February 11, Ms. Judy Fersch BASF Corporation PO Box Research Triangle Park, NC Dear Ms. Fersch:

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1 New York State Department of Environmental Conservation Division of Materials Management Bureau of Pest Management Pesticide Product Registration Section 625 Broadway, Albany, New York Phone: (518) Fax: (518) Website: Joe Martens Commissioner February 11, 2015 Ms. Judy Fersch BASF Corporation PO Box Research Triangle Park, NC Dear Ms. Fersch: Re: Registration of Merivon Xemium Brand Fungicide and Priaxor Xemium Brand Fungicide Containing the New Active Ingredient Fluxapyroxad (Chemical Code ) The New York State Department of Environmental Conservation (Department) has evaluated your application, received July 1, 2013, and supplemental materials received to date in support of the registration of the above-referenced pesticide products. Merivon Xemium Brand Fungicide (Merivon) contains 21.26% of the active ingredients fluxapyroxad and pyraclostrobin and is formulated as a suspension concentrate. Merivon is labeled to control various fungal diseases in pome fruit and stone fruit via ground, aerial, or chemigation methods. The maximum application rates are 6.7 fluid ounces of product (0.11 lbs fluxapyroxad) per acre per application and 22 fluid ounces of product (0.36 pounds fluxapyroxad) per acre per year. Subsequent to the technical review process, BASF Corporation (BASF) submitted additional proposed labeling for Merivon. This labeling proposed the addition of the crop groups bulb vegetables, cucurbit vegetables, leafy vegetables, root vegetables, strawberries and tree nuts. The maximum yearly application rate for several of the crop groups (bulb vegetables, leafy vegetables and strawberries) is higher than the rate reviewed during this technical review (0.54 pounds of fluxapyroxad per acre per year versus 0.36 pounds of fluxapyroxad per acre per year). Please see the Registration Summary section for a further discussion of the increased application rates. Priaxor Xemium Brand Fungicide (Priaxor) contains 14.33% fluxapyroxad and 28.58% pyraclostrobin and is formulated as a suspension concentrate. Priaxor is labeled to control various fungal diseases in barley, corn, dried shelled peas and beans, edible-podded legume

2 Ms. Judy Fersch 2 vegetables, fruiting vegetables, oats, oilseed crops, peanut, rye, soybean, succulent shelled peas and beans, sugar beet, tuberous and corm vegetables, triticale and wheat. Labeled application methods include ground, aerial, and chemigation. The maximum application rates are 8 fluid ounces of product (0.09 pounds of fluxapyroxad) per acre per application and 24 fluid ounces of product (0.26 pounds of fluxapyroxad) per acre per year. This application is not a major change in labeling for the active ingredient pyraclostrobin as the use sites and rates listed on the labeling have previously been approved by the Department. The application package was deemed complete for purposes of technical review on November 14, Pursuant to the review time frame specified in Environmental Conservation Law , a registration decision date of April 11, 2014 was established. REGISTRATION SUMMARY Technical reviews of the proposed uses included on the Merivon and Priaxor labels have been performed by the Department and the New York State Department of Health. These reviews encompassed the expected impacts of labeled use of the subject products with respect to human health, ecological effects, and environmental fate. Neither the human health assessment nor the ecological effects assessment resulted in objections to registration of the subject products. The environmental fate assessment resulted in objection to registration due to the expected persistence of the fluxapyroxad degradate M700F002 in the environment. The technical reviews are presented in the Appendix of this letter. On February 27, 2014, the Department sent correspondence indicating that the proposed labeling was not acceptable in New York due to unmitigated concerns with respect to the potential of fluxapyroxad to contaminate the water resources of New York State. BASF subsequently waived the decision date to allow time to investigate and implement mitigative label language. Updated product labels for the Priaxor and Merivon products were received by the Department on November 18, 2014 and February 3, 2015, respectively. As stated earlier in this letter, the revised labeling proposed by BASF for the Merivon product included the following additional crop groups: bulb vegetables, cucurbit vegetables, leafy vegetables, root vegetables, strawberries and tree nuts. The proposed maximum yearly application rate for bulb vegetables, leafy vegetables and strawberries is 0.54 pounds of fluxapyroxad per acre per year, which is 1.5 times the application rate originally proposed by BASF. Rather than declare the proposed rate increase a Major Change in Labeling, Department staff requested assistance from environmental chemistry staff. An informal review was performed by modeling the higher application rate in the LEACHP model. Modeling indicated a maximum leaching potential on Riverhead soil of the fluxapyroxad degradate M700F002 of 18.6 parts per billion (ppb). Department staff concluded that the proposed higher application rate did not materially

