Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 1 of 45 **UNITED STA TES ENVIRONMENTA**  **L PROTECTION A GENCY**  WA SHINGTON, D.C. 20460 **OFFICE OF CHEMICAL SAFETY AND**

**POLLUTION PREVENTION MEMORANDUM**  Date: 25 - APR - 2012 Subject: Cyazofamid. Petition for the Establishment of Permanent Tolerances and

Registration for Use on Basil, Succulent Beans, the Fruiting Vegetable Group 8 - 10, the Leaf y Greens Subgroup 4A, and the Tuberous and Corm Vegetable Subgroup 1C . Summary of Anal yt ical Chemistry

and Residue Data. PC Code: 085651 DP Barcode: D 396051 MRID No s .: See Below Registration No. : 71512 - 3 Petition No.: 1E7929 Regulatory Action: Section 3 Registration Assessment Type: Single Chemica l/Aggregate Case No.: NA T XR No.: None CAS No.: 120116 - 88 - 3 Decision No.: 456373 40 CFR 180. 601 From: Nancy

Dodd, Chemist Risk Assessment Branch III (RAB3) Health Effects Division ( HED) (7509P) Through: Leung Cheng, Senior Chemist

RAB3/HED (7509P) To: Barbara Madden/Laura Nollen, RM #5

Risk Integration, Minor Use and Emergency Response Branch ( RI MUERB) Registration Division ( 7505P ) **MRID Summary Table MRID No.**  **Study Type Comments**  48629401 860.1500 New DER; 48629401.der.doc 48629402 860.1500 New DER; 48629402.der.doc 48629403 860.1500 New DER; 48629403.der.doc 48629404 860.1500 New DER; 48629404.der.doc 48629405 860.1500 New DER; 48629401.der.doc 46537730 860.1520 No DERCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 2 of 45 **Table of Contents** Background ................................ ................................ ................................ ................................ ..... 3 Executive Summary ................................ ................................ ................................ ........................ 3 Pre - Registration Data Needs ................................ ................................ ................................ ....... 5 Condition - of

- Registration Data Needs ................................ ................................ ....................... 5 Tolerance Considerations ................................ ................................ ................................ ................ 5 Analy tical Method ................................ ................................ ................................ ...................... 5 Recommended Tole rances ................................ ................................ ................................ .......... 5 International Harmonization ................................ ................................ ................................ ....... 6 Revisions to Petitioned - For Tolerances ................................ ................................ ...................... 6 Residue Profile ................................ ................................ ................................ ................................ 7 Residue Chemistry

Guidelines ................................ ................................ ................................ ........ 9 Dire ctions for Use (860.1200) ................................ ................................ ................................ .... 9 Nature of the Residue (860.1300/1850) ................................ ................................ .................... 12 Residue Anal yt ical Methods (860.1340) ................................ ................................ .................. 14 Multiresidue Methods (860.1360) ................................ ................................ ............................ 15 Storage Stability

(860.1380) ................................ ................................ ................................ ..... 16 Water, Fish, and Irrigated Crops (860.1400) ................................ ................................ ............ 17 Food Handling (860.1460) ................................ ................................ ................................ ........ 17 Meat, Milk, Poultry , and Eggs (860.1480) ................................ ................................ ............... 17 Crop Field Trials (860.1500) ................................ ................................ ................................ .... 19 Processed Food and Feed (860.1520) ................................ ................................ ....................... 28 Rotational Crops (Field; 860.1900) ................................ ................................ .......................... 29 Tolerance Derivation ................................ ................................ ................................ .................... 29 Appendix A. Field Trial Geographic Distribution ................................ ................................ ....... 42 Appendix B: International Residue L imits ................................ ................................ ................... 44 Appendix C: Chemical Names and Structures of Cyazofamid and Identified Metabolites ......... 45Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 3 of 45 **Background** The Interregional Research Project No. 4 (IR - 4) has proposed e stablishment of p ermanent tolerances for residues of the fungicid e cyazofamid [4 - chloro - 2 - cyano -N , N - dimethyl - 5 - (4 - methylphen yl ) - 1 H

- imidazole - 1 - sulfonamide] and its metabolite CCIM [4 - chloro - 5 - (4 - methylphen yl ) - 1 H

- imidazole - 2 - carbonitrile] on basil (fresh and dried), succulent beans, succulent shelled beans, the fruiting vegetable group 8 - 10, the leafy greens subgroup 4A , and the tuberous and corm vegetable subgroup 1C . These proposed new uses are to be added to the Ranman 400SC label (EPA Reg. No. 71512 - 3). Ranman 400SC is a soluble concentrate formulation which contains 3.33 lb active ingredient (ai) per gallon (400 grams ai/liter; 34.5% ai) . Cyazofamid is a fungicide which belongs to a novel chemical class based on the cyanoimidazole moiety . Cyazofamid is a broad spectrum fungicide active against oomycet e fungi (such as Phytophthora, Plasmopara, Pseudoperonospora, and Pythium ) and Plasmodiophoromycetes ( Plasmodiospora brassicae ). It specificall y interferes with the cytochrome bc 1 complex (ubiquinol cy

tochrome c oxidoreductase) in the mitochondrial respir atory chain of oomycetes fungi. Permanent tolerances are established in 40 CFR §180.601 on various raw agricultural commodities (RACs) at levels ranging from 0.02 ppm on potato to 12.0 ppm on turnip greens and the Brassica leafy

greens subgroup 5 B. A t olerance with regional registration is established on grape at 1.5 ppm. Time - limited tolerances under a Section 18 have been established on dried basil at 144 ppm and fresh basil at 12 ppm; these tolerances will expire on 12/31/14. No tolerances have bee n established on livestock commodities. Ranman® 400SC can be applied using ground, aerial, or sprinkler irrigation equipment. Multiple foliar applications can be made to all proposed crops. T omatoes grown for transplant and basil can be grown in the greenhouse. A soil drench can be applied to fruiting vegetables at transplant or to tomatoes in the greenhouse. A band or soil drench application can be made to the leafy greens subgroup 4A at transplant or seeding. The tuberous and corm vegetable subgroup can be treated at - planting, in - furrow at planting, or lay - by /hilling. Maximum application rates per crop growing season are 0.43 lb ai/A for beans (succulent podded and succulent shelled), fruiting vegetables, and the leafy greens subgroup 4A; 0.7 lb ai/A for basil, and 0.71 lb ai/A for the tuberous and corm vegetable subgroup 4A. The preharvest intervals are 0 day s for basil, beans (succulent podded and succulent shelled), fruiting vegetables, and the leafy greens subgroup 4A, and 7 day s for the tuberous and corm vegetable subgroup 1C. The plantback interval is 0 days for crops on the label and 30 day s for other crops. The label indicates that Ranman 400SC should be tank mixed with an organosilicone surfactant, non - ionic surfactant, or a blend of an organosilicone and a non - ionic surfactant. **Executive Summary** T he Interregional Research Project No. 4 (IR - 4) has proposed e stablishment of p ermanent tolerances for residues of the fungicide cyazofamid and its metabolite CCIM on basi l (fresh and dried), succulent beans, succulent shelled beans, the fruiting vegetable group 8 - 10, the leafyCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 4 of 45 greens subgroup 4A, and the tuberous and corm vegetable subgroup 1C. Ranman 400 SC is a suspension concentrate formulation. Cyazofamid has limite d sy stemic activity . It can be applied using ground, aerial or sprinkler irrigation equipment. It can be applied to the soil and as multiple foliar applications. It can be applied to basil grown in the greenhouse and to tomato transplants in the greenho use. Maximum application rates per crop growing season are 0.43 lb ai/A for beans (succulent podded and succulent shelled), fruiting vegetables, and the leafy

greens subgroup 4A; 0.7 lb ai/A for basil, and 0.71 lb ai/A for the tuberous and corm vegetable subgroup 4A. The preharvest intervals are 0 day s for basil, beans (succulent podded and succulent shelled), fruiting vegetables, and the leafy greens subgroup 4A, and 7 day s for the tuberous and corm vegetable subgroup 1C. The residues of concern for the tolerance expression and risk assessment are parent and the metabolite CCIM in treated plants and parent only in rotational crops. No residues are expected to occur in livestock commodities. Adequate enforcement methods are available , including a multiresidue method (Protocol D) and a high performance liquid chromatograph y/ultraviolet detection ( HPL C/UV ) method with a confirmatory

method ( liquid chromatography /tandem mass spectrometric detection; LC/MS/MS). The methods determine cyazofamid and the metabolite CCIM. The limit of quantitation (L OQ) of the HPL C/UV and L C/MS/MS methods is 0.01 ppm for each analy te. Adequate storage stability data are available to support the storage intervals of the field trials and processing studies. Provided the requested revisions are made to the Ranman 400 SC label, the field trials are adequate to establish tolerances on all the proposed commodities at levels recommended in Table 1 below. Detectable residues may occur in food. Field trial decline studies sho w that residues in agricultural commodities decline with increasing preharvest intervals. Adequate pro cessing studies are available. The potato and tomato processing studies are adequate to indicate that combined residues of cyazofamid and CCIM are not likely to concentrate in processed commodities. The proposed and registered uses fall under 40 CFR § 180.6( a)(3) with respect to livestock commodities , i.e., there is no reasonable expectation that finite residues will occur in livestock commodities. Based on a study

on confined accumulation in rotational crops, cyazofamid (parent) is expected to be present at a level o f less than 0.01 ppm at a plant back interval of 30 d ay s. The rotational crop plant back interval of 0 day s for crops which are on the l abel and 30 day s for other crops is appropriate. **R egulatory R**  **ecommendations** Provided the revisions to the Section B/label are made as requested below (in the Pre -Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 5 of 45 Registration Data Needs section), the available residue chemistry data are adequate to suppo rt registration of the crop/crop group commodit ies requested b y the petitioner at the tolerance levels recommended in Table 1 below (in the Recommended Tolerances section). **P re**  **- Registration Data Needs**  Directions for Use (860.1200) The Ranman 400 SC lab el should be amended to prohibit applications to cowpea grown for livestock feeds because no residue data are available for cowpea forage and hay . The statement “Do not appl y to cowpea used for livestock feed” should be added to the label. Cowpea is a su cculent shelled bean. The label indicates that Ranman 400 SC should be tank mixed with an organosilicone surfactant, non - ionic surfactant, or a blend of an organosilicone and non - ionic surfactant. The label should be revised to specify

that an organosil icone surfactant can be used on basil, snap beans, lima beans, pepper, potato, spinach and tomato, and either a nonionic surfactant or an organosilicone surfactant can be used on head and leaf lettuce. Meat, Milk, Poultry , and Eggs (860.1480) Tolerances for residues of cyazofamid in poultry and swine commodities are not required provided that application to cowpea used for livestock feed is prohibited on the label. **Condition -**  **of**

**- Registration Data Needs**  None **Tolerance Considerations Analytical Method**  Adequate enforcement method s are available to determine residues of cyazofamid and its metabolite CCIM in lettuce, basil, snap bean, lima bean , pepper, potato, spinach, and tomato . An enforcement method for non - fatt y commodities is FDA’ s Multiresidue Protocol D (without cleanup), which completely recovers (>80% recovery) cyazofamid and metabolite CCIM. In addition, the HPL C/UV method (MRID 45409020; revised in MRID 46550401) is acceptable for use as a single analy

te enforcement method p rovided a confirmatory method such as the LC/MS/MS method is used. **Recommended Tolerances** Tolerances are established in 40 CFR §180.601 with the following tolerance expression, as per the Steve Knizner memo dated 5/27/09: Tolerances are established fo r residues of the fungicide cyazofamid, including its metabolitesCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 6 of 45 and degradates, in or on the commodities in the following table. Compliance with the tolerance levels specified in the following table is to be determined b y measuring onl y the sum of 4 - chl oro - 2 - cyano -N , N - dimethyl - 5 - (4 - methylphen yl ) - 1 H - imidazole - 1 - sulfonamide and its metabolite, 4 - chloro - 5 - (4 - methylphenyl) - 1 H - imidazole - 2 - carbonitrile, calculated as the stoichiometric equivalent of cyazofamid, in or on the following commodit i es . HED recomm ends for establishment of the tolerances on the commodities in Table 1 below using the same tolerance expression as above : **Table 1**  **. Tolerance Summary for C**  **yazofamid .**  Commodity Established/Proposed Tolerance (ppm) Recommended

