Alexander B. Grannis
Commissioner 

### New York State Department of Environmental Conservation

Division of Solid and Hazardous Materials
Bureau of Pesticides Management, 11 th Floor 625 Broadway, Albany, New York 12233-7254

Phone: (518) 402-8788 • Fax: (518) 402-9024

Website: http://www.dec.ny.gov

January 14, 2009

CERTIFIED MAIL RETURN RECEIPT REQUESTED

Ms. Teresa McMullin State Registration Specialist Arysta LifeScience North America, LLC 15401 Weston Parkway, Suite 150 Cary, North Carolina 27513

Dear Ms. McMullin:

Re: Withdrawal of Applications to Re gister the New Active Ingredient (NAI)

Iodomethane Contained in the Pesticide Products: Iodomethane Technical (EPA Reg. No. 66330-44)

Midas 7 98:2 (EPA Reg. No. 66330-43)

Midas 7 25:75 (EPA Reg. No. 66330-42)

Midas 7 33:67 (EPA Reg. No. 66330-59)

Midas 7 50:50 (EPA Reg. No. 66330-57)

Midas 7 EC Bronze (EPA Reg. No. 66330-58)

Midas 7 EC Gold (EPA Reg. No. 66330-60)

The New York State Department of Environmental Conservation (Department) accepts your request for withdrawal of the applications to register Iodomethane Technical and six enduse Midas 7 products containing the new active ingred ient iodomethane (Chemical Code 11).

The Department reviewed the applications and data package, received November 16, 2007, submitted by Technology Sciences Group on behalf of Arysta LifeScience North America, LLC (Arysta) regarding registration of the re ferenced products in New York State. The applications were deemed complete for purposes of technical review on January 15, 2008. Pursuant to the time frames specified in Environmental Conservation Law (ECL) ' 33-0704.2, registration decisions were due by June 13, 2008. The registration decision date was waived in order to allow Arysta to address the questions/issues noted in the Department = s technical issues letter, dated June 20, 2008. Due to a lack of response to the concerns noted in the technical issues letter, the Department issued a notice of intent to deny letter on November 20, 2008. On December 19, 2008 the Department received your request to withdraw the subject applications.

Iodomethane Technical (99.8% iodomethane) is labeled for formulation or repackaging purposes only.Ms. Teresa McMullin 2.

The end-use Midas 7 products contain various mixtures of iodomethane (Chemical Code 11) and chloropicrin (Chemical Code 81501) and are labeled for preplant fumigations of fields intended for commercial production of certain listed crops and field-grown ornamentals to control soil-borne pests including weed seeds, nematodes, insects, and diseases. Chloropicrin is a component of products currently registered in the State for the preplant fumigation use pattern.

Midas 7 98:2 (97.8% iodomethane:2% chloropicrin), Midas 7 25:75 (24.95% iodomethane:74.63% chloropicrin), Midas 7 33:67 (32.93% iodomethane:66.67% chloropicrin)

and Midas 7 50:50 (49.90% iodomethane:49.75% chloropicrin) are labeled for application via three preplant soil fumigation techniques: 1) raised bed soil fumigation for field-grownornamentals, peppers, strawberries and tomatoes, 2) broadcast/flat fume soil fumigation for fieldgrown ornamentals, peppers, strawberries, tomato es, turf, stone fruits, tree nuts, vines (table, raisin and wine grapes) and nurseries, 3) deep injection auger probe for stone fruits, tree nuts, vines, and field grown ornamental trees and shrubs.

Midas 7 EC Bronze (49.90% iodomethane:44.78% chloropicrin), Midas 7 EC Gold (32.93% iodomethane:61.69% chloropicrin) are labeled for preplant raised bed drip irrigation (chemigation) for field-grown ornamentals, peppers, strawberries and tomatoes.

The Department conducted human health and environmental fate risk assessments for

iodomethane and the Midas 7 products. An ecological effects risk assessment was not produced

for this review.

