RI C K S NYDER GOVERNO R

March 22, 2016
Ms. Tawanda Maignon ST ATE OF MICHIGAN DEPARTMENT OF AGRICULTURE AND RURAL DEVELOPMENT

Risk Integration, Minor Use and Emergency Response Branch U
.S. EPA 

### I Office of Pesticide Programs (7505P) Room S4900 , One Potomac Yard 2777 S. Crystal Drive Arlington, VA 22202 Dear Ms
. Maignon : JA M IE CLOVER ADA MS DIRECTO R

Approval of this application is requested pursuant to section 18 of the Federal Insecticide Fungicide and Rodenticide Act as Amended , 7 U.S
.C
. §136p , for the use of pyridate to control weeds in mint grown in Michigan during the 2016 g rowing season . The fo llowing information is provided as requested in 40 CFR , Part 1 66 , Subpart B.
A. Summary of General Information 1. Type of Exemption: Specific 2. Contact Persons: Brian Verhougstraete (Administration) Pesticide Registration Program Manager Michigan Department of Agriculture Pesticide and Plant Pest Management Division Constitution Hall, 5th Floor 525 Allegan Street Lansing , Ml 48909 Telephone: (517) 284-5655 Fax: (517) 335-4540 E-mail : verhougstraeteb@michigan
.gov

CONST ITUTI ON HALL • P
.O
. BOX 30017 • LANSING, MICH IGAN 48909 www.m ich jgan .gov/mdard • (800) 292-3939Steve Salisbury (Technical) Mint Industry Research Council PO Box4059 Salem , OR 97302-1059 Phone : 503-551-3747 Email : steve@pacificagresources
.com Dr
. Bernard Zandstra (Scientific) Department of Horticulture M ichigan State University 1066 Bogue Street East Lansing , Ml48824 Phone : 517-353-6637 Email: zandstra@msu .edu Doug lrrer (Economics) Michigan Mint Growers Association 6700 West Centerline Road St. Johns, Ml 48879 Phone: 989-640-4472 Email : dougi@sceoinc.com Liesbeth Bosman (Registrant) Belchim Crop Potection, Inc. Technologielaan 7 1840 Londerzeel Belgium Phone : +32 (0) 473 86 52 33 Email : Liesbeth.Bosman@Belchim.com3. Description of Pesticide Active Ingredient: Pyridate Trade Name: Tough Herbicide 5EC, not currently reg istered in U
. S
. Formulation: Emulsifiable concentrate formulated at 55
.8% (5
.0 lb
. ai. per gal.) and 44
.2 % inert ingredients. Registrant/Manufacturer: Belchim Crop Protection a Belgium based company (EPA Company No. 91746). The U
.S. distributor is Engage Agro USA Corp. Material Safety Data Sheet (MSDS) and labels are attached. 4. Description of Proposed Use a . Sites to be Treated There are nearly 1,400 acres of mint grown in Michigan
. It is estimated th at approximately 1,250 (90%) ofthis acreage will need to be treated with Tough
. The mint production areas are located in Michigan counties of Clinton , Ingham , Ion ia , Newaygo, Saginaw, and Shiawassee
. The soils ofthese mint growing counties are generally productive , deep , and fertile in agricultural areas . b
. Method of Application The herbicide will be applied by ground-driven spray equipment by licensed applicators according to the EPA approved product label. Tough will not be applied by aerial methods or through any type of irrigation system
. c. Rate of Application A maximum of .9375 lb. active ingredient per acre (24 ounces of product per acre) in 20-40 gallons of water per acre will be appl ied during the growing season . d
. Maximum Number of Applications Two applications ofTough per growing season may be made if necessary with a min imum of 14 days between applications. Applications may be made between the dates ofApril 1 and December 31 , 2016
. No applications will be made within 49 days of harvest. e. Total Acreage to be Treated It is estimated that approximately 1 ,250 acres (90% oftotal Michigan acreage) wil l need to be treated with Tough
. f
. Total pesticide to be used An estimated 470 gallons (2 ,350 lbs of a .i.) of herbicide are expected to be applied
. 1 ,250 acre* 24 fl.oz
. * 2 applications 