Tolerance 1 (ppm) Comments (correct commodity

definition) Bean, succulent 0.4 0.5 Bean, succulent, shelled 0.07 0.08 Leafy greens subgroup 4A 9.0 10 Basil, fresh leaves 30 30 Basil, dried leaves 80 90 Vegetable, tuberous and corm, subgroup 1C 0.02 0.0 2 Vegetable, fruiting, group 8 - 10 0.40 0.9 1 See “Revisions to Petitioned - For Tolerance” section. When the above tolerances are established, the existing tolerances on spinach, potato, the fruiting vegetable group 8 and okra can be removed as requested by the petitioner. **International Harmonization** There are no Codex or Mexican maximum residue limits (MRL s) on the proposed crops . Canada has a tolerance at 0.02 ppm on potatoes, which is the same level as the US tolerance on the crop group (vegetable, tuberous and corm, subgroup 1C). Canada also has a tolerance of 0.2 ppm on tomatoes, which is less than the recommended US toleran ce of 0.9 ppm on the crop group (vegetable, fruiting, group 8 - 10). The tolerance definition for the US and Canada are the same. Both the US and Canada include parent and the metabolite , 4 - chloro - 5 - (4 - methylphenyl) - 1 H - imidazole - 2 - carbonitrile, in the t olerance expression. **Revisions to Petitioned -**  **For Tolerances** Bean, succulent: HED recommends increasing the proposed tolerance from 0.4 ppm to 0.5 ppm for succulent bean. The Organization for Economic Cooperation and Development (OECD) tolerance calculator gave a value of 0.5 for snap bean when average field trial values were entered (n = 8). Bean, succulent, shelled: HED recommends increasing the proposed tolerance for succulent shelled bean from 0.07 ppm to 0.08 ppm since the OECD t olerance calculator gave a value of 0.08 ppm for lima bean when average field trial va lues were entered (n = 6).Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 7 of 45 Leafy greens subgroup 4A: HED recommends increasing the proposed tolerance for the leafy greens subgroup 4A from 9 ppm to 10 ppm. The established tolerance on spinach is 9.0 ppm . The representative commodities for the leafy greens subgroup 4A are head lettuce, leaf lettuce, and spinach. The OECD calculator gave values of 4 ppm for head lettuce, 8 ppm for leaf lettuce, and 10 ppm for spinach. The highest value of the representative commodities is 10 ppm. Basil, dried leaves: HED recommends increasing the proposed tolerance for dried basil leaves from 80 ppm to 90 ppm. T he OECD calculator value for dried basil leaves is 90 ppm when average field trial values were entered (n = 4). Vegetable, fruiting, group 8 - 10: HED recomm ends increasing the proposed tolerance for the fruiting vegetable group 8 - 10 from 0.40 to 0.9 ppm. A tolerance of 0.40 ppm is established for the fruiting vegetable group 8. The representative commodities for Crop Group 8 - 10 are tomato, standard size, an d one cultivar of small tomato; bell pepper and one cultivar of small nonbell pepper . The residue data on the fruiting vegetable group 8 support the fruiting vegetable group 8 - 10. The OECD calculator using average field trial values gives values of 0.2 ppm for tomato (n = 16) , 0.4 ppm for bell pepper (n = 6) and 0.9 ppm for nonbell pepper (n = 3). The highest value of the representative commodities is 0.9 ppm. **Residue Profile Table 2**  **. Test Compound Nomenclature.**  Com pound Chemical Structure

Common name Cyazofamid Com pany experimental name N/A IUPAC name 4 - chloro - 2 - cyano -N, N - dimethyl - 5 -

p - tolylimidazole - 1 - sulfonamide CAS name 4 - chloro - 2 - cyano -N,N - dimethyl - 5 - (4 - methylphenyl) - 1 H - imidazole - 1 - sulfonamide CAS registry number 120116 - 88 - 3 End - use product (EP) Ranman® 400SC Agricultural Fungicide (EPA Reg. No. 71512 - 3) Com pound Chemical Structure of metabolite

Common name CCIM IUPAC name 4 - chloro - 5 - p - tolylimidazole - 2 - carbonitrile CAS name 4 - chloro - 5 - (4 - me thylphenyl) - 1 H - imidazole - 2 - carbonitrile

N N C H3 Cl CN S O 2 N ( C H

3 ) 2

N H N C H3 Cl CNCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 8 of 45 **Ta ble 3**  **. Physicochemical Properties of the Technical Grade Cyazofam** **id.** Parameter Value Reference Melting point (°C) 152.7 PMRA Regulatory Note REG2006 - 05 on Cyazofamid, 12/6/06 pH 4.9 e - Pesticide Manual, 13 th Edition Density at 20 °C (g/mL) 1.446 Water solubility (at 20 °C) pH Solubility (mg/L) REG2006 - 05 5 7 9 0.121

0.107 0.109 Solvent solubility (at 21.2°C) Solvent Solubility (g/L) Acetone Ethyl acetate Methanol Dichloromethane Toluene Hexane n - Octanol Acetonitrile 2 - Propanol 43.1

16.19 1.74 94.82 6.0 0.03 0.04 29.446 0.43 Vapor pressure at 25°C <1.33 x 10 - 5 Pa Dissociation constant (pKa) Does not dissociate in water. No pK a in the pH range of 2 - 12. Octanol/water partition coefficient Log KOW = 3.2 KOW = 1.585 x 10 3 UV/visible absorption spectrum pH Λ max (nm) 2 7 10 285

279 287 Cyazofamid technical is a solid at room temperature with low vapor pressure. The formulation is a suspension concentrate. Detectable residues may occur in food. Field trial decline studies show that residues in agricultural commodities decline with increasing preharvest intervals. According to EPA’s Pesticide Fact Sheet (September 2004), cy azofamid has limited sy stemic activity so it is used as a protectant fungi cide applied by ground or aerial spray . Exposure to surface water is possible through water runoff, soil erosion, or spray drift.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 9 of 45 **Residue Chemistry Guidelines Directions for Use**  **(860.1200) Table**  **4. Summ**  **ary of Proposed**  **Directions for Use of Cyazofam** **id .**  Applic. Timing, T ype, and Equip. Form

ulati on [EPA Reg. No.] Applic.

Rate (lb ai/A) Max. No.

Applic. per Season Max. Seasonal

Applic. Rate (lb ai/A) PHI

(days) Use Directions and

Limitations * **Basil** Post emergence. Foliar broadcast sprays using ground , aerial, or sprinkler irrigation equipment. Can be grown in a greenhouse. Ranman

400SC [71512 - 3] 0.07 2 -

0.078 9 0.7 0 Normal water volume is 50 - 75 gals water per acre. For downy mildew on basil, make applications on a 7 to 10 day schedule. **Beans, Succulent Podded and Succulent Shell ed**  Cicer arietinum (chickpea, garbanzo bean); Lupinus spp. (including sweet lupine, white sweet lupine, white lupine, and grain lupine). Phaseolus spp. (including kidney bean, lima bean, mung bean, navy bean, pi nto bean, snap bean, and waxbean); Vicia faba (broad bean, fava bean); Vigna spp. (including asparagus bean, blackeyed pea and cow

pea) Post emergence. Foliar broadcast sprays using ground , aerial, or sprinkler irrigation equipment . Ranman

400SC [71512 - 3] 0.07 2 6 0.43 0 Normal water volumes are 20 - 60 gals water per acre. For downy mildew on lima beans: Make applications on a 7 to 10 day schedule. For cottony leak control: Make the initial application at full bloom (1 st pods) and repeat on a 7 - 14 - day

schedule. For Phytophthora blight control: Make the 1 st application at 100% bloom - pin pod development and a 2 nd application at late pin small pod development and repeat every seven days. **Fruiting Vegetables (Crop Group 8**  **- 10)**  African eggplant; bush tomato; bell pepper; cocona; currant tomato; eggplant; garden huckleberry; goji berry; groundcherry; martynia; naranjilla; okra; pea eggplant; pepino; nonbell pepper; roselle; scarlet eggplant;Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 10 of 45 sunberry; tomatillo; tomato; tree tomato; cultivars, varieties, and/or hybrids of these Post emergence. Broadcast foliar or soil drench to the base of the plants at transplanting or in transplant water . Ground , aerial, or sprinkler irrigation equipment. Tomatoes for transplant can be grow n in the greenhouse. A soil drench can be applied to tomatoes in the greenhouse. Ranman

400SC [71512 - 3] 0.054 -

0.072 Soil drench: 0.078 lb ai/100 gals water 6 0.43 0 Normal water volumes are 30 - 60 gals water per acre. For late blight control, make ap plications on a 7 to 10 day schedule. For Phytophthora blight control, apply to the base of the plants at the time of transplanting. Alternatively, apply in transplant water at the time of transplanting. Apply 0.07 2 lb ai/A in transplant water in a wate r volume of at least 50 gals/A for the initial application . Apply on a 7 to 10 day schedule. Tomato Greenhouse Transplant Production: For control of Pythium spp., make a single fungicide application to the seeding tray at the time of planting or at any time thereafter up until 1 week before transplanting. Apply the fungicide solution as a drench to thoroughly wet the growing medium (1 pt of solution per square foot if the growing medium is 4 inches deep). Do not use a surfactant with this drench applic ation. **Leafy Greens, Crop Subgroup 4A** Amaranth (leafy amaranth, Chinese spinach, tampala); arugula (Roquette); chervil; edible - leaved chrysanthemum; garland chrysanthemum; corn salad; garden cress; upland cress (yellow rocket, winter cress); dandelion; dock (sorrel); endive (escarole); lettuce (head and leaf); orach; parsley; garden purslane; winter purslane; radicchio (red chicory); spinach; New Zealand spinach; vine spinach (Malabar spinach, Indian spinach). Post transplant; Post - seeding; P ost emergen ce. Foliar broadcast or soil drench Ranman

400SC [71512 - 3] 0.07 2 ** 6 0.43 0 Downy mildew: Apply at 7 - 14 - day

intervals. Py thium: Make first application as a band to the soil as a directed, post - transplant or post seeding application;Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 11 of 45 band s pray usi ng ground , aerial, o r sprinkler irrigat i on equipment . alternatively, apply in transplant water at the time of transplant as a soil drench in at least 50 gals water per acre. Apply at 7 to 10 day intervals. Normal water volumes are 20 - 60 gals water per acre. **Tuberous and Corm Vegetables, Crop Subgroup 1C** Arracacha; arrow

root; Chinese artichoke; Jerusalem artichoke; edible canna; bitter cassava; sweet cassava; chayote (root); chufa; dasheen (taro); ginger; leren; potato; sweet potato; tanier; turmeric; yam bean; true yam Post emergence foliar sprays using ground , aerial, or sprinkler irrigation equipment. Can also be at planting, in furrow at planting, or lay - by / hilling Ranman

400SC [71512 - 3] Foliar:

