January 12, Ms. Annette Marine DuPont Crop Protection 1090 Elkton Rd Newark, DE Dear Ms. Marine:

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1 ew York State Department of Environmental Conservation Division of Materials Management Bureau of Pest Management Pesticide Product Registration Section 625 Broadway, Albany, ew York Phone: (518) Fax: (518) Website: Joe Martens Commissioner January 12, 2015 Ms. Annette Marine DuPont Crop Protection 1090 Elkton Rd ewark, DE Dear Ms. Marine: Re: Registration of the Pesticide Products DuPont Exirel Insect Control (EPA Reg. o ) and DuPont Verimark Insect Control (EPA Reg. o ) Containing the ew Active Ingredient Cyantraniliprole (Chemical Code ) The ew York State Department of Environmental Conservation (Department) has evaluated your application (received February 13, 2014) and supplemental materials received to date in support of the registration of the above-referenced pesticide products. DuPont Exirel Insect Control (EPA Reg. o ) contains 10.2% of the active ingredient cyantraniliprole and is formulated as a suspoemulsion. The product is labeled for foliar application to control listed sucking and chewing insects on various field, row, and greenhouse crops. The application rates are to pounds of cyantraniliprole per acre per application, and a maximum of 0.40 pounds of cyantraniliprole per acre per year. DuPont Verimark Insect Control (EPA Reg. o ) contains 18.66% of the active ingredient cyantraniliprole and is formulated as a suspension concentrate. The product is labeled for soil application to various agricultural crops. The application rates are to pounds of cyantraniliprole per acre per application, and a maximum of 0.40 pounds of cyantraniliprole per acre per year. The application package was deemed complete for purposes of technical review on July 7, Pursuant to the review time frame specified in Environmental Conservation Law , a registration decision date of December 4, 2014 was established. Technical reviews of the proposed uses included on the Exirel and Verimark product labels have been performed by the Department and the ew York State Department of Health.

2 Ms. Annette Marine 2. These reviews encompassed the expected impacts of labeled use of the subject products with respect to human health, ecological effects, and environmental fate. either the ecological effects review nor the human health review resulted in objections to registration of the proposed uses. However, the environmental fate technical review resulted in unmitigated concerns with respect to the potential of cyantraniliprole to contaminate the water resources of ew York State. The technical reviews are presented in the Appendix of this letter. A technical issues letter describing these concerns was sent to DuPont Crop Protection (DuPont) on ctober 16, DuPont requested a waiver of the legislatively mandated decision date in order to have sufficient time to prepare updated product labeling. Updated product labels for both the Exirel and Verimark products were received by the Department on January 9, This labeling mitigates the Department s concerns regarding the potential impact of the use of cyantraniliprole to the water resources of ew York State by prohibiting sale, use and distribution in assau and Suffolk Counties. As a result, DuPont Exirel Insect Control and DuPont Verimark Insect Control have been registered in ew York 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 ew York State stamp on the enclosed product labels. As such, each product is restricted in its purchase, distribution, sale, use and possession in ew York State. Furthermore, each product may only be purchased and used by a certified applicator in ew York State. The ew York State Department of Environmental Conservation Regulations 6 YCRR 326.3(a) state: It shall be unlawful for any person to distribute, sell, offer for sale, purchase for 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. Should you require information to obtain a commercial permit, please contact the Pesticide Reporting and Certification Section, at 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 ew 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 visit the Department s website at or call Please note that a proposal by DuPont or any other registrant to register a product that contains cyantraniliprole, and whose labeled uses are likely to increase the potential for significant impact on 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

3 Ms. Annette Marine 3. the requirements listed in Appendix 1.B. of ew York State Pesticide Product Registration Procedures (April 2009). Such information, as well as forms, can be accessed at our website as listed in our letterhead. Please contact Shaun Peterson, of our Pesticide Product Registration Section, at , if you have any questions regarding this letter. Enclosures Sincerely, Scott Menrath Scott Menrath, P.E. Director Bureau of Pest Management

4 Ms. Annette Marine 4. Appendix EVIRMETAL FATE ASSESSMET: The following assessment was produced by the Department s Engineering Geology staff within the Bureau of Pest Management: This technical review was prepared using the U.S. EPA Environmental Fate and Effects Division s (EFED) memorandum 1 that covers the various environmental fate findings for the new active ingredient cyantraniliprole. Major Transformation Products from Aerobic Soil Metabolism Studies I-J9Z38: 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-3,4-dihydro-3,8-dimethyl- 4-oxo-6-quinazolinecarbonitrile I-JCZ38: 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]- '3',5-dimethyl-1,3-benzenedicarboxamide I-JSE76: 4-[[[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]carbonyl]amino]-3- methyl-5-[(methylamino)carbonyl]benzoic acid I-K5A78: 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-3,4-dihydro-3,8- dimethyl-4-oxo-6-quinazolinecarboxylic acid I-PLT97: 2-[3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-1,4-dihydro-8-methyl-4- oxo-6-quinazolinecarboxylic acid The following table lists the major degradates and their maximum percent of formation from the applied parent cyantraniliprole across all environmental fate studies. These values will be used to determine their respective/theoretical application rates in LEACHP modeling: Degradate Study Maximum % of Applied MRID I-J9Z38 Soil Photolysis (moist soil) I-JCZ38 Aerobic Soil Metabolism I-JSE76 Aerobic Soil Metabolism I-K5A78 Aerobic Soil Metabolism I-PLT97 Aerobic Soil Metabolism Data Evaluation Records (DER) for Environmental Fate Studies of Cyantraniliprole to Support ew Chemical Registration, February 06, 2014.

