Document ID: EPA-HQ-OPP-2009-0013-0007
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2009-12-18T05:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON D.C., 20460

                                                                     
OFFICE OF 

                                                                 
PREVENTION, PESTICIDES AND

                                                                   
TOXIC SUBSTANCES

January 23, 2009

PC Code: 044312

DP Bar Code: D357111

MEMORANDUM

SUBJECT:	Tier I Estimated Drinking Water Concentrations of Dinotefuran
and its Transformation Products of Concern MNG, DN, UF and DN-2-OH +
DN-3-OH, for Use 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)

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)

 such as Safari™ 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
ornamentals, 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 Water Analysis, with
electronic copy attached 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 waters
concentrations.  Please, refer to Appendix C for original memorandum.

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-OH1	

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.  Its PC code is 044312 and its CAS
number is 165252-70-0.  Dinotefuran belongs to a broad group of
insecticides 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 acetylcholine
receptor agonists/ antagonists, group 4A insecticides (  HYPERLINK
"http://www.irac-online.org"  www.irac-online.org ).  These compounds
target the nicotinic acetylcholine receptors (nAChR) site and activate
post-synaptic acetylcholine receptors. Dinotefuran, 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 formational 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 Chemical 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 (lettuce) and potato; it is used also on ornamental plants
and turf.  However, 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
greens (broccoli raab, Chinese cabbage (Bok Choy), collards, kale,
mizuna, mustard greens, mustard spinach, rape greens and turnip greens).
 Please, refer to Appendix A for a summary of the use information
gathered from the current and proposed labels.

This is a Tier I screening-level Drinking Waters 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 minimum 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 dinotefuran 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 individual 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 Dinotefuran (data
obtained from current and 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 hybrids	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 Lettuce,
Orach, Parsley, Garden & Winter Purslane, Radichio, Rhubarb, Spinach,
New Zealand & Vine Spinach, Swiss Chard	Foliar:  0.134 @ 7 days interval

Or 

Soil:  0.33	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

Or 

Soil:  0.33	0.198 Foliar

Or 

0.33   Soil	F, S

Do not combine foliar app. with soil applications, or vice versa.	G w.
airblast, A

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

Ornamental plants in greenhouses, nurseries, interior plantscapes, lath
and shadehouses and outdoor landscapes (commercial, industrial,
recreational and residential) or Ornamental 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-furylmethyl) 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   SEQ CHAPTER \h \r 1 EPI Suite, v3.12 SMILES String found as of
9/29/06.

Unlabeled

	

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  SEQ CHAPTER \h \r 1  (ISIS
v2.3/Universal SMILES).

N(=O)(=O)NC(=N)NC   SEQ CHAPTER \h \r 1 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.

	

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.

	

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 Human 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 Concentrations
(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 risk 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. 

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-OH1	

11.88	

5.95	

0.94

1 - DN-2-OH represents DN-2-OH+DN-3-OH.  These two were reported jointly
as one metabolite in the study.

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 scenario.  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 to
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 level 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 Information 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 vegetables, 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 dinotefuran 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 application 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.

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 incorporation 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	 ADVANCE \d6 minimum application interval (days)	
ADVANCE \d6 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 application.  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 specified 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
Census of Agriculture). 

Tables 3 summarizes the input values used in the model runs for
FIRST1.0 and SCIGROW2.3, respectively.  The lowest non-sand Koc was used
in FIRST.  The median Koc 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 (90th 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 printouts from the modeling runs (FIRST and SCIGROW) are
attached at the end of this memorandum.

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 hydrogen 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
to 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 transformation 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 submitted 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 Koc 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 for 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
application 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 the 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 input parameters, but no
aerobic soil metabolism half-life was provided for DN and hence it was
assumed to 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 program 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
program 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.  For 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 concentration 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. 