### = 470 gal. of formulated product. 470 gal* 5 lb a .i./ gal= 2 ,350 lbs of active ingredient.g. Use season We are requesting application beg inning April1 through December 31 , 2016. A fall application after harvest may be necessary if conditions promoting weed growth occur. No applications will be made within 49 days of harvest. h. Harvest Dates The majority of peppermint acreage is harvested once in August. However, some peppermint growers are double cutting their crop. Double-cut mint is harvested twice during the growing year, once in June and again in late August or early September
. Spearmint is harvested twice during the growing season, once in the middle of June and again in the middle ofAugust. i. Other Restrictions
. User Precautions
. and Requirements Federal and supplemental labels address reentry and worker protection , environmental hazards and restrictions (see attached label)
. Treated fields or forage from treated fields may not be used for livestock feed or grazing. Tough will not be applied through any type of irrigation system or by air
. To protect endangered freshwater invertebrate species, Tough will not be applied within 100 yards of any freshwater spring
. 5. Alternative Methods of Control a. Registered Post-Emergent Herbicide Alternatives 1
. Bentazon (Basagran) - Pr ovides inconsistent (partial) post-emergence control of Kochia
. Does not control pigweed
. Weeds eme rging after application are not controlled
. 2. Bromoxynil (Maestro)- Phytotoxic to actively growing mint. Cannot be applied above 70 degrees F to actively growing mint. Only gives partial control of Kochia and Pigweed seedlings. Kochia and Pigweed seeds germinate (multiple flushes) throughout the growing season . 3
. Clethodim (Select Max)- Grass weed control only. 4. Clopryalid (Stinger) - For spot treatment, post emergence control of broadleaf weeds (canada thistle , dandelion). Destroys mint which comes in contact with herbicde. Does not control Kochia or Pigweed 5. MCPB (Thistrol) - Can only be applied early post-emergent to weeds and to dormant or small/newly emerged mint. It is limited to partial control of Canada thistle and field bindweed
. Does cause crop injury and loss of oil yield
. 6. Quizalifop (Assu re II) - Grass weed control only
.7. Sethoxydim (Poast Plus)- Grass weed control only. 8. Terbacil (Sinbar)- Does not control Kochia. Pigweed has developed resistant biotypes due to years of continuous use. It is not effective on weeds that have grown beyond the seedling stage. Cannot be used when rotating from mint into other crops the following year due to soil persistence and crop rotational restriction
. Cannot be used on sandy, loamy sands , or soils with less than 1% organic matter without crop injury
. b. Other alternatives Mechanical weed control methods such as tillage are not feasible or practiced in actively growing mint due to the destruction ofthe crop. Tillage in mint at any time also spreads the disease Verticillium Wilt, a fungal pathogen in mint which is spread by the movement of soil and debris. Tillage also spreads the rhizomes and stolons of perennial weeds
. Hand rogueing is cost prohibitive and does not provide season long control ofweeds as weed seeds continue to germinate in the soil throughout growing season. I n addition, the labor needed for hand weeding is not available in most mint growing regions
. Crop rotation is practiced when feasible , but mint being a perennial crop is left in production for 3 to 5 years, or longer
. Research on biological control methods is currently being conducted, but as of to date no effective methods have been developed. c. On-going research for chemical alternatives The mint industry has placed a high priority on finding alternatives to pyridate for postemergence broadleaf weed control. The industry has diligently invested several hundred thousands of dollars of research funds for the past decade to this effort
. Numerous preemergence and postemergence herbicides have been tested and evaluated with little or no success . Preemergence herbicides evaluated include pendamethalin, terbacil , saflufenacil, sulfentrazone, flumioxazin , oxyfluorfen, pyroxasulfone and both oxyfluorfen and flumioxazin impregnated on fertilizer have been tested. Postemergence herbicides that have been tested include bentazon, terbacil , bromoxynil , bicyclopyrone , mesotrione, tembotrione, topramezone, fluroxypyr, MCPB , and carfentrazone. These herbicides are either too injurious to the mint or do not adequately control the pigweed. A letter from Dr
. Rick Boydston, USDA-ARS , is attached summarizing mint herbicide research since 2006. In summary, despite extensive efforts the mint industry has not been able to successfully find an adequate replacement for pyridate (Tough herbicide) to provide postemergence weed control that does not cause significant injury to the mint crop. Therefore, weed control remains an urgent situation challenging the ability to produce high quality mi nt oil. In addition to the urgency ofthe situation, it is important to note that postemergence broadleaf weed control has recently developed into a non-routine situation due to the increased demand for double-cut production acreage . Manyacres have been forced to double-cut production to meet recent global regulatory and market demands. Further description ofthis non-routine situation is discussed in Section B Part 2 (Description ofthe Emergency Condition) of this request. 