0.036 - 0.072 ** At planting: 0.42 fl oz per 1000 linear feet (0.16 lb ai/A based on a 36” row spacing) Lay - by/ Hilling: 0.07 2 10 0.72 ** 7 Normal water volumes are 20 - 50 gals water per acre. For foliar blight, make applications on a 7 to 10 day schedule. For tuber and corm rot control, make the last 2 to 3 applications prior to harvest at the rate of 0.072 lb ai/A applied weekly. For pink rot, Phythium root and crown rot control at planting, apply 0.42 fl oz product per 1000 linear foot of row in - furrow at planting using a minimum of 5 gals wat er per acre. Apply in a 6 - 8 inch band directly over the seed pieces prior to furrow

closure. Mefenoxam can be added as a tank mix. For additional control of Py thium root and crown rot, in combination with an at - planting, in - furrow application, apply as a broadcast spray at 0.072 lb ai/A in a minimum of 20 gals of finished spray solution per acre at hilling. * Use directions and limitations:Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 12 of 45 The plantback interval is 0 days for crops on the label and 30 days for other crops. Spray volumes will usually range from 20 - 100 gals per acre for dilute sprays and 5 - 10 gals/A for concentrate sprays and aerial sprays. Aerial sprays should be made in a minimum of 5 gals of water per acre. Alternate sprays of Ranman 400SC with a fungicide with a different mo de of action ; d o not make more than three consecutive applications of Ranman 400SC followed by at least three applications of fungicides having different mo des of action before ap plying additional RANMAN 400SC. Ranman 400SC should be t ank mix ed with an organosilicone surfactant, non - ionic surfactant, or a blend of an organosilicone and a non - ionic surfactant. ** 2.75 fl oz product /A = 0.0715 lb ai /A and 27.5 fl oz product /A= 0.715 lb ai /A . HED rounds up to 0.072 and 0.72 , respectively, as per EPA’s Hot Sheet # 10. Conclusions . Provided the revisions given below are made, the Ranman 400SC label is adequate to allow evaluation of the residue data relative to the proposed use. The Ranman 400 SC label should be amended to prohibit appl ications to legumes grown for livestock feeds because no residue data are available for cowpea forage and hay . The statement “Do not appl y to cowpea used for livestock feed” should be added to the label. Cowpea is a succulent shelled bean. An organosilicone surfactant (OSS) was used in all field trials on basil, snap beans, lima beans, pepper, potato, and spinach and on several field trials on tomato. Either a nonionic surfactant (NI S) or OSS w as used in all field trials on head lettuce and leaf lettuce. The label indicates that Ranman 400 SC should be tank mixed with an organosilicone surfactant, non - ionic surfactant, or a blend of an organosilicone and non - ionic surfactant. The label should be revised to specify that an organosilicone surfactant can be used on basil, snap beans, lima beans, pepper, potato, spinach and tomato, and either a nonionic surfactant or an organosilicone surfactant can be used on head and leaf lettuce. **Nature of the Residue (860.1300/1850)**  Amelia Acierto, 2/1 8/04, DP# D298915, Cyazofamid

– Meeting Report of the Metabolism Assessment Review Committee (MARC). Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical Chemistry and Residue Data ; Plants: 45409015.der, 45409016.der, 45409017.der; Goat: 45409018.der; Hen: 45409019.der; Rotational Crops: 45409036.der. Breann Hanson, 8/3/10, DP# D376500, **Cyazofamid** . Hu man Health Risk Assessment for Proposed Section 18 Use on Basil.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 13 of 45 **CHEMICAL: CYAZOFAMID Date**  : 18 - February - 2004 **Table 5**  **. Residues of Concern in Plants, Livestock, Rotational Crops, and Water**  **Matrix For Risk Assessment**  **For Tolerance Expression** Plants Parent and CCIM Parent and CCIM Livestock No decision ( For future cattle feeding studies, the MARC recommended that the petitioner analyze parent, CCIM, CCBA, and CCBA - cysteine conjugate.) No decision Rotational crops Parent only Parent only Water Parent, CCIM, CCIM - AM, and CTCA N/A Nature of the Residue - Plants The nature of the residue in basil, lettuce, snap bean, lima bean , pepper, potato spinach, and tomato is adequatel y understood based on previously submitted metabolism studies conducted on grape, potato, and tomato . The results of the m etabolism studies in plants indicate d that the parent and CCIM are the major residues (>10% TRR). There are no specific toxicity concerns for all other minor metabolites. F or the risk assessment and t olerance expression, the parent cyazofamid and the metabolite CCIM are the residues of concern in primary (treated) plants. Nature of the Residue

– Livestock Provided that application to cowpea used for livestock feed is prohibited on the label, the registered and proposed uses of cyazofamid fall under 40 CFR §180.6(a)(3) with respect to livestock commodities , i.e. , there is no reasonable expectation that finite residues will occur in livestock commodities. G oat and hen metabolism studies have been reviewed; however, residues of concern in livestock commodities have not been identified (A. Acierto, 2/18/04 , DP# D298915). B ased on the available goat metabolism s tudy , the MARC determined that the following metabolites should be anal yz ed for future cattle feeding studies: cyazofamid, CCIM, CCBA (4 - (4 - chloro - 2 - cyanoimidazol - 5 - yl )benzoic acid , and the CCBA - cy steine conjugate. Provided that application to cowpea used for livestock feed is prohibited on the label, there are no poultry or swine f eedstuffs associated with registered or proposed uses ( Table 1 Feedstuffs , June 2008) . Confined Accumulation in Rotational Crops A confined accumulation in rotational crop study was previousl y submitted in conjunction with an earlier petition (PP#1F06305 ; DP# D285680, A. Acierto, 2/20/04 ; 45409036.der). The results of these data showed that cyazofamid and structurally related metabolites are each expected to be present at a level less than 0.01 ppm at a plantback interval of 30 day s. For the risk assessm ent and tolerance expression, parent is the onl y residue of concern in rotational crops. Therefore, the rotational crop plant

back interval (PBI) of 0 day s for crops which are on the label and 30 day s for other crops is appropriate.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 14 of 45 **Residue Analytical Methods**  **(860.1340)** Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical Chemistry and Residue Data ; Plants: 45409022.der, 45409020.der. Breann Hanson, 8/3/10, DP# D376500, Cyazofamid . Human Health Risk Assessment for Proposed Section 18 Use on Basil. Elizabeth Kolbe, 10/22/03, DP# D286108, PP# 3F6595. Cyazofamid on Potatoes, Tomatoes, Cucurbit and Grapes. Tolerance Method Review and Multi -Residue Method Review. PC Code 085651 (MRID#: 454090 - 33, 456385 - 08, 454090 - 34, 454090 - 32, 454090 - 20, 45 4090 - 22) ; ACB # B02 - (58 - 61). Elizabeth Kolbe, 2/27/06, DP# D326164, PP# 3F6595. Review of Resubmitted Analy tical Method for Cy azofamid and its Metabolite CCIM in Crops. PC Code 085651 (MRID#: 46550401); ACB Project # B06- 13. Enforcement Method

s – Plants Adequate enforcement methodology is available to enforce the proposed tolerances. Cyazofamid and metabolite CCIM are completely recovered (>80% recovery) in non - fatty commodities using FDA’s Multiresidue Protocol D (without cleanup) (MRID 45409022) . Tomatoes were fortified with cyazofamid at 0.05 ppm and with CCIM at 0.1 ppm; recoveries were adequate. The multiresidue method can be used as an e nforcement method. In addition, an HPL C/UV method (MRID 45409020 ; revised in MRID 46550401 ) is acceptable f or use as a single anal yt e enforcement method provided a confirmatory method such as the LC/MS/MS method discussed below is used. An independent laboratory validation of the HPL C /UV method (MRID 45409020) was conducted on tomatoes; adequate recoveries wer e obtained on tomatoes for cyazofamid and CCIM at an LOQ of 0.01 ppm for each anal yt e. Successful radiovalidation of the HPL C/UV method was conducted on samples from the grape and potato metabolism studies (MRIDs 45409016 and 45409017). Data Collection Method

– Plants 48629401.der (includes MRID 48629405) : Lettuce (head and leaf) 48629402.der: Basil 48629403.der: Snap bean (a succulent bean) 48629404.der : Lima bean (a succulent shelled bean) S amples of lettuce, basil, snap bean and lima bean were anal yz ed for residues of cyazofamid and its metabolite CCIM using the LC/MS/MS method ; the method is a modified version of the method in MRID 45409020. The limits of quantitation ( LOQ s; determined as the lowest level of method validation, LLM V) were 0.01 ppm for each anal yt e in head lettuce, leaf lettuce, snap bean, lima bean, and fresh basil and 0.1 ppm for each analy te in dried basil. The method was adequate for data collection based on acceptable method validation and concurrent recovery data. Th e fortification levels used in concurrent method recovery and method validation were adequate to bracket expected residue levels. C oncurrent recoveries and r esidues in the treated samples were not corrected for residues in controls. The analy tical method does not specify conversion of metabolite residues to parent equivalents; therefore, quantifiable residues of CCIM were converted to parent equivalents by the study reviewer using a molecular weight conversion factorCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 15 of 45 of 1.49 (MW of cyazofamid 324.79 ÷ MW of CCIM 217.65). Field trials on pepper, spinach, tomato and potato were previousl y reviewed. The data collection method for pepper and spinach was the LC/MS/MS method. The data collection method for tomato and potato was the HPL C/UV method. All L OQs w ere 0.01 ppm for each anal yt e in each crop. C onclusion s . The data collection and enforcement method s are adequate to determine residues of cyazofamid and its metabolite CCIM in lettuce, basil, snap bean, lima bean, pepper, potato, spinach, and tomato. An enforcement method for non - fatty commodities is FDA’s Multiresidue Protocol D (without cleanup), which completely recovers (>80% recovery) cyazofamid and metabolite CCIM. In addition, an HPL C/UV method (MRID 45409020; revised in MRID 46550401) is acc eptable for use as a single anal yt e enforcement method provided a confirmatory method such as the L C/MS/MS method is used. The data collection method ( LC /MS/MS) , a modified version of the method in MRID 45409020, is adequate for determination of cyazofamid and CCIM in residue samples, based on adequate recoveries and limits of quantitation, which were 0.01 ppm for each anal yt e in head lettuce, leaf lettuce, snap bean, lima bean, fresh basil , pepper, and spinach and 0.1 ppm for each anal yt e in dried basil . The HPL C/UV method is adequate for determination of residues of cy azofamid and CCIM in potato and tomato at the LOQ of 0.01 ppm for each anal yt e. **Multiresidue Methods (860.1360)**  Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical Chemistry and Residue Data ; 45409022.der E lizabeth Kolbe, 10/22/03, DP# D286108 , PP# 3F6595. Cyazofamid on Potatoes, Tomatoes, Cucurbit and Grapes. Tolerance Method Review and Multi -Residue Method Review. Cyazofamid and its metabolite CCIM were anal yz ed according to the FDA Multi r esidue Method (MRM) Test guidelines in PAM , Volume I , Appendix II (1/94). Testing using Protocols A and B is not required because cyazofamid and CCIM do not have an N - methylcarbamate structure and are not acid or phenol compounds. Using Protocol C, injections of cyazofamid and CCIM yi elded adequate respons es to several of the Section 302 GL C sy stems. Cyazofamid and CCIM were completel y recovered (>80% recovery) using Protocol D (without cleanup). Cyazofamid was partiall y recovered (50 - 80% recovery) using Protocols E and F. CCIM was not furthe r tested with Protocols E and F because <30% of CCIM was recovered from the Florisil column cleanup tests. Conclusion s . Adequate multiresidue methods data (MRID 45409022) have been submitted. T he FDA Multiresidue Method Protocol D (without cleanup) meets the requirement of OCSPP 860.1360 for non - fatty

commodities . R esidues of cyazofamid and CCIM are completely recovered (>80%Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 16 of 45 recovery) from non - fatt y commodities through the FDA Multiresidue Method Protocol D (without cleanup). In MRID 45409022, tomatoes were fortified with cyazofamid at 0.05 ppm and with CCIM at 0.1 ppm; recoveries using Protocol D were adequate. The multiresidue method can be used as an enforcement method. The multiresidue methods data have been forwarded b y the Anal yt ical Chemistry Branch of the Biological and Economic Analy sis Branch ( ACB/BEAD ) to FDA (D286108, E. Kolbe , 10/22/03) . **Storage Stability (860.1380)**  48629401.der (includes MRID 48629405) : Lettuce (head and leaf) 48629402.der: Basil 48629403.der: Snap bean 48629404.der: Lima bean Storage stability

data generated concurrentl y with the field trial studies are reported below. **Table 6**  **. Summary of Storage Conditions and Durations of Sam ples from Crop Field Trial Studies.**  Matrix Storage

Tem perature (°C) Actual Storage

Duration 1 Interval of Demonstrated Storage Stability (days) 2 ,3 Basil , fresh

- 20 8 - 284 days (0.3 - 9.3 months) Residues of cyazofamid were stable in/on fresh basil

stored frozen for up to 284 days (9.3 months) . Residues of CCIM in/on fresh basil declined by 46% after 284 days (9.3 months) of freezer storage. Basil, dried

