONMENTAL PROTECTION AGENCY

SCREENING MODEL

FOR AQUATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical:Dinotefuran
crop: pome and stone fruit

time is 5/20/2011 9: 9: 5

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

Application Number of Total Use Koc Soil Aerobic
rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)------------------------------------------------------------------------ 0.304 2.0 0.608 6.00E+00 38.0

------------------------------------------------------------------------ groundwater screening cond (ppb) = 1.92E+00

************************************************************************

SciGrow version 2.3

chemical:Dinotefuran
crop: pome & stone fruits

time is 5/2 3 /2011 12:51 : 12

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

Application Number of Total Use Koc Soil Aerobic

rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------ 0.302 2.0 0.604 6.00E+00 38.0

---------------------------------------------- -------------------------- groundwater screening cond (ppb) = 1.91E+00

************************************************************************

SCIGROW

VERSION 2.3

ENVIRONMENTAL FA TE AND EFFECTS DIVISION

OFFICE OF PESTICIDE PROGRAMS

U.S. ENVIRONMENTAL PROTECTION AGENCY

SCREENING MODEL

FOR AQUATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical:Dinotefuran

cro p: Tuberous & Corm Vegetables time is 11/26/2011 11:06:08

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

Application Number of Total Use Koc Soil Aerobic

rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------ 0.338 1.0 0.338 6.00E+00 38.0

---------------------------------------------- -------------------------- groundwat er screening cond (ppb) = 1.07 E+00

************************************************************************



### EFED / OPP Tier I Rice Model

The EFED/OPP Tier I Rice Model version 1.0 relies on an equilibrium partiti oning concept to provide conservative estimates of environmental concentrations resulting from application of pesticides to rice paddies. W hen a pesticide is applied to a rice paddy, the model assumes that it will instantaneously partition between a water phase and a sediment phase. The single, screening

- level concentration calculated with this model represents both short and long term surface water exposure and can be used for both aquatic ecological risk assessments and drinking

water exposure assessmen ts for human health risk assessment. The formula of the Tier I Rice

Model v1.0 is as follows:

d ai

w 

### K m C 00013

. 0 00105

. 0 '

+ =



### and, if appropriate:

oc d 

### K K 01

. 0 =

where :

### C

w 

### = water concentration [ μg/L ]

m ai 

### ' = mass applied per unit area [kg/ha]

K d 

### = water

- sediment partitioning coefficient [L / k g]

K
oc 

### = organic carbon partitioning coefficient [L/kg]

Note that neither the degradation of the pesticide nor the mass transfer from the aqueous phase to the sediment is considered in this conceptualization, which greatly simplifies the model. The

absence of degradation adds conservatism to the model ( i.e. , es timated concentrations should be higher than those usually found in rice paddies). The absence of mass transfer processes can either add or reduce conservatism depending on numerous conditions such as whether the pesticide is soil or water applied and whet her actual degradation occurs preferentially in the sediment or the water compartment; however, consideration of this parameter is a refinement beyond a Tier I conceptualization.

Physical Values of the Tier I Rice Model v1.0.

Parameter Symbol Value Reference

Water column d epth d

w 

### 0.10 m USDA (1998, 2002)

Sediment d epth d sed 

### 0.01 m Calibration described in Section III C of this

document.

Organic content of

sediment f

oc 

### 0.0 1 Justification provided in Section III B of this

document.

Sediment bulk density ρ b 

### 1300 kg/m 3 

### Brady (1984), Hillel (1982)

Grain density ρ g 

### 2650 kg/m 3 

### Density of quartz, typical assumption; Brady(1984), Hillel (1982)

Sediment porosity θ sed 

### 0.509 θ sed = 

### 1

- (ρ b 

### /ρ g 

### )

Most of the assumptions used in this model help ensure that the outputs are protective of most environments associated with rice agriculture. The model assumptions include the following:

1. Movement of pesticide on suspended sediment is not considered. 2. Degradation does not occur.

3. Volatilization and other dissipation processes are not considered. 4. Partitioning to sediment is instantaneous. 5. Water is available for human or wildlife exposure instantaneously. 6. Water column depth is 10 cm. 7. Sediment depth is 1 cm. 8. All pore space is saturated wi th water. 9. Organic carbon fraction is 0.01. 10. Bulk density is 1300 kg/m 3



### . 11. Grain density is 2650 kg/m 3



### .

### Appendix 2.

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

OFFICE OF PREVENTION, PESTICIDES AND
TOXIC SUBSTANC ES

January 23, 2009

PC Code: 044312

DP Bar Code: D 357111 

### MEMORANDUM

SUBJECT: Tier I Estimated Drinking Water Concentrations of Dinotefuran and i ts

T ransformation P roducts of C oncern MNG, DN, UF and DN

- 2

- OH + DN

- 3

- OH,

for U se in Human Health Risk Assessment , Proposed New (IR

- 4) Use of the

Chemical on Leafy Brassica Greens and Turnip Greens

TO: Sidney Jackson, Risk Manager Reviewer Daniel Rosenblatt, Chief Risk Integration, Minor Use and Emergency Response Branch Registration Division (7505P)

and Barry O’Keefe , Biologist Paula Deschamp, Branch Chief Registration Action Branch III Health Effects Division (7509P)

FROM : José Luis Meléndez, Chemist

Environmental Risk Branch V Environmental Fate and Effects Division (7507P)

THROUGH: Mah Shamim, Ph .D., Chief

Environmental Risk Branch V

### Environmental Fate and Effects Division (7507P)

The purpose of this memorandum is to provide the Estimated Drinking Water s Concentrations (EDWCs) of dinotefuran, an active ingredient of products such as SafariTM 20SG Insecticide and DINOTEFURAN 20SG Insecticide, and its transformation products MNG, DN, UF, and DN

- 2

- OH + DN

- 3

- OH (for nomenclature and structures of these compounds, please, refer to Appendix

B ), due to the use of the chemical on various crops

, turf and or namentals , using soil, ground or aerial applications. EFED has reviewed the IR

- 4 petition, and found that the use with the highest rate per application and per season is still turf . Therefore, the EFED will rely on its January 21,

2004 Tier I Drinking Wat er Analysis, wi th electronic copy a ttached to this document (Appendix C) . Please, find below the Executive Summary and a table indicating the proposed EDWCs to be used. Should additional refinements are required by HED, please, contact us, so that the EFED may schedule tier 2 surface waters PRZM/EXAMS modeling. Should any questions arise, please, contact us.

EXECUTIVE SUMMARY

Table 1 provides a summary of the Tier I modeled drinking water s concentrations. Please, refer to Appendix C for original me morandum.

Table 1. Tier I Estimated Drinking Water Concentrations

Chemical Acute (peak) Surface Water Concentration (ppb) Annual Average Surface Water Concentration (ppb) Ground Water Concentration (ppb)

Dinotefuran 48.20 8.00 2.75

MNG 3.86 1.63 0.86

DN 7.77 3.32 0.19

UF 4.07 2.07 0.32

DN

- 2

- OH 1 11.88 5.95 0.94

1

- DN

- 2

- OH represents DN

- 2

- OH+DN

- 3

- OH. These two were reported jointly in the study.