### 6
. Efficacy of the Proposed Use Results of efficacy and comparative field trials are attached
. Tough selectively controls annual weeds in mint without causing significant crop injury
. Risks to rotational crops are minimized due to the short half-life and low soil persistence leading to no res idual impact to subsequent crops. Tough is the only known broadleaf herbicide that can provide post-emergent control of weeds without impacting crop yield
. Since there is a limited amount oftrial data from Michigan , a letter of support from Dr. Bernard Zandstra , Michigan State Univer sity, is attached explaining the benefits and usability ofTough in mint production
. 

### 7. Residue Information Residue trials for mint we re conducted by the IR-4 Program i n 1994
. Applications made in accordance with the requested provisions are not expected to result in residues of pyridate and its metabolites in excess of 0.2 ppm for pepperm int and spearmint tops
. These tolerances have been established by the EPA and are recorded under CFR 180.462
. Secondary residues in meat, poultry, and eggs are not expected to result. 

### 8. Risk Information On May 3, 2000 the EPA established tolerances of 0
.2 ppm for residues of pyridate and its metabolites in/on peppermint and spearmint tops. Information regarding pyridate toxicology and aggregate exposure can be found in the fi nal rule published in the Federal Register May 3 , 2000, volume 65 , number 86 , pages 25647-25652 (attached)
.a. Human Health Tough herbicide poses little potential risks to humans , domestic animals , wildlife , and the environment. The acute oral LDSO for male rats is> 5,000 mg/kg
. The active ingredient has a low dermal irritation potential and a low inhalation hazard
. Acute dermal LD50 for rabb its is > 2,000 mg/kg
. Inhalation LCSO >4.37 mg./L air. Primary dermal irritation study indicated it is mildly irritating to rabbit skin (EPA Health Effects Division of the Office of Pesticide Programs, 2000). The EPA concluded that residues of pyridate in drinking water do not contribute significantly to the aggregate acute human health risk
. The acute human health risks resulting from exposure to pyridate in food and water are below EPA's level of concern for all population subgroups. As for chronic risk, the EPA also concluded that no harm will result from aggregate chronic exposure. It was also determined that pyridate is not carcinogenic in either rat or mouse, and therefore is not expected to pose a cancer risk to humans
. The product label addresses the risks to worker/applicator by outlining handler precautions and required personal protective equipment. b
. Potential to be found in drinking water The potential for exposure to residues of pyridate in drinking water is negligible due to its low water solubility (1
.5mg/L at 20 C), strong soil adsorption (Kd 

