October 11, VIA UPS (8033) Mr. John Riley Nippon Soda Co., Ltd. c/o Nisso America Inc. 88 Pine St., 14 th Floor. New York, New York 10005

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1 New York State Department of Environmental Conservation Division of Materials Management Bureau of Pest Management Product Registration & Pest Management Alternatives Section 625 Broadway, Albany, New York Phone: (518) Fax: (518) Website: Joe Martens Commissioner October 11, 2013 VIA UPS (8033) Mr. John Riley Nippon Soda Co., Ltd. c/o Nisso America Inc. 88 Pine St., 14 th Floor. New York, New York Dear Mr. Riley: Re: Registration of the New Active Ingredient Cyflufenamid as Contained in Cyflufenamid Technical Fungicide (EPA Reg. No ), Miltrex 10 SC Fungicide (EPA Reg. No ), and Cyflufenamid 10 SC Fungicide (EPA Reg. No ) (Chemical Code ) The New York State Department of Environmental Conservation (Department) has reviewed the new application, received October 31, 2012, and the additional information, received January 18, 2013, and June 28, 2013, from Nippon Soda Co., in care of Nisso America Inc., to register the new active ingredient cyflufenamid as contained in the above-referenced pesticide products. Cyflufenamid is a fungicide proposed for the control of powdery mildew. The application package was deemed complete for purposes of technical review on March 5, Pursuant to the review time frame specified in Environmental Conservation Law (ECL) , a registration decision date of August 2, 2013 had been established. The registrant was notified on June 20, 2013 regarding some concerns that were identified during the technical review process. Additional information was received June 28, The registration decision date was waived by the registrant in order to allow for adequate time to review this additional information. Cyflufenamid Technical Fungicide (EPA Reg. No ) is labeled for manufacturing use only. Miltrex 10 SC Fungicide (EPA Reg. No ) contains 0.85 lb of the active ingredient per gallon in a suspension concentrate and is labeled for use on cucurbits, grapes, pome fruits, and strawberries and other low growing berries. Cyflufenamid 10 SC Fungicide (EPA Reg. No ) contains 0.85 lb of the active ingredient per gallon in a suspension concentrate and is labeled for use on outdoor landscape and outdoor nursery ornamentals. For both of these commercial products, the application rates range from fl oz ( lb ai) per acre dependent on crop type. The label allows for two sequential applications a year not to exceed the maximum seasonal application of lb ai per acre.

2 Mr. John Riley 2. The Department and the New York State Department of Health evaluated the application and all supporting documents submitted to date regarding human health, fish and wildlife resources, and ground and surface water resources of New York State. After careful consideration of all information, the Department has concluded that the use of the cyflufenamid products should not have an adverse effect on the health of applicators or the general public, the fish and wildlife resources, or the ground and surface water of New York State when used as labeled. Please see the full assessments from the New York State Department of Health and this Department in the Appendix to this letter. The Department hereby accepts the registration of the new active ingredient, cyflufenamid, as contained in Cyflufenamid Technical Fungicide (EPA Reg. No ), Miltrex 10 SC Fungicide (EPA Reg. No ), and Cyflufenamid 10 SC Fungicide (EPA Reg. No ) for registration as labeled in New York State. Enclosed for your files are the Certificate of Pesticide Registration and New York State stamped Accepted labeling for the three products. Please note, a proposal Nippon Soda Co., or any registrant to register a product containing cyflufenamid whose labeled uses are likely to increase the potential for significant exposure to humans, nontarget organisms, or the environment, would constitute a major change in labeled use pattern. Such an application must be accompanied by a new application fee and meet the requirements specified in 6NYCRR Part Please contact, Jeanine Broughel, Chief of the Product Registration and Pest Management Alternatives Section, at (518) , if you have any questions. Enclosures Sincerely, Jeanine M. Broughel for Scott Menrath, P.E. Director Bureau of Pest Management