5 Ms. Annette Marine 5. Proposed Degradation Pathway for Cyantraniliprole in Aerobic Soil (Bolded Transformation Products are the Major Degradates from Aerobic Soil Studies) HCH 3 Cyantraniliprole C CH 3 H Br HCH 3 CH 3 H 2 C I-JCZ38 CH 3 H C Br H 2 C Cl H 2 I-J9Z38 CH 3 C Cl Br Cl I-K7H19 CH 3 H C Br HC I-JSE76 CH 3 H HCH 3 C Br Cl H 2 C CH 3 C CH 3 Br Cl I-K5A77 HC H Cl HC CH 3 I-K5A79 H H 2 C Br CH 3 I-PLT97 C Cl HC Br CH 3 I-K5A78 C CH 3 Br Cl Cl

6 Ms. Annette Marine 6. Aqueous Solubility of Cyantraniliprole and the Five Major Degradates The aqueous solubility 2 of cyantraniliprole and its five major transformation products from the aerobic soil metabolism study are listed in the following table. These solubility values will be used in LEACHP modeling. Compound Water Solubility (mg/l) MRID Cyantraniliprole I-J9Z I-JSE I-JCZ I-K5A I-PLT Aqueous Hydrolysis of Cyantraniliprole MRID In an acceptable study in the dark, the hydrolysis rate of cyantraniliprole was found to increase with temperature and ph and the only major transformation product produced was I-J9Z38. The following table lists these findings. The percent formed of I-J9Z38 are the mean values of two replicates. It was found that the production of this degradate in the aerobic soil metabolism studies was largely due to aqueous hydrolysis in the soil rather than from microbial transformation. Compound Cyantraniliprole ph Temperature ( C) First rder T½ Values (Days) r I-J9Z38 Maximum Formed Aqueous Photolysis of Cyantraniliprole MRID In an acceptable study at 25 C, the rate of aqueous photolysis of cyantraniliprole was determined in a sterile buffer solution at ph 4 and sterile natural water at ph 7.4. The ph 4 buffer solution was chosen to minimize degradation due to hydrolysis. Cyantraniliprole was relatively unchanged in the dark controls at ph 4, however, in the natural water dark controls cyantraniliprole steadily degraded to form I-J9Z38 at to % of the applied over the 15-day incubation period. This transformation was attributed to be due to the hydrolysis of cyantraniliprole. 2 Aqueous solubilities of major degradates were provided by Dupont in an sent to Product Registration staff on Aug. 27, The solubility studies can be provided upon request. 3 The percent of initially applied parent cyantraniliprole.

7 Ms. Annette Marine 7. In the irradiated buffer solutions at ph 4, the only major degradate found was I-XX69 which increased to ca 100% of the initially applied parent cyantraniliprole at day-2 and decreasing to a minimum of 76.13% after 15 days. Major degradates formed in this study will not be LEACHP modeled 4. In the irradiated natural water samples, I-XX70 was detected at a maximum of 53.13% after 8 hours which then decreased to less than the limit of detection at day-8. I-QKV54 was formed at a maximum of 84.71% at day-5 decreasing to a maximum of 63.46% after 15 days of irradiation. There was a mixture of unidentified polar components found at a maximum of 21.08% at day-15 with the largest component accounting for 11.72% of the initially applied cyantraniliprole. It is noted that this polar component should be classified as a major degradate and the applicant states that they undertook further analysis and concluded that it is likely a small molecule containing only portions of the parent s molecular structure. The following table lists the degradation rates at constant irradiation of cyantraniliprole using the sterile buffer solution at ph 4 and the natural water at ph 7.4: Matrix Component T½ (Days) r 2 ph 4 Buffer Irradiated Cyantraniliprole I-XX ph 4 Dark Control Cyantraniliprole Cyantraniliprole atural Water ph 7.4 I-XX I-QKV atural Water ph 7.4 Dark Control Cyantraniliprole Soil Surface Photolysis of Cyantraniliprole MRID and Two soil photolysis studies were performed, one using moist soil and one using an airdried soil. At 20 C using the air-dried soil (ambsheim soil, sandy loam, Alsace region of France, ph 7.51, 1.22% organic carbon), no significant photolysis of cyantraniliprole was observed since the results from the irradiated and non-irradiated systems were very similar. The degradate I-J9Z38 was found at day-11at a maximum of 10.34% of the applied parent, which was presumed to be due to the hydrolytic degradation of the parent compound. For the air-dried soil system, it was concluded that the photolysis of cyantraniliprole on the surface of air-dried soil will not be a significant dissipation pathway in the environment. With the moist soil experiment (ambsheim soil, sandy loam, ph 8.00, 2.0% organic carbon), three major degradation products were detected over the course of the study. As was noted in the air-dried system, degradate I-J9Z38 which reached a maximum value of 54.82% at day-10 was likely the result of non-photolytic reactions and has been seen earlier in all soil degradation studies in the dark. In the dark control, degradate I-J9Z38 reached a maximum at 61.60% of the applied at the end of the study on day The major degradates that undergo LEACHP modeling are those that are produced in aerobic soil metabolism studies.