### Dinotefuran, [CAS name N

- methyl

- N ′

- nitro

- N ′′

- [(tetrahydro

- 3

- furanyl)methyl]guanidine; IUPAC name ( EZ )

- ( RS )

- 1

- methyl

- 2

- nitro

- 3

- (tetrahydro

- 3

- furylmethyl)guanidine ], is a nitroguanidine

insecticide. It s PC code is 044312 and it s CAS number is 165252

- 70

- 0 . Dinotefuran belongs to a broad group of ins ecticides commonly known as nicotinoid insecticides. Within the nicotinoid insecticides, dinotefuran belongs to the narrower class of insecticides known as nitroguanidine (also includes clothianidin, imidacloprid and thiamethoxan), they are nicotinic acet ylcholine receptor agonists/ antagonists, group 4A insecticide s ( www.irac

- online.org ). These compounds target the nicotinic acetylcholine receptors (nAChR) site and activate post

- synaptic acetylcholine receptors. D inotefuran, like other neonicotinoids, acts as an agonist of acetylcholine, the neurotransmitter that stimulates the nAChR. Acetylcholine (ACh) is the endogenous agonist and excitatory neurotransmitter of the cholinergic nervous system. Neurotransmission through the nicotinic cholinergic synapse is mediated in two steps. First, ACh is released from the presynaptic membrane by exocytosis and interacts with the binding site located at the extracellular domain of the nAChR/ion channel complex. Second, a for mational change of the receptor molecule leads to opening the ion channel, promoting the influx of extracellular Na + 

### and

efflux on intracellular K + 

### to disrupt the equilibrium status of the membrane potential. (Please, refer also to original S3 New Chemica l review dated June 30, 2004.)

### Currently, dinotefuran is used in various crops such as cotton, head and stem brassica ( broccoli, cabbage, cauliflower )

, cucurbits ( watermelon, cucumber )

, fruiting vegetables ( pepper, tomato )

, grapes, leafy vegetables ( lettu ce ) and potato ; it is used also on ornamental plants and turf.

H owever, the maximum application rate is on turf.

This action is an Interregional Project No. 4, for the proposed use of dinotefuran on leafy brassica greens (Subgroup 5B), including turnip g reens (b roccoli raab, Chinese c abbage (Bok Choy), c ollards, k ale, m izuna, m ustard g reens, m ustard s pinach, r ape g reens and t urnip g reens)

. Please, refer to Appendix A for a summary of the use information gathered from the current and proposed label s

.

This is a Tier I screening

- level Drinking Water s Assessment (DWA). For surface waters the tier

1 aquatic model FIRST was used, and for ground waters, the tier 1 aquatic model SCI

- GROW was utilized. For the assessment, maximum application rates and minimu m intervals between applications were used (note: for turf a single application was assumed). The Metabolism Assessment Review Committee’s (MARC) decision document concluded that the transformation products MNG, DN, UF, and DN

- 2

- OH + DN

- 3

- OH of dinotefura n are of potential concern for drinking water sources. Therefore, EDWCs of these compounds were also simulated using

FIRST and SCI

- GROW models as explained in the memorandum attached. The approach used to calculate the transformation products was the ind ividual degradate calculation, as opposed to

the total residues calculations.

The major data gaps are related to the transformation products MNG, DN, UF, and DN

- 2

- OH +

DN

- 3

- OH; modeling was used to obtain some of the parameters needed for the estimation of the drinking water concentrations of the above mentioned degradates, using EPIWIN.

### Appendix A. Current and Proposed Application Rates for Dinotefuran

Table A1. Current and Proposed Application Rates for D inotefuran (data obtained from current an d proposed labels for DINOTEFURAN 20SG, EPA Reg. No. 33657

- 17, STARKLE 70SG, EPA Reg. No. 33657

- 38, DINOTEFURAN 70SG, EPA Reg. No. 59639

- 135 and DINOTEFURAN 20%, EPA Reg. No. 33657

- 16). New use appears shaded yellow and bolded.
Crop Maximum application rate per application (lb a.i./A) Maximum

seasonal application rate (lb a.i./A) Foliar or Soil application

allowed? Ground or Aerial

allowed for foliar applications?

Leafy Brassica Greens: Broccoli Raab, Chinese Cabbage (Bok Choy), Collards, Kale, Mizuna, Mustard Greens, Mustard Spinach, Rape Greens, Turnip Greens 0.141 @ 7 days

interval 0.268 F

No more than 3 applications

per season are allowed. G, A

Cotton 0.134 @ 7 days interval 0.268 F G, A

Head and Stem Brassica: Broccoli, Brussels sprouts, Cabbage, Cauliflower, Cavalo Broccolo, Chinese broccoli, Chinese cabbage, Chinese mustard cabbage, Kohlrabi Foliar: 0.179 @ 7 days

interval

Or

Soil: 0.33 0.268 Foliar

Or

0.536 Soil F, S

Do not combine foliar app. with soil applications

, or vice versa

. G, A

Cucurbits: Balsam pear (bitter melon), Calabaza, Chayote (fruit), Chinese okra, Chinese waxgourd, Citron melon, Cucumber, Gherkin, Gourds, Edible

melons including hybrids (including cantaloupe, casaba, Chinese preserving melon, Crenshaw, honeydew melons, honey balls, mango melon, muskmelon, Persian melon, winter melon), Pumpkin, Squash (including summer, winter acorn, spaghetti), Watermelon including hybri ds Foliar: 0.179 @ 7 days

interval

Or

Soil: 0.33 0.268 Foliar

Or

0.536 Soil F, S

Do not combine foliar app. with soil applications

, or vice versa

. G, A

Fruiting Vegetables: Eggplant, Ground Cherry, Pepinos, Pepper (including bell peppers, chili peppers, cooking peppers, pimentos and sweet peppers), Tomatillo, Tomato (do not apply to

varieties of tomatoes which are less than 2 inches in size, such as cherry and grape tomatoes) Foliar: 0.179 @ 7 days

interval

Or

Soil: 0.33 0.268 Foliar

Or

0.536 Soil F, S

Do not combine foliar app. with soil applications

, or vice versa

. G, A

Grapes Foliar: 0.132 @ 14 days interval

Soil: 0.33 0.264 Foliar

0.33 Ground

0.528 overall

per season F, S Make only one soil application. G w. airblast , A

Leafy Vegetables (Except Brassica Vegetables): includes: Amaranth, Arugula, Cardoon, Celery, Chinese Celery, Celtuce, chervil, Edible

- leaved & Garland Chrysanthemum, Corn Salad, Garden & Upland Cress, Dandelion, Dock, Endive, Florence Fennel, Head & Leaf L ettuce, Orach, Parsley, Garden & Winter Purslane, Radichio, Rhubarb, Spinach, New Zealand & Vine Spinach, Swiss Chard Foliar: 0.134 @ 7 days

interval

Or

Soil: 0.33 0.268 Foliar

Or

0.536 Soil F, S

Do not combine foliar app. with soil applications

,

or vice versa

. G, A

Potato Foliar: 0.066 @ 14 days interval 0.198 Foliar F, S

Do not combine foliar app. with G w. airblast , ATable A1. Current and Proposed Application Rates for D inotefuran (data obtained from current an d proposed labels for DINOTEFURAN 20SG, EPA Reg. No. 33657

- 17, STARKLE 70SG, EPA Reg. No. 33657

- 38, DINOTEFURAN 70SG, EPA Reg. No. 59639

- 135 and DINOTEFURAN 20%, EPA Reg. No. 33657

- 16). New use appears shaded yellow and bolded.
Crop Maximum application rate per application (lb a.i./A) Maximum

seasonal application rate (lb a.i./A) Foliar or Soil application

allowed? Ground or Aerial

allowed for foliar applications?

Or

Soil: 0.33 Or

0.33 Soil soil applications

, or vice versa

.