- 20 155 - 299 days (5.1 - 9.8 months) Residues of cyazofamid and CCIM w ere reasonably stable

in/on dried basil stored frozen for up to 297 days (9.8 mo nths) . Beans, lima

- 20 63 - 147 days (2.1 - 4.8 months) Residues of cyazofamid and CCIM w ere stable in/on lima

beans stored frozen for up to 140 days (4.6 months) . Beans, snap 3

- 20 861 - 946 days (28.3 - 31.1 months) Residues of cyazofamid and CCIM w ere stable in/on snap

beans stored frozen for up to 887 days (29.2 months) . Lettuce , h ead

- 20 to - 8.9 208 - 634 days (6.8 - 20.8 months) Residues of cyazofamid and CCIM we re stable in /on leaf lettuce stored frozen for up to 634 days (20.8 months) . Lettuce , leaf

- 20 to - 8.9 251 - 624 days (8.3 - 20.5 months) 1 Storage duration is from collection to analysis. Samples were analyzed within 0 - 1 day of extraction. 2 Storage stability data were generated concurrently with the field trial study. 3 No 0 - day data were provided. 4 Pods with seeds Conclusions . The available storage stability data are adequate to support the storage durations and conditions of the field trial s amples . Except for residues of the metabolite CCIM in fresh basil, the data are adequate to conclude that residues of cyazofamid and CCIM in the field trial samples were stable during frozen storage. Residues of CCIM in fresh basil declined b y 46% after 284 day s (9.3 months) of freezer storage ; therefore, residues in fre sh basil in the field trials were corrected for loss of CCIM in storage .Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 17 of 45 **Water, Fish, and Irrigated Crops (860.1400)**  There are no proposed uses that are relevant to this guideline topic. **Food Handling (860.1460)**  DER Reference List There are no proposed uses that are relevant to this guideline topic. **Meat, Milk, Poultry, and Eggs (860.1480)**  Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical Chemistry and Residue Data ; 45409018.der. Livestock feed items are associated with the registered uses on carrots and potatoes and with the proposed uses on potato (as part of the tuberous and corm veget able subgroup 1C ) and cowpea. Livestock feed items are carrot culls, potato culls, processed potato waste, and c owpea seed, forage, and hay . Ther e are no other proposed crops that are associated with significant livestock feed items ( Table 1 Feedstuffs , June 2008). The established tolerance on potato of 0.02 ppm is being converted into a tolerance on the tuberous and corm vegetable subgroup 1C at the same level . There is an established tolerance on turnip greens. T urnip greens are grown for human consumption and are not likely to be used as a livestock feed. Since no residue data have been submitted for cowpea forage and hay , th e Ranman 400SC label (EPA Reg. No. 71512 - 3) should be amended to prohibit application to cowpea grown for livestock feed. The statement “Do not appl y to cowpea used for livestock feed” should be added to the label. With the restriction against use on cowpea used for livestock feed , there are no poultry or swine feed items associated with the registered or proposed uses.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 18 of 45 **Table 7**  **. Calculation of Dietary Burdens of C**  **yazofam id**  **Residues to Livestock** . Feedstuff Ty pe 1 % Dry Matter2 % Diet2 Established Tolerance or HAFT (ppm) 3 Dietary Contribution (ppm) 4 **Beef Cattle** Untreated R -- 15 0 0 Potato, culls CC 20 30 0.02 0.03 Potato, processed waste CC 15 30 0.02 0.04 Untreated CC -- 20 0 0 Untreated PC -- 5 0 0

TO TAL BURDEN -- -- 100 -- **0.07 Dairy Cattle**  Untreated R -- 45 0 0 Carrots, culls 5 CC 12 10 0.09 0.075 Untreated CC -- 3 5 0 0 Untreated PC -- 10 0 0

TO TAL BURDEN -- -- 100 -- **0.0 75**  1 R: Roughage; CC: Carbohydrate concentrate; PC: Protein concentrate. 2 Table 1 Feedstuffs ( July 2008 ). 3 The established tolerance is used for the registered use (carrot) ; the highest average field trial (HAFT) value is used for the proposed use (potato) . 4 Contribution for beef and dairy cattle = tolerance ÷ % DM x % diet . 5 Potato culls and potato processed waste can also be fed to dairy cattle; however, both carrot and potato feed items are not expected to be fed. No ruminant f

eeding study

has been submitted. Based on the goat metabolism study (MRID 45409018; PP#1F06305), residues in milk and ruminant tissues reflecting a dosing level of 10 ppm are reported in Table 8 below. In the metabolism study , two lactating goats per tre atment group were orall y dosed with the radiolabel led cyazofamid test substances for five consecutive day s at a nominal rate of 10 ppm based on the food consumption during the acclimation period. The dosing level of 10 ppm is equivalent to 143 x and 1 33 x the maximum dietary burden of cyazofamid in beef and dairy cattle, respectivel y **Table 8.**  **Total Radioactive Residues, Expressed as Cyazofam** **id Equivalents, in Goat Matrices from** **a Me**  **tabolism Study a**  **fter Dosing with Radiolabelled Cyazofam id at 10 ppm.**  Goat Matrix [Benzene 14 C]Cyazofamid (ppm) [Imidazole 14 C]Cyazofamid (ppm) Milk 0.004 - 0.006 0.002 - 0.010 Liver 0.126 0.125 Kidney 0.07 0.106 Loin muscle 0.004 0.006 Rear leg muscle nondetectable (<0.01) nondetectable (<0.01) Omental fat 0.006 0.01 Perirenal fat 0.01 0.01Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 19 of 45 **Table 9.**  **Summary of Ruminant Metabolism** **S tudies with**  **Cyazofam id**  **.** Commodity Feeding Level (ppm) Max. Residue in

Tissue (ppm) Tissue - to - Feed

Ratio Dietary Burden

(ppm) Expected

Residue (ppm) Milk 10 0.01 0.001 0.0 75 0.0000 75 Muscle (cattle) 0.01 0.001 0.07 0.00007 Fat (cattle) 0.01 0.001 0.07 0.00007 Liver (cattle) 0.126 0.0126 0.07 0.00088 Kidney (cattle) 0.106 0.0106 0.07 0.00088 Conclusions . The results of the goat metabolism study indicate that tolerances for residues of cyazofamid in ruminant commodities are not required for the purpose of this petition since there is no reasonable expectation that finite residues will occur in ruminant commodities [40 CFR §180.6(a)(3)]. Toleranc es for residues of cyazofamid in poultry and swine commodities are not required provided that application to cowpea used for livestock feed is prohibited on the label. With that label prohibition, there are no poultry or swine feed items associated with the proposed or registered uses , and the proposed and registered uses fall under 40 CFR §180.6(a)(3) for poultry commodities . **Crop Field Trials (860.1500)**  48629401.der (includes MRID 48629405) (Lettuce, Head and Leaf) 48629402.der (Basil) 48629403.der (Snap B ean) 48629404.der (Lima B ean) **Table 10**  **. Summary of Residues from Field Trials with Cyazofam** **id 1,2**  Crop Matrix Analyte Applic. Rate (lb ai/acre) PHI

(days) n Residues (ppm)

Min. Max. LAFT HAFT Median Mean SD **BAS IL**  **Proposed Use = 0.7**  **lb ai/acre total application rate, 0**  **- day PHI**  Basil, fresh (leaves and stems) 3 Cyazofamid

+ CCIM 0.693 -

0.721 0 6 2.4 15 2.6 14 8.5 8.4 5.1 Basil, dried (leaves and stems) 3 Cyazofamid

+ CCIM 0.693 -

0.721 0 4 11 46 11 43 30 28 13 **BEAN, LIMA Proposed Use =**  **0.43 lb ai/acre total application rate,**  **0 -**  **day PHI** Bean, lima ( succulent seeds) Cyazofamid

+ CCIM 0.427 -

0.523 0 - 1 6 <0.02 <0.057 <0.02 <0.050 0.020 0.025 0.012 **BEAN, SNAP Proposed Use =**  **0.43 lb ai/acre total application rate,**  **0 -**  **day PHI** Bean, snap (pods with seeds) Cyazofamid

+ CCIM 0.426 -

0.507 0 8 <0.022 <0.23 <0.029 <0.21 0.12 0.12 0.072 **LETTUCE, HEAD Proposed Use =**  **0.43 lb ai/acre total application rate,**  **0 -**  **day PHI**Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 20 of 45 Lettuce, head (head with wrapper leaves) Cyazofamid

+ CCIM 0.419 -

0.506 0 11 <0.06 2.0 <0.080 1.8 0.65 0.83 0.61 **LETTUCE, LEAF Proposed Use =**  **0.43 lb ai/acre total application rate,**  **0 -**  **day PHI** Lettuce, leaf (leaves) Cyazofamid

+ CCIM 0.427 -

0.587 0 11 <0.49 4.6 <0.54 4.5 1.8 2.1 1.3 1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. 2 LAFT = Lowest Average Field Trial ; HAFT = Highest Average Field Trial ; SD = Standard Deviation. For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ. 3 Data for fresh basil include field trials and greenhouse trials. Data for dried basil reflect field trials. The following data were previously reviewed and are included here for use in crop group establishment: 47528 401 .der (Pepper) 45409033.der (Potato) 47870704.der (Spinach) 45409031 .de1 (includes MRIDs 45638507 and 45638508 ) (Tomato) **Table 11. Summary of Residues from Field Trials on Pepper,**  **Spinach , and Tomato**  **with Cyazofam id)**  **1, 2** Crop Matrix Analyte Applic. Rate (lb ai/acre) PHI

(days) n Residues (ppm)

Min. Max. LAFT HAFT Median Mean SD **PEPPE R Proposed Use = 0.43 lb ai/acre total application rate, 0**  **- day PHI**  Pepper , Bell Cyazofamid

+ CCIM 0.418 -

0.429 0 6 <0.047 0.297 <0.048 <0.236 0.075 0.101 0.069 Pepper, Nonbell Cyazofamid

+ CCIM 0.419 -

0.426 0 3 <0.221 0.331 <0.258 0.321 0.259 0.279 0.036 **POTATO Proposed Use = 0.71 lb ai/A total application rate, 7 -**  **day PHI** Potato Cyazofamid

+ CCIM 0.698 -

0.743 7 18 <0.02 <0.02 <0.02 <0.02 <0.02 <0.02 <0.02 **SPINACH Proposed Use = 0.43 lb ai/acre total application rate, 0 -**  **day PHI** Spinach Cyazofamid

+ CCIM 0.347 -

0.366 0 10 1.5 6.6 1.6 6.5 3.1 3.3 1.5 **TOMATO Proposed Use = 0.43 lb ai/acre total application rate, 0 -**  **day PHI** Tomato Cyazofamid