3 Mr. John Riley 3. HUMAN HEALTH RISK ASSESSMENT APPENDIX The New York State Department of Health (NYSDOH) reviewed the data, submitted by Nippon Soda Co. (c/o Nisso American Inc.) in support of the registration of new active ingredient cyflufenamid. The NYSDOH stated that neither cyflufenamid nor the formulated products Cyflufenamid 10 SC/Miltrex 10 SC was very toxic in acute oral, dermal or inhalation exposure studies in laboratory animals. In addition, the active ingredient and the formulated products were not irritating to the skin or eyes (tested on rabbits) or dermal sensitizers (tested on guinea pigs). Cyflufenamid caused some toxicity in chronic feeding studies in mice and rats, but not dogs. In a one-year dog feeding study, cyflufenamid did not cause any toxicity up to doses of milligrams per kilogram body weight per day (mg/kg/day) in males and mg/kg/day in females. In a chronic feeding/oncogenicity study in mice, premature deaths attributed to fatty changes in the liver, heart and kidney were reported at doses of 325 mg/kg/day in males and 404 mg/kg/day in females; the no-observed-effect levels (NOELs) were 63 mg/kg/day in males and 76 mg/kg/day in females. In a chronic feeding/oncogenicity study in rats, cyflufenamid caused decreased body weight gain in both sexes, increased thyroid/parathyroid/liver weights and centrilobular hepatocytic hypertrophy in females, as well as hyaline droplets and cortical hemorrhagic degeneration of adrenals in males at doses of 22 mg/kg/day in males and 28 mg/kg/day in females; the respective NOELs were 4.4 mg/kg/day and 5.5 mg/kg/day. The U.S. Environmental Protection Agency (U.S. EPA) Office of Pesticide Programs calculated an oral reference dose (RfD) of mg/kg/day for cyflufenamid based on a NOEL of 4.4 mg/kg/day in the chronic feeding/oncogenicity study in rats and an uncertainty factor of 100. This RfD has not yet been adopted by the U.S. EPA s Integrated Risk Information System (IRIS). A current search of the toxicological literature did not find any significant information on the toxicity of cyflufenamid. Cyflufenamid caused some developmental toxicity in the offspring of pregnant rabbits, but not pregnant rats, exposed to this chemical during organogenesis at doses that also caused maternal toxicity. In the rabbit study, decreased fetal weight and incomplete ossification (cervical vertebrae, epiphyses, metacarpals and phalanges) were reported in offspring at a dose of 60 mg/kg/day; the NOEL was 10 mg/kg/day. Maternal toxicity consisted of decreased body weight gain and food consumption at a dose of 10 mg/kg/day; the NOEL was 5 mg/kg/day. In the rat study, no treatment-related effects were observed in offspring at maternal doses up to 1,000 mg/kg/day, the highest dose tested. Maternal toxicity consisted of increased liver weight and indicators of deteriorating health (brown staining of anterior region coat, piloerection and ungroomed appearance) at a dose of 1,000 mg/kg/day; the NOEL was 300 mg/kg/day. In a multigeneration reproduction study in rats, cyflufenamid was associated with reduced body weight gain in both F1 and F2 offspring at doses of 57.4 mg/kg/day in males and 66.2 mg/kg/day in females; the respective NOELs were 18 mg/kg/day and 19.9 mg/kg/day. Parental toxicity consisted of increased liver and thyroid weights at doses of 57.4 mg/kg/day in males and 66.2 mg/kg/day in females; the respective NOELs were 18 mg/kg/day and 19.9 mg/kg/day. Cyflufenamid caused tumors in rats and mice in chronic feeding studies. In rats, there was a treatment-related increase in thyroid follicular cell tumors in males compared to controls. In mice, there was an increase in liver tumors in males of the highest dose group (17/50) when