HUMAN HEALTH RISK ASSESSMENT : Iodomethane technical is labeled for formulation or repackaging purposes only. The six end-use products contain various mixtures of iodomethane and chloropicrin and are labeled as preplant fumigants to control soil-borne pests including weed seeds, nematodes, insects, and dis eases in certain field crops, fruit and nut trees and field-grown ornamentals. Iodomethane is considered a replacement for methyl bromide and the above-listed pesticide products are federal A Restricted Use Pesticides @ due to acute toxicity concerns. Chloropicrin is a component of products currently registered in the State for use in preplant fumigation.

On an acute basis, iodomethane technical was moderately toxic to laboratory animals via the oral route of exposure, slightly toxic via the dermal route of exposure, but not very toxic via the inhalation route of exposure. This active ingredient was corrosive to the eyes and a severe skin irritant (tested on rabbits), but not a skin sensitizer (tested on guinea pigs).

Acute toxicity studies conducted on the Midas 7 98:2 and Midas 7 25:75 formulated products were used by the United States Environmental Protection Agency (USEPA) as representatives of the other four formulated products. In these acute studies, Midas 7 98:2 was moderately toxic to laboratory animals via the oral route of exposure, but not very toxic via the dermal and inhalation routes of exposure. Midas 7 25:75 was moderately toxic via the oral and inhalation routes of exposure and slightly toxic via the dermal route of exposure. Both formulated end-use products were corrosive to the eyes, severe skin irritants, and dermalMs. Teresa McMullin 3.

sensitizers.

Iodomethane caused some effects in an acute inhalation neurotoxicity study and a subchronic inhalation toxicity study in rats. In the neurotoxicity study, iodomethane caused clonic convulsions, decreased body temperatures, and decreased motor activity in rats exposed via whole-body inhalation (single exposure for a duration of six hours) to a concentration of 93 parts-per-million (ppm) iodomethane; the no-obser ved-effect-level (NOEL) was 27 ppm. In the subchronic study, decreases in body weights, body weight gains and food consumption (in males) were observed at a concentration of 70 ppm; the NOEL was 21 ppm. Port-of-entry effects characterized by degeneration of the olfactory epithelium also occurred at 70 ppm; the NOEL was 21 ppm.

Iodomethane caused some developmental toxicity in the offspring of pregnant rabbits, but not pregnant rats, exposed via inhalation to this chemical during organogenesis. In rabbits, increased fetal losses and decreased fetal weights were reported at maternal exposures to 20 ppm; the NOEL was 10 ppm. Maternal toxicity was not observed at concentrations up to 20 ppm (the highest level tested). In rats, maternal toxicity consisting of decreased body weight gain occurred at a concentration of 60 ppm; the NOEL was 20 ppm. No developmental toxicity was observed at concentrations up to 60 ppm (the highest level tested). In a two-generation reproduction study in rats, decreases in body wei ght gain, body weight and thymus weights in offspring as well as delays in vaginal patency were reported at 20 ppm; the NOEL was 5 ppm. Parental toxicity consisting of decreased body weight gain and body weight, organ weight changes, gross pathology and histopathology findings occurred at 50 ppm; the NOEL was 20

ppm.

The genotoxic and oncogenic potential of iodomethane were evaluated. While iodomethane was negative in a number of genotoxicity studies, it induced structural chromosomal aberrations in a Chinese hamster ovary cell assay. Chronic inhalation exposure of iodomethane was associated with an increased incidence of salivary gland squamous cell metaplasia in rats at 20 ppm; the NOEL was 5 ppm. In addition, degeneration of the olfactory epithelium, as well as perturbations of the thyroid-pituitary axis and thyroid histopathology findings, were reported at 60 ppm. Although the ch ronic inhalation/carcinogenicity study in rats demonstrated an increased incidence of follicular cell tumors, the USEPA determined that the operative mode of action for this response is the sustained perturbation of thyroid hormone homeostasis. Based on evidence that rats are more sensitive than humans to development of thyroid follicular cell tumors (in response to t hyroid hormone imbalance), the USEPA classified

iodomethane as A not likely to be carcinogenic to humans in the absence of altered thyroid

hormone homeostasis. @

The USEPA considered toxicity data and information to develop a physiologically-based pharmacokinetic (PBPK) model to better characterize the exposures associated with the critical effects of iodomethane. For this purpose, a human study of comparative fetal cord blood and

maternal blood iodide levels was conducted. Th e USEPA concluded from this study that human

fetuses do not concentrate iodide relative to maternal iodide concentration. These chemicalMs. Teresa McMullin 4.

specific data were used to better estimate human equivalent concentrations (HECs) for the aforementioned critical effects from the appropriate toxicity study. The HECs were then used in

the USEPA = s bystander and occupational risk assessments.