3 Ms. Judy Fersch 3 increase the Department s concern regarding the leaching potential from fluxapyroxad application in sandy soils versus the original Merivon application rate. To mitigate the groundwater concerns communicated by the Department, BASF has implemented the following label language on both product labels: This product is not for sale, distribution or use in Nassau and Suffolk counties in New York State. Additionally, the following statement was placed on the Merivon and Priaxor product labels before the application was submitted in New York State: For Aerial Application in New York State, DO NOT apply within 100 feet of aquatic habitats (such as, but not limited to lakes, reservoirs, rivers, streams, marshes, ponds, estuaries, and commercial fishponds). This language is required for the active ingredient pyraclostrobin in New York and is not a result of the New Active Ingredient review for fluxapyroxad. Due to the environmental fate concerns expressed with respect to fluxapyroxad, the Merivon and Priaxor products will be classified as restricted use pesticides in New York State to ensure that these products are only applied by licensed and trained applicators. The classification as restricted use also allows the Department to track the sale and application of these products throughout the state. This classification falls under 6 NYCRR (e). The following list summarizes the conditions of registration agreed upon by BASF and the Department in order to facilitate registration of Merivon and Priaxor in New York: 1. Sale, use, and distribution is prohibited in Nassau and Suffolk Counties of New York; 2. Merivon and Priaxor both contain the active ingredients fluxapyroxad and pyraclostrobin. Product labels containing the active ingredient pyraclostrobin that also allow aerial application require a 100 foot buffer to aquatic habitats in New York for aerial applications; 3. Products containing fluxapyroxad will be classified as restricted use pesticides in New York. The updated labeling submitted by BASF fully mitigates the Department s concern regarding the potential impact of the use of fluxapyroxad to the water resources of New York State. Therefore, the Department has registered Merivon Xemium Brand Fungicide (EPA Reg. No ) and Priaxor Xemium Brand Fungicide (EPA Reg. No ) for use in the State. Enclosed for your record are copies of the Certificate of Pesticide Registration and stamped Accepted for Registration labels. Please note the yes under the restriction column on the enclosed Certificate of Pesticide Registration and the Classified for Restricted Use in New York State stamp on the enclosed product labels. As such, each product is restricted in its purchase, distribution, sale, use and possession in New York State. The New York State Department of Environmental Conservation Regulations 6 NYCRR 326.3(a) state: It shall be unlawful for any person to distribute, sell, offer for sale, purchase for

4 Ms. Judy Fersch 4 the purpose of resale, or possess for the purpose of resale, any restricted pesticide unless said person shall have applied for, and been issued a commercial permit. Please contact the Pesticide Reporting and Certification Section, at , if you require information on obtaining a commercial permit. The Pesticide Reporting Law within Environmental Conservation Law Article 33 Title 12 requires all certified commercial pesticide applicators to report information annually to the Department regarding each pesticide application they make. Commercial pesticide retailers are required to report all sales of restricted pesticide products and sales of general use pesticide products to private applicators for use in agricultural crop production. If no sales are made within New York State, a report must be filed with the Department indicating this is the case. If you need information relating to the Pesticide Reporting Law, or annual report forms, please call or visit the Department s website at Please note that a proposal by BASF or any other registrant to register a product that contains fluxapyroxad, and whose labeled uses are likely to increase the potential for significant impact to humans, nontarget organisms, or the environment, would constitute a major change in labeling. Such an application must be accompanied by a new application fee and meet the requirements listed in Appendix 1.B. of New York State Pesticide Product Registration Procedures (November 2014). Such information, as well as forms, can be accessed at our website as listed in our letterhead. Please contact Shaun Peterson, of the Pesticide Product Registration Section, at , if you have any questions regarding this letter. Sincerely, Scott Menrath Enclosures Scott Menrath, P.E. Director Bureau of Pest Management

5 Ms. Judy Fersch 5 APPENDIX HUMAN HEALTH ASSESSMENT: The following technical review was produced by staff within the Bureau of Toxic Substance Assessment at the New York State Department of Health (DOH). Fluxapyroxad and the formulated products Merivon and Priaxor Xemium Brand Fungicides were not very toxic in acute oral, dermal and inhalation exposure studies in laboratory animals, although Merivon was moderately toxic in the acute oral study. Neither the active ingredient nor the formulated products were irritating to the eyes and skin (tested on rabbits) or dermal sensitizers (tested on guinea pigs). Both acute and subchronic oral neurotoxicity studies were conducted on fluxapyroxad in rats. In the acute study, neurotoxic effects including reduced motor activity and decreased rearing were observed at a dose level of 500 milligrams per kilogram body weight (mg/kg); the no-observed-effect level (NOEL) was 125 mg/kg. In the subchronic study, dietary administration of fluxapyroxad did not result in any observed neurotoxic effects. The NOEL was set at the highest dose tested, 302 mg/kg/day and 338 mg/kg/day for males and females, respectively. The U.S. Environmental Protection Agency (U.S. EPA) Office of Pesticide Programs calculated an acute oral reference dose (arfd) of 1.25 mg/kg/day for fluxapyroxad based on the NOEL of 125 mg/kg/day from the acute neurotoxicity study in rats and an uncertainty factor of 100. Fluxapyroxad caused some toxicity in subchronic animal feeding studies. In a 90-day rat feeding study, fluxapyroxad caused thyroid follicular hypertrophy and hyperplasia at a dose of 126 mg/kg/day and 35.1 mg/kg/day for males and females, respectively; the NOEL was 31.2 mg/kg/day for males and 7.3 mg/kg/day for females. In a 90-day mouse feeding study, fluxapyroxad caused decreased body weight and body weight gain, and multifocal necrosis in the liver in males at a dose of 1136 mg/kg/day; the NOEL was 390 mg/kg/day for males and 1657 mg/kg/day (the highest dose tested) for females. A 90-day feeding study in dogs resulted in vomiting and changes in clinical chemistry (increased alkaline phosphatase and ɣ-glutamyl transferase) at a dose of 295 mg/kg/day and 238 mg/kg/day for males and females, respectively; the NOEL was 45 mg/kg/day for males and 51 mg/kg/day for females. Similar effects were observed in non-guideline 28-day feeding studies in rats, mice and dogs. In the 28-day rat feeding study, fluxapyroxad caused changes in clinical chemistry (increased serum ɣ-glutamyl transferase, total protein, total globulin, triglyceride and cholesterol), changes in thyroid hormone levels and hypertrophy of thyroid follicular cells at a dose of 176 mg/kg/day and 531 mg/kg/day for males and females, respectively; the NOEL was 9 mg/kg/day for males and 47.8 mg/kg/day for females. U.S. EPA used the 28-day and 90-day rat feeding studies to establish a margin of exposure (MOE) of 100 for short- and-intermediate term inhalation exposures for use in an occupational risk assessment. Fluxapyroxad caused some toxicity in chronic animal feeding studies. In a one-year dog feeding study, fluxapyroxad caused hepatic fibrosis, and clinical chemistry changes