Turfgrass (commercial, residential, recreational) Foliar

0.54 0.54 F G

Vegetable Transplants grown in enclosed structures, including Cucurbits, Fruiting Vegetables, Head and Stem Brassica and Leafy Vegetables (excluding Brassica spp.) Foliar

0.18 0. 268 F or Broadcast

spray G

O rnamental plants in greenhouses

, nurseries , interior plantscapes, lath and shadehouses and outdoor landscapes (commercial, industrial, recreational and residential) or O rnamental containerized or in ground plants (including Shrubs, Bedding Plants, Flowering Plants, Foliage Plants,

Ground Covers, Evergreens, Ornamental Plants and Trees, Non

Bearing Fruit Trees, Non

- Bearing Nut

Trees and Non

- Bearing Vines) Foliar

0.2

Soil

12

- 24 oz per gallon 0.54

0.54 F w. airblast (for trees and vines)

or Broadcast spray, S

Do not make

more than one soil application per crop cycle or three months,

whichever is

shorter. G

### Appendix B. Nomenclature and Structures of Dinotefuran and its Transformation

Products

Table B1. Nomenclature of Dinotefuran and its Transformation Products

Applicant's Code IUPAC Chemical CAS Name CAS No. PC

Code

Dinotefuran/MTI

- 446 (RS)

- 1

- methyl

- 2

- nitro

- 3

- (tetrahydro

- 3

- furylmethy l) guanidine N

- methyl

- N’

- nitro

- N”

- [(tertrahydro

- 3

- furanyl) methyl]guanidine. 165252

- 70

- 0 044312

DN

- Phosphate 1

- Methyl

- 3

- (tetrahydro

- 3

- furylmethyl) guanidinium dihydrogen phosphate - - -

MNG 1

- Methyl

- 2

- nitroguanidine N

- methyl

- N’

- nitro

- guanidine 4245

- 76

- 5

-

UF 1

- methyl

- 3

- (tetrahydro

- 3

- furylmethyl)urea

- - -

DN

- 2

- OH + DN

- 3

- OH Bis[1

- (3

- hydroxytetrahydro

- 3

- furylmethyl)

- 3

- methylguanidinium] terephthalate (DN

- 3

- OH) - - -



## Dinotefuran [MTI

**- 446]** 

**– Parent Compound** 

IUPAC Name: ( EZ )

- ( RS )

- 1

- Methyl

- 2

- nitro

- 3

- (tetrahydro

- 3

- furylmethyl)guanidine.

CAS Name: N

- Methyl

- N ′

- nitro

- N ′′

- [(tetrahydro

- 3

- furanyl)methyl]guanidine.

CAS Number: 165252

- 70

- 0.
SMILES String: CNC(=NN(=O)=O)NCC1COCC1 (ISIS v2.3/Universal SMILES).

No EPI Suite, v3.12 SMILES String found as of 9/29/06.



## Unlabeled

O C H 2 

### N H C

N N H

N O 2 

### C H 3

## 1

**- Methyl** 

**- 2** 

**- nitroguanidine**  **[N**

**- Methyl** 

**- N’** 

**- nitro** 

**- guanidine; MNG]** 

IUPAC Name: 1

- Methyl

- 2

- nitroguanidine.

CAS Name: N

- methyl

- N’

- nitro

- guanidine.

CAS Number: 4245

- 76

- 5.
SMILES String: NC(=NN(=O)=O)NC (ISIS v2.3/Universal SMILES). N(=O)(=O)NC(=N)NC EPI Suite, v3.12 SMILES String found as of

07/02/08.



## 1

**- Methyl** 

**- 3** 

**- (tetrahydro** 

**- 3** 

**- furylmethyl)urea [UF]** 

IUPAC Name: 1

- Methyl

- 3

- (tetrahydro

- 3

- furylmethyl)urea.

CAS Name: Not reported.

CAS Number: Not reported. N H N H 2



### N C H 3



### N O 2

O N H

O N H

C H 3

## 1

**- Methyl** 

**- 3** 

**- (tetrahydro** 

**- 3** 

**- furylmethyl)guanidinium dihydrogen**  **phosphate [DN phosphate] (a salt of DN)**

IUPAC Name: Not reported.

CAS Name: Not reported.

CAS Number: Not reported.



## Bis[1

**- (3** 

**- hydroxytetrahydro** 

**- 3** 

**- furylmethyl)** 

**- 3** 

**- methylguanidinium]**  **terephthalate**

**DN**

**- 3** 

**- OH** 

IUPAC Name: Bis[1

- (3

- hydroxytetrahydro

- 3

- furylmethyl)

- 3

- methylguanidinium] terephthalate.

CAS Name: Not reported.

CAS Number: Not reported. O N H

N H N H

C H 3



### H 3 

### P O 4O H N NH

HN OH COOH

COOH


### 2

### Appendix C

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

OFFICE OF PREVENTION, PESTICIDES AND

TOXIC SUBSTANCES



### January 21, 2004

MEMORANDUM

PC Code: 044312

DP Bar Code: D290192

SUBJECT: Tier I Estimated Drinking Water Concentrations of Dinotefuran (MTI

- 446) and its major transformation products for use in Huma n Health Risk Assessment

TO: Meredith Laws, Branch Chief Rita Kumar, PM Team Reviewer

Insecticide

- Rodenticide Branch Registration Division (7505C)

and Kathy Raffael, Risk Assessor Health Effects Division (7509C)

FROM : Subijoy Dutta, P.E., Environmental Engineer

Environmental Risk Branch V Environmental Fate and Effects Division (7507C)

THROUGH: Mah Shamim, Ph.D., Chief

Environmental Risk Branch V Environmental Fate and Effects Division (7507C)

This memo presents the Tier I Estimated Drinking Water Co ncentrations (EDWCs) for dinotefuran (MTI

- 446), and for its major transformation products

- MNG, DN, UF, and DN

- 2

- OH +DN

- 3

- OH. These estimates are based upon calculations using FIRST (surface water) and SCIGROW (ground water) for use in the human health r isk assessment. The Mitsui Chemical, Inc. is seeking registration for the new uses of the chemical on Leafy Vegetables, Turf Grasses, and Residential uses such as fly bait, ant bait, and house and garden ready to use spray.

### Page 29 Table 1. Tier I Estimated Drinking Water Concentrations

Chemical Acute (peak) Surface Water Concentration (ppb) Annual Average Surface Water Concentration (ppb) Ground Water Concentration (ppb)

Dinotefuran (MTI

- 446) 48.20 8.00 2.75

MNG 3.86 1.63 0.86

DN 7.77 3.32 0.19

UF 4.07 2.07 0.32

DN

- 2

- OH 1 11.88 5.95 0.94

1

- DN

- 2

- OH represents DN

- 2

- OH+DN

- 3

- OH. These were reported jointly as one metabolite in MRID 45640105

.



### The above values (Table 1) generally represent upper

- bound estimates of the concentrations that might be found in surface water and groundwater due to the use of dinotefuran on Turfgrass, which represents the maximum application rate and worst case scenari o. Both the surface and ground water models provide screening level estimates. Most of the physical properties of UF,

and DN

- 2

- OH were estimated by using the EPI win program. For lack of pertinent data, the biodegradation half life was also estimated by using the Biowin program for UF and DN

- 2

- OH. It should be noted that the models used for the estimation of drinking water concentrations

assumed the formation of UF and DN

- 2

- OH. These degradates are photolysates and it appears that they are less likely t o be formed in the ground spray scenario for turfgrass. Most of the formation of these degradates would be caused by direct exposure of surface waters to the parent by spray drift, followed by photolysis. EFED emphasizes that this is only a screening lev el analyses (Tier 1), and should there be a need by HED, additional refinements can be made if the registrant provides further studies addressing the degradate characteristics which should yield accurate input values for the models.

Background Informatio n About Dinotefuran, and Use on Leafy Vegetables, Turf grasses,

and Residential use :



### Dinotefuran is a selective systemic insecticide which is also known as MTI

- 446. The registrant, Mitsui Chemicals America, Inc. is presently proposing uses on leafy veget ables, turf grasses and various residential uses such as ant bait, fly bait, house and garden ready

- to

- use

- spray, total release fogger, cat spot

- on, 20% PCOs for pet sleeping areas, and Shuriken cockroach gel bait.

The principal mode of action of dinotefu ran relates to its neonicotinoid and nitroiguadine subclass. From the label information it is evident that dinotefuran is toxic to bees exposed to direct treatment or to residue on blooming crops and weeds. Also, following an in

- furrow or soil applicatio n of dinotefuran, no foliar application of dinotefuran or any other insecticide in the neonecotinoid class should be made. According to the label Dinotefuran may however be used in alternation with other materials possessing dissimilar modes of action and /or with other

chemical classes of insecticides.