8 Ms. Annette Marine 8. Two additional major degradation products were attributed to photo-degradation and were identified as I-RU71 and I-QKV54. I-RU71 reached a maximum of 14.12% at the end of the study on day-30 while I-QKV54 reached a maximum of 17.18% of the applied at day-15. For the moist soil system, it was concluded that the photolysis of cyantraniliprole on the surface of moist soil may be a significant dissipation pathway in the environment. The following table lists the half-lives of cyantraniliprole using the systems described above. Since the half-lives are extrapolated well beyond the length of the study, they should be regarded as having a high degree of uncertainty. Air-Dried Soil Moist Soil t ½ (days) r 2 t ½ (days) r 2 Irradiated 83.6 ot Provided Dark Control 115 ot Provided Corrected Aerobic Soil Metabolism Studies This section will cover the aerobic soil metabolism study using the parent cyantraniliprole as well as the studies using the five major transformation products that were produced in that parent study. As a result, there will be a total of six aerobic soil metabolism studies covered in this section and all studies were classified as acceptable and fully reliable. Aerobic Soil Metabolism - Cyantraniliprole MRID Two soils were used in this study and the following table lists the soil properties, the temperature of the system, the half-lives of cyantraniliprole, and the transformation products found in the soils during the study. It was indicated on page 19 of the EFED document that degradate I-J9Z38 was likely due to the hydrolysis of the parent molecule rather than by microbial degradation. These five major transformation products will undergo LEACHP modeling to assess their potential for groundwater impact. Soil ame/source/type/temp. C ph rganic Carbon t ½ (Days) r 2 ambsheim/france/loam/22.3 C Tama/Illinois/Silty clay loam/22.3 C Major Transformation Products I-J9Z38 I-JCZ38 I-JSE76 I-K5A78 I-PLT97 I-J9Z38 I-JCZ38 I-JSE76 Max of Applied 16.0 (day 16) 16.6 (day 7) 42.3 (day 41) 28.8 (day 358) 26.3 (day 358) 11.6 (day 300) 13.1 (day 22) 42.9 (day 358) 5 The corrected values were determined by subtracting the first-order rate constant K of the dark controls from those of the corresponding irradiated rate constants.

9 Ms. Annette Marine 9. Aerobic Soil Metabolism - Cyantraniliprole MRID Three soils were used in this study and the following table lists the soil properties, the temperature of the system, the half-lives of cyantraniliprole, and the transformation products found in the soil during the study. It was indicated on page 72 of the EFED document that the presence of the degradate I-J9Z38 may likely be due to the hydrolysis of the parent molecule rather than by bacterial metabolism. Because the Sassafras soil has similar ph and percent organic carbon to Long Island Riverhead soil, those half-lives will be used in the LEACHP modeling of the parent cyantraniliprole and the five major transformation products. These values will be shown in bold type in the tables that follow. Soil ame/source/type/temp. C ph rganic Carbon t ½ (Days) r 2 Gross-Umstadt/Germany/Silt loam/20 C Gross-Umstadt/Germany/Silt loam/10 C Sassafras/Maryland/Sandy loam/20 C Lleida/Spain/Silty clay loam/20 C Major Transformation Products I-J9Z38 I-JSE76 I-JCZ38 I-J9Z38 I-JSE76 I-JCZ38 I-J9Z38 I-JCZ38 I-J9Z38 I-JSE76 I-JCZ38 I-K5A78 Max of Applied (day 60) (day 120) 18.2 (day 90) (day 120) (day 120) (day 60) (day 45) (day 120) (day 60) (day 120) (day 15) (day 120) Aerobic Soil Metabolism Degradate I-J9Z38 MRID Five soils were used in this study and the following table lists the soil properties, the temperature of the system, the half-lives of degradate I-J9Z38, and the transformation products found in the soil during the study. The Maximum of Applied values are the means of two replicates. Soil ame/source/type/temp. C ph rganic Carbon t ½ (Days) r 2 Gross-Umstadt/Germany/Silt loam/20 C ambsheim, France/ Sandy loam/20 C Major Transformation Products I-K5A77 I-K5A78 I-K5A77 I-K5A78 Max of Applied (day120) (day 90) (day 90) (day 120) Sassafras/Maryland/Sandy loam/20 C I-K5A (day 120) Lleida/Spain/Silty clay loam/20 C I-K5A77 I-K5A (day 90) (day 120) Tama/Illinois/Silty clay loam/20 C I-K5A (day 120)

10 Ms. Annette Marine 10. Aerobic Soil Metabolism Degradate I-JSE76 MRID Five soils were used in this study and the following table lists the soil properties, the temperature of the system, the half-lives of degradate I-JSE76, and the transformation products found in the soil during the study. The Maximum of Applied values are the means of two replicates. Soil ame/source/type/temp. C ph rganic Carbon t ½ (Days) r 2 Major Transformation Products Max of Applied Gross-Umstadt/Germany/Silt loam/20 C I-K5A ambsheim, France/ Sandy loam/20 C I-PLT97 I-K5A (day 120) (day 120) Sassafras/Maryland/Sandy loam/20 C one na Lleida/Spain/Silty clay loam/20 C I-PLT (day 120) Tama/Illinois/Silty clay loam/20 C I-K5A (day 60) Aerobic Soil Metabolism Degradate I-JCZ38 MRID Five soils were used in this study and the following table lists the soil types, where the soils originated, the soil properties, the temperature of the system, the half-lives of degradate I-JCZ38, and the transformation products found in the soil during the study. The Maximum of Applied values are the means of two replicates. Soil ame/source/type/temp. C ph rganic Carbon t ½ (Days) r 2 Gross-Umstadt/Germany/Silt loam/20 C ambsheim, France/ Sandy loam/20 C Sassafras/Maryland/Sandy loam/20 C Lleida/Spain/Silty clay loam/20 C Tama/Illinois/Silty clay loam/20 C Major Transformation Products I-K5A79 I-JSE76 I-K5A78 I-K5A79 I-JSE76 I-PLT97 I-K5A78 I-K5A79 I-JSE76 I-JSE76 I-PLT97 I-K5A78 I-K5A79 I-JSE76 Max of Applied (day 120) (day 60) (day 120) (day 60) (day 15) (day 120) (day 120) (day 120) (day 30) (day 30) (day 120) (day 120) (day 120) (day 30)