6 Ms. Judy Fersch 6 (increases in alkaline phosphatase, serum ɣ-glutamyl transferase, triglyceride, and alanineaminotransferase; decreases in protein albumin, cholesterol, bilirubin, creatinine, urea and calcium) in males and females as well as vomiting and hepatic cirrhosis in males at a dose of 335 mg/kg/day and 43 mg/kg/day in males and females, respectively; the NOEL was 39 mg/kg/day for males and 9 mg/kg/day for females. In a chronic feeding study in mice, fluxapyroxad caused decreased body weight at a dose of 468 mg/kg/day and 652 mg/kg/day for males and females, respectively; the NOEL was 158 mg/kg/day for males and 107 mg/kg/day for females. In a chronic feeding study in rats, fluxapyroxad caused non-neoplastic liver changes (foci, masses) at a dose of 11 mg/kg/day and 14 mg/kg/day for males and females, respectively; the NOEL was 2.1 mg/kg/day for males and 2.7 mg/kg/day for females. The U.S. EPA Office of Pesticide Programs calculated a chronic oral reference dose (crfd) of mg/kg/day for fluxapyroxad based on the NOEL of 2.1 mg/kg/day in male 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 by DOH staff did not find any significant new information on the toxicity of fluxapyroxad. Fluxapyroxad caused some developmental toxicity in the offspring of pregnant rats and rabbits at doses that also caused maternal toxicity. In the rat developmental toxicity study, maternal toxicity consisted of increased absolute and relative thyroid weights, thyroid hypertrophy and hyperplasia at a dose of 1000 mg/kg/day; the NOEL was 200 mg/kg/day. No developmental effects were observed in this study at the highest doses tested (1000 mg/kg/day). In the rabbit developmental toxicity study, decreased fetal body weight and increased paw hyperflexion was observed at a dose of 60 mg/kg/day; the NOEL was 25 mg/kg/day. Maternal toxicity consisted of decreased body weight at a dose of 60 mg/kg/day; the NOEL was 25 mg/kg/day. In a multi-generation reproduction study in rats, fluxapyroxad was associated with decreased pup body weight and decreased body weight development in offspring at a dose of 50 mg/kg/day; the NOEL was 10 mg/kg/day. Parental toxicity consisted of thyroid follicular hypertrophy and hyperplasia at 50 mg/kg/day; the NOEL was 10 mg/kg/day. No effects on fertility or reproductive performance were observed in this study up to the highest dose tested (300 mg/kg/day). Fluxapyroxad caused some oncogenic effects in rats, but not mice, in chronic toxicity/carcinogenicity studies. The incidence of liver adenomas, carcinomas, and combined adenomas/carcinomas were significantly increased in male rats, and incidences of adenomas and combined adenomas/carcinomas were significantly increased in female rats. In addition, fluxapyroxad caused a significant increase in the incidence of thyroid cell combined adenomas/carcinomas in male rats. The U.S. EPA hypothesized that the liver and thyroid tumors were caused by changes in liver enzyme regulation characterized by: increased cell proliferation resulting in microscopic and macroscopic foci leading to adenoma/carcinoma formation, changes in thyroid hormone homeostasis leading to thyroid follicular cell hypertrophy/hyperplasia leading to tumor formation. Fluxapyroxad and metabolites were negative in a number of genotoxicity studies. Based on these data, the U.S. EPA classified fluxapyroxad as not likely to be carcinogenic to humans below a defined dose range. This classification was based on: 1) no evidence of carcinogenic effects in the mouse study; 2) liver tumors observed in the rat study occurred at doses 11 mg/kg/day; 3) thyroid tumors were

7 Ms. Judy Fersch 7 seen only in male rats at doses 68 mg/kg/day; 4) there are no mutagenicity concerns; and 5) a hypothesized mode-of-action supported by adequate studies that clearly identified the sequence of key events, dose-response concordance and temporal relationship to the tumor types. Thus, U.S. EPA concluded that the quantification of risk using a non-linear approach (RfD) would adequately protect public health for all chronic toxicity, including carcinogenic effects, of fluxapyroxad. The U.S. EPA established tolerances of fluxapyroxad for a wide variety of food crops (Federal Register 77: 28,270 76, May 14, 2012). The acute population adjusted dose (apad) for the general U.S. population and all population subgroups for fluxapyroxad is 1.25 mg/kg/day and has the same basis as the arfd. The chronic population adjusted dose (cpad) for fluxapyroxad is mg/kg/day and has the same basis as the crfd. The U.S. EPA estimated that acute and chronic dietary exposures to fluxapyroxad residues from all crops for which there are tolerances and from drinking water would be 2 percent of the apad (acute exposures) and 14 percent of the cpad (chronic exposures) for the general U.S. population. Infants (less than 1 year) were identified as the most exposed group for acute dietary exposures to fluxapyroxad residues with an estimated exposure of 6 percent of the apad. Children (1-2 years) were identified as the most exposed group for chronic dietary exposures to fluxapyroxad residues with an estimated exposure of 48 percent of the cpad. 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 additionally reported the results of an occupational risk assessment for short- and intermediate-term inhalation exposures to fluxapyroxad for handler and postapplication exposure scenarios. Dermal risks were not addressed because a dermal toxicity endpoint was not identified for fluxapyroxad in a 28-day dermal toxicity study. For determining margins of exposure (MOEs), the U.S. EPA compared estimated short-term (1 30 days) inhalation exposures to a NOEL of 9 mg/kg/day from a 28-day rat feeding study (changes in thyroid hormones and thyroid follicular hypertrophy/hyperplasia). The estimated intermediateterm (1 6 months) inhalation exposure were compared to a NOEL of 35.1 mg/kg/day from a 90-day rat feeding study (thyroid follicular hypertrophy/hyperplasia). The short- and intermediate-term inhalation MOEs for the handling tasks of mixer/loader and applicator ranged from 25,000 to 750,000. Generally, the U.S. EPA considers MOEs of 100-fold or greater to provide adequate worker protection. There are no chemical specific federal or New York State drinking water/groundwater standards for fluxapyroxad. Based on its chemical structure, this chemical falls 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). Neither fluxapyroxad nor the formulated products were very acutely toxic or irritating in laboratory animal studies, although Merivon was moderately toxic in the acute oral study. Fluxapyroxad caused some effects in neurotoxicity, subchronic, chronic, developmental, and reproductive toxicity animal feeding studies. The primary target organ was the liver (rats, mice,