+ CCIM 0.413 -

0.434 0 16 <0.02 <0.17 <0.02 <0.16 0.055 0.063 0.035 1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. 2 LAFT = Lowest Average Field Trial; HAFT = Highest Average Field Trial; SD = Standard Deviation. For computation of the LAFT, HAFT, median, mean, and standard deviation, values < LOQ are assumed to be at the LOQ of 0.01 ppm for each analyte . Basil The Interregional Research Project Number 4 (IR - 4) has submitted field trial data for cyazofamid on basil . Four field trials were conducted in the United States during the 2009 - 2010 growing seasons in the North American Free Trade Agreement (NAFTA) Growing Zones 2 (MD and NC; 2 trials) and 10 (CA and AZ; 2 trials). In addition, two greenhouse trials were conducted in Zones 3 (FL) and 10 (CA).Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 21 of 45 Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated plot received nine foliar broadcast or directed applications of a 3.33 lb ai/gal suspension concentrate ( SC ) formulatio n of cyazofamid ( Ranman® 400SC ) at 0.074 - 0.083 lb ai/A/application, for a total seasonal r ate of 0.693 - 0.721 lb ai/A. Applications were made at 6 - to 8 - day retreatment intervals (RTI s) using ground equipment in spray volumes of 21.07 - 46.28 gal/A. An organosilicone surfactant ( OSS ) , Silwet L - 77, was added to the spray mixture for each of the a pplications. The use rates of adjuvant:formulated product were mostly 2:3 or 3:4, v/v. Samples of fresh basil leaves and stems were harvested from all trials at a 0 - day preharvest interval ( PHI ) ; additional samples were collected at PHI s of 4, 7, 1 0 , and 14 day s from one trial ( MD04 ) to assess residue decline. Additional leaves and stems were collected from four trials and dried for 1 - 3 day s under ambient conditions or in an oven or forced air dry er to produce dried basil. Samples were anal yz ed for resi dues of cyazofamid and its metabolite CCIM using an LC /MS/MS method adapted from a P yx ant Labs, Inc. anal yt ical method. The limits of quantitation ( LO Q s; determined as the lowest level of method validation, LLMV) in fresh and dried basil were 0.01 and 0.1 ppm , respectivel y, for each anal yt e . The method was adequate for data collection based on acceptable method validation and concurrent recovery data. The fortification levels used in concurrent method recovery were adequate to bracket expected residue le vels. C oncurrent recoveries and r esidues in the treated samples were not corrected for residues in controls. The anal yt ical method does not specify conversion of metabolite residues to parent equivalents; therefore, quantifiable residues of CCIM were converted to parent equivalents by

the study reviewer using a molecular weight conversion factor of 1.49 (MW of cyazofamid 324.79 ÷ MW of CCIM 217.65). Samples were stored frozen ( - 20 °C) from collection to analy sis for 8 - 284 day s (0.3 - 9.3 months) for fresh basil and 155 - 299 day s (5.1 - 9.8 months) for dried basil. Samples were anal yz ed within 0 - 1 day s of extraction . To support the sample storage intervals, a concurrent storage stability study was conducted with the field trial study . The data demonstrate that residues of cyazofamid and CCIM were reasonably stable in/on dried basil stored frozen for up to 297 day s and residues of cyazofamid were stable in/on fresh basil stored frozen for up to 284 day s, but residues of CCIM in/on fresh basil declined by 46% after 284 day s of freezer storage. No 0 - day data were provided. Samples of fresh basil were stored up to 284 day s prior to anal ys is; therefore, the CCIM residue values for fresh basil were adjusted for residue decline on storage. No corrections for potential decline during storage are needed for residues of cyazofamid and CCIM in/on dried basil or for residues of cyazofamid in/on fresh basil from the submitted field trials; however, storage stability

studies should alway s include a 0 - day sampling interval to establish the residue levels present at the time samples are placed into storage [see O CSPP 860.1380(d)(6 )(i)]. Following nine foliar broadcast or directed applications of the 3.33 lb ai/gal SC formulation of cyazofamid at 0.693 - 0.721 lb ai/A, residues (and per trial averages) of cyazofamid, CCIM, and combined residues, respectively , in/on fresh basil leaves and stems (from greenhouse and field trials) harvested at a 0 - day PHIwere 2.3 - 15 (2.5 - 14), 0.037 - 0.28 (0.040 - 0.28), and 2.4 - 15 (2.6 - 14) ppm; corresponding residues (and per trial averages) in/on dried basil leaves and stems (field trials only) were 9.3 - 4 3 (9.6 - 40), 1.5 - 16 (1.6 - 16), and 11 - 46 (11 - 43) ppm.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 22 of 45 Residues were generally

higher in samples from the greenhouse trials than in samples from the field trials. In the field trials, residues (and per trial averages) of cy azofamid, CCIM, and combined res idues, respectively , in/on fresh basil leaves and stems harvested at a 0 - day PHI were 2.3 - 10 (2.5 - 9.4), 0.037 - 0.28 (0.040 - 0.28), and 2.4 - 10 (2.6 - 9.6) ppm; corresponding residues (and per trial averages) in/on fresh basil leaves and stems in the greenhouse trials were 12 - 15 (14 - 14), 0.092 - 0.15 (0.096 - 0.13), and 12 - 15 (14 - 14) ppm. Dried basil leaves and stems were not collected in the greenhouse trials. In the residue decline trial with fresh basil leaves and stems, average residues of cyazofamid and CCIM d eclined from 2.6 ppm at the 0 - day PHI to <0.34 ppm at the 14 - day PHI . Bean, lima IR - 4 has submitted field trial data for cyazofamid on lima beans . Eight field trials were conducted in the United States during the 2009 growing season in the NAFTA Growing Zones 2 (MD and NC; 4 trials), 5 (WI ; 1 trial), 10 (CA; 2 trials), and 11 (ID; 1 trial). Two trial pairs (MD15/MD24 and NC30/NC31) were each conducted at the same location. Careful examination of the field trial records in accordance with ChemSAC guidan ce (Field Trial Differentiation, 2012 Protocol) indicates that the only differences between each pair of trials were: use of different varieties of lima beans (all trials), use of different tank mixes for all applications (all trials); and a 6 - day

off - set in application dates (NC30/NC31 trials only). HED has concluded that the differences between the trials are insufficient to classify them as separate trials; therefore, each pair of trials constitutes a single trial with replicate samples for purposes of OCSPP 860.1500 data requirements. The adjustment in trial numbers results in a total of six field trials, with two trials conducted in NAFTA Zone 2. Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated plo t received at least six foliar broadcast or directed applications of a 3.33 lb ai/gal SC formulatio n of cyazofamid ( Ranman® 400SC ) at 0.069 - 0.076 lb ai/A/application, for a total seasonal rate of 0.427 - 0.523 lb ai/A. One additional application was require d at three trial sites to allow the crop to mature (CA134) or due to unexpected rainfall occurring after the sixth application, thereb y potentially impacting the residues if the samples were harvested following the rainfall (NC30 and NC31). Applications w ere made at 6 - to 8 - day RTIs using ground equipment in spray

volumes of 32.51 - 46.08 gal/A. An OSS , Silwet L - 77, was added to the spray mixture for each of the applications. The use rate of adjuvant:formulated product was 3:4, v/v. Samples of lima beans were harvested from all trials at a 0 - day PHI , except for Trial NC31, where samples were harvested at a 1 - day PHI to allow plants to dry following rainfall that occurred 3 hours after the last application . Samples were anal yz ed for residues of cyazofamid and its metabolite CCIM using an L C/MS/MS method adapted from a P yx ant Labs, Inc. anal yt ical method. The LOQ , determined as the LLMV , was 0.01 ppm for each anal yt e . The method was adequate for data collection based on acceptable method validation and co ncurrent recovery data. The fortification levels used in method validation and concurrent method recovery were adequate to bracket expected residue levels. C oncurrent recoveries and r esidues in the treated samples were not corrected for residues in controls. The anal yt ical method does not specify conversion of metabolite residues toCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 23 of 45 parent equivalents. Residues of CCIM were not converted to parent equivalents in this study because residues of the metabolite were below the LOQ in/on all samples. Samples were stored frozen ( - 20 °C) from collection to analy sis for 63 - 147 day s (2.1 - 4.8 months). Samples were anal yz ed within 0 - 1 day s of extraction. Storage stability data generated concurrently

with the field trial study

demonstrate that residues of c yazofamid and CCIM were stable in/on samples of lima beans stored frozen for up to 140 days; no 0 - day data were provided. These data are acceptable to support the storage conditions and durations of samples from the submitted field trials; however, storag e stability studies should alway s include a 0 - day sampling interval to establish the residue levels present at the time samples are placed into storage [see O CSPP 860.1380(d)(6)(i)]. Following six to seven foliar broadcast or directed applications of the 3.33 lb ai/gal SC formulation of cyazofamid at 0.427 - 0.523 lb ai/A, residues (and per trial averages) of cyazofamid, CCIM, and combined residues, respectively , in/on lima bean succulent seeds harvested at a 0 - to 1 - day PHIwere <0.01 - 0.047 (<0.01 - 0.040), < 0.01 (<0.01), and <0.02 - <0.057 (<0.02 - <0.050) ppm. Cyazofamid residues were only detected in the ID20 trial. No residue decline data were submitted. Bean, snap IR - 4 has submitted field trial data for cyazofamid on snap beans . Eight field trials were c onducted in the United States during the 2007 growing season in the NAFTA Growing Zones 2 (NJ, MD, and GA; 3 trials), 5 (MI and WI; 2 trials), 10 (CA; 2 trials), and 11 (WA; 1 trial). Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated plot received at least six foliar broadcast or directed applications of a 3.33 lb ai/gal SC formulatio n of cyazofamid ( Ranman® 400SC ) at 0.069 - 0.079 lb ai/A/application, for a total seasonal rate of 0.426 - 0.507 lb ai/A. On e additional application was required at the CA10 trial to allow the crop to mature. Applications were made at 6 - to 9 - day RTIs using ground equipment in spray

volumes of 31.90 - 60.08 gal/A. An OSS , Silwet L - 77, was added to the spray mixture for each of the applications. The use rate of adjuvant:formulated product was 3:4, v/v. Samples of snap bean pods with seed and snap bean plants with pods were harvested from all trials at a 0 - day

PHI; additional samples of snap bean pods with seed were collected at PHIs of 2 , 7, and 12 day s from one trial ( GA*11 ) to assess residue decline. Samples were anal yz ed for residues of cyazofamid and its metabolite CCIM using an LC/MS/MS method adapted from a P yx ant Labs, Inc. anal yt ical method. The LOQ , determined as the LLMV , was 0.01 ppm for each anal yt e . The method was adequate for data collection based on acceptable method validation and concurrent recovery data. The fortification levels used in method validation and concurrent method recovery were adequate to bracke t expected residue levels. C oncurrent recoveries and r esidues in the treated samples were not corrected for residues in controls. The anal yt ical method does not specify conversion of metabolite residues to parent equivalents; therefore, quantifiable residues of CCIM were converted to parent equivalents by

the study reviewer using a molecular weight conversion factor of 1.49 (MW of cyazofamid 324.79 ÷ MW of CCIM 217.65).Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 24 of 45 Samples were stored frozen ( - 20 °C) from collection to analy sis for 861 - 946 day s (28.3 - 31.1 months) for pods with seeds and 847 - 944 day s (27.9 - 31.0 months) for plants with pods. Samples were anal yz ed within 0 - 1 day s of extraction. Storage stability data generated concurrentl y with the field trial study

demonstrate that residues of cyazofamid and CCIM were stable in/on samples of snap bean stored frozen for up to 887 - 889 day s; no 0 - day data were provided. These dat a are acceptable to support the storage conditions and durations of samples from the submitted field trials; however, storage stability studies should alway s include a 0 - day sampling interval to establish the residue levels present at the time samples are placed into storage [see O CSPP 860.1380(d)(6)(i)]. Following six to seven foliar broadcast or directed applications of the 3.33 lb ai/gal SC formulation of cyazofamid at 0.426 - 0.507 lb ai/A, residues (and per trial averages) of cyazofamid, CCIM, and combi ned residues, respectively , in/on snap bean pods with seeds harvested at a 0 - day