11 Ms. Annette Marine 11. Aerobic Soil Metabolism Degradate I-K5A78 MRID Five soils were used in this study and the following table lists the soil properties, the temperature of the system, the half-lives of degradate I-K5A78, and the transformation products found in the soil during the study. The Maximum of Applied values are the means of two replicates. Soil ame/source/type/temp. C ph rganic Carbon t ½ (Days) r 2 Major Transformation Products Max of Applied Gross-Umstadt/Germany/Silt loam/20 C one na ambsheim, France/ Sandy loam/20 C one na Sassafras/Maryland/Sandy loam/20 C I-K5A (day 90) Lleida/Spain/Silty clay loam/20 C one na Tama/Illinois/Silty clay loam/20 C one na Aerobic Soil Metabolism Degradate I-PLT97 MRID Five soils were used in this study and the following table lists the soil types, where the soils originated, the soil properties, the temperature of the system, and the half-lives of degradate I-PLT97. The study demonstrated that I-PLT97 degraded slowly and did not generate major degradates apart from small amounts of C2 and non-extractable residues. The Maximum of Applied values are the means of two replicates and because the t½ values were extrapolated well beyond the duration of the study, the resulting correlations (r 2 ) are well below Soil ame/source/type/temp. C ph rganic Carbon t ½ (Days) r 2 Major Transformation Products Max of Applied Gross-Umstadt/Germany/Silt loam/20 C one na ambsheim, France/ Sandy loam/20 C one na Sassafras/Maryland/Sandy loam/20 C , one na Lleida/Spain/Silty clay loam/20 C one na Tama/Illinois/Silty clay loam/20 C one na

12 Ms. Annette Marine 12. Adsorption/Desorption - Cyantraniliprole MRID In an acceptable study in the dark at 20 C, the same five soils that were used in the aerobic soil metabolism studies were used during the adsorption/desorption studies. The following table lists the soil properties, the Freundlich adsorptivity constants (KC) and the corresponding 1/n values. Because the Sassafras soil has similar ph and percent organic carbon to Long Island Riverhead soil, those KCs will be used in LEACHP modeling to be more protective of groundwater. They are shown in bold type. Soil Type ph rganic Carbon Adsorption K C (ml/g) r 2 Gross-Umstadt/Germany/Silt loam ambsheim, France/ Sandy loam Sassafras/Maryland/Sandy loam Lleida/Spain/Silty clay loam Tama/Illinois/Silty clay loam Adsorption/Desorption Degradate I-J9Z38 MRID In an acceptable study in the dark at 20 C, the same five soils used in the aerobic metabolism studies were used here and the soil properties and KCs are listed in the following table. Soil Type ph rganic Carbon Adsorption K C (ml/g) r 2 Gross-Umstadt/Germany/Silt loam , ambsheim, France/ Sandy loam , Sassafras/Maryland/Sandy loam , Lleida/Spain/Silty clay loam , Tama/Illinois/Silty clay loam ,

13 Ms. Annette Marine 13. Adsorption/Desorption Degradate I-JSE76 MRID In an acceptable study in the dark at 20 C, the same five soils used in the aerobic metabolism studies were used here and the soil properties and KCs are listed in the following table. Soil Type ph rganic Carbon Adsorption K C (ml/g) r 2 Gross-Umstadt/Germany/Silt loam ambsheim, France/ Sandy loam Sassafras/Maryland/Sandy loam Lleida/Spain/Silty clay loam Tama/Illinois/Silty clay loam Adsorption/Desorption Degradate I-JCZ38 MRID In an acceptable study in the dark at 20 C, the same five soils used in the aerobic metabolism studies were used here and the soil properties and KCs are listed in the following table. Soil Type ph rganic Carbon Adsorption K C (ml/g) r 2 Gross-Umstadt/Germany/Silt loam ambsheim, France/ Sandy loam Sassafras/Maryland/Sandy loam Lleida/Spain/Silty clay loam Tama/Illinois/Silty clay loam Adsorption/Desorption Degradate I-K5A78 MRID In an acceptable study in the dark at 20 C, the same five soils used in the aerobic metabolism studies were used here and the soil properties and KCs are listed in the following table.

14 Ms. Annette Marine 14. Soil Type ph rganic Carbon Adsorption K C (ml/g) r 2 Gross-Umstadt/Germany/Silt loam ambsheim, France/ Sandy loam Sassafras/Maryland/Sandy loam Lleida/Spain/Silty clay loam Tama/Illinois/Silty clay loam , Adsorption/Desorption Degradate I-PLT97 MRID In an acceptable study in the dark at 20 C, the same five soils used in the aerobic metabolism studies were used here and the soil properties and KCs are listed in the following table. Soil Type ph rganic Carbon Adsorption K C (ml/g) r 2 Gross-Umstadt/Germany/Silt loam , ambsheim, France/ Sandy loam Sassafras/Maryland/Sandy loam , Lleida/Spain/Silty clay loam Tama/Illinois/Silty clay loam , Terrestrial Filed Dissipation Studies Six studies were conducted, three with bare soil and parallel cropped plots. In addition to bare soil plots, a study in California used a leafy crop plot of lettuce, a study in Washington State employed a potato crop plot, and a study in Missouri utilized an alfalfa cropped plot. The three additional studies on bare ground were conducted in ew York, Texas, and Manitoba, Canada. Terrestrial Field Dissipation - Cyantraniliprole MRID In an acceptable study using a sandy loam with ph ranging from 7.81 to 8.2 at depth (28 36 inches) and percent organic carbon ranging from 0.52 to 0.12, a field dissipation study using cyantraniliprole was conducted on a plot of bare soil and a parallel plot planted with