8 Ms. Judy Fersch 8 dogs) with additional toxicity in the thyroid (rats only). However, estimated dietary risks from exposure to fluxapyroxad via crop residues and drinking water are low and were considered acceptable by the U.S. EPA. In addition, estimated risks posed by fluxapyroxad to workers from use of this product are within the range considered acceptable by the U.S. EPA. Therefore, we do not object to the registration of Priaxor and Merivon Xemium Brand Fungicides in New York State on the basis of direct human health risks. ECOLOGICAL EFFECTS ASSESSMENT: The Department s Bureau of Habitat (BOH) evaluated the proposed use of fluxapyroxad as contained in the Merivon and Priaxor products. Shown below is the assessment. 1. Product Background: The physical/chemical characteristics of fluxapyroxad are summarized in Table 1, below. Table 1. Physical/chemical characteristics of fluxapyroxad. Parameter Fluxapyroxad Empirical formula: C18H12F5N3O Molecular weight: g/mole Density: 1.47 g/ml Water solubility (20 C): 3.44 ph 7 Log Kow (20 C): Toxicity: Fluxapyroxad exhibits low acute toxicity in mammals. It was classified as not likely to be carcinogenic to humans. There was low concern for neurotoxic effects of fluxapyroxad at any mammalian life stage, and there was no evidence observed of susceptibility to reproductive and developmental studies. Chronic liver toxicity was observed in rats, mice, and dogs. At most, fluxapyroxad was found to be slightly toxic to birds. To aquatic organisms, fluxapyroxad was considered to be moderately to highly toxic on an acute basis, and moderately toxic on a chronic basis. In contrast, metabolites are practically non-toxic to fish. Fluxapyroxad was only slightly toxic to bees. The toxicity of fluxapyroxad to ecological receptors is summarized in Table 2, below. Table 2. Summary of the ecotoxicological testing conducted for fluxapyroxad. Organism Test Result Comment Mammalian Rat Acute oral LD50 > 2,000 mg/kg NOAEL = 2,000 mg/kg Rat 28 day dietary LOAEL = 500 ppm NOAEL = 100 ppm

9 Ms. Judy Fersch 9 Organism Test Result Comment Rat parental Reproduction LOAEL=50 mg/kg/day NOAEL=10 mg/kg/day LOAEL=412 ppm food NOAEL=82 ppm food, based on bw mean of 136 g and food consumption rate of kg/day NOAEL for reproductive effects only=300 Rat-offspring reproduction LOAEL=50 mg/kg/day NOAEL=10 mg/kg/day Avian Bobwhite quail and Acute oral LD50>2,000 mg/kg/day mallard duck NOEL=2,000 mg/kg/day Bobwhite quail 5 day dietary LC50=2,457 ppm food Mallard duck Rainbow trout (Oncorhynchus mykiss) Common Carp (Cyprinus carpio) Fathead minnow (Pimephales promelas) Bluegill sunfish (Lepomis macrochirus) Fathead minnow ELS Daphnia magna NOEC=313 ppm food 22 week avian LOEC=1000 ppm food reproduction NOEC=300 ppm food Aquatic freshwater fish Acute 96 hour LC50=0.63 mg/l NOEC=0.22 mg/l Acute 96 hour renewal Acute 96 hour Acute 96 hour LC50=0.29 mg/l NOEC=0.17 mg/l LC50=0.47 mg/l NOEC=0.33 mg/l LC50=1.15 mg/l NOEC=0.57 mg/l 32 day LOEC=0.068 mg/l NOEC=0.036 mg/l Aquatic freshwater invertebrates 48 EC50 EC50=6.78 mg/l NOEC=4.83 mg/l immobilization Daphnia magna 21 day life cycle EC50=1.93 mg/l LOEC=0.95 mg/l NOEC=0.46 mg/l Marine/Estuarine mg/kg/day Developmental effects