### Page 30 Applications of dinotefuran in outdoors are expected to be by ground application (soil application or spray) or aerial spray methods. The application rate would vary according to the type of crop and disease; for leafy vegetables, granular soil incorporat ion a one

- time application of 2.68 lbs of dinotefuran 20SG, i.e a maximum of 0.536 lb a.i/acre is allowed. For foliar sprays up to two applications are allowed with a limitation of a maximum 1.34 lbs of dinotefuran 20SG,

i.e a total maximum of 0.268 lb a. i/acre per season for leafy vegetables. Table 2 provides the proposed use profile for dinotefuran.

Table 2. Dinotefuran Use Profile

Crop lbs ai/A/ Application Max # applications minimum application interval (days) comments

Leafy Vegetable Foliar

0.045

- 0.134

Soil

0.226

- 0.268 2 7 Regardless of the application method do not apply more than a total of 2.68 lbs of Dinotefuran 20SG (0.536 lb a.i).

Turf Grasses

0.54 1

- 0.54 lb a.i/ac translates to 1.8 oz/1000 square ft of Dinotefuran 10SL product



### Approach for Dinotefuran

According to the label for dinotefuran the worst case scenario for use in the water assessment model is for use on Turf grasses. The maximum application rate provided in the label for this crop is the highest possible dosage of this chemical in a single a pplication. Because of the high solubility of dinotefuran, the maximum potential for this chemical for migration through surface water runoff or leaching exist in this particular scenario amongst all of the different application rates and methodologies sp ecified in the proposed labels provided by the registrant. The default percent cropped area (PCA) of 0.87 is used for Turf grasses. The EFED review of crop production data yielded approximate potential acreages for vegetables as 1,895,620 Acres (2001

Ce nsus of Agriculture).

Tables 3 summarizes the input values used in the model runs for FIRST1.0 and SCIGROW2.3, respectively. The lowest non

- sand K

oc 

### was used in FIRST. The median K

oc 

### value was used in

SCIGROW. There were two available aerobic soil metabolism half

- lives for dinotefuran, obtained in one soil type in a radiolabeled study. The upper confidence bound value (90 th


### percentile) of the half

- life was used for the aerobic soil metabolism in FIRST. The mean half

life was used in SCIGROW modeling. The modeling results associated with maximum allowable rate per year (0.536 lb ai/acre applied one time) are presented in Table 1. Copies of the orginal printout s from the modeling runs (FIRST and SCIGROW) are attached at the end of

this memorandum.

### Page 31 Approach for Dinotefuran’s Major Transformation Product

The Metabolism Assessment Review Committee (MARC) recommended Dinotefuran, DN, DN

2

- OH+DN

- 3

- OH, MNG, and UF, as residues of concern for water in their minutes of the meeting held on January 7, 2004. Important transformation products of dinotefuran appear to be MNG and DN. However, one aqueous photolysis study had identified UF, DN

- 2

- OH+DN

- 3

- OH, MG hydroge n chloride, and BCDN succinate as major transformation products. Since BCDN succinate and MG Hydrogen chloride were found to degrade further fairly quickly, there were no concern for these two degradates by the MARC. Out of these degradates MNG appears

t o be persistent and relatively mobile. Of these, MNG is more mobile and relatively persistent, but there is insufficient field data to confirm the laboratory findings. From the studies submitted by the registrant, the physical properties of only two trans formation products, MNG and DN were only available partially for running the models. Only partial degradation characteristics was available for MNG from one study. No degradation characteristics were available for any other degradates from the studies su bmitted by the registrant.

Due to its high persistence, dinotefuran may be available for runoff or leaching. MNG, the transformation product, also appears to be persistent and relatively mobile. It is not expected to be available for runoff and leaching in highly detectable quantities because the laboratory studies indicated that it was present at a maximum of only 13.7% of the applied which is close to the limit of concern (10% of the applied).

One mobility study was conducted on DN

- phosphate, a salt of the degradate DN. DN

- phosphate was found to be relatively less mobile compared to its parent as evidenced by its K

oc 

### values, which ranged from 58 to 2502 and yielded a mean Koc of 666. DN

- phosphate is stable to hydrolysis and aqueous photolysis (~533 days at pH7).

From all of the fate studies submitted by the registrant, the aerobic soil metabolism half

- life could be calculated for only one of the major degradate , MNG. Based upon the available information and data provided by the registrant, the degradate MNG was also simulated using the screening models, FIRST and SCIGROW. EFED had only limited environmental fate data for these transformation products; however, mobility data, a very important parameter in the screening models, was available for MNG and DN

- phosphate as listed in Tables 3a and 3b at the end. Only one study (aerobic soil metabolism) submitted by the registrant had the minimum

decline information f or MNG to calculate its half

- life. Based upon the detection of MNG in

Findak Garden loam soil the estimated half

- life for MNG in this soil was determined as 153 days. Because of the availability of only one half

- life value the input value was taken as 459 days (3x153) per the modeling guideline. This value was used in FIRST, and the single value was used for SCIGROW. MNG reached a maximum of 13.7% of the applied in the radiolabeled aerobic soil metabolism study. It is simulated by multiplying the label a pplication rate by 0.137 or 13.7% and then multiplying that by the mole ratio, i.e. molecular weight of MNG divided by the molecular weight of the parent (118/202.2) to yield 0.043 lb a.i/ac (0.54x0.137x118/202.2).

The mobility and solubility values for t he degradate DN were provided in the studies submitted by the registrant for DN

- Phosphate, a stable salt of DN. Although these studies provided a few

### Page 32 input parameters, but no aerobic soil metabolism half

- life was provided for DN and hence it was

assumed t o be stable for running the FIRST model. One aerobic aquatic half

- life was available from a study and was used as the input value for running the models. For the groundwater estimation by SCIGROW the aerobic aquatic half life was used since the degradate was formed only under aquatic condition. The aqueous photolysis half life was available for DN.

No data were available for the degradates, UF, and DN

- 2

- OH+DN

- 3

- OH (represented by DN

- 2

- OH) in any of the studies submitted by the registrant. The EPI Win pro gram was run to estimate the mobility and solubility of these two degradates. The aerobic soil metabolism half lives were not available for DN, UF and DN

- 2

- OH and also no aqueous photolysis half lives were not

available for UF and DN

- 2

- OH. The Biowin pro gram was used to estimate the biodegradation

half lives for UF and DN

- 2

- OH. Since the structure of DN was very similar to DN

- 2

- OH the aqueous photolysis half lives of these two degradates were assumed to be the same for the screening level model runs. Fo r UF the aerobic soil metabolism was estimated by the Biowin program and the aqueous photolysis half life was assumed to be stable (i.e ~500 days). For screening level modeling runs these assumptions should provide only an upper

- bound estimated

concentrat ion of the degradates in water. Should there be a need by HED, additional refinements can be made using a higher tier model. However, this will require further submission of studies by the registrant characterizing all of these degradates so that accurate input values for the

models could be determined.

The input parameters for Dinotefuran, MNG, DN, DN

- 2

- OH, and UF are presented in Table 3a, 3b, and 3c respectively. The modeling results are shown in Table 1.