15 Ms. Annette Marine 15. lettuce at a site near Porterville, CA. Cyantraniliprole was applied as a single broadcast to the bare soil plot at lbs ai per acre and to the plot with lettuce as two broadcast applications at lbs ai per acre. Soil core samples were collected at a maximum depth of 36 inches and analyzed for residues of cyantraniliprole and its dark aerobic soil metabolites I-9Z38, I-JCZ38, I- JSE76, I-K5A77, I-K5A78, I-K5A79, and I-PLT97. Selected study findings include: The concentration of cyantraniliprole showed a rapid decline over the 18-month study period in bare soil to negligible amount of applied substance. The decline in bare soil and cropped soil was comparable showing respective declines at ~8% and 5% over 120 days. All monitored metabolites were observed in bare and cropped soil at comparable amounts over 120 days with I-JC938 being the only degradate exceeding 10% of the applied amount on day 120. I-JCZ38 amounted to ~7% on day 46 with all other metabolites not exceeding 5%. The residues found were mostly confined to the upper soil layer of 0-2 and 2-6 inches. o detection in the lower soil depths (below 12 inches) show a general lack of downward movement through the soil column. A simple first order kinetic model yielded a cyantraniliprole half-life (T½) of 22.4 days for the bare soil plot. The primary reviewer considered a double first order in parallel (DFP) was a better fit with the T½ at 10.2 days. Both of these T½ values fall below the 89.8 day half-life that was found in the aerobic soil laboratory studies using Sassafras soil from Maryland (MRID ). The primary reviewer considered that the double first-order in parallel (DFP) model fit best for the bare soil plots which gave a T½ of 10.2 days. There was no evidence of uptake of soil formed metabolites in the crop sample analyzed. Terrestrial Field Dissipation - Cyantraniliprole MRID In an acceptable study using a sandy loam with ph ranging from 7.44 to 8.75 at depth (28 36 inches) and percent organic carbon ranging from 0.64 to 0.06, a field dissipation study using cyantraniliprole was conducted on a plot of bare soil and a parallel plot plants with potatoes at a site near Ephrata, WA. Cyantraniliprole was applied as a single broadcast to the bare soil plot at lbs ai per acre and to the plot with potatoes as two broadcast applications at lbs ai per acre. Selected study findings include: The concentration of cyantraniliprole showed a rapid decline over the 18-month study period in bare soil to negligible amount of applied substance. The decline in bare soil and cropped soil was comparable showing respective declines to ~7% at 120 days.

16 Ms. Annette Marine 16. All monitored metabolites were observed in bare soil and cropped soil at comparable amounts over 120 days with I-J9Z38 being the only one exceeding 10% of the applied amount on day 120. I-JCZ38 amounted to ~8% with all other metabolites not exceeding 6%. The residues found were mostly confined to the upper soil layer of 0-2 and 2-6 inches. o detection in the lower soil depths (below 30 inches) show a general lack of downward movement through the soil column. DFP kinetics showed the best fit for the data giving a T½ at 9.7 days in bare soil and 3.4 days for when applied to potato foliage. Potato foliage showed a T½ of 3.4 days while potato tubers showed no measurable residue at most sampling intervals. There was no evidence of uptake of soil formed metabolites in the crop sample analyzed. Terrestrial Field Dissipation - Cyantraniliprole MRID In an acceptable study using a silty loam with ph ranging from 6.2 to 6.12 at depth (28 36 inches) and percent organic carbon ranging from 1.34 to 0.120, a field dissipation study using cyantraniliprole was conducted on a plot of bare soil and a parallel plot plants with alfalfa at a site near Leonard, M. Cyantraniliprole was applied as a single broadcast to the bare soil plot at lbs ai per acre and to the plot with potatoes as two broadcast applications at lbs ai per acre. Selected study findings include: The concentration of cyantraniliprole showed a rapid decline over the 18-month study period to <10% of the applied amount. All monitored metabolites were observed in bare soil and cropped soil at comparable amounts over 120 days with I-J9Z38 being the only one exceeding 10% of the applied amount on day 120. I-JCZ38 amounted to ~6% with all other metabolites not exceeding 4%. The residues found were mostly confined to the upper soil layer of 0-2 and 2-6 inches with less than 1% of the applied parent detected in the lower soil depths below 12 inches. There were essentially no detections in the depths below 12 inches showing a general lack of downward movement through the soil. DFP kinetics showed the best fit for the data giving a T½ at 44 days. A half-life for the cropped soil was not provided. There was no evidence of uptake of soil-formed metabolites in the crop sample analyzed. Terrestrial Field Dissipation - Cyantraniliprole MRID In an acceptable study using a loamy sand with ph ranging from 6.5 to 5.9 at depth and percent organic carbon ranging from 1.86 to 0.06, a field dissipation study using

17 Ms. Annette Marine 17. cyantraniliprole was conducted on a plot of bare soil near orth Rose, Wayne County, Y. Cyantraniliprole was applied as a single broadcast to the bare soil plot at lbs ai per acre. Selected study findings include: The concentration of cyantraniliprole showed a rapid decline over the 17-month study period to <4% of the applied amount. All monitored metabolites were detectable at some sampling intervals with I- J9Z38 being the only one near or exceeding 10% of the applied amount at any sampling interval. The residues found were mostly confined to the upper soil layer of 0-2 and 2-6 inches with a small amount of the parent and metabolites detected below 12 inches indicating the general lack of mobility down through the soil. First order multi-compartment (FMC) kinetics showed the best fit for the data giving a T½ at 21.6 days. Decreasing levels of the parent and the transformation products was due to bacterial degradation rather than leaching or from runoff. Terrestrial Field Dissipation - Cyantraniliprole MRID In an acceptable study using a loamy sand with ph ranging from 7.9 to 8.2 at depth and percent organic carbon ranging from 0.70 to 0.23, a field dissipation study using cyantraniliprole was conducted on a plot of bare soil at a site near Raymondville, TX in Wayne County. Cyantraniliprole was applied as a single broadcast to the bare soil plot at lbs ai per acre. Selected study findings include: The concentration of cyantraniliprole showed a rapid decline over the 18-month study period to <12% of the applied amount. All monitored metabolites were detectable at some sampling interval. I-J9Z38, I-JSE76, and I-K5A78 were the only metabolites to approach or exceed 10% of the applied amount at any sampling interval. All other metabolites did not exceed 5% of applied. The residues found were mostly confined to the upper soil layer of 0-2 and 2-6 inches. Almost no parent compound and only a small amount of metabolites were detected below 12 inches. Total levels in the lowest two depths were in the range of 1-2% so minor losses via leaching cannot be completely ruled out. A single first order model gave a T½ at 16.7 days.