4 Mr. John Riley 4. compared to controls (6/50). Cyflufenamid was negative in a number of genotoxicity studies. Based on these data, the U.S. EPA classified cyflufenamid as likely to be carcinogenic to humans. To evaluate cancer risks, the U.S. EPA derived a cancer potency factor (CPF) of 6.1 x 10-3 (mg/kg/day) -1, based on the increased incidence of combined benign and malignant liver tumors in male mice. The U.S. EPA established tolerances for cyflufenamid residues in or on the following commodities: 0.1 parts per million (ppm) for apple (wet pomace), 0.2 ppm for low growing berries, 0.06 ppm for pome fruit, 0.15 ppm for small vine-climbing fruit, 0.3 ppm for raisins, and 0.07 ppm for cucurbit vegetables (Federal Register 77: 38,204 38,210, June 27, 2012). The chronic population adjusted dose (cpad) for cyflufenamid is mg/kg/day and has the same basis as the RfD. The U.S. EPA estimated that the chronic dietary exposure to cyflufenamid residues from all crops for which there are tolerances, and from drinking water, would be one percent or less of the cpad for the general U.S. population and all population subgroups. Additionally, the cancer risk for the general U.S. population from exposure to cyflufenamid from drinking water and all registered crop uses was estimated to be 9.5 x These exposure analyses are based on the assumption that 100 percent of crops are treated and contain tolerance level residues. Actual residues and resulting exposure levels are expected to be less than these assessments estimate. The U.S. EPA reported the results of an occupational risk assessment for short- (1 30 days)/intermediate-term (1 6 months) inhalation exposures to cyflufenamid from use on labeled commodities (cucurbits, pome fruit, grapes, strawberries, and nursery/ornamentals) via several application methods (aerial, ground boom, air blast, backpack and low-pressure handwand). Dermal risks were not assessed because a toxicity endpoint for cyflufenamid was not identified for this route of exposure. For determining margins of exposure (MOEs), the U.S. EPA compared estimated short-/intermediate-term inhalation exposures to a NOEL of 5 mg/kg/day from the developmental toxicity study in the rabbit. For mixer/loaders and applicators of cyflufenamid, inhalation MOEs were estimated to range from 38,000 to 330,000 and 88,000 to 670,000, respectively, depending on the application method (aerial, groundboom or airblast) and commodity (cucurbits, pome fruit, grapes or strawberries). The MOEs for flaggers supporting aerial applications ranged from 130,000 to 260,000 depending on the commodity. The MOE for mixers/loaders/applicators of cyflufenamid to nursery/ornamentals via backpack sprayer or lowpressure handwand sprayer was 260,000. The U.S. EPA additionally estimated lifetime cancer risks for workers using the CPF of 6.1 x 10-3 (mg/kg/day) -1 and assuming exposure to cyflufenamid for 30 days per year over a 70-year lifetime. The lifetime cancer risk for mixers/loaders and applicators were estimated to range from 5.9 x 10-8 to 1.3 x 10-7 and 9.9 x 10-9 to 1.1 x 10-7, respectively, depending on the application method and commodity. The estimated lifetime cancer risks for mixers/loaders/applicators, using the same assumptions as above, applying cyflufenamid via backpack sprayer and low-pressure handwand sprayer were 5.8 x 10-8 and 1.4 x 10-8, respectively. These estimates assumed that workers wore long-sleeved shirt and pants, shoes plus socks and chemical-resistant gloves as per label requirements. The U.S. EPA additionally estimated lifetime cancer risks for worker exposures to cyflufenamid via a variety of post-application activities (e.g., harvesting, thinning, scouting, weeding). The estimated cancer risks for workers, assuming a 12-hour post-application restricted entry interval (REI), ranged from 9.2 x 10-8 to 1.8 x 10-6, depending on the commodity and activity. The U.S. EPA did not estimate non-cancer post-application risks to workers because an endpoint for dermal toxicity was not identified and inhalation exposures are not expected.