### Page 33 Table 3a Environmental Fate and Other Input Parameters for Dinotefuran used in FIRST and SCIGROW

Parameter Dinotefuran MNG Source

Water Solubility (25 ° C) 39,830 ppm 11,480 ppm MRID #45640112

MRID#45639706

Hydrolysis Half

- Life (pH 7) stable stable MRID#45640102

Aerobic Soil Metabolism Half

- Life (upper confidence bound value, 90 th percentile, from 2 values) 116.4 days 459.3 (3x one value) MRID#45640112

MRID#45640111 Calculated value(MNG) Aerobic Soil Metabolism Half

- Life (mean) 81.5 days 153.1 (1)

Aerobic Aquatic Metabolism Half

- life (upper confidence bound value, 90 th
percentile, from 2 values) 80.8 days Calculated

2x459.3

= 918.6 MRID#45640117

Aqueous Photolysis Half

- Life 1.8 days 2.4 days MRID#45640105

MRID#45640107

Adsorption/Desorption Coefficient (Lowest

non

- sand K d ) 0.22 0.16 MRID#45640114

MRID#45640116

Organic Carbon Adsorption/Desorption Coefficient (lowest non

- sand K OC ) 22 16

Pesticide is Wetted

- In Yes Proposed Label

PCA (leafy vegetable, worst case scenario) 0.87 0.87 Default value for other

crops

Application Method(for Turfgrass application

- max. Application rate) Ground Spray(3) Ground Spray(3) Proposed Label

Application Rate (lb a.i./A) 0.54 0.043 (4) Proposed Label

Applications Permitted per Year 1 1 Proposed Label

Application Interval (minimum days) N/A N/A Proposed Label

Depth of Incorporation N/A N/A Proposed Label

(1). Half life for MNG was determined based upon the detection of two degrading concentrations of MNG in the aerobic soil metabolism study on Dinotefuran (MRID# 45640111) (2). Mean value was selected for SCIGROW because two values were identical. (3). Maximum application rate selected for Turfgrass, ground spray. (4). Maximum conce ntration observed in the aerobic soil metabolism study x application rate x mole ratio =
(0.137)(0.54)(118/202.2) =0.043

### Page 34 Table 3b Environmental Fate and Other Input Parameters for DN and DN

- 2

- OH used in FIRST and

SCIGROW

Parameter DN

- 2

- OH DN Source

Water Solubility (25 ° C) 1000,000 ppm (1) 619,400 ppm EPI Win program

MRID#45639707

Hydrolysis Half

- Life (pH 7) stable stable MRID#45640102

Aerobic Soil Metabolism Half

- Life (3 times single value calculated by Biowin Program) 180 N/A Calculated half Life of

DN

- 2

- OH using Biowin

program. Assumed 114 days half life (DN)

MRID#45640117. Aerobic Soil Metabolism Half

- Life (mean) 60 days 114 days (2)

Aerobic Aquatic Metabolism Half

- life (one value only) 342 days (N/A

- (assumed same as DN) 114 days x 3 = 342 days MRID#45640117 Because of highly

similar structure of DN

and DN

- 2

- OH

Aqueous Photolysis Half

- Life 533.2 days (N/A

- assumed same as DN) 533.2 days MRID#45640108

Adsorption/Desorption Coefficient (Lowest

non

- sand K d ) N/A 2.08 Calculated for DN

- 2

- OH using PCKOCwin

program MRID#45640113 Organic Carbon Adsorption/Desorption Coefficient (lowest non

- sand K OC ) 10 87

Pesticide is Wetted

- In Yes Yes Proposed Label (Parent)

PCA (leafy vegetable, worst case scenario) 0.87 0.87 Default value for other

crops

Application Method(for max. Application rate) Ground Spray(3) Ground Spray(3) Proposed Label

Application Rate (lb a.i./A) (parent 0.54) 0.1304 (4) 0.0969 (5) Proposed Label

Applications Permitted per Year 1 1 Proposed Label

Application Interval (minimum days) N/A N/A Proposed Label

Depth of Incorporation N/A N/A Proposed Label

(1). Water solubility was provided in the study for DN and calculated by EPI Win program for DN

- 2

- OH. (2). Available aerobic aquatic value was assumed for SCIGROW because the degradate formed only under aquatic condition. (3). Maximum application rate selected for Turfgrass application. (4). Maximum concentration observed in the aerobic soil metabolism study x applica tion rate x mole ratio = Mol wt. 173.2 EPI Win Program (0.282)(0.54)(173.2/202.2) (5) Maximum concentration observed in the aerobic soil metabolism study x application rate x mole ratio = Mol wt. 157.2 (MRID#45639707) (0.231)(0.54)(157.2/202.2)

### Page 35 Table 3c Environmental Fate and Other Input Parameters for UF used in FIRST and SCIGROW

Parameter Dinotefuran UF Source

Water Solubility (25 ° C) 39,830 ppm 4,171 ppm MRID #45640112 EPI Win Program

Hydrolysis Half

- Life (pH 7) stable stable MRID#45640102

Aerobic Soil Metabolism Half

- Life (upper confidence bound value, 90 th percentile, from 2 values) 116.4 days 180 days MRID#45640112 3 times single value for

UF

MRID#45640111 Calculated (UF) using Biowin Program Aerobic Soil Metabolism Half

- Life (mean) 81.5 days (2) 60 days

Aerobic Aquatic Metabolism Half

- life 80.8 days 360 (2 x 180 days) MRID#45640117

Aqueous Photolysis Half

- Life 1.8 days Assumed Stable ~500 days MRID#45640105

Adsorption/Desorption Coefficient (Lowest

non

- sand K d ) 0.22 Not available MRID#45640114

MRID#45640113 EPI Win Program Organic Carbon Adsorption/Desorption Coefficient (lowest non

- sand K OC ) 22 10.48

Pesticide is Wetted

- In Yes Yes Proposed Label (parent)

PCA (leafy vegetable, worst case scenario) 0.87 0.87 Default value for other

crops

Application Method(for max. Application rate) Ground Spray (3) Ground Spray(3) Proposed Label

Application Rate (lb a.i./A) 0.54 0.0447 (4) Proposed Label

Applications Permitted per Year 1 1 Proposed Label

Application Interval (minimum days) N/A N/A Proposed Label

Depth of Incorporation N/A N/A Proposed Label

(1). Water solubility was provided in the study for Dinotefuran (shown for comparison purposes in this Table) and calculated by EPI Win program for UF.. (2). Mean value was selected for SCIGROW for Dinotefuran and calculated value for UF using Biowin program. (3). Maximum application rate selected for Turfgrass application. (4). Maximum concentration observed in the aerobic soil metabolism study x application rat e x mole ratio = Mol wt. 158.2 (EPI Win) (0.106)(0.54)(158.2/202.2)

### Page 36 Background Information on FIRST model:

FIRST (FQPA Index Reservoir Screening Tool) is a screening model designed to estimate the pesticide concentrations found in surface water for use in drinking water assessments. It provides high

- end values on the concentrations that might be found in a small drinking water reservoir due to the use of pes ticide. Like GENEEC, the model previously used for Tier I screening level, FIRST is a single

- event model (one run

- off event), but can account for spray drift from multiple applications. FIRST takes into consideration the so called Index Drinking

Water Re servoir by representing a larger field and pond than the standard GENEEC scenario. The FIRST scenario includes a 427 acres field immediately adjacent to a 13 acres reservoir, 9 feet deep, with continuous flow (two turnovers per year). The pond receives a spray drift event from each application plus one runoff event. The runoff event moves a maximum of 8% of the applied pesticide into the reservoir. This amount can be reduced due to degradation on field and the effect of binding to soil. Spray drift is equal to 6.4% of the applied concentration from the ground spray application and 16% for aerial applications.

FIRST also makes adjustments for the percent crop area. While FIRST assumes that the entire watershed would not be treated, the use of a PCA is s till a screen because it represents the highest percentage of crop cover of any large watershed in the US, and it assumes that the entire crop is being treated. Various other conservative assumptions of FIRST include the use of a small drinking water rese rvoir surrounded by a runoff

- prone watershed, the use of the maximum use rate, no buffer zone, and a single large rainfall.

Background Information on SCIGROW model:

SCIGROW (Screening Concentration in Ground Water) provides a groundwater screening

exposu re value to be used in determining the potential risk to human health from drinking water contaminated with the pesticide. Since the SCIGROW concentrations are likely to be approached in only a very small percentage of drinking water sources, i.e., highly vulnerable aquifers, it is not appropriate to use SCIGROW for national or regional exposure estimates.

SCIGROW estimates likely groundwater concentrations if the pesticide is used at the maximum allowable rate in areas where groundwater is exceptionally vulnerable to contamination. In most cases, a large majority of the use area will have groundwater that is less vulnerable to

contamination than the areas used to derive the SCIGROW estimate.

Values below 0.006 ppb (6 ng/L) obtained by SCIGROW2.3 are bey ond the scope of the regression data and have not been verified. If concerns are raised by exposures of less than 0.006 ppb, a higher

- tier ground water exposure assessment should be considered, regardless of how low a screening concentration is returned b y SCIGROW.