The USEPA estimated HECs for a number of toxicity endpoints for acute-,short/intermediate-, and long-term occupational and bystander inhalation exposures. For acuteterm occupational and bystander exposures, toxicity endpoints included nasal histopathology in the subchronic rat study, fetal losses in the rabbit developmental toxicity study, and neurotoxicity in rats. Respective HECs for these endpoints were estimated to be 4.5 ppm, 7.4 ppm, and 10 ppm for bystander exposures and 5.8 ppm, 23 ppm, and 10 ppm for occupational exposures (the difference in HECs between these two groups is in part due to different assumptions for duration of exposure). For short/intermediate-term exposures, an estimated HEC of 1.25 ppm from the rat multigeneration reproduction study (d ecreased pup weight, weight gain and thymus weights and delays in vaginal patency) was selected for bystander exposures and an estimated HEC of 3.7 ppm from the rat subchronic toxicity study (nasal histopathology) was selected for occupational exposures. Estimated HECs of 0.89 ppm and 3.75 ppm from the rat chronic toxicity/carcinogenicity study (increased incidence of salivary gland squamous cell metaplasia) were selected for long-term bystander and occupational exposures, respectively. For determining margins of exposure (MOEs), the USEPA compared acute-, short/intermediate-, and long-term occupational and bystander estimated inhalation exposures to these estimated HECs.

The USEPA reported the results of an extensive bystander and occupational risk assessment for inhalation exposures to iodomethane from its labeled use on fields. A range of MOEs and buffer zone distances were estimated in the risk assessment by analyzing a range of input factors. These factors included field si ze, application rate, emission rates from three different application types (flat fume, raised be d and drip irrigation), environmental factors at five different sites in California, Michigan, a nd Florida, and three toxicity endpoints (nasal lesions, fetal loss and neurotoxicity). Overall, the MOEs estimated for bystander exposure indicated that iodomethane exposures did not exceed USEPA = s level of concern at certain buffer zone distances. Occupational exposures and risks exceeded the USEPA = s level of concern for some workers (tractor drivers, copilots, tarp monitors and shovelers) when no respiratory protection is used. Consequently, an air purifying respirator, as well as loose fitting or well ventilated long-sleeved shirt and long pants, shoes plus socks, and a full-face shield are required on the labels for all workers. A five-day restricted entry interval after application was estimated to be adequate to not exceed the USEPA = s level of concern, even without respiratory protection. For this risk assessment, the USEPA considered a target MOE of 30-fold or greater to provide adequate bystander and worker protection. The 30-fold value is comprised of a 10-fold uncertainty factor to account for intra-species differences and a 3-fold uncertainty factor to account for pharmacodynamic differences between species (pharmacokinetic differences were accounted for in the PBPK modeling).

There are no chemical specific federal or State drinking water/groundwater standards forMs. Teresa McMullin 5.

iodomethane. Based on its chemical structure, iodomethane falls under the 5 microgram per liter New York State drinking water standard for A principal organic contaminants @ (10 NYCRR Part 5, Public Water Systems).

The available information on iodomethane and the Midas 7 end products indicates that they caused some toxicity following acute exposures in laboratory animals and are severe skin and eye irritants. In addition, iodomethane was shown to cause nasal degeneration, developmental/reproductive toxicity, neurotoxicity and thyroid perturbations leading to tumor development. Based on their modeled air impacts and estimated HECs, the USEPA determined that the proposed uses of these products should not pose significant risks to workers or the general public when used according to the strict provisions of the product labels. Despite the toxicity concerns and the need for extensive use requirements, iodomethane was federally registered (conditionally for a period of one year, to expire on October 5, 2008) as a potential replacement for methyl bromide.