5 Mr. John Riley 5. Overall, non-cancer MOEs and estimated cancer risks were within the range considered acceptable by the U.S. EPA to provide adequate worker protection. There are no chemical specific federal or New York State drinking water/groundwater standards for cyflufenamid or its degradates. Based on their chemical structure, these chemicals fall under the 50 microgram per liter (µg/l) New York State drinking water standard for unspecified organic contaminants (10 NYCRR Part 5, Public Water Systems). The New York State drinking water standard for the sum of unspecified organic contaminants and principal organic contaminants is 100 µg/l. If one uses the U.S. EPA derived CPF (6.1 x 10-3 (mg/kg/day) -1 ) and procedures for deriving ambient water quality standards and guidelines based on oncogenic effects (6 NYCRR Part 702.4), the value that is associated with a one-in-a-million increased lifetime cancer risk is 5.7 µg/l. The available information indicates that neither cyflufenamid nor the formulated product Miltrex 10 SC/Cyflufenamid 10 SC was very acutely toxic or irritating to the eyes and skin. Cyflufenamid caused some toxicity in chronic and developmental/reproductive animal studies, as well as increased incidences of thyroid follicular cell tumors in male rats and liver tumors in male mice. It has been classified by the U.S. EPA as likely to be carcinogenic to humans and the testing results for cyflufenamid meet the definition of an oncogen in 6 NYCRR Part Although the estimated non-cancer and cancer risks to workers and the public (via dietary exposures) are within the range that is generally considered to be acceptable, the NYSDOH had concerns for registering a pesticide product for food crops if it has oncogenic properties unless either the needs for the product are significant or it replaces products that pose greater risk. In response to the NYSDOH s concerns, the registrant submitted a carcinogenic potency and use rate comparison of cyflufenamid to five alternative fungicide active ingredients (tetraconazole, kresoxim-methyl, fluopyram, chlorothalonil, and thiophanate-methyl) which are registered in the state for the control of powdery mildew on apples, grapes, cucurbits and/or strawberries. All six active ingredients are classified by the U.S. EPA as likely to be carcinogenic to humans and have available U.S. EPA derived cancer slope factors (CSF), except for chlorothalonil. In regards to carcinogenic potency, cyflufenamid had the lowest CSF value ( (mg/kg/d -1 )), aside from chlorothalonil for which a CSF was not derived (the U.S. EPA used a margin-of-exposure approach to quantify cancer and non-cancer risks from exposure). Cyflufenamid also had the lowest use rate for food crops of the six active ingredients (20 grams per acre per season). In addition, the registrant also included a discussion of the need and/or benefit for cyflufenamid to control the fungal infection, powdery mildew, which affects the economically important crops grapes, apples and strawberries. The registrant stated that powdery mildew has developed resistance to other fungicides (with different modes of action) currently used in the state and cited the 2013 Crop and Pest Management Guidelines produced by Cornell Cooperative Extension as their reference. The NYSDOH independently reviewed the 2013 Guidelines which state that powdery mildew has demonstrated resistance to the strobilurin fungicides (azoxystrobin, thiophanate-methyl, kresoxim-methyl) and demethylation inhibitor fungicides (difenoconazole, triflumizole, myclobutanil) in a majority of vineyards and orchards in New York State. The Guidelines recommend either not using these fungicides at all to treat powdery mildew or limited use in rotational programs.

6 Mr. John Riley 6. Since cyflufenamid has a different mode of action than the other fungicides registered in New York State, it would provide an alternate fungicidal mechanism to the triazoles and strobilurins as there are known instances of resistance to these fungicide types. Also, the ability to alternate classes of fungicides throughout the use season is crucial to resistance management. It also has a lower cancer slope factor than other fungicides registered in New York State and a low use rate for food crops. Even though the NYSDOH voiced concerns with registering a product for food crops if it has oncogenic properties, the registration of cyflufenamid offers many benefits. Also, New York State farmers would be at a competitive disadvantage to farmers in other states that have cyflufenamid registered and available to use in a rotational program. After consideration of the reasons listed above, the NYSDOH removed their objection of the registration of cyflufenamid. Therefore, there were no objections of registration of cyflufenamid as labeled for the three products in New York State. ECOLOGICAL RISK ASSESSMENT The Department s Division of Fish, Wildlife and Marine Resources Bureau of Habitat (BOH) reviewed the information submitted