Background Information for EPI Win (PcKoc, and BioWin) models :

### Page 37 The following overview of the PCKOCWIN and BioWin programs was obtained from the program manual.

PCKOCWIN Overview

The Soil Adsorption Coefficient Program (PCKOCWIN ) estimates the soil adsorption coeffiecient (K OC 

### ) of organic compounds. K OC 

### can be defined as "the ratio of the amount of chemical adsorbed per unit weight of organic carbon (OC) in the soil or sediment to the

concentration of the chemical in solution at equilibrium" (Lyman, 1990); it is represented by the following equation (Lyman, 1990):

Koc = (ug adsorbed/g organic carbon) / (ug/mL solution)

K OC 

### provides an indication of the extent to which a chemical partitions between solid and solution phases in soil, or between water and sediment in aquatic ecosystems. Estimated values

of K OC 

### are often used in environmental fate assessment because measurement of K OC 

### is expensive. Traditional estimation methods rely upon the octanol/water partition coefficient or related parameters, but recently the first

- order molecular connectivity index (1

- MCI) has been used successfully to predict K OC 

### values for hydrophobic organic compounds (Sabljic, 1984, 1987; Bahnick and Doucette, 1988). PCKOCWIN uses 1

- MCI and a series of group contribution factors to predict Koc. The group contribution method outper forms traditional estimation methods based on octanol/water partition coefficients and water solubility.

PCKOCWIN requires only a chemical structure to make these predictions. Structures are entered into PCKOCWIN by SMILES (Simplified Molecular Input Li ne Entry System)

notations.

The first

- order molecular connectivity index (MCI) has been successfully used to predict soil sorption coefficients (Koc) for nonpolar organics. For polar compounds, a new estimation

method based on MCI and series of statistic ally derived fragment contribution factors for polar compounds was developed. After developing an extensive database of measured K OC 

### values, we divided the dataset into a training set of 189 chemicals and an independent validation set of 205

chemicals. Tw o linear regressions were then performed. First, measured log K OC 

### values for nonpolar compounds in the training set were correlated with MCI. The second regression was developed by using the deviations between measured log K OC 

### and the log K OC 

### estimated w ith the nonpolar equation and the number of certain structural fragments in the polar compounds. The final equation for predicting log Koc accounts for 96% and 86% of the variation in the measured values for the training and validation sets, respectively. Results also show that the model outperforms and covers a wider range of chemical structures than do models based on

octanol

- water partition coefficients (K OW 

### ) or water solubility.

BIOWIN Overview

The Biodegradation Probability Program (BIOWIN ) estimates the probability for the rapid aerobic biodegradation of an organic chemical in the presence of mixed populations of

### Page 38 environmental microorganisms. Estimates are based upon fragment constants that were developed using multiple linear and non

- lin ear regression analyses.

BIOWIN requires only a chemical structure to make these predictions. Structures are entered into BIOWIN by SMILES (Simplified Molecular Input Line Entry System) notations. The BIOWIN program was developed at Syracuse Research Co rporation. The prediction methodology was developed jointly by efforts of the Syracuse Research Corporation and the U.S. Environmental Protection Agency.

Two independent training sets were used to develop four mathematical models for predicting

aerobic b iodegradability from chemical structure. All four of the models are based on multiple regressions against counts of 36 preselected chemical substructures plus molecular weight. Two of the models, based on linear and nonlinear regressions, calculate the p robability of rapid biodegradation and can be used to classify chemicals as rapidly or not rapidly biodegradable. The training set for these models consisted of qualitative summary evaluations of all available experimental data on biodegradability for 295 chemicals. The other two models allow

semi

- quantitative prediction of primary and ultimate biodegradation rates using multiple linear regression. The training set for these models consisted of estimates of primary and ultimate biodegradation rates for 2 00 chemicals, gathered in a survey of 17 biodegradation experts. The two probability models correctly classified 90% of the chemicals in their training set, whereas the two survey models calculated biodegradation rates for the survey chemicals with R 2 

### = 0 .7. These four models are intended for use in chemical screening and in setting priorities for further

review.

### Page 39 Appendix I to the Drinking Water memo

Modeling Results :

**FIRST Run for Dinotefuran**

**- Turfgrass** 

, **Ground Spray** Jan 21, 2004

RUN No. 2 FOR Dinotefuran ON Turfgrass * INPUT VALUES *

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

RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

ONE(MULT) INTERVAL Koc (PPM ) ( %DRIFT) AREA (IN)

-------------------------------------------------------------------- .540( .540) 1 1 22.039830.0 GROUND( 6.4) 87.0 .0

FIELD AND RESERVOIR HALFLIFE VALUES (DAYS)

-------------------------------------- ------------------------------
METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

(FIELD) RAIN/RUNOFF (RESERVOIR) (RES.

- EFF) (RESER.) (RESER.)

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

138. 44 0 N/A 1.80

- 223.20 82.73 60.36

UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

-------------------------------------------------------------------- PEAK DAY ( ACUTE) ANNUAL AVERAGE (CHRONIC)

CONCENTRATION CONCENTRATION

-------------------------------------------------------------------- 48.203 8.007

**FIRST Run MNG**

**- Turfgrass Grou**  **nd spray** Jan 21, 2004

RUN No. 1 FOR MNG ON Turfgrass * INPUT VALUES *

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

RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

ONE(MULT ) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

-------------------------------------------------------------------- .043( .043) 1 1 16.011480.0 GROUND( 6.4) 87.0 .0

FIELD AND RESERVOIR HALFLIFE VALUES (DAYS)

----- ---------------------------------------------------------------
METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

(FIELD) RAIN/RUNOFF (RESERVOIR) (RES.

- EFF) (RESER.) (RESER.)

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

459.30 0 N/A 2.40

- 297.60 918.60 224.78

UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

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

PEAK D AY (ACUTE) ANNUAL AVERAGE (CHRONIC)

CONCENTRATION CONCENTRATION

-------------------------------------------------------------------- 3.860 1.631

### Page 40 Modeling Results :

**FIRST Run for DN** (Degradate of Dinotefuran) Jan 21, 2004

RUN No. 1 FOR DN ON Turfgrass * INPUT VALUES *

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

RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

-------------------------------------------------------------------- .097( .097) 1 1 87.0 619,400 GROUND( 6.4) 87.0 .0

FIELD AND RESERVOIR HALFLIFE VALUES (DAYS)

--------------------------------------------------------------------
METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

(FIELD) RAIN/RUNOFF (RESERVOIR) (RES.

- EFF) (RESER.) (RESER.)

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

114.00 0 N/A 533.20

- 66116.80 342.00 340.24

UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

----------------------------------------- --------------------------- PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC)

CONCENTRATION CONCENTRATION

-------------------------------------------------------------------- 7.774 3.322

Modeling Results:

**FIRST Run for UF** (Degradate of Dinotefuran) Jan 21, 2004

RUN No. 3 FOR UF ON Turfgrass * INPUT VALUES *

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

RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

-------------------------------------------------------------------- .045( .045) 1 1 10.5 4171. 0 GROUND( 6.4) 87.0 .0

FIELD AND RESERVOIR HALFLIFE VALUES (DAYS)

--------------------------------------------------------------------
METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

(FIELD) RAIN/RUNOFF (RESERVO IR) (RES.

- EFF) (RESER.) (RESER.)

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

180.00 0 N/A 500.00

- 62000.00 360.00 357.92

UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

-------------------------------------------------------------------- PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC)

CONCENTRATION CONCENTRATION

--------------------------------------------------------- ----------- 4.069 2.070

### Page 41 Modeling Results:

**FIRST Run for DN**

**- 2** 

**- OH+DN** 

**- 3** 

**- OH**  (Degradate of Dinotefuran) Jan 21, 2004

RUN No. 1 FOR DN

- 2

- OH ON Turfgrass * INPUT VALUES *

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

RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

-------------------------------------------------------------- ------ .130( .130) 1 1 10.0 1,000,000 GROUND( 6.4) 87.0 .0

FIELD AND RESERVOIR HALFLIFE VALUES (DAYS)

--------------------------------------------------------------------
METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABO LIC COMBINED

(FIELD) RAIN/RUNOFF (RESERVOIR) (RES.