10 Ms. Judy Fersch 10 Organism Test Result Comment Sheepshead minnow (Cyprinodon variegatus) 96 hour acute LC50=1.39 mg/l NOEC=0.37 mg/l Mysid shrimp (Americamysis bahia) Oyster larvae (Crassostrea virginica) Mysid shrimp (Americamysis bahia) Aquatic macrophyte Lemna gibba Green algae Selenastrum capricornutum Blue-green algae Anabaena flosaquae FW diatom Navicula pelliculosa Marine diatom Skeletonema costatum 96 hour acute LC50=3.6 mg/l NOEC=0.6 mg/l 96 hour EC50 for shell deposition Chronic, 29 day life cycle 7 day EC50, frond count 96 hour EC50, cell density 96 hour EC50, cell density 96 hour EC50, cell density & growth rate 96 hour EC50, cell density EC50=0.96 mg/l NOEC=0.082 mg/l MATC=0.39 mg/l NOEC=0.28 mg/l Aquatic Plants EC50=2.19 mg/l NOEC=0.44 mg/l EC50=0.37 mg/l NOEC=0.15 mg/l EC50=1.72 mg/l NOEC=0.48 mg/l EC50=1.6 mg/l NOEC=0.44 mg/l EC50=0.83 mg/l NOEC=0.2 mg/l Terrestrial invertebrates Honeybee Acute contact 48 hour LD50 > 100 μg/bee Honeybee Acute oral 40 hour LD50>110.9 μg/bee Honeybee foliage residue No effect to bees from foraging vegetation treated to kg/ha Earthworm 14 day LC50 via soil exposure LC50 > 1,000 mg/kg dry soil NOEC=125 mg/kg dray soil Sediment Unacceptable because of poor reproduction in controls

11 Ms. Judy Fersch 11 Organism Test Result Comment Hyalella azteca 10 day sediment EC50>973 mg/kg toxicity test NOEC>973 mg/kg Chironomus dilutus Marine amphipod 10 day sediment toxicity test 10 day sediment toxicity test EC50 > 527 mg/kg LOEC=145.8 mg/kg NOEC=75.9 mg/kg EC50 =141.6 mg/kg LOEC=57 mg/kg NOEC=18 mg/kg Metabolite toxicity to Rainbow trout M700F hour acute LC50> 100 mg/l NOEC=100 mg/l M700F hour acute LC50> 100 mg/l NOEC=100 mg/l M700F hour acute LC50> 100 mg/l NOEC=100 mg/l Metabolite toxicity to Daphnia magna M700F001 M700F002 M700F Exposure: 48 EC50 immobilization 48 EC50 immobilization 48 EC50 immobilization A. Summary of Environmental Fate EC50> 100 mg/l NOEC=100 mg/l EC50> 100 mg/l NOEC=100 mg/l EC50> 100 mg/l NOEC=100 mg/l EPA reviewer considered the NOEC to be 67 mg/kg for growth but there were problems with the statistical analysis supporting this value In soil, fluxapyroxad is stable to photolysis. It degrades primarily by aerobic microbial degradation. Aerobic metabolism studies conducted in soil samples from Idaho, Illinois, New Jersey, Wisconsin, California, Georgia, Indiana, and North Carolina yielded DT50 1 times of 1830, 676, 118, 387, 729, , and 476 days, respectively. The geometric mean DT50 is 547 days. The DT50 for microbial degradation in anaerobic soil was determined to be 591 days. Field dissipation studies were conducted in Manitoba (Canada), Texas, Illinois, New York, California, and Washington. The DT50s from those studies were 76, 16.7, 149, 330, 314, and 436 days, respectively, yielding a geometric mean field dissipation DT50 of 143 days. 1 The DT50 is the time for 50% of the material to dissipate/degrade; equivalent to half-life.

12 Ms. Judy Fersch 12 In water, fluxapyroxad was stable to both photolysis and hydrolysis. It is degraded primarily by aerobic microbial metabolism. Under dark conditions, fluxapyroxad decreased from 87-95% of the total applied active to 11% in 100 days. In sediment, it steadily increased from 5-8% of the total applied active to between 73-78%. Under light conditions, results were much the same except the total active in sediment only reached about 59-62%. When tested in aerobic water/sediment systems under dark conditions, the DT50 for water and sediment ranged from days and days, respectively. Under light conditions, the DT50 for water and sediment ranged from days and days, respectively. Under anaerobic conditions, the DT50s for water and the water/sediment system were 177 and 731 days, respectively. B. Major degradates and degradation pathways In aerobic soil, the two major metabolites detected were M700F001 and M700F002, at maximum values of 33% and 39% of the total active applied, respectively. Fluxapyroxad degrades to M700F001 which in turn degrades to M700F002, which in turn is degraded to bound residues and CO2. The half-life of M700F001 ranged from 3-9 days. M700F002 seemed to be about as persistent as the parent fluxapyroxad. In anaerobic soil, only M700F001 was detected. In soil, the non-extractable residues increase to as much as 55% of the total active applied. In aquatic degradation studies conducted in the dark, only M700F002 was detected, at a maximum of 4% of the total active applied. In aquatic degradation studies conducted in the light, M700F001 and M700F007 were detected at 11% and 7.5% of the total active applied, respectively. All of the important metabolites are significantly less toxic than the parent compound. C. Exposure assessment modeling Avian and mammalian risks were evaluated using the AVATOX and MAMTOX models. As a worst case scenario, upper level residue values were determined using the Hoerger and Kenaga nomagraph based on the maximum application rate of 0.36 lbs AI/acre. No avian or mammalian acute toxicity thresholds were exceeded. No avian chronic toxicity thresholds were exceeded. The mammalian reproductive NOEL of 82 ppm food was exceeded, but the risk quotient was 1.1, indicating a very slight exceedance. The PONDTOX model was used to assess potential acute and chronic risks to freshwater fish and invertebrates, marine/estuarine fish and invertebrates, and aquatic plants. The first scenario tested was direct application. If fluxapyroxad was applied directly to a one acre pond either 0.5 feet or 1 foot deep at the maximum single application rate of 0.11 lbs AI/acre, the resulting concentrations do not exceed any toxic threshold. If the maximum application rate of