PHIwere 0.012 - 0.22 (0.019 - 0.20), <0.01 (<0.01), and <0.022 - <0.23 (<0.029 - <0.21) ppm; corresponding residues (and per trial averages) in/on snap bean plants with pods were 1.0 - 3.6 (1.4 - 3.3), 0.017 - 0.099 (0.029 - 0.088), and 1.1 - 3.6 (1.4 - 3.3) ppm. In the residue decline trial with snap bean pods with seeds, average residues of cyazofamid declined from 0.20 ppm at the 0 - day PHI to 0.13 ppm at the 12 - day PHI; residues of CCIM wer e <0.01 ppm in/on all samples. Le ttuce, head and leaf IR - 4 has submitted field trial data for cyazofamid on head and leaf lettuce . Twenty - six field trials were conducted in the United States and Canada during the 2008 - 2009 growing seasons in the NAFTA Growing Zones . Thirteen head lettuce trials were conducted in Zones 1 (NY; 1 trial), 3 (FL; 1 trial), 5 (ON; 2 trials), 5A (QC; 1 trial), 5B (QC; 1 trial), 10 (NM and CA; 6 trials), and 12 (BC; 1 trial), and thirteen leaf lettuce trials were conducted in Z ones 2 (MD; 1 trial), 3 (FL; 1 trial), 5 (ON; 2 trials), 5A (QC; 1 trial), 5B (QC; 1 trial), 10 (NM and CA; 6 trials), and 12 (BC; 1 trial). Four trial pairs [08 - CA*04/08 - CA*05 (Salinas, CA, head lettuce); 08 - CA03/08 - CA19 (Holtville, CA; head lettuce); 08 - NM14/08 - NM12 (Las Cruces, NM; leaf lettuce); and 08 - CA*22/08 - CA*21 (Salinas, CA; leaf lettuce)] were each conducted at the same location. Careful examination of the field trial records in accordance with ChemSAC guidance (Field Trial Differentiation, 2 012 Protocol) indicates that the only differences between each pair of trials were: use of different varieties of lettuce (all trials), use of different tank mixes for all applications (all trials); an 8 - day off - set in application dates (CA*22/CA*21 trial s only); and a difference in soil ty

pe (loam vs. sandy

loam; CA*22/CA*21 trials only). HED has concluded that the differences between the trials are insufficient to classify them as separate trials; therefore, each pair of trials constitutes a single tria l with replicate samples for purposes of OCSPP 860.1500 data requirements. The adjustment in trial numbers results in a total of 22 field trials (11 head lettuce trials and 11 leaf lettuce trials), with four trials each for head lettuce and leaf lettuce c onducted in NAFTA Zone 10.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 25 of 45 Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated plot received at least six applications of a 3.33 lb ai/gal SC formulatio n of cyazofamid ( Ranman® 400SC ) at 0.065 - 0.079 lb ai/A/application (0.073 - 0.088 kg ai/ha/application), for a total seasonal rate of 0.419 - 0.587 lb ai/A (0.471 - 0.658 kg ai/ha). The first application was made to soil as a post - plant application after seeding or a post - transplant application. These applicatio ns were made on the day of or 1 day

following planting or transplanting. Subsequent applications were made as foliar broadcast or directed applications with RTIs of 6 - 78 day s between applications 1 and 2 and 5 - 15 day s (mostly 6 - 8 day s) between application s 2 through 8; applications were timed so that mature lettuce could be collected immediately following the final application (after the test substance had dried). One to two additional applications were required in five trials (CA*05, CA*04, NM11, NM14, and ON Trial 690) to allow the crop to mature. All applications were made using ground equipment in spray volumes of 30 - 49 gal/A (283 - 460 L/ha). A non - ionic surfactant (NIS; Sylg ard 309) or OSS ( Silwet L - 77) was added to the spray mixture for each of the applications except for the first post - plant applications (all trials) and some post - transplant applications . The use rate of adjuvant:formulated product was 3:4, v/v. Samples of head lettuce with wrapper le aves and leaf lettuce were harvested from all trials at a 0 - day PHI ; additional samples were collected at PHIs of 4, 7, 15, and 21 day s from one leaf lettuce trial (CA*22) to assess residue decline. In addition, samples of head lettuce without wrapper leaves were also collected at the three 2009 Canadian head lettuce trials. Samples were anal yz ed for residues of cyazofamid and metabolite CCIM using an LC/MS/MS method adapted from a Pyxant Labs, Inc. anal yt ical method. The LOQ , determined as the LLMV , was 0.01 ppm for each anal yt e . The method was adequate for data collection based on acceptable method validation and concurrent recovery data. The fortification levels used in concurrent method recovery were adequate to bracket expected residue levels. C oncurrent recoveries and r esidues in the treated samples were not corrected for residues in controls. Since the anal yt ical method does not specify conversion of metabolite residues to parent equivalents, quantifiable residues of CCIM were converted to p arent equivalents by the study reviewer using a molecular weight (MW) conversion factor of 1.49 (MW of cyazofamid of 324.79 ÷ MW of CCIM of 217.65). Samples were stored frozen ( - 20 to - 8.9 °C) from collection to anal ys is for 208 - 634 day s (6.8 - 20.8 months) for head lettuce and 251 - 624 day s (8.3 - 20.5 months) for leaf lettuce. Samples were anal yz ed within 0 - 1 day s of extraction. Storage stability data generated concurrentl y with the field trial study

demonstrate that residues of cyazofamid and CCIM were sta ble in/on samples of leaf lettuce stored frozen for up to 634 day s; no 0 - day data were provided. These data are acceptable to support the storage conditions and durations of samples from the submitted field trials . Any

storage stability

studies which may be submitted in the future should alway s include a 0 - day sampling interval to establish the residue levels present at the time samples are placed into storage [see O CSPP 860.1380(d)(6)(i)]. Following one soil banded application made post - planting or post - transplant and five to seven foliar broadcast or directed applications (six to eight total applications) of the 3.33 lb ai/gal SC formulation of cyazofamid at 0.419 - 0.587 lb ai/A (0.471 - 0.658 kg ai/ha), residues (and per trial averages) of cyazofamid, CCIM, and combined residues, respectivel y, in/on head lettuce with wrapper leaves harvested at a 0 - day PHI were 0.05 - 2.0 (0.070 - 1.8), <0.01 - 0.044 (<0.01 - 0.038),Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 26 of 45 and <0.06 - 2.0 (<0.080 - 1.8) ppm; corresponding residues (and per trial averages) in/on head lettuce without wrapper leaves were <0.01 - 0.57 (<0.01 - 0.55), <0.01 - 0.019 (<0.01 - 0.018), and <0.02 - 0.59 (<0.02 - 0.58) ppm. Residues (and per trial averages) of cy azofamid, CCIM, and combined residues, respectively , in/on leaf lettuce harvested at a 0 - day PHIwere 0.48 - 4.5 (0.53 - 4.5), <0.01 - 0.074 (<0.013 - 0.064), and <0.49 - 4.6 (<0.54 - 4.5) ppm. In the residue decline trial with leaf lettuce, average combined residues of cyazofamid and CCIM declined from 2.8 ppm at the 0 - day PHI to <0.12 ppm at the 21 - day PHI. Crop Groups Fruiting Vegetable Group 8 - 10 A tolerance of 0.40 ppm is established for the fruiting vegetable group 8. The representative commodities for Crop Group 8 - 10 are tomato, standard size, and one cultivar of small tomato; bell pepper and one cultivar of small nonbell pepper. Tomato Residue data have previously been reviewed for tomatoes (DP# D285680, A. Acierto, 2/20/04 and 10/1/04; 45409031.der). The residue data included data on the standard size tomato and on Roma tomato, which is a small tomato. Sixteen field trials were conducted on tomato with a PHI of 0 day s. Six broadcast foliar applications were made at the rate of approximately 0.071 lb ai/A/application for a total of 0.413 - 0.434 lb ai/A/season with retreatment intervals of mostly 6 - 8 day s and a 0 - day

PHI. An OSS was used in several field trials on tomato. The use rate of adjuvant:formulated product was 3:4, v/v. Pepper Residue data have previously been reviewed for bell and nonbell pepper (DP# D357042, A. Acierto, 3/18/09; 47528401 .der). Six field trials were conducted on bell pepper and three fie ld trials were conducted on nonbell pepper. Six broadcast foliar applications were made at the rate of 0.067 - 0 .075 lb ai/A/application for a total of 0.418 - 0.429 lb ai/A/season with retre atment intervals of 6 - 8 day s and a 0 - day PHI. An OSS was used in all field trials on pepper. The use rate of adjuvant:formulated product was 3:4, v/v. Conclusion re. f

ruiting vegetable group 8 - 10. The currently registered label for fruiting vegetables (letter dated 8/13/10) and the proposed label for the fruiting vegetable group 8 - 10 are the same regarding the methods of application, number of applications, application rates, interval between foliar applications, and PHI . The residue data supporting the established fruiting vegetable group 8 tolerance support the fruiting vegetable group 8 - 10 tolerance ; however, the OECD calculator using average field trial residues gives tolerance levels of 0.2 ppm for tomato, 0.4 ppm for b ell pepper, and 0.9 ppm for nonbell pepper; therefore, the tolerance for the fruiting vegetable crop group should be 0.9 ppmCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 27 of 45 instead of the proposed 0.40 ppm. Leafy greens subgroup 4A The representative commodities for the leafy greens subgroup 4A are head lettuce, leaf lettuce, and spinach. The head and leaf lettuce field trials adequatel y reflect the proposed use . The spinach trials reflect five applications instead of the proposed six. Head Lettuce : Six to seven applications were made to head lettuce, at 0.07 - 0.08 lb ai/A/application. The first application was a post - plant or post - transplant directed band applied 0 - 1 day after seeding or transplanting. Five or six foliar applications were made, mostly six to eight day s apart. The PHI was 0 day s. The total applied was 0.419 - 0.506 lb ai/A/crop. An NIS or OSS surfactant was used with all foliar applications. Leaf Lettuce : Six to eight applications were made to head lettuce, at 0 .07 - 0.08 lb ai/A/application. The first application was a post - plant or post - transplant directed band applied 0 - 1 day after seeding or transplanting. Five to seven foliar applications were made, six to eight day s apart. The PHI was 0 day s. The total a pplied was 0.427 - 0.587 lb ai/A/crop. An NIS or OSS was used with all foliar applications. Spinach : Field trials on spinach were previously reviewed (MRID 47870704; D371162, A. Acierto, 2/24/10). At each test location , five foliar applications of Ranman 400SC were made at the target rate of 0.072 lb ai/A/application for a total of 0.347 - 0.366 lb ai/A/season , with 7 (± 1 ) day intervals and a 0 - day PHI . An OSS, Silwet L - 77 , was used in all field trials. Foliar broadcast applications were made at all field sites except TX*12, where foliar directed applications were made. F ive applications totaling 0.347 - 0.366 lb ai/A were made in the field trials, whereas the proposed use would allow six applications totaling 0.43 lb ai/A. The current Ranman 400SC label (letter dated 8/13/10) restricts the number of applications on spinach to five. The OECD calculator using average field trial residues gives a value of 10 ppm for spinach. Conclusion re. leafy green s subgroup 4A . The highest residue value for spinach was 6.6 ppm, reflecting five foliar applications. A 10 ppm tolerance can be reasonably expected to be adequate to cover an additional sixth application. Vegetable, tuberous and corm, subgroup 1C A tolerance is established on potato at 0.02 ppm. The on ly representative commodity for the tuberous and corm vegetable subgroup 1C is potato. Field trial data on potato were previousl y reviewed (D285680, A. Acierto, 2/20/04; 45409033.der). Residue data reflected seven to ten broadcast foliar applications for total application rate s of 0.698 - 0.743 lb ai/A with retreatment intervals of 5 - 8 day s and a 7 - day PHI . An OSS, Silwet L - 77 , was used in all field trials. The LOQ of the HPL C/UV method (MRIDCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 28 of 45 45409020) was 0.01 ppm for each analy te. Combined residues of cyazofamid and CCIM were all <0.02 ppm. The residue data on potato can be used to support a subgroup 1C tolerance. The current Ranman 400SC label (letter dated 8/13/10) for potato is consistent with the proposed use directions for potato with respe ct to methods of application, number of applications, application rates , interval between foliar applications , and PHI . Conclusion re. tuberous and corm vegetable subgroup 1C. The previously submitted residue data on potato supports the proposed use and the proposed 0.02 ppm tolerance on the tuberous and corm vegetable subgroup 1C. **Processed Food and Feed (860.1520)**  Amelia Acierto, 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishment of Permanent Tolerances for Use on Cucurbits, Potatoes, Tomatoes, and Imported Wine Grapes. Summary of Analytical Chemistry and Residue Data ; 45409033.de2 (potato) and 45409031.de2 (tomato) Amelia Acierto, 3/18/09, DP# D357042, Cyazofamid. Amend Section 3 to Add Uses on Fruiting Vegetables, Okra, Grape (East of the Rocky Mountains), and Greenhouse Vegetable Transplants. Summary of Analytical Chemistry and Residue Data. No additional processing studies have been submitted. Processing studies have previousl y been reviewed on potato and tomato. The anal yt ical method used in the potato and tomato processing studies was the HPL C/UV enforcement method (MRID 45409020). Potato: No detectable residues of cyazofamid or CCIM were found in the potato tubers used for processing or the processed commodities ( chips, flakes, and wet peel). The reviewer requested that a study

be conducted at 5x because the RAC samples that were used for processing bore nondetectable (<0.01 ppm) residues after treatments at an exaggerated rate of ~1.9x, which is less than the max imum theoretical concentration factor of 5.0x for potatoes. The petitioner submitted the following response in MRID 46537730 :