in support of the registration of the new active ingredient cyflufenamid. The following is the BOH s review: Use Profile - Miltrex 10 SC Fungicide contains is labeled For Agricultural Use Only. Applications of fluid ounces, ( lbs ai) per acre are made at 7 to 14 day intervals. No more than 2 applications or lbs. ai may be made per year. Labeled crops, or crop groups, include several with significant NY acreage including: Cucurbit Vegetables, Grapes, Pome Fruit, and Strawberries and Other Low Growing Berries. Cyflufenamid 10 SC Fungicide is labeled for use on outdoor landscape and outdoor nursery ornamentals. Application rates and limits are the same as those for Miltrex 10 SC. Reapplication intervals are slightly longer being days. The label identifies 66 different plants which may be treated ranging from herbaceous annuals to large trees (e.g. willow, oak). Chemical Description & Mode of Action - Both end use products contain 10% cyflufenamid, (Z)-N-(α-cyclopropylmethoxyimino-2,3-difluoro-6-trifluoromethylbenzyl)-2-phenylacetamide, a new active ingredient for powdery mildew control in the amidoxime chemical class. The cyflufenamid specific biochemical mode of action is not known, the applicant suggests that the mechanism is different from existing fungicides and that it may interfere with multiple fungal life stages. Cyflufenamid has a water solubility of 0.52 mg/l. Its octanol/water partition coefficient, K OW, is 50,119. soil partitioning coefficients, K OC s, range from ml/g with a geometric mean of Cyflufenamid vapor pressure is 2.7x10-7 mm Hg; volatilization will not contribute significantly to dissipation. Toxicity & Environmental Fate - Cyflufenamid is practically non-toxic to birds and mammals on an acute basis. Terrestrial vertebrate chronic toxicity thresholds are several orders of magnitude higher than exposures estimated from labeled use. Cyflufenamid is moderately to highly toxic to fish and aquatic invertebrates.

7 Mr. John Riley 7. Cyflufenamid is moderately persistent to persistent post application. Dissipation will occur primarily via aerobic microbial metabolism. It is stable to hydrolysis and photolysis. Aerobic soil metabolism half lives, T 1/2, were 19 and 21 days in U.S. soils but ranged from 7.1 to 122 days, geometric mean = 23 days, in U.K. and German soils. T 1/2s in anaerobic water/sediment system tests were 131, 693, and 408 days in water, sediment, and total system, respectively. Terrestrial field dissipation T 1/2s were 3.1, 2.5, and 15.8 days in California, Georgia, and NY State, respectively. Neither the parent compound nor any of the four major cyflufenamid metabolites were detected below the 0-15cm soil layer during the 454 day monitoring period. Exposure Modeling & Risk Assessment - Standard BOH screening level exposure modeling was conducted for both aquatic and terrestrial non-target resources. No toxicity thresholds were exceeded at the screening level so additional refined modeling was not conducted. Two of the four major cyflufenamid metabolites 149-F1 and 149-F6 are more persistent and have higher water solubility than the parent compound. Both are less toxic at least to freshwater test species and are produced in low amounts but they will tend to accumulate over time in use areas. The metabolite 149-F6 in particular, with its aerobic soil metabolism T 1/2s ranging between 866 and 2310 days and water solubility of 9 grams/l, will likely build in aquatic systems in use areas. While not of immediate ecological concern there is no way of knowing what its effect may be in combination with other compounds and their metabolites. When used as labeled and evaluated as if it were the only stressor, cyflufenamid isn t likely to result in adverse impacts to non-target organisms. The low application rate and limit of two applications a year provide a fairly large margin of safety for non-target resources. ENVIRONMENTAL FATE AND GROUNDWATER IMPACTS: The Department s groundwater staff reviewed the information submitted in support of the registration of the new active ingredient cyflufenamid. The following is the groundwater staff s review: All environmental fate findings used for this technical review were obtained from USEPA Data Evaluation Records (DER) which are referenced in the sections below using the corresponding Master Record Identification (MRID) numbers. Label Statement - The USEPA stamped master labels for Miltrex 10 SC and Cyflufenamid 10 SC have surface water advisories in their Environmental Hazards statements. Major Transformation Products 149-F N-cyclopropylmethoxy-2,3-difluoro-6-trifluoromethylbenzamidine 149-F1 2,3-difluoro-6-trifluoromethylbenzamidine 149-F11 (Z)-N-(α-Cyclopropylmethoxyimino-2,3-difluoro-6-trifluoromethylbenzyl)- carbamoylacetic acid Water Solubility-MRIDs , , , and : From supplemental studies, Table 1 lists the water solubilities at 20 C/68 F of cyflufenamid and its major (greater than or equal to 10% of the initially applied parent compound) degradation products.