13 Ms. Judy Fersch lbs AI/acre is substituted, the oyster larvae NOEC is exceeded if the pond depth is 1.0 foot. If the pond depth were only 0.5 feet, then the NOECs for freshwater fish, oyster larvae, and FW green algae are exceeded, but none of the LC50s. For runoff modeling, the PONDTOX Model selects possible runoff percentages of 0.5%, 1.5%, and 3% to test, based on the log Kow. The model assumes that a 10 acre field is treated with the selected application rate, and after a one inch rainfall, all of the runoff water is transported to a one acre pond, which can be 1, 3, or 6 feet deep. When both the single and maximum application rates (0.11 and 0.36 lbs AI/acre) are tested using the 3% runoff rate, with none of the applied product removed because of foliar intercept, none of the aquatic risk thresholds were exceeded. Using the maximum application rate of 0.36 lbs AI/acre, none of the risk quotients are exceeded until the runoff rate exceeds 5%. Using the single application rate of 0.11 lbs AI/acre, none of the risk quotients are exceeded until the runoff rate exceeds 17%. 4. Risk Assessment: Fluxapyroxad has low toxicity to birds and mammals. It is moderately to highly toxic to aquatic organisms. Exposure assessment models show that when applied multiple times at labeled rates, fluxapyroxad is unlikely to be harmful to terrestrial or aquatic non-target organisms. If 50% of the applied product were intercepted by foliage and not subject to runoff, then a runoff rate of nearly 15% of the maximum seasonal application rate is required to exceed to lowest aquatic threshold in the shallowest (1 foot deep) pond. Fluxapyroxad is also highly persistent, and clearly has the potential to accumulate in treated soil and aquatic sediment. The HALFLIFE model can be used to estimate the potential buildup of fluxapyroxad in soil. For example, assume 10 applications of fluxapyroxad are made one year (365 days) apart, at the maximum seasonal application rate of 0.36 lbs AI/acre. The field dissipation rate half-life from a New York soil was determined to be 330 days, indicating that about 55.3% of the applied fluxapyroxad would degrade over a one year period. After five years, an equilibrium would be achieved, and the resulting buildup would be equivalent to a single application of fluxapyroxad at a rate of 0.65 lbs AI/acre. When this application rate is modeled, only mammalian dietary and chronic NOAELs are marginally exceeded on short grass, and fluxapyroxad will not persist for five to ten years on grass. When aquatic risks are modeled using the buildup application rate equivalent, only the fathead minnow chronic NOEC is exceeded in a one foot pond, but that exceedance goes away if even as little as 10% of the applied material was lost to foliar interception. 5. Summary and Conclusion: Despite its apparent persistency and toxicity to aquatic organisms, when used as labeled, fluxapyroxad is unlikely to be harmful to non-target organisms. Therefore, Bureau of Habitat staff do not object to registration in New York State.

14 Ms. Judy Fersch 14 ENVIRONMENTAL FATE ASSESSMENT: Environmental chemistry staff within the Department s Bureau of Pest Management evaluated the proposed use of fluxapyroxad as contained in the Merivon and Priaxor products. Shown below is the assessment. Technical Review Findings This technical review was prepared using the USEPA Memorandum Transmittal of Data Evaluation Records for Environmental Fate Studies, dated January 04, This document was reviewed and submitted by Environmental Fate and Effects Division (EFED) staff. Major Transformation Products from Aerobic Soil Metabolism Studies M700F001: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid M700F002: 3-difluoromethyl-1H-pyrazole-4-carboxylic acid age Environmental Fate Study Major Degradate Formed of Initial Applied MRID No. Aqueous Hydrolysis None Aqueous Photolysis None Soil Photolysis None Aerobic Soil Metabolism M700F M700F There were study results submitted that centered on the minor degradate M700F007 but since this degradate was not modeled for potential groundwater impact, they will not be included in this technical review. Water Solubility No Studies Provided The water solubilities of the parent compound fluxapyroxad and the two major degradates produced in the aerobic soil metabolism studies, M700F001 and M700F002, were not provided in the submitted materials but were found in the University of Hertfordshire Pesticide Properties Database (PPDB). These values will be used to model the groundwater leaching potential of these compounds.

15 Ms. Judy Fersch 15 Compound Water Solubility (mg/l, ppm) Fluxapyroxad M700F001 39,990 3 M700F002 31,580 4 Aqueous Hydrolysis MRID In an acceptable study in the dark at 50 C, in sterile aqueous buffered solutions, fluxapyroxad was found to be stable to hydrolysis at ph 4, 5, 7, and 9. Since fluxapyroxad was found to be hydrolytically stable at 50 C, further investigations at 25 C were unnecessary. Aqueous Photolysis MRID In an acceptable study at 22 C, samples in sterile aqueous buffered solution at ph 7 were irradiated continuously at nm wavelength (equivalent to a clear summer day at latitude 40 N) for 15 days with no degradation observed. Therefore, fluxapyroxad was found to be stable to aqueous photolysis under simulated sunlight at ph 7. Soil Surface Photolysis MRID In an acceptable study at 22 C using a loamy sand soil with ph 7.9 and percent organic carbon (%OC) at 2.4, the soil was irradiated for 15 days. One minor metabolite M700F007 was found in the irradiated and the dark control samples at maximum levels of 2.8% and 2.4%, respectively, of the originally applied showing that light has no significant influence on the environmental fate of fluxapyroxad. Aerobic Soil Metabolism It should be noted that 14 C-radio-labeled fluxapyroxad was used in the aerobic soil metabolism studies and the 14 C radio-label was present at one of the three following locations on the parent molecule: the pyrazole group, the aniline group and the trifluorophenyl group, as shown in the figure below. In these experiments, the predominant degradates that were formed were M700F001 and M700F002, which follows the left side of the proposed degradation pathway which is illustrated on the next page. It was generally found that when M700F003 was formed, it became tightly and irreversibly bound to the organic carbon materials within the soil matrix