18 Ms. Annette Marine 18. Terrestrial Field Dissipation - Cyantraniliprole MRID In an acceptable study using a loamy sand with ph ranging from 7.8 to 8.4 at depth and percent organic carbon ranging from 3.84 to 0.349, a field dissipation study using cyantraniliprole was conducted on a plot of bare soil near Raymondville, Texas. Cyantraniliprole was applied as a single broadcast to the bare soil plot at lbs ai per acre. Selected study findings include: The concentration of cyantraniliprole showed a rapid decline especially in the first three months after application and the residue declined to around 6% for the parent compound. Degradation of the parent and many metabolites was perhaps the slowest among all dissipation studies due to frozen conditions over a significant period of the study. All monitored metabolites were detectable at some sampling interval. I-J9Z38 was the only metabolite detected approaching 10% of the applied amount at any sampling interval. All other metabolites were found below 4% of the applied and many less than 1% at all sampling intervals. The residues found were mostly confined to the upper soil layer of 0-2 and 2-6 inches. Almost no parent compound and only a small amount of metabolites were detected below 12 inches. A first order multi compartment model gave a T½ at 13.5 days. Anaerobic Soil Metabolism - Cyantraniliprole MRID In an acceptable study, the anaerobic soil biotransformation of cyantraniliprole was studied in a sandy loam soil from ambsheim, France with ph 8.05 and percent organic carbon at 1.22%. The amount of parent test substance present in the soil extracts decreased throughout the study with nearly 50% of the parent being degraded by the time the aerobic phase ended. Then under anaerobic conditions, the cyantraniliprole levels declined to below the limit of detection at day 120. The best fit kinetic model was FMC which showed an r 2 value of 1.00 and a t½ of 4.36 days. The major degradate I-J9Z38 was found at 71.88% of the original applied on day 30 and I- K5A78 was detected at 16.17% on day 120. Anaerobic Water/Sediment System Metabolism - Cyantraniliprole MRID In an acceptable study, the fate of cyantraniliprole under anaerobic conditions was studied in an aquatic sediment test system with the sediment and overlaying water collected from a natural location at Calwich Abbey Lake from Calwich, UK. The overlying water had a ph of 7.8 (no dissolved organic carbon level provided) and the sediment was a sandy loam with ph 6.9 and percent organic carbon at 4.42%. The applied amount of cyantraniliprole in the water phase declined to less than the limit of quantitation at day 353 with three transformation products detected. In anaerobic water, I-J9Z38 was the only major degradate reaching a maximum value of 27.56% of the applied at

19 Ms. Annette Marine 19. day 7 and 71.48% of the applied in the soil on day 56. Cyantraniliprole and I-J9Z38 had t½ values of 2.1 days and 8.3 days, respectively, using the best fit model FMC with respective r 2 values of and Cyantraniliprole degraded in the water phase and also partitioned into the sediment where it was further degraded to other metabolites. Dissipation in the sediment was somewhat slower than in the water phase with a t½ of 12.1 days. Anaerobic Water/Sediment System Metabolism - Cyantraniliprole MRID In an acceptable study, the fate of cyantraniliprole under anaerobic conditions was studied in an aquatic sediment test system with the sediment and overlaying water collected from a natural location at Swiss Lake, Chatsworth, Derbyshire, UK. Abbey Lake from Calwich, UK. The overlying water had a ph of 5.9 and a dissolved organic carbon level at 10.7 mg/l while the sediment had a percent organic carbon at 0.7%. The major degradate formed was I-J9Z38 which was detected in the total system at a maximum of 80.28% of the amount applied. The T½ value for cyantraniliprole in the total system was 11.9 days and the degradation rate was faster in the water phase than in the sediment phase. LEACHP Modeling of Cyantraniliprole and Major Degradates Modeling was performed using the following parameters which were discussed in the sections above and the LEACHP profiles are found in the LEACHP Modeling Profiles at the end of this review. All of these modeling parameters are combined in the following table: Compound Solubility (mg/l) Adsorption K C (ml/g) t ½ (days) Application Rate (lbs/acre/season) Cyantraniliprole I-J9Z , I-JSE I-JCZ I-K5A I-PLT ,835 1, K C and half-life (t ½) values were taken from studies using the Sassafras soil. Application rates of degradates were determined using the equation C App Rate = A* B * D Where: A = App. Rate of parent compound cyantraniliprole B = Max percent formed across all environmental fate studies C = Molecular weight of degradate D = Molecular weight of parent cyantraniliprole