# =.3- 26) and short half-life (7-21 days). Pyridate is essentially immobile in all soil types and any risks to surface or groundwater contamination will be negligible
. The EPA Health Effects Division determined that pyridate does not possess the environmental fate parameters associated with a compound that could leach to groundwater. However, the parameters of its degradate indicate that under unusual conditions such as flooding, where anaerobic cond itions persist in topso il for up to 60 days , the degradate could possibly leach to groundwater or run off to surface water
. Pyridate is not listed in the EPA Pesticides in Ground Water Database , nor is there an EPA Maximum Containment Level or health advisory. c. Residential Uses Pyridate is not registered for use in ornamentals or in residential areas . d
. Common Mode of Action Pyridate is a Group 6 herbicide, HRAC Group C3 (Herbicide Resistance Action Committee , www. hracglobal.com). It belongs to the phenyl-pyridazine family of herbicides
. Its site of action is inhibition photosynthesis by blocking el ectron transport in photosystem II (reactions taking place in the chloroplast thylakoid membranes).e. Endangered orThreatened Species Endangered or threatened species listed by the USFWS within the mint production counties of Clinton, Ingham , Ionia, Newaygo, Saginaw, and Shiawassee are listed in the attached table. The use ofTough herbicide in accordance to the label in mint fields should not pose a risk to any threatened or endangered species
. f. Beneficial Organ isms Tough is not toxic to bees and other beneficial insects (i.e
. lady beetles , predatory mites)
. See the attached EPA Environmental Fate and Effects Division (EFED) report
. g . Fish and Aquatic Organisms Pryridate is considered toxic to estuarine organisms
. However, due to its strong soil adsorption and short half-life , if applied according to the label it should not pose a risk to estuarine organisms (see attached EPA EFED report)
. The label states that this material should not be applied within 100 yards of any freshwater spring , directly to water, to areas where surface water is present, or to intertidal areas below the mean high water mark
. 9. Coordinate with Other Agencies The Michigan Fish and Game Office ofthe U.S. Fish and Wildlife Service will receive a copy of this request. Any comments received will be forwarded to the U
.S
. EPA. 10. Notification of Registrant Belchim Crop Protection has been notified and their letter of support is attached. In addition , Engage Agro USA Corp
. is the U
.S
. distributor and they have also been notified
. A letter of support from Engage Agro USA is also attached. 11. Enforcement Program The Michigan Department of Agriculture and Rural Development (MDARD) has adequate authorities for enforcing provisions of Section 18 emergency exemptions. MDARD will require the registrant (or manufacturer, if unregistered) ofTough herbicide , Belchim Crop Protection , to prepare and make available to end users supplemental labeling that complies with MDARD and EPA requirements for the emergency use , if approved
. Applicators will be required to keep adequate records of application use and acreage. The Mint Industry Research Council (MIRC) , in cooperation with Belchim Crop Protection and Engage Agro USA, will be required to provide the MDARD a report summarizing results of the emergency use after the end ofthe use period. 12. Repeat Uses Tough has been previously used under a Section 18 from 1999-2000
. Tough was later registered under an SLN 24c from 2001-2007 after tolerances were established in 2000
.13. Progress Toward Registration Registration and tolerance were established through the IR-4 by the EPA in May of 2000. The Final Rule was published in the Federal Register vol. 65, No. 86, May 3, 2000 pages 25647-25652 (attached). Tolerances were established for peppermint and spearmint tops at 0.20 ppm (CFR 180.462). Product registration was voluntarily cancelled by the registrant (Syngenta) and the product was no longer marketed in the U.S. Recently, Belchim Crop Protection acquired the marketing rights for pyridate from Syngenta. It is understood that Belchim is working with the EPA to re-register Tough in the U.S. B. Summary of Economic Loss 1 . Pest(s) to be Controlled The pests causing an emergency are broadleaf weeds, in particularly Redroot Pigweed , Armaranthus retroflexus and Kochia, Kochia scoparia. 2. Discussion ofthe Emergency Condition This request is due to the emergency condition existing in mint from the postemergence of pigweed, kochia, and other broadleaf weed communities that cannot be effectively controlled in active growing mint crops. All crops including mint suffer yield losses from populations of weeds, but unlike other crops, the quality of mint oil also is affected by weeds. A quality marketable mint crop is dependent upon weed free fields. The recent increase in global demand for the production of double-cut mint oil has created a non-routine situation that poses additional stress on the need for adequate postemerge nce broadleaf weed control. Preemergence herbicides applied in February/early March to dormant mint dissipate to low levels that no longer control weeds after 4-6 weeks. The mint crop canopy suppresses any new weed emergence or establishment after this period. Once the mint canopy is removed with a mid to late June harvest (first cutting), new weed flushes follow. These new flushes include both summer annual grasses and later germinating broadleaf weeds such as pigweeds. The grass weeds are easily controlled with registered grass active herbicides. However, there are no effective postemergence herbicides that are labeled in mint for pigweed control during the second half ofthe growing season following the first harvest of mint. The increased demand for double-cut mint is a resu lt of both global regulatory challenges and the increasing desire for the oil quality that is produced in double-cut production. The global regulatory issues involve the concern of menthofuran and pulegone contents in the mint oil and the limits ofthese compounds that are allowable in oil to deem it acceptable in markets. The reduction of these compounds and the increase of other desirable oil quality traits can be achieved through double-cut production. The market has shifted to a higher demand for double-cut mint, but the acreage to meet the demand is not adequate due to management challenges associated with double-cut production. Postemergence broadleafweed control is the primary management challenge facing double-cut production. Producers do not haveviable broadleaf weed control options to address this challenge. Redroot pigweed present in mint at 1
.6 weeds/yd2 renders mint oil unmarketable, due to off-flavors imparted during the distillation process (attachment). OSU research also demonstrated that a redroot pigweed infestation of 10 plants/ft2 caused a peppermint oil yie ld reduction 34.4 lbs/acre , a 46% reduction (attached)
. Furthermore , both redroot and prostrate (A. blitoides) pigweeds have developed terbacil resistant biotypes. Kochia, a summer annual, can reach heights of six feet high and several feet in diameter, hindering harvest operations and competes for nutrients and light. In addition , an infestation of 2 .3 kochia plants/ft2 can reduce mint oil yields by over 30% (attachment) in addition to reducing oil quality
. Mechanical tillage is not a post emergence weed control option in mint because tillage will destroy growing mint, eliminate irrigation rills in surface irrigated fields , and will spread devastating diseases in mint such as Verticillium wilt (Verticillium dahliae). Terbacil (Si nbar ), the commonly used herbicide registered for weed control in mint, is weak on pigweed species and has become even less effective in controlling pigweeds due to the development of resistant biotypes
. Add itionally, terbacil cannot be used when weeds are beyond the seedling stage and when rotating from mint to other crops due to residual carryover. The only alternative method of controlling these weeds is handrogueing , but the unavailability of labor and excessive cost w here labor is available , eliminates rogueing as a viable weed control method. Again , there are presently no effective post-emergent means of contr olling these weeds in mint. The mint industry has been diligently investing research funds to discover effective postemergent broadleaf weed herbicides that are safe to the crop. Pyridate has proven to be effective on broadleafweeds as well as possesses acceptable post-emergence crop safety needed for mint production. Populations of problem weeds have reached economically devastating levels and is impacting the producer's ability to compete in the market. Additionally, the recent increased demand for double-cut mint has forced production into and created a non-routine situation for mint producers who have no effective and viable postemergence broadleaf weed control options
. The use ofTough herbicide for postemergence weed control in mint is critical to maintaining U
.S. mint oil quality and market share in today's global economy. 3. Discussion of Economic Loss Red root Pigweed/Kochia and broadleaf weed communities have become serious weed pests of mint growers in Michigan. The lack of any post emergent weed control option , (lack of a registered satisfactory herbicide , and the presence of herbicide resistant pigweed and kochia) have created an emergency situation for Michigan m int growers. Economic thresholds for these problem weeds are very low
. Weeds res istant to herbicides which mature and form seeds , soon establish large populations ofthe resistant biotype , if not controlled
. Studies performed by Oregon State Universit y weed scientists show yield lossesranging from 22%to 47% from the target weeds individually (attachment)
. Kochia and Red root Pigweed are often found in complexes of other weeds, which further reduces the yield and quality of mint oil. Five-Year History of Michigan Production Average Average Gross Cost of Net Year Yield Price Revenue Production Revenue (lbs 