16 Ms. Judy Fersch 16 Proposed Degradation Pathway F F O 14 C Aniline Group Pyrazole Group N 14 C N H N Fluxapyroxad 14 C Trifluorophenyl Group F F F F F O N OH N M700F001 H 2 N F F F F O F M700F003 N OH HN M700F002 CO 2 + Bound Residues

17 Ms. Judy Fersch 17 Aerobic Soil Metabolism of Fluxapyroxad MRID In an acceptable study using four soils from the United States, only the New Jersey soil produced a major transformation product ( 10% of total applied), which was found to be M700F001 at 33.61% of the total applied, with the maximum occurring after 123 days. The bolded value 33.61% will be used in determining the application rate of the degradate M700F001 in LEACHP modeling and the bolded half-life 117, which had the best fit (r 2 ) to the data, will be used for the LEACHP modeling of the parent fluxapyroxad. Soil Type ph Organic Carbon Half-Life (Days) Major Transformation Products Max of Applied Idaho, sandy loam None - Illinois, loam None - New Jersey, loam M700F Wisconsin, loamy sand None - Aerobic Soil Metabolism of Parent Fluxapyroxad MRID In an acceptable study, one sandy loam from Germany was used and two major degradates were produced, namely, M700F001 and M700F002 at 12.1% and 38.5% of the total applied, respectively. M700F001 had its maximum occurring at 30 days and M700F002 had its maximum at 120 days, the latter probably being produced from the degradation of the former. The bolded value 38.5% will be used in determining the application rate of degradate M700F002 in LEACHP modeling. Soil Type Bruch West, Germany, sandy loam (two studies with different radio-labels) ph Organic Carbon Half-Life (Days) Major Transformation Products Max of Applied 71.9 M700F M700F

18 Ms. Judy Fersch 18 Aerobic Soil Metabolism of Parent Fluxapyroxad MRID In a conditionally acceptable study, one sandy loam from Germany was used and no major degradates were produced. Soil Type Bruch West, Germany, sandy loam ph Organic Carbon Half-Life (Days) Major Transformation Products None - Max of Applied Aerobic Soil Metabolism of Parent Fluxapyroxad MRID In an acceptable study, four sandy loam soils from the United States were used and no major degradates were produced. All half-lives exceeded the 120-day study period and those listed in the following table were optimized values using various models. Organic Major Half-Life Transformation Max of Soil Type ph Carbon (Days) Products Applied California, sandy loam None - Georgia, sandy loam None - North Carolina, sandy loam None - Indiana, loam None - Aerobic Soil Metabolism of Parent Fluxapyroxad MRID In an acceptable study, three soils were used, one from Spain and the others from Germany, and no major degradates were produced. Soil Type Arahal, Spain, silty clay loam Kleve Keeken, Germany, loam Nierswalde, Germany, silt loam ph Organic Carbon Half-Life (Days) Major Transformation Products None None - Max of Applied None -

19 Ms. Judy Fersch 19 Aerobic Soil Metabolism of Degradate M700F001 MRID In a conditionally acceptable study, three soils were used, two from Germany and one from the United States. One major degradate was produced in all three studies, namely, M700F002. All maximum levels occurred within 30 days. Because the German loamy sand has ph and %OC values more similar to Riverhead, NY, the bolded 9.3 day half-life found in the following table will be used in the LEACHP modeling of degradate M700F001. Organic Major Half-Life Transformation Max of Soil Type ph Carbon (Days) Products Applied LI10, Germany, loamy sand M700F Wisconsin, loamy sand M700F LUFA 2.2, Germany, sand M700F In this study, it is noted that the author also found that M700F002 appeared within three days and quickly increased to maximum amounts of 67.4% to 76% within 30 days with half-lives as follows: LI10 at 168 days, Wisconsin at 128 days, and LUFA 2.2 at 148 days. Aerobic Soil Metabolism of Degradate M700F002 MRID In a conditionally acceptable study, four soils were used, three from Germany and one from the United States, and no major degradates were produced. Because the German loamy sand has ph and %OC values more similar to Riverhead, NY, the bolded 159 day half-life found in the following table will be used in the LEACHP modeling of degradate M700F002. Organic Major Half-Life Transformation Max of Soil Type ph Carbon (Days) Products Applied LI10, Germany, loamy sand None - LUFA 2.2, Germany, sand None - Wisconsin, loamy sand None - Bruch West, Germany, sandy loam None - Anaerobic Soil Metabolism of Parent Fluxapyroxad MRID In a conditionally acceptable study, a soil from the United States was used and it was noted that true anaerobic conditions were never reached until the end of this study, however, there was enough information, to adequately describe the degradation,, and obtain a DT50 value of 591 days

20 Ms. Judy Fersch 20 The degradate M700F001 was formed in the soil during the aerobic phase of this study. It reached a maximum at 3.8% and continued to be formed in the water during the anaerobic phase of the study, reaching a maximum of 9.9%. This suggests that M700F001 has little affinity for soil. M700F001 was not further metabolized to form M700F002. Organic Major Half-Life Transformation Max of Soil Type ph Carbon (Days) Products Applied New Jersey, loam M700F Anaerobic Soil Metabolism of Parent Fluxapyroxad MRID This study was found to be unacceptable so these findings will not be included in this review. Adsorption/Desorption of Parent Fluxapyroxad MRID In an acceptable study, eight soils were used, five European, two from the United States, and one from Japan. Based on the KOC values listed in the following table, fluxapyroxad is considered to have medium to low mobility. It was shown that there was some correlation between the organic carbon in the soil and the kd, suggesting that fluxapyroxad binds to organic carbon, but other mechanisms of binding are likely to be involved. Because the German LUFA 2.1 sand has ph and %OC values most similar to Riverhead, NY soils, the bolded Freundlich adsorption KOC value of in the following table will be used in LEACHP modeling. Adsorption Soil Type ph % OC KOC LUFA 2.1, Germany, sand Obihiro, Japan, sandy loam LI10, Germany, Loamy sand New Jersey, silt loam Nierswald, Germany, silt loam LUFA 2.3, Germany, sandy loam LaGironda, Spain, silty clay loam California, sandy loam