The New York State Department of Health (NYSDOH) has concerns for the use of the

Midas 7 products. The directions for use of these products are extremely complicated and restrictive. The level of complexity and the use restrictions on the label ( e.g ., no use within a quarter of a mile of any occupied sensitive site, buffer zone calculations) could make it difficult to use these products in a manner that is compliant with the label. In addition, iodomethane poses several toxicity concerns and the four application methods listed on the product labels (raised bed-shank injection, raised bed-drip application, broadcast/flat fume-shank injection and auger probe-deep injection) allow for significant worker exposure potential to the active ingredient. Also, NYSDOH has concerns for expos ure to bystanders and nearby residents from both routine applications and mishaps associated with the application of these products. While the label restriction states not to use the products within a quarter of a mile of any occupied sensitive site ( e.g ., schools, daycare centers, nursing homes etc.), the labels do not require such a buffer zone for residential properties. Given the potential exposure of nearby residents, some of who may be children, pregnant women, elderly or those with preexisting medical conditions,

such a restriction seems warranted. This could be a particular problem if an accidental release were to occur as iodomethane is very volatile and hundreds of pounds of product are needed to treat even relatively small fields. Although NYSDOH did not review the properties of the coactive ingredient in the Midas 7 products, chloropicrin, they note that this compound has significant toxicity and irritant properties of its own, and has a very strong pungent odor. In addition, USEPA has registered these iodomethane products conditionally for a short term while it reviews soil fumigants categorically. Depending on the outcome of their evaluation, the registration status and/or restrictions on iodomethane products may change.

ENVIRONMENTAL FATE RISK ASSESSMENT : Iodomethane Technical (99.8% iodomethane) is labeled for formulation or repackaging purposes only.

The six end-use products contain various mixtures of iodomethane and chloropicrin (Chemical Code 081501) and are labeled for prep lant fumigations of fields intended forMs. Teresa McMullin 6.

commercial production of certain listed crops and field-grown ornamentals to control soil-borne pests including weed seeds, nematodes, insets and diseases. Chloropicrin is a component of products currently registered in the State for the preplant fumigation use pattern. All of the products are classified as restricted use pe sticides by the USEPA due to acute toxicity.

Midas 7 98:2 (97.8% iodomethane:2% chloropicrin), Midas 7 25:75 (24.95% iodomethane: 74.63 chloropicrin), Midas 7 33:67 (32.93% iodomethane 66.67% chloropicrin), Midas 7 50:50 (49.90% iodomethane:49.75% chloropicrin) are labeled for application via three preplant soil fumigation techniques: 1) raised bed soil fumigation for field-grown ornamentals, peppers, strawberries and tomatoes; 2) broadcast/flat fume soil fumigation for field-grown ornamentals peppers, strawberries, tomatoes, turf, stone fruits, tree nuts, vines (table, raisin and wine grapes) and nurseries; and 3) deep injection auger-probe for stone fruits, tree nuts, vines and field-grown

ornamental trees and shrubs.

Midas 7 EC Bronze (49.90% iodomethane:44.78% chloropicrin) and Midas EC Gold (32.93% iodomethane:61.69% chloropicrin) are labeled for preplant raised bed drip irrigation (chemigation) for field-grown ornamentals, peppers, strawberries and tomatoes.

Midas 7 98:2--One gallon contains 18.5 lbs iodomethane and 0.4 lbs chloropicrin and the maximum broadcast/flat fume application rate is 9.3 gallons/acre. The maximum application rate is 172 lbs iodomethane/acre. The maximum application rate for preplant deep injection auger-probe application is 450 lbs ai/a/day. There are no inerts.

Midas 7 25:75--One gallon contains 3.8 lbs iodomethane and 11 lbs chloropicrin and the maximum broadcast/flat fume application rate is 46.4 gallons/acre. The maximum application rate is 176 lbs iodomethane/acre. The maximum application rate for preplant deep injection auger-probe application is 118 lbs ai/a/day. There are no inerts.