- EFF) (RESER.) (RESER.)

-------------------------------------------------------------------- 60.00 0 N/A 533.20

- 66116.80 342.00 340.24

UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

-------------------------------------------------------------------- PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC)

CONCENTRATION CONCENTRATION

--------- ----------------------------------------------------------- 11.881 5.952

Modeling Results :

**SCIGROW Run for Dinotefuran**

SCIGROW

VERSION 2.3

ENVIRONMENTAL FATE AND EFFECTS DIVISION

OFFICE OF PESTICIDE PROGRAMS

U.S. ENVIRONMENTAL PROTECTION AGENCY

SCREENING MODEL

FOR AQUATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical:Dinotefuran

time is 8/28/2003 9:12:37

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

Application Number of Total Use Koc Soil Aerobic

rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------ 0.536 1.0 0.536 2.20E+01 81.5

---------------------------------------------- -------------------------- groundwater screening conc. (ppb) = 2.75E+00

************************************************************************

Modeling Results :

**SCIGROW Run for MNG**

SCIGROW

VER SION 2.3

ENVIRONMENTAL FATE AND EFFECTS DIVISION

### Page 42 OFFICE OF PESTICIDE PROGRAMS

U.S. ENVIRONMENTAL PROTECTION AGENCY

SCREENING MODEL

FOR AQUATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical:MNG

- Degradate

time is 8/28/2003 14:42:51

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

Application Number of Total Use Koc Soil Aerobic
rate (lb/acre) applications (lb/a cre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------ 0.043 1.0 0.043 1.60E+01 153.1

------------------------------------------------------------------------ groundwater screening conc. (ppb) = 8.63E

- 01

************************************************************************

SCIGROW

VERSION 2.3

SciGrow version 2.3

chemical: **DN**
time is 1/12/2004 1 0:48:26

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

Application Number of Total Use Koc Soil Aerobic
rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

----------------------------- ------------------------------------------- 0.096 1.0 0.096 8.70E+01 114.0

------------------------------------------------------------------------ groundwater screening conc. (ppb) = 1.88E

- 01

********************* ***************************************************

SciGrow version 2.3

chemical: **UF**
time is 1/13/2004 10:26:44

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

Application Number of Total Use Koc Soil Aero bic
rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------ 0.045 1.0 0.045 7.00E+00 60.0

------------------------------------ ------------------------------------ groundwater screening conc. (ppb) = 3.22E

- 01

************************************************************************

SCIGROW

VERSION 2.3

FOR AQ UATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical: **DN**

**- 2** 

**- OH** 
time is 1/13/2004 10:31:58

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

Application Number of Total Use Koc Soil Aerobic
rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------ 0.130 1.0 0.130 7.00E+00 60.0

---------------------------------------- -------------------------------- groundwater screening conc. (ppb) = 9.38E

- 01

************************************************************************

### Page 43 Outputs from EPI Suite Programs for UF and DN

- 2

- OH

SMILES : CNC(=N)NCC1(O)CCOC1

CHEM : **DN**

**- 2** 

**- OH** 

MOL FOR: C7 H15 N3 O2

MOL WT : 173.22

------------------------------ **EPI SUMMARY** (v3.10)

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

Physical Property Inputs:
Water Solubility (mg/L):

------ Vapor Pressure (mm Hg) :

------ Henry LC (atm

- m3/mole) :

------ Log Kow (octanol

- water):

------ Boiling Point (deg C) :

------ Melting Point (deg C) :

------

Log Octanol

- Water Partition Coef (SRC):
Log Kow (KOWWIN v1.66 estimate) =

- 1.68

Boiling Pt, Melting Pt, Vapor Pressure Esti mations (MPBPWIN v1.40):
Boiling Pt (deg C): 304.38 (Adapted Stein & Brown method)
Melting Pt (deg C): 96.00 (Mean or Weighted MP)

VP(mm Hg,25 deg C): 2.09E

- 005 (Modified Grain method)

Water Solubility Estimate from Log Kow (WSKOW v1.40 ):
Water Solubility at 25 deg C (mg/L): 1e+006

log Kow used:

- 1.68 (estimated)

no

- melting pt equation used

ECOSAR Class Program (ECOSAR v0.99g):

Class(es) found:
Aliphatic Amines

Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:

Bond Method : 6.27E

- 018 atm

- m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 4.764E

- 012 atm

- m3/mole

Probability of Rapid Biodegradation (BIOWIN v4.00):

Line ar Model : 0.1338

Non

- Linear Model : 0.0099
Expert Survey Biodegradation Results:
Ultimate Survey Model: 2.5956 (weeks

- months)
Primary Survey Model : 3.4346 (days

- weeks )
Readily Biodegradable Probability (MITI Model):

Linear Model : 0.3749

Non

- Linear Model : 0.2641

Atmospheric Oxidation (25 deg C) [AopWin v1.90]:
Hydroxyl Radicals Reaction:

OVERALL OH Rate Constant = 186.7036 E

- 12 cm3/molecule

- sec

Half

- Life = 0.057 Days (12

- h r day; 1.5E6 OH/cm3)

Half

- Life = 0.687 Hrs

Ozone Reaction:

No Ozone Reaction Estimation

Soil Adsorption Coefficient (PCKOCWIN v1.66):

Koc : 10

### Page 44 Log Koc: 1.000

Aqueous Base/Acid

- Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:

Rate constants can NOT be estimated for this structure!

BCF Estimate from Log Kow (BCFWIN v2.14):

Log BCF = 0.500 (BCF = 3.162)
log Kow used:

- 1.68 (estimated)

Volatilization from Water : Henry LC: 6.27E

- 018 atm

- m3/mole (estimated by Bond SAR Method)

Half

- Life from Model River: 1.229E+014 hours (5.121E+012 days)

Half

- Life from Model Lake : 1.341E+015 hours (5.586E+013 days)

Removal In Wastewater Treatment:

Total removal: 1.85 percent
Total biodegradation: 0.09 percent
Total sludge adsorption: 1.75 percent
Total to Air: 0.00 percent

Level III Fugacity Model:

Mass Amount Half

- Life Emissions

(percent) (hr) (kg/hr)

Air 1.09e

- 010 1.37 1000

Water 49.8 900 1000

Soil 50.1 900 1000

Sediment 0.0918 3.6e+003 0

Persistence Time: 789 hr

------------------------------------------------------------------------------ SMILES : CNC(=N)NCC1(O)CCOC1

CHEM : **DN**

**- 2** 

**- OH** 

MOL FOR: C7 H15 N3 O2

MOL WT : 173.22

------------------------- -- **BIOWIN v4.00** Results

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

Linear Model Prediction : Does Not Biodegrade Fast

Non

- Linear Model Prediction: Does Not Biodegrade Fast
Ultimate Biodegradation Timeframe: Weeks

- Months
Primary Biodegradation Tim eframe: Days

- Weeks
MITI Linear Model Prediction : Not Readily Degradable

MITI Non

- Linear Model Prediction: Not Readily Degradable

------ +

----- +

-------------------------------------------- +

--------- +

---------

TYPE | NUM | BIOWIN FRAGM ENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

---------

Frag | 1 | Carbon with 4 single bonds & no hydrogens |

- 0.1839 |

- 0.1839 Frag | 1 | Aliphatic ether [C

- O

- C] |

- 0.3474 |

- 0.3474 MolWt| * | Molecular Weight Parameter | |

- 0.0825 Const| * | Equation Constant | | 0.7475

============+============================================+=========+========= RESULT | LINEAR BIODEGRADATION PROBABILITY | | 0.1338