21 Ms. Judy Fersch 21 Adsorption/ Desorption of Degradate M700F001 MRID In an acceptable study, eight soils were used, five European, two from the United States, and one from Japan. No correlation between adsorption and organic carbon and ph could be established. Because the LUFA 2.1 German sand has ph and %OC values more similar to Riverhead soils, the bolded KFOC value of 3.0 found in the following table will be used in the LEACHP modeling of the degradate M700F001. Adsorption Soil Type ph % OC KOC LUFA 2.1, Germany, sand Obihiro, Japan, sandy loam LI10, Germany, Loamy sand New Jersey, silt loam Nierswald, Germany, silt loam LUFA 2.3, Germany, sandy loam LaGironda, Spain, silty clay loam California, sandy loam Adsorption/ Desorption of Degradate M700F002 MRID In an acceptable study, eight soils were used, five European, two from the United States, and one from Japan. The degradate had little affinity for soil, but in spite of this, reasonably precise Freundlich adsorption KFOC values were obtained for most soils. These KFOCs ranged from 1 to 100 ml/g for the eight soils and it was noted that the compound showed high mobility in one soil and very high mobility in all other soils. No correlation between adsorption and organic carbon and ph could be established. Because the LUFA 2.1 German sand has ph and %OC values more similar to Riverhead soils, the bolded KFOC value of 19.1 found in the following table will be used in the LEACHP modeling of the degradate M700F002. Adsorption Soil Type ph % OC KOC LUFA 2.1, Germany, sand Obihiro, Japan, sandy loam LI10, Germany, Loamy sand New Jersey, silt loam Nierswald, Germany, silt loam

22 Ms. Judy Fersch 22 Soil Type ph % OC Adsorption LUFA 2.3, Germany, sandy loam LaGironda, Spain, silty clay loam California, sandy loam Terrestrial Field Dissipation in Legumes MRID In an acceptable field dissipation study of parent fluxapyroxad and degradates M700F001 and M700F002, dissipation was studied in Manitoba soil following two applications one week apart. It was concluded that the major route of dissipation of fluxapyroxad was transformation by aerobic soil metabolism. Neither runoff nor volatilization was considered as routes of dissipation due to careful irrigation management and slope and low fluxapyroxad volatility from soil. KOC Max Depth Detected 5 (inches) Major Route of Dissipation Soil Type ph % OC Half-Life (Days) Parent Fluxapyroxad Clay loam/loam Manitoba, Transformation Canada Degradate M700F001 Transformation Products M700F001 M700F002 Clay loam/loam Manitoba, Canada Transformation M700F002 Degradate M700F002 Clay loam/loam Manitoba, Canada > Transformation CO2 & Bound Residues 5 Not detected above the limit of quantification (LOQ) = 1.0 µg/kg (ppb).

23 Ms. Judy Fersch 23 Terrestrial Field Dissipation in Row Crops MRID In an acceptable field dissipation study using parent fluxapyroxad and degradates M700F001 and M700F002, dissipation was studied in three domestic sites representative of conditions of row crops following three applications one week apart. Half-Life (Days) Max Depth Detected 6 (inches) Major Route of Dissipation Transformation Products Soil Type ph % OC Parent Fluxapyroxad Transformation Texas and - Leaching Transformation Illinois and - Leaching Transformation New York and - Leaching Degradate M700F001 Texas Illinois New York Detected Once Degradate M700F002 Texas Illinois New York Not Detected Not detected above the limit of quantification (LOQ) = 1.0 µg/kg (ppb).

24 Ms. Judy Fersch 24 LEACHP Modeling of Fluxapyroxad The following table lists the parameters that were used for the LEACHP modeling of parent fluxapyroxad and the major degradates M700F001 and M700F002 that were produced in the aerobic soil metabolism studies. Compound Water Solubility (mg/l) Adsorption KFOC Half-Life (Days) Application Rate (lbs/acre/season) Fluxapyroxad M700F001 39, M700F002 31, Due to LEACHP modeling indicating a potential for the fluxapyroxad degradate M700F002 to leach into groundwater at a maximum concentration at 12.4 ppb, Environmental Fate staff recommends that products containing this active ingredient not be registered for sale, sale into, distribution or use in Nassau or Suffolk Counties of New York. The LEACHP profiles can be found in Attachment A of this document. Attachment A LEACHP Profiles PPB Fluxapyroxad K OC = 977.1, t ½ = 117 days, App Rate = 0.36 lbs/acre/yr, Solubility = 3.44 mg/l Maximum at 1.35E-03 ppb Years

25 Ms. Judy Fersch 25 PPB Fluxapyroxad Degradate - M700F001 K OC = 3.0, t ½ = 9.3 days, App Rate = lbs/acre/yr, Solubility = 39,990 mg/l Maximum at 8.14E-04 ppb Years Attachment A Continued Fluxapyroxad Degradate - M700F002 K OC = 19.1, t ½ = 159 days, App Rate = lbs/acre/yr, Solubility = 31,580 mg/l Maximum at 12.4 ppb PPB Years