20 Ms. Annette Marine 20. Conclusion The LEACHP modeling predicts that the major cyantraniliprole degradate identified as I- JSE76 will leach from a Riverhead soil type at concentrations ranging from approximately 32 to 43 ppb. LEACHP modeling suggests that leaching of cyantraniliprole and the remaining four degradates (I-J9Z38, I-JCZ38, I-K5A78, and I-PLT97) may also occur, but at much lower concentrations. Specifically, modeling indicates that cyantraniliprole may leach from Riverhead soil at a concentration 0.41 ppb and the degradates may leach from the soil at concentrations ranging from 1.61x10-9 ppb to ppb. The Riverhead soil type is representative of soil conditions found on Long Island. The I-JSE76 leaching concentrations are approaching the YSDH drinking water criteria of 50 ppb for unspecified organic contaminants (UCs). Based on the likelihood that the major degradate, I-JSE76, may leach from the Riverhead soil type, use of this product in assau and Suffolk Counties should be prohibited because of the susceptibility of the Long Island sole source aquifer system to surface contamination. To assess the potential for I-JSE76 to leach from soil types outside of the Long Island area, LEACHP modeling was additionally performed using the Howard soil series. The Howard soil type is representative of soil conditions found in upstate ew York. To model I-JSE76, the LEACHP input parameters, including half-life and adsorption coefficient for I-JSE76, were derived from the registrant s studies for soil types similar to the Howard soil. Specifically, an adsorption coefficient of 14 ml/g and a half-life of 84.9 days were selected from studies using the ambsheim loam soil type. The LEACHP modeling predicted that I-JSE76 will leach from a Howard soil type at concentrations up to approximately 9 ppb. Results of the six terrestrial field dissipation studies are generally consistent with the LEACHP modeling. In particular, out of the five major cyantraniliprole degradates, I-JSE76 typically leached to the greatest depths. In four of the field dissipation studies, I-JSE76 leached to the inch depth interval during the studies, but was not detected from this depth interval at the end of each of the studies. verall, I-JSE76 was detected at a maximum concentration of 0.9 ppb from the inch depth interval. The highest I-JSE76 concentration (14.4 ppb) was detected in soil collected from the zero to two inch depth interval. Results of the LEACHP modeling using the Howard soil series combined with terrestrial field dissipation studies suggests that some leaching of I-JSE76 may occur from upstate soils. The model predicts that I-JSE76 may leach from the soil at a depth of one meter at a maximum concentration of approximately 9 ppb. While the terrestrial field dissipation studies also suggest that some leaching of I-JSE76 may occur, the studies suggest that the leaching will occur at lower concentrations (maximum of 0.9 ppb at 36 inches), to shallower depths, and that I-JSE76 will degrade to non-detect levels. Based on the LEACHP modeling using the Howard soil series and review of the field dissipation studies, use of this product in areas outside of assau and Suffolk Counties is acceptable.

21 Ms. Annette Marine 21. LEACHP Modeling Profiles 0.45 Cyantraniliprole K C = 243, t ½ = 89.8 days, App Rate = 0.40 lbs/acre/yr, Solubility = mg/l Maximum at 0.41 ppb PPB Years 45 Cyantraniliprole Degradate - I-JSE76 K C = 28, t ½ = 336 days, App Rate = lbs/acre/yr, Solubility = 45 mg/l Maximum at 42.6 ppb PPB Years

22 Ms. Annette Marine 22. PPB Cyantraniliprole Degradate - I-JCZ38 K C = 209, t ½ = 10.1 days, App Rate = lbs/acre/yr, Solubility = 40 mg/l Maximum at 1.89E-05 ppb Years 1.8E-09 Cyantraniliprole Degradate - I-J9Z38 K C = 7,887, t ½ = 200 days, App Rate = lbs/acre/yr, Solubility = 0.23 mg/l Maximum at 1.61E-9 ppb 1.6E E E-09 PPB 1E-09 8E-10 6E-10 4E-10 2E Years

23 Ms. Annette Marine 23. PPB Cyantraniliprole Degradate - I-K5A78 K C = 916, t ½ = 94 days, App Rate = lbs/acre/yr, Solubility = 43 mg/l Maximum at 1.88E-4 ppb Years 0.06 Cyantraniliprole Degradate - I-PLT97 K C = 1,835, t ½ = 1,837 days, App Rate = lbs/acre/yr, Solubility = 24 mg/l Maximum at 5.48E-2 ppb PPB Years

24 Ms. Annette Marine 24. PPB Cyantraniliprole Degradate - I-JSE76 (Howard Soil Profile) K C = 14 ml/g, t ½ = 84.9 days, App Rate = lbs/acre/yr, Solubility = 45 mg/l Maximum at 9.04 ppb Years HUMA HEALTH ASSESSMET: The following assessment was produced by staff within the Bureau of Toxic Substance Assessment at the ew York State Department of Health (DH): Acute Toxicity either cyantraniliprole nor the formulated products DuPont Exirel Insect Control and DuPont Verimark Insect Control were very toxic in acute oral, dermal or inhalation exposure studies in laboratory animals or very irritating to skin and eyes (tested on rabbits). The Exirel formulated product tested positive for skin sensitization, whereas the active ingredient and the Verimark formulated product were not skin sensitizers (tested on guinea pigs). eurotoxicity Both acute and subchronic oral neurotoxicity studies were conducted on cyantraniliprole in rats. Adverse effects were not observed in either study at any tested dose level. The noobserved-effect-levels (ELs) were 2,000 milligrams per kilogram body weight (mg/kg) and 1,404 mg/kg/day, the highest doses tested in the acute and subchronic studies, respectively. Chronic Toxicity Cyantraniliprole caused some toxicity in chronic feeding studies in laboratory animals. In a chronic feeding/oncogenicity study in rats, cyantraniliprole caused liver toxicity (microscopic pathology characterized by foci of cellular alteration and focal vacuolation) at 84.8