============+============================================+=========+=========

------ +

----- +

-------------------------------------------- +

--------- +

---------

TYPE | NUM | B IOWIN FRAGMENT DESCRIPTION | COEFF | VALUE

### Page 45 ------ +

----- +

-------------------------------------------- +

--------- +

---------

Frag | 1 | Carbon with 4 single bonds & no hydrogens |

- 1.7232 |

- 1.7232 Frag | 1 | Aliphatic ether [C

- O

- C] |

- 3.4294 |

- 3.4294 MolWt| * | Molecular Weight Parameter | |

- 2.4597

============+============================================+=========+========= RESULT | NON

- LINEAR BIODEGRADATION PROBABILITY | | 0.0099

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates

-- > Biodegrades Fast
A Probability Less Than 0.5 indicates

-- > Does NOT Biodegrade Fast

------ +

----- +

----- --------------------------------------- +

--------- +

---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

---------

Frag | 1 | Carbon with 4 single bond s & no hydrogens |

- 0.2121 |

- 0.2121 Frag | 1 | Aliphatic ether [C

- O

- C] |

- 0.0087 |

- 0.0087 MolWt| * | Molecular Weight Parameter | |

- 0.3828 Const| * | Equation Constant | | 3.1992

============+============================================+=========+========= RESULT | SURVEY MODEL

- ULTIMATE BIODEGRADATION | | 2.5956

============+============================================+=========+=========

------ +

---- - +

-------------------------------------------- +

--------- +

---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

---------

Frag | 1 | Carbon with 4 sing le bonds & no hydrogens |

- 0.1534 |

- 0.1534 Frag | 1 | Aliphatic ether [C

- O

- C] |

- 0.0097 |

- 0.0097 MolWt| * | Molecular Weight Parameter | |

- 0.2499 Const| * | Equation Constant | | 3.8477

============+============================================+=========+========= RESULT | SURVEY MODEL

- PRIMARY BIODEGRADATION | | 3.4346

============+============================================+=========+=========

Re sult Classification: 5.00

- > hours 4.00

- > days 3.00

- > weeks

(Primary & Ultimate) 2.00

- > months 1.00

- > longer

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

SMILES : CNC(=O)NCC1CCOC1

CHEM : **UF**

MOL FOR: C7 H14 N2 O2

MOL WT : 158.20

------------------------------ **EPI SUMMARY** (v3.10)

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

Physical Property Inputs:
Water Solubility (mg/L):

------ Vapor Pressure (mm Hg) :

------ Henry LC (atm

- m3/mole) :

------

Lo g Kow (octanol

- water):

------ Boiling Point (deg C) :

------ Melting Point (deg C) :

------

Log Octanol

- Water Partition Coef (SRC):
Log Kow (KOWWIN v1.66 estimate) =

- 0.10

Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.40):
Boiling Pt (deg C): 291.40 (Adapted Stein & Brown method)
Melting Pt (deg C): 79.04 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 0.000941 (Modified Grain method)

Water Solubility Estimate from Log Kow (WSKOW v1.40):

Water Solu bility at 25 deg C (mg/L): 4171

### Page 46 log Kow used:

- 0.10 (estimated)

no

- melting pt equation used

ECOSAR Class Program (ECOSAR v0.99g):

Class(es) found:
Neutral Organics

Ureas(substituted)

Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:

Bond Method : 2.67E

- 012 atm

- m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 4.696E

- 008 atm

- m3/mole

Probability of Rapid Biodegradation (BIOWIN v4.00):

Linear Model : 0.3249

Non

- Linear Model : 0.0649
Expert Survey Biodegradation Results:
Ultimate Survey Model: 2.8409 (weeks )
Primary Survey Model : 3.6098 (days

- weeks )
Readily Biodegradable Probability (MITI Model):

Linear Model : 0.3644

Non

- Linear Model : 0.2461

Atmospheric Oxidation (25 deg C) [AopWin v1.90]:
Hydroxyl Radicals Reaction:

OVERALL OH Rate Constant = 25.3856 E

- 12 cm3/molecule

- sec

Half

- Life = 0.421 Days (12

- hr day; 1.5E6 OH/cm3)

H alf

- Life = 5.056 Hrs

Ozone Reaction:

No Ozone Reaction Estimation

Soil Adsorption Coefficient (PCKOCWIN v1.66):

Koc : 10.48
Log Koc: 1.020

Aqueous Base/Acid

- Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:

Rate const ants can NOT be estimated for this structure!

BCF Estimate from Log Kow (BCFWIN v2.14):

Log BCF = 0.500 (BCF = 3.162)
log Kow used:

- 0.10 (estimated)

Volatilization from Water:

Henry LC: 2.67E

- 012 atm

- m3/mole (estimated by Bond SAR Method)

Half

- Life from Model River: 2.758E+008 hours (1.149E+007 days)

Half

- Life from Model Lake : 3.009E+009 hours (1.254E+008 days)

Removal In Wastewater Treatment:
Total removal: 1.85 percent
Total biodegradation: 0.09 percent
Total sludge adsorption: 1.76 percent
Total to Air: 0.00 percent

Level III Fugacity Model:

Mass Amount Half

- Life Emissions

(percent) (hr) (kg/hr)

Air 8.6 5e

- 005 10.1 1000

### Page 47 Water 45 360 1000

Soil 54.9 360 1000

Sediment 0.0755 1.44e+003 0

Persistence Time: 421 hr

### 48 --------------- --------------------------------------------------------------- SMILES : CNC(=O)NCC1CCOC1

CHEM : **UF**

MOL FOR: C7 H14 N2 O2

MOL WT : 158.20

--------------------------- **BIOWIN** v4.00 Results

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

Linear Model Prediction : Does Not Biodegrade Fast

Non

- Linear Model Prediction: Does Not Biodegrade Fast
Ultimate Biodegradation Timeframe: Weeks
Primary Biodegradation Timeframe: Days

- Weeks

MITI Linear Model Prediction : No t Readily Degradable

MITI Non

- Linear Model Prediction: Not Readily Degradable

------ +

----- +

-------------------------------------------- +

--------- +

---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

--- ----------------------------------------- +

--------- +

---------

Frag | 1 | Aliphatic ether [C

- O

- C] |

- 0.3474 |

- 0.3474 MolWt| * | Molecular Weight Parameter | |

- 0.0753 Const| * | Equation Constant | | 0.7475

============+============================================+=========+========= RESULT | LINEAR BIODEGRADATION PROBABILITY | | 0.3249

============+============================================+====== ===+=========

------ +

----- +

-------------------------------------------- +

--------- +

---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

---------

Frag | 1 | Aliphatic ether [C

- O

- C] |

- 3.4294 |

- 3.4294 MolWt| * | Molecular Weight Parameter | |

- 2.2465

============+============================================+=========+========= RESULT | NON

- LINEAR BIODEGRADATION PROBABILITY | | 0.0649

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates

-- > Biodegrades Fast
A Probability Less Than 0.5 indicates

-- > Doe s NOT Biodegrade Fast

------ +

----- +

-------------------------------------------- +

--------- +

---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

---------

Frag | 1 | Aliphatic ether [C

- O

- C] |

- 0.0087 |

- 0.0087 MolWt| * | Molecular Weight Parameter | |

- 0.3496 Const| * | Equation Constant | | 3.1992

============+============ ================================+=========+========= RESULT | SURVEY MODEL

- ULTIMATE BIODEGRADATION | | 2.8409

============+============================================+=========+=========

------ +

----- +

----------------------------------- --------- +

--------- +

---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

---------

Frag | 1 | Aliphatic ether [C

- O

- C] |

- 0.0097 |

- 0.0097 MolWt| * | Molecular Weight Parameter | |

- 0.2282 Const| * | Equation Constant | | 3.8477

============+============================================+=========+========= RESULT | S URVEY MODEL

- PRIMARY BIODEGRADATION | | 3.6098

============+============================================+=========+=========

Result Classification: 5.00

- > hours 4.00

- > days 3.00

- > weeks

(Primary & Ultimate) 2.00

- > months 1.00

- > longer

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