8 Mr. John Riley 8. Table 1: Water Solubilities of Cyflufenamid and Major Degradates Compound Cyflufenamid 149-F F 149-F1 149-F6 Water Solubility 0.52 mg/l g/l g/l g/l g/l MRID Number Hydrolysis - MRID : In a supplemental study, it was noted that cyflufenamid is hydrolytically stable at ph 4, 5, and 7. It was reported that there was hydrolytic activity at ph 9 at varying temperatures and the only major degradate formed was 149-F. A ph of 9 is not representative of actual environmental conditions. Aqueous Photolysis - MRID : In a supplemental study, it was shown that the environmental phototransformation half-life of cyflufenamid in water is ca. 220 days with no major degradation products. Soil Photolysis - MRID : In a supplemental study using a sandy soil from the United Kingdom (ph 6.4, organic matter 3.44 %), it was shown that the environmental phototransformation half-life of cyflufenamid in soil is ca. 171 days with no major degradation products. Aerobic Biotransformation of Cyflufenamid in Soils MRIDs , , , : Table 2 lists the percent recoveries of the major cyflufenamid degradation products from the aerobic soil biotransformation studies. The maximum values will be used for determining application rates for LEACHP modeling. Study Acceptability / / / / Table 2: Aerobic Biotransformation of Cyflufenamid in Soil Observed Soil Type ph %OC DT50 (Days) California sandy ca. 20 Mississippi clay ca. 20 U.K. Arrow sandy ca. 8 U.K. Evesham 3 clay ca. 20 U.K. Bromsgrove sandy Germany Speyer sandy ca. 9 Major Degradate Percent of Initial Applied 149-F F F F F F F F F F F ca F 11.4 U.K. Arrow sandy ca F F F Aerobic Biotransformation of Degradates in Soils MRIDs , , , : Tables 3, 4 and 5 list the half-lives (DT50) of the degradates from the aerobic

9 Mr. John Riley 9. biotransformation studies and the values in bold type will be used for LEACHP modeling since this soil type more closely resembles Long Island soil in ph and percent organic carbon (%OC). Study Acceptability / Study Acceptability / Study Acceptability / Table 3: Aerobic Biotransformation of 149-F11 in Soils Soil Type ph.5 %OC Observed DT50 (Days) U.K. Arrow sandy ca. 2 U.K. Bromsgrove sandy ca. 3 U.K. Evesham 3 clay ca. 2.5 Table 4: Aerobic Biotransformation of Degradate 149-F in Soils Soil Type ph %OC Observed DT50 (Days) U.K. Arrow sandy ca. 10 U.K. Bromsgrove sandy ca. 5 U.K. Evesham 3 clay ca. 16 Table 5: Aerobic Biotransformation of Degradate 149-F1 in Soils Soil Type ph %OC Observed DT50 (Days) U.K. Arrow sandy >120 U.K. Bromsgrove sandy >120 U.K. Evesham 3 clay >120 Anaerobic Biotransformation In Soil - MRID , : In a supplemental study and an acceptable study ( and , respectively), it was shown that cyflufenamid was stable under anaerobic conditions with the study half-lives >120 days. Adsorption/Desorption of Cyflufenamid in Soils MRID : Table 6 lists the average adsorption KOC values for the parent molecule in various soil types. These KOC values range from 1934 to 3087 indicating that cyflufenamid has a high affinity for adsorption onto soil particles and will probably not leach to groundwater. The U.K. Bromsgrove sandy has a ph and %OC that closely resembles Riverhead soils (ph 5.5 and percent organic carbon 1%) and that KOC is Cyflufenamid will not be modeled. Study Acceptability / Table 6: Adsorption/Desorption of Cyflufenamid in Soil Water-Soil Type ph %OC U.K. Arrow sandy U.K. Bromsgrove sandy U.K. Evesham 3 clay Germany Speyer 2.2 y sand Adsorption K OC Desorption K OC