### I acre) 

### ($I lb) 

### ($I acre) 

### ($I acre) 

### ($I acre) 2011 71 $21 $1,488 $1,275 $213 2012 72 $21 $1,516 $1,299 $217 2013 58 $21 $1,208 $1,035 $173 2014 65 $21 $1,365 $1,170 $195 2015 69 $21 $1,449 $1,242 $207 Average 67 $21 $1,405 $1,204 $201 1
. Yield and price data were obtained from mint industry oil growers and buyers. 2. Cost of production is based on local industry know ledge. 3. A loss does not necessarily mean a negative cash flow, but rather that the grower will not earn a return on capital and management contributions (hourly wage, labor, etc) equal to what could be earned in an alternative investment ofthe land producing the mint crop.

Tier 2 Analysis A Tier 2 Significant Economic Loss (SEL) analysis illustrates the reduction of oil yield and quality as well as the loss of gross revenue due to the devaluation oftainted oil resulting from weed contaminants. The yield comparison reflects a 35% yield reduction (OSU trial data) on the portion ofthe acres (90%) faced with the impact of postemergent weed control challenges. Furthermore, the yield calculations are based on the five-year average (2011-15) of 67 lbs/acre. As previously stated in this request , the estimated acreage of Michigan mint is 1,400 acres and approximately 1 ,250 acres (90%) would be treated with Tough herbicide. As for marketable oil quality, it is estimated that the use ofTough herbicide would increase pure quality oil by 20% , thus reducing the amount of tainted devalued oil by the same. The devaluation oftainted oil ranges from a small percentage deduction tocomplete rejection/loss. Based on industry knowledge, an average devaluation of 35% was used for this analysis. The Emergency situation results in 20% more tainted oil that has 35% less value realized by the growers. In all, this is a gross revenue loss greater than $1Million to the mint producers in Michigan. Tier 2 Michigan Economic Analysis of Yield and Quality Loss

Baseline Emergency Change %Change Yield (lbs/acre) 139,257 93,800 -45,457 -33% Pure (%ofyield) 90% 70% (lbs/acre) 125,331 65,660 -59,671 -48% Tainted (% ofyield) 10% 30% (lbs/acre) 13,926 28,140 14,214 102% Price, Pure ($/lb) $21.00 $21.00 Price, Tainted ($/lb) $13.65 $13.65 Gross Revenue ($/acre) $2,822,042 $1,762,971 -$1,059,071 -38%On behalf of Michigan's mint producers, I appreciate your consideration of this request. Should you have any questions please feel free to contact me . Sincerely, /

# ~**---rr--~------==--=--** Brian Verhougstraete Pesticide Registration Program Manager Pesticide and Plant Pest Management Division cc: Bruce Wilkinson, EPA Region V Steve Salisbury, Mint Industry Research Council Bernie Zandstra, Michigan State University
Enclosures