Midas 7 33:67--One gallon contains 5 lbs iodomethane and 10.1 lbs chloropicrin and the maximum broadcast/flat fume application rate is 35.1 gallons/acre. The maximum application rate is 176 lbs iodomethane/acre. The maximum application rate for preplant deep injection auger-probe application is 152 lbs ai/a/day. There are no inerts.

Midas 7 50:50--One gallon contains 7.93 lbs iodomethane and 7.91 lbs chloropicrin and the maximum broadcast/flat fume application rate is 22 gallons/acre. The maximum application rate is 174 lbs iodomethane/acre. The maximum application rate for preplant deep injection auger-probe application is 172 lbs ai/a/day. There are no inerts.

Midas 7 EC Bronze--One gallon contains 7.93 lbs iodomethane and 7.12 lbs chloropicrin and the maximum raised bed drip irrigation (chemigation) application rate is 22 gallons/acre. The maximum application rate is 174 lbs iodomethane/acre. The inert is not a solvent carrier.

Midas 7 EC Gold--One gallon contains 5 lbs iodomethane and 9.31 lbs chloropicrin and the maximum raised bed drip irrigation (chemigation) application rate is 35.1 gallons/acre. The maximum application rate is 176 lbs iodomethane/acre. The inert is not a solvent carrier.Ms. Teresa McMullin 7.

Solubility: The solubility of iodomethane is 1,420 mg/l.

Hydrolysis: (MRID 45593705) In a study that USEPA found to be acceptable, the half-life in pH 7 buffer at 25 degrees was 93.67 days with methanol as the major transformation product. At pH 4, the half-life was 105 days, and at pH 9 it was 108 days.

Soil Photolysis: (MRID 45593706) In a study that USEPA found supplemental and upgradable, the half-life in a radiated soil was determined to be approximately 11.5 days. Methanol and fomaldehyde were major transformation products.

Aqueous Photolysis: (MRID 46332701) Sufficient information was submitted, so together with MRID 45593706 (not submitted), USEPA found the studies to be acceptable. The half-life

is 13 days (taken from the September 17, 2003 USEPA memorandum on the review of environmental fate data).

Aerobic Soil Metabolism: (MRID 455937070) In a study that USEPA found acceptable, the half-life in a sandy loam soil (pH 6.5, %OC 1.48) was 2.1 hours. USEPA indicated that the rapid

half-life was due to volatilization rather than microbial degradation. However, carbon dioxide was detected, so some degree of microbial degradation did take place.

Anaerobic Aquatic Metabolism: (MRID 45593708) In a 14-day study that USEPA found acceptable using a sandy clay loam (pH 8.0, 2.8% OM)/water system (pH 7.94), the half-life in the entire system was 40.2 hours, in the water was 38.8 hours and in the sediment 38.1. No major degradates were found.

Adsorption/Desorption: (MRID 45593709; no DER submitted) (MRID 46332702) USEPA found this study to be supplemental. %OC ranged from 1.02 to 4.3 and the pH ranged from

6.2 to 7.9.

Soil Type %OC Soil pH Adsorption

Koc Desorption

Koc

Swiss NA NA 28 144

California NA NA 61 317

Ohio NA NA 27 67

German NA NA 14 74

Oregon NA NA 43 134
Terrestrial Field Dissipation: (MRID 45593711) USEPA found this study acceptable. In a fine loamy sand (pH 6.4, %OM 2.25), the half-life was 4.8. In a sandy loam (pH 7.0, %OM 2.02), the half-life was 5.0 days. No major transformation products were found.Ms. Teresa McMullin 8.

Modeling: Staff modeled iodomethane on Riverhead soil using a K

oc of 34.8, a half-life of 5 days and the maximum application rate of 176 lbs ai/a/year. The model projected two peaks, one at about 110 ppb and one at just over 200 ppb. Modeling half the application rate resulted in two peaks, one at about 50 ppb, one at about 90 ppb. No major transformation products were found in either the aerobic metabolism or the terrestrial field dissipation study, so there were no degradates to model.

Groundwater Review Summary: Modeling the raised bed or broadcast/flat fume application rates for the end-use products projected two large peaks of leachate.