10 Mr. John Riley 10. Adsorption/Desorption of Degradates in Soil MRID , , : Tables 7, 8 and 9 list the cyflufenamid degradates and their KOC values, which are one to two orders of magnitude below the parent molecule indicating that they would be much more mobile in soil. These KOC values ranged from 7 (149-F11) to 213 (149-F1). As was noted before, the U.K. Bromsgrove sandy has a ph and %OC that more closely resembles Riverhead soil so those KOC values (bolded type) will be used in LEACHP modeling. Study Acceptability / Table 7: Adsorption/Desorption of Degradate 149-F11 in Soils Water-Soil Type ph %OC U.K. Arrow sandy U.K. Bromsgrove sandy U.K. Evesham 3 clay Germany Speyer sandy Adsorption K OC Desorption K OC Study Acceptability / Table 8: Adsorption/Desorption of Degradate 149-F in Soils Water-Soil Type ph %OC U.K. Arrow sandy U.K. Bromsgrove sandy U.K. Evesham 3 clay Germany Speyer sandy Adsorption K OC Desorption K OC Study Acceptability / Table 9: Adsorption/Desorption of Degradate 149-F1 in Soils Water-Soil Type ph %OC U.K. Arrow sandy U.K. Bromsgrove sandy U.K. Evesham 3 clay Germany Speyer sandy Adsorption K OC Desorption K OC Terrestrial Field Dissipation of Cyflufenamid MRID : This study was classified as

11 Mr. John Riley 11. upgradable field dissipation study of cyflufenamid, performed under U.S. field conditions at three sites: one a plot of sandy -y sand from Porterville, California; another a plot of sand soil from Chula, Georgia; and the last in a plot of soil from North Rose, New York State (Wayne County, DEC Region 8). All experiments were at a 0-15 cm depth. Cyflufenamid was broadcast four times at seven day intervals at an equivalent target application rate of lb a.i. per acre per application to represent a worst-case scenario for maximum active ingredient loading at a total of lb ai (twice the maximum labeled amount). Total water input (precipitation plus irrigation) during the study period was 791%, 157% and 144% of the 10-year historical average for the California, Georgia and New York sites, respectively. Table 10 lists the active ingredient half-lives from the field dissipation studies: MRID Number/ Acceptability MRID Upgradeable Table 10: Half- Lives of Cyflufenamid from Field Dissipation Studies. Location/Soil Type ph %OC DT50 (Days) Porterville,California/ sandy-y sand (0-90 cm) Chula, Georgia/sand (0-30 cm) over y sand-sandy (60-90 cm) North Rose, New York/ (0-15 cm) over silt (15-75 cm) over clay ( Dissipation Route Transformati on Transformati on Transformati on Degradates Detected 149-F F6 149-F 149-F1 149-F F 149-F1 149-F 149-F1 cm) Samples were collected at 15 cm depth intervals (0-15, 15-30, 30-45) and neither cyflufenamid nor any degradate was detected below 15 cm. The limit of detection (LOD) was reported to be at 0.7 ppb and the limit of quantification (LOQ) was 2.0 ppb (3 x LOD). LEACHP Modeling of Cyflufenamid and Degradates: Table 11 lists the parameters that will be used for LEACHP modeling. Table 11: Values Used for LEACHP Modeling Molecule Application Rate Solubility K OC t½ % of Initial (lbs ai/acre/season) (mg/l) (ml/g) (Days) Applied 149-F F F , The following equation was used for determining the application rates of the degradates:.. max %

12 Mr. John Riley 12. Discussion: The modeling the leaching profiles of the three major cyflufenamid degradates, showed that degradate 149-F11 leached at a maximum of 4.0E-06 ppb, 149-F at a maximum of 1.6E-05 ppb, and 149-F1 at 1.8E-04. Therefore, due to the low degradate leaching levels projected from the LEACHP modeling, staff do not object to the registration of cyflufenamid