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, 90th
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, 90th 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 Kd)	

0.22	

0.16	

MRID#45640114

MRID#45640116

Organic Carbon Adsorption/Desorption Coefficient (lowest non-sand KOC)	

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 concentration observed in the aerobic soil metabolism
study x application rate x mole ratio = 

                                                                        
                                                            
(0.137)(0.54)(118/202.2)=0.043



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 Kd)	

N/A	

2.08	

Calculated for DN-2-OH using PCKOCwin program

MRID#45640113

Organic Carbon Adsorption/Desorption Coefficient (lowest non-sand KOC)	

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 application 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)



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, 90th
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 Kd)	

0.22	

Not available	

MRID#45640114

MRID#45640113

EPI Win Program

Organic Carbon Adsorption/Desorption Coefficient (lowest non-sand KOC)	

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 rate x mole ratio =   

                             Mol wt. 158.2 (EPI Win)                    
                              (0.106)(0.54)(158.2/202.2)

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.  FIRST 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, 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 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 assumptions 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.

Background Information on SCIGROW model:

SCIGROW (Screening Concentration in Ground Water) provides a groundwater
screening 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
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 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 is returned by SCIGROW.    

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

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 (KOC) of organic compounds.  KOC 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)

KOC 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 KOC are often used in
environmental fate assessment because measurement of KOC 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 KOC 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 outperforms 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 Line 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
statistically derived fragment contribution factors for polar compounds
was developed. After developing an extensive database of measured KOC
values, we divided the dataset into a training set of 189 chemicals and
an independent validation set of 205 chemicals.  Two linear regressions
were then performed.  First, measured log KOC values for nonpolar
compounds in the training set were correlated with MCI.  The second
regression was developed by using the deviations between measured log
KOC and the log KOC estimated with 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 (KOW) 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 environmental microorganisms. 
Estimates are based upon fragment constants that were developed using
multiple linear and non-linear 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 Corporation.  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 biodegradability 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
probability 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 200 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 R2 = 0.7.  These four models are intended for use in chemical
screening and in setting priorities for further review.

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 Ground 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 DAY  (ACUTE)      ANNUAL AVERAGE (CHRONIC)      

          CONCENTRATION             CONCENTRATION            

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

              3.860                      1.631



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  (RESERVOIR)  (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

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   METABOLIC  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

                          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:MNG-Degradate

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

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

  Application      Number of       Total Use    Koc      Soil Aerobic

  rate (lb/acre)  applications   (lb/acre/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  10:48:26

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

  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 Aerobic

  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 AQUATIC 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 

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

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 Estimations (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):

    Linear 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-hr day; 1.5E6 OH/cm3)

      Half-Life =     0.687 Hrs

   Ozone Reaction:

      No Ozone Reaction Estimation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):

      Koc    :  10

      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 Timeframe:  Days-Weeks

    MITI Linear Model Prediction    :  Not Readily Degradable

    MITI Non-Linear Model Prediction:  Not Readily Degradable

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

 TYPE | NUM |        BIOWIN FRAGMENT 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 |        BIOWIN FRAGMENT DESCRIPTION         |  COEFF  | 
VALUE  

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

 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 bonds & 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 single 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

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

 Result 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) :   ------

    Log 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 Solubility at 25 deg C (mg/L):  4171

       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)

      Half-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 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: -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       8.65e-005       10.1         1000       

   Water     45              360          1000       

   Soil      54.9            360          1000       

   Sediment  0.0755          1.44e+003    0          

     Persistence Time: 421 hr

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

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    :  Not 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 --> Does 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                         |      
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------+-----+--------------------------------------------+---------+----
-----

 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   |   SURVEY MODEL - PRIMARY BIODEGRADATION    |         | 
3.6098

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

 Result Classification:   5.00 -> hours     4.00 -> days    3.00 ->
weeks

  (Primary & Ultimate)    2.00 -> months    1.00 -> longer

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

Page  PAGE  11 

Page  PAGE  19