The last two sentences in the Environmenta l Risks Conclusions (Page 3 of 37) of the Environmental Fate and Ecological Risk Assessment for the Registration of Iodomethane (undated) state:

A However, since this compound is very soluble in water, there is the possibility of leaching to groundwater, if slicing or removal of the tarpaulin coincides with, or is followed soon by, a rain event. EFED recommends adding cautionary language to the label to prohibit the slicing or removal of the tarpaulin if it is raining or if rain is expected

within 48 hours. @

This cautionary language does not appear on any of the end-use product labels. With a terrestrial dissipation (tarp-covered) half-life of 5 days, removal of the tarp shortly after 5 days would leave half the applied product available to leach. Should a rain event coincide with tarp removal, significant leaching would be possible. Therefore, Engineering Geology staff questions the absence of this cautionary text on the end-use products = labeling.

In addition, prior to making a final determination on the impact to groundwater for the products bearing the Preplant Deep Injection Auger-Probe Application method, staff have the following questions:

1. For the Preplant Deep Injection Auger-Probe Applications on Midas 7 98:2, Midas 7 25.75,

Midas 7 33:67, and Midas 7 50:50 labels, the labels all state, under the section PROCEDURES PRIOR TO, DURING AND AFTER ALL APPLICATIONS that

A During All Applications : $ Immediately cover treated areas with a plastic tarpaulin for a minimum of 5 days. @ Please describe the type of tarpaulin that will be used around the

trees.

2. For Midas 7 98:2, staff calculated the application rate for Preplant Deep Injection AugerProbe Application to be 450 lbs iodomethane/a/day, because the label states that you can treat 230 trees per acre per day at 2 lbs product per tree. Please clarify that this is the correct application rate.

3. For all of the products, what is the maximum number of trees that might be expected toMs. Teresa McMullin 9.

be treated per acre? Our calculations indicat ed that at a spacing of 10 feet on center, there could be 432 trees per acre. Are trees ever planted closer than a 10 foot grid pattern?

Until these questions are answered, there is not enough information in the application package to determine impact to groundwater.

TECHNICAL ISSUES SUMMARY : There are human health concerns for the use of the

Midas 7 products due to the level of complexity of the use directions and potential for exposure to bystanders and nearby residents from both routine applications and mishaps associated with the application of these products. While the product labels restrict use of the products within a quarter of a mile of any occupied sensitive site ( e.g ., schools, daycare centers, nursing homes etc.), the labels do not require such a buffer zone for residential properties. Given the potential exposure of nearby residents, some of who may be children, pregnant women, elderly or those with preexisting medical conditions, such a restriction seems warranted. This could be a particular problem if an accidental release were to occur as iodomethane is very volatile and hundreds of pounds of product are needed to treat even relatively small fields.

Based on the environmental fate data, LEACHP simulations, and lack of cautionary label text prohibiting the slicing or removal of the tarpaulin if it is raining or if rain is expected within 48 hours, the potential for iodomethane to impact groundwater/drinking water resources in

New York State cannot be discounted.

Furthermore, there are questions regarding the need for iodomethane use in the State. According to data obtained from the New Yo rk State Pesticide Sales and Use Reporting database, fumigants, including methyl bromide, are not widely used in the State. Although iodomethane may have some global benefit as a methyl bromide replacement, the risks associated with its use in New York State appear to outweigh the potential benefits.

The Department accepts your request for withdrawal of the applications to register

Iodomethane Technical and six end-use Midas 7 products.

Please note that Arysta may resubmit applications to register the subject products. The applications must be accompanied by new application fees, meet the additional application requirements for products containing a new ac tive ingredient listed in 6 NYCRR Part 326.16, and address the human health and environmental fate questions/issues noted above.

You are reminded that any unregistered pesticide product may not be sold, offered for sale, distributed, or used in New York State.Ms. Teresa McMullin 10.

Please contact our Pesticide Product Regist ration Section, at (518) 402-8768, if you have any questions.

Sincerely,

Maureen P. Serafini

Maureen P. Serafini

Director Bureau of Pesticides Management

ecc: A. Grey/E. Horn, NYS Dept. of Health R. Mungari, NYS Dept. of Ag. & Markets W. Smith, Cornell University, PSUR