“ The maximum label application for c yazofamid to potatoes is 0.071 lb ai /A applied 10 times at 7 - day

intervals. For the process ing study , applications 1 through 6 were made at 0.070 - 0.073 lb ai/A and at 7 - day intervals. Applications 7 through 10 were made at 5 - day intervals. T he final application was at a l0 x rate (0.713 lb ai/A). Cyazofamid has been shown to have a half - life of about 1 day

on crops such as cucumber, cantaloupe, summer squash and tomato. With this short half - life there is essentially

no carryover from one application to the next even with the shorter 5 - day interva l. Consequently

the final application is the only application that will potentially result in residues on the RAC and it was applied at 10 X the label rate. In addition, the label PHIis 7 day s but in the potatoes grown for processing the samples were co llected at a PHI of 3 days. The potatoes were delivered to the processor within a couple of hours of sampling since the processor was onl y 20 miles from the field site. The samples were stored for 19 days at 7 °C ± 3 °C prior to processing. The use of exa ggerated rates of application is to assure that residues are present toCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 29 of 45 determine the concentration or lack thereof after processing. Two representative samples were taken for anal ys is in the field. One sample had 0.02 ppm cyazofamid and 0.01 ppm CCIM. Th e other sample had <0.01 ppm for both compounds. Therefore, the desired residues were present in the field. Samples taken 19 day s later at the time of processing had residues <0.01 ppm for both compounds. Storage for periods longer than 19 day s is ty pic al for potatoes being processed into chips or granules. The processing loss is clearly in the storage phase of the processing, not in the production of the potatoes. Considering that the last application rate used was 10X the proposed rate and the PHI wa s decreased to 3 day s, it is unlikely

that repeating the study

with multiple applications at 5X at 7 - day intervals would achieve residues an y higher than those found in this study. C onsequently , it is I SK Biosciences Corporation’s opinion that this study is scientifically valid and that a replacement is not needed.” The potato processing study is adequate to conclude that the combined residues in the processed commodities are not likely to exceed the 0.02 ppm tolerance level on the potato tuber. Tomato : The tomato processing data indicated that residues of cyazofamid do not concentrate in tomato paste and puree (processing factors of < 0.3x) and residues of CCIM do not concentrate significantl y in puree but concentrated by a factor of 4x in tomato paste . Although concentration of CCIM in tomato paste was observed , combined residues of cyazofamid and CCIM are not likely to concentrate in tomato processed commodities to exceed the tolerance on the RAC . Conclusions

. No additional processing studies have been submitted and none are required. The previously

submitted tomato and potato processing studies are adequate to show that residues in tomato and potato processed commodities will not concentrate above the toleranc e levels for the raw agricultural commodit ies; therefore, separate tolerances on the processed commodities of tomato and potato are not required. **Rotational Crops (Field; 860.1900)**  Breann Hanson, 8/3/10, DP# D376500, Cyazofamid. Human Health Risk Assess ment for Proposed Section 18 Use on Basil. Since the results of the confined rotational crop study showed that cyazofamid and structurally related metabolites are each expected to be present at a level less than 0.01 ppm at a plantback interval of 30 day s , no field rotational crop studies are required. **Tolerance Derivation**  The Organization for Economic Cooperation and Development (OECD) tolerance calculation procedures were used to determine tolerance estimates for the raw agricultural commodities. Av erage values of replicate samples for each field trial constituted the database. For consideration of crop group or subgroup tolerances, the representative commodities were evaluated individually

to determine a tolerance estimate for each representative c rop; the highest tolerance estimate was used for the crop group or subgroup tolerance.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 30 of 45 All trials were conducted within ±25% of the good agricultural practices (GAP) application rate and PHI. Therefore, proportionality was not considered for an y of the trials. An organosilicone surfactant ( OSS) was used in all field trials on basil, snap beans, lima beans, pepper, potato, and spinach and on several field trials on tomato. A nonionic surfactant (NIS) or OSS was used in all field trials on head lettuce an d leaf lettuce. The adjuvant: Ranman 400SC use rate was 3:4 (v/v) for all crops except basil; for basil, the adjuvant use rate was mostly 2:3 or 3:4 (v/v). The data collection method s w ere an HPL C/UV method or an L C/MS/MS method which is a modified version of the HPL C/UV method. Both methods determine parent and CCIM with an LOQ of 0.01 for each analy te in basil, snap bean, lima bean, lettuce, pepper, potato, spinach, and tomato RACs, and an L OQ of 0.1 ppm for each analy te in dried basil. An OECD t olerance calculation was not conducted for potato since all residues in the potato field trial were less than the LOQ. Some censored data (combined residues <0.02 ppm) were included in the data set for lima bean. The tomato data set contained one censore d residue level. T he residue values used as inputs and the recommended tolerances are summarized below .Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 31 of 45 Basil , f resh ( MRID 48629402 ) A tolerance of 30 ppm is appropriate for fresh basil based on six trials (four field trials and two greenhouse trials) at a total seasonal application rate of 0.693 - 0.721 lb ai/A with a 0 - day PHI . 0.693 - 0.721 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  2.6 1 2.9 1 7.4 1 9.6 1 14 2 **Cyazofamid**

**Basil -**  **fresh USA**  **0.693 -**  **0.721 lb ai/A;**  **0 -**  **day PHI Total number of data (n)**  6 **Percentage of censored data** 0% **Number of non -**  **censored data** 6 **Lowest residue** 2.600 **Highest residue** 14.000 **Median residue** 8.500 **Mean** 8.417 **Standard deviation (SD)** 5.080 **Correction factor for censoring (CF)**  1.000 **Proposed MRL estimate**

**- Highest residue**  14.000

**- Mean + 4 SD**  28.738

**- CF x 3 Mean**  25.250 **Unrounded MRL** 28.738 **Rounded MRL 30**  High uncertainty of MRL estimate. [Small dataset]Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 32 of 45 Basil , dried ( MRID 48629402 ) A tolerance of 90 ppm is appropriate for dried basil. 0.693 - 0.721 lb ai/A; 0 - day PHI **Residues (mg/kg) n** 

11 1 29 1 30 1 43 1 **Cyazofamid Basil**  **- dried**  **USA 0.693**  **- 0.721 lb ai/A;**  **0 -**  **day PHI Total number of data (n)**  4 **Percentage of censored data**  0% **Number of non -**  **censored data** 4 **Lowest residue** 11.000 **Highest residue** 43.000 **Median residue** 29.500 **Mean** 28.250 **Standard deviation (SD)** 13.150 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest**  **residue** 43.000

**- Mean + 4 SD**  80.849

**- CF x 3 Mean**  84.750 **Unrounded MRL** 84.750 **Rounded MRL 90**  High uncertainty of MRL estimate. [Small dataset]Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 33 of 45 Bean, l ima ( MRID 48629404 ) A tolerance of 0.08 ppm is appropriate for bean, succulent , shelled based on the residue data for l ima bean. 0.427 - 0.523 lb ai/A; 0 - 1 day PHI **Residues (mg/kg) n**  < 0.02 5 0.05 1 **Cyazofamid Crop**  **Lima Bean 0.427**  **- 0.523 lb ai/A**  **; 0**  **- day PHI**  **Total number of data (n)** 6 **Percentage of censored data** 83% **Number of non -**  **censored data** 1 **Lowest residue** 0.020 **Highest residue** 0.050 **Median residue** 0.020 **Mean** 0.025 **Standard deviation (SD)** 0.012 **Correction factor for censoring (CF)** 0.444 **Proposed MRL estimate**

**- Highest residue**  0.050

**- Mean + 4**  **SD** 0.074

**- CF x 3 Mean**  0.033 **Unrounded MRL** 0.074 **Rounded MRL 0.08**  High uncertainty of MRL estimate. [Small dataset and high level of censoring]Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 34 of 45 Bean, s nap ( MRID 48629403 ) A tolerance of 0.5 ppm is appropriate for bean, succulent based on the residue data for snap bean. 0.426 - 0.507 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  0.029 1 0.056 1 0.068 1 0.11 1 0.12 1 0.2 2 0.21 1 **Cyazofamid Snap bean**  **USA 0.426**  **- 0.507 lb ai/A;**  **0 -**  **day PHI Total number of data (n)**  8 **Percentage of censored data**  0% **Number of non -**  **censored data** 8 **Lowest residue** 0.029 **Highest residue** 0.210 **Median residue** 0.115 **Mean** 0.124 **Standard deviation (SD)** 0.072 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest**  **residue** 0.210

**- Mean + 4 SD**  0.411

**- CF x 3 Mean**  0.372 **Unrounded MRL** 0.411 **Rounded MRL 0.5** Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 35 of 45 Lettuce , head ( MRIDs 48629401 and 48629405 ) The appropriate tolerance for the leafy greens subgroup 4A is 10 ppm, which is the highest level for the representative crops of the subgroup: head lettuce (4 ppm), leaf lettuce (8 ppm), and spinach (10 ppm). 0.419 - 0.506 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  0.08 1 0.2 1 0.27 1 0.47 1 0.51 1 0.65 1 0.74 1 1.3 1 1.5 1 1.6 1 1.8 1 **Cyazofamid Head lettuce**  **USA and Canada 0.419**  **- 0.506 lb ai/A**  ; **0 -**  **day PHI Total number of data (n)**  11 **Percentage of censored data** 0% **Number of non -**  **censored data** 11 **Lowest residue** 0.080 **Highest residue** 1.800 **Median residue** 0.650 **Mean** 0.829 **Standard deviation (SD)** 0.612 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest residue**  1.800

**- Mean + 4 SD**  3.278

**- CF x 3 Mean**  2.487 **Unrounded MRL** 3.278 **Rounded MRL**  **4**Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 36 of 45 Lettuce , leaf ( MRIDs 48629401 and 48629405 ) The appropriate tolerance for the leafy greens subgroup 4A is 10 ppm, which is the highest level for the representative crops of the subgroup: head lettuce (4 ppm), leaf lettuce (8 ppm), and spinach (10 ppm). 0.427 - 0.587 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  0.54 1 0.8 1 0.91 1 0.93 1 1.4 1 1.8 1 2.8 2 2.9 1 3.6 1 4.5 1 **cyazofamid Leaf lettuce**  **USA and Canada 0.427**  **- 0.587 lb ai/A;**  **0 -**  **day PHI Total number of data (n)**  11 **Percentage of censored data**  0% **Number of non -**  **censored data** 11 **Lowest residue** 0.540 **Highest residue** 4.500 **Median residue** 1.800 **Mean** 2.089 **Standard deviation (SD)** 1.308 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest**  **residue** 4.500

**- Mean + 4 SD**  7.322

**- CF x 3 Mean**  6.267 **Unrounded MRL** 7.322 **Rounded MRL 8** Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 37 of 45 Pepper , bell (MRID 47528401) The appropriate tolerance for the fruiting vegetable group 8 - 10 is 0.9 ppm, which is the highest level for the representative crops of the subgroup: bell pepper (0.4 ppm), nonbell pepper (0.9 ppm), and tomato (0.2 ppm). 0.418 - 0.429 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  0.048 1 0.065 1 0.068 1 0.082 1 0.108 1 0.236 1 **Cyazofamid Bell Pepper**  **USA 0.418**  **- 0.429 lb ai/A;**  **0 -**  **day PHI Total number of data (n)**  6 **Percentage of censored data** 0% **Number of non -**  **censored data** 6 **Lowest residue** 0.048 **Highest residue** 0.236 **Median residue** 0.075 **Mean** 0.101 **Standard deviation (SD)**  0.069 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest residue**  0.236