25 Ms. Annette Marine 25. mg/kg/day; the EL was 8.3 mg/kg/day. In a chronic feeding study in mice, an increase in food consumption and a decrease in food efficiency with minimal changes in body weights was observed at 769 mg/kg/day in males and 904 mg/kg/day in females; the respective ELs were 104 mg/kg/day and 131 mg/kg/day. The U.S. Environmental Protection Agency (U.S. EPA) concluded that these findings in mice were an adverse compound-related effect suggesting that the high dose animals were unable to adequately utilize food. Cyantraniliprole caused some liver toxicity (decreased albumin levels, increased liver weight and alkaline phosphatase) in a oneyear feeding study in dogs at 6 mg/kg/day; the EL was 1 mg/kg/day. The U.S. EPA PP established a chronic oral reference dose (RfD) for cyantraniliprole of 0.01 mg/kg/day based on the EL from the chronic dog feeding study and an uncertainty factor of 100. This RfD value has not yet been adopted by the U.S. EPA Integrated Risk Information System (IRIS). Developmental/Reproductive Toxicity Cyantraniliprole caused some developmental toxicity in the offspring of pregnant rabbits, but not rats, exposed to this chemical during organogenesis at doses that also caused maternal toxicity. In the rat study, neither maternal nor developmental toxicity was seen up to a dose level of 1,000 mg/kg/day, the highest dose tested. In the rabbit, cyantraniliprole caused decreased mean fetal body weights at 250 mg/kg/day; the EL was 100 mg/kg/day. Maternal toxicity consisted of increased mortality, increased incidences of diarrhea, reduced and/or absent feces, decreased body weights, and decreased food consumption at 100 mg/kg/day; the EL was 25 mg/kg/day. In a multi-generation reproduction study in rats, cyantraniliprole was associated with dose-related decreases in organ weights (thymus and spleen) and pup body weights (F2 generation) at 136 mg/kg/day; the EL was 14 mg/kg/day. Parental toxicity consisted of increased thyroid weight and corresponding increases in the incidence of thyroid follicular epithelial cell hypertrophy/hyperplasia at 14 mg/kg/day; the EL was 1.4 mg/kg/day. Carcinogenicity Cyantraniliprole did not cause oncogenic effects in rat or mouse chronic feeding studies. This compound was also negative in a number of genotoxicity studies. The U.S. EPA classified cyantraniliprole as not likely to be carcinogenic to humans. Dietary Risk Assessment The U.S. EPA established tolerances for cyantraniliprole residues in or on a number of field, row and greenhouse crops (Federal Register 79: 6,826 33; February 5, 2014). The chronic population adjusted dose (cpad) for cyantraniliprole is 0.01 mg/kg/day and has the same basis as the RfD. The U.S. EPA estimated that the chronic dietary exposure to cyantraniliprole residues from all crops for which there are tolerances and drinking water would be 22 percent of the cpad for the general U.S. population, 44 percent for all infants less than one-year-old and 50 percent for children one to two years old, the highest exposed subgroup. 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. ccupational Risk Assessment The U.S. EPA reported the results of an extensive occupational risk assessment for inhalation exposures to cyantraniliprole from the labeled use of DuPont Exirel Insect Control and

26 Ms. Annette Marine 26. DuPont Verimark Insect Control to a variety of crops. Although the Exirel product tested positive for dermal sensitization, dermal exposures were not assessed because a systemic dermal toxicity endpoint was not identified for cyantraniliprole. For determining margins of exposure (MEs), the U.S. EPA compared estimated short-(1-30 days)/intermediate-term (1-6 months) inhalation exposures to a EL of 0.1 mg/l from a 28-day inhalation toxicity study in rats. o adverse systemic or portal of entry effects were observed in this study at the 0.1 mg/l dose level, which equates to a human equivalent dose (HED) of mg/kg/day. The estimated mixer/loader/applicator MEs for a variety of application sites (orchard crops, greenhouse plants, nursery plants, typical field crops, high acreage field crops) via several application methods (aerial, airblast, chemigation, groundboom, backpack sprayer, manually-pressurized handwand, mechanically-pressurized handgun, belly grinder, rotary spreader) ranged from 1,200 to 3,900,000. The U.S. EPA considered MEs of 30-fold or greater in these scenarios to provide adequate worker protection. Drinking Water/Groundwater Standards There are no chemical specific federal or ew York State drinking water/groundwater standards for cyantraniliprole or its degradates. Based on their chemical structure, these chemicals fall under the 50 micrograms per liter (µg/l) ew York State drinking water standard for unspecified organic contaminants (10 YCRR Part 5, Public Water Systems). The ew York State drinking water standard for the sum of unspecified organic contaminants and principal organic contaminants is 100 µg/l. Summary The available information on cyantraniliprole and the formulated products Exirel Insect Control and Verimark Insect Control indicates that they were not very acutely toxic or irritating in laboratory animal studies. Dermal sensitization risks from the Exirel product should be mitigated by the personal protective equipment required by the product label (long sleeved shirt and long pants, shoes plus socks, and chemical-resistant gloves). Cyantraniliprole caused some toxic effects, notably liver toxicity, in chronic and reproductive/developmental toxicity feeding studies with laboratory animals, but was not carcinogenic. The estimated dietary risks from exposure to cyantraniliprole treated crops and drinking water were within the range considered acceptable by the U.S. EPA. In addition, the expected exposure from the labeled use of the formulated products should not pose significant risks to workers. YS DH Recommendation Given the above, DH does not object to the registration of DuPont Exirel Insect Control and DuPont Verimark Insect Control in the state on the basis of direct health risks from worker use or dietary exposures. ECLGICAL EFFECTS ASSESSMET: The following assessment was produced by staff of the Department s Division of Fish, Wildlife & Marine Resources Bureau of Habitat (BH):