**- Mean + 4 SD**  0.377

**- CF x 3 Mean**  0.304 **Unrounded MRL** 0.377 **Rounded MRL 0.4**  High uncertainty of MRL estimate. [Small dataset]Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 38 of 45 Pepper , nonbell (MRID 47528401) The appropriate tolerance for the fruiting vegetable group 8 - 10 is 0.9 ppm, which is the highest level for the representative crops of the subgroup: bell pepper (0.4 ppm), nonbell pepper (0.9 ppm), and tomato (0.2 ppm). 0.419 - 0.426 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  0.258 1 0.259 1 0.321 1 **Cyazofamid Non** **bell Pepper USA**  **0.419 -**  **0.426 lb ai/A; 0**  **- day**  **Total number of data (n)** 3 **Percentage of censored data** 0% **Number of non -**  **censored data** 3 **Lowest residue**  0.258 **Highest residue** 0.321 **Median residue** 0.259 **Mean** 0.279 **Standard deviation (SD)** 0.036 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest residue**  0.321

**- Mean + 4 SD**  0.424

**- CF x 3 Mean**  0.838 **Unrounded MRL** 0.838 **Rounded MRL 0.9**  High uncertainty of MRL estimate. [Small dataset]Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 39 of 45 Spinach (MRID 47870704) The appropriate tolerance for the leafy greens subgroup 4A is 10 ppm, which is the highest level for the representative crops of the subgroup: head lettuce (4 ppm), leaf lettuce (8 ppm), and spinach (10 ppm). 0. 347 - 0.366 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  1.61 1 2.03 1 2.1 1 2.18 1 2.94 1 3.34 1 3.49 1 3.64 1 4.74 1 6.52 1 **Cyazofamid Spinach**  **USA 0.347**  **- 0.366 lb ai/A**  ; **0 -**  **Day PHI Total number of data (n)**  10 **Percentage of censored data** 0% **Number of non -**  **censored data** 10 **Lowest residue** 1.610 **Highest residue** 6.520 **Median residue** 3.140 **Mean** 3.259 **Standard deviation (SD)** 1.486 **Correction factor for censoring (CF)**  1.000 **Proposed MRL estimate**

**- Highest residue**  6.520

**- Mean + 4 SD**  9.203

**- CF x 3 Mean**  9.777 **Unrounded MRL** 9.777 **Rounded MRL 10** Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 40 of 45 Tomato (MRID #s 45409031, 45638507, 45638508) The appropriate tolerance for the fruiting vegetable group 8 - 10 is 0.9 ppm, which is the highest level for the representative crops of the subgroup: bell p epper (0.4 ppm), nonbell pepper (0.9 ppm), and tomato (0.2 ppm). 0.413 - 0.434 lb ai/A; 0 - day PHI **Residues (mg/kg) n**  < 0.02 1 0.035 1 0.04 2 0.045 2 0.05 2 0.06 3 0.065 1 0.075 1 0.085 1 0.12 1 0.16 1 **Cyazofamid Tomato**  **USA 0.413**  **- 0.434 lb ai/A**  ; **0 -**  **day PHI Total number of data (n)**  16 **Percentage of censored data** 6% **Number of non -**  **censored data** 15 **Lowest residue** 0.020 **Highest residue** 0.160 **Median residue** 0.055 **Mean** 0.063 **Standard deviation (SD)** 0.035 **Correction factor for censoring (CF)** 0.958 **Proposed MRL estimate**

**- Highest residue**  0.160

**- Mean + 4 SD**  0.202

**- CF x 3 Mean**  0.181 **Unrounded MRL** 0.202 **Rounded MRL 0.2** Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 41 of 45 **References** Acierto, A., 2/18/04, DP# D298915, Cyazofamid

– Meeting Report of the Metabolism Assessment Review Acierto, A., 2/20/04, DP# D285680, PP#1F06305, Cyazofamid. Petition for the Establishme nt of Permanent Tolerances for U se on Cucurbits, Potatoes, Tomatoes, and Imported W ine Grapes. Summary of Analytical Chemistry and Residue Data. Acierto, A., 3/18/09, DP# D357042, Cyazofamid. Amend Section 3 to Add Uses on Fruiting Vegetables, Okra, Grape (East of the Rocky Mountains), and Greenhous e Vegetable Transplants. Summary of Analytical Chemistry and Residue Data. Acierto, A., 2/24/10, DP# D371162, Cyazofamid. Tolerance Petition for Uses on Brassica (Cole) Leafy Vegetables Crop Grou p 5, Turnip Greens, Spinach, and Hops. Summary of Analytical Chemistry and Residue Data. Hanson, B., 8/3/10, DP# D376500, Cyazofamid. Human Health Risk Assessment for Proposed Section 18 Use on Basil. Kolbe, E., 10/22/03, DP# D286108, PP# 3F6595. Cyazofamid on Potatoes, Tomatoes, Cucurbit and Grapes. Tolerance Method Review and Multi -Residue Method Review. PC Code 085651 (MRID#: 454090 - 33, 456385 - 08, 454090 - 34, 454090 - 32, 454090 - 20, 45 4090 - 22) ; ACB # B02 - (58 - 61). Kolbe, E., 2/27/06, DP# D326164, PP# 3F6595. Review of Resubmitted Analytical Method for Cyzofamid and its Metabolite CCIM in Crops. PC Code 085651 (MRID#: 46550401); ACB Project # B06- 13. OPPTS/US EPA, September 2004, Pesticide Fact Sheet: CyazofamidCyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 42 of 45 **Appendix A. Field Trial Geogra**  **phic Distribution** . **TABLE A .1.**  **Trial Numbers and Geographical Locations** . NAFTA Gro wing Zones Head Lettuce Leaf Lettuce

Submitted Requested 1 Submitted Requested 1

Canada US Canada US 1 1 -- 1 2 /1 2

-- -- 1 2 /1 2 1A -- -- -- -- -- -- 2 -- -- 1 2 /1 2 1 -- 1 2 /1 2 3 1 -- 1/1 1 -- 1/1 4 -- -- -- -- -- -- 5 2 1 -- 2 1 -- 5A 1 -- -- 1 -- -- 5B 1 3 -- 1 3 -- 6 -- -- -- -- -- -- 7 -- -- -- -- -- -- 7A -- -- -- -- -- -- 8 -- -- -- -- -- -- 9 -- -- -- -- -- -- 10 4 3

-- 6/4 4 3

-- 6/4 11 -- -- -- -- -- -- 12 1 1 -- 1 1 -- Total 11 3 5 8/6 11 3 5 8/6 1 For the US, a s per O CSPP 860.1500, Table 5 for head and leaf lettuce. The second number reflects a 25% reduction in the number of trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application results in no quantifiable residues. For Canada, as per Regulatory Directive - Dir98 - 02, Section 9 - Crop Field Trials. Appendix III, Table 2 for lettuce. 2 Trial can be conducted in either Zone 1 or Zone 2. 3 HED has concluded that trial pairs 08 - CA* 04/08 - CA* 05 and 08 - CA03/08 - CA19 for head lettuce, and trial pairs 08 - NM14/08 - NM12, and 08 - CA*22/08 - CA* 21 for leaf lettuce each constitute a single trial with replicate samples for purposes of OCSPP 860.1500 data requirements. **TABLE A.2.**  **Trial Numbers and Geographical Locations** . NAFTA Growing Regions Basil Submitted Requested 1 Canada U.S. 1 -- -- -- 1A -- -- -- 2 2 (field trials) -- -- 3 1 (greenhouse trial) -- -- 4 -- -- -- 5 -- -- -- 5A -- -- -- 5B -- -- -- 6 -- -- -- 7 -- -- -- 7A -- -- -- 8 -- -- --Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 43 of 45 **TABLE A.2.**  **Trial Numbers and Geographical Locations** . NAFTA Growing Regions Basil Submitted Requested 1 Canada U.S. 9 -- -- -- 10 2 (field trials) 1 (greenhouse trial) -- -- 11 -- -- -- 12 -- -- -- Total 4 (field trials) 2 (greenhouse trials) -- 3 1 As per O CSPP 860.1500, Table s 2 and 3 for basil as a representative commodity of the herb crop group/subgroup; Tables 1 and 5 do not include basil. Three field trials are required in major basil producing regions. **TABLE A.3**  **. Trial Numbers and Geographical Locations**  . NAFTA Gro wing Zones Snap Bean Lima Bean

Submitted Requested 1 Submitted Requested 1

Canada US Canada US 1 -- -- 1/1 -- -- -- 1A -- -- -- -- -- -- 2 3 -- 1/1 2 2

-- 4/3 3 -- -- 1/1 -- -- -- 4 -- -- -- -- -- -- 5 2 -- 3/2 1 -- 1/1 5A -- -- -- -- -- -- 5B -- -- -- -- -- -- 6 -- -- -- -- -- -- 7 -- -- -- -- -- -- 7A -- -- -- -- -- -- 8 -- -- -- -- -- -- 9 -- -- -- -- -- -- 10 2 -- 1/0 2 -- 2/1 11 1 -- 1/1 1 -- 1/1 12 -- -- -- -- -- -- Total 8 8/6 6 2 8/6 1 A s per OCSPP 860.1500, Table 5 for snap bean or lima bean . The second number reflects a 25% reduction in the number of trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application results in no quantifiable residues. 2 HED has concluded that lima bean trial pairs MD15/MD24 and NC30/NC31 each constitute a single trial with replicate samples for purposes of OCSPP 860.1500 data requirements.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 44 of 45 

### Appendix B: **International Residue Limits**

Cyazofamid (085651; 02/01/2012) Table B. Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 Codex 3 40 CFR 180. 601 : sum of 4 - chloro - 2 - cyano -N ,Ndimethyl - 5 - (4 - methylphenyl) - 1 Himidazole - 1 - sulfonamide and its metabolite, 4 - chloro - 5 - (4 - methylphen yl ) - 1 H

- imidazole - 2 - carbonitrile, calculated as the stoichiometric equivalent of cyazofamid 4 - chloro - 2 - cyano -N ,Ndimethyl - 5 - (4 - methylphenyl) - 1 H - imidazole - 1 - sulfonamide, including the metabolite 4 - chloro - 5 - (4 - methylphenyl) - 1 H - imidazole - 2 - carbonitrile None

Com modity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex 3 Bean, succulent 0. 5 Bean, succulent, shelled 0.0 8 Leafy greens subgroup 4A 10 Basil, fresh leaves 30 Basil, dried leaves 9 0 Vegetable, tuberous and corm, subgroup 1C 0.02 0.02 potatoes Vegetable, fruiting, group 8 - 10 0. 9 0.2 tomatoes Completed: M. Negussie; 02/02/2012 1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and not those proposed by the applicant. 2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes. 3 * = absent at the limit of quantitation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed postharvest treated commodity, such as processing of treated stored wheat. (fat) = to be measured on the fat portion of the sample. MRLs indicated as proposed have n ot been finalized by the CCPR and the CAC.Cyazofamid Summary of Analytical Chemistry and Residue Data Barcode D 396051

Page 45 of 45 **Appendix C: Chemical Names and Structures of Cyazofamid and Identified Meta**b **olites Table C.**  **Identification of Com pounds from** **the Cyazofamid Metabolism Studies.** Common name/ code/matrix Chemical name Chemical structure Cyazofamid/ IKF - 916 4 - chloro - 2 - cyano -N,N - dimethyl - 5 - (4 - methylphenyl) - 1 H

- imidazole - 1 - sulfonamide N N C H 3 Cl C N S O 2 N ( C H 3 ) 2 CCIM 4 - chloro - 5 - p - tolylimidazole - 2 - carbonitrile

N H N C H 3 Cl CN CCBA 4 - (4 - chloro - 2 - cyanoimidazol - 5 - yl)benzoic acid N H N Cl C N O H O CCIM - AM 4 - chloro - 5 - p - tolylimidazole - 2 - carboxamide

N H N C H 3 Cl O N H 2 CTCA 4 - chloro - 5 - p - tolylimidazole - 2 